USE OF ISOSORBIDE ESTER AND N-ACYL DERIVATIVES OF AMINO ACIDS AS AN ANTI-AGING AGENT FOR HUMAN SKIN

专利摘要:
On behalf of: Company of Exploitation of Products for the Chemical Industries-SEPPIC Inventors: Laetitia CATTUZZATO, Sandy DUMONT, Jerome GUILBOT Abstract Use of a compound of formula (I): in which R 'and R ", identical or different, represent either a hydrogen atom or a monovalent radical of formula (IIa): either a monovalent radical of formula (IIb): or a composition (C1) comprising from 99% to 20% by weight of a compound of formula (la), and from 1% to 80% by weight of a compound of formula (Ib), for the purpose of preventing or slowing down the appearance of signs of aging of human skin or lips or of eliminating said signs and said use being in a cosmetic composition Cosmetic process using the product of formula (I) or composition (C1), and product of formula (I) and composition (C1) as a medicament.
公开号:FR3027518A1
申请号:FR1460254
申请日:2014-10-24
公开日:2016-04-29
发明作者:Laetitia Cattuzzato；Sandy Dumont；Jerome Guilbot
申请人:Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA；
IPC主号:

专利说明:

[0001] The subject of the present invention is the use of esters of N-acyl derivatives of amino acids and of isosorbide as an anti-aging agent for the skin of the human body, as well as cosmetic, pharmaceutical and dermopharmaceutical compositions for topical use comprising said esters of N-acyl derivatives of amino acids and isosorbide intended to prevent aging of the skin of the human body. Human skin is the first image offered in the eyes of others, and therefore, the improvement of its appearance is a subject of constant concern for human beings. The skin is a reflection of a state of well-being, often associated with youth, and conversely to a state of fatigue and / or aging. Skin aging is therefore a concern for humans and more particularly for consumers of cosmetic products who are looking for solutions to mitigate and / or prevent the visible manifestations of said aging. This cutaneous aging is observed at the level of the different cutaneous tissues and is characterized by metabolic, functional, cellular, architectural and tissue alterations, leading to visible external effects characterized by the appearance and increase of wrinkles, by a dull complexion. , by a lack of uniformity of the complexion (phenomenon of dyschromism), or by a modification of the texture and the properties, in particular biomechanical, of the skin of the human body. Skin aging results from factors that are specific to each individual (characteristics of each individual's genetic heritage) and from environmental factors. Among the environmental factors that can cause skin aging include repeated and prolonged exposure to the sun, especially exposure to ultraviolet radiation, exposure to air pollution, cigarette smoke, various oxidative stress that may result among other factors previously mentioned, as well as psychological, emotional and nervous stress. The repeated and prolonged exposure of human skin to sunlight, and more particularly to ultraviolet radiation, leads to a form of aging that is commonly called photo-aging. This photo-aging is well documented in the scientific literature and it causes alterations of the skin at different levels, one of the most well-known skin alterations is solar elastosis, which is characterized by profound changes in the architecture and the organization of the elastic fibers of the dermis. These changes lead to a characteristic appearance of these skins which have very deep and marked wrinkles, inducing a tanned skin appearance, namely stiff, cracked and brown, as well as changes in their mechanical properties. Changes in the mechanical properties of human skin, related to aging, are due to the alteration of the dermal extracellular matrix, composed by elastic fibers and collagen fibers, and also to the alteration of cellular characteristics. Schulze et al (1) showed that dermal fibroblasts stiffen with age, influencing cellular functions involving the cytoskeleton, such as contractile, migratory and proliferative properties, which are important for the reorganization of the extracellular matrix. It is also known that reactive oxygen species (known as "ROS") in excess in human skin (whether the stimulus is exogenous or that the production is endogenous) create irreversible binding with the identified proteins. under the term "carbonylated proteins", which then lose their function. There has recently been a link between these carbonyl proteins and their impact on key cellular functions such as carbohydrate metabolism, protein maintenance, cell mobility, including migration, and protein homeostasis (2). (Baraibar and Friguet, 2013). Studies investigating the effect of human sera from donors of different ages on the migratory properties of fibroblasts were conducted by Kondo et al. (3). The data obtained show that the serum of elderly donors inhibits the migratory properties of fibroblasts, and even those of fetal fibroblasts. This illustrates the importance of intrinsic factors in the problematic skin aging. The so-called "photodynamic" technique has been described as particularly suitable for rejuvenation (ie the reduction of wrinkles and fine lines, pigmentation spots, etc.) of the so-called "photo-exposed" skin, namely the skin exposed to solar radiation. , and more particularly to ultraviolet radiation. The mechanism by which this technique acts has recently been studied (4), and it turns out that its mode of action includes an increase in the fibroblastic population and an increase in the migratory capacity of said fibroblasts. These recent studies thus show that the alteration of the migratory properties of fibroblasts contributes to the phenomenon of cutaneous aging. These migratory properties are important and described as part of the skin lesion repair process. Malfunctions of this process in the elderly are widely described, thus illustrating the importance of this cellular functionality. As a result, an improvement in the migratory properties of fibroblasts of the dermis of human skin and / or an increase in the fibroblastic population are means of preventing and / or treating the aging of the skin of the human body, and more particularly to prevent and / or treat the visible effects of said aging, for example wrinkles, dullness, lack of uniformity of the complexion (dyschromia), rigidity of the skin of the human body, caused by natural aging or by exposure prolonged exposure to the sun, especially exposure to ultraviolet radiation, or exposure to oxidative stress.
[0002] Physical methods for stimulating the migration of fibroblasts from human skin are known, and among these may be mentioned low intensity laser irradiation (exposure to a wavelength of 632.2 nm) more particularly intended for patients with diabetes (5). There are also many active pharmaceutical ingredients that stimulate the migration of fibroblasts, and which are mainly prescribed in the context of healing processes. It is thus possible to mention recombinant human lactoferrin produced by transgenic rice planes (6). These physical processes and these pharmaceutical active ingredients are generally used for individuals suffering from pathology, and are not adapted for cosmetic uses. There are also cosmetic active ingredients that are extracts of plants, bacteria, and which are described as acting on the migration of fibroblasts. Curcumin extracts, which stimulate healing when used in low doses and act on the migration of fibroblasts at higher doses (7); Pouteria Lucuma nut oils, characterized by the major presence of linoleic acid, oleic acid, palmitic acid, stearic acid and linolenic acid, which are described as stimulating the migration of fibroblasts and the expression of vinculin, and adapted to accelerate the healing of wounds of the skin (8); the combination of extracts of Vigna Marina, Cocos Nucifera L., Terminalia Catappa L. and Hibiscus tiliaceus L. present in cosmetic compositions to help treat wounds, improve healing, treat skin problems related to age, described in the international application published under the number VVO 2010/127396 Al. The international application published under the number VVO 2010/056908 A1 discloses the use of Pouteria lucuma extract and more particularly the oils contained in their core, for improve the migration of human fibroblasts. The use of plant extracts, bacteria, has the disadvantage of showing unreliable performance over time due to the variability of the content of the raw materials. There are also synthetic cosmetic active principles, for example peptides which are described as acting on the migration of fibroblasts. Pentapeptides of formula Lys-Thr-Thr-Lys-X may be mentioned, where X represents any natural amino acid but preferably serine and a fatty acid chain (C2 to C22) is grafted onto the N-terminal amine. and / or its esterified carboxyl group, described in the French patent application published under the number FR 2 783 169. These pentapeptides are incorporated in cosmetic or pharmaceutical compositions to cause the increase of the synthesis of collagen and glycosaminoglycans (by radioactivity ) on skin explants and the increase of the proliferation of normal human fibroblasts in culture, and consequently to improve the appearance of the skin in the case of its natural aging; of its drying up, of its cicatrization. The international application published under the number VVO 97/17835 discloses peptides containing at least one sequence of three amino acids (Lys-Lys-Gly, Gly-His-Lys or Glu-His-Lys) conjugated to a mono or dicarboxylic acid, incorporated in cosmetic or pharmaceutical compositions as a healing and anti-wrinkle agent, showing an effect on the synthesis of collagen I by fibroblasts. The N-acylated amino acid derivatives are chemical ingredients widely used for the preparation of cosmetic, dermo-cosmetic, dermopharmaceutical and pharmaceutical compositions, because of their different active properties. Mention may in particular be made of the description of lipophilic N-acyl derivatives of amino acids in the US Pat. No. 6,864,250, used in methods of treating wounds and burns. The European patent application published under the number EP 505 868 A1 describes N-acyl derivatives of amino acids and their salts, as well as their use for the treatment of osteoporosis and to promote healing. Hungarian Patent Application Publication No. HU57582 discloses N-acyl derivatives of amino acids and their salts, and more particularly N-acyl derivatives of cysteine, as well as their local use on wounds after application of lidocaine. Japanese Patent Application Publication No. JP 2002-179518 discloses N-acyl derivatives of glutamic acid and aspartic acid and their salts, characterized by acyl chains having from 6 to 24 carbon atoms, used to be incorporated in the preparation of cosmetic compositions for sensitive, dry and atopic skin. None of his documents describes the use of N-acylated amino acid derivatives to improve the migratory properties of dermal fibroblasts in human skin and / or an increase in the fibroblast population so as to prevent and / or treat the The European patent application published under the number EP 1 471 881 discloses that N-acyl derivatives of α-amino acids and in particular N-undecylenoyl phenylalanine have an affinity with respect to the Melanocyte Specific Hormone (a-MSH) and thus induce skin lightening according to the following biochemical mechanism: the competition between the α-MSH hormone and the molecule having an affinity towards the α-MSH receptor, causes a lower rate of attachment of said hormone to cellular receptors; this competition results in an inhibition of the activity of adenylate cyclase which leads to a lesser transformation of ATP into intracellular cyclic AMP; the decrease of cyclic AMP results in an inhibition of Protein Kinase A (PKA) enzyme; the inhibition of Protein Kinase A induces a lower activation of tyrosinase due to the lesser transformation of tyrosinase into phosphorylated tyrosinase; this less activation of tyrosinase leads to a decrease in melanin synthesis, which results in less pigmentation of the skin. Japanese Patent Application No. 2000-229121 discloses the use of N-acylamino acid ester polyols as high performance surfactants. The international application published under the number VVO 2010/034917 describes the mono-esters and di-esters of polyols of N- (w-undecylenoyl) phenylalanine, and more particularly the mono-esters and diesters resulting from the reaction of the glycerol and N- (w-undecylenoyl) phenylalanine, and their uses as lightening agents in human skin. The international patent application published under the number VVO 2013/001192 A1 describes monoesters and diesters resulting from the esterification reaction between isosorbide and N-acyl derivatives of amino acids, their uses as cosmetic active agent, for preventing and / or limiting the unsightly effects generated by the hypoxia of the endothelial cells of the human body, and more particularly for preventing and / or limiting the unsightly effects generated by dark circles, periocular sacs and / or heavy legs.
[0003] In the context of their research of new cosmetic active agents for the prevention and / or treatment of signs of aging of human skin or lips, the inventors have endeavored to develop a new technical solution consisting of the use of products resulting from the esterification reaction between isosorbide and N-acyl derivatives of amino acids.
[0004] This is why, according to a first aspect, the subject of the invention is the use of a compound of formula (I): OR "R'0 (I), in which R 'and R", which are identical or different, represent either a hydrogen atom; or a monovalent radical of formula (11a): ## STR3 ## in which formula R 1 -C (= O) - represents a linear or branched, saturated or unsaturated acyl radical, having from eight to thirty carbon atoms, the radical R2 represents a hydrogen atom or a radical chosen from methyl, isopropyl, isobutyl, 1-methylpropyl, hydroxymethyl, 1-hydroxyethyl, thiomethyl and 2-methylthioethyl radicals, 4-Amino butyl, 3-guanidino propyl, 3-ureido propyl, (1-amino carbonyl) methyl, carboxymethyl, 2-carboxyethyl, 2- (amino carbonyl) ethyl, benzyl, 4-hydroxybenzyl, 3,4-dihydroxy benzyl, [1H-indol-3-yl] methyl, (1H-imidazol-4-yl) methyl and 3-amino propyl, and the radical R3 represents a hydrogen atom or a methyl radical; or a monovalent radical of formula (Ib): R 4 'N 0 R 10 (11b), formula (11b) in which the group R 1 -C (= O) - is as defined in formula (11a) and R 4 represents a hydrogen atom or a hydroxyl radical, it being understood that in said formula (1), at least one of the radicals R 'or R "does not represent a hydrogen atom and that when none of the radicals R' and R" represents a hydrogen atom, R 'and R "are identical, or a mixture of compounds of formula (1), said use being for the purpose of preventing or slowing the appearance of the signs of aging of the human skin or lips or to eliminate said signs and said use being in a cosmetic composition According to a first particular aspect the invention relates to the use as defined above, of a composition (C1) comprising for 100% of its mass: from 99% by weight to 20% by weight, more particularly from 99% by weight to 50% by weight, and even more from 95% to 75% by weight of at least one compound of formula (Ia): ## STR5 ## wherein R 'represents either a monovalent radical of formula (IIa): R 1 0 (11a), formula (11a) in which the group R 1 -C (= O) - represents an acyl radical, saturated or unsaturated, linear or branched, comprising from eight to thirty carbon atoms, the radical R2 represents a hydrogen atom or a radical chosen from methyl, isopropyl, isobutyl, 1-methylpropyl, hydroxymethyl, 1-hydroxyethyl, thiomethyl, 2-methylthioethyl, 4-aminobutyl, 3-guanidinopropyl, 3-ureido radicals; propyl, (1-amino carbonyl) methyl, carboxymethyl, 2-carboxyethyl, 2- (amino carbonyl) ethyl, benzyl, 4-hydroxybenzyl, 3,4-dihydroxybenzyl, [1H-indol-3-yl] methyl, (1H-imidazol-4-yl) methyl and 3-amino propyl, and the radical R3 represents a hydrogen atom or a methyl radical; is a monovalent radical of formula (11b): ## STR5 ## in which formula R1-C (= O) - is as defined in formula (11a) and R4 represents a hydrogen atom or a hydroxyl radical, and - from 1 wt% to 80 wt%, more particularly from 1 wt% to 50 wt%, and even more particularly from 5 wt% to 25 wt% of at least one wherein R is either a monovalent radical of formula (11a): ## STR2 ## R1-C group (= O) - represents a linear or branched, saturated or unsaturated acyl radical containing from eight to thirty carbon atoms, the radical R2 represents a hydrogen atom or a radical chosen from methyl and isopropyl radicals; isobutyl, 1-methylpropyl, hydroxymethyl, 1-hydroxyethyl, thiomethyl, 2-methylthioethyl, 4-aminobutyl, 3-guanidinopropyl, 3-ureidopropyl, (1-amino carbon yl) methyl, carboxymethyl, 2-carboxyethyl, 2- (amino carbonyl) ethyl, benzyl, 4-hydroxybenzyl, 3,4-dihydroxybenzyl, [1H-indol-3-yl] methyl, (1H-imidazol-4 -y1) methyl and 3-amino propyl, and the radical R3 represents a hydrogen atom or a methyl radical; or a monovalent radical of formula (11b): R4 'NO 0 (11b), formula (11b) in which the group R1-C (= O) - is as defined in formula (11a) and R4 represents an atom of hydrogen or a hydroxy radical. By "signs of aging of the human skin or lips" is meant within the meaning of the invention, any changes in the external appearance of the skin or the lips due to aging, whether this aging is chronobiological and / or photo- induced and / or resulting from exposure to environmental stresses (air pollution, contact with dangerous substances), for example wrinkles and fine lines, alteration of the microrelief, lack of elasticity and / or tone of the skin, the lack of density and / or firmness of the human skin or lips, but also any internal changes in the skin that do not systematically result in a modified external appearance, for example any internal damage to the skin resulting from exposure to the skin. ultraviolet radiation. According to one particular aspect, the subject of the invention is the use of a compound of formula (1) or of a composition (C1) as defined above, for preventing and / or treating wrinkles, fine lines or an alteration microrelief of human skin or lips. for which said signs of aging of human skin or lips are either wrinkles, fine lines or an alteration of the microrelief of human skin or lips, or the lack of elasticity and / or tone of human skin or lips, the lack of density and / or firmness of human skin or lips.
[0005] According to one particular aspect of the present invention, the subject of the present invention is the use as described above of a compound of formula (1) or of a composition (C1) as defined above for which the compound of formula (1), the compound of formula (Ia) and the compound of formula (Ib) are chosen from among the isosorbide esters of the N-acyl derivatives of the following amino acids: glycine, alanine, serine, aspartic acid, glutamic acid, valine, threonine, arginine, lysine, proline, leucine, phenylalanine, isoleucine, histidine, tyrosine, tryptophan, asparagine, glutamine, cysteine, methionine, hydroxyproline, hydroxylysine, sarcosine or omithine. According to one particular aspect of the present invention, the subject of the present invention is the use as described above of a compound of formula (1) or of a composition (C1) as defined above for which the compound of formula (1), the compound of formula (Ia) and the compound of formula (Ib), in which the radical R1-C (= O) - represents an acyl radical, saturated or unsaturated, linear or branched, having from 8 to 22 carbon atoms. According to this particular aspect, in the definition of the radical of formula (11a) or of the radical of formula (11b), the radical R1-C (= O) - represents a radical chosen from octanoyl, decanoyl, w-undecylenoyl, dodecanoyl radicals. tetradecanoyl, hexadecanoyl, octadecanoyl, cocoyl, eicosanoyl, docosanoyl, 9-octadecenoyl, eicosenoyl, 13-docosenoyl, 9,12-octadecadienoyl or 9,12,15-octadecatrienenoyl. According to another particular aspect of the present invention, the subject of the present invention is the use as described above for which the radicals R 'and R ", which are identical or different, represent in the formula (1), an atom of hydrogen, ie a monovalent radical of formula (11a), in which R 1 -C (= O) - and R 3 are as defined above and R 2 represents a radical chosen from methyl, isopropyl, isobutyl or 1-methylpropyl radicals and more particularly, in which in the formula (11a), the group R 1 -C (= O) - is selected from octanoyl, decanoyl, w-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl or 9.12 - octadecadienoyl, R3 represents a hydrogen atom, and R2 represents a radical chosen from methyl, isopropyl, isobutyl or 1-methylpropyl radicals.According to this particular aspect of the present invention, the object of the invention is the use thereof. that dec rite previously of a compound of formula (I) or a composition (C1) as defined above for which the compound of formula (I), the compound of formula (Ia) and the compound of formula (Ib) are chosen from the isosorbide esters of the N-acyl derivatives of the following amino acids: alanine, valine, leucine and isoleucine. According to this particular aspect of the present invention, it relates to the use as described above of a compound of formula (I) or a composition (C1) as defined above for which the compound of formula (I), the compound of formula (Ia) and the compound of formula (Ib) are chosen from isosorbide esters of N-octanoyl alanine, N-octanoyl valine, N-octanoyl leucine of N-octanoyl isoleucine, N- (wundecylenoyl) alanine, N- (--undecylenoyl) valine, N- (w-undecylenoyl) leucine N- (--undecylenoyl) isoleucine, N-dodecanoyl alanine, N-dodecanoyl valine , Ndodecanoyl leucine N-dodecanoyl isoleucine, N-tetradecanoyl alanine, N-tetradecanoyl valine, N-tetradecanoyl leucine N-tetradecanoyl isoleucine, N-hexadecanoyl alanine, N-hexadecanoyl valine, N-hexadecanoyl leucine N-hexadecanoyl isoleucine, N-octadecanoyl alanine, N-octadecanoyl valine, N-octadecanoyl ucine of N-octadecanoyl isoleucine, N-oleoyl alanine, N-oleoyl valine, N-oleoyl leucine or N-oleoyl isoleucine or for which the mixture of compounds of formula (I) is selected from isosorbide esters N-cocoyl alanine, N-cocoyl valine, N-cocoyl leucine or N-cocoyl isoleucine. By N-cocoyl alanine, N-cocoyl valine, N-cocoyl leucine or N-cocoyl isoleucine, are meant mixtures of N-acylated derivatives respectively of valine, leucine or isoleucine obtained by reaction of each of these α-amino acids with the mixture of fatty acid chloride derived from coconut oil comprising per 100 mol%, about 11 mol% of octanoyl chloride, about 9.5 mol% of decanoyl chloride about 51 mole percent lauroyl chloride, about 15.5 mole percent myristoyl chloride, about 6.5 mole percent palmitoyl chloride, about 2 mole percent stearoyl chloride, about 3 mol% of oleolyl chloride, and about 1.5 mol% of linoleoyl chloride. According to another more particular aspect of the present invention, the subject of the present invention is the use as previously described of a compound of formula (Ia), as previously defi ned, chosen from isosorbide N-octanoyl alaninate, isosorbide N-hexadecanoyl valinate, isosorbide N-octanoyl isoleucinate, or the mixture of isosorbide N-cocoyl isoleucinate. According to another particular aspect of the present invention, the subject of the present invention is the use as described above of a compound of formula (Ib) as defined above, chosen from bis (N-octanoyl alaninate) of isosorbide. isosorbide bis (N-hexadecanoyl) valinate, isosorbide bis (N-octanoyl isoleucinate), or the mixture of bis (Ncocoyl isoleucinate) isosorbide. The compound of formula (1) as defined above may be prepared according to a preparation process comprising: - a step a) of esterification of a compound of formula (IIIa): ## STR2 ## wherein R1-C (= O) - and R2 are as defined in formula (11a), or of a compound of formula (IIIb): R4O OH R1 O (111b), wherein R1-C (= 0) - and R4 are as defined for the formula (I lb), with the isosorbide of formula (IV): OH HO (IV), to obtain either the compound of formula (Ia) or the compound of formula (Ib) or a mixture (M) of the compound of formula (Ia) and the compound of formula (Ib); and if necessary or if desired, - a step b) of separating the compounds of formula (Ia) and formula (Ib), from said mixture (M) obtained in step (a).
[0006] The compounds of formulas (IIIa) and (IIIb) are known or are synthesizable by N-acylation of the corresponding α-amino acids according to methods known to those skilled in the art. In the process as defined above, the molar ratio of compound of formula (IIIa) or of formula (IIIb) on isosorbide of formula (IV) is generally between 3/1 and 1/5, more particularly between 1/1 and 1/5, and even more particularly between 1/1 and 1/3. In the process as defined above, the step b) of separating the compounds of formula (Ia) and of formula (Ib) is carried out by the conventional separation methods known to those skilled in the art.
[0007] The compound of formula (1) as defined above may also be prepared according to a preparation process comprising: an esterification step a1), or of a compound of formula (IIIa): ## STR3 ## wherein R1 and R2 are as defined in formula (11a), or a compound of formula (IIIb): wherein R1 and R4 are as defined for formula (11b) with an alcohol of formula (V): R 5 -OH (V), in which R 5 represents a linear aliphatic radical having from 1 to 4 carbon atoms, to form either a compound of formula (VIa): ## STR2 ## Via), wherein R1, R2 and R5 are as defined above, ie a compound of formula (VIb): R4 (VIb), wherein R1, R4 and R5 are as previously defined; A step a2) of trans-esterification of the compound of formula (Via) or of the compound of formula (VIb) obtained in step a1), by reaction with the isosorbide of formula (IV), to obtain either the compound of formula (Ia), either the compound of formula (Ib), or a mixture (M) of the compound of formula (Ia) and the compound of formula (Ib); and if necessary or if desired, - The implementation of step b). In the process as described above, step a1) is generally carried out at a temperature of about 60 ° C to 120 ° C, under an inert gas, and in the presence of an acidic catalyst system. By acidic catalytic system are meant strong acids such as sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, hypophosphorous acid, methanesulfonic acid, para-toluene sulfonic acid, trifluoromethanesulfonic acid, or acidic ion exchange resins. In step a1) of the process as described above, the molar ratio of compound of formula (IIIa) or compound of formula (IIIb) on alcohol of formula (V) is generally between 1/1 and 1/10, more particularly between 1/1 and 1/8, and even more particularly between 1/2 and 1/8. In the process as described above, step a2) of trans-esterification of the ester of formula (Via) or of formula (VIb) obtained in step a1) is generally carried out at a temperature of about between 80 ° C and 180 ° C, more particularly between 100 ° C and 150 ° C, even more particularly between 120 ° C and 150 ° C under an inert gas, and in the presence of an acid catalyst system such as previously described, and with vacuum distillation of the alcohol of formula (V) formed in-situ. In step a2) of the process as described above, the molar ratio of compound of formula (V) to isosorbide of formula (V) is between 3/1 and 1/5, more particularly between 1/1 and 1 / 5, and even more particularly between 1/1 and 1/3. The composition (C1) as defined above can be prepared by various routes. A first route of preparation of the composition (C1), used in the object of the invention, consists in mixing, in the desired mass proportions, the compound of formula (Ia) as defined above, with the compound of formula (Ib) as defined above. A second route of preparation of the composition (Cl), implemented in the object of the invention, consists in carrying out the process for preparing the compound of formula (1) as described above, by reacting in the desired proportions, the isosorbide of formula (IV) with the compound of formula (IIIa) and / or this compound of formula (IIIb). A third route of preparation of the composition (Cl), used in the object of the invention, consists in implementing the variant of the process for preparing the compound of formula (I) as described above, by react in the desired proportions, the compound of formula (IIIa) or the compound (IIIb) with the alcohol of formula (V), then the isosorbide of formula (IV). The invention also relates to a method for the purpose of preventing or slowing the appearance of signs of aging of human skin or lips or eliminating said signs, comprising at least one step of application on the human skin or on the lips, a cosmetic formulation for topical use comprising at least one cosmetically acceptable excipient and an effective amount of at least one compound of formula (I) or a composition (Cl) as defined above. In the cosmetic process as described above, the cosmetic formulation for topical use is spread on the surface of the skin to be treated, then the skin is massaged a few moments. The expression "for topical use" used in the definition of the cosmetic formulation used in the cosmetic process that is the subject of the present invention means that said formulation is implemented by application to the skin, whether it be a direct application in the case of a cosmetic formulation or an indirect application when the cosmetic formulation according to the invention is impregnated on a support intended to be put in contact with the skin (paper, wipe, textile, transdermal device, etc ...). The expression "cosmetically acceptable" used in the definition of the cosmetic formulation for topical use, used in the cosmetic process that is the subject of the present invention, means according to the directive of the Council of the European Economic Community No. 76/768 / EEC of 27 July 1976 as amended by Directive 93/35 / EEC of 14 June 1993, that the said formulation includes any substance or preparation intended to be placed in contact with the various parts of the human body (epidermis, hair and hair system, nails , lips and genitals) or with the teeth and oral mucosa in view, exclusively and mainly, to clean, perfume, modify the appearance and / or correct body odor and / or protect them or keep them in good condition. By effective amount of the compound of formula (I) or of the composition (Cl) as defined above present in the cosmetic formulation for topical use implemented in the process as defined above, is meant for 100% of the mass. of said cosmetic formulation for topical use, the amount of between 0.1% and 5% by weight, more particularly between 0.1% and 3% by weight, and even more particularly between 0.5% and 2% by weight of compound of formula (I) or the composition (Cl).
[0008] Cosmetic formulations for topical use used in the cosmetic process as defined above, are generally in the form of aqueous or hydro-alcoholic or hydro-glycolic solutions, in the form of a suspension, an emulsion, microemulsion or nanoemulsion, whether of the water-in-oil, oil-in-water, water-in-oil-in-water or oil-in-water-in-oil type, or in the form of a powder. The topical cosmetic formulations used in the cosmetic process which is the subject of the present invention may be packaged in a bottle, in a device of the pump "bottle" type, in pressurized form in an aerosol device, in a device provided with a perforated wall such as a grid or in a device provided with a ball applicator (called "roll-on"). In general, the compound of formula (I) or the composition (Cl), present in topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, is associated with chemical additives usually used. in the field of formulations for topical use, such as foaming and / or detergent surfactants, thickening and / or gelling surfactants, thickening and / or gelling agents, stabilizing agents, film-forming compounds, solvents and co-solvents, hydrotropic agents, thermal or mineral waters, plasticizers, emulsifiers and co-emulsifiers, opacifying agents, pearlescent agents, superfatting agents, sequestering agents, chelating agents, oils, waxes, antioxidants, fragrances, essential oils, preservatives, conditioners, deodorants, bleaching agents for the fading of hair and skin, the active ingredients intended to provide a treating and / or protective action with respect to the skin or the hair, sunscreens, mineral fillers or pigments, the particles providing an effect visual or for the encapsulation of active, exfoliating particles, texture agents, optical brighteners, repellents for insects. As examples of foaming and / or detergent surfactants which can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is possible to mention may be made of foaming surfactants and / or anionic, cationic, amphoteric or nonionic detergents. Among the foaming and / or detergent anionic surfactants that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, it is mention may be made of alkali metal, alkaline earth metal, ammonium, amine, or aminoalcohol, alkyl ether sulphate, alkyl sulphate, alkylamidoether sulphate, alkylaryl polyether sulphate, monoglyceride sulphate or alpha salts. olefinsulfonates, paraffin sulfonates, alkylphosphates, alkyletherphosphates, alkylsulfonates, alkylamidesulfonates, alkylarylsulfonates, alkylcarboxylates, alkylsulfosuccinates, alkylethersulfosuccinates, alkylamidesulfosuccinates, alkylsulfoacetates, alkylsarcosinates, acylisethionates, N-acyltaurates, acyllactylates, N-acyl derivatives of amino acids, N-acyl derivatives of peptides, N-acyl derivatives of proteins or riveted N-acyl fatty acids.
[0009] Among the foaming and / or detergent amphoteric surfactants which can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is possible to mention may be made of alkylbetaines, alkylamidobetaines, sultaines, alkylamidoalkylsulfobetaines, imidazoline derivatives, phosphobetaines, amphopolyacetates and amphopropionates. Among the foaming and / or detergent cationic surfactants that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, it is mention may be made especially of quaternary ammonium derivatives.
[0010] Among the foaming and / or detergent nonionic surfactants that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process, object of the present invention mention may be made more particularly of alkylpolyglycosides comprising a linear or branched, saturated or unsaturated aliphatic radical containing from 8 to 16 carbon atoms, such as octyl polyglucoside, decyl polyglucoside, undecylenyl polyglucoside or dodecyl polyglucoside, tetradecyl polyglucoside, hexadecyl polyglucoside, 1,12-dodecanediyl polyglucoside; ethoxylated hydrogenated castor oil derivatives such as the product marketed under the INCI name "Peg-40 hydrogenated castor oil"; polysorbates such as Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 70, Polysorbate 80, Polysorbate 85; coconut amides; N-alkylamines. As examples of thickening and / or gelling surfactants that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, mention may be made of poly (alkoxylated) alkyl polyglycoside fatty esters, such as ethoxylated methylpolyglucoside esters such as PEG 120 methyl glucose trioleate and PEG 120 methyl glucose dioleate respectively marketed under the names GLUCAMATE ™ LT and GLUMATE ™ DOE 120; alkoxylated fatty esters such as PEG 150 pentaerythrityl tetrastearate sold under the name CROTHIX ™ DS53, PEG 55 propylene glycol oleate sold under the name ANTIL ™ 141; fatty chain polyalkylene glycol carbamates such as PPG-14 laureth isophoryl dicarbamate sold under the name ELFACOSTM T211, PPG-14 palmeth-60 hexyl dicarbamate sold under the name ELFACOSTM GT2125. As examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of linear or branched or cross-linked polyelectrolytic polymers, such as the homopolymer of partially or totally salified acrylic acid, the homopolymer of partially or totally salified methacrylic acid, the homopolymer of the acid 2-methyl-[(1-oxo-2-propenyl) amino] -1-propanesulfonic acid (AMPS) partially or totally salified, copolymers of acrylic acid and AMPS, copolymers of acrylamide and AMPS, copolymers of vinylpyrrolidone and AMPS, copolymers of AMPS and (2-hydroxyethyl) acrylate, copolymers of AMPS and (2-hydroxyethyl) methacrylate, copolymers AMPS and hydroxyethylacrylamide, copolymers of AMPS and N, N-dimethyl acrylamide, copolymers of AMPS and tris (hydroxy-methyl) acrylamido methane (THAM), copolymers of acrylic or methacrylic acid and acrylate of (2-hydroxyethyl), copolymers of acrylic or methacrylic acid and (2-hydroxyethyl) methacrylate, copolymers of acrylic or methacrylic acid and hydroxyethylacrylamide, copolymers of acrylic acid or methacrylic acid and THAM, copolymers of acrylic or methacrylic acid and N, N-dimethyl acrylamide, terpolymers of acrylic or methacrylic acid, AMPS and (2-hydroxyethyl) acrylate, terpolymers acrylic or methacrylic acid, AMPS and (2-hydroxyethyl) methacrylate, terpolymers of acrylic or methacrylic acid, AMPS and THAM, terpolymers of acrylic or methacrylic acid , AMPS and N, N-dimethyl acrylamide, terpolymers acrylic acid or methacrylic acid, AMPS and acrylamide, copolymers of acrylic acid or methacrylic acid and alkyl acrylates whose carbon chain comprises between four and thirty carbon atoms and more particularly between ten and thirty carbon atoms, the copolymers of AMPS and alkyl acrylates whose carbon chain comprises between four and thirty carbon atoms and more particularly between ten and thirty carbon atoms, the linear terpolymers , connected or crosslinked with at least one monomer having a strong, free, partially salified or totally salified acidic function, with at least one neutral monomer, and at least one monomer of formula (VIII): CH 2 = C (R 6) -C (= O) - [CH 2 -CH 2 -O L -R 7 (VIII) in which R 6 represents a hydrogen atom or a methyl radical, R 7 represents a linear or branched alkyl radical containing from eight to thirty carbon atoms and n represents a number higher or higher gal to one and less than or equal to fifty. Polyelectrolytes polymers, linear or branched or crosslinked that can be combined with the compound of formula (I) or composition (Cl) in cosmetic formulations for topical use implemented in the cosmetic process object of the present invention may be in the form of a solution, an aqueous suspension, a water-in-oil emulsion, an oil-in-water emulsion, a powder. Polyelectrolytes polymers, linear or branched or crosslinked that can be combined with the compound of formula (I) or composition (Cl) in cosmetic formulations for topical use implemented in the cosmetic process object of the present invention can be selected from the products marketed under the names SIMULGELTM EG, SIMULGELTMEPG, SEPIGELTM 305, SIMULGELTm 600, SIMULGELTm NS, SIMULGELTm INS 100, SIMULGELTm FL, SIMULGELTm A, SIMULGELTm SMS 88, SEPINOVTmEMT 10, SEPIPLUSTm400, SEPIPLUSTm265, SEPIPLUSTmS, SEPIMAXTmZen , ARISTOFLEXTMAVC, ARISTOFLEXTMAVS, NOVEMERTMEC-1, NOVEMERTMEC 2, ARISTOFLEXTMHMB, COSMEDIATMSP, FLOCARETMET 25, FLOCARETMET 75, FLOCARETMET 26, FLOCARETMET 30, FLOCARETMET 58, FLOCARETMPSD 30, VISCOLAMTMAT 64, VISCOLAMTMAT 100.
[0011] Examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process, object of the present invention mention may be made of polysaccharides consisting solely of monosaccharides, such as glucans or glucose homopolymers, glucomannoglucans, xyloglycans, galactomannans whose degree of substitution (DS) of D-galactose units on the main D-mannose chain is between 0 and 1, and more particularly between 1 and 0.25, such as galactomannans derived from cassia gum (DS = 1/5), locust bean gum (DS = 1/4), gum tara (DS = 1/3), guar gum (DS = 1/2), fenugreek gum (DS = 1). As examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of polysaccharides consisting of monosaccharides, such as sulphated galactans and more particularly carrageenans and agar, uronans and more particularly alginines, alginates and pectins, heteropolymers of monosaccharides and uronic acids. and more particularly xanthan gum, gellan gum, exudates of arabic gum and karaya gum, glucosaminoglycans. As examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of cellulose, cellulose derivatives such as methylcellulose, ethylcellulose, hydroxypropylcellulose, silicates, starch, hydrophilic derivatives of starch, and polyurethanes.
[0012] As examples of stabilizing agents that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of the microcrystalline waxes, and more particularly ozokerite, mineral salts such as sodium chloride or magnesium chloride, silicone polymers such as polysiloxane polyalkyl polyether copolymers. As examples of solvents that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of water organic solvents such as glycerol, diglycerol, glycerol oligomers, ethylene glycol, propylene glycol, butylene glycol, 1,3-propanediol, 1,2-propanediol, hexylene glycol, diethylene glycol, xylitol, erythritol, sorbitol, water-soluble alcohols such as ethanol, isopropanol or butanol, water mixtures and said organic solvents. As examples of thermal or mineral waters that can be associated with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, it is possible to cite thermal or mineral waters with a mineralization of at least 300 mg / I, in particular Avene water, Vittel water, Vichy basin water, Uriage water, water La Roche Posay, the water of the Bourboule, the water of Enghien-les-bains, the water of Saint-Gervais-les bains, the water of Néris-les-bains, the water of Allevard -the-baths, the water of Digne, the water of the Maizieres, the water of Neyrac-les-bains, the water of Lons le Saunier, the water of Rochefort, the water of Saint Christau, the water of the Fumades and the water of Tercis-les-bains. As examples of hydrotropic agents which can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, mention may be made of the xylene sulphonates, cumene sulphonates, hexyl polyglucoside, (2-ethyl hexyl) polyglucoside, n-heptyl polyglucoside. As examples of emulsifying surfactants which can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, mention may be made of nonionic surfactants, anionic surfactants, cationic surfactants. As examples of emulsifying nonionic surfactants that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is possible to mention esters of fatty acids and sorbitol, such as the products marketed under the names MONTANET ™ 40, MONTANET ™ 60, MONTANET ™ 70, MONTANET ™ 80 and MONTANET ™ 85; compositions comprising glycerol stearate and ethoxylated stearic acid between 5 moles and 150 moles of ethylene oxide, such as the composition comprising stearic acid ethoxylated with 135 moles of ethylene oxide and glycerol stearate. sold under the name SIMULSOL ™ 165; mannitan esters; ethoxylated mannitan esters; sucrose esters; methylglucoside esters; alkylpolyglycosides having a linear or branched, saturated or unsaturated aliphatic radical containing from 14 to 36 carbon atoms, such as tetradecyl polyglucoside, hexadecyl polyglucoside, octadecyl polyglucoside, hexadecyl polyxyloside, octadecylpolyxyloside, eicosyl polyglucoside, dodecosyl polyglucoside, 2-octyldodecyl polyxyloside, 12-hydroxystearyl polyglucoside; linear or branched fatty alcohol compositions, saturated or unsaturated, and containing from 14 to 36 carbon atoms, and alkyl polyglycosides as described above.
