• 专利附录
  • 专利说明
  • 权利要求
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    • 专利摘要:
    The present invention relates to a combination comprising a hyaluronic acid or a salt thereof and a sulfated polysaccharide whose molecular weight is between 5 and 25 kDa, useful in particular for combating the signs of skin aging or for treating and healing cutaneous lesions.
    公开号:FR3020570A1
    申请号:FR1453973
    申请日:2014-04-30
    公开日:2015-11-06
    发明作者:Stephane Poigny；Helene Hernandez-Pigeon；Jean Hilaire Saurat；Gurkan Kaya
    申请人:Pierre Fabre Dermo Cosmetique SA；
    IPC主号:
    专利说明:

    [0001] FIELD OF THE INVENTION The present invention relates to a novel combination of a hyaluronic acid or a salt thereof and a low molecular weight sulfated polysaccharide; and the use of said combination in the fields of anti-aging and scarring. PRIOR ART Hyaluronic acid (HA) is a molecule with a major role in the skin. This is indeed the main component of the extracellular matrix. The latter refers to the set of extracellular macromolecules of the connective tissue. It consists largely of glycoproteins, pure proteins and glycosaminoglycans. HA is a non-sulphated linear glycosaminoglycan composed of repeating units of disaccharides themselves composed of D-glucuronic acid and N-acetyl-Dglucosamine linked by alternating glycosidic bonds (31-3 and (31-4 between dimers) ( Tammi R., Agren UM, Tuhkanen AL, Tammi M. Hyaluronan metabolism in skin, Progress in Histochemistry & Cytochemistry 29 (2): 1-81, 1994. In its native form, HA is a very high-weight polymer. molecular weight ranging from 600,000 Da to 3 MDa (Hyaluronan Toole BP: from extracellular glue to peracellular cue, Nat Rev Cancer 2004, 4: 538-539).
    [0002] With age, the amount of HA and its degree of polymerization decrease, resulting in less water retained in the extracellular matrix. The skin then undergoes an aging process which results in an increase in fibrosis and a decrease in the content of elastic fibers. During the aging process, there is a change in the structure and cutaneous functions. This aging is of physiological nature but can also be photoinduced, that is to say due to repeated exposure of the skin to sunlight, especially ultraviolet. The main clinical signs of skin aging are the appearance of fine lines and deep wrinkles, which obviously increase with age. The furrows and wrinkles are marked; the skin becomes hollow and loses its firmness; on the surface, the skin loses its luminosity.
    [0003] Sulphated polysaccharides comprise, inter alia, sulphated fucans and sulphated ulvans with a molecular weight of between 5 and 25 kDa.
    [0004] These low molecular weight sulfated polysaccharides have interesting biological properties: inhibition of collagen and elastin degradation, restructuring, anti-inflammatory action, and induction of HA production.
    [0005] During aging, fibroblasts enter senescence and their proliferation capacity decreases sharply. Thus, the fact of being able to stimulate again the proliferation of these cells is one of the ways studied to fight against skin aging.
    [0006] In addition, wