• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Methyl carbamate compound as active for skin and / or hair treatment. The present invention relates to the cosmetic, dermatological or pharmaceutical (therapeutic) use of compounds of formula (I) or a pharmaceutically acceptable salt of a compound of formula (I) or a mixture containing two or more such compounds or salts thereof. wherein r ^ 1 ^ denotes hydrogen or an organic radical having 1 to 14 carbon atoms, r ^ 2 ^ denotes or an organic radical having 1 to 14 carbon atoms, and where optionally r ^ 1 ^ and r ^ 2 ^ are covalently bonded together, preferably such that a 3- to 8-membered ring is formed for the treatment of hair or skin. The invention further relates to cosmetic, dermatological or pharmaceutical compositions and preparations (compositions) comprising one or more compounds of formula (I) suitable for treating human skin and / or hair and corresponding methods. The invention further relates to compounds of formula (I) as a drug, their use for the preparation of a pharmaceutical composition for treating human skin and / or hair and to certain novel compounds of formula (I).
    公开号:BR112012029959B1
    申请号:R112012029959-0
    申请日:2010-05-25
    公开日:2018-01-23
    发明作者:Vielhaber Gabriele；Oertling Heiko；Schaper Karin；Gömann Claudia；Brodhage Rahim
    申请人:Symrise Ag；
    IPC主号:
    专利说明:

    (54) Title: MENTILE CARBAMATE COMPOUNDS, THEIR USES, COMPOSITIONS AND COSMETIC METHODS FOR SKIN AND / OR HAIR LIGHTENING (51) lnt.CI .: A61K 8/44; A61K 8/92; C07C 271/32; A61Q 19/02; A61Q 5/08 (52) CPC: A61K 8/44, A61K 8/922, C07C 271/32, A61Q 19/02, A61Q 5/08 (73) Holder (s): SYMRISE AG (72) Inventor (s) : GABRIELE VIELHABER; HEIKO OERTLING; KARIN SCHAPER; CLAUDIA GÕMANN; RAHIM BRODHAGE
    1/135
    Invention Patent Descriptive Report for
    MENTILE CARBAMATE COMPOUNDS, THEIR USES, COMPOSITIONS AND COSMETIC METHODS FOR SKIN AND / OR HAIR LIGHTENING.
    [001] The present invention relates to the cosmetic, dermatological or pharmaceutical (therapeutic) use of certain menthol carbamate compounds of formula (I) indicated below, in particular, as bleaches (skin and / or hair bleaches). The invention also relates to cosmetic, dermatological or pharmaceutical compositions and preparations (compositions) comprising one or more compounds of formula (I) suitable for bleaching human skin and / or hair and the corresponding methods. in addition to compounds of formula (I) as a drug, their use for the preparation of a pharmaceutical composition for whitening human skin and / or hair and certain new compounds of formula (I) · [002] Active whitening ingredients of skin intervenes, in one form or another in melanin or catabolism metabolism. Melanin pigments, which are usually brown to black in color, are formed from the skin's melanocytes, transferred to the keratinocytes and o the skin or hair its color. In mammals, brown-black eumelanins are mainly formed from aromatic hydroxy-substituted amino acids, such as L-tyrosine and LDOPA, yellow to red phaeomelanins in addition from sulfur-containing molecules (Cosmetics & Toiletries, 1996, 111 (5 ), 43-51). Starting from L-tyrosine, L-3,4-dihydroxyphenylalanine (L-DOPA) is formed by the main enzyme tyrosinase containing copper and in turn is converted from tyrosinase to dopachromine. Through a series of steps catalyzed by various enzymes, the latter is oxidized to form melanin.
    Petition 870170023194, of 04/07/2017, p. 4/150
    2/135 [003] Skin lightening agents are used for several reasons: if for some reason the melanocytes that make up the melanin in human skin are not evenly distributed, pigmentation spots occur that are either lighter or darker than the surrounding skin area. To overcome this problem, skin and hair lightening agents are sold, which at least partially contribute to balancing pigment spots of this type. In addition, many people have a need to lighten their naturally dark skin color or to prevent skin pigmentation. This requires very safe and effective skin and hair lightening agents. Many skin and hair lightening agents contain more or less powerful tyrosinase inhibitors. This is just one possible way to lighten skin and hair, however. [004] In addition, UV-absorbing substances are also used to protect against the increased pigmentation of the skin caused by UV light. This is a physical and purely induced effect, however, and must be distinguished from the biological action of skin lightening, cellular melanin forming agents, which can also be detected in the absence of UV light. In addition, UV absorbers do not cause true skin lightening but only inhibit the increase in skin pigmentation caused by UV light.
    [005] Cosmetic or pharmaceutical (therapeutic) preparations with skin and / or hair lightening activity are known in the prior art.
    [006] US 4,959,393 discloses 4-alkyl resorcinols as skin and / or hair lightening agents.
    [007] WO 2004/105736 teaches certain diphenylmethane derivatives as skin and / or hair lightening agents.
    [008] WO 2007/110415 proposes certain trimers of diacetyl as skin and / or hair lightening agents.
    Petition 870170023194, of 04/07/2017, p. 5/150
    3/135 [009] Hydroquinone, hydroquinone derivatives such as, for example, Arbutin, vitamin C, ascorbic acid derivatives such as, for example, ascorbyl palmitate, kojic acid and kojic acid derivatives, such as, for example, kojic acid dipalmitate, are used in particular in commercial cosmetic or therapeutic skin and hair lightening preparations.
    [0010] One of the most commonly used skin and hair lighteners is hydroquinone. However, this compound has a cytotoxic effect on melanocytes and is irritating to the skin. For this reason, such preparations are no longer authorized for cosmetic applications in Europe, Japan and South Africa, for example. In addition, hydroquinone is very sensitive to oxidation and can be stabilized only with difficulty in cosmetic formulations.
    [0011] Arbutin (beta-Arbutin) is a hydroquinone glycoside, which hydrolyzes in situ to form hydroquinone and is therefore similarly questionable in toxicological terms like hydroquinone. [0012] Vitamin C and ascorbic acid derivatives have inadequate character on the skin. In addition, they do not act directly as tyrosinase inhibitors, but instead reduce the intermediate color steps of melanin biosynthesis.
    [0013] Kojic acid (5-hydroxy-2-hydroxymethyl-4-pyranone) is a tyrosinase inhibitor, which inhibits its catalytic action by chelating the copper atoms in the enzyme; it is used in commercial skin and hair lightening agents, but has a high sensitizing potential and causes contact allergies.
    [0014] The purpose of the present invention was to remedy the disadvantages of the prior art and, in particular, to provide effective skin and / or hair whitening assets, in particular skin whitening assets, which preferably achieve lightening activity. skin and / or hair that is preferably not based on IniPetition 870170023194, of 04/07/2017, p. 6/150
    Tyrosinase addition.
    [0015] It has surprisingly been found that this objective can be achieved through the use of compounds of formula (I) or a cosmetically acceptable salt thereof of a compound of formula (I) or a mixture containing two or more of these compounds or their salts
    where [0016] R1 denotes hydrogen or an organic radical having 1 to 14 carbon atoms, [0017] R2 denotes an organic radical having 1 to 14 carbon atoms, and
    [0018] in which, optionally, R1 and R2 are covalently linked to each other, preferably, so that a 3- to 8-membered ring is formed, [0019] for whitening the skin and / or hair.
    [0020] The compounds of formula (I) show pronounced skin and / or hair lightening effects. Therefore, the invention relates to cosmetic or pharmaceutical preparations (compositions) which contain a correspondingly effective amount of one or more compounds of formula (I), in particular, for topical lightening of the skin and / or hair.
    [0021] The compounds of formula (I) structurally belong to the group of menthyl carbamates.
    [0022] As common in the art, a flat structural formula, this
    Petition 870170023194, of 04/07/2017, p. 7/150
    5/135 is, a graphic formula that does not transmit any stereochemical information and does not give any concrete information about its three-dimensional structure, refers to and includes all the stereoisomers of the structural formula. For the sake of clarity, menthyl-carbamates of the flat structural formula (I) thus include all stereoisomeric forms thereof, namely, menthyl-, neomentyl-, isomentile neoisomentyl-carbamates, including their enantiomeric forms, such as explained in detail below.
    [0023] The compounds according to the invention of formula (I) exist in different isomeric forms and can be used in the context of the present invention, in all its isomeric forms, that is - depending on their structure - as enanciomers, diastereomers , sin- / anti-isomers, cis- / trans-isomers, epimers as well as (E) / (Z) -isomers. The compounds of formula (I) can be used in the context of the present invention, in the form of pure stereoisomeric form or in the form of a mixture of stereoisomers. The compounds of formula (I) can also be used in the context of the present invention in the form of pure enanciomers or in the form of a mixture of enanciomers, in the latter case, racemates being preferred.
    [0024] The menthyl carbamates of formula (I) are derived from 2isopropyl-5-methylcyclohexanol (p-menthane-3-ol), which has three asymmetric carbon atoms in its cyclohexane ring and occurs as four pairs enanciomers.
    [0025] These isomers can be illustrated by the following formulas, showing an enanciomer of each of the four diastereomers.
    Petition 870170023194, of 04/07/2017, p. 8/150
    6/135
    ΌΗ
    ΟΗ (-) - Menthol (Ha) (+) - neomenthol (llb)
    OH
    ΌΗ (+) - lsomentol (llc) (+) - Neoisomentol (lld) [0026] The enanciomers (lia) to (ll-D) and their optical antipodes can, for example, be obtained by hydrogenation of thymol (for example , WO 2004/018398, and the references cited therein) or by citronellal cyclization to the corresponding isopulegol-isomers and subsequent hydrogenation. The isomers of menthol can be separated by distillation needs (for details on the generation and separation of isomers of menthol see Common Fragrance and Flavor Materials, 4th edition, Wiley-VCH, Weinheim , 2001, 52-55).
    [0027] Structurally derived from the enanciomers (lia) to (ll-D) and their optical antipodes are the following compounds of formula (I). Compounds (Ia) are derived from (-) - menthol (lia), compounds (ent-la) are derived from (+) - menthol, compounds (Ib) are derived from (+) -neomentol (llb), the compounds (ent -Ib) are derived from (-) - neomenthol and so on.
    (ent) (ia)
    Petition 870170023194, of 04/07/2017, p. 9/150
    7/135
    (ld) (ent-ld) [0028] where R1 and R2 in each formula (Ia), (ent-it), (Ib), (ent-lb), (Ic), (ent-lc), ( ld) and (ent-ld) mutually and independently have the (preferred) meaning here above or below.
    [0029] As common in the art, in the context of the present invention, abbreviations for certain chemical groups are used, for example Me = methyl, Et = ethyl, Pr = propyl, Bu = butyl, Ph = phenyl.
    [0030] Various menthol carbamates of formula (I) have been described in the prior art.
    [0031] EP 2 135 516 discloses various neomenthyl carbamates as umami flavoring substances, inter alia the following:
    Petition 870170023194, of 04/07/2017, p. 10/150
    8/135
    [0032] WO 2004/000023 describes the following l-menthyl carbamates as insect repellents:

    [0033] J. Org. Chem. 1999, 7921 - 7928 discloses -, Ν-diethyl carbamate of (-) - (1 R) -mentyl:
    Petition 870170023194, of 04/07/2017, p. 11/150
    9/135 [0034] Polish Journal of Chemistry (1996), 70 (3), 310-19 describes
    [0035] Advanced Sinthesis & Catalysis (2008), 350 (9), 1235-1240 and Organic & Biomolecular Chemistry (2005), 3 (15), 2741-2749 disclose benzyl-carbamic acid (1R, 2S, 5R) / cycle -hexyl ester, respectively (1 S, 2R, 5S) -2-isopropyl-5-methyl-

    [0036] US 5,703,123 discloses the following formula that does not carry any stereochemical information:
    [0037] DE 1300725 discloses the following carbamate without including any stereochemical information:
    [0038] US 6,150,415 discloses the following carbamate without including any stereochemical information:
    Petition 870170023194, of 04/07/2017, p. 12/150
    10/135 [0039] Angewandte Chemie (1982), 94 (9), 709-710 describes all eight different enanciomers of 2-isopropyl-5-methyl-cyclohexyl ester of isopropyl-carbamic acid:
    [0040] WO 2004/033422 refers to compounds that inhibit fatty acid amide hydrolase (FAAH). The methods are described herein to control appetite and to clear appetite disorders by administering FAAH inhibitors, thereby reducing body fat or body weight. WO 2004/033422 discloses a very broad generic chemical formula of carbamates which also cover a large number of substituted or unsubstituted cycloalkyl carbamates. No menthyl carbamate is explicitly disclosed.
    [0041] EP 1 284 145 describes the use of N-2- (3,4-dihydroxyphenyl) -ethyl-substituted carbonic acid derivatives as radical scavengers and antioxidants. EP 1 284 145 further describes cosmetic preparations containing said carbonic acid derivatives. The effect of these compounds on the fat cell metabolism or body weight of humans has not been investigated here. The compound only explicitly mentioned in EP 1 284 145 of relevance in the formula (I) mode of the present invention is N [2 - (3,4-dihydroxyphenyl) -ethyl-O- (1R, 3R, 4S) -mentyl] carbamate. According to EP 1 284 145, cosmetic or dermatological preparations may additionally comprise skin lightening substances, for example, kojic acid, hydroquinone or Arbutin are mentioned.
    [0042] In a preferred embodiment, a cosmetic or pharmaceutical preparation according to the present invention is free of N- [2 (3,4-dihydroxyphenyl) -ethyl-O- (1R, 3R, 4S) -mentyl] carbamate. In another
    Petition 870170023194, of 04/07/2017, p. 13/150
    11/135 preferred embodiment, the compounds of formula (I) according to the present invention, more specifically, the compounds of formula (Ia), are excluded, in which R2 represents a group 2 (3,4-di- hydroxyphenyl) -ethyl - radical. In another preferred embodiment, the cosmetic or pharmaceutical preparations according to the present invention are free of compounds of formula (I) according to the present invention, more specifically, free of compounds of formula (Ia), wherein R2 represents a group 2 - (3,4-dihydroxyphenyl) -ethyl radical.
    [0043] WO 01/98235 describes the use of N-3, 4-didihydroxybenzyl-substituted carbonic acid derivatives as radical scavengers and antioxidants. WO 01/98235 further describes cosmetic preparations containing said carbonic acid derivatives. The effect of these compounds on fat cell metabolism or the body weight of humans has not been investigated here. The only compound mentioned explicitly in WO 01/98235 of relevance in the formula (I) mode of the present invention is N- (3,4dihydroxybenzyl) -O- (1 R, 3R, 4S) -mentyl] carbamate. According to WO 01/98235, cosmetic or dermatological preparations may additionally comprise skin lightening substances, for example, kojic acid, hydro-quinone or Arbutin are mentioned. [0044] In a preferred embodiment, a cosmetic or pharmaceutical preparation according to the present invention is free of N- (3,4dihydroxybenzyl) -O- (1 R, 3R, 4S) -mentyl] carbamate. In another preferred embodiment, the compounds of formula (I) according to the present invention, more specifically, the compounds of formula (Ia), are excluded, wherein R2 is a 3,4-dihydroxybenzyl radical. In another preferred embodiment, the cosmetic or pharmaceutical preparations according to the present invention are free from compounds of formula (I) according to the present
    Petition 870170023194, of 04/07/2017, p. 14/150
    12/135 invention, more specifically, free of compounds of formula (la), wherein R2 represents a 3,4-dihydroxybenzyl radical.
    [0045] In a preferred embodiment, compounds of formula (I) according to the present invention, more specifically, compounds of formula (la), are excluded, in which R2 represents a radical containing a 3,4- dihydroxyphenyl - group. In another preferred embodiment, the cosmetic or pharmaceutical preparations according to the present invention are free from compounds of formula (I) according to the present invention, more specifically, free from compounds of formula (la), where R2 represents a radical containing a 3,4-dihydroxyphenyl - group.
    [0046] In another preferred embodiment, compounds of formula (I) according to the present invention, more specifically, compounds of formula (la), are excluded, in which R2 represents a radical containing a dihydroxyphenyl - group. In another preferred embodiment, the cosmetic or pharmaceutical preparations according to the present invention are free from compounds of formula (I) according to the present invention, more specifically free from compounds of formula (la), wherein R2 represents a radical containing a dihydroxyphenyl - group.
    [0047] There is no indication that, so far, the compounds used according to the present invention are suitable for cosmetic or therapeutic skin and / or hair lightening.
    [0048] In the context of the present invention, a cosmetic use or a cosmetic method is free of any therapeutic (side) effects.
    [0049] In the context of the present invention, a therapeutic or pharmaceutical use or method is considered as a medical whitening, optionally with cosmetic (side) effects.
    [0050] The compounds according to the invention of formula (I), of Petition 870170023194, of 07/04/2017, p. 15/150
    13/135 depending on their structure, they can exist in different stereoisomeric forms, and can be used in the context of the present invention, in the form of stereoisomers, enanciomers, diastereomers, syn- / anti-isomers, endo- / exisomers, cis- / trans -isomers or epimers. The compounds of formula (I) can be used in the context of the present invention, in the form of cis- or trans-pure, syn- or antidiastereomeric acid or in the form of a mixture of diastereomers. The compounds of formula (I) can also be used in the context of the present invention in the form of pure enanciomers or in the form of a mixture of enanciomers, in the latter case, racemates being preferred.
    [0051] In the case R1 does not denote hydrogen R1 and R2 independently of each other preferably denote an optionally substituted radical selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, cycloalkylalkyl, alkenyl, cycloalkenyl, cycloalkylalkyl, alkynyl, cycloalkylalkyl, aryl, heteroaryl , arylalkyl, cycloalkylaryl, cycloalkylaryl, cycloalkyletheroaryl, heterocycloalkylaryl, heterocyclealkylaryl, heterocyclealkylethylaryl and heteroarylalkyl.
    [0052] In the case R1 does not denote hydrogen R1 and R2 independently of one another more preferably denote an optionally substituted radical C1-C14-alkyl, C1-C14-heteroalkyl, C3-C14cycloalkyl, C4-C14-cycloalkylalkyl, C2-C14-alkenyl , C3-C14cycloalkenyl, C4-C14-cycloalkylalkyl, C2-C14-alkynyl, C5-C14cycloalkylalkynyl, C3-C14-aryl, C2-C14-heteroaryl, C4-C14arylalkyl, C8-C14-cycloalkyl, C8-cycloalkylyl, C8-cycloalkyl, -C14cycloalkyletheroaryl, C8-C14-heterocycloalkylaryl, C8-C14heterocycloalkylaryl, C8-C14-heterocycloalkylethylaryl and C3-C14heteroarylalkyl.
    [0053] Radicas heteroalkyl, heteroaryl, cycloalkyletheroaryl, hePetition 870170023194, of 07/04/2017, p. 16/150
    14/135 terocycloalkylaryl, heterocycloalkylaryl, heterocycloalkylethylaryl and heteroarylalkyl in the context of the present invention preferably contain at least one heteroatom, optionally up to four heteroatoms, selected independently from the group consisting of O, S and / or N. Preferred are heteroalkyl, heteroaryl radicals, cycloalkyletheroaryl, heterocycloalkylaryl, heterocycloalkylaryl, heterocycloalkylyloaryl and heteroarylalkyl containing one, two or three heteroatoms, selected independently from the group consisting of O, S and / or N.
    [0054] In preferred compounds of formula (I), R1 denotes hydrogen. In other investigations, compounds of formula (I) in which R1 denotes hydrogen have generally been found to have good to excellent activity and effectiveness in relation to skin and / or lightening.
    [0055] In preferred compounds of formula (I), R2 denotes an organic radical having 1 to 12 carbon atoms, preferably an organic radical having 1 to 10 carbon atoms, more preferably an organic radical having 1 to 8 carbon atoms.
    In more preferred compounds of formula (I), R2 denotes an optionally substituted radical C1-C10-alkyl, C1-C10-heteroalkyl, C3C10-cycloalkyl, C4-C10-cycloalkylalkyl, C2-C10-alkenyl, C3-C10cycloalkenyl, C4- C10-cycloalkylalkyl, C2-C10-alkynyl, C5-C10cycloalkylalkynyl, C3-C10-aryl, C2-C10-heteroaryl, C4-C10arylalkyl, C8-C10-cycloalkylyl, C8-C10-cycloalkylyl, C5-C10-C10-C10 heterocycloalkylaryl, C8-C10heterocycloalkylaryl, C8-C10-heterocycloalkylethylaryl and C3-C10heteroarylalkyl.
    [0056] In even more preferred compounds of formula (I), R2 denotes an optionally substituted radical chosen from the group consisting of C1-C8-alkyl, C3-C8-cycloalkyl, C4-C12cycloalkylalkyl, C2-C8-alkenyl, C3 -C8-cycloalkenyl, C4-C8Petition 870170023194, of 04/07/2017, p. 17/150
    15/135 cycloalkylalkyl, C3-C8-aryl, C2-C8-heteroaryl, C4-C8-arylalkyl, C5-C8-cycloalkyletheroaryl and C4-C8-heteroarylalkyl.
    [0057] If the radicals R1 and / or R2 are substituted, R1 and / or R2 each may contain one or more heteroatoms, preferably and independently selected from the group consisting of O, S, N, Si and F. If the heteroatoms are selected from the group consisting of O, S and N, the radicals R1 and / or R2 each preferably contain one, two or three heteroatoms independently selected from the group consisting of O, S and / or N.
    [0058] If the radicals R1 and / or R2 are substituted the following substituents are preferred:
    [0059] hydroxyl, [0060] fluoride, [0061] C1-C8-alkyl, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, tert-butyl, [0062] C3-C12-cycloalkyl , preferably cyclopropyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclododecyl, [0063] C2-C8-alkynyl, preferably ethynyl, propynyl, [0064] C1-C8-perfluoroalkyl, preferably trifluoromethyl, nonafluorobutyl, [0065] C1-C1-8 alkoxy , preferably methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, iso-butoxy, tert-butoxy, [0066] C3-C8-cycloalkoxy, preferably C3-cycloalkoxy, C5cycloalkoxy, C6-cycloalkoxy, C8-cycloalkoxy, C8-cycloalkoxy ] C1-C10-alkoxyalkyl, where 1 to 3 CH2 groups are replaced by oxygen, preferably - [- O-CH2-CH2-] vQ or - [- O-CH2CHMe-] vQ, where Q is OH or CH3 and where v denotes an integer from 1 to 3, [0068] C1-C4-acyl, preferably acetyl, [0069] C1-C4-acetal, preferably dimethylacetal group, diethylacePetition 870170023194, 07/04/2017, pg . 18/150
    16/135 such or methylenedioxy -O-CH2-O-.
    [0070] C1-C4-carboxyl, preferably CO2Me, CO2Et, CO2isoPr, CO2terc-Bu, [0071] C1-C4-acyloxy, preferably acetyloxy, [0072] Si1-Si10-silyl, and [0073] Si1-Si30-siloxy or polysiloxy.
    [0074] Preferred cosmetic or pharmaceutically acceptable salts of compounds of formula (I) are those in which the one or more counterions (cation and counteraction) are selected from the group consisting of Na +, K +, NH4 +, trialkylammonium NHRÍ3 +, Ca2 + , Mg2 +, Zn2 + and AI3 +.
    [0075] In trialkylammonium NHR3 +, preferably each R1 independently of the other radicals R1 denotes an alkyl group having 1 to 30 C-atoms, preferably having 4 to 22 C-atoms.
    [0076] Particular preferred counterions are Na +, K +, NH4 +, Ca2 + and / or Mg2 +.
    [0077] If two different compounds of formula (I) are used as a mixture, generally the weight ratio of the two compounds is chosen in the range from 10: 1 to 1: 10, preferably in the range from 5: 1 to 1: 5, more preferably in the range from 3: 1 to 1: 3, the counterion, if present, is not included in the case of salts.
    [0078] In the context of the present invention, a wavy line in the structural formulas means that the double bond can be in the (E) or (Z) configuration.
    [0079] Preferred compounds of formula (I) are chosen where NR2 is a radical chosen from the following list N:
    Petition 870170023194, of 04/07/2017, p. 19/150
    17/135
    '' N yy ^ -N THE 1 2 3 4 5 6 7 The I yxx ^ N 0- N 9 10 11 12 /yxy.j Υ ^ Ν y ^ - N yyx ^ y ^ N 13 14 15 16 ’^ 'Ν X 17 18 19 20 ΑΑ THE 21 22 23 24
    Petition 870170023194, of 04/07/2017, p. 20/150
    18/135
    The. Çl. xx. xx. 25 26 27 20 V- THE· φ .. çx. 29 30 31 32 XX. THE 33 34 The. Ϋ · Xx. Ό. 35 36 37 38 THE φ. ÇC. 39 40 41 42
    Petition 870170023194, of 04/07/2017, p. 21/150
    19/135
    X Λ. 43 44 CL · ÇL · XX- XX- 45 45 47 46 jÇL · ÇL · Í ^ L · ÇC $ 4 50 51 52 XX- X. 53 54 CL · ÇL · XV 55 56 57 56 cjx. çc 59 60 61 62
    Petition 870170023194, of 04/07/2017, p. 22/150
    20/135
    SHAH 63 64 TjO 65 66 67 68 qN qN QN Q. 69 70 71 72 9 ·.OMe n ΜβθΆΑχ Ν Me0 'v ^ 1 XX. 73 74 75 JQ,OMe Ό.OMe XOMe g.OMe 76 77 78 79 MeO ^ p ^ N ΊΓχ MeO '> A í < ' N MeO ^^^ N jCXMeO ^ A 80 81 82 83
    Petition 870170023194, of 04/07/2017, p. 23/150
    21/135
    Μή “Χς 64 85 86 X THE THE THE 67 88 89 90 HERE x-- 0 C ax 91 92 93 94 0 ζ ^ ο ΛαΑ · ' ÇV Oy Oy 95 96 97 98 cv. THE The. 99 100 101 102 V. air CNThe. Ά 103 104 105 106 V Αχ / Ά 1 O-ύ 107 100 109 110
    Petition 870170023194, of 04/07/2017, p. 24/150
    22/135
    The; The or 111 112 113 114 , NHO '' δ 115 116 117 113 -Ay ay / NXV Y 119 120 121 122 .OHOver there O A o - N ΥΛ 123 124 125 126 Y- Yv 127 126 129 130 Y Y Α ν '0' ^ χ - χΛ 'Ν «Y 131 132 133 134 JÇ h <A-— N „ The V ^ the YnY 135 136 137 138
    0— N h 0 L ^ N > / L, n 139 140 141 142 HO Y ^ sky X. Y 143 144 145 146 Y IVThe" Y ΗΟ '^ γ ^ ΑN 147 148 149 150 ç. V N 151 152 153 154
    Petition 870170023194, of 04/07/2017, p. 25/150
    Preferred adicoinal compounds of formula (I) are chosen from formula (Ia) in which R1 denotes hydrogen and where NR2 of formula (I) denotes a radical selected from the list N, above. [0081] Preferred adicoinal compounds of formula (I) are chosen from formula (ent-it) where R1 denotes hydrogen and where NR2 of formula (I) denotes a radical selected from the list N, above.
    [0082] Preferred adicoinal compounds of formula (I) are chosen from formula (Ib) where R1 denotes hydrogen and where NR2 denotes formula (I) denotes a radical selected from the list N, above. [0083] Preferred adicoinal compounds of formula (I) are chosen from formula (ent-lb) where R1 denotes hydrogen and where NR2 of formula (I) denotes a radical selected from the list N, above.
    [0084] Other preferred compounds of formula (I) are chosen from formula (Ic) in which R1 denotes hydrogen and where NR2 of formula (I) denotes a radical selected from the list N, above.
    [0085] Other preferred compounds of formula (I) are chosen from formula (ent-lc) where R1 denotes hydrogen and where NR2 denotes formula (I) denotes a radical selected from the list N, above. [0086] Other preferred compounds of formula (I) are chosen from formula (Id) in which R1 denotes hydrogen and in which NR2 of formula (I) denotes a radical selected from the list N, above.
    [0087] Other preferred compounds of formula (I) are chosen from formula (ent-ld) where R1 denotes hydrogen and where NR2 denotes formula (I) denotes a radical selected from the list N, above. [0088] However, in the context of the present invention, and depending on the circumstances, each individual compound of the preferred compounds of formula (I) identified above where R1 denotes hydrogen and where NR2 is the radical chosen from the list N, above, can by raPetition 870170023194, from 04/07/2017, p. 26/150
    24/135 technical and non-technical variations, depending on the case may be, in some embodiments, more preferred or less preferred than other preferred compounds. Thus, in some cases the compounds do not necessarily share the same level of preference.