[0013] As examples of anionic surfactants that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process, object of the present invention, mention may be made of glyceryl stearate citrate, cetearyl sulphate, soaps such as sodium stearate or triethanolammonium stearate, N-acyl derivatives of salified amino acids for example stearoyl glutamate. Examples of emulsifying cationic surfactants that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention include aminoxides, quaternium-82 and the surfactants described in WO96 / 00719 and mainly those whose fatty chain comprises at least 16 carbon atoms. Examples of opacifying agents and / or pearlescent agents that can be combined with the compound of formula (I) or with the composition (Cl) in topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of sodium palmitate, sodium stearate, sodium hydroxystearate, magnesium palmitate, magnesium stearate, magnesium hydroxystearate, ethylene glycol monostearate, ethylene glycol distearate, polyethylene glycol monostearate, polyethylene glycol distearate, fatty alcohols having from 12 to 22 carbon atoms. As examples of texture agents that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of N-acylated derivatives of amino acids, such as lauroyl lysine marketed under the name AMI NOHOPETmLL, octenyl starch succinate marketed under the name DRYFLOTM, myristyl polyglucoside sold under the name MONTANOV ™ 14, cellulose fibers, cotton fibers, chitosan fibers, talc, sericite, mica. As examples of deodorant agents that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of the alkali silicates, zinc salts such as zinc sulphate, zinc gluconate, zinc chloride, zinc lactate; quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; glycerol derivatives such as glycerol caprate, glycerol caprylate, polyglycerol caprate; 1,2 decanediol; 1,3 propanediol; salicylic acid; sodium bicarbonate; cyclodextrins; metallic zeolites; TRICLOSANTm; aluminum bromohydrate, aluminum chlorohydrates, aluminum chloride, aluminum sulphate, aluminum and zirconium hydrochlorides, aluminum and zirconium trihydrochloride, aluminum zirconium tetrachlorohydrate , aluminum and zirconium pentachlorohydrate, aluminum and zirconium octochlorhydrate, aluminum sulphate, sodium and aluminum lactate, aluminum and glycol hydrochloride complexes, as well as propylene glycol aluminum dihydrochloride complex, aluminum and propylene glycol sesquichlorohydrate complex, polyethylene glycol aluminum aluminum and polyethylene glycol, the complex of aluminum sesquichlorohydrate and polyethylene glycol. As examples of oils which can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, mention may be made of oils minerals such as paraffin oil, liquid petrolatum, isoparaffins or mineral white oils; oils of animal origin, such as squalene or squalane, vegetable oils, such as phytosqualane, sweet almond oil, coconut oil, castor oil, jojoba oil, olive oil, rapeseed oil, peanut oil, sunflower oil, wheat germ oil, corn germ oil, soybean oil, cottonseed oil, alfalfa oil, poppy oil, pumpkin oil, evening primrose oil, millet oil, barley oil, rye oil, Safflower oil, bancoulier oil, passionflower oil, hazelnut oil, palm oil, shea butter, apricot kernel oil, calophyllum oil, sysymbrium oil, avocado oil, calendula oil, oils derived from flowers or vegetables ethoxylated vegetable oils; synthetic oils such as fatty acid esters such as butyl myristate, propyl myristate, isopropyl myristate, cetyl myristate, isopropyl palmitate, octyl palmitate, butyl stearate, hexadecyl stearate, isopropyl stearate, octyl stearate, isocetyl stearate, dodecyl oleate, hexyl laurate, propylene glycol dicaprylate, lanolic acid derived esters, such as isopropyl lanolate, isocetyl lanolate, monoglycerides, diglycerides and triglycerides of fatty acids such as glycerol triheptanoate, alkylbenzoates, hydrogenated oils, poly (alpha-olefin), polyolefins such as polyisobutane ) synthetic isoalkanes such as isohexadecane, isododecane, perfluorinated oils; silicone oils such as dimethylpolysiloxanes, methylphenylpolysiloxanes, amine-modified silicones, fatty acid-modified silicones, alcohols-modified silicones, alcohol-modified silicones and fatty acids, modified silicones, polyether groups, modified epoxy silicones, silicones modified with fluorinated groups, cyclic silicones and silicones modified with alkyl groups. By "oils" is meant herein the compounds and / or the mixtures of water-insoluble compounds having a liquid appearance at a temperature of 25 ° C. As examples of waxes that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of bee, carnauba wax, candelilla wax, ouricoury wax, japanese wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite waxes, waxes microcrystalline, lanolin wax; ozokerite; polyethylene wax; silicone waxes; vegetable waxes; fatty alcohols and solid fatty acids at room temperature; glycerides solid at room temperature. By "waxes" is meant in the present application the compounds and / or mixtures of compounds insoluble in water, having a solid appearance at a temperature greater than or equal to 45 ° C. As examples of active principles that can be associated with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of vitamins and their derivatives, especially their esters, such as retinol (vitamin A) and its esters (retinyl palmitate for example), ascorbic acid (vitamin C) and its esters, ascorbic acid sugar derivatives (as ascorbyl glucoside), tocopherol (vitamin E) and its esters (such as tocopherol acetate), vitamins B3 or B10 (niacinamide and its derivatives); compounds showing a lightening or depigmenting action on the skin, such as w-undecelynoyl phenylalanine marketed under the name SEPIVVHITETmMSH, SEPICALMTmVG, the mono ester and / or the glycerol diester of w-undecelynoyl phenylalanine, the w-undecelynoyl dipeptides, l arbutin, kojic acid, hydroquinone; the compounds showing a soothing action, especially SEPICALM ™ S, allantoin and bisabolol; anti-inflammatory agents; compounds showing a moisturizing action such as urea, hydroxyureas, glycerol, polyglycerols, glycerolglucoside, diglycerolglucoside, polyglycerylglucosides, xylitylplucoside; plant extracts rich in polyphenols such as grape extracts, pine extracts, wine extracts, olive extracts; compounds showing a slimming or lipolytic action such as caffeine or its derivatives, ADIPOSLIM ™, ADIPOLES ™, fucoxanthin; N-acylated proteins; N-acylated peptides such as MATRIXIL ™; N-acyl amino acids; partial hydrolysates of N-acylated proteins; amino acids; peptides; total hydrolysts of protein; soy extracts, for example Raffermine TM; wheat extracts for example TENSINETm or GLIADINETm; plant extracts, such as tannin-rich plant extracts, plant extracts rich in isoflavones or plant extracts rich in terpenes; freshwater or marine algae extracts; marine plant extracts; marine extracts in general such as corals; essential waxes; bacterial extracts; ceramides; phospholipids; compounds exhibiting antimicrobial action or purifying action, such as LIPACIDETM C8G, LIPACIDETM UG, SEPICONTROL ™ A5; OCTOPIROXTm or SENSIVATM SC50; compounds showing an energizing or stimulating property such as PHYSIOGENYL ™, panthenol and its derivatives such as SEPICAP ™ MP; anti-aging actives like SEPILIFTTm DPHP, LIPACIDETM PVB, SEPIVINOLTM, SEPIVITALTm, MANOLIVATm, PHYTO-AGETm, TIMECODETm; SURVICODETM; anti-aging photo active ingredients; the active ingredients protecting the integrity of the dermal-epidermal junction; actives enhancing the synthesis of extracellular matrix components such as collagen, elastins, glycosaminoglycans; assets acting favorably on chemical cellular communication such as cytokines or physical ones such as integrins; active ingredients that create a sensation of "heating" on the skin, such as activators of cutaneous microcirculation (such as nicotinic acid derivatives) or products that create a sensation of "freshness" on the skin (such as menthol and derivatives) ; the active agents improving cutaneous microcirculation, for example the venotonic ones; draining assets; decongestant active ingredients such as extracts of ginko biloba, ivy, horse chestnut, bamboo, ruscus, holly, centalla asiatica, fucus, rosemary, willow; tanning agents or skin browning agents, such as dihydroxyacetone, isatin, alloxane, ninhydrin, glyceraldehyde, mesotartaric aldehyde, glutaraldehyde, erythrulose. Examples of antioxidants that can be combined with the compound of formula (I) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention include EDTA and its salts, citric acid, tartaric acid, oxalic acid, BHA (butylhydroxyanisole), BHT (butylhydroxytoluene), tocopherol derivatives such as tocopherol acetate, mixtures of antioxidant compounds such as DISSOLVINETM GL 47S marketed by Akzo Nobel under the name INCI: Tetrasodium Glutamate Diacetate. As examples of sunscreens that can be combined with the compound of formula (1) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of all those contained in Cosmetic Directive 76/768 / EEC as amended Annex VII.
[0014] Among the solar organic filters that can be combined with the compound of formula (1) or with the composition (Cl) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of the family derivatives of benzoic acid such as para-aminobenzoic acids (PABA), in particular monoglycerol esters of PABA, ethyl esters of N, N-propoxy PABA, ethyl esters of N, N-diethoxy PABA, ethyl esters N, N-dimethyl PABA, N, N-dimethyl PABA methyl esters, N, N-dimethyl PABA butyl esters; the family of anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate; the family of salicylic acid derivatives such as amyl salicylate, homomenthyl salicylate, ethylhexyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropanolphenyl salicylate; the family of cinnamic acid derivatives such as ethylhexyl cinnamate, ethyl-4-isopropyl cinnamate, methyl-2,5-diisopropyl cinnamate, p-methoxypropyl cinnamate and p-methoxyisopropyl cinnamate; , pmethoxyisoamyl cinnamate, p-methoxyoctyl cinnamate (p-methoxy-2-ethylhexyl cinnamate), p-methoxy-2-ethoxyethyl cinnamate, p-methoxycyclohexyl cinnamate, ethyl-cinnamate -cyano-8-phenyl, 2-ethylhexyl-α-cyano-8-phenyl cinnamate, glyceryl diparamethoxy mono-2-ethylhexanoyl cinnamate; the family of benzophenone derivatives such as 2,4-dihydroxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2 ', 4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenylbenzophenone-2-carboxylate, 2-hydroxy-2-hydroxybenzophenone, 4-n-octyloxybenzophenone, 4-hydroxy-3-carboxybenzophenone; 3- (4'-methylbenzylidene) -d, 1-camphor, 3- (benzylidene) -d, 1-camphor, benzalkonium methosulfate camphor; urocanic acid, ethyl urocanate; the family of sulfonic acid derivatives such as sulfonic acid 2-phenylbenzimidazole-5 and its salts; the family of triazine derivatives such as hydroxyphenyl triazine, ethylhexyloxyhydroxyphenyl-4-methoxyphenyltriazine, 2,4,6-trianillino- (p-carbo-2'-ethylhexyl-t-oxy) -1,3,5 triazine, 4,4 - ((6 - ((((1,1-dimethylethyl) amino) carbonyl) phenyl) amino) -1,3,5-triazine-2,4-diyl diimino) bis- (2- ethylhexyl) benzoic acid ester, 2-phenyl-5-methylbenzoxazole, 2,2'-hydroxy-5-methylphenylbenzotriazole, 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole, 2 - (2'-hydroxy-5'-methylphenyl) benzotriazole; dibenzazine; dianisoylmethane, 4-methoxy-4 "-t-butylbenzoylmethane, 5- (3,3-dimethyl-2-norbornylidene) -3-pentan-2-one, the family of diphenylacrylate derivatives such as 2-ethylhexyl- 2-cyano-3,3-diphenyl-2-propenoate, ethyl-2-cyano-3,3-diphenyl-2-propenoate, the family of polysiloxanes such as benzylidene malonate siloxane, among the inorganic solar filters, also called "inorganic screens", which can be combined with the compound of formula (1) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of the titanium oxides, zinc oxides, cerium oxide, zirconium oxide, iron oxides yellow, red or black, chromium oxides These inorganic screens can be micronized or not, whether or not they have undergone surface treatments and may optionally be presented in the form of aqueous or oily pre-dispersions. It also relates to a compound of formula (1) or a composition (Cl) as defined above, for use in a method of therapeutic treatment of signs of aging of human skin or lips applied to the human body. The following examples illustrate the invention without limiting it.
[0015] Example I: Preparation of a Composition (C18) According to the Invention 500 grams of alanine, ie one molar equivalent, are introduced into a hydroalcoholic mixture consisting of 1.800 grams of water and 200 grams of isopropanol at a temperature of 20 ° C. The pH of the medium is adjusted to 10 by addition of a 30% sodium hydroxide solution. 731.7 grams of octanoyl chloride, ie 0.8 molar equivalents, are then gradually added to the mixture maintained between 20 ° C. and 50 ° C. and at a pH of between 10 and 10.5. The reaction medium is then stirred for two hours and then heated to 70 ° C, then added 979.6 grams of a 75% phosphoric acid solution to gradually reach a pH value of 2 , 0.
[0016] The aqueous phase of the medium is decanted and withdrawn and the organic phase remaining in the reactor is washed several times with brine at room temperature with stirring. After washing and then drying by vacuum distillation of the residual water, the organic phase comprising 922.3 grams of desired N-octanoyl alanine is obtained. 133.8 grams of isosorbide, ie one molar equivalent, are introduced with stirring into the reactor comprising a fraction of the preceding organic phase, in which there is 0.8 molar equivalent of N-octanoyl alanine. The temperature is raised to 120 ° C. 0.73 grams of 98% sulfuric acid and 0.73 grams of 50% hypophosphorous acid are then added and the resulting mixture heated to 125 ° C under partial vacuum with nitrogen sparge. The reaction mixture is then maintained for 10 hours with stirring at this temperature, then neutralized by addition of a 30% sodium hydroxide solution so as to obtain a pH of the composition (C1A), diluted to 5% in water, between 3.0 and 6.0. The analytical characteristics of the composition (C1A) obtained are as follows: Acidic index (according to the NFT 60-204 method) = 60.3 pH 5% of the composition A in water (according to the method NFT 73-206) = 3.7 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 261.9 Ester number (calculated as the difference between the saponification number measured according to the method NFT 60-110 and the index d acid measured according to the method NFT 60-204) = 104.4 Saponification number (according to NFT 60-206) = 164.7 mg KOH / g Exem the 2nd aration of an IPC composition according to the invention. The procedure of the process described in Example 1 is carried out by replacing the molar equivalent of alanine with a molar equivalent of valine and the 0.8 molar equivalent of octanoyl chloride with 0.8 molar equivalents of chloride. of (w-undecylenoyl) to obtain the composition (C1B), the analytical characteristics of which are as follows: acid number (according to NFT 60-204) = 35.4 pH 5% of the composition (C1B) in water (according to NFT method 73-206) = 5.0 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 155.8 Ester number (calculated by the difference between the saponification number measured according to the NFT method 60-110 and the acid number measured according to the NFT method 60-204) = 91.3 Saponification number (according to NFT 60-206) = 126.7 mg KOH / g Exem the 3rd ation of a com according to the invention.
[0017] The procedure of the process described in Example 1 is carried out by replacing the molar equivalent of alanine with a molar equivalent of valine and the 0.8 molar equivalent of octanoyl chloride with 0.8 molar equivalents of chloride. of hexadecanoyl obtain the Composition (CID) whose analytical characteristics are as follows: Acid number (according to NFT 60-204) = 12.3 pH 5% of the composition (CID) in water (according to the NFT method 73- 206) = 7.5 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 100.2 Ester number (calculated as the difference between the saponification number measured according to the method NFT 60-110 and acid number measured according to the method NFT 60-204) = 96.2 Saponification number (according to NFT 60-206) = 108.5 mg KOH / g Exem the 4th ation of a CID composition according to US Pat. invention. The procedure of the method described in Example 1 is carried out by replacing the molar equivalent of alanine with a molar equivalent of isoleucine, to obtain the composition (Cl D), the analytical characteristics of which are as follows: (according to NFT 60-204) = 71.5 pH 5% of composition E in water (according to the method NFT 73-206) = 4.1 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 219.8 Ester number (calculated as the difference between the saponification number measured according to the NFT method 60-110 and the acid number measured according to the NFT method 60-204) = 86.2 Saponification index (according to NFT 60-206) = 157.7 mg KOH / g Exem the 5th aeration of a CIE composition according to the invention.
[0018] The procedure of the process described in Example 1 is carried out by replacing the molar equivalent of alanine with a molar equivalent of isoleucine, and the 0.8 molar equivalent of octanoyl chloride with 0.8. molar equivalent of cocoyl chloride, to obtain the Composition (CIE) whose analytical characteristics are as follows: Acid value (according to NFT 60-204) = 68.0 pH 5% of the composition (CIE) in water (according to the method NFT 73-206) = 5.2 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 188.5 Ester number (calculated by the difference between the saponification number measured according to the NFT method 60-110 and the acid number measured according to the method NFT 60-204) = 54.7 Saponification number (according to NFT 60-206) = 122.7 mg KOH / g The said cocoyl chloride used in the preparation of the composition (CIE) comprises, for 100% of its mass, 8% by weight of octanoyl chloride, 8% by weight of decanoyl chloride, 50% by weight of of lauroyl chloride, 17% by weight of myristoyl chloride, 8% by weight of palmitoyl chloride, 3% by weight of stearoyl chloride, 4% by weight of oleoyl chloride and 2% by weight of linoleoyl chloride. Demonstration of anti-aging activity of the compounds and compositions according to the invention by an in vitro study of the migration of human fibroblasts. The demonstration of anti-aging activity of the compositions according to the invention was carried out by the implementation of a study model consisting in studying the migratory capacity of normal human fibroblasts treated or not with the compositions according to the invention. and references. The fibroblast migration test is a test commonly used in the cosmetics and pharmacy sector and described in particular in the international application published under the number VVO 2010/056908 A1. It makes it possible to reproduce in vitro the phenomenon of fibroblast migration. ; a decrease in the migratory capacities of fibroblasts being reported as associated with skin aging (1) (4). Protocol: Normal human Fibroblasts at the R5 passage were amplified in T75 culture flask and then seeded at 25,000 cells / well in specific culture plates. These are dedicated to migration (OrisTM of Platypus), integrating a central zone without initial cell deposition (stoppers). After 96 hours of amplification in plate, and 2 hours before the treatment, all the wells were treated with Mitomycin C (2h to 10pg / ml), in order to stop the cell proliferation, and thus observe only the phenomenon of migration. The stoppers were removed, and references, products, or standard medium for Fibroblasts with 2% Fetal Calf Serum (FCS) were applied to the cells under 100p1, then incubated for 40h at 37 ° C under 5%. of CO2. Each condition was carried out in quadriplicate Evaluation of the effects: At the end of the incubation, labeling of cells with Calcein AM was carried out (5 μM, 20 minutes at 37 ° C.), in order to visualize the viable cells in fluorescence. (revelation of the cytoplasm). Photos were made, after inserting a black cache under the culture plates, in order to visualize only the area where the cells were not deposited. Thus, only migrated cells were photographed (x4 lens, with a reducer on the camera adapter x 0.7). The average cell migration distance (D, ', gr) was measured with NIS-Elements-BR 3.0 (4 cells). Mean and standard deviation of distances were calculated for quadriplicates. The percentages of migratory effect relative to the control, as well as statistics (Student's test) were also calculated. Results: The results obtained are recorded in Table 1 below: Table 1: Migration of fibroblasts in the presence of the compositions tested Products tested (w / v) (Dmigr) in pm [(Dmigr) - (D. 1 111D igritémoin, control, control migro1 SVF (20 mg / ml) 168 ± 34 Epidermal Growth Factor (EGF) 10ng / ml 203 ± 20 + 21% Epidermal Growth Factor (EGF) 5Ong / ml 212 ± 8 + 26% Composition (C1A) (5pg / m1) 206 ± 35 + 23% Composition (C1A) (10 μg / ml) 188 ± 23 + 12% Composition (C1B) (5 μg / ml) 190 ± 23 + 13% Composition (C1B) (10 μg / ml) 195 ± 13 + 16% Composition (CID) (5 μg / ml) 198 ± 17 + 18% Composition (CID) (10 μg / ml) 188 ± 9 + 12% Composition (CID) (5 μg / ml) 181 ± 11 + 8 % Composition (C1 D) (10 μg / ml) 188 ± 15 + 12% Composition (CIE) (5 μg / ml) 197 ± 3 + 17% Composition (CIE) (10 μg / ml) 192 ± 9 + 14% The combination of EGF, at 10 and 50ng / ml, with normal human fibroblasts show an increase in the migration distance of said fibroblasts, thus validating the chosen model. The combination of compositions (C1A), (C1B), (CID), (C1D) and (C1D) with normal human fibroblasts show a significant increase in the migration distance of said fibroblasts, and consequently an improvement in the migratory properties of fibroblasts. of the dermis of the human skin, thus constituting an effective means of preventing and / or treating the aging of the skin of the human body and the lips.
[0019] Bibliography (1): Schulze et al., "Stiffening of human skin fibroblasts with age;" Clinic Piast.Get; 2012; 39 (1): 9-20. (2): Baraibar and Friguet, "Oxidative proteome modifications target Specific cellular pathways during oxidative stress, cellular senescence and aging "Exp Gerontol; 2013; 48 (7): 620-5. (3): Kondo et al.," Inhibitory effects of human serum on human fetal skin fibroblast migration: migration -inhibitory activity and substances in serum, and its age-related changes "; Vitro Cell Dey Biol Anim; 2000; 36 (4): 256-61. (4): Jang et al., Prolonged activation of ERK contributes to the photorejuvenation effect in photodynamic therapy in human dermal fibroblasts; JID; 2013; 133 (9): 2265-75. (5): Houreld and Abrahamse "Low-intensity laser irradiation stimulators wound healing in diabetic wounded fibroblast cells (VVS1)", 2010 , Diabetes Technol Ther, Dec; 12 (12) (6): Tang et al., "A rice-derived recombinant human lactoferrin stimulants fibroblast proliferation, migratory ion, and sustains cell survive ', 2010, Wound Repair Regen, Jan-Feb 18 (1) (7): Demirovic and Rattan, "Curcumin induces stress response and hormetically modulates wound healing ability of human skin fibroblasts undergoing aging in vitro" , 2011, Biogerontology, Mar 6 (8): Rojo et al., "VVound healing properties of nut or l from Pouteria lucuma", 2010, Cosmet Dermatol J, Sep 9 (3) (9): Karleskind A., 1992. Manual of fatty substances, Lavoisier, Vol. 1 and 2: 65-78, 115-241, 1072-1089, 1433-1459.25