    [0089] Other preferred compounds of formulas (I) are chosen where NR1R2 is the radical chosen from the following list D:
    'X '' 'Ά AA 201 202 203 204 HERE V k N ^ Y A ^ 205 206 207 208 aY 209 210 211 212 Α ^ γ THE ^ A-Y 213 214 215 216 / Y ' ΧΧγ 217 218 219 220 -Α / γ THE- THE- AY 221 222 223 224 Υχγ THE-- γΥ 225 226 227 228 O O OTHE THE 229 230 231 232
    Preferred adicoinal compounds of formula (I) are chosen from formula (Ia) where NR1R2 is the radical chosen from list D, above.
    [0091] Preferred adicoinal compounds of formula (I) are chosen from formula (ent-it) where NR1R2 is the radical chosen from list D, above.
    Petition 870170023194, of 04/07/2017, p. 27/150
    Preferred adicoinal compounds of formula (I) are chosen from formula (Ib) where NR1R2 is the radical chosen from list D, above.
    [0093] Preferred adicoinal compounds of formula (I) are chosen from formula (ent-lb) where NR1R2 is the radical chosen from list D, above.
    [0094] Other preferred compounds of formula (I) are chosen from formula (Ic) where NR1R2 is the radical chosen from list D, above.
    [0095] Other preferred compounds of formula (I) are chosen from formula (ent-lc) where NR1R2 is the radical chosen from list D, above.
    [0096] Other preferred compounds of formula (I) are chosen from formula (Id) where NR1R2 is the radical chosen from list D, above.
    [0097] Other preferred compounds of formula (I) are chosen from formula (ent-ld) where NR1R2 is the radical chosen from list D, above.
    However, in the context of the present invention, and depending on the circumstances, each individual compound of the preferred compounds of formula (I) indicated above where NR1R2 is a radical chosen from list D, above, may for technical reasons or non-technical, as the case may be, in some embodiments being more preferred or less preferred than other preferred compounds. Thus, in some cases, the compounds do not necessarily share the same level of preference.
    [0099] Due to their good excellent activity and effectiveness in relation to the effects to be achieved within the scope of the present invention, the preferred compounds of formula (I) according to the present invention are selected from the group consisting of:
    Petition 870170023194, of 04/07/2017, p. 28/150
    26/135
    Petition 870170023194, of 04/07/2017, p. 29/150
    27/135

    [00100] Due to their high activity in relation to the effects to be achieved within the scope of the present invention, the even more preferred compounds of general formula (I) according to the present invention are selected from the group consisting of:
    Petition 870170023194, of 04/07/2017, p. 30/150
    28/135
    [00101] Of said compounds, those corresponding to the formulas (la), (ent-la), (Ib) or (ent-lb) or a racemic mixture of these are particularly preferred.
    [00102] Various compounds of formula (I), in particular, the preferred compounds according to the present invention, are identified and designated according to an arbitrary internal reference numbering system type BIO, followed by a four digit number 870170023194, of 04/07/2017, p. 31/150
    29/135 tos.
    [00103] Particularly preferred menthol carbamates of formula (I) are as follows:
    Number ofreference Chemical name Structure BIO1151 (1 R, 2S, 5R) -2-isopropyl-5-methyl-ethylhexyl cyclohexyl estercarbamic I f 0 I <* ON H BIO1378 (1 S, 2R, 5S) -2-isopropyl-5-methyl-cyclohexyl ester of ethylcarbamic I | 0 H BIO1461 (1 S, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of ethylcarbamic IA AThe NH BIO1155 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl acid ester (3-methoxy-propyl) -carbamic I0X ίΟ Ν ΟΗ BIO1339 (1 S, 2R, 5S) -2-isopropyl-5-methyl-cyclohexyl acid ester (3-methoxy-propyl) -carbamic acid I Ί π | 0 Μ ° BIO1460 (1 S, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl acid ester (3-methoxy-propyl) -carbamic acid I [I 9 ΟΝ Ο Η X BIO1267 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of butyl acidcarbamic I ο χ II Ο Ν Η
    Petition 870170023194, of 04/07/2017, p. 32/150
    30/135
    Number ofreference Chemical name Structure BIO1268 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl acid ester (3-isopropoxy-propyl) -carbamic I l, 0 I ONO H BIO1271 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of He-xyl-carbamic I I ° X O 'N H BIO1159 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl acid esterIsobutyl-carbamic I[L °The NH BIO1301 (1 S, 2R, 5S) -2-isopropyl-5-methyl-cyclohexyl ester of methanoltil-carbamic r í ° lld | 0 « BIO1571 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of benign acidzo [1,3] dioxol-5-ylmethyl-carbamic I 0 X 1 N Tl - '~ -r °. H 11 1 „>'r' o BIO1580 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of phenyl acidcarbamic ZIO_ BIO1185 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of methanoltil-carbamic 1ONH
    Petition 870170023194, of 04/07/2017, p. 33/150
    31/135
    Number ofreference Chemical name Structure BIO1336 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl acid ester (2-methoxy-ethyl) -carbamic ILx o- The NHΛ BIO1662 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl acid ester (6-hydroxy-hexyl) -carbamic II 'OHThe NH BIO1699 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of cyclohexyl acidhexylmethyl-carbamic ToX ° Vtq BIO1702 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl acid ester (te-trahidro-furan-2-ilmetil) -carbamic Λ ° BIO1266 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of cyclohexyl acidhexyl-carbamic ÓAX Vx. H BIO1632 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl acid ester (2-ethoxy-phenyl) -carbamic òx Λ H V BIO1633 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl acid ester (2-acetyl-phenyl) -carbamic
    Petition 870170023194, of 04/07/2017, p. 34/150
    32/135
    Number ofreference Chemical name Structure BIO1695 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of benign acidzyl-carbamic ToA ° BIO1553 (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of diethyl acidcarbamic ΑοΑγ-
    [00104] The (preferred) compounds of formula (I), in particular those explicitly listed above, were particularly active with respect to the effects to be achieved within the scope of the present invention. [00105] The following compounds of formula (I) are particularly preferred since they are among the most active and effective compounds tested:
    BIO1151, BIO1571, BIO1266, BIO1460, BIO1461,
    BIO1580, BIO1632, BIO1633, BIO1695, BIO1699, BIO1155, BIO1553 and BIO1185.
    [00106] The compounds of formula (I) of the present invention can generally be obtained by processes well known in chemical synthesis. For example, the reaction of
    on what
    Petition 870170023194, of 04/07/2017, p. 35/150
    33/135 [00107] R1 and R2 denote a (preferred) radical, as defined above, preferably, R1 represents H, and Hal represents a halide, preferably chloride or bromide.
    [00108] In order to facilitate the dehydrohalogenation step and the formation of a compound of formula (I), it is preferred to carry out said reaction in the presence of a base, preferably a tertiary amine. Preferred compounds of formula (I) in which R1 represents H can preferably be obtained by reacting menthol with a corresponding isocyanate and O = C = N-R2, as shown in the following reaction scheme:
    OH
    O = C = N — R (I) [00110] where R2 represents a (preferred) radical, as defined here above.
    [00111] The present invention also relates to the cosmetic or pharmaceutical (preferably topical) composition for whitening the skin and / or hair, comprising (a) one, two or more (preferably preferred) compounds of formula (I) , as defined herein and / or a cosmetic or pharmaceutically acceptable salt thereof, preferably in an amount that has a lightening effect on the skin and / or hair, and
    (b) one or more other active ingredients for adequate skin and / or hair lightening for cosmetic or pharmaceutical applications that are not compounds of formula (I), preferably in an amount that has a lightening effect on the skin and / or the hair.
    [00112] Thus, in a cosmetic (preferably topical) composition, Petition 870170023194, of 04/07/2017, p. 36/150
    34/135 ca or pharmaceutical according to the present invention for whitening skin and / or hair the amount of one, two or more compounds (preferably preferred) of formula (I) as defined herein (component (a), above ) alone and / or the amount of one or more other active ingredients for skin and / or hair lightening (component (b), above) alone may not be sufficient to exhibit a skin lightening effect and / or hair. However, the total amount, i.e. the amount, of components (a) and (b) in a composition according to the present invention is sufficient to exhibit a lightening effect on the skin and / or hair.
    [00113] As already indicated above, in preferred embodiments, the amount of one, two or more compounds (preferably preferred ones) of formula (I) as defined herein (component (a), above) alone and / or a amount of one or more other active ingredients for lightening the skin and / or hair (component (b), above) alone in a composition according to the present invention are sufficient to have a lightening effect on the skin and / or the hair.
    [00114] A composition (preparation), preferably a topical composition, according to the present invention preferably contains one or more compounds of formula (I) (including all stereoisomers, enanciomers, diastereomers, cis / transisomers and epimers , without considering possible counterions) in a total amount of 0.001 - 30% by weight, more preferably 0.01 - 20% by weight, even more preferably 0.01 - 5% by weight, particularly preferably 0.05 - 3% by weight and more preferably 0.1-2% by weight, in each case, based on the total weight of the preparation (composition).
    [00115] In the context of the present invention, an effective amount of compounds (preferred ones) of formula (I) refers to an amount
    Petition 870170023194, of 04/07/2017, p. 37/150
    35/135 total of one, two or more compounds (preferred) of formula (I) having a lightening effect on human skin and / or human hair.
    [00116] The compounds of formula (I) can be easily incorporated in these common concentrations cosmetic or dermatological formulations (preparations) such as pump sprayers, aerosol sprayers, creams, ointments, tinctures, lotions and the like. [00117] Cosmetic, dermatological or pharmaceutical preparations according to the invention can be produced by conventional processes known per se, such that one or more compounds of formula (I) are incorporated into cosmetic (topical), dermatological or pharmaceutical products which can have a conventional composition and which, in addition to the effects mentioned above or below, can also be used for lightening, care and cleaning of the skin or hair.
    [00118] For use, topical, dermatological or pharmaceutical cosmetic preparations according to the invention, or for use according to the invention comprising formula (I) are generally applied to the skin and / or hair in a sufficient amount of a conventional form for topical cosmetics, dermatological products or pharmaceuticals.
    [00119] As indicated above, no mention or suggestion is made in the prior art, of a cosmetic or therapeutic use of compounds of formula (I) as skin and / or hair lightening agents or of compounds of formula (I) having depigmentation action.
    [00120] One area of application in this regard is the therapeutic whitening of melanin-induced pigmentation disorders such as hyperpigmentations (e.g., scar hyperpigmentations, hyperpigmentation caused by post-traumatic drug, hyperpigmentationPetition 870170023194, 07/04/2017, page 38/150
    36/135 post-inflammatory reactions induced by phototoxic reactions, ephelids). [00121] A cosmetic or pharmaceutical preparation, preferably topical, according to the present invention preferably contains, as component (b) one or more active ingredients for whitening the skin and / or hair selected from the group consisting of :
    [00122] kojic acid (5-hydroxy-2-hydroxymethyl-4-pyranone), kojic acid derivatives, preferably kojic acid dipalmitate, Arbutin, ascorbic acid, ascorbic acid derivative, preferably magnesium ascorbyl phosphate, hydroquinone, derivatives hydroquinone, resorcinol, resorcinol derivatives, preferably 4-alkylresorcinols and 4- (1-phenylethyl) 1,3-dihydroxybenzene (phenylethyl resorcinol), molecules containing sulfur, preferably glutathione or cysteine, alphahydroxy acids (preferably citric acid, acid lactic acid, malic acid), salts and esters thereof, N-acetyl tyrosine and derivatives, undecenoyl phenylalanine, gluconic acid, chromone derivatives, preferably aloesin, flavonoids, 1-aminoethyl phosphinic acid, thiourea derivatives, ellagic acid, nicotinamide (niacinamide ), zinc salts, preferably zinc chloride, tujaplicin and derivatives, triterpenes, preferably maslinic acid, sterols, preferably ergosterol, benzofuranones, preferred senquiunolide, vinyl tabol, ethyl tabol, dionic acids, preferably dionic octodecene acid and / or zelaic acid, nitrogen oxide synthesis inhibitors, preferably L-nitroarginine and derivatives thereof, 2,7-dinitroindazole or thiocitrulin, metal chelators ( preferably alpha hydroxy fatty acids, phytic acid, humic acid, bile acid, bile extracts, EDTA, EGTA and derivatives thereof), retinoids, soy milk and extract, serine protease inhibitors or lipoic acid or other natural active ingredients or synthetic to lighten the skin or hair, the latter preferably in the form of a plant extract, preferably bearberry stratum,
    Petition 870170023194, of 04/07/2017, p. 39/150
    37/135 rice extract, papaya extract, tumor extract, blackberry extract, bengkoang extract, tiriricatiririca extract, licorice root extract or concentrated or isolated constituents thereof, preferably glabridine or licocalcona A, artocarpus extract, extract of rumex and ramulus species, extracts of pine species (pinus), extracts of vitis species or stilbene derivatives isolated or concentrated therefrom, extract of saxifragaceae, extract of and / or grape extract.
    [00123] Skin whitening preferred as component (b) are kojic acid, phenylethyl resorcinol, beta- and alpha-Arbutin, hydroquinone, nicotinamide, dioic acid, ascorbyl magnesium phosphate and vitamin C and its derivatives, blackberry extract, bengkoang extract, papaya extract, turmeric extract, tiriricatiririca extract, licorice extract (containing glycyrrhizin), alpha-hydroxy acids, 4-alkylresorcinols, 4-hydroxyanisole. These skin lighteners are preferred because of their very good activity, in particular in combination with one or more of the preferred or particularly preferred compounds of formula (I) according to the present invention. In addition, preferred skin lighteners are readily available.
    [00124] The skin and / or hair lightening activity of compounds of formula (I) is not based on tyrosinase inhibition.
    [00125] A cosmetic or pharmaceutical preparation, preferably topical, according to the invention containing one or more active ingredients for the lightening of the skin and / or hair selected from the aforementioned group of component (b) allows to obtain an action of more pronounced skin and / or hair whitening which is at least partially based on synergistic effects.
    [00126] The preparations according to the present invention, including (a) one or more compounds of formula (I) and (b) one or more tyrosinase inhibitors have been shown to exhibit particularly better activityPetition 870170023194, of 07/04/2017, p. 40/150
    38/135, in particular, faster and / or stronger, based on the modulation of two independent cellular mechanisms. In many cases, more than an additive, often synergistic whitening efficacy has been observed.
    [00127] Thus, in a preferred embodiment, preparations, preferably cosmetic preparations, according to the invention containing one or more compounds of formula (I), preferably comprise one or more active ingredients for whitening the skin and / or tyrosinase inhibitors.
    [00128] Preferred tyrosinase inhibitors are selected from the group consisting of kojic acid and resorcinol derivatives to lighten the skin and / or hair, preferably 4-alkylresorcinols, in particular 4-C3-C8-alkylresorcinols, and 4 - ( 1-phenylethyl) 1,3-dihydroxybenzene.
    [00129] The total amount of component (b), that is, the total amount of one or more other active ingredients for whitening the skin and / or hair suitable for cosmetic or pharmaceutical application that are not compounds of formula (I), preferably selected from the aforementioned (preferred) group of other active ingredients for whitening skin and / or hair in the preparations according to the invention, it is preferably in the range from 0.0130% by weight, plus preferably in the range from 0.01 to 20% by weight, particularly preferably in the range from 0.01 to 5% by weight, in each case, based on the total weight of the preparation. [00130] In the context of this text, in the case of a substance having the properties of skin and / or hair as well as one or more additional properties selected from the group consisting of antioxidants, anti-inflammatories, anti-irritants and / or exfoliating properties, the substance is considered to be a skin and / or hair whitening component (b), in particular for assessments
    Petition 870170023194, of 04/07/2017, p. 41/150
    39/135 quantitative.
    [00131] For use in the conventional form for cosmetics and pharmaceuticals, the compounds of formula (I) are applied on the skin and / or hair in an appropriate amount. Particular advantages are offered here for cosmetic and dermatological preparations that contain one or more compounds of formula (I) and, in addition, function as a means of sun protection, providing a preparation that protects hair and / or skin from ultraviolet radiation. [00132] Particular advantage are cosmetic, dermatological and / or pharmaceutical preparations, according to the invention, which additionally includes one or more sunscreens (UV absorbers, UV filters) and which thus act as the whitening agent skin and / or smoothing age spots and a sunscreen reducing agent.
    [00133] The preparations according to the invention in the field of cosmetics and pharmaceutical products, which contain one or more compounds of formula (I), are advantageously combined with substances that absorb or reflect UV radiation, particularly for cosmetic or cosmetic purposes. skin protection. These preparations according to the present invention are particularly effective and beneficial in lightening the skin and / or hair, in particular the skin.
    [00134] Preferred cosmetic preparations according to the invention can also contain anti-inflammatory and / or active ingredients that improve redness and / or itching. The compounds mentioned in WO 2005/123101 are advantageously used as anti-inflammatory active ingredients or that improve redness and / or itching.
    [00135] In preferred anti-irritant embodiments, they are used in the preparations according to the present invention. These preparations according to the present invention are particularly effective and
    Petition 870170023194, of 04/07/2017, p. 42/150
    40/135 beneficial in lightening the skin and / or hair, in particular the skin.
    [00136] Anti-irritants, in this context, can be all active anti-inflammatory ingredients or active ingredients to relieve redness and itching that are suitable for or commonly used in cosmetic and / or therapeutic applications (for example dermatological). All substances that reduce the amount of histamine and cytokines, interleukins, in particular prostaglandins and / or leukotrienes in cells and tissues are preferred.
    [00137] Melanin production is often stimulated as a result of inflammation, a process called post-inflammatory hyperpigmentation. Skin insults that result in inflammation / irritation can induce post-inflammatory hyperpigmentation. Among such insults are acne lesions, ingrown hairs, scratches, insect bites and surfactant damage. One of the most common forms of post-inflammatory hyperpigmentation is tanning after exposure to sunlight in response to UV damage to the skin. Although, in the latter case, there may be no visible erythema, histologically, such exposed skin raised the inflammatory / irritant cell content, producing a subclinical inflammatory / irritant process. Thus, avoiding skin inflammation / irritation is beneficial in relation to the inhibition of melanogenesis in the skin.
    [00138] Preferred antioxidants, within the meaning of this text, are substances that reduce the amount of free radicals in cells and / or tissues. These preparations according to the present invention are particularly effective and beneficial in lightening the skin and / or hair, in particular the skin.
    [00139] Reactive oxygen species, such as superoxide and nitric oxide, generated on injured skin (for example, resulting from exposure to UV radiation) or released as a by-product from cellulite 870170023194, from 07/04/2017, page . 43/150
    41/135
    Inflammatory cells are known stimulators of melanogenesis in melanocytes. In such a case, it is important to maintain cellular redox by suppressing reactive oxygen species, and to increase anti-oxidant defenses to prevent melanogenesis.
    [00140] Thus, the preferred preparations, preferably cosmetic preparations, according to the invention containing one or more compounds of formula (I), preferably additionally contain
    - one or more agents selected from the group of substances that absorb or reflect UV radiation, preferably for cosmetic purposes, in particular for skin and / or hair protection purposes, and / or [00141] one or more agents selected from the group of anti-irritants and anti-inflammatories, and / or [00142] one or more agents selected from the group of anti-oxidants.
    [00143] The total amount of UV filter substances (UV absorbers) is advantageously in the range from 0.01% to 40% by weight, preferably in the range from 0.1% to 30%, in weight, more preferably in the range from 0.2 to 20% by weight, even more preferably in the range from 0.5% to 15% by weight, in particular in the range from 1.0 to 10.0 % by weight, in each case, based on the total weight of the preparation.
    [00144] The total amount of anti-irritants (one or more compounds) and anti-inflammatory substances (one or more compounds) in the preparations according to the invention is preferably 0.01 to 20% by weight, particularly preferably 0.03 to 10% by weight, in particular 0.05 to 5% by weight, based on the total weight of the preparation.
    [00145] The total amount of antioxidants (one or more compounds)
    Petition 870170023194, of 04/07/2017, p. 44/150
    42/135 in the formulations according to the invention is preferably 0.01 to 20% by weight, in particular preferably from 0.05 to 10% by weight, in particular 0.2 to 5% by weight, based on total formulation weight.
    [00146] These preparations advantageously contain at least one UVA filter and / or at least one UVB filter and / or at least one inorganic pigment, for a light protection factor (sun protection factor, SPF) of 2 or more ( preferably 5 or higher) is achieved.
    [00147] Advantageous UV filters and inorganic light protection pigments are mentioned in WO 2005/123101. UV absorbers particularly suitable for the combination are also mentioned in WO 2005/123101.
    [00148] Advantageously, these preparations contain at least one UVA filter and / or at least one UVB filter and / or at least one inorganic pigment. The preparations can be present here in various forms, such as those conventionally used for sun protection preparations. Thus, they can be in the form of a solution, a water-in-oil (W / O) or oil-in-water (O / W) emulsion or in a multiple emulsion, for example, water type -in-oil-in-water (W / O / W), a gel, a hydrodispersion, a solid stick, or an aerosol.
    [00149] In a further preferred embodiment a formulation according to the invention contains a total amount of sun protection agents, that is, in particular UV filters and / or inorganic pigments (filter pigments) such that the formulation according to the invention has a light protection factor greater than or equal to 2 (preferably greater than or equal to 5). Such formulations according to the invention are particularly suitable for the protection of skin and hair.
    Petition 870170023194, of 04/07/2017, p. 45/150
    The formulations according to the invention advantageously contain at least one UV-A filter and / or at least one UV-B filter and / or a broadband filter and / or at least one inorganic pigment. The formulations according to the present invention preferably contain at least one UV-B filter or a broadband filter, more particularly, preferably, at least one UV-A filter and at least one UV-B filter.
    [00151] Suitable UV filters are, for example, organic UV absorbers from the class comprising 4-aminobenzoic acid and its derivatives, salicylic acid derivatives, benzophenone derivatives, dibenzoylmethane derivatives, diphenyl acrylates, 3-imidazole-4-acid il acrylic and its esters, benzofuran derivatives, benzylidene malonate derivatives, polymeric UV absorbers containing one or more organosilicon radicals, cinnamic acid derivatives, camphor derivatives, triamilino-s-triazine derivatives, 2-hydroxyphenylbenzotriazole derivatives, derivatives of phenylbenzimidazole sulfonic acid and its salts, menthyl esters of anthranilic acid, derivatives of benzotriazoles, derivatives of indole.
    [00152] The compounds according to the invention, or for use according to the invention, having the formula (I) are particularly preferably combined with water-soluble UV filters, in a preferred embodiment with disodium salt of bis benzimidazyl acid tetrasulfonic acid (Neo Heliopan ® AP) and / or 2-phenylbenzimidazole sulfonic acid (Neo Heliopan ® Hydro).
    [00153] In addition, it is advantageous to combine the compounds of formula (I) with active ingredients that penetrate the skin and protect the skin cells from the inside against sun-induced damage, such as skin aging, skin inflammation and leather canêr. The respective ingredients, so-called aryl hydrocarbon receptor antagonists, are described in WO 2007/128723. Preferred is 2 Petition 870170023194, from 04/07/2017, p. 46/150
    44/135 benzylidene-5,6-dimethoxy-3,3-dimethylindan-1-one.
    [00154] The UV filters cited below that can be cited within the context of the present invention are preferred but of course not limiting.
    [00155] UV filters that are preferably combined with one or more compounds of formula (I) in a preparation according to the present invention are selected from the group consisting of • ethyl p-aminobenzoic acid • ethyl p-aminobenzoic acid ester ethoxylated ester (25 mol) (INCI name: PEG-25 PABA) • p-dimethylaminobenzoic acid-2-ethylhexyl ester • p-aminobenzoic acid ethyl ester (2 mol) N-propoxylated • glycerol p-aminobenzoic acid ester • homomentyl salicylic acid ester (homosalates) (Neo Heliopan®HMS) • 2-ethylhexyl salicylic acid ester (Neo Heliopan®OS) • triethanolamine salicylate • benzyl 4-isopropyl salicylate • anthranilic acid menthyl ester (Neo Heliopan®MA) • ethyl ester of diisopropyl cinnamic acid • 2-ethylhexyl ester of p-methoxycinnamic acid (Neo Heliopan®AV) • diisopropyl cinnamic methyl ester • isoamyl ester of p-methoxycinnamic acid (Neo Heliopan®E
    1000) • p-methoxykinnamic acid diethanolamine salt • isopropyl ester of p-methoxycinnamic acid • 2-phenylbenzimidazole sulfonic acid and salts (Neo Heliopan®Hidro)
    Petition 870170023194, of 04/07/2017, p. 47/150
    45/135 • 3- (4'-trimethylammonium) benzylidene bornan-2ona methyl sulfate • beta-imidazole-4 (5) -acrylic acid (urocanic acid) • 3- (4'-sulfo) benzylidene bornan-2-one and salts • 3- (4'-methyl benzylidene) -D, L-camfor (Neo Heliopan®MBC) • 3-benzylidene-D, L-camfor • N polymer - [(2 and 4) - [2- ( oxoborn-3-ildene) methyl] benzyl] acrylamide • 4,4 '- [(6- [4- (1,1-dimethyl) aminocarbonyl) phenylamino] -1,3,5triazine-2,4-diyl) diimino] -bis- (2-ethylhexyl benzoic acid ester) (Uvasorb®HEB) • benzylidene malonate polysiloxane (Parsol®SLX) • glyceryl ethylhexanoate dimethoxycinnamate • dipropylene glycol salicylate • tris (2-ethylhexyl) -4,4 ' , 4- (1,3,5-triazine-2,4,6triiltriimino) tribenzoate (= 2,4,6-trianilino- (p-carbo-2'-ethylhexyl-1 '-oxy) 1,3,5- triazine) (Uvinul®T150)
    Broadband filters that are preferably combined with one or more compounds of formula (I) in a preparation according to the present invention are selected from the group consisting of • 2-ethylhexyl-2-cyano-3,3- acrylate diphenyl (Neo Heliopan®303) • ethyl-2-cyano-3,3'-diphenyl acrylate • 2-hydroxy-4-methoxybenzophenone (Neo Heliopan®BB) • 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid • dihydroxy-4-methoxybenzophenone • 2,4-dihydroxybenzophenone • tetrahydroxybenzophenone
    Petition 870170023194, of 04/07/2017, p. 48/150
    46/135 • 2,2'-dihydroxy-4,4'-dimethoxybenzophenone • 2-hydroxy-4-n-octoxybenzophenone • 2-hydroxy-4-methoxy-4'-methyl benzophenone • sodium hydroxyethoxybenzophenone sulfonate • disodium-2,2'-dihydroxy-4,4'-dimethoxy-5,5'disulfobenzophenone • phenol, 2- (2H-benzotriazol-2-yl) -4-methyl-6- (2-methyl-3 (1,3,3,3tetramethyl-1 - (trimethylsiIi) oxy) disyloxiani) propyl) (Mexoryl®XL) • 2,2'-methylene bis- (6- (2H-benzotriazol-2-yl) -4-1 , 1,3,3tetramethylbutyl) phenol) (Tinosorb®M) • 2,4-bis- [4- (2-ethylhexyloxy) -2-hydroxyphenyl] -1,3,5-triazine • 2,4-bis- [ {(4- (2-ethylhexyloxy) -2-hydroxy} phenill] -6- (4methoxyphenyl) -1,3,5-triazine (Tinosorb®S) • 2,4-bis sodium salt - [{(4 - (3-sulfonate) -2hydroxypropyloxy) -2-hydroxy} phenill] -6- (4-methoxyphenyl) -1,3,5-triazine • 2,4-bis - [{(3- (2-propyloxy) - 2-hydroxypropyloxy) -2-hydroxy} phenill] 6- (4-methoxyphenyl 1) -1,3,5-triazi na • 2,4-bis - [{4- (2-ethylhexyloxy) -2-hydroxy} phenill] -6- [4- (2methoxyethylcarbonyl) phenillamino] -1,3,5-triazine • 2,4-bis - [{4- (3- (2-propyloxy) -2-hydroxypropyloxy) -2hydroxy} fe nill] -6- [4- (2-ethylcarboxyl) phenillamino] -1,3,5-triazine • 2,4-bis - [{4- (2-ethylhexyloxy) -2-hydroxy} phenill] -6- ( 1-methylpyrrol-2yl) -1,3,5-triazine • 2,4-bis - [{4-tris- (trimethylsiloxysilylpropyloxy) -2-hydroxy} phenill] -6 (4-methoxyphenyl) -1,3,5 -triazine • 2,4-bis - [{4- (2-methylpropenyloxy) -2-hydroxy} phenill] -6- (4methoxyphenyl) -1,3,5-triazine • 2,4-bis - [{4- (R, R, R, 3, 5, 5, 5'-heptametilsilóxi-2metilpropilóxi) -2-hydroxy} phenyl] -6- (4-methoxyphenyl) -1,3,5-triazine
    Petition 870170023194, of 04/07/2017, p. 49/150
    47/135 [00156] UV-A filters that are preferably combined with one or more compounds of formula (I) in a preparation according to the present invention are selected from the group consisting of • 4-isopropyl dibenzoyl methane • sulfonic acid terephthalyldene dibornane and salts (Mexoryl®SX) • 4-t-butyl-4 , -methoxydibenzoyl methane (avobenzone) / (Neo Heliopan®357) • phenylene bis-benzimidazyl tetrasulfonic acid salt (Neo Heliopan®AP) • 2,2 '- (1,4-phenylene) -bis- (1 H-benzimidazole-4,6 disulfonic acid), monosodium salt • 2- (4-diethylamino-2-hydroxybenzoyl) benzoic acid hexyl ester (Uvinul® A Plus) • indanildene compounds according to DE 100 55 940 (= WO 02/38537) [00157] UV filters that are more preferably combined with one or more compounds of formula (I) in a preparation according to the present invention are selected from the group consisting of • p-aminobenzoic acid • 3- (4'-trimethylammonium) benzylidene bornan-2ona methyl sulfate • homomentile salisyl acid ester (Neo Heliopan®HMS) • 2-hydroxy-4-methoxybenzophenone (Neo Heliopan®BB) • 2-phenylbenzimidazole sulfonic acid (Neo Heliopan®Hidro) • terephthalildene dibornane sulfonic acid and salts (Mexoryl®SX) • 4-tert-butyl-4'-methoxydibenzoyl methane (Neo HelioPetição 870170023194, 04/04/2017, pg. 50/150
    48/135 pan®357) • 3- (4'-sulfo) benzylidene bornan-2-one and salts • 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate (Neo Heliopan®303) • N- polymer [(2 and 4) - [2- (oxoborn-3-ildene) methyl] benzyl] acrylamide • 2-ethylhexyl ester of p-methoxycinnamic acid (Neo Heliopan®AV) • ethyl ester of p-aminobenzoic acid (25 mol) ethoxylate (INCI name: PEG-25 PABA) • p-methoxycinnamic acid isoamyl ester (Neo Heliopan®E1000) • 2,4,6-trianilino- (p-carbo-2'-ethylhexyl-1 '-oxy) -1 , 3,5-triazine (Uvinul®T150) • phenol, 2- (2H-benzotriazol-2-yl) -4-methyl-6- (2-methyl-3 (1,3,3,3tetramethyl-1 - ( trimetiIsiIiI) oxy) disyloxianiI) propyl) (Mexoryl®XL) • 4.4 '- [(6- [4- (1,1-dimethyl) aminocarbonyl) phenylamino] -1,3,5triazine-2,4-diyl) diimino] -bis - (- 2-ethylhexyl benzoic acid ester) (Uvasorb HEB) • 3- (4'-methyl benzylidene) -D, L-camphor (Neo Heliopan®MBC) • 3-benzylidene camphor • 2-ethylhexyl salisyl acid ester (Neo Heliopan®OS) • 2-ethylhexyl ester of 4-dimethylaminobenzoic acid (PadimateO) • hydroxy-4-methoxybenzophenone- 5-sulfonic and Na salt • 2,2-methylene bis- (6- (2H-benzotriazol-2-yl) -4-1,1,3,3tetramethylbutyl) phenol) (Tinosorb®M) • disodium salt of phenylene acid bis-benzimidazyl tetrasulfonic (Neo Heliopan®AP)
    Petition 870170023194, of 04/07/2017, p. 51/150
    49/135 • 2,4-bis - [{(4- (2-ethylhexyloxy) -2-hydroxy} phenill] -6- (4methoxyphenyl) -1,3,5-triazine (Tinosorb®S) • malonate polysiloxane benzylidene (Parsol®SLX) • menthyl anthranylate (Neo Heliopan®MA) • 2- (4-diethylamino-2-hydroxybenzoyl) hexyl ester) benzoic acid (Uvinul® A Plus) • indanildene compounds according to DE 100 55 940 (= WO 02/38537).
    [00158] Advantageous inorganic light protection pigments are finely dispersed metal oxides and metal salts which are also mentioned in WO 2005/123101. The total amount of inorganic pigments, in particular hydrophobic inorganic micropigments in the finished cosmetic preparation according to the present invention is advantageously from 0.1 to 30% by weight, preferably from 0.5 to 10.0% by weight, in each case, based on the total weight of the preparation.
    [00159] In addition, filters for UV particles or inorganic pigments, which can optionally be hydrophobic, can be used, such as titanium (TiO 2 ), zinc (ZnO), iron (Fe 2 O 3 ), zirconium (ZrO 2 ), silicon (SiO 2 ), manganese (MnO, for example), aluminum (AI2O 3 ), cerium (Ce 2 O 3 for example) and / or their mixtures.
    [00160] Corticosteroid-type steroidal anti-inflammatory substances, such as, for example, hydrocortisone, dexamethasone, dexamethasone phosphate, methyl prednisolone or cortisone, are advantageously used as anti-inflammatory active ingredients or active ingredients to relieve redness and itching. list of which can be extended by adding other anti-inflammatory steroids. Non-steroidal anti-inflammatory drugs can also be used. Examples that can be cited here are oxicams such as piroxicam or
    Petition 870170023194, of 04/07/2017, p. 52/150
    50/135 tenoxicam; salicylates such as aspirin, disalcid, solprin or fendosal; acetic acid derivatives, such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin or clindanac, fenmatos such as mefenamic, meclofenamic, flufenamic or niflumic; propionic acid derivatives, such as ibuprofen, naproxen, benoxaprofen, or pyrazoles, such as phenylbutazone, oxyphenylbutazone, febrazone or azapropazone. Anthranilic acid derivatives, in particular avenanthramides described in WO 2004/047833, are preferred anti-itchy ingredients in a composition according to the present invention. Alternatively, natural anti-inflammatory substances or substances to relieve redness and itching can be used. Plant extracts, special highly active plant extracts fractions and high purity active substances isolated from plant extracts can be used. Particularly preferred are extracts, fractions and active substances from chamomile, aloe vera, species commiphora, species rubia, species echinacea, willow, willow herb, oats, black and green tea, gingko, coffee, pepper, black currant, tomato , vanilla, almonds, as well as pure substances, such as, in particular, bisabolol, apigenin-7-glycoside, boswellic acid, phytosterols, glycyrrhizic acid, glabridine or licochalcona A.
    [00161] In other preferred embodiments, a composition according to the present invention, comprises one or more active ingredients that offer a benefit to the skin, in particular the reduction of skin irritation or skin calming agents, preferably selected from from the group consisting of anti-inflammatory agents, compounds that relieve itching and / or compounds that relieve redness, which are suitable for cosmetic and / or dermatological applications, in which the one or more active ingredients are preferably selected from the groups that consist of:
    - anti-inflammatory steroidal substances of the type corticoiPetition 870170023194, of 07/04/2017, p. 53/150
    51/135 des, in particular hydrocortisone derivatives, hydrocortisone such as hydrocortisone 17-butyrate, dexamethasone, dexamethasone phosphate, methylprednisolone and cortisone and / or;
    - Mixtures of natural or naturally occurring anti-inflammatory substances or mixtures of substances that relieve redness and / or itching, in particular extracts or fractions of chamomile, aloe vera, commiphora species, rubia, willow, willow, oat, marigold, arnica, St. John's wort, honeysuckle, rosemary, Passiflora incarnata, witch hazel, ginger or Echinacea, preferably selected from the group consisting of extracts or fractions of chamomile, aloe vera, oats, marigold, arnica, honeysuckle, rosemary, witch hazel, ginger or echinacea, and / or
    - pure substances, preferably alpha-bisabolol, apigenin, apigenin-7-glycoside, gingerols, shogaols, gingerdiols, dehydroginger-diones, paradols, natural or naturally occurring avenantramides, preferably tranilast, avenantramide A, avenantramide B, avenantramide C, avenantramides natural and naturally occurring, preferably dihydroavenanthramide D, dihydroavenanthramide E, avenanthramide D, avenanthramide E, avenanthramide F, boswellic acid, phytosterols, glycyrrhizin, and glabridin licochalcona A; preferably selected from the group consisting of alpha-bisabolol, gingerols, shogaols, gingerdiols, dehydrogingerdiones, paradols, natural avenanthramides and unnatural avenanthramides, preferably dihydroavenanthramide D (as described in WO 2004/047833), boswelic acid, phytosterols , glycyrrhizin, and lycochalcone A, and / or [00162] Preferably a preparation according to the present invention comprises one or more active agents selected from the groups consisting of:
    - extracts or fractions of chamomile, aloe vera, oats, caPetition 870170023194, from 04/07/2017, p. 54/150
    52/135 lendula, arnica, honeysuckle, rosemary, witch hazel, ginger or echinacea, and / or
    - alpha-bisabolol, gingerols, shogaols, gingerdiols, dehydrogingerdiones, paradols, natural avenanthramides and unnatural avenanthramides, dihydroavenanthramide D, preferably boswellic acid, phytosterols, glycyrrhizin, and lychalcone A and / or;
    - urea, hyaluronic acid, allantoin, panthenol, lanolin, alpha-hydroxy acid (preferably citric acid, lactic acid), vitamin E and its derivatives (preferably tocopherol acetate, tocopherol). [00163] When bisabolol is used in the context of the present invention, it can be of natural or synthetic origin, and is preferably alpha-bisabolol. Preferably, the bisabolol used is synthetically prepared or (-) - natural alpha-bisabolol and / or synthetic mixed isomer alpha-bisabolol. If (-) - natural alpha-bisabolol is used, it can also be used as a constituent of an essential oil or a plant extract or a fraction thereof, for example, as constituents of (fractions of) oil or extracts of chamomile or vanillosmopsis (in particular Vanillosmopsis erythropappa or Vanillosmopsis arboreal). Synthetic alpha-bisabolol is obtained, for example, under the name Dragosantol from Symrise.
    [00164] When ginger extract is used in the context of the present invention, preferably fresh or dried ginger root extracts are used which are obtained by extraction with methanol, ethanol, iso-propanol, acetone, ethyl acetate , carbon dioxide (CO 2 ), hexane, methylene chloride, chloroform or other solvents or solvent mixtures of comparable polarity. Extracts are characterized by the presence of amounts of irritation-reducing active ingredients in the skin of constituents, such as, for example, gingerols, shogaols, gingerdiols dehydrogingerdionas, and / or paradols.
    [00165] The formulations according to the invention can also
    Petition 870170023194, of 04/07/2017, p. 55/150
    53/135 contain (additional) anti-oxidants or preservatives. All antioxidants that are suitable capable or commonly used for cosmetic (dermatological, for example) and / or therapeutic applications can be used as antioxidants or preservatives.
    [00166] Antioxides, as part of a preparation according to the present invention, are preferably chosen from the group comprising amino acids (for example, glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (for example, urocanic acid) and its derivatives, peptides such as D, L-carnosine, Dcarnosine, L-carnosine and its derivatives (for example, anserine), carnitine, creatine, matrikin peptides (for example, lysyl-threonyltreonyl-lysyl-serine) and palmitoylated pentapeptides, carotenoids, carotenes (for example, alpha-carotene, beta-carotene, lycopene) and their derivatives, lipoic acid and its derivatives (for example, dihydrolipoic acid), aurothioglucose, propyl thiouracil and other thiols (for example thioredoxin , glutathione, cysteine, cystine, cystamine and glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, gammalinoleyl, cholesteryl, glyceryl and oligoglyceril esters of the same) and their salts, thiodipropion dilauryl, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (eg, butionin sulfoximines, homocysteine sulfoximine, butionine sulfoxines, penta- , hexa-, heptathionine sulfoximine) in very small tolerated doses (eg pmol to pmol / kg), also chelators (metal) (eg alpha hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin, alpha- hydroxy (eg, citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, tannins, bilirubin, biliverdin, EDTA, EGTA and their derivatives), unsaturated fatty acids and their derivatives (eg gamma-linolenic acid, linoleic acid, oleic acid), folic acid and
    Petition 870170023194, of 04/07/2017, p. 56/150
    54/135 their derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and derivatives (eg ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate, ascorbyl glucoside), tocopherols and their derivatives (eg vitamin E), vitamin A and derivatives (vitamin A palmitate) and benzoic resin coniferyl benzoate, rutinic acid and its derivatives, flavonoids and their glycosylated precursors, in particular, quercetin and its derivatives, for example alpha-glucosyl rutin, rosmarinic acid, carnosol, carnosolic acid, resveratrol, caffeic acid and its derivatives, synapic acid and its derivatives, ferulic acid and its derivatives, curcuminoids, chlorogenic acid and its derivatives, retinoids, such as retinyl palmitate, retinol or tretinoin, ursolic acid, levulinic acid, butylhydroxytoluene, butyl hydroxyanisole, nordihydroguaiaco acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, zinc and its derivatives (for example, ZnO, ZnSO 4 ), selenium and its derivatives (for example, selenium methionine), superoxide dismutase, stilbenes and their derivatives (for example, stylbene oxide, trans-stilbene oxide) and derivatives (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active ingredients mentioned that are suitable according to the invention or extracts or plant fractions that have an anti-inflammatory effect. oxidant, such as green tea, rooibos, honeybush, grape, rosemary, sage, melissa, thyme, lavender oats, olive oil, cocoa, ginkgo, ginseng, licorice, honeysuckle, sophora, pueraria, pinus, citrus, phyllanthus emblica or St. John's wort, grape seeds, wheat germ, phyllanthus emblica.
    [00167] Also suitable are coenzymes, such as, for example, coenzyme Q10, plastoquinone, menaquinone, ubiquinols 110, ubiquinones 1-10 or derivatives of these substances.
    [00168] If vitamin E and / or its derivatives are used as
    Petition 870170023194, of 04/07/2017, p. 57/150
    55/135 antioxidant (s), it is advantageous to choose their concentrations from the range from 0.001 to 10% by weight, based on the total weight of the formulation.
    [00169] If vitamin A or derivatives of vitamin A or carotenes or their derivatives are used as antioxidant (s), it is advantageous to choose their concentrations from the range from 0.001 to 10% by weight, based on the total weight formulation.
    The present invention additionally relates to new compounds of formula (I) or a cosmetically acceptable salt thereof;
    O

    THE IN
    H
    O
    H
    O
    H
    O>
    Ό IN
    H
    Petition 870170023194, of 04/07/2017, p. 58/150
    56/135


    [00171] The (particularly) preferred compounds of general formula (I) of the present invention are preferably used in the preferred compositions indicated above or below.
    [00172] The (particularly) preferred aspects and modalities mentioned above or below with respect to compounds of formula (I) or compositions (preparations) comprising one or more compounds of formula (I) according to the present invention also apply to (particularly) preferred aspects and modalities, uses and methods according to the present invention.
    [00173] The present invention additionally relates to a method for cosmetic lightening of the skin and / or hair, comprising
    Petition 870170023194, of 04/07/2017, p. 59/150
    57/135 the following step:
    - application, preferably topical application, of a cosmetically effective amount of a compound of formula (I) or a cosmetically acceptable salt thereof of a compound of formula (I) or a mixture containing two or more of these compounds or their salts as herein cosmetic composition as defined herein.
    [00174] An additional aspect of the present invention is the use of a compound of formula (I) or a pharmaceutically acceptable salt of a compound of formula (I) or a mixture containing two or more of these compounds or their salts as defined herein
    - for the preparation of a pharmaceutical product, preferably topical, composition for whitening skin and / or hair, in particular for whitening hyperpigmentation.
    [00175] The present invention further relates to a compound of formula (I) or a pharmaceutically acceptable salt thereof of a compound of formula (I) or a mixture containing two or more of these compounds or their salts as defined herein, as a medicine, preferably as an active agent for whitening skin and / or hair, in particular as an active agent for whitening hyperpigmentation.
    [00176] The present invention also relates to a pharmaceutical composition comprising a pharmaceutically active amount of one or more compounds of formula (I) as defined herein, preferably for lightening the skin and / or hair, in particular for lightening hyperpigmentation.
    [00177] Furthermore, the present invention also relates to a method for whitening skin and / or hair, preferably for whitening hyperpigmentation, which comprises the following step:
    - application, preferably topical application, of a quantity 870170023194, of 07/04/2017, p. 60/150
    58/135 pharmaceutically effective compound of a compound of formula (I) or a pharmaceutically acceptable salt of a compound of formula (I) or a mixture containing two or more of these compounds or their salts as defined herein or of a pharmaceutical composition such as defined here.
    [00178] The present invention also relates to a cosmetic or therapeutic method for whitening human skin and / or hair, comprising the step of
    - supplying one or more compounds of formula (I) or a cosmetic or pharmaceutically acceptable salt thereof, or a cosmetic or pharmaceutical composition according to the present invention,
    - application of one or more compounds of formula (I) or the composition to human skin and / or hair in an effective amount,
    - the application preferably remaining for at least 10 minutes, more preferably for at least 30 minutes, more preferably for at least 60 minutes, on said skin and / or hair (product without rinsing).
    [00179] Substances and auxiliaries which may additionally contain a preparation according to the invention, containing one or more compounds of formula (I) are, for example:
    [00180] preservatives, in particular those described in US 2006/0089413, antimicrobial agents, such as, for example, antibacterial agents or agents for clearing yeast and mold, in particular those described in WO 2005/123101, anti-acne and reducing agents if fat, in particular those described in WO 2008/046791, compounds against skin aging, in particular those described in WO 2005/123101 and US 2009/0232915, anti-cellulite agents, in particular those described in WO 2007/077541,
    Petition 870170023194, of 04/07/2017, p. 61/150
    59/135 anti-dandruff agents, in particular those described in WO 2008/046795, anti-irritants (anti-inflammatory agents, irritation prevention agents, irritation inhibiting agents), in particular those described in WO 2007/042472 and US 2006 / 0089413, antioxidants, in particular those described in WO 2005/123101, carrier materials, in particular those described in WO 2005/123101, chelating agents, in particular those described in WO 2005/123101, deodorants and antiperspirants, in particular those described in WO 2005/123101, moisture regulators (moisture donating agents, wetting substance, moisture retention substances), in particular those described in WO 2005/123101, osmolites, in particular those described in WO 2005/123101, compatible solutes, in particular those described in WO 01/76572 and WO 02/15868, proteins and protein hydrolysates, in particular those described in WO 2005/123101 and WO 2008/46676, lightening agents and skin, in particular those described in WO 2007/110415, cooling agents, in particular those described in WO 2005/123101, skin cooling agents, in particular those described in WO 2005/123101, skin heating agents, in particularly those described in WO 2005/123101, UV absorbing agents, in particular those described in WO 2005/123101, UV filters, in particular those described in WO 2005/123101, benzylidene-beta-dicarbonyl compounds according to WO 2005/107692 and alpha-benzoyl cinnamic acid nitriles according to WO 2006/015954, insect repellents, in particular those described in WO 2005/123101, plant parts, plant extracts, in particular those described in WO 2005/123101, vitamins, in particularly those described in WO 2005/123101, emulsifiers, in particular those described in WO 2005/123101, gelling agents, in particular those described in WO 2005/123101,
    Petition 870170023194, of 04/07/2017, p. 62/150
    60/135 oils in particular those described in WO 2005/123101, waxes in particular those described in WO 2005/123101, fats in particular those described in WO 2005/123101, phospholipids, in particular those described in WO 2005/123101, fatty acids saturated and mono- or polyunsaturated fatty acids and α-hydroxy acids and polyhydroxy fatty acids and saturated and / or unsaturated alkane carboxylic acid esters, in particular those described in WO 2005/123101, surface active substances (surfactants), in particular those described in WO 2005/123101, skin repair agents comprising cholesterol and / or fatty acids and / or ceramides and / or pseudoceramides, in particular those described in WO 2006/053912, paint and stains and pigments, in particular those described in WO 2005/123101, aroma chemicals and flavorings and fragrances, in particular those described in S. Arctander, Perfume and Flavor Chemicals, private publishing house, Montclair, NJ, 1969 and Surburg, Panten, Common Fragrance and Flavor Materials, 5th Edition, Wiley-VCH, Weinheim 2006, preferably those explicitly mentioned in US 2008/0070825, alcohols and polyols, in particular those described in WO 2005/123101, organic solvents, in particular those described in WO 2005/12310 silicones and silicone oils and silicone derivatives, in particular those described in WO 2008/046676, virucides, abrasives, astringents, antiseptic, antistatic, binders, buffers, cell stimulants, cleaning agents, care agents, depilatory agents, conditioners, enzymes, essential oils, in particular those described in US 2008/0070825, fibers, film-forming agents (eg polyvinyl-pyrrolidones, chitosan or chitosan derivatives), fixatives, agents foaming agents, foam stabilizers, foam-preventing substances, foam intensifiers, gel forming agents, cr activators growing of
    Petition 870170023194, of 04/07/2017, p. 63/150
    61/135 hair, hair growth inhibitors, hair care agents, hair setting agents, straightening agents, hair straightening, lightening agents, strengthening agents, stain removal, optically brightening agents, impregnating agents , dirt-repellent agents, friction-reducing agents, lubricants, opacifying agents, plasticizers, coating agents, polishing agents, polishing agents, polymers, in particular those described in WO 2008/046676, powders, peptides, mono-, di-e oligosaccharides, re-oiling agents, abrasive agents, tissue whitening agents, soothing agents, skin cleansing agents, skin care agents, skin softening agents, skin protection agents, nourishing agents, skin heating, stabilizers, detergents, tissue conditioning agents, suspending agents, thickeners, yeast extracts, algae or microalgae extracts, animal extracts, liquid uefaction, color protective agents, agents and electrolytes.
    [00181] In a preferred embodiment, a preparation according to the present invention comprises one or more compounds of formula (I) and one or more hair growth modulating active ingredients, in particular, one or more growth-stimulating agents of the hair.
    [00182] Preferred agents for stimulating hair growth are selected from the group consisting of pyrimidine derivatives, in particular 2,4-diaminopyrimidine-3-oxide (Aminexil), 2,4-diamine-6-piperidine-pyrimidine-3 -oxide (Minoxidil) and its derivatives, 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidino-pyrimidine and its derivatives, xanthine alkaloids, in particular, caffeine, theobromine and theophylline and their derivatives, quercetin and their derivatives, dihydroquercetin (taxifoline) and their derivatives, potassium channel openers, antiandrogenic agents, synthetic 5-reductase inhibitors
    Petition 870170023194, of 04/07/2017, p. 64/150
    62/135 or natural, esters of nicotinic acid, in particular tocopherol nicotinate, benzyl nicotinate and C1-C6 alkyl nicotinate, proteins, in particular, Lys-Pro-Val tripeptide, diphencipren, hormones, finasteride, dutasteride, flutamide, bicalutamide, pregnane derivatives, progesterone and its derivatives, cyproterone acetate, spironolactone and other diuretics, calcineurin inhibitors, in particular FK506 (Tacrolimus, Fujimycin) and its derivatives, cyclosporine A and its derivatives, zinc and zinc salts, polyphenols , procyanidins, proanthocyanidins, phytosterols, in particular beta-sitosterol, biotin, eugenol, glycogen (±) -beta-citronelol, panthenol, in particular from mussels, rice hydrolysates, wheat hydrolyzate and microorganism extracts, parts of microalgae , algae or plants and parts of plants, in particular the genus dandelion (Leontodon or Taraxacum), Orthosiphon, Vitex, Coffea, Paullinia, Theobroma, Asiasarum, Cucurbita or Styphnol obium, Serenoa repens (saw palmetto), Sophora flavescens, Pygeum africanum, Panicum miliaceum, Cimicifuga racemosa, Glicine max, Eugenia caryophyllata, Cotinus coggygria, Hibiscus rosasinensis, Camellia sinensis, llex paraguariensis, licorice, apple, licorice, uva, licorice, uva, licorice, uva, licorice, uva, licorice, uva, licorice, apple, licorice, uva.
    [00183] In another preferred embodiment, a preparation according to the present invention comprises one or more compounds of formula (I) and one or more agents to inhibit hair growth.
    [00184] Preferred agents for inhibiting hair growth are selected from the group consisting of activin, activin derivatives or activin agonists, ornithine decarboxylase inhibitors, in particular alpha-difluoromethylomitine or pentacyclic triterpenes, in particular, acid ursolic, betulin, betulinic acid, oleanolic acid and its derivatives, 5alpha-reductase, androgen receptor antagonists, S-adenosylmethionine decarboxylase inhibitors, iniPetição 870170023194, from 07/04/2017, pg. 65/150
    63/135 gamma-glutamyl transpeptidase binders, transglutaminase inhibitors, soy derived serine protease inhibitors, and extracts of microorganisms, algae, microalgae, or plants and parts of plants, in particular from the Leguminosae, Solanaceae, Graminae families , Asclepiadaceae or Cucurbitaceae, the genus Chondrus, Gloiopeltis, Ceramium, Durvillea, Glicine max, officinalis Sanguisorba, Calendula officinalis, Hamamelis virginiana, Arnica montana, Salix alba, Hypericum perforatum and wild Gymnema.
    [00185] Equally advantageous are the preparations according to the invention, which are administered orally, for example in the form of tablets (for example, film tablets), coated tablets, capsules (for example gelatin capsules), granulates, juices, emulsions, solutions, microemulsions, sprays products that can be consumed orally in any other form, or in the form of food, which, because of the compound (s) contained in formula (I) occurs the beauty of inside.
    [00186] The following osmolites can be a component of a preparation according to the present invention: sugar alcohols (myo-inositol, mannitol, sorbitol), quaternary amines, such as taurine, choline, betaine, betaine glycine, ectoin, diglycerol phosphate, phosphorylcholine, glycerophosphoryl cholines, amino acids, such as glutamine, glycine, alanine, glutamate, aspartate or phosphatidylcholine, proline, phosphatidylinositol, inorganic phosphates, and the polymers of the compounds mentioned, such as proteins, peptides and poly acids. Preferred osmolites, which can be a component of a preparation according to the invention, are diglycerol phosphate and / or ectoin.
    [00187] Preferred cosmetic carrier materials, which can be a component of a preparation according to the invention, are solid or liquid at 25 ° C and 1013 mbar (including highly viscous substances).
    Petition 870170023194, of 04/07/2017, p. 66/150
    64/135 [00188] Preferred liquid carrier substances, which can be a component of a preparation according to the invention are selected from the group consisting of glycerol, 1,2propylene glycol, 1,2-butylene glycol, 1,3-butylene -glycol, 1,2-pentanediol,
    1,2-hexanediol, 1,2-octanediol, 1,2-decanediol, water, ethanol and mixtures of two or more of said liquid carrier materials with water. Optionally, these preparations according to the invention can be produced using preservatives, solubilizers or antioxidants.
    Preferred solid carrier materials, which can be a component of a preparation according to the present invention are hydrocolloids, such as starches, degraded starches, chemically or physically modified starches, dextrins, (powder) maltodextrins (preferably with an equivalent dextrose value of 5 to 25, preferably 10 - 20), lactose, silicon dioxide, glucose, modified celluloses, gum arabic, ghatti gum, traganto, karaya, carrageenan, pullulan, curdlan, xanthan gum, gum gelano, guar flour, locust bean flour, alginates, pectin agar, and inulin, and mixtures of two or more of these solids, in particular maltodextrin (preferably with an equivalent dextrose value of 15 - 20), lactose, silicon dioxide and / or glucose.
    [00190] In addition, the preparations according to the invention can be present in encapsulated form, preferably they are encapsulated with a solid covering material, which is preferably selected from degraded starches, or chemically or physically modified starches ( in particular dextrins and maltodexterins), gelatin, gum arabic, agar, ghatti gum, gellan gum, modified and unmodified celluloses, pullulan, curdlan, carrageenan, alginic acid, alginates, pectin, inulin, xanthan gum, and mixtures of two or more of the said substances.