权利要求:
Claims (11)
[0001]
CLAIMS1 Use of a compound of formula (1): OR "R'0 (I), in which R 'and R", which are identical or different, represent either a hydrogen atom or a monovalent radical of formula (11a): Wherein R1-C (= O) - represents an acyl radical, saturated or unsaturated, linear or branched, having from eight to thirty carbon atoms, the radical R2 represents a hydrogen atom or a radical chosen from methyl, isopropyl, isobutyl, 1-methylpropyl, hydroxymethyl, 1-hydroxyethyl and thiomethyl radicals,
[0002]
2-methylthioethyl, 4-amino butyl,
[0003]
3-guanidino propyl, 3-ureido propyl, (1-amino carbonyl) methyl, carboxymethyl, 2-carboxyethyl, 2- (amino carbonyl) ethyl, benzyl,
[0004]
4-hydroxybenzyl, 3,4-dihydroxybenzyl, [1H-indol-3-yl] methyl, (1H-imidazol-4-yl) methyl and 3-aminopropyl, and the radical R3 represents a hydrogen atom or a methyl radical; is a monovalent radical of formula (Ib): ## STR5 ## in which R 1-C (= O) - is as defined in formula (11a) and R 4 represents a a hydrogen atom or a hydroxyl radical, it being understood that in said formula (1), at least one of the radicals R 'or R "does not represent a hydrogen atom and that when none of the radicals R' and R" represents a hydrogen atom, R 'and R "are identical, or a mixture of compounds of formulas (1), said use being for the purpose of preventing or slowing down the appearance of the signs of aging of human skin or lips or to eliminate said signs and said use being in a cosmetic composition 2. Use as defined in claim 1, a composition (Cl) comprising for 100% of its mass: - 99% mass at 20% by weight of at least one compound of formula (Ia) OH R'O (Ia), formula (Ia) in which R 'represents either a monovalent radical of formula (11a): O R2 (11a), formula (11a) in which the group R1-C (= O) - represents an acyl radical, saturated or unsaturated, linear or branched, having from eight to thirty carbon atoms, the radical R2 represents a hydrogen atom or a radical chosen from methyl, isopropyl, isobutyl, 1-methylpropyl, hydroxymethyl, 1-hydroxyethyl, thiomethyl, 2-methylthioethyl, 4-aminobutyl and 3-guanidinopropyl radicals; , 3-ureido propyl, (1-amino carbonyl) methyl, carboxymethyl, 2-carboxyethyl, 2- (amino carbonyl) ethyl, benzyl, 4-hydroxybenzyl, 3,4-dihydroxybenzyl, [1H-indo] -3- yl] methyl, (1H-imidazol-4-yl) methyl and 3-amino propyl, and the radical R3 represents a hydrogen atom or a methyl radical; is a monovalent radical of formula (11b): R4INO R1 (11b), formula (11b) in which the group R1-C (= O) - is as defined in formula (11a) and R4 represents an atom of hydrogen or a hydroxy radical, and - from 1 wt.% to 80 wt.% of at least one compound of formula (Ib): OR RO (Ib), wherein R is a monovalent radical of formula (11a) R1 0 R3 0 (11a), wherein R1-C (= O) - represents an acyl radical, saturated or unsaturated, linear or branched, having from eight to thirty. carbon atoms, the radical R2 represents a hydrogen atom or a radical chosen from the radicals methyl, isopropyl, isobutyl, 1-methylpropyl, hydroxymethyl, 1-hydroxyethyl, thiomethyl, 2-methylthioethyl, 4-amino butyl, 3-guanidino propyl, 3-ureido propyl, (1-amino carbonyl) methyl, carboxymethyl, 2-carboxyethyl, 2- (amino carbonyl) ethyl, benzyl, 4-hydroxybenzyl, 3,4-dihydroxybenzyl e, [1H-indol-3-yl] methyl, (1H-imidazol-4-yl) methyl and 3-amino propyl, and the radical R3 represents a hydrogen atom or a methyl radical; is a monovalent radical of formula (11b): R 4 / 4N O 0 (11b), formula (11b) in which the group R 1 -C (= O) - is as defined in formula (11a) and R 4 represents an atom hydrogen or a hydroxy radical. 3. Use as defined in any one of claims 1 or 2, wherein said signs of aging of human skin or lips are wrinkles, fine lines or an alteration of the microrelief of human skin or lips. 4. Use as defined in any one of claims 1 or 2, wherein said signs of aging of human skin or lips are lack of elasticity and / or tone of human skin or lips.
[0005]
5. Use as defined in any one of claims 1 or 2, wherein said signs of aging of human skin or lips are lack of density and / or firmness of human skin or lips.
[0006]
6. Use as defined in any one of claims 1 to 5 wherein the radicals R 'and R ", identical or different, in the formula (I) represent either a hydrogen atom or a monovalent radical of formula (IIa), wherein R 1 -C (= O) - and R 3 are as previously defined and R 2 represents a radical selected from methyl, isopropyl, isobutyl or 1-methylpropyl radicals.
[0007]
7. Use as defined in claim 6 wherein in the formula (IIa), the group R1-C (= O) - is selected from octanoyl, decanoyl, w-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl or 9,12-octadecadienoyl, R3 represents a hydrogen atom, and R2 represents a radical chosen from methyl, isopropyl, isobutyl or 1-methylpropyl radicals.
[0008]
8. A method for preventing or slowing the appearance of signs of aging of human skin or lips or for eliminating said signs, comprising at least one application step on human skin or lips of a cosmetic formulation for topical use comprising at least one cosmetically acceptable excipient and an effective amount of at least one compound of formula (I): OR "R'0 (I), in which R 'and R", which are identical, or different, represent either a hydrogen atom; or a monovalent radical of formula (IIa): ## STR5 ## wherein formula (IIa) in which the group R1-C (= O) - represents an acyl radical, saturated or unsaturated, linear or branched, having from eight to thirty carbon atoms, the radical R 2 NR 1 R 3 0 represents a hydrogen atom or a radical chosen from methyl, isopropyl, isobutyl, 1-methylpropyl, hydroxymethyl, 1-hydroxyethyl, thiomethyl and 2-methylthioethyl radicals, 4-Amino butyl, 3-guanidino propyl, 3-ureido propyl, (1-amino carbonyl) methyl, carboxymethyl, 2-carboxyethyl, 2- (amino carbonyl) ethyl, benzyl, 4-hydroxybenzyl, 3,4-dihydroxy benzyl, [1H-indol-3-yl] methyl, (1H-imidazol-4-yl) methyl and 3-amino propyl, and the radical R3 represents a hydrogen atom or a methyl radical; is a monovalent radical of formula (11b): R 4 'N 1 O R 1 0 (11b), formula (11b) in which the group R 1 -C (= O) - is as defined in formula (11a) and R 4 represents a hydrogen atom or a hydroxyl radical, it being understood that in said formula (1), at least one of the radicals R 'or R "does not represent a hydrogen atom and that when none of the radicals R' and R" represents a hydrogen atom, R 'and R "are identical.
[0009]
9. A method for preventing or slowing the appearance of signs of aging of human skin or lips or eliminating said signs, comprising at least one application step on human skin or lips, a cosmetic formulation for topical use comprising at least one cosmetically acceptable excipient and an effective amount of the composition (Cl) comprising for 100% of its mass: from 99% by weight to 20% by weight of at least one compound of formula wherein R 'represents either a monovalent radical of formula (IIa): wherein R' R1-C (= O) - represents an acyl radical, saturated or unsaturated, linear or branched, comprising from eight to thirty carbon atoms, the radical R2 represents a hydrogen atom or a radical chosen from methyl, isopropyl radicals, isobutyl, 1-methylpropyl, hydroxymethyl, 1-hydroxyethyl, thiomethyl, 2-m ethylthioethyl, 4-aminobutyl, 3-guanidinopropyl, 3-ureidopropyl, (1-aminocarbonyl) methyl, carboxymethyl, 2-carboxyethyl, 2- (aminocarbonyl) ethyl, benzyl, 4-hydroxybenzyl, 3, 4-dihydroxybenzyl, [1H-indol-3-yl] methyl, (1H-imidazol-4-yl) methyl and 3-aminopropyl, and the radical R3 represents a hydrogen atom or a methyl radical; a monovalent radical of formula (11b): ## STR5 ## wherein formula R 1 -C (= O) - is as defined in formula (11a) and R 4 represents an atom of hydrogen or a hydroxy radical, and - from 1 wt.% to 80 wt.% of at least one compound of formula (lb): OR RO (lb), formula (lb) wherein R represents either a monovalent radical of formula (11a) R1 / N / 1 R3 0 (11a), wherein R1-C (= O) - represents a saturated or unsaturated acyl radical, linear or branched, having from eight to thirty carbon atoms, the radical R2 represents a hydrogen atom or a radical chosen from methyl, isopropyl, isobutyl, 1-methylpropyl, hydroxymethyl, 1-hydroxyethyl, thiomethyl, 2-methylthioethyl, 4-amino-butyl radicals; , 3-guanidino propyl, 3-ureido propyl, (1-amino carbonyl) methyl, carboxymethyl, 2-carboxyethyl, 2- (amino carbonyl) ethyl, benzyl, 4-hydroxybenzyl, 3,4-dihydroxybenzyl , [1H-indol-3-yl] methyl, (1H-imidazol-4-yl) methyl and 3-amino propyl, R4 / 4Net the radical R3 represents a hydrogen atom or a methyl radical; or a monovalent radical of formula (11b): ## STR5 ## in which the group R 1 -C (= O) - is as defined in formula (11a) and R 4 represents an atom hydrogen or a hydroxy radical.
[0010]
10. Compound of formula (1): OR "R'0 (I), in which R 'and R", which are identical or different, represent either a hydrogen atom; or a monovalent radical of formula (IIa): ## STR2 ## in which R 1 -C (= O) - represents an acyl radical, saturated or unsaturated, linear or branched, comprising from 8 to 30 carbon atoms, the radical R 2 represents a hydrogen atom or a radical chosen from methyl, isopropyl, isobutyl, 1-methylpropyl, hydroxymethyl, 1-hydroxyethyl, thiomethyl and 2-methylthioethyl radicals, 4 butyl amine, 3-guanidino propyl, 3-ureido propyl, (1-amino carbonyl) methyl, carboxymethyl, 2-carboxyethyl, 2- (amino carbonyl) ethyl, benzyl, 4-hydroxybenzyl, 3,4-dihydroxybenzyl , [1H-indol-3-yl] methyl, (1H-imidazol-4-yl) methyl and 3-amino propyl, and the radical R3 represents a hydrogen atom or a methyl radical; is a monovalent radical of formula (11b): (11b), formula (11b) in which the group R1-C (= O) - is as defined in formula (11a) and R4 represents a hydrogen atom or a hydroxy radical, it being understood that in said formula (1), at least one of the radicals R 'or R "does not represent a hydrogen atom and that when none of the radicals R' and R" represents a hydrogen atom , R 'and R "are identical, for its use in a method of therapeutic treatment of signs of aging of human skin or lips applied to the human body.
[0011]
11. Composition (Cl) comprising for 100% of its mass: from 99% by mass to 20% by weight of at least one compound of formula (Ia) OH R'O (la), formula (Ia) corresponding to the formula (1) as defined in claim 1, wherein R "represents a hydrogen atom, and - from 1 wt% to 80 wt% of at least one compound of formula (lb): OR RO (lb), formula (Ib) corresponding to the formula (1) as defined in claim 1, in which the radicals R 'and R "are identical and are represented by the radical R, for use in a method of therapeutic treatment of the signs of the aging of human skin or lips applied to the human body.