    Petition 870170023194, of 04/07/2017, p. 67/150
    65/135 [00191] The solid coating material is preferably selected from gelatin (preferred are pork, beef, chicken and / or fish gelatines and mixtures thereof, preferably comprising at least one gelatin with a value of efflorescence greater than or equal to 200, preferably with an efflorescence value greater than or equal to 240), maltodextrin (preferably obtained from maize (maize), wheat, tapioca and potatoes, preferred maltodextrins have a DE value of 10 - 20), modified cellulose (eg cellulose ether), alginates (eg Na alginate), carrageenan (beta-, iota-, lambda- and / or kappa), arabic gum, curdlan and / or agar. Gelatine is preferably used, in particular, because of its good availability at different efflorescence values. Particularly relevant, especially for oral use are seamless gelatin capsules or alginate, the covering of which dissolves quickly in the mouth or in bursts when chewing. The production can be carried out, for example, as described in EP 0 389 700, USA 4,251,195, USA 6,214,376, WO 03/055587 or WO 2004/050069. [00192] Preferred cosmetic, dermatological or pharmaceutical preparations according to the present invention are selected from the group of products for whitening, protection, care and cleaning of the skin and / or hair or as a make-up product, preferably as a product without rinsing (meaning that one or more compounds of formula (I) remain on the skin and / or hair for a long period of time, in particular, as defined above, compared to rinsing products, so that the lightening action of the skin and / or hair is more pronounced). [00193] The formulations according to the invention are preferably in the form of an emulsion, for example, emulsion W / O (water in oil), O / W (oil in water), W / O / W (water in oil) in water), O / W / O (oil in water in oil), PIT emulsion, pickering emulsion, emulsion
    Petition 870170023194, of 04/07/2017, p. 68/150
    66/135 with a low oil content, micro or nano emulsion, a solution, for example, in oil (fatty oils or fatty acid esters, in particular C 2 -C 30 esters of C 6 -C 32 fatty acid) or silicone oil, dispersion, suspension, cream, lotion or milk, depending on the production method and ingredients, a gel (including hydrogel, hydrodispersion gel, oleogel), spray (for example, pump spray or propellant spray) or a foam or impregnation solution for cosmetic wet wipes, a detergent, for example, a soap, synthetic detergent, washing liquid, shower and bath preparation, bath product (capsule, oil, tablet, salt, bath salt , soap, etc.), effervescent preparation, a skin care product, such as an emulsion (as described above), ointment, paste, gel (as described above), balm oil, whey powder (for example , rice powder, body powder), a mask, a pencil, stick, roll-on, bo mba, aerosol (foaming, non-foaming or post-foam), a deodorant and / or antiperspirant, mouthwash and mouthwash, a foot care product (including deodorant, keratolytic), an insect repellent, protector sunscreen, after-sun preparation, a shaving product, aftershave balm, pre- and aftershave lotion, a depilatory agent, a hair bleaching product such as shampoo (including 2 in 1 shampoo, anti-dandruff shampoo , dry scalp shampoo, concentrated shampoo), conditioner, hair tonic, hair water, hair cream, styling cream, ointment, perm and ambient lotion, hair spray, styling aid (for example gel or wax), agent hair straightening agent (detangling, relaxing agent), hair dye, for example, hair dye for temporary hair dyeing, semi-permanent hair dye, permanent hair dye, hair conditioner, hair mousse, product eye care, makeup m, produPetição 870170023194, of 04/07/2017, p. 69/150
    67/135 to makeup remover or baby product.
    [00194] It is also advantageous to administer the compounds of general formula (I) in encapsulated form, for example, in gelatin, wax, liposome or cellulose capsule materials.
    [00195] The formulations according to the invention are particularly preferably in the form of an emulsion, in particular in the form of an emulsion W / O, / W, W / O / W, O / W / O, PIT emulsion, pickering emulsion, emulsion with a low oil content, micro or nanoemulsion, a gel (including hydrogel, hydrodispersion gel, oleogel), for example, a solution in oil (fatty oils or fatty acid esters, in particular C 2 esters -C 30 of C 6 -C 32 fatty acid)) or silicone oil, or a sprayer (for example, pump sprayer or propellant sprayer).
    [00196] Auxiliary substances and additives that can be included in quantities of 5 to 99% by weight, preferably 10 to 80% by weight, based on the total weight of the formulation. The quantities of cosmetic or dermatological auxiliary agents and additives and perfume to be used in each case can be easily determined by the person skilled in the art by simple trial and error, depending on the nature of the product in question.
    [00197] The preparations can also contain water in an amount of up to 99% by weight, preferably 5 to 80% by weight, based on the total weight of the preparation.
    [00198] The one or more substances with a physiological cooling effect (cooling agents), which can be used in combination with one or more compounds of general formula (I) according to the invention, are preferably selected here from from the following list: menthol and menthol derivatives (eg L-menthol, Dmentol, racemic menthol, isomentol, neoisomentol, neomenthol) menthylethers (eg (l-mentoxy) -1,2-propandiol, (l-mentoxy) - 2-methyl-1,2Petition 870170023194, of 07/04/2017, page 70/150
    68/135 propandiol, l-menthyl-methylether), menthyl esters (for example menthylformate, menthylacetate, menthylisobutyrate, mentillactates, L-menthyl-Llactate, L-menthyl-D-lactate, menthyl- (2-methoxy) acetate, menthyl- ( 2methoxyethoxy) acetate, menthylpyroglutamate), menthylcarbonates (for example menthylpropylene glycolcarbonate, menthyl ethylene glycolcarbonate, menthyl glycerolcarbonate or mixtures thereof), half esters of menthol with a dicarboxylic acid or derivatives thereof (for example mono-menthyl mono-mono-mono-butyl mononate, mono-mono-mono-mono-mono-mono-butyl), , O- menthyl succinic acid N- (dimethyl) amide, O-menthyl succinic acid ester amide), mentanocarboxylic acid amides (in this case preferably N-ethylamide [WS3] of mentanecarboxylic acid or Na- (mentanocarbonyl) glycketylester [ WS5], as described in US 4,150,052, mentanocarboxylic acid N- (4-cyanophenill) amide or mentanecarboxylic acid N- (4-cyanomethyl) amide as described in WO 2005/049553, N- (alkoxyalkyl) amides) of water methanecarboxylic acid, menthol and menthol derivatives (eg L-mentone glycerol ketal), derivatives of 2,3-dimethyl 1-2- (2propyl)-butyric acid (eg 2,3-dimethyl-2- N-methylamide) (2-propyl) butyric [WS23]), isopulegol or its esters (l - (-) - isopulegol, 1 - (-) isopulegolacetate), derivatives of mentane (for example p-mentano3,8-diol), baseball or mixtures synthetic or natural, containing baseball, pyrrolidone derivatives of cycloalkyldione derivatives (for example
    3-methyl-2 (1-pyrrolidinyl) -2-cyclopentene-1-one) or tetrahydropyrimidine-2one (for example icyline or related compounds, as described in WO 2004/026840), additional carboxamides (for example N- (2 ( pyridin-2-yl) ethyl) -3-p-mentanecarboxamide or related compounds), (1R, 2S, 5R) -N- (4-Methoxyphenyl) -5-methyl-2- (1-isopropyl) cyclohexanecarboxamide [ WS12], oxamates (preferably those described in EP 2 033 688 A2).
    [00199] The plurality of substances with a cooling effect
    Petition 870170023194, of 04/07/2017, p. 71/150
    69/135 physiological, which can be used in combination with one or more compounds of formula (I) according to the invention, are in particular preferably substances, which at least substantially cause a physiological cooling effect. Such preferred substances are: menthyl ethers (for example (l-mentoxy) -1,2-propandiol, (l-menthoxy) -2methyl-1,2-propandiol), polar menthyl esters (for example mentillacetates, L-mentyl-L-lactate , L-menthyl-D-lactate, menthyl- (2-methoxy) acetate, menthyl- (2-methoxyethoxy) acetate, menthylpyroglutamate), menthylcarbonates (for example menthylpropylene glycolcarbonate, menthyl ethylene glycolcarbonate, menthylglycerolcarbonate), with a mentar acid esters or semi-esters. derivatives thereof (for example monomentyl succinate, mono-mentylglutarate, mono-mentylmalonate, esterN, N- (dimethyl) amide of O-menthyl succinic acid, O-menthyl succinic acid esteride), not according to the invention, amides of Mentane carboxylic acid (for example M-carboxylic acid N-ethylamide [WS3], Na- (mentanocarbonyl) glycinetylester [WS5], N (4-cyanophenill) carboxylic acid, N (alkoxyalkyl) amides) of carboxylic acid, Mentone derivatives (eg L-mentone glycerol ketal) , 2,3-dimethyl-2- (2-propyl) -butyric acid derivatives (eg 2,3-dimethyl-2- (2-propyl) -butyric acid -N-methylamide), pyrrolidone derivatives of cycloalkyl dione derivatives (for example example 3-methyl-2 (1-pyrrolidinyl) -2-cyclopentene-1one) or tetrahydropyrimidine-2-ones (for example icyline or related compounds, which are described in WO 2004/026840), 1R, 2S, 5R) -N - (4Methoxyphenyl) -5-methyl-2- (1-isopropyl) cyclohexane-carboxamide [WS12], L-Mentyl N-methyl oxamate, L-mentyl N-ethyl oxamate (as described in EP 2 033 688).
    [00200] The total amount of substances that have a physiological cooling effect (one or more compounds) in the preparations according to the invention is preferably in the range from 0.05 - 5%
    Petition 870170023194, of 04/07/2017, p. 72/150
    70/135 by weight, more preferably in the range from 0.1 - 3% by weight, in particular in the range from 0.25 -1.5% by weight, in each case, based on the total weight cosmetic or pharmaceutical preparation. [00201] Components that cause a hot, sharp or prickly sensation on the skin or mucous membranes, in particular flavors with a heat-producing effect and / or sharp sharp tasting compounds (substances) that may, in addition to one or more compounds of formula (I), being a component of a preparation according to the invention, are mentioned in WO 2005/123101.
    [00202] Furthermore, combinations with compounds that reduce the hypersensitivity of the skin nerves based on their action, such as, for example, TRPV1 antagonists, for example, trans-4-tert-butyl-cyclohexanol (as described in WO 2009/087242), or indirect TRPV1 modulators by an μ-receptor activation, for example, acetyl tetrapeptide-15, are preferred.
    [00203] The following anti-cellulite actives can be a component of a preparation, preferably a cosmetic preparation, according to the invention: Lipolysis stimulators such as xanthines, caffeine in particular, extracts containing caffeine, or beta-receptor agonists adrenergics, for example, synephrine and derivatives, and agents that encourage the activity of anti-cellulite agents, for example, agents that stimulate and / or depolarize C nerve fibers, such as capsaicin or vanylyl-nonylamide and its derivatives or extracts containing one or more of these substances, such as extracts obtained from various species of the genus Capsicum (such as Capsicum annum), and compounds that stimulate microcirculation or drainage, preferably selected from the group consisting of broom extract or its component active ruscogenin, chestnut extract or its active component escin, ivy extract
    Petition 870170023194, of 04/07/2017, p. 73/150
    71/135 and / or pineapple extract, (e) L-carnitine, coenzyme A, isoflavonoids, soy extracts, conjugated linoleic acid (CLA). Preferably, anti-cellulite actives as a component of a preparation according to the invention are selected from the group consisting of synephrine, caffeine and / or L-carnitine.
    [00204] Preferred preparations, preferably cosmetic preparations, according to the present invention, containing one or more compounds of formula (I), preferably, additionally, contain one or more active ingredients that prevent collapse of connective tissue. Active ingredients are advantageous here that inhibit the matrix metalloproteinases (MMPs). These enzymes are in a position to break extra-cellular matrix (ECM) / connective tissue macromolecules, also including collagens, proteolytically. In particular, matrix-metalloproteinase-1 (MMP-1), matrix-metalloproteinase-2 (MMP-2) and matrix-metalloproteinase-9 (MMP-9) are responsible for tissue degradation connective tissue. An inhibition of MMPs is possible, for example, by the addition of ursolic acid, palmitate, propylate, precocenes, 6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H) benzopyran, 3,4 - di- hydro-6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H) benzopyran. An addition of peptides that inhibit MMPs, the preparation according to the invention, is also advantageous for inhibiting MMPs. Soy proteins or glycoproteins and hydrolyzed proteins from rice, peas or lupins also inhibit MMPs and are therefore a suitable addition. A combination of a plant extract, which inhibits MMPs, is also advantageous. To be mentioned here as an example is an extract of shitake mushrooms. The combination with leaf extracts from the Rosaceae family, Rosoideae sub-family, is also advantageous. Very particularly advantageous is the use of blackberry leaf extract, in particular, as described in WO 2005/123101 A1.
    Petition 870170023194, of 04/07/2017, p. 74/150
    72/135 [00205] The MMP inhibitors to be preferably used in combination within the scope of the present invention are palmitate, propylate, precocenes, 6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H) benzopyran , 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H) benzopyran, benzamidine hydrochloride, cysteine protease inhibitors and epsilon-amino-n-caproic acid N-ethylmalemide serinprotease inhibitors: phenylmethylsuphylfluoride, collhibin (Pentapharm company; INCI: rice hydrolyzed protein), oenoterol (Soliance company; INCI: propylene glycol, aqua, Oenothera biennis root extract, ellagic acid and ellaganthins, for example, from pomegranate), hinokitiol phosphoramidone, EDTA, galardin, EquiStat (Collaborative Group company; apple fruit extract, soy seed extract, ursolic acid, soy isoflavones and soy proteins), sage extracts, MDI (company Atrium; INCI: glycosaminoglycans), fermiskin (company Silab / Mawi; INCI: water and lentinus edodes extract ), actimp 1,9,3 (company Expanscience / Rahn; INCI: hydrolyzed lupine protein), lipobelle soyaglycone (Mibelle company; INCI: alcohol, polysorbate 80, lecithin and soy isoflavones), green and black tea extracts and several new plant extracts, which are listed in WO 02/069992 (see table 1-12).
    [00206] In order to counteract the collapse of connective tissue, the combination of active ingredients, which encourage the formation of collagen in the tissue (collagen stimulants), is still advantageous in preferred cosmetic preparations according to the invention containing one or more compounds of formula (I). Individual substances frequently used to increase collagen synthesis are, for example, ingredients such as ascorbic acid and its derivatives, retinol and its retinol derivatives or plant extracts, such as, for example, extracts of aloe and sparkling species . In addition, peptide materials and their derivatives, such as, for example, carnitine,
    Petition 870170023194, of 04/07/2017, p. 75/150
    73/135 carnosine, creatine, peptides (for example, lysyl-threonyltreonyl-lysyl-serine matriquine) and other peptide structures such as palmitoylated pentapeptides (for example Matrixil / Sederma company) or the oligopeptide with the trade name Vincipeptide (company Vincience / France ) are also included in the frequently used active ingredients that increase collagen synthesis. In addition, compounds such as Asian acid, madecassic acid, madecassoside, asiaticoside, extracts of Asian spark, niacinamide, astaxanthin, glucans, for example, yeast and oats, soy extracts and soy isoflavones, such as genistein and daidzein , rutin, chrysin, morine, betel alkaloids, forskolin, betulinic acid, extracts of Plantago species, TGF-beta, extracts from Ginkgo biloba glutamine and glycolic acid are also used as stimulators of collagen synthesis. Particularly preferred here is the addition of a combination of aloe vera extract, raspberry extract and magnesium ascorbyl phosphate.
    [00207] The formulations according to the invention, in particular dermatological formulations, can also advantageously contain dyes and / or colored pigments, in particular if they are to be used in the field of decorative cosmetics. Colored dyes and pigments can be selected from the corresponding positive list in the German cosmetic ordinance or the EU list of cosmetic dyes. In most cases, they are identical to food-approved dyes. Colored pigments are advantageous, for example, titanium dioxide, mica, iron oxides (for example, Fe 2 O 3 Fe 3 O 4 , FeO (OH)) and / or tin oxide. Advantageous dyes are, for example, carmine, berlin blue, green chromium oxide, ultramarine blue and / or manganese violet.
    [00208] If the topical formulations according to the invention are intended for use in the facial area, it is convenient to choose how the
    Petition 870170023194, of 04/07/2017, p. 76/150
    74/135 dye of one or more substances from the following group: 2,4-dihydroxyzobenzol, 1 - (2'-οΙθΓθ-4'-ηϊίΓθ-1 '-phenillazo) -2-hydroxynaphthalene, red ceres, 2- acid (4-sulfo-1-naphthylazo) -1-naphthol-4-sulfonic, calcium salt of 2-hydroxy acid-1,2 , -azonaphthalene-1 , -sulfonic acid, calcium salts and barium of 1- (2 -sulfo-4-methyl-1-phenylazo) -2-naphthyl carboxylic acid, calcium salt of 1- (2-sulfo-1-naphthylazole) -2-hydroxynaphthalene-3-carboxylic acid, aluminum salt of 1- (4- sulfo-1-phenylazo) -2-naphthol-6sulfonic, aluminum salt of 1- (4-sulfo-1-naphthylazo) -2-naphthol-3,6-disulfonic, 1- (4-sulfo-1-naphthylazo) - 2-naphthol-6,8-disulfonic, 4- (4-sulfo-1-phenylazo) -1- (4-sulfophenyl) -5hydroxypyrazolone-3-carboxylic acid aluminum salt, 4,5dibromofluorescein aluminum and zirconium salts , aluminum salts and zirconium 2,4,5,7tetrabromofluoresceína, 3, 4 ', 5, 6-tetrachloro 2,4,5,7tetrabromofluoresceína and its aluminum salt, aluminum salt of 2,4, 5,7-tetraiodofluorescein, salt quinophthalone disulfonic acid aluminum, indigo disulfonic acid aluminum salt, red and black iron oxide (Color index number (CIN): 77491 (red) and 77499 (black)), iron oxide hydrate (CIN: 77492), ammonium manganese diphosphate and titanium dioxide.
    [00209] Equally advantageous are natural oil-soluble dyes, for example, extracts of paprika, β-carotene or cochoni.
    [00210] Equally advantageous in the sense of the present invention are dermatological formulations containing pearlescent pigments. The types of nacreous pigment listed below are particularly preferred:
    1. natural nacreous pigments, such as, for example,
    - pearl essence (mixed guanine / hypoxanthine crystals obtained from fish scales) and
    - mother-of-pearl (shells of mussels)
    Petition 870170023194, of 04/07/2017, p. 77/150
    75/135
    2. Monocrystalline nacreous pigments such as bismuth oxychloride (BiOCI)
    3. Layered substrate pigments: for example, mica / metal oxide [00211] The base for nacreous pigments is formed for example by powder pigments or dispersions of castor oil, bismuth oxychloride and / or titanium dioxide and oxychloride of bismuth and / or titanium dioxide in mica. The gloss pigment listed in NIC 77163, for example, is particularly advantageous.
    [00212] The list of said nacreous pigments is, of course, not intended to be limiting. Advantageous nacreous pigments in the meaning of the present invention can be obtained in various ways known per se. For example, substrates other than mica can be coated with other metal oxides, such as, for example, silica and the like. SiO 2 particles coated with TiO 2 and Fe 2 O 3 (Ronaspheres), for example, which are sold by Merck and are particularly suitable for the optical reduction of fine lines, are advantageous.
    [00213] It may also be advantageous to completely dispense with a substrate, such as mica. Nacreous iron pigments, which are produced without the use of mica, are particularly preferred. Such pigments are available from BASF, for example, under the copper trade name Sicopearl 1000.
    [00214] Particularly advantageous are also special effect pigments, which are available from Flora Tecnologia under the trade name Metasomes Standard / Glitter in various colors (yellow, red, green, blue). Here the shine particles are mixed with various auxiliary substances and dyes (for example, dyes with NIC 19140, 77007, 77289, 77491).
    [00215] Dyes and pigments can be present either individually 870170023194, from 07/04/2017, p. 78/150
    76/135 dually either mixed and coated with one another, where the effects of different colors can generally be obtained by varying the coating thickness. The total amount of dyes and coloring pigments is advantageously chosen from the range from, for example 0.1% by weight to 30% by weight, preferably 0.5 to 15% by weight, in particular 1 , 0 to 10% by weight, based in each case on the total weight of the formulations (cosmetic).
    [00216] A combination of chelating agents (metal) can also be beneficial in some preparations. Chelating agents (metal) to be used preferably are the compounds mentioned in WO 2005/123101.
    [00217] The one or more compounds of formula (I) can advantageously be used, in particular, in cosmetic and dermatological preparations, in combination with insect repellents, such as, for example, DEET, IR 3225, Dragorepel ™ (Symrise GmbH & Co. KG).
    [00218] The one or more compounds of formula (I) can advantageously be used, in particular in cosmetic and dermatological preparations, in combination with hair agents and anti-dandruff active ingredients (for example, climbazole, ketoconazole, pyroctone oleamine, zinc -pyrithione).
    [00219] The compounds of formula (I) can also be used advantageously in many cases, in combination with one or more preservatives in preparations according to the invention. The preservatives mentioned in WO 2005/123101 are preferably chosen here.
    [00220] The preparations according to the present invention, in addition to the one or more compounds of formula (I), can also contain plant extracts that can be used for cosmetic purposes. Plant extracts are preferably chosen from the table of substances
    Petition 870170023194, of 04/07/2017, p. 79/150
    77/135 listed starting on page 44 of the third edition of the manual on the declaration of content of cosmetic agents, published by Kõrperpflegemittel Industrieverband und Waschmittel eV (IKW), Frankfurt. The extracts mentioned in WO 2005/123101 are also particularly advantageous.
    [00221] In preferred embodiments, a composition according to the present invention comprises one or more cosmetically acceptable vehicles selected from the group consisting of (i) (alkane) diols having 3 to 10 carbon atoms, preferably selected from the group consisting of 1,2-propylene glycol, 2-methylpropane-1,3-diol, 1,2-butylene glycol, 1,3-butanediol, 1,2 pentanediol, 1,3-pentanediol, 1,5-pentanediol, 2 , 4-pentanediol, 2-methylpentane-2,4-diol, 1,2-hexanediol, 1,6-hexanediol, 1,2-octanediol, dipropylene glycol, preferably 1,2-butylene glycol, 1,2-pentanediol and / or dipropylene glycol, and / or (ii-1) esters having 6 to 36 carbon atoms, preferably monoesters, diesters or triesters, preferably selected from the group consisting of diethyl phthalate, diethylhexyl 2,6naphthalate, isopropyl myristate, isopropyl palmitate , isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, ndecyl oleate, isooctyl stearate, isonyl stearate, isonyl isononanoate, 3,5,5-trimethylhexanoate, 3,5,5-trimethylhexylate, 2-ethylhexyl isononanoate, 2-ethylhexyl 3,5,5-trimethylhexanoate, 2-ethylhexyl 2-ethylhexanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, cetearyl ethylhexanoate, stearyl heptanoate, stearyl caprylate, 2-octyldodecyl palmitate, oleyl oleate, oleyl erucate, oleyl erateate erucyl, 2-ethylhexyl isostearate, isotridecyl isononanoate, 2-ethylhexyl cocoate, C12-15-alkyl benzoates, cetyl palmitate, triethyl citrate, triacetin (triacetyl citrate), benzyl benzoate, benzyl acetate, oils
    Petition 870170023194, of 04/07/2017, p. 80/150
    78/135 vegetables (preferably olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil) and triglycerides, in particular glyceryl stearate , glyceryl triisononanoate, glyceryl laurate or trigliderides with identical or different C6 to C10 fatty acid radicals (so-called medium chain triglycerides, in particular caprylic / capric triglyceride, such as glyceryl tricaprilate, glyceryl tricaprate), and / or ( ii-2) branched or unbranched alkyl or alkenyl alcohols, preferably selected from the group consisting of decanol, decenol, octanol, octenol, dodecanol, dodecenol, octadienol, decadienol, dodecadienol, oleyl alcohol, ricinoleyl alcohol, erucyl alcohol, alcohol stearyl, isostearyl alcohol, cetyl alcohol, lauryl alcohol, myristyl alcohol, arachidyl alcohol, linoleyl alcohol, linolenyl alcohol, hexildecanol, octyldodecanol (and particular 2-octyl-1dodecanol) and cetearyl alcohol and beenyl alcohol, and / or (ii-3) branched and unbranched waxes and hydrocarbons, linear or cyclic silicone oils and dialkyl ethers with 6 to 24 carbon atoms, preferably selected from the group consisting of jojoba oil, isoeicosane, tipprilil ether, mineral oil, petrolatum, squalane, squalene, cyclomeicone, decamethylcyclopentasiloxane, undecamethylcyclotrisiloxane, polydimethylsiloxane and poly (methylphenyl siloxane.
    [00222] In other preferred embodiments, a composition according to the present invention, comprises one or more skin care agents, preferably skin moisture retention regulators or skin repair agents, preferably selected from the group consisting of sodium lactate, urea and its derivatives, glycerol, 1,2-pentanediol, collagen, elastin or hyaluronic acid, diacila adipates, petrolatum, urocanic acid, lecithin, allantoin,
    Petition 870170023194, of 04/07/2017, p. 81/150
    79/135 panthenol, phyanthriol, lycopene, (pseudo-) ceramides [referably Ceramide 2, hydroxypropyl bispalmitamide MEA, cetyloxypropyl glyceryl methoxypropyl myristamide, (1-hexadecyl) N- (1-hexadecanoyl) -4hydroxy-hydroxy-L-proline ester palmitil oxyhydroxypropyl palmitamide], glycosphigolipids, cholesterol, phytosterols, chitosan, chondroitin sulfate, lanolin, lanolin esters, amino acids, vitamin E and its derivatives (preferably tocopherol acetate, tocopherol), alpha-hydroxy acids (preferably citric acid, lactic acid, malic acid) and its derivatives, mono-, di- and oligosaccharides, preferably glucose, galactose, fructose, mannose, levulose and lactose, poly sugars such as βglucans, in particular 1.3-1.4 β-glucan oats, alpha-hydroxy fatty acids, triterpene acids such as betulic acid or ursolic acid, and seaweed extracts, preferably selected from the group consisting of glycerol, 1,2-pentanediol, urea, hyaluronic acid, allantoin , panthenol, lanolin, alpha-hydroxy acid (preferably citric acid, lactic acid), vitamin E and its derivatives (preferably tocopherol acetate, tocopherol).
    [00223] The formulations according to the invention may also contain preservatives. The following can be used as preservatives: all antioxidants that are suitable or commonly used in cosmetic (for example, dermatological) and / or therapeutic applications, traditional preservatives (for example, formaldehyde, glutardialdehyde, parabens (for example, methyl, ethyl , propyl and butyl paraben), dibromodicytobutane, imidazolidinyl ureas (Germall), isothiazolinones (Kathon), methyl chlorothiazolidine, methyl thiazolidine, organic acids (for example, benzoic acid, sorbic acid, salicylic acid) and salts and esters thereof, propionic and formic acid and salts thereof, glycols (eg, propylene glycol, 1,2-dihydroxyalkanes), plant-based preservatives, such as, for example lantadin A, karyophylene, hesperidin, diosmin, felandrene, pigenin,
    Petition 870170023194, of 04/07/2017, p. 82/150
    80/135 quercetin, hypericin, aucubine, diosgenin, plumbago, corlilagine and the like.
    [00224] Cosmetic or therapeutic preparations, preferably topical, according to the invention also preferably contain antimicrobial active ingredients. Suitable antimicrobial assets are:
    [00225] Aryloxy-substituted, unbranched or monoalkyl- and polyalkyl-branched, saturated or mono-pentaturated fatty alcohols (up to five double or triple bonds, also mixed eno / ina compounds) Fatty alcohols, fatty aldehydes and fatty acids having chain lengths from C 2 to C 40 .
    [00226] Alkyl aryl- or aryloxy-substituted, unbranched or monoalkyl- and polyalkyl-branched, saturated or mono-pentaturated saturated diols (up to five double or triple bonds, also mixed eno / ina compounds), dialdehydes and dicarboxylic acids that have chain lengths from C 2 to C 40 , particularly preferably chain lengths from C 4 to Ο Ί2 .
    [00227] Mono- and oligoglycerides of fatty alcohols (up to 4 glycerol units) of unbranched aryl- or aryloxy-substituted fatty acids or monoalkyl- and polyalkyl-branched, saturated or mono- to pentaturated (up to five double or triple bonds) , also mixed eno / ina compounds), (mono- and oligoglycerol monoalkyl esters), fatty acids (mono- and oligoglycerol monoalkyl ethers) alkanodiols (mono- and oligoglycerol monoalkyl esters; oligoglyceryl) alkyl diethers) and dicarboxylic acids (mono- and oligoglycerol monoalkyl esters; bis (mono / oligoglyceryl) alkyl diesters), with chain lengths from C 2 to C 4 o [00228] Esters of non-branched or monoalkyl chain fatty acids - and polyalkyl-branched, saturated or mono- to pentainsaturated
    Petition 870170023194, of 04/07/2017, p. 83/150
    81/135 (up to five double or triple bonds, also mixed eno / ina compounds), optionally also aryl- or aryloxy-substituted, carboxylic acids having lengths from C 2 to C 40 with non-branched or monoalkyl- and polyalkyl- fatty alcohols branched, saturated or mono- to pentainsaturated (up to five double or triple bonds, also mixed eno / ina compounds), optionally also aryl- or aryloxy-substituted, monohydric to hexahydric having chain lengths from C 2 to C 40 .
    [00229] Cuts of fatty acids from plants and animals, containing unbranched and monoalkyl-polyalkyl-branched, saturated or mono-pentainsaturated fatty alcohols (up to five double or triple bonds, also mixed eno / ina compounds), fatty aldehydes and acids fatty acids having chain lengths from C 2 to C 40 (for example, coconut fatty acids, palm kernel fatty acids, wool wax acids).
    [00230] Lanolin mono- and oligoglycerides, lanolin alcohols and lanolic acids (eg glycerol lanolate, neocerite), glycyrrhetic acid and derivatives (eg glycyrretinyl stearate), natural and synthetic cardenolides (eg digitoxin , dogoxin, digoxigenin, gitoxigenoin, strophanthin and strophanthin), natural and synthetic bufadienolides (for example, scillaren A, scillarenin and bufotalin), sapogenins and steroidal sapogenins (for example, amirines, oleanolic acid, digitonine, gytogenin, tigogenin and dogenin) steroidal alkaloids of plant and animal origin (eg, tomatidine, solanine, solanidine, conessin, batracotoxin and homobatracotoxin). [00231] Mono- and polyhalogenated nitriles, dinitriles, trinitriles or tetranitriles.
    [00232] Mono- and oligohydroxy fatty acids having chain lengths from C 2 to C 24 (for example, lactic acid, 2-hydroximaltitic acid), oligomers and / or polymers thereof and materialsPetition 870170023194, of 07/04/2017, p. 84/150
    82/135 vegetable and animal raw materials containing these.
    [00233] Acyclic terpenes: terpene hydrocarbons (for example, ocimene, mircene), terpene alcohols (for example, geraniol, linalool, citronelol), terpene aldehydes and ketones (for example, citral, pseudoionone, beta-ionone), terpenes monocyclics: terpene hydrocarbons (for example, terpinene, terpinolene, limonene), terpene alcohols (for example, terpineol, thymol, menthol), terpene ketones (for example, pulegone, carvone); bicyclic terpenes: terpene hydrocarbons (for example, carane, pinane, bornan), terpene alcohols (for example, borneol, isoborneol), terpene ketones (for example, camphor); sesquiterpenes: acyclic sesquiterpenes (for example, farnesol, nerolidol), monocyclic sesquiterpenes (for example, bisabolol), bicyclic sesquiterpenes (for example cadinene, selinene, vetivazulene, guajazulene), tricyclic sesquiterpenes (for example, santol) ), tricyclic diterpenes (for example, abietic acid), triterpenes (for squalenoids; for example, squalene), tetraterpenes.
    [00234] ethoxylated, propoxylated or ethoxylated / propoxylated cationic fatty alcohols, fatty acids and fatty acid esters with chain lengths from C 2 to C 40 with 1 to 150 E / O and / or P / O units.
    [00235] Antimicrobial peptides and proteins that have an amino acid value of 4-200, for example, skin antimicrobial peptides (SAPs), tongue antimicrobial peptides (PAL), human beta-defensins (in particular h-BD1 and h-BD2 ), lactoferrins and their hydrolysates and peptides obtained from here, Proteins that increase Permeability / Bactericide [BPIs], cationic microbial proteins [CAPS], lysozyme.
    [00236] Very suitable carbohydrates or carbohydrate derivatives, which, in the interest of brevity, can also be included
    Petition 870170023194, of 04/07/2017, p. 85/150
    83/135 under the term carbohydrates, are compounds that contain sugars and substituted sugars or groups of sugar. Sugars also include, in particular, the deoxy and dideoxy forms, N-acetylgalactosamine, N-acetyl glucosamine and substituted sialic acid derivatives, as well as sugar esters and ethers. Preference is given to
    a) monosaccharides, including in particular pentoses and hexoses,
    b) disaccharides, including, in particular, sucrose, maltose, lactobiosis,
    c) oligosaccharides, including in particular tri- and tetrasaccarides, and
    d) polysaccharides, including, in particular, starch, glycogen, cellulose, dextran, tunicin, inulin, chitin, in particular, chitosan hydrolyzates, chitin, alginic acid and alginates, plant gums, body mucosa, pectins, mannins, xylans, galactans, arabane, polioses, chondroitin sulfates, heparin, hyaluronic acid and glycosaminoglycans, hemicelluloses, substituted cellulose and substituted starch, in particular, the hydroxyalkyl-substituted polysaccharides in each case.
    [00237] Amylose, amylopectin, xanthan gum, alpha-, beta- and gamma-dextrins are particularly suitable. Polysaccharides can consist of, for example, 4 to 1,000,000, in particular 10 to 100 mila, monosaccharides. Chain lengths are preferably chosen in each case, which ensure that the active ingredient is soluble in or can be incorporated into the particular formulation. [00238] Sphingolipids such as sphingosine, monoalkylated N-sphingosines, Ν, Ν-dialkylated sphingosines; sphingosine-1-phosphate; sphingosine-1-sulfate; psychosine (sphingosine-beta-D-galactopyranoside); sphingosyl phosphoryl choline; lisosulfatides (sphingosyl galactosyl sulfate;
    Petition 870170023194, of 04/07/2017, p. 86/150
    84/135 lysocerebroside sulfate); lecithin; sphingomyelin; sphinganin.
    [00239] The so-called natural antibacterial active ingredients can also be used, most of which are essential oils. Typical oils having an antibacterial action are, for example, anise seed oils, lemon, orange, rosemary, tarts, cloves, thyme, lavender, hops, citronella, wheat, lemon balm, cedar, cinnamon, geranium, sandalwood, violet , eucalyptus, peppermint, benzoin gum, basil, fennel, menthol and ocmea origanum, Hydastis carradensis, Berberidaceae daceae, Ratanhiae or Curcuma longa.
    [00240] Important substances that have an antimicrobial action that can be found in essential oils are, for example, anethole, catechol, camphene, carvacrol, eugenol, eucalyptol, ferulic acid, farnesol, hinokitiol, tropolone, limonene, menthol, methyl salicylate , thymol, terpineol, verbenone, berberine, curcumin, karyophylene oxide, nerolodol, geraniol.
    [00241] Mixtures of the aforementioned active systems or active ingredients and combinations of active ingredients that contain these active substances can also be used.
    [00242] The amount of antimicrobial active ingredients in the formulations is preferably 0.01 to 20% by weight, based on the total weight of the formulations, in particular preferably from 0.05 to 10% by weight.
    [00243] In another preferred embodiment, a preparation, preferably cosmetic, topical according to the present invention, additionally comprises one or more fragrance materials, preferably having a P Clog value of at least 3, preferably of at least 4, more preferably at least 5. Suitable fragrance materials are mentioned in S. Arctander, Perfume and Flavor Chemicals, vol. I and II, Montclair, N. J., 1969, self-published or H. Surburg and J. Panten, Common Fragrance and Flavor MateriPetição 870170023194, of 04/07/2017, p. 87/150
    85/135 ais, 5th Ed., Wiley-VCH, Weinheim 2006, particularly those explicitly mentioned in US 2008/0070825.
    [00244] The preparations according to the present invention advantageously comprise a total amount of 0.1 to 5% by weight, preferably 0.2 to 4% by weight, more preferably 0.25 to 3% by weight, even more preferably from 0.3 to 2.5% by weight, of the one or more (preferably) fragrance materials, in each case, based on the total weight of the preparation.
    [00245] In another preferred embodiment, a preparation, preferably a product without cosmetic rinse, according to the present invention additionally comprises one or more of the fragrance materials that have a boiling point of 250 ° C or higher (a 1013 mbar). The total amount of fragrance materials having a boiling point of 250 ° C or higher (at 1013 mbar) is preferably at least 10% by weight, more preferably at least 20% by weight, based on the total amount of materials fragrances present in a preparation according to the present invention.
    [00246] More preferably, fragrance materials, preferably having a boiling point of 250 0 C or above 1013 mbar, are selected from (here, in some cases, the names of normal industrial products and registered trademarks from several firms are given):
    [00247] alpha-amyl cinnamic aldehyde, alpha-hexyl cinnamic aldehyde, 2phenoxyethylisobutyrate (Phenirat), methyl dihydrojasmonate [referably with a cis-isomer content of> 60 by weight (Hedione, Hedione HC)], 4,6 , 6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta [g] benzopyran (Galaxolide), benzylsalicylate, 2-methyl-3 (4-tert-butyl-phenill) propanal ( Lilial), 4,7-methane3a acetate, 4,5,6,7,7a-hexahydro-5-indenyl and / or 4,7-methane acetatePetition 870170023194, of 04/07/2017, p. 88/150
    86/135
    3a, 4,5,6,7,7a-hexahydro-6-indenyl (Herbaflorat), styryl acetate (1-phenylethyl acetate), octahidro-2,3,8,8-tetramethyl-2-acetonephton and / or 2-acetyl-1,2,3,4,6,7,8-octahydro-2,3,8,8-tetramethylnaphthaline (Iso E Super), hexylsalicylate, 4-tert-butylcyclohexyl acetate (Oryclon ), 2-tert-butylcyclohexyl acetate (Agrumex HC), alpha-ionone (4- (2,2,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one), carboxaldehyde of 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene (Lyral), (E) -e / or (Z) -3methylcyclopentadec-5-enone (Muscenone), 15-pentadec-11-enolide and / or 15-pentadec-12-enolide (Globalide), 15-cyclopentadecanolide (Macrolide), 1 - (5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2naphthalenyl) ethanone (Tonalide ), ethylene brassylate, 2-ethyl-4- (2,2,3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol (Sandranol), alpha-Santalol, 2,2-dimethyl-3- ( 3-methylphenyl) -propanol (Majantol), allyl heptanoate, 4methylacetophenone, (4aR, 5R, 7aS, 9R) -octahidro-2,2,5,8,8,9a-hexamethyl4H-4a, 9-methanazulene (5, 6-d) -1,3-dioxol) (Ambroce nide), Timberol (1 (2,2,6-trimethylcyclohexyl) hexan-3-ol), benzylacetone, methyl cinnamate, 3a, 6,6,9a-tetramethyldodecahydronaphth [2,1-b] furan (Ambroxid) .
    [00248] Cosmetic or pharmaceutical preparations containing one or more compounds of formula (I) can, in particular, whether crystalline or microcrystalline solid bodies such as, for example, inorganic micropigments are to be incorporated into the preparations, according to the invention also contain surfactants anionic, cationic, non-ionic and / or amphoteric mentioned in WO 2005/123101.
    [00249] Anionic surfactants generally have carboxylate, sulfate or sulfonate groups as functional groups. In aqueous solution, negatively charged organic ions form in the acid or neutral environment. Cationic surfactants are almost exclusively characterized by the presence of a quaternary ammonium group. In aqueous solution they form positively charged organic ions in the acid or neutral environment. Amphoteric surfactants contain both
    Petition 870170023194, of 04/07/2017, p. 89/150
    87/135 anionic and cationic groups and, therefore, behave in an aqueous solution in the same way as anionic or cationic surfactants, according to pH. They have a positive charge in a strongly acidic environment and a negative charge in an alkaline environment. In the range from neutral pH, on the other hand, they are zwitterionic. Polyether chains are typical of nonionic surfactants. Nonionic surfactants do not form ions in the aqueous medium.
    A. Anionic surfactants [00250] Anionic surfactants that can advantageously be used are acyl amino acids (and salts thereof), such as
    - acyl glutamates, for example acyl sodium glutamate, di-TEA-palmitoyl aspartate and caprylic / capric sodium glutamate,
    - acyl peptides, for example, palmitoyl hydrolyzate milk protein, hirolized coconut soy protein and sodium / potassium coconut hydrolyzed collagen,
    - sarcosinates, for example myristoil sarcosine, TEA-lauroyl sarcosinate, sodium lauroyl sarcosinate and sodium cocoyl sarcosinate,
    - taurates, for example sodium lauryl taurate and sodium methyl cocoyl taurate,
    - acyl lactylates, lauroyl lactylate, caproyl lactylate
    - alaninates [00251] carboxylic acids and derivatives, such as [00252] for example lauric acid, aluminum stearate, magnesium alkanolate and zinc undecylenate,
    - carboxylic acid ester, eg calcium stearoyl lactylate, lauret-6 citrate and PEG-4 sodium lauramide carboxylate,
    - ether of carboxylic acids, for example carboxylate
    Petition 870170023194, of 04/07/2017, p. 90/150
    88/135 sodium lauret-13 and PEG-6 sodium cocamide carboxylate, [00253] phosphoric acid esters and salts, such as, for example DEA-olet-10-phosphate and dilauret-4 phosphate, [00254] sulfonic acids and salts, such as
    - acyl isothionates, for example sodium / ammonium cocoyl isothionate,
    - alkyl aryl sulfonates,
    - alkyl sulfonates, for example sodium cocomonoglyceride sulphate, C12-14 sodium olefin sulphonate, sodium lauryl sulfoacetate and PEG-3 cocamide magnesium sulphate,
    - sulfosuccinates, for example sodium dioctyl sulfosuccinate, sodium laureth sulfosuccinate, sodium lauryl sulfosuccinate and MEA disodium sulfosuccinate undecylenamido, and
    [00255] sulfuric acid esters, such as
    - alkyl ether sulfate, for example sodium, ammonium, magnesium, MIPA, TIPA lauret sulfate, sodium miret sulfate and sodium C12-13 paret sulfate, [00256] alkyl sulfates, for example sodium, ammonium and TEA lauryl sulfate.
    B. Cationic surfactants [00257] Cationic surfactants that can advantageously be used are
    - alkyl amines,
    - alkyl imidazoles,
    - ethoxylated amines and
    - quaternary surfactants.
    RNH2CH2CH2COO- (where pH = 7)
    RNHCH2CH2COO- B + (where pH = 12) B + = any cation, for example Na +
    Petition 870170023194, of 04/07/2017, p. 91/150
    89/135
    - esterquats [00258] Quartenary surfactants contain at least one N atom, which is covalently linked to 4 alkyl or aryl groups. This leads to positive caverns, regardless of pH. Alkyl betaine, alkyl amidopropyl betaine and alkyl amidopropyl hydroxysulfaine are advantageous. The cationic surfactants used can also preferably be chosen from the group of quaternary ammonium compounds, in particular benzyl trialkyl ammonium chlorides or bromides, such as benzyl dimethilstearyl ammonium chloride for example, also trialkyl ammonium alkyl salts, for example cetyl chloride trimethyl ammonium or bromide, alkyl dimethyl hydroxyethyl ammonium chlorides or bromides, dialkyl dimethyl ammonium chlorides or bromides, alkyl amide ether sulfates, ethyl trimethyl ammonium, alkyl pyridinium salts, for example lauryl chloride or pyrimidinium cetyl, imidazoline derivatives compounds having a cationic character such as amine oxides, for example alkyl dimethyl amine oxides or alkyl aminoethyl dimethyl amine oxides. Trimethyl ammonium cetyl salts are particularly and advantageously used.
    C. Amphoteric surfactants [00259] Amphoteric surfactants which can advantageously if used are [00260] acyl / dialkyl ethylene diamine, for example sodium acyl amfoacetate, disodium acyl amphodipropionate, disodium alkyl amphodiacetate, sodium acylamfohydroxypropyl sulfonate, acyl ammonium acetate and acyl ammonium acetate sodium, [00261] N-alkyl amino acids, for example aminopropyl alkyl glutamide, alkyl aminopropionic acid, sodium alkyl imidodipropionate and lauroamfocarboxyglycinate.
    D. Non-anionic surfactants [00262] Non-anionic surfactants that can advantageously if used are
    Petition 870170023194, of 04/07/2017, p. 92/150
    90/135
    - alcohols,
    - alkanolamides, such as MEA / DEA / MIPA cocamides,
    - amine acids, such as cocamidopropylamine oxide oxide,
    - esters produced by esterification of carboxylic acids such as ethylene oxide, glycerol, sorbitan or other alcohols,
    - ethers, for example ethoxylated / propoxylated alcohols, ethoxylated / propoxylated esters, glycerol ethoxylated / propoxylated esters, ethoxylated / propoxylated cholesterols, ethoxylated ethoxylated ethoxylates, propylated ethoxylates and polysilated ethoxylates such as lauryl glucoside, decyl glycoside and cocoglycoside,
    - sucrose esters, ethers,
    - polyglycerol esters, diglycerol esters, monoglycerol esters,
    - glucose methyl esters, hydroxy acid esters.
    [00263] The use of a combination of anionic and / or amphoteric surfactants, with one or more nonionic surfactants is also advantageous.
    [00264] The surface active substance (surfactant), or the combination of surface active substances can be present in the formulations according to the invention in a concentration comprised between 1 and 98% by weight, based on the total weight of the formulations.
    [00265] Cosmetic (e.g., dermatological) or pharmaceutical formulations according to the invention containing one or more compounds according to the invention, or for use according to the invention having formula (I) can also take the form of emulsions.
    [00266] The oil phase of the preparations according to the invention,
    Petition 870170023194, of 04/07/2017, p. 93/150
    91/135 which contain one or more compounds of formula (I) can advantageously be selected from the groups of substances mentioned in WO 2005/123101.
    [00267] The oil phase (lipid phase) in the formulations according to the invention (in particular topical cosmetic formulations) can advantageously be selected from the following group of substances:
    - Mineral oils (advantageously paraffin oil), mineral waxes
    - fatty oils, fats, waxes and other bodies of natural and synthetic fats, preferably esters of fatty acids with low C alcohols, for example, with isopropanol, propylene glycol or glycerin, or fatty alcohol esters with low alkanoic acids C number or with fatty acids;
    - alkyl benzoates (for example, mixtures of n-dodecyl, ntridecyl, n-tetradecyl or n-pentadecyl benzoate);
    - cyclic or linear silicone oils, such as dimethyl polysiloxanes, diethyl polysiloxanes, diphenyl polysiloxanes and mixed forms thereof. Esters (natural or synthetic) are advantageously used, in particular (a) esters of branched and / or unbranched saturated and / or unsaturated alkane carboxylic acids having a chain of 3 to 30 C atoms and saturated and / or unsaturated alcohols, branched and / or unbranched alcohols having a chain length of 3 to 30 C atoms, (b) esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 C atoms. Preferred ester oils are isopropyl myristate, isopropyl palmitate, deisopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl laurate, n-decyl oleate, isooctyl stearate, isonyl stearate , isonyl isononanoate, 3,5,5-trimethylhexi 1-3,5,5-trimethylhexanoate, 2-ethylhexyl isononanoate, 2-ethylhexi 1-3,5,5Petition 870170023194, from 04/07/2017, p. 94/150
    92/135 trimethylhexanoate, 2-ethylhexyl-2-ethylhexanoate, cetearyl-2-ethylhexanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2hexyldecyl stearate, 2-octyldecyl palmitate, 2-octylodecyl palmitate, 2-octyldehyde palate , oleyl erucate, erucyl oleate, erucyl erucate and synthetic, semi-synthetic and natural mixtures of such esters, for example jojoba oil.
    [00268] The oil phase can also be advantageously chosen from the group consisting of branched and unbranched hydrocarbons and hydrocarbon waxes, silicone oils, dialkyl ethers, group consisting of saturated or unsaturated, branched or unbranched alcohols, and of triglycerides of fatty acids, in particular, the triglycerol esters of alkanes of saturated and / or unsaturated carboxylic acids, branched and / or unbranched, with a chain length of 8 to 24, in particular 12 to 18 C atoms. Fatty acid triglycerides can be advantageously selected from the group of synthetic, semi-synthetic and natural oils, for example, caprylic or capric acid triglycerides, apricot seed oil, avocado oil, cotton seed oil, seed oil borage, thistle oil, peanut oil, gamma-oryzanol, rosehip seed oil, hemp oil, hazelnut oil, blackcurrant seed oil, oil coconut oil, cherry seed, salmon oil, linseed oil, corn oil, macadamia oil, almond oil, evening primrose oil, mink oil, olive oil, palm oil, palm kernel oil, walnut oil pecan, peach kernel oil, pistachio oil, rapeseed oil, rice bran oil, castor oil, safflower oil, sesame oil, soybean oil, sunflower oil, teatree oil, seed oil grape or wheat germ oil, and the like. Any mixtures of oil and wax components can also be used advantageously. In some cases it is also advantageous to use waxes,
    Petition 870170023194, of 04/07/2017, p. 95/150
    93/135 for example, cetyl palmitate, as the only lipid component of the oily phase, the oil phase advantageously be chosen from the group consisting of 2-ethylhexyl isostearate, octyl dodecanol, isotridecyl isononanoate, isoeicosane, cocoate of 2 -ethylhexyl, C12-15-alkyl benzoate, caprylic-capric acid triglyceride and tippryl ether. Mixtures of C12-15-alkyl benzoate and 2-ethylhexyl isostearate, mixtures of C12-15alkyl benzoate and isotridecyl isononanoate isononanoate and mixtures of C12-15-alkyl benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate are particularly advantageous. Hydrocarbon paraffin oil, squalane and squalene can also be advantageously used. The oil phase can advantageously also have a content of cyclic or linear silicone oils or consist entirely of such oils, but it is preferable, however, to use an additional content of other oil phase components, together with the silicone oil or silicone oils. Cyclomethicone (for example, decamethylcyclopentasiloxane) can advantageously be used as silicone oil. Other silicone oils can also be used advantageously, however, for example undecamethyl cyclotrisiloxane, polydimethyl siloxane and poly (methylphenyl siloxane). Mixtures of cyclomethicone and isotridecyl isononanoate and cyclomethicone of e 2-ethylhexyl isostearate are also particularly advantageous.
    [00269] The aqueous phase of the formulations according to the invention (in particular topical cosmetic formulations), in the form of an emulsion can advantageously include: alcohols, diols or polyols having a low C number and ethers thereof, preferably ethanol , isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, monomethyl propylene glycol, monomethyl or monobutyl ether, monomethyl diethylene glycol or mono ethyl ether and the like, also alcohols having a low C number, for example, ethanol , isopropanol, 1,2-propanediol, glycerol and, in particular one or more
    Petition 870170023194, of 04/07/2017, p. 96/150
    94/135 thickeners, which can advantageously be chosen from the group comprising silicon dioxide, aluminum silicates, such as, for example, bentonites, polysaccharides or their derivatives, for example, hyaluronic acid, guar gum, xanthan gum, hydroxypropylmethyl cellulose, or allulose derivatives, particularly advantageously from the group of polyacrylates, preferably a polyacrylate from the group of so-called carbopols, for example carbopols type 980, 981, 1382, 2984, 5984, individually or in combination, or from the group of polyurethanes, also alpha- or beta-hydroxy acids, preferably lactic acid, citric acid or salicylic acid, also emulsifying agents, which can be advantageously selected from the group of ionic, non-ionic, polymeric, emulsifiers containing phosphate and zwitterionics.
    [00270] Formulations according to the present invention in the form of an emulsion advantageously include one or more emulsifying agents. O / W emulsifiers, for example, can be advantageously chosen from the group of polyethoxylated or polypropoxylated or polyethoxylated and polypropoxy products, for example:
    - Fatty alcohol ethoxylates,
    - Wool wax ethoxylated alcohols,
    - Polyethylene glycol ethers having the general formula R-O- (CH2-CH2-O-) n-R ',
    - Fatty acid ethoxylates having the general formula R-COO (-CH2-CH2-O-) n -H,
    - Etoxylated etherified fatty acids with the general formula
    R-COO - (- CH2-CH2-O-) n -R ',
    - Ethoxylated fatty acids esterified with the general formula
    R-COO - (- CH2-CH2-O-) n -C (O) -R ',
    Petition 870170023194, of 04/07/2017, p. 97/150
    95/135
    - Polyethylene glycol glycerol fatty acid esters,
    - ethoxylated sorbitan esters,
    - Cholesterol ethoxylates,
    - ethoxylated triglycerides,
    - Carboxylic acid alkyl ether with the general formula R-COO - (- CH2-CH2-O-) n -OOH, where n represents a number from 5 to 30,
    - Polyoxyethylene sorbitol fatty acid esters,
    - alkyl ether sulphates having the general formula RO - (- CH2CH2-O-) n -SO3-H,
    - Fatty alcohol propoxylates that have the general formula RO - (- CH2-CH (CH3) -O-) n -H,
    - Polypropylene glycol ethers having the general formula RO - (- CH2-CH (CH3) -O-) n -R ',
    - Propoxylated alcohols of wool wax,
    - R-COO etherified fatty acid propoxylates - (- CH2CH (CH3) -O-) n -R ',
    - Fatty acid propoxylates esterified having the general formula
    R-COO - (- CH2-CH (CH3) -O-) n -C (O) -R ',
    - Fatty acid propoxylates having the general formula R-COO - (- CH2-CH (CH3) -O-) n -H,
    - Polypropylene glycol glycerol fatty acid esters,
    - Sorbitan propoxylated esters,
    - Cholesterol propoxylates,
    - Propoxylated triglycerides,
    - alkyl ether of carboxylic acids having the general formula RO - (- CH2-CH (CH3) -O-) n -CH2-COOH,
    - Sulfates of alkyl ether or the acids in which they sulfaPetition 870170023194, of 07/04/2017, p. 98/150
    96/135 tos are based on [00271] having the general formula RO - (- CH2-CH (CH3) -O-) n -SO3-H,
    - Fatty alcohol ethoxylates / propoxylates that have the general formula ROX n -Ym-H,
    - Polypropylene glycol ethers having the general formula RO-X n Ym-R ',
    - Etherified fatty acid propoxylates having the general formula R-COO-X n -Y m -R
    - Fatty acid ethoxylates / propoxylates having the general formula R-COO-X n -Y m -H.
    [00272] Particularly advantageous according to the invention, the polyethoxylates or polypropoxylates or O / W polyethoxylated and polypropoxylated emulsifiers used are chosen from the group of substances having HLB values from 11 to 18, more particularly advantageous having HLB values of 14.5 to 15.5, if the O / W emulsifiers have saturated radicals unsaturated R and / or R '. If the O / W emulsifiers have unsaturated R and / or R 'radicals, or if isoalkyl derivatives are present, the preferred HLB value of such emulsifiers may also be higher or lower.
    [00273] It is advantageous to choose fatty alcohol ethoxylates from the group of stearyl alcohol ethoxylates, cetyl alcohol, cetylstearyl alcohols (cetearyl alcohols). Particularly preferred are:
    [00274] polyethylene glycol stearyl ether (n) (stearet-n), where n = 1320, [00275] polyethylene glycol ether (n) (cetet-n), where n = 13-20, [00276] isocetyl polyethylene glycol ether (n) (isocetet-n), where n = 1320, [00277] polyethylene glycol ether (n) (ceteareto-n), where n = 13-20, [00278] polyethylene isostearyl ether glycol (m) (isostearet-m) in which
    Petition 870170023194, of 04/07/2017, p. 99/150
    97/135 m = 12-20, [00279] oleyl polyethylene glycol ether (k) (oleth-k), where k = 12-15, [00280] polyethylene glycol ether (12) (laureth-12), [00281] isolauryl polyethylene glycol ether (12) (isolauret-12).
    [00282] It is also advantageous to choose the fatty acid ethoxylates from the following group:
    [00283] polyethylene glycol stearate (n), where n = 20-25, [00284] polyethylene glycol isostearate (m) where m = 12-25, [00285] polyethylene glycol oleate (k), where k = oleate 12-20.
    [00286] Sodium carboxylate laureth-11 can advantageously be used as the ethoxylated alkyl carboxylic acid ether or a salt thereof. Sodium laureth sulfate 1-4 can be advantageously used as the alkyl ether sulfate. Cholesteryl ether of polyethylene glycol (30) can be advantageously used as the derivative of ethoxylated cholesterol. Polyethylene glycol soy sterol (25) was revealed.
    [00287] Evening primrose polyethylene glycol glycerides (60) can advantageously be used as ethoxylated triglycerides.
    [00288] It is also advantageous to choose polyethylene glycol glycerol fatty acid esters from the group comprising glyceryl polyethylene glycol laurate (n), where n = 20-23, glyceryl caprate / polyethylene glycol caprinate (6), glyceryl polyethylene glycol oleate (20), glyceryl polyethylene glycol isostearate (20), glyceryl oleate / polyethylene glycol cocoate (18).
    [00289] It is also beneficial to choose sorbitan esters from the group comprising polyethylene glycol sorbitan monolaurate (20), polyethylene glycol sorbitan monostearate (20), polyethylene glycol sorbitan monostearate (20), sorbitan monopalmitate polyethylene glycol (20), polyethylene glycol sorbitan monooleate (20).
    [00290] The following can be used as emulsifiers W /
    Petition 870170023194, of 04/07/2017, p. 100/150
    98/135
    Advantageous: fatty alcohols having 8 to 30 carbon atoms, saturated and / or unsaturated monoglycerol esters, branched and / or unbranched carboxylic acid alkanes having a chain length of 8 to 24, in particular 12 to 18 carbon atoms C, diglycerol esters of alkanes of saturated and / or unsaturated, branched and / or unbranched carboxylic acids having a chain length of 8 to 24, in particular 12 to 18 C atoms, saturated alcohol monoglycerol ethers and / or unsaturated branched and / or unbranched having a chain length of 8 to 24, in particular 12 to 18 C atoms, diglycerol ethers of saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 8 to 24, in particular 12 to 18 C atoms, propylene glycol esters of saturated and / or unsaturated, branched and / or unbranched carboxylic acid alkanes having a chain length of 8 to 24, in particular 12 to 18 atoms of C, and this sorbitan residues of saturated and / or unsaturated, branched and / or unbranched alkanes of carboxylic acids having a chain length of 8 to 24, in particular 12 to 18 C atoms.