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EP3720567A1|2020-10-14|Novel method for reducing the effects of blue-light-induced stress on the skin

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WO2018020101A1|2018-02-01|Method for obtaining a unialgal biomass of cells of small multicellular macroalgae and endophytes of host macroalgae, and use of same in cosmetics

同族专利:

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公开号 | 公开日

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WO2016062948A1|2016-04-28|

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US20170304177A1|2017-10-26|

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CN107106448A|2017-08-29|

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KR20170106292A|2017-09-20|

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JP2017531658A|2017-10-26|

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EP3209277A1|2017-08-30|

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FR3027518B1|2018-01-19|

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FR3090354A1|2018-12-20|2020-06-26|Roquette Freres|Anti-aging agent and cosmetic composition comprising it|

法律状态:
2015-10-23| PLFP| Fee payment|Year of fee payment: 2 |

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2016-04-29| PLSC| Publication of the preliminary search report|Effective date: 20160429 |

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2016-10-20| PLFP| Fee payment|Year of fee payment: 3 |

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2017-10-24| PLFP| Fee payment|Year of fee payment: 4 |

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2018-10-22| PLFP| Fee payment|Year of fee payment: 5 |

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2019-10-28| PLFP| Fee payment|Year of fee payment: 6 |

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2020-10-21| PLFP| Fee payment|Year of fee payment: 7 |

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2021-10-21| PLFP| Fee payment|Year of fee payment: 8 |

优先权:

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申请号 | 申请日 | 专利标题

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FR1460254A|FR3027518B1|2014-10-24|2014-10-24|USE OF ISOSORBIDE ESTER AND N-ACYL DERIVATIVES OF AMINO ACIDS AS AN ANTI-AGING AGENT FOR HUMAN SKIN|

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FR1460254|2014-10-24|FR1460254A| FR3027518B1|2014-10-24|2014-10-24|USE OF ISOSORBIDE ESTER AND N-ACYL DERIVATIVES OF AMINO ACIDS AS AN ANTI-AGING AGENT FOR HUMAN SKIN|

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US15/518,387| US20170304177A1|2014-10-24|2015-10-16|Use of isosorbide ester and n-acylated amino acid derivatives as anti-ageing agent for the human skin|

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CN201580054212.0A| CN107106448A|2014-10-24|2015-10-16|Coronex and N acylated amino groups acid derivative as the age resister for application on human skin purposes|

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EP15797121.9A| EP3209277A1|2014-10-24|2015-10-16|Use of isosorbide ester and n-acylated amino acid derivatives as anti-ageing agent for the human skin|

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PCT/FR2015/052791| WO2016062948A1|2014-10-24|2015-10-16|Use of isosorbide ester and n-acylated amino acid derivatives as anti-ageing agent for the human skin|

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JP2017518435A| JP2017531658A|2014-10-24|2015-10-16|Use of isosorbide esters and N-acylated amino acid derivatives as anti-aging agents for human skin|

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KR1020177011556A| KR20170106292A|2014-10-24|2015-10-16|Use of isosorbide ester and n-acylated amino acid derivatives as anti-ageing agent for the human skin|