    [00291] Particularly advantageous W / O emulsifiers are emulsifiers of glyceryl monostearate, glyceryl monostearate, glyceryl monomyristate, glyceryl monooleate, diglyceryl monostearate, diglycerol propylene glycol monoestearate, propylene glycol mono stearate, propylene glycol mono stearate, propylene glycol monolaurate, sorbitan monoisearearate, sorbitan monolaurate, sorbitan monocaprilate, sorbitan monoiso-oleate, sucrose distearate, cetyl alcohol, stearyl alcohol, arachidyl alcohol, beyl alcohol, isobenyl alcohol, stearyl alcohol, selacayl alcohol polyethylene glycol ether (stearet-2), glyceryl monolaurate, glyceryl monocaprinate, glyceryl monocaprilate.
    Petition 870170023194, of 04/07/2017, p. 101/150
    99/135 [00292] The formulations according to the invention (in particular, cosmetic, including dermatological formulations) may contain deodorants, that is, the active ingredients that have a deodorizing and sweating inhibiting action. These include, for example, odor maskers, such as constituents of common perfumes, aluminum-based antiperspirants, zirconium or zinc salts, odor absorbers, for example, the layered silicates described in DE-P 40 09 347, in particular, montmorillonite, kaolinite, nontronite, saponite, hectorite, bentonite, smectite, and also zinc salts of ricinoleic acid, for example. They also include bactericidal or bacteriostatic substances, such as deodorants for example, hexachlorophene, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (Irgasan), 1,6-di- (4-chlorophenillbiguanide) hexane (chlorohexidine ), 3,4,4'trichlorocarbanilide, and the active agents described in the patent specifications open to the public DE-37 40 186, DE-39 38 140, DE-42 04 321, DE-42 29 707, DE-42 29 737, DE-42 37 081, DE-43 09 372, DE -43 24 219 and containing cation active substances, such as, for example, quaternary ammonium salts and odor absorbers, such as, for example, Grillocin ® (combination zinc ricinoleate and various additives) or triethyl citrate, optionally in combination with ion exchange resins.
    [00293] The amount of deodorizing and / or antiperspirant active ingredients in the formulation is preferably 0.01 to 20.% by weight, based on the total weight of the formulations, in particular preferably 0.05 to 10%. .
    [00294] Preferred modalities and other aspects of the present invention emerge from the appended claims and from the following examples.
    [00295] The examples describe the invention in more detail, without limiting the protection area of the claims. Unless otherwise indicated
    Petition 870170023194, of 04/07/2017, p. 102/150
    100/135 otherwise, all data, in particular quantities and percentages, refer to weight.
    Examples 1: Synthesis of compounds of formula (I)
    Example 1.1: Butylcarbamic acid (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester (BIO1267) [00296] 66.6 g of menthyl chloroformate (70% in toluene) a mixture of 16.6 g of pyridine and 21.9 g of n-butylamine in 100 ml of toluene was added at 0 ° C over a period of 50 minutes. After stirring for 12 hours at room temperature, 100 ml of 2M HCl and then 50 ml of water were added, the phases were separated and the aqueous phase discarded. After washing with saturated NaHCO3 solution and water the organic phase was dried and evaporated to produce 55.1 g of crude product which was recrystallized from 30 g of n-heptane, to give 34.5 g of the analytically pure product , as white crystals, 1H-NMR (400 MHz, CDCI 3 , TMS): δ = 4.57 (m, H), 4.54 (d, t, 4.1 Hz, 10.8 Hz, H), 3.16 (m, 2 H), 2.04 (d, 11.7 Hz, H), 1.92 (d, q, q, 2.3 Hz, 6.9 Hz, 6.9 Hz, H ), 1.66 (m, 2 H), 1.47 (m, 3 H), 1.24-1.39 (m, 3 H), 1.06 (m, H),, 081-0, 99 (m, 2 H), 0.92 (t, 7.3 Hz, 3 H), 0.90 (d, 6.5 Hz, 3 H), 0.89 (d, 7.0 Hz, 3 H), 0.79 (d, 6.9 Hz, 3 H) ppm.
    [00297] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 156.5 (s), 74.3 (d),
    47.8 (d), 41.6 (t), 40.7 (t), 34.4 (t), 32.1 (t), 31.4 (d), 26.3 (d), 23 , 6 (t),
    22.1 (q), 20.8 (q), 19.9 (t), 16.5 (q), 13.7 (q) ppm.
    [00298] MS (El): m / z = 255 (<1), 254 (<1), 138 (83), 118 (100), 95 (88), 83 (83), 69 (33), 55 (53), 41 (39), 29 (20).
    Example 1.2: Ethylcarbamic acid (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester (BIO1151) [00299] 58.7 g of menthyl chloroformate (80% in toluene) 16.6 g of pyridine and 150 ml ethylamine (2M solution in THF) in 100 ml toluene at 0Ό were added to the mixture over a period of 30
    Petition 870170023194, of 04/07/2017, p. 103/150
    101/135 minutes. After stirring for 12 hours at room temperature, 100 ml of 2M HCI and subsequently 50 ml of water were added, the phases separated and the water phase discarded. After washing with saturated NaHCO3 solution and water the organic phase was dried and evaporated to yield 47.1 g of crude product which was recrystallized from 82.4 g of n-heptane to give 24.4 g of the analytically pure product as white crystals.
    [00300] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 4.54 (d, t, 4.3 Hz, 10.8 Hz, H), 4.54 (m, H), 3 , 20 (q, 6.9 Hz, 2 H), 2.05 (m, H), 1.92 (d, q, q, 2.7 Hz, 7.0 Hz, 7.0 Hz, H) , 1.61 to 1.71 (m, 2 H), 1.48 (m, H), 1.30 (m, H), 1.13 (t, 7.2 Hz, 3 H), 1, 06 (m, H), 0.82-0.99 (m, 2 H), 0.90 (d, 6.6 Hz, 3 H), 0.89 (d, 7.0 Hz, 3 H) , 0.79 (d, 7.0 Hz, 3 H) ppm.
    [00301] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 156.4 (s), 74.3 (d),
    47.5 (d), 41.5 (t), 35.8 (t), 34.4 (t), 31.4 (d), 26.3 (d), 23.6 (t), 22.1 (q),
    20.8 (q), 16.5 (q), 15.3 (q) ppm.
    [00302] MS (El): m / z = 228 (<1), 227 (not detected), 138 (82), 123 (42), 95 (100), 90 (71), 81 (75), 71 (49), 55 (49), 41 (52), 29 (33). [00303] The menthol carbamates according to examples 1.3 to 1.20 were produced in a similar way to the methodology described in example 1.1. and example 1.2.
    Example 1.3: (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of cyclohexyl-carbamic acid (BIO1266) [00304] 1 H-NMR (400 MHz, CDCI 3 , TMS ): δ = 4.54 (d, t, 4.0 Hz, 11.0 Hz, H), 4.47 (m, H), 3.46 (m, H), 2.04 (d, 12 , 0 Hz, H), 1.87-1.97 (m, 3 H), 1.56-1.74 (m, 5 H), 1.48 (m, H), 1.33 (m, 3 H), 1.11 (m, 4 H), 0.93 (m, H), 0.90 (d, 6.6 Hz, 3 H), 0.89 (d, 7.0 Hz, 3 H), 0.84 (m, H), 0.79 (d, 7.0 Hz, 3 H) ppm.
    [00305] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 155.7 (s), 74.1 (d), 49.7 (d), 47.5 (d), 41.6 (t), 34.4 (t), 33.5 (t), 33.5 (t), 31.4 (d), 26.3 (d),
    25.6 (t), 24.8 (t), 24.8 (t), 23.6 (t), 22.1 (q), 20.8 (q), 16.5 (q) ppm.
    Petition 870170023194, of 04/07/2017, p. 104/150
    102/135 [00306] MS (El): m / z = 282 (<1), 281 (<1), 144 (87), 138 (65), 95 (49), 83 (100), 69 (37 ), 55 (67), 41 (36).
    Example 1.4: (2R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester (2-ethoxy-phenyl) -carbamic acid (B101632) [00307] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 8.11 (m, H), 7.18 (m, H), 6.94 (m, 2 H), 6.84 (m, H), 4.69 (d , t, 4.4 Hz, 10.8 Hz, H), 4.09 (q, 7.0 Hz, 2 H), 2.12 (d, 12.1 Hz, H), 2.00 (d , q, q, 2.8 Hz, 7.0 Hz, H), 1.70 (m, 2 H), 1.54 (m, H), 1.46 (t, 7.0 Hz, 3 H ), 1.41 (m, H), 1.09 (m, H),
    I, 04 (d, t, 11.1 Hz, 12.1 Hz, H), 0.92 (d, 7.0 Hz, 3 H), 0.92 (d, 6.5 Hz, 3 H) , 0.88 (m, H), 0.82 (d, 6.9 Hz, 3 H) ppm.
    [00308] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 153.3 (s), 146.7 (s), 128.0 (s), 122.4 (d), 121.0 (d), 118.1 (d), 110.9 (d), 74.9 (d), 64.1 (t),
    47.3 (d), 41.4 (t), 34.3 (t), 31.4 (d), 26.2 (d), 23.5 (t), 22.1 (q), 20.8 (q),
    16.4 (q), 14.9 (q) ppm.
    [00309] MS (El): m / z = 320 (6), 319 (31), 181 (67), 137 (100), 108 (40), 83 (86), 69 (35), 55 (51 ), 41 (24).
    Example 1.5: (2R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester (2-acetyl-phenyl) -carbamic acid (B101633) [00310] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 11.1 (m, H), 8.51 (d,
    8.6 Hz, H), 7.87 (d, 8.0 Hz, H), 7.53 (d, d, 8.5 Hz, 7.2 Hz, H), 7.05 (d, d ,
    7.2 Hz, 8.0 Hz, H), 4.65 (d, t, 4.4 Hz, 10.8 Hz, H), 2.66 (s, 3 H), 2.10 (d,
    II, 9 Hz, H), 1.99 (d, q, q, 2.7 Hz, 6.9 Hz, 6.9 Hz, H), 1.69 (m, 2 H), 1.52 ( m, H), 1.43 (t, 10.9 Hz, H), 1.09 (m, H), 1.06 (d, t, 11.1 Hz, 12.0 Hz, H), 0 , 92 (d, 6.5 Hz, 3 H), 0.91 (d, 7.0 Hz, 3 H), 0.88 (m, H), 0.81 (d, 6.9 Hz, 3 H) ppm.
    [00311] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 202.3 (s), 153.8 (s),
    141.7 (s), 135.0 (d), 131.7 (d), 121.4 (s), 121.1 (d), 119.2 (d), 75.1 (d),
    47.1 (d), 41.2 (t), 34.3 (t), 31.5 (d), 28.6 (q), 26.2 (d), 23.6 (t), 22 , 1 (q),
    20.8 (q), 16.5 (q) ppm.
    [00312] MS (El): m / z = 318 (2), 317 (11), 135 (100), 120 (25), 83
    Petition 870170023194, of 04/07/2017, p. 105/150
    103/135 (83), 69 (31), 55 (45), 43 (27).
    Example 1.6: (1R, 2S, 5R) Benzyl-carbamic acid -2-isopropyl-5-methyl-cyclohexyl ester (BIO1695) [00313] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 7.34 (m, 3 H), 7.28 (m,
    H), 7.27 (m, H), 4.89 (m, H), 4.59 (d, t, 4.4 Hz, 10.9 Hz, H), 4.37 (m, 2 H ), 2.07 (d, 12.1 Hz, H), 1.93 (m, H), 1.66 (m, 2 H), 1.49 8m, H), 1.31 (t, t , 3.0 Hz, 10.8 Hz, H), 1.06 (m, H), 0.96 (d, t, 11.0 Hz, 12.0 Hz, H), 0.90 (d, 6.6 Hz, 3 H), 0.89 (d, 7.1 Hz, 3 H), 0.85 (m, H), 0.80 (d, 7.1 Hz,
    H) ppm.
    [00314] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 156.5 (s), 138.8 (s),
    128.6 (d), 18.6 (d), 127.5 (d), 127.4 (d), 127.4 (d), 74.8 (d), 47.4 (d), 45 , 0 (t), 41.5 (t), 34.3 (t), 31.4 (d), 26.3 (d), 23.6 (t), 22.1 (q), 20, 8 (q),
    16.5 (q) ppm.
    [00315] MS (El): m / z = 290 (<1), 289 (1), 150 (100), 138 (27), 123 (11), 106 (10), 91 (37), 69 ( 16), 55 (21), 41 (13).
    Example 1.7: (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of cyclohexylmethyl-carbamic acid (B101699) [00316] 1 H-NMR (400 MHz, CDCI 3 , TMS ): δ = 4.61 (m, H), 4.54 (d, t,
    4.3 Hz, 10.8 Hz, H), 3.00 (m, 2 H), 2.04 (d), 12.1 Hz, H), 1.92 (d, q, q,
    2.5 Hz, 7.0 Hz, 7.0 Hz, H), 1.69 (m, 7 H), 1.46 (m, 2 H), 0.81-1.33 (m, 9 H), 0.85 (d, 6.6 Hz, 3 H), 0.89 (d, 7.0 Hz, 3 H), 0.79 (d, 7.0 Hz, 3 H) ppm.
    [00317] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 156.6 (s), 74.3 (d),
    47.5 (d), 47.2 (t), 41.6 (t), 38.3 (d), 34.4 (t), 31.4 (d), 30.7 (t), 30.7 (t),
    26.4 (t), 26.3 (d), 25.9 (t), 25.8 (t), 23.6 (t), 22.1 (q), 20.8 (q), 16 , 5 (q) ppm.
    [00318] MS (El): m / z = 296 (<1), 295 (<1), 158 (100), 138 (95), 123 (17), 95 (42), 83 (57), 69 (18), 55 (39), 41 (21).
    Example 1.8: (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester (tetrahydro-furan-2-ylmethyl) -carbamic acid (B101702)
    Petition 870170023194, of 04/07/2017, p. 106/150
    104/135 [00319] main signs of isomeric mixtures:
    [00320] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 4.94 (m, H), 4.54 (t, 9.9 Hz, H), 3.96 (m, H) , 3.85 (t, d, 6.5 Hz, 8.4 Hz, H), 3.74 (d, d, d, 2.6 Hz,
    6.8 Hz, 8.2 Hz, H), 3.42 (m, H), 3.15 (d, d, d, 5.4 Hz, 6.8 Hz, 12.1 Hz, H), 2.03 (d, 12.1 Hz, H), 1.93 (m, 4 H), 1.66 (m, 2 H), 1.56 (m, H), 1.48 (m, H ), 1.30 (t, 11.4 Hz, H), 1.06 (m, H), 0.94 (d, t, 10.9 Hz, 12.0 Hz, H), 0.90 ( d, 6.6 Hz, 3 H), 0.89 (d, 7.0 Hz, 3 H), 0.84 (m, H), 0.79 (d, 6.9 Hz, 3 H) ppm .
    [00321] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 156.7 (s), 78.0 (d),
    74.5 (d), 68.1 (t), 47.4 (d), 44.7 (t), 41.5 (t), 34.3 (t), 31.3 (d), 28.4 (t),
    26.2 (d), 25.9 (t), 23.6 (t), 22.1 (q), 20.8 (q), 16.5 (q) ppm.
    [00322] MS (El): m / z = 285 (<1), 284 (1), 139 (33), 102 (18), 83 (46), 71 (100), 55 (21), 43 ( 25).
    Example 1.9: (2-Methoxy-ethyl) -carbamic acid (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester (B101336) [00323] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 4.96 (m, H), 4.54 (d, t,
    4.1 Hz, 10.8 Hz, H), 3.45 (t, 4.9 Hz, 2 H), 3.36 (s, 3 H), 3.36 (m, 2 H), 2, 04 (d, 12.8 Hz, H), 1.93 (d, q, q, 2.6 Hz, 7.0 Hz, 7.0 Hz, H), 1.66 (m, 2 H), 1.48 (m, H), 1.30 (t, 11.5 Hz, H), 1.06 (m, H), 0.95 (m, H), 0.90 (d,
    6.5 Hz, 3 H), 0.89 (d, 7.0 Hz, 3 H), 0.85 (m, H), 0.79 (d, 7.0 Hz, 3 H) ppm.
    [00324] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 156.5 (s), 74.6 (d),
    71.5 (t), 58.8 (q), 47.4 (d), 41.5 (t), 40.7 (t), 34.3 (t), 31.4 (d), 26.2 (d),
    23.6 (t), 22.1 (q), 20.8 (q), 16.5 (q) ppm.
    [00325] MS (El): m / z = 258 (<1), 257 (1), 119 (37), 95 (45), 83 (100), 76 (25), 69 (39), 55 ( 45), 41 (28), 30 (20).
    Example 1.10: (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester (6-hydroxy-hexyl) -carbamic acid (BIO1662) [00326] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 4.54 (m, 2 H), 3.64 (t,
    6.6 Hz, 2 H), 3.17 (m, 2 H), 2.04 (d, 12.3 Hz, H), 1.91 (d, q, q, 2.5 Hz,
    Petition 870170023194, of 04/07/2017, p. 107/150
    105/135
    6.9 Hz, 6.9 Hz, H), 1.66 (m, 2 H), 1.24-1.61 (m, 11 H), 1.06 (m, H), 0.93 ( m, H), 0.90 (d, 6.6 Hz, 3 H), 0.89 (d, 7.0 Hz, 3 H), 0.86 (m, H), 0.79 (d, 6.9 Hz, 3 H) ppm.
    [00327] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 156.6 (s), 74.3 (d),
    62.5 (t), 47.4 (d), 41.5 (t), 40.7 (t), 34.3 (t), 32.6 (t), 31.4 (d), 30 , 0 (t), 26.4 (t), 26.3 (d), 25.3 (t), 23.5 (t), 22.1 (q), 20.8 (q), 16, 5 (q) ppm. [00328] MS (El): m / z = 299 (<1), 138 (30), 123 (31), 95 (82), 81 (83), 71 (74), 55 (90), 41 ( 100), 31 (45).
    Example 1.11: (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester (3-methoxy-propyl) -carbamic acid (BIO1155) [00329] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 4.96 (m, H), 4.54 (d, t,
    4.1 Hz, 10.7 Hz, H), 3.45 (t, 6.0 Hz, 2 H), 3.33 (s, 3 H), 3.28 (d, t, 6.0 Hz, 6 , 0 Hz, 2 H), 2.04 (d, 11.5 Hz, H), 1.92 (d, q, q, 2.4 Hz, 7.0 Hz, 7.0 Hz, H), 1.78 (t, t, 6.3 Hz, 6.3 Hz, 2 H), 1.66 (m, 2 H), 1.48 (m, H), 1.29 (t, 11.1 Hz, H), 1.06 (m, H), 0.81-0.99 (m, 2 H), 0.90 (d, 6.5 Hz, 3 H), 0.89 (d, 7 , 0 Hz, 3 H), 0.79 (d, 7.0 Hz, 3 H) ppm.
    [00330] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 156.5 (s), 74.3 (d),
    71.1 (t), 58.7 (q), 47.4 (d), 41.5 (t), 39.0 (t), 34.4 (t), 31.4 (d), 29.7 (t),
    26.3 (d), 23.6 (t), 22.1 (q), 20.8 (q), 16.5 (q) ppm.
    [00331] MS (El): m / z = 271 (1), 138 (50), 101 (36), 95 (86), 90 (72), 83 (100), 71 (58), 55 (57 ), 41 (42), 30 (19).
    Example 1.12: (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester (3-isopropoxy-propyl) -carbamic acid (BIO1268) [00332] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 5.01 (m, H), 4.53 (d, t,
    4.1 Hz, 10.8 Hz, H), 3.55 (q, q, 6.0 Hz, 6.0 Hz, H), 3.48 (t, 5.8 Hz, 2 H), 3.28 (d, t, 6.3 Hz, 6.3 Hz, 2 H), 2.04 (d, 11.6 Hz, 1.92 (d, q, q, 2.4 Hz, 7.0 Hz, 7.0 Hz, H), 1.75 (t, t, 6.2 Hz, 6.2 Hz, 2 H), 1.66 (m, 2 H), 1.48 (m, H), 1 , 29 (m, H), 1.15 (d, 6.1 Hz, 6 H), 1.06 (m, H), 0.81-0.99 (m, 2 H), 0.90 ( d, 6.5 Hz, 3 H), 0.89 (d, 7.0 Hz, 3 H), 0.79 (d, 7.0 Hz, 3 H) ppm. [00333] 13 C-NMR ( 400 MHz, CDCI 3 , TMS): δ = 156.5 (s), 74.3 (d),
    Petition 870170023194, of 04/07/2017, p. 108/150
    106/135
    71.6 (d), 66.5 (t), 47.4 (d), 41.5 (t), 39.3 (t), 34.4 (t), 31.4 (d), 30.0 (t),
    26.4 (d), 23.7 (t), 22.1 (q), 22.1 (q), 22.1 (q), 20.8 (q), 16.6 (q) ppm. [00334] MS (El): m / z = 300 (<1), 299 (<1), 118 (93), 102 (100), 95 (42), 83 (84), 57 (64), 43 (42).
    Example 1.13: (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of hexyl-carbamic acid (BIO1271) [00335] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 4.57 (m, H), 4.54 (d, t,
    4.2 Hz, 10.8 Hz, H), 3.15 (m, 2 H), 2.04 (m, H), 1.92 (d, q, q, 2.3 Hz, 7.0 Hz, 7.0 Hz, H), 1.66 (m, 2 H), 1.41-1.55 (m, 4 H), 1.24-1.36 (m, 6 H), 1, 06 (m, H), 0.81-0.99 (m, 2 H), 0.90 (d, 6.5 Hz, 3 H), 0.89 (t, 7.0 Hz, 3 H) , 0.89 (d, 7.0 Hz, 3 H), 0.79 (d, 7.0 Hz, 3 H) ppm.
    [00336] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 156.5 (s), 74.3 (d),
    47.5 (d), 41.6 (t), 41.0 (t), 34.4 (t), 31.5 (t), 31.4 (d), 30.0 (t), 26.4 (t),
    26.3 (d), 23.6 (t), 22.6 (t), 22.1 (q), 20.8 (q), 16.5 (q), 14.0 (q) ppm. [00337] MS (El): m / z = 284 (<1), 283 (<1), 146 (86), 138 (79), 95 (70), 83 (100), 69 (35), 55 (53), 43 (41), 30 (20).
    Example 1.14: (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of isopropyl-carbamic acid (BIO1272) [00338] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 4.53 (d, t, 3.9 Hz, 10.6 Hz, H), 4.39 (m, H), 3.78 (m, H), 2.03 (d, 12.0 Hz, H), 1.90 (d, q, q, 2.5 Hz, 7.0 Hz, 7.0 Hz, H), 1.64 (m, 2 H), 1.47 (m, H ), 1.27 (m, H), 1.13 (d,
    6.6 Hz, 6 H), 1.04 (m, H), 0.80-0.98 (m, 2 H), 0.88 (d, 6.5 Hz, 3 H), 0.88 (d , 7.0 Hz, 3 H), 0.78 (d, 6.9 Hz, 3 H) ppm.
    [00339] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ 155.7 (s), 74.2 (d), 47.5 (d), 42.9 (d), 41.6 ( t), 34.4 (t), 31.4 (d), 26.3 (d), 23.6 (t), 23.1 (q), 23.1 (q), 22.1 (q ), 20.8 (q), 16.5 (q) ppm.
    [00340] MS (El): m / z = 242 (<1), 241 (<1), 226 (4), 138 (94), 104 (97), 95 (97), 83 (100), 69 (42), 55 (64), 43 (53), 29 (12).
    Example 1.15: (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of isobutyl-carbamic acid (BIO1159)
    Petition 870170023194, of 04/07/2017, p. 109/150
    107/135 [00341] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 4.64 (m, H), 4.54 (d, t,
    4.2 Hz, 10.8 Hz, H), 3.00 (m, 2 H), 2.04 (d, 11.9 Hz, H), 1.92 (d, q, q, 2.7 Hz, 7.0 Hz, 7.0 Hz, H), 1.75 (m, H), 1.66 (m, 2 H), 1.48 (m, H), 1.29 (t,
    11.6 Hz, H), 1.06 (m, H), 0.81-0.99 (m, 2 H), 0.91 (d, 6.7 Hz, 6 H), 0.90 ( d, 7.1 Hz, 3 H), 0.90 (d, 6.5 Hz, 3 H), 0.79 (d, 7.0 Hz, 3 H) ppm.
    [00342] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 156.6 (s), 74.3 (d),
    48.3 (t), 47.5 (d), 41.5 (t), 34.4 (t), 31.4 (d), 28.9 (d), 26.4 (d), 23 , 6 (t),
    22.1 (q), 20.8 (q), 19.9 (q), 19.9 (q), 16.5 (q) ppm.
    [00343] MS (El): m / z = 255 (<1), 212 (1), 138 (71), 118 (62), 95 (47), 83 (100), 69 (29), 57 ( 41), 41 (28), 30 (26).
    Example 1.16: (1S, 2R, 5S) -2-isopropyl-5-methyl-cyclohexyl methyl carbamic acid ester (BIQ1301) [00344] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 4.57 (m, H), 4.52 (d, t,
    4.4 Hz, 10.7 Hz, H), 2.76 (d, 4.9 Hz, 3 H), 2.02 (d, 11.5 Hz, H), 1.90 (d, q, q, 2.5 Hz, 7.0 Hz, 7.0 Hz, H), 1.64 (m, 2 H), 1.46 (m, H), 1.27 (t, 11.0 Hz, H) , 1.04 (m, H), 0.79-0.96 (m, 2 H), 0.88 (d, 6.5 Hz, 3 H), 0.87 (d, 7.0 Hz, 3 H), 0.77 (d, 7.0 Hz, 3 H) ppm.
    [00345] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 157.1 (s), 74.4 (d),
    47.4 (d), 41.5 (t), 34.3 (t), 31.4 (d), 27.5 (q), 26.2 (d), 23.5 (t), 22.1 (q),
    20.8 (q), 16.5 (q) ppm.
    [00346] MS (El): m / z = 214 (<1), 213 (not detected), 138 (72), 123 (38), 95 (100), 81 (81), 76 (43), 67 (29), 55 (48), 41 (33), 29 (12). Example 1.17: (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester (2-hydroxy-ethyl) -carbamic acid (B101338) [00347] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 5.01 (m, H), 4.55 (d, t, 4.0 Hz, 10.7 Hz, H), 3.73 (m, 2 H), 3, 34 (m, 2 H), 2.31 (m, 3 H), 2.05 (d, 11.9 Hz, H), 1.92 (d, q, q, 2.7 Hz, 7.0 Hz, 7.0 Hz, H), 1.67 (m, 2 H), 1.48 (m, H), 1.31 (t, 11.9 Hz, H), 1.06 (m, H ), 0.79-1.01 (m, 2 H), 0.90 (d, 6.6 Hz, 3 H), 0.89 (d, 7.0 Hz, 3 H), 0.79 ( d, 7.0 Hz, 3 H) ppm.
    [00348] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 157.4 (s), 74.9 (d),
    Petition 870170023194, of 04/07/2017, p. 110/150
    108/135
    62.3 (t), 47.3 (d), 43.4 (t), 41.4 (t), 34.3 (t), 31.4 (d), 26.2 (d), 23.5 (t),
    22.1 (q), 20.8 (q), 16.4 8q) ppm.
    [00349] MS (El): m / z = 243 (<1), 138 (57), 106 (40), 95 (65), 83 (100), 69 (40), 55 (57), 41 ( 38).
    Example 1.18: (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of benzoN, 31dioxol-5-ylmethyl-carbamic acid (BIO1571) [00350] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 6.78 (m, H), 6.76 (d,
    7.9 Hz, H), 6.73 (d, 7.9 Hz, H), 4.87 (m, H), 4.58 (d, t, 4.4 Hz, 10.8 Hz, H), 4.27 (m, 2 H); 2.06 (d, 11.9 Hz, H), 1.92 (m, H), 1.62-1.71 (m, 2 H),
    I, 49 (m, H), 1.30 (t, 12.0 Hz, H), 1.06 (m, H), 0.81-0.99 (m, 2 H), 0.90 ( d, 6.6 Hz, 3 H), 0.88 (d, 7.0 Hz, 3 H), 0.80 (d, 7.0 Hz, 3 H) ppm.
    [00351] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 156.4 (s), 147.9 (s),
    146.9 (s), 132.7 (s), 120.7 (d), 108.2 (d), 108.1 (d), 101.0 (t), 74.8 (d),
    47.4 (d), 44.9 (t), 41.5 (t), 34.3 (t), 31.4 (d), 26.3 (d), 23.5 (t), 22.1 (q),
    20.8 (q), 16.5 (q) ppm.
    [00352] MS (El): m / z = 334 (2), 333 (9), 150 (15), 135 (30), 95 (11), 83 (16), 69 (11), 55 (17 ), 41 (12).
    Example 1.19: (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of phenyl-carbamic acid (BIO158Q) [00353] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 7.39 (m, 2 H), 7.30 (m, 2 H), 7.04 (m, H), 6.55 (m, H), 4.66 (d, t, 4, 4 Hz, 10.9 Hz, H), 2.11 (d, 12.0 Hz, H), 1.97 (d, q, q, 2.7 Hz, 6.9 Hz, 6.9 Hz, H), 1.69 (m, 2 H), 1.52 (m, H), 1.37 (d, d, 10.9 Hz, 12.5 Hz, H), 1.09 (m, H ), 1.01 (d, t, 10.8 Hz,
    II, 9 Hz, H), 0.92 (d, 6.5 Hz, 3 H), 0.91 (d, 7.0 Hz, 3 H), 0.88 (m, H), 0.81 (d, 6.9 Hz, 3 H) ppm.
    [00354] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 153.3 (s), 138.2 (s), 129.0 (d), 129.0 (d), 123.2 (d), 118.4 (d), 118.4 (d), 75.1 (d), 47.4 (d), 41.4 (t), 34.3 (t), 31.4 ( d), 26.3 (d), 23.5 (t), 22.0 (q), 20.8 (q), 16.4 (q) ppm. [00355] MS (El): m / z = 276 (4), 275 (21), 137 (44), 119 (25), 93 (93), 83 (100), 69 (33), 55 (40 ), 41 (23).
    Petition 870170023194, of 04/07/2017, p. 111/150
    109/135
    Example 1.20: (1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl methyl carbamic acid ester (BIO1185) [00356] 1 H-NMR (400 MHz, CDCI 3 , TMS) : δ = 4.57 (m, H), 4.52 (d, t,
    4.4 Hz, 10.7 Hz, H), 2.76 (d, 4.9 Hz, 3 H), 2.02 (d, 11.5 Hz, H), 1.90 (d, q, q, 2.5 Hz, 7.0 Hz, 7.0 Hz, H), 1.64 (m, 2 H), 1.46 (m, H), 1.27 (t, 11.0 Hz, 11, 0 Hz, H), 1.04 (m, H), 0.91 (m, H), 0.87 (d, 6.5 Hz, 3 H), 0.87 (d, 7.0 Hz, 3 H), 0.82 (m, H), 0.77 (d, 7.0 Hz, 3 H) ppm.
    [00357] 13 C-NMR (200 MHz, CDCI 3 , TMS): δ = 157.1 (s), 74.4 (d),
    47.4 (d), 41.5 (t), 34.3 (t), 31.4 (d), 27.5 (q), 26.2 (d), 23.5 (t), 22.1 (q),
    20.8 (q), 16.5 (q), ppm.
    [00358] MS (El): m / z = 213 (not detected), 198 (0), 138 (62), 123 (34), 95 (100), 81 (79), 76 (49), 55 ( 52), 41 (50).
    Example 1.21: (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl ester of diethyl carbamic acid (BIO1553) [00359] 30 mmol of l-menthol were placed with 110 ml of dichloromethane in a 250 ml vessel at room temperature and 3.08 g (39 mmol) of pyridine were added. The reaction mixture was cooled to 0 O and 3.56 g (12 mmol) of triphosgene in 15 ml of dichloromethane were added in drops. After five minutes 2.37 g (30 mmol) pyridine was added. Subsequently, 2.19 g (30 mmol) of diethylamine in 15 ml of dichloromethane was added in drops, the resulting mixture was allowed to return to room temperature and then quenched with water. After phase separation, the water phase was extracted once with dichloromethane and the combined organic phases were concentrated. The crude product was purified by distillation and column chromatography to yield 1.5 g of the desired product as an isomeric mixture with a purity of 99.4%.
    [00360] Main signs of isomeric mixing:
    [00361] 1 H-NMR (400 MHz, CDCI 3 , TMS): δ = 4.57 (d, t, 4.4 Hz, 10.8 Hz, H), 3.26 (m, 4 H), 2.06 (d, 12.0 Hz, H), 1.94 (d, q, q, 2.8 Hz, 7.0 Hz,
    Petition 870170023194, of 04/07/2017, p. 112/150
    110/135
    7.0 Hz, Η), 1.69 (m, Η), 1.65 (m, Η), 1.49 (m, Η), 1.36 (d, d, t, 3.0 Hz,
    10.8 Hz, 12.4 Hz, H), 1.11 (t, 7.1 Hz, 6 H), 1.07 (m, H), 0.95 (d, d, 10.9 Hz, 12.1 Hz, H), 0.90 (d, 7.0 Hz, 3 H), 0.90 (d, 6.6 Hz, 3 H), 0.86 (m, H), 0.79 (d, 6.9 Hz, 3 H) ppm.
    [00362] 13 C-NMR (400 MHz, CDCI 3 , TMS): δ = 155.8 (s), 74.6 (d),
    47.5 (d), 41.6 (t), 40.9 (t), 40.9 (t), 34.4 (t), 31.4 (d), 26.3 (d), 23 , 5 (t),
    22.1 (q), 20.9 (q), 16.4 (q), 13.9 (q), 13.9 (q) ppm.
    [00363] MS (El): m / z = 255 (2), 138 (82), 118 (100), 95 (50), 83 (93), 69 (67), 55 (63), 41 (31 ), 29 (32).
    Example 2 (depigmentation effect on melanoma cell cultures) [00364] Melanoma cells from B16V mice are spread on a 96-well microtiter plate at a concentration of 5 x 103 cells / wells. After cultivation for 24 h at 37Ό and 5% CO 2 in RPMI medium, enriched with 10% fetal bovine serum, various concentrations of the test substances and 0.3 mM tyrosine and 10 nM α-MSH (a -melanocyte) are added and incubated for a further 96 h. The maximum concentration of the test substances used corresponds to 0.1 times the IC20 value of the cytotoxicity assay. Standards are incubated with kojic acid in concentrations of 0.01 mM, 0.1 mM and 1 mM in addition to tyrosine and α-MSH. Only tyrosine and α-MSH are added to the controls. After incubation, sodium lauryl sulfate and sodium hydroxide solution (final concentration: 1 mM and 1 M respectively) are added to the culture medium and the absorption (A) is measured after 3 h at 400 nm.
    [00365] Pigmentation inhibition in the presence of test compounds or kojic acid was calculated using the following equation:
    [00366] Pigmentation inhibition (%) = 100 - [(A cornpostod and te . Te / AcQntrole) X ”l 00] where
    Petition 870170023194, of 04/07/2017, p. 113/150
    111/135 [00367] Test compound A = well absorption with test substance and cells [00368] Control A = well absorption without test substance, but with cells [00369] From pigmentation inhibition (%) in a series of dilutions of test compounds, the IC 50 for each test compound is calculated. This is the concentration of a test compound in which pigmentation is inhibited by 50%.
    Table 2
    test substance IC 50 [μΜ] reference Kojic acid 452.3 reference beta-Arbutin 67.0 BIO1151 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylethyl carbamic acid ester 40.9 BIO1571 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylbenzo acid ester [1,3] dioxol-5-ylmethyl-carbamic 5.5 BIO1266 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylester of cyclohexyl carbamic acid 18.8 BIO1460 (1S, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylacid ester (3-methoxy-propyl) -carbamic 7.3 BIO1461 (1S, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylethyl carbamic acid ester 28.7 BIO1580 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylphenyl carbamic acid ester 6.9 BIO1632 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl(2-ethoxy-phenyl) -carbamic acid ester 3.2 BIO1633 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl(2-acetyl-phenyl) -carbamic acid ester 25.4
    Petition 870170023194, of 04/07/2017, p. 114/150
    112/135
    test substance IC 50 [μΜ] BIO1695 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylbenzyl carbamic acid ester 7.7 BIO1699 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylcyclohexylmethyl-carbamic acid ester 1.4 BIO1155 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylacid ester (3-methoxy-propyl) -carbamic 22.1 BIO1267 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylbutyl carbamic acid ester 498.5 BIO1268 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylacid ester (3-isopropoxy-propyl) -carbamic 19.6 BIO1271 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylhexyl carbamic acid ester 18.9 BIO1301 (1S, 2R, 5S) -2-isopropyl-5-methyl-cyclohexylmethyl carbamic acid ester 63.9 BIO1702 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylacid ester (tetrahydro-furan-2-ylmethyl) -carbamic 14.8 BIO1159 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylisobutyl carbamic acid ester 100.1 BIO1336 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl(2-methoxy-ethyl) -carbamic acid ester 35.3 BIO1339 (1S, 2R, 5S) -2-isopropyl-5-methyl-cyclohexylacid ester (3-methoxy-propyl) -carbamic 53.2 BIO1378 (1S, 2R, 5S) -2-isopropyl-5-methyl-cyclohexylethyl carbamic acid ester 29.3
    Petition 870170023194, of 04/07/2017, p. 115/150
    113/135
    test substance IC 50 [μΜ] BIO1662 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyl(6-hydroxyhexyl) -carbamic acid ester 50.7 BIO1553 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexyldiethyl carbamic acid ester 10.7 BIO1185 (1R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexylacid ester 109.2 Example 3: E Made of ex vivo leather skin
    [00370] Pigmented pigskin was excised from animals (kept for food production; the pigskin model included the subcutaneous fat layer as described in EP 1 939 27), cut into pieces of 4x4x3 mm (length x width x height) and placed in the culture at the air-liquid interface on a sterile cotton pad soaked with 5 ml of customized DMEM (Dulbecco's Modified Eagle Medium). Assays were started 24 h after the culture acclimatized to 37Ό, 5% CO 2 - O / W emulsions (as described in more detail below) without (= control) and and with the test compounds, respectively, were applied topically and incubated by 6 days. Histological sections were prepared and melanin granules stained by the Fontana-Masson technique. The granules were quantified by image analysis.
    Test substance Quantity in% inWeight Melanin score vs. Control BIO1155 1 % - 46% BIO1151 1 % - 44%
    [00371] These data show that the compounds of formula (I) according to the present invention have an amount depigmentation effect on the skin ex vivo.
    [00372] The O / W emulsions used had the following composition:
    Phase Ingredient NomelNCI % by weight
    Petition 870170023194, of 04/07/2017, p. 116/150
    114/135
    THE Water Water (Aqua) Ad 100 Hydrolyte-5 1.2 Pentylene Glycol 2.00 B Liquid PLC 100 Cetearyl Octanoate 3.00 Lanette O Cetearyl alcohol 2.00 Paraffin oil5Έ Mineral oil 3.00 Eutanol G Octyldodecanol 4.00 Abil 350 Dimethicone 0.50 Ç Pemulen TR1 Acrylates / C 10-30 Acrylic alkyl cross polymercan 0.20 Ultrez-21 Acrylates / C 10-30 Acrylic alkyl cross polymercan 0.05 D Sodium hydroxide,10% solution Sodium hydroxide 0.50 AND BIO1155 orBIO1151 1.00 Hydrolyte-5 1.2 Pentylene Glycol 3.00
    Manufacturing procedure:
    [00373] Phases A and B were heated to 70 � separately. Pemulen TR1 as well as Ultrez-21 are dispersed in Phase B when heated to 70 Ό. Phase B / C is added to phase A by mixing with an Ultra Turrax, followed by emulsification. Phase D is slowly added to phase A / B / C using a paddle mixer and the pH 5.5 - 6 is adjusted. The formulation is cooled while mixing with a mixture of p's. Phase E is prepared by dissolving one or more compounds of formula (I) in Hydrolyte 5. Subsequently, phase E is added to the mixture of phase A-D.
    Formulation examples: List A compound
    Petition 870170023194, of 04/07/2017, p. 117/150
    115/135 [00374] Unless otherwise indicated in the respective formulation example, each compound from the following list A was formulated separately in each single formulation of the K1-K11 eF1-F10 formulation examples given below.
    List A:
    BIO1151, BIO1571, BIO1266, BIO146Q, BIO1461, BIO158Q, BIO1632,
    BIO1633, BIO1695, BIO1699, BIO1155, BIO1553 and BIO1185.
    [00375] Additionally, many formulations have been produced including mixtures of two, three of four different compounds selected from list A. In such a case, the amount used in the formulation example refers to the sum of the compounds selected from the list. A used here.
    [00376] In the case two different compounds from list A were used as a mixture in the formulation examples given here, generally the weight ratio of the two compounds was chosen in the range from 10: 1 to 1: 10, preferably in the range a from 5: 1 to 1: 5, more preferably in the range from 3: 1 to 1: 3.
    [00377] In examples of formulations K1 - K9 and K11 the following two perfume oils PFO1 and PFO2 were each used as a fragrance (DPG = dipropylene glycol).
    [00378] perfume oil PFO1 with rose aroma
    Component / NAME Parts by weight Acetophenone, 10% in DPG 10.00 n-Undecanal 5.00 C14 aldehyde, so called (peach aldehyde) 15.00 Allylamyl glycolate, 10% in DPG 20.00 Amyl salicylate 25.00 Benzyl acetate 60.00 Citronelol 80.00 d-Limonene 50.00
    Petition 870170023194, of 04/07/2017, p. 118/150
    116/135
    Component / NAME Parts by weight Decenol trans-9 15.00 Dihydromyrcenol 50.00 Dimethylbenzylcarbinyl acetate 30.00 Diphenyloxide 5.00 Eucalyptus 10.00 Geraniol 40.00 Nerol 20.00 Geranium oil 15.00 Cis-3 hexenol, 10% DPG 5.00 Cis-3 hexenyl salicylate 20.00 Indole, 10% in DPG 10.00 Alpha-lonona 15.00 Beta-lonona 5.00 Lilial® (2-methyl-3- (4-tert-butyl-phenill) propanal) 60.00 Linalool 40.00 Methylphenyl acetate 10.00 Phenylethyl alcohol 275.00 Styrolyl acetate 20.00 Terpineol 30.00 Tetrahydrolinalool 50.00 Cinnamyl alcohol 10.00 Total: 1,000.00
    [00379] Perfume Oil PFO2 with white flower and almond aroma
    Component / NAME Parts by weight Benzyl acetate 60.00 Citronellet acetate 60.00 Cyclamenaldehyde (2-methyl-3- (4-isopropylphenyl) propanal 20.00
    Petition 870170023194, of 04/07/2017, p. 119/150
    117/135
    Component / NAME Parts by weight Dipropylene glycol (DPG) 60.00 Etilinalool 40.00 Floral (2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol) 30.00 Globanone® [(E / Z) -8-cyclohexadecen-1-one] 180.00 Hedione® (methyldihydrojasmonate) 140.00 Hexenyl salicylate, cis-3 10.00 Vertocitral (2,4-dimethyl-3-cyclo-hexenecarboxaldehyde) 5.00 Hydratropaaldehyde, 10% in DPG 5.00 Isodamascona (1 - (2,4,4-trimethyl-2-cyclohexen-1 -il) -2-buten-1-one, 10% DPG 5.00 Isomuscona (cyclohexadecanone) 40.00 Jacinthaflor (2-methyl-4-phenyl-1,3-dioxolane) 10.00 Cis-Jasmine, 10% DPG 20.00 Linalool 50.00 Linalyl acetate 30.00 Methyl benzoate, 10% in DPG 25.00 para-Methyl cresol, 10% DPG 10.00 Nerol 20.00 Phenillpropylaldehyde 5.00 2-Phenylethyl alcohol 82.00 Tetrahydrogeraniol 13.00 2,2-Dimethyl-3-cyclohexyl-1-propanol 80.00 Total: 1,000.00
    Formulation examples K1 - K11:
    [00380] Formulations according to the invention with compositions according to Table 1
    K1 = Skin care gel (SPF 6)
    K2 = Sun Protection Lotion SPF 24 (UVA / UVB Balance)
    Petition 870170023194, of 04/07/2017, p. 120/150
    118/135
    K3 = Anti-aging colored balm, SPF 15 K4 = Body lotion, SPF 15 K5 = Skin softening night cream O / W K6 = W / O cream
    K7 = Skin care ampoule
    K8 = Skin oil
    K9 = Bath & Shampoo
    K10 = Colored skin care stick SPF 50 K11 = Hair gel
    Petition 870170023194, of 04/07/2017, p. 121/150
    119/135
    I ω
    ο
    Q
    Ε δ
    w ο
    ιφ
    Ο
    C φ
    >
    C (0
    Ε
    Ο ο
    Έ ο
    ο (0 φ
    σ ω
    φ ιθ
    Ο φ
    = 3
    Ε φ
    σ ω
    φ ιθ
    Ο '(0 ο
    Q
    Ε ο
    Ο φ
    φ η
    φ
    % w / w 5 0.5 - K10 - 0.2 - CO 0.1 K9 0.2 00 0.5 K7 0.1 0.1 K6 0.5 K5 - 0.5 - K4 0.2 0.5 0.2 K3 0.05 0.5 LO CN K2 LO 0.5 0.1 5 0.1 - First name INCI Phenylethyl resorcinol Arbutin Niacinamide Kojic acid Magnesium ascorbyl phosphate Bisabolol Dimethicone Glycerin, water (Aqua), Saccharine laminate extract Ingredients φσw-22çΦT32σ_ç I lightening skin List A compound SymWhite 377 (Symrise) beta-Arbutin Nicotinamide Kojic acid Ascorbyl Phosphate Mg Other Inqredi- loved (-) alpha Bisabolol nat. Abil 350 Actipone® Laminaria SaccharinaGW
    Petition 870170023194, of 04/07/2017, p. 122/150
    120/135
    % ρ / ρ 5 Κ10 σ> CO 00 | Χ COX. CN LO 0.2 2 0.15 0.9 0.5 C0 0.6 0.5 0.2 CN - 0.5 0.5 5 n-_ 3.2 0.2 First name INCI Leaf juiceAloe Barbadensis Aluminum stearate Dehydroxanthum gum Betulin Arginine Troxerutin Acrylates / C 10-30 Alkyl acrylate cross polymer Carbomer Acrylate / C 10-30 alkyl acrylate cross polymer Citric acid Ingredients Aloe Vera Gel Cone, 10: 1 Aluminum stearate Amaze XT Betulin 90% (1079) Biotive® LArginine Biotive® T roxerutin Carbopol ETD 2020 Carbopol ETD 2050 Carbopol Ultrez-21 Citric acid in the sun. 10% in water
    Ο ι / *>
    ÕD
    Λ r »ο
    γν ϊ>
    ο ο
    Ό
    CN
    Ο
    Ο wrath ς>
    Έ
    121/135
    % w / w 5 0.1 - 0.5 K10 C | K9 - 2.5 0.3 00 K7 - K6 K5 C | - K4 CO K3 C | K2 C | co 5 - First name INCI Cocamide MEA DietiIhexil naphthalate 2.6 Climbazole Glyceryl stearate Pentaerythrityl distearate PEG-3 disestearate Dimethicone / dimethicone vinyl crosslinked polymer, Silica Acrylate copolymers Dipropylene Glycol PEG-12 Dimethicone Cyclohexyloxane Panthenol Ingredients Comperlan 100 Corapan TQ Crinipan® AD Cutina GMS V Cutin PES Cutina TS Cosmetic powder DC9701 Dermacryl AQF DipropyleneGlycol Dow Corning193 surfactant Dow Corning246 fluid D-Panthenol 75L
    Petition 870170023194, of 04/07/2017, p. 124/150
    122/135
    % w / w 5 K10 0.5 K9 00 K7 - K6 0.8 K5 CO - 0.8 C | K4 LO K3 K2 5 First name INCI Glyceryl stearate / citrate Glyceryl citrate oleate, caprylic-capric triglyceride Water (Aqua), Butylene Glycol, Glycerin, Avena Sativa Corn Grain Extract (Oats) Water, Glycerin, Avena Sativa (Oat corn grain extract) Phenoxyethanol, Methylparaben, Ethylparaben, Butylparaben, Propylparaben, Isobutylparaben Glycerin, Triticum Vulgare (Wheat) Gluten, Water (Aqua) Ingredients Dracorin® CE Dracorin® GOC Drago-Beta-Glucan DragoCalm® Dragocide®Liquid Dragoderm®
    Petition 870170023194, of 04/07/2017, p. 125/150
    123/135
    % w / w 5 0.1 K10 LO K900 LO K7 0.2 0.1 K6 00 0.2 1 ^ - K5 n- - K4 0.1 K3 0.1 LO 0.1 CN K2 CN 0.1 CN 5 0.2 O First name INCI Sorbitan isostearate, hydrogenated castor oil, ceresin, beeswax (Alba wax) Bisabolol Carnosine Ethylhexyl Isononanoate Tetrasodium EDTA Disodium EDTA Potassium cetyl phosphate, Hydrogenated palm glycerides Ethanol Propylene Glycol,Water (Aqua), Ginkgo Biloba leaf extract, Glucose, Lactic acid Ingredients Dragosan W / OP Dragosantol®100 Dragosine® Dragoxat® 89 EDTAB EDTA BD Emulsiphos® Ethanol Extrapone® Ginkgo Biloba
    Petition 870170023194, of 04/07/2017, p. 126/150
    124/135
    % w / w 5 0.1 0.5 O K10 CO 0.2 K9 - 0.5 - 00 0.5 O K7 0.1 0.1 K6 0.3 CO - K5 0.4 LO - K4 0.2 LO K3 C | 0.3 K2 0.2 CO C | 5 0.1 2.5 CO First name INCI color fragrance Mentone Glycerin Acetal Mentil lactate Propylene Glycol,Water (Aqua), Citric acid, Citrus Aurantium Dulcis Juice (orange), Trideceth-9, Bisabolol Glycerin Pentylene Glycol Water, Pentylene Glycol, Glycerin, Lactic acid, Sodium lactate, Serine, Urea, Sorbitol, Sodium chloride, Allantoin Ingredients E172 + E171 brown food powder FragrancePFO1 or PFO2 Frescolat®MGA Frescolat® ML Fruitapone® Orange B Glycerinae99.5% Hydrolite®-5 Hydroviton®-24
    Petition 870170023194, of 04/07/2017, p. 127/150
    125/135
    % ρ / ρ 5 CO Κ10 CO LO Κ9 0.1 00 LO ad100 Κ7 0.05 Κ6 C | 0.7 00 Κ5 0.1 CO Κ4 - 0.2 Κ3 0.2 Κ2 C | 0.4 - 0.5 0.3 5 - First name INCI Diisopropyl adipate Triisononanoin Isopropyl palmitate Hydroxypropyl Guar, Hydroxypropyltrimony chloride Simmondsia Chinensis (Jojoba) seed oil Xanthan gum Cetyl alcohol Cetearyl alcohol Galactoarabinano PVP Magnesium sulfate Minerall oil Ingredients Iso Adipat Isodragol® Isopropyl Palmitate Jaguar C-162 Jojoba Oil Keltrol CG RD Lanette 16 Lanette O Lara Care A200 Luviskol powderK30 Magnesium sulfate Mineral oil
    Ο l / *>
    οδ
    ΓΗ
    ÕD
    Λ r »ο
    ΓΗ ϊ>
    ο ο
    Ό
    ΓΗ
    Ο ο
    anger ς>
    Έ
    ASS
    126/135
    % ρ / ρ 5 Κ10 ο LO Κ9 00 Κ7 Κ6 Κ5 Κ4 CO LO O Κ3 Μ- CN 6.7 O Κ2 ο CO 6.7 - LO O 5 CO - First name INCI Octocylene Butylmethoxydibenzoyl methane Disodium phenyl dibenzimidazole tetrasulfonate Aqua, Phenyl dibenzimidazole disodium tetrasulfonate, Arginine Isoamilp.Methoxycinnamate Homosalate Aqua, Sulfonic Acid Phenylbenzimidazole, Arginine 4Methylbenzylidene camphor Ingredients Neo Heliopan® 303 Neo Heliopan® 357 Neo Heliopan® AP Neo Heliopan® AP, 15% sol., Neutralized with Biotive® LArginine Neo Heliopan®E 1000 Neo Heliopan® HMS Neo Heliopan® Hydro, 20% sol., Neurtralized with Biotive® LArginine Neo Heliopan® MBC
    Ο ι / *>
    ÕD
    Λ r »ο
    ϊ>
    ο ο
    Ό wrath ς>
    Έ tt127 / 135
    Ο.
    Ί2_ ω
    £
    C φ
    Τ3 σ>
    c σ>
    1 ^ co
    LO
    CN
    LO φ
    φ σ
    ο
    Η— '
    Φ
    O
    Φ
    W ©
    C φ
    α.
    ο φ
    I
    Φ W Ζ Ο ρ ~ · _ οο
    CO
    ο.
    (0 ο
    (Λ ο
    φ σ
    ο ο
    ιΟ.
    > Φ ο
    σ> - ~ ϋ ο I— ο φ
    Φ
    C ο
    φ
    Ό
    CN φ
    -4-J 'ΐ_ φ
    Ο
    Ν
    Ο φ
    -4-J ι_ φ
    Ο
    Ν
    Ο σ>
    οο οο
    CN
    LO
    CN (0 φ
    Η— '
    Φ
    Ο (0 ο
    C (0
    X φ
    ο ο
    - + - * “LLI“ C ο
    ο σ
    ’Φ σ
    Ο
    0.
    LO ο
    φ «ο Φ Ο φ φ φ = σ ο. Q *
    Φ ~
    -I— '
    α. Js φ φ Τ I -I- - · - »ο
    W _j
    Ο
    Ο-- Λ φ Φ Ηο «Ο ο
    φ σ
    - ο ο ο ο ο φ, £ -ο ο ‘φ
    I— 8 φ
    c ο
    ο ο
    ο Ο ο ο © φ
    -Ο ο 0- 4 =
    LO
    CN ο
    CN ο
    ο ο
    ο c Ο σ> ·> 2 Ο Φ LU 4 = 0_ ο Γ φ Ο ~ LLI Ε 0Φ ο 0. -σ φ
    C φ
    ο σ>
    φ σ
    ο
    Η— '
    Φ
    Ο ο
    φ σ
    ϊ ο Φ 00 Οί W ο
    ο φ
    φ ~ «§ £ φ φ Ό Ο -> -t—>
    φ φ _Ι C ο S
    Ο. 00
    SS
    Φ 00 Οί W
    Φ
    C ο
    ο φ
    Ε □
    C φ
    φ
    Η— '(Λ
    LJJ φ
    C ο
    ο ώ
    Φ LO J = CO Ο
    C0 'st
    Ο
    Τ3> Ο (Λ
    Φ σ
    ο
    Η— '2 ο Ο
    Sodium chloride
    Petition 870170023194, of 04/07/2017, p. 130/150
    128/135
    % w / w 5 0.5 K10 LO K900 K7 LO - LO K6 K5 0.9 - - 0.5 K4 C | 0.5 C | K3 0.5 0.5 K2 C | 5 0.6 First name INCI Sodium hydroxide Hydrogenated PEG40 castor oil, Trideceth-9, Propylene Glycol, Water (Aqua) Pentylene Glycol, Butylene Glycol, Hydroxyphenyl Propamidobenzoic Acid Decylene Glycol 1,2 Hexanediol, Caprilyl Glycol Water (Aqua) Glycerin, Beta Glucan Benzylidene Dimethoxydimethylindanone Maltodextrin, Rubus Fruticosus leaf extract (blackberry) Neopentyl Glycol Diisononanoate Ingredients Sodium hydroxide sol. The10% Solubilizer SymCalmin® SymClariol® SymDiol® 68 SymGlucan® SymHelios®1031 SymMatrix® SymMoIlient® L
    Petition 870170023194, of 04/07/2017, p. 131/150
    129/135
    Ο.
    Ί2_ ω
    C φ
    το
    Ε
    σ) c
    σ>
    οο
    1 ^ CO
    LO
    X.
    X.
    CN
    X.
    φ
    Μ- »
    Φ
    Ο φ
    το (0 ο
    c (0
    C C0 ο Έ Ζ C0
    CN
    LO
    LJJ ^ 2 < ο C (0 C ο C ο Φ φ
    ο φ
    το
    Ε ω> »-> ω>
    οο
    CN ο
    LO ο
    LO ο
    LO φ
    το _ι_ ο ο 5§
    X ϊ— ϊ— LU φ φ .ο σ) ο 'σ> 2 õ 2 0 20 Ν 8 ώ 5 8 co ο.
    <η .9-. x co Ρ ΤΟ ο Ρ Ε C _ £ Ξ C0 C0 = ±± ε
    υ υ π
    Ρ'ΐ ísS
    Φ φ Ιο. φ ν
    8-Õ = Ε ο co «J φ φ Ο το φ co φ φ ο: õ ο φ h -σ« 2 õ 5 φ · <ώ 2.
    Ύ c
    φ ο
    ο ο
    C φ
    -FJ
    C φ
    Οο ο
    ο
    -FJ ο
    C0 φ
    ΤΟ ο
    Φ φ
    ΤΟ> Ο
    0C φ
    ΤΟ
    C0 η
    ι_
    C0 φ
    ο ο C0 2 $ <Iφ φ C σ) with „Ε .φ φ ο
    ο <
    § 8 I ο X 3 2 co
    2Ζ φ - Ο Φ C0 ΤΟ
    Φ
    Φ ΤΟ ΤΟ -
    Ο JS C ._ φ Ν ±: C0 χ c 8 · “X φ c 22 ώδ (Λ φ m S co ο
    ο
    ο.
    C0
    I— φ
    ΤΟ
    Ο σ
    'Ε <
    φ φ
    οί
    Ε >>
    ω
    C0
    ο.
    φ
    0Í
    Ε >>
    W σ> ϊ = ο ώ
    Ε @ >> φ ω>
    ©
    C0
    Η>
    Ε >>
    ω ο
    φ ο
    Ç
    Pure Tapioca
    Petition 870170023194, of 04/07/2017, p. 132/150
    130/135
    % w / w 5 0.5 ad100 K10 ad100 0.7 C | K9 LO LO ad100 00 0.5 K7 ad100 K6 0.2 ad100 K5 ad100 K4 LO 0.5 ad100 K3 0.5 ad100 K2 0.5 ad100 5 ad100 First name INCI Ozokerita CocoamidopropylBetaine C12-15 Alkyl Benzoate Laureth Sodium Sulfate Triethanolamine Tocopherol Acetate C26-C28 Alkyl Dimethicone Water (Aqua) Ingredients TeCe-OzokeritN502 Tego Betain L7 Tegosoft TN Texapon N70 Triethanolamine99% Vitamin E acetat Wacker-Belsil CDM3526 VP Water, demin.
    Petition 870170023194, of 04/07/2017, p. 133/150
    131/135
    Examples: F1 - F10: Examples of orally used consumables TBeleza from inside]
    Example F1: Fruit gums
    % by weight Water Ad 100 Sucrose 34.50 Glucose Syrup, DE 40 31.89 Iso C * Tru Doce Syrup 01750 (CerestarGmbH) 1.50 Gelatin Efflorescence 240 8.20 Yellow and red food coloring 0.01 Citric acid 0.20 List A compound 0.075
    Example F2: Sewn Sweets
    I (% by weight) II (% by weight) Sugar (Sucrose) Ad 100 Ad 100 Corn syrup withhigh fructose 41.00 41.00 Maltose 3.00 3.00 Plama corn grain oil 0.90 0.90 Citric acid 0.30 0.30 Ginger extract 0.40 - Ginseng Extract - 0.40 Blue dye 0.01 0.01 List A compound 0.10 0.25 Candy - 1.50 Sweet scent - 0.30
    Example F3: Gelatin capsules suitable for direct consumption% by weight
    Petition 870170023194, of 04/07/2017, p. 134/150
    132/135
    1 II III Gelatin shell: Glycerin 2,014 2,014 2,014 Gelatin efflorescence 240 7.91 7.91 7.91 Aspartame 0.05 - - Sucralose 0.035 0.050 0.070 Allura Red (red coloring) 0.006 0.006 0.006 Brilliant Blue 0.005 0.005 0.005 Core composition: Vegetable oil triglyceride (fractionof coconut oil) up to 100 up to 100 up to 100 Aroma G 9.95 12.0 12.0 List A compound 0.07 0.20 0.50
    [00381] Aroma G had the following composition here (in% by weight): 0.1% neotam powder, 29.3% mint oil arvensis, 29.35%, 2.97% sucralose, 2.28% triacetin, 5.4% diethyl tartrate, 12.1% yakima pepper oil, 0.7% ethanol, 3.36% 2hydroxyethylmentylcarbonate, 3.0% 2-hydroxypropylmentylcarbonate, 5.77% D-limonene, 5.67% and L-menthylacetate.
    [00382] Gelatin capsules I, II, III suitable for direct consumption were produced according to WO 2004/050069 and in each case had a diameter of 5 mm and the weight ratio of the core material to the cover material is 90:10. The capsules in each case opened in the mouth in less than 10 seconds and dissolve completely within less than 50 seconds.
    Example F4: Tablets in the form of round tablets
    % by weight I II III Magnesium stearate 0.9 0.9 0.9
    Petition 870170023194, of 04/07/2017, p. 135/150
    133/135
    Citric acid 0.2 0.2 0.2 List A compound 0.05 0.20 0.50 Dextrose up to 100 up to 100 up to 100
    Example F5: Chewing gum (with and without sugar)
    % by weight I II Chewing gum base 21.0 30.0 Glycerin 0.5 1.0 Aroma of eucalyptus mint menthol P1 1.0 1.4 Glucose syrup 16.5 - Powder sugar up to 100 - List A compound 0.15 0.20 Sorbitol (in powder form) up to 100 Palatinit 9.5 Xylitol 2.0 Mannitol 3.0 Aspartame 0.1 Acesulfame K 0.1 Emulgum (emulsifier) 0.3 70% Sorbitol, in water 14.0
    [00383] Aroma P1 had the following composition (in% by weight):
    [00384] 0.05% isobutyraldehyde, 0.05% 3-octanol, 0.05% dimethylsulfite, 0.1% trans-2-hexanal, 0.1% cis-3-hexanol, 0, 1 of
    Natural 4-terpineol, 0.1% isopulegol, 0.2% natural piperiton, 0.3% linalool, 1.0% isoamyl alcohol, 1.0% isovaleraldehyde, 2.5% natural alpha-pinene , 2.5% natural beta-pinene, 8.0% eucalyptol, 7.0% l-menthylacetate, 12.0% l-mentone, 5.0% isomentone, 20.5% l- carvone, 39.45% l-menthol.
    [00385] The following table refers to Examples F6 -F10:
    Example F6 = instant drink powder
    Petition 870170023194, of 04/07/2017, p. 136/150
    134/135
    Example F7 = powder of instant drink, without sugar Example F8 = Lemonade (soft drink)
    Example F9 = Soy fruit drink Example F10 = low-fat yogurt
    % by weight F6 F7 F8 * F9 F10 List A compound 0.50 0.70 0.10 0.05 0.20 Sugar (sucrose) up to 100 Citric acid 4.00 33.33 0.2 Trisodium citrate 0.26 Tricalcium phosphate 0.22 Ascorbic acid (Vitamin C) 0.24 0.44 Opacifier and titanium dioxide (E 171) 0.20 Xanthan gum (E415) 0.072 carboxymethylcellulosesodium (E 467) 0.064 Pectin (E 440) 0.04 Pineapple aromapowdered - dry,contains tartrazine yellow dye 0.40 Raspberry aromapowdered - dry,contains red dye 11.50 Lemon-lime aroma 0.01 D-Limonena 0.005
    Petition 870170023194, of 04/07/2017, p. 137/150
    135/135
    % by weight F6 F7 F8 * F9 F10 Maltodextrin (powder) up to 100 Aspartame 3.30 sucrose 8.0 6.0 5.0 Hesperetin (1% inweight in 1.2-propylene glycol) 0.05 Ethylhydroxymethyl perforationninth 0.01PPb Vanilla flavor 0.10 0.125 Vanilla 15 ppb Maltol 350 ppb 2,5-d i meti l-4-h id roxi-2H-furan-3-one 3 ppb 1,2-Propylene glycol 0.1 Mix of fruit juice concentrates 45.0 Soy powder 5.0 Yogurt (1.5% by weight of fat) up to 100 Water up to 100 up to 100
    * Carbon dioxide is added after filling all bottles.
    Petition 870170023194, of 04/07/2017, p. 138/150
    1/8
    权利要求:
    Claims (14)
    [1]
    1. Cosmetic use of a compound or a cosmetically acceptable salt of a compound or a mixture containing two or more of these compounds or the salts thereof, where the compound is selected from the group consisting of
    Petition 870170053787, of 07/28/2017, p. 5/15
    [2]
    2. Use, according to claim 1, characterized by the fact that the compound in question has the configurations indicated in formulas (Ia), (ent-it), (Ib) and (ent-lb) in the respective indicated portions:
    O (Ia) (ent-it)
    Petition 870170053787, of 07/28/2017, p. 6/15
    2/8 characterized by the fact that it is for lightening hair and / or skin.
    [3]
    3. Cosmetic composition, preferably topical, for whitening skin and / or hair, characterized by the fact that it comprises:
    (a) one, two or more compounds as defined in claim 1 or 2 and / or an edible acceptable salt thereof, preferably in an amount having a lightening effect on the skin and / or hair, and (b) one or more ingredients additional actives for skin lightening and / or hair suitable for cosmetic application other than compounds (a), preferably in an amount having a lightening effect on skin and / or hair.
    3/8 (Ib) (ent-lb)
    [4]
    4-hydroxyanisole.
    4/8 nine, gluconic acid, chromone derivatives, preferably aloesin, flavonoids, 1-aminoethyl phosphonic acid, thiourea derivatives, ellagic acid, nicotinamide (niacinamide), zinc salts, preferably zinc chloride or zinc gluconate, tujaplicin and derivatives, triterpenes, preferably maslinic acid, sterols, preferably ergosterol, benzofuranones, preferably senquiunolide, vinyl guidecol, ethyl guidecol, dionic acids, preferably dionic octodecene acid and / or zelaic acid, nitrogen oxide synthesis inhibitors, preferably L-nitroarginine and derivatives thereof, 2,7-dinitroindazole or thiocitrulline, metal chelators (preferably alpha-hydroxy fatty acids, phytic acid, humic acid, bile acid, bile extracts, EDTA, EGTA and derivatives thereof), retinoids, soy milk and extract, serine protease inhibitors or lipoic acid or other natural or synthetic active ingredients for whitening from the skin or hair, the latter preferably in the form of a plant extract, preferably bearberry extract, rice extract, papaya extract, tumor extract, blackberry extract, bengkoang extract, nutshell extract, licorice root extract or concentrated or isolated constituents thereof, preferably glabridine or lycocalconus A, extract of artocarpus, extract of rumex and ramulus species, extracts of pine species (pinus), extracts of vitis species or stylbene derivatives isolated or concentrated therefrom, extract of saxifragaceae , extract and / or grape extract.
    4. Composition according to claim 3, characterized by the fact that a plurality of or all additional active ingredients for whitening the skin and / or hair of component (b) are selected from the group consisting of kojic acid (5 -hydroxy-2-hydroxymethyl-4-pyranone), kojic acid derivatives, preferably kojic acid dipalmitate, arbutin, ascorbic acid, ascorbic acid derivative, preferably magnesium ascorbyl phosphate, hydroquinone, hydroquinone derivatives, resorcinol derivatives resorcinol, preferably 4-alkylresorcinols and 4- (1-phenylethyl) 1,3-dihydroxybenzene (phenylethyl resorcinol), sulfur-containing molecules, preferably glutathione or cysteine, alpha-hydroxy acids (preferably citric acid, lactic acid, malic acid), salts and esters thereof, N-acetyl tyrosine and derivatives, undecenoyl phenylalaPetition 870170053787, of 07/28/2017, p. 7/15
    [5]
    5/8 ang, papaya extract, turmeric extract, nutsedge extract, licorice extract (containing glycyrrhizin), alpha-hydroxy acids, 4-alkylresorcinols,
    5. Composition according to claim 3 or 4, characterized in that a plurality or all additional active ingredients for whitening the skin and / or hair of component (b) are selected from the group consisting of kojic acid, phenylethyl resorcinol, beta- and alpha-arbutin, hydroquinone, nicotinamide, dioic acid, ascorbyl magnesium phosphate and vitamin C and its derivatives, blackberry extract, bengko extractPetition 870170053787, of 28/07/2017, pg. 8/15
    [6]
    6/8 weight, and / or
    - the total amount of additional active ingredients for whitening the skin and / or hair of component (b) is in the range from 0.01 to 30% by weight, preferably in the range from 0.01 to 20% by weight , more preferably in the range from 0.01 to 5% by weight, and / or
    - the total amount of UV filter substances (UV absorbers) is in the range from 0.01% to 40% by weight, preferably in the range from 0.1% to 30% by weight, more preferably in the range from 0.2 to 20% by weight, even more preferably in the range from 0.5% to 15% by weight, in particular in the range from 1.0 to 10.0% by weight, in each case based on the total weight of the composition.
    Composition according to any one of claims 3 to 5, characterized in that a plurality or all of the active ingredients for whitening the skin and / or hair of component (b) are selected from the group consisting of inhibitors of tyrosinase, preferably selected from the group consisting of kojic acid and resorcinol derivatives for skin and / or hair bleaching, preferably 4-alkylresorcinols and phenylethyl resorcinol, more preferably selected from the group consisting of kojic acid and / or phenylethyl resorcinol.
    [7]
    7/8
    Composition according to any one of claims 3 to 6, characterized by the fact that it additionally comprises:
    - one or more agents selected from the group of substances that absorb or reflect UV radiation, preferably for cosmetic purposes, in particular for skin and / or hair protection purposes, and / or
    - one or more agents selected from the group of anti-irritating and anti-inflammatory substances, and / or
    - one or more agents selected from the group of antioxidants.
    [8]
    A compound or a cosmetically acceptable salt of a compound or mixture containing two or more of those compounds or the salts thereof as defined in any one of claims 1, 2 and 9 or a cosmetic composition as defined in any one of claims 3 to 8.
    8. Composition according to any one of claims 3 to 7, characterized by the fact that
    - the total amount of compounds (a) is in the range from 0.001 to 30% by weight, preferably in the range from 0.01 to 20% by weight, more preferably in the range from 0.01 to 5% in
    Petition 870170053787, of 07/28/2017, p. 9/15
    [9]
    9. Compound or a cosmetically acceptable salt thereof, characterized by the fact that it is selected from the group consisting of:
    o ^ o
    Petition 870170053787, of 07/28/2017, p. 10/15
    [10]
    10. Method for cosmetic whitening of skin and / or hair, characterized by the fact that it comprises the following stage:
    - application of a cosmetically effective amount of
    Petition 870170053787, of 07/28/2017, p. 11/15
    [11]
    11. Use of a compound or a cosmetically acceptable salt of a compound or mixture containing two or more of these compounds or the salts thereof as defined in any one of claims 1, 2 and 9, characterized in that it is for the preparation of a composition to lighten skin and / or hair, in particular to treat hyperpigmentation.
    [12]
    A compound or a cosmetically acceptable salt of a compound or a mixture containing two or more of these compounds or the salts thereof as defined in any one of claims 1, 2 and 9, characterized in that it is to lighten skin and / or hair , in particular to treat hyperpigmentation.
    [13]
    13. Composition, characterized in that it comprises an amount of one or more compounds as defined in any one of claims 1, 2 and 9, preferably to lighten skin and / or hair, in particular to treat hyperpigmentation.
    [14]
    14. Non-therapeutic cosmetic method of lightening skin and / or hair, characterized by the fact that it comprises the following stage:
    - applying an amount of a compound or a cosmetically acceptable salt of a compound or a mixture containing two or more of those compounds or the salts thereof as defined in any one of claims 1, 2 and 9 or a composition as defined in any one of claims 3 to 8 and 13.
    Petition 870170053787, of 07/28/2017, p. 12/15
    类似技术:
    公开号 | 公开日 | 专利标题
    EP2593079B1|2016-11-16|Menthyl carbamate compounds as skin and/or hair lightening actives
    US9072676B2|2015-07-07|Cyclohexyl carbamate compounds as skin and/or hair lightening actives
    US9125936B2|2015-09-08|Ginger extract for the protection of stem cells
    JP6553845B2|2019-07-31|Skin / hair lightening composition
    JP6449589B2|2019-01-09|Skin and / or hair lightening mixture
    JP5763048B2|2015-08-12|Composition comprising trans-tert-butylcyclohexanol as a skin irritation reducing agent
    EP2853254B1|2017-11-08|A composition for lightening skin and/or hair
    US20110294876A1|2011-12-01|Cyclohexyl carbamate compounds as anti-ageing actives
    WO2007110415A2|2007-10-04|Use of diacetyl trimers and cosmetic or therapeutic formulations containing these compounds
    JP2018516260A|2018-06-21|Cosmetic composition comprising E / Z-2-benzylindene-5,6-dimethoxy-3,3-dimethylindan-1-one
    JP2021519774A|2021-08-12|Replacement of retinol in skin treatment
    EP2389922A1|2011-11-30|Cyclohexyl carbamate compounds as anti-ageing actives
    EP2862852B1|2018-07-04|Urea derivatives for the protection of stem cells
    JP2020502082A|2020-01-23|Cosmetic blend
    JP2022036981A|2022-03-08|Cosmetic blend
    WO2010089421A2|2010-08-12|Menthyl carbamate compounds as active anti-cellulite ingredients
    同族专利:
    公开号 | 公开日
    EP2593079B1|2016-11-16|
    KR20130109987A|2013-10-08|
    WO2010097480A2|2010-09-02|
    EP2593079A2|2013-05-22|
    KR101666372B1|2016-10-14|
    CN103025311A|2013-04-03|
    BR112012029959A2|2016-09-20|
    JP2013531629A|2013-08-08|
    JP5838499B2|2016-01-06|
    CN103025311B|2016-03-16|
    US20130129646A1|2013-05-23|
    US9060949B2|2015-06-23|
    WO2010097480A3|2011-04-14|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    DE1792331U|1957-08-23|1959-07-23|Otto Seifert|DISTANCE CLAMP FOR DAMP ROOM CABLE.|
    DE1792331C3|1962-06-23|1974-01-10|Schering Ag, 1000 Berlin Und 4619 Bergkamen|Insecticidal synergistic mixtures. Elimination from: 1300725|
    DE4226043A1|1992-08-06|1994-02-10|Haarmann & Reimer Gmbh|Agents with a physiological cooling effect and active compounds suitable for these agents|
    US5833998A|1995-11-06|1998-11-10|The Procter & Gamble Company|Topical compositions for regulating the oily/shiny appearance of skin|
    GB9525261D0|1995-12-11|1996-02-07|Bayer Ag|Carbamic acid derivatives|
    US6693130B2|1999-02-18|2004-02-17|Regents Of The University Of California|Inhibitors of epoxide hydrolases for the treatment of hypertension|
    DE19642529A1|1996-10-15|1998-04-16|Bayer Ag|Aminophenol derivatives|
    US6828460B2|1999-03-22|2004-12-07|Pfizer Inc.|Resorcinol derivatives|
    DE10030891A1|2000-06-23|2002-01-03|Haarmann & Reimer Gmbh|New 3,4-dihydroxybenzyl-substituted carbonic acid derivatives are antioxidants and radical scavengers useful e.g. for preventing skin aging or protecting cosmetic, dermatological or foodstuff compositions against oxidation|
    US6372795B1|2000-06-30|2002-04-16|Unilever Home And Personal Care Usa, A Division Of Conopco, Inc.|Cosmetic compositions containing substituted amide derivatives|
    FR2816502B1|2000-11-10|2003-04-11|Oreal|COSMETIC COMPOSITION CONSISTING OF AN AMINOPHENOL DERIVATIVE AND AN ISOFLAVONOIDE|
    TW543828U|2001-07-12|2003-07-21|Foxconn Prec Components Co Ltd|Assembly of heating-tube heat sink|
    MXPA05008243A|2003-02-03|2005-10-05|Warner Lambert Co|Improved formulation for skin-lightening agents.|
    CA2535265C|2003-08-22|2014-01-28|Dendreon Corporation|Compositions and methods for the treatment of disease associated with trp-p8 expression|
    JP5058768B2|2007-12-11|2012-10-24|新日本製鐵株式会社|Utilization of iron source recovered from steelmaking slag|
    EP2307357A1|2008-05-30|2011-04-13|Symrise AG|L-menthyl-n-carbamate|
    EP2135516B1|2008-06-13|2012-08-15|Symrise AG|Neo-menthyl derivatives as flavourings|
    CN102781476A|2009-11-18|2012-11-14|墨累古尔本合作有限公司|Methods for improving oral delivery|
    EP3348277A1|2009-11-20|2018-07-18|The Regents of The University of California|Epithelial membrane protein-2 and proliferative vitreoretinopathy |
    JP5838497B2|2010-05-25|2016-01-06|シムライズ アーゲー|Cyclohexyl carbamate compounds as anti-cellulite active ingredients|
    WO2010122178A2|2010-05-25|2010-10-28|Symrise Gmbh & Co. Kg|Cyclohexyl carbamate compounds as skin and/or hair lightening actives|WO2010122178A2|2010-05-25|2010-10-28|Symrise Gmbh & Co. Kg|Cyclohexyl carbamate compounds as skin and/or hair lightening actives|
    JP5838497B2|2010-05-25|2016-01-06|シムライズ アーゲー|Cyclohexyl carbamate compounds as anti-cellulite active ingredients|
    MY175521A|2011-01-07|2020-07-01|Allergan Inc|Melanin modification compositions and methods of use|
    JP2012158554A|2011-02-01|2012-08-23|Mikimoto Pharmaceut Co Ltd|Skin care preparation|
    WO2013010590A1|2011-07-21|2013-01-24|L'oreal|Cosmetic and/or dermatological composition containing a merocyanine derivative comprising specific polar groups consisting of hydroxyl- and ether-functionalities|
    FR3001634B1|2013-02-06|2015-02-27|Oreal|USE OF ORANGE ESSENTIAL OIL TO TREAT SKIN PIGMENTATION DISORDERS|
    EP2772245B1|2013-02-27|2018-08-22|Symrise AG|Ginger extract for the protection of stem cells|
    EP2774604B1|2013-03-08|2017-08-30|Symrise AG|Cosmetic compositions|
    EP2789369B1|2013-04-14|2018-06-06|Symrise AG|A composition for lightening skin and hair|
    CN103284926B|2013-06-08|2014-11-05|上海巴方精细化工有限公司|Cypress essential oil bath salt|
    FR3006587B1|2013-06-10|2016-05-27|Oreal|COMPOSITION FOR CORRECTING SKIN DYSCHROMY AND IMPROVING THE HOMOGENEITY OF THE DYE|
    EP2842607B1|2013-09-02|2018-05-30|Symrise AG|A skin and/or hair whitening mixture|
    CN112294853A|2013-09-22|2021-02-02|西姆莱斯股份公司|Sesuvium portulaca extract and application thereof|
    EP2853254B1|2013-09-26|2017-11-08|Symrise AG|A composition for lightening skin and/or hair|
    EP2859883B1|2013-10-13|2019-05-15|Symrise AG|Active mixtures comprising acylated oligopeptides and troxerutin|
    EP2862852B1|2013-10-18|2018-07-04|Symrise AG|Urea derivatives for the protection of stem cells|
    WO2015062629A1|2013-10-29|2015-05-07|Cutech Srl|Use of mono ornithine ketoglutarate |
    CN103585035A|2013-11-04|2014-02-19|苏州冉新生物技术有限公司|Patch-lightening essence liquid|
    CN103585033A|2013-11-04|2014-02-19|苏州冉新生物技术有限公司|Whitening patch-lightening cosmetic|
    CN103585032A|2013-11-07|2014-02-19|苏州冉新生物技术有限公司|Formula of freckle-removing cream|
    EP2979682B1|2014-07-30|2018-09-05|Symrise AG|A fragrance composition|
    EP3023090B1|2014-11-21|2019-08-07|Symrise AG|Compositions|
    EP3045161A1|2015-01-18|2016-07-20|Symrise AG|Active compositions comprising 1,2-hexanediol and 1,2-octanediol|
    WO2016161360A1|2015-04-03|2016-10-06|Nutech Ventures|Effective hair styling compositions and processes|
    EP3081207A1|2015-04-16|2016-10-19|Symrise AG|Whitening compositions|
    US10391071B2|2015-04-28|2019-08-27|Cutech Srl|Compositions comprising valerian extracts|
    EP3097905B1|2015-05-28|2020-11-04|Symrise AG|Cosmetic compositions|
    EP3108941B1|2015-06-23|2018-05-09|Symrise AG|Compositions comprising polyalkylene glycol derivatives|
    WO2017071752A1|2015-10-28|2017-05-04|Symrise Ag|Method for inhibiting or masking fishy odours|
    BR112018007384B1|2015-11-15|2021-02-17|Symrise Ag.|composition obtained by spray drying, cosmetic preparation, skin care composition and use of one or more carrier materials|
    WO2017097434A1|2015-12-06|2017-06-15|Symrise Ag|A fragrance composition|
    EP3435969A1|2016-03-30|2019-02-06|Symrise AG|An active mixture|
    KR102354954B1|2016-04-04|2022-01-24|오메자 엘엘씨|Fish Oil Topical Composition|
    CN109475490B|2016-05-23|2021-11-30|西姆莱斯股份公司|Hair care composition containing wheat bran extract|
    EP3463588A1|2016-05-30|2019-04-10|Symrise AG|Medicament comprising ginger root co2 extract|
    CA3026135A1|2016-05-30|2017-12-21|Symrise Ag|Cosmetic compositions comprising sclareolide|
    KR20190025627A|2016-06-30|2019-03-11|시므라이즈 아게|Pharmaceutical and cosmetic compositions comprising resorcinol derivatives|
    EP3500236A1|2016-08-20|2019-06-26|Symrise AG|A preservative mixture|
    EP3547991A1|2016-12-02|2019-10-09|Symrise AG|Cosmetic blends|
    IT201700090929A1|2017-08-07|2019-02-07|Cutech S R L|Cosmetic and medical uses of extracts of Coprinus comatus fungus for the regulation of pilo sebaceous unity.|
    US20210085579A1|2017-08-09|2021-03-25|Symrise Ag|1,2-alkanediols and a process for their production|
    EP3672691A1|2017-08-23|2020-07-01|Symrise AG|Uses of extracts of isochrysis sp|
    WO2019037844A1|2017-08-23|2019-02-28|Symrise Ag|Novel compositions of natural butters and uses thereof|
    BR112020006732A2|2017-10-10|2020-10-06|Symrise Ag|compositions containing benzoic acid derivatives or furoic acid and use of the derivatives for emulsion and foam stability|
    EP3813795A1|2018-03-08|2021-05-05|Symrise AG|Mixtures comprising a protein extract for the treatment of human skin and/or hair|
    US11257137B2|2018-04-03|2022-02-22|L Ford, Inc.|Customized skin care|
    KR101938877B1|2018-08-20|2019-01-16|안디바 주식회사|Soothing cream composition and method for manufacturing the same|
    BR112021004054A2|2018-09-14|2021-05-25|Symrise Ag|hair care composition|
    WO2020057761A1|2018-09-20|2020-03-26|Symrise Ag|Compositions comprising odorless 1,2-pentanediol|
    WO2020088778A1|2018-11-02|2020-05-07|Symrise Ag|A liquid and transparent blend of uv filters|
    EP3877494A1|2018-11-08|2021-09-15|Symrise AG|An antimicrobial surfactant based composition|
    KR102031885B1|2019-01-08|2019-10-15|안디바 주식회사|Soothing cream composition containing maca extract|
    EP3938054A1|2019-03-11|2022-01-19|Symrise AG|A method for improving the performance of a fragrance or a fragrance mixture|
    KR20210142707A|2019-03-22|2021-11-25|시므라이즈 아게|Plant peptides and their uses |
    WO2020192865A1|2019-03-22|2020-10-01|Symrise Ag|Plant peptides and their applications|
    CN113993500A|2019-06-13|2022-01-28|德国德之馨香精香料公司|Cool preparation|
    AU2019453263A1|2019-07-02|2022-01-06|Symrise Ag|Blend of beeswax and a lactylate ester|
    WO2021037750A1|2019-08-28|2021-03-04|Unilever Global Ip Limited|Novel compounds for skin lightening|
    WO2021043585A1|2019-09-04|2021-03-11|Symrise Ag|A perfume oil mixture|
    CN110664718A|2019-10-12|2020-01-10|合肥中科华燕生物技术有限公司|Whitening skin care product|
    WO2021073775A1|2019-10-16|2021-04-22|Symrise Ag|Articles for indirect transfer of cosmetic actives to skin|
    WO2021228352A1|2020-05-11|2021-11-18|Symrise Ag|A fragrance composition|
    WO2021260667A2|2020-06-26|2021-12-30|Universidade Do Minho|Composition for hair follicle modulation, methods and uses thereof|
    法律状态:
    2016-12-20| B15K| Others concerning applications: alteration of classification|Free format text: AS CLASSIFICACOES ANTERIORES ERAM: A61K 8/42 , A61Q 5/08 , A61Q 19/02 Ipc: A61K 8/44 (2006.01), A61K 8/92 (2006.01), C07C 271 |
    2017-01-10| B06A| Notification to applicant to reply to the report for non-patentability or inadequacy of the application according art. 36 industrial patent law|
    2017-05-02| B06A| Notification to applicant to reply to the report for non-patentability or inadequacy of the application according art. 36 industrial patent law|
    2017-09-12| B09A| Decision: intention to grant|
    2018-01-23| B16A| Patent or certificate of addition of invention granted|
    优先权:
    申请号 | 申请日 | 专利标题
    PCT/EP2010/057119|WO2010097480A2|2010-05-25|2010-05-25|Menthyl carbamate compounds as skin and/or hair lightening actives|
    [返回顶部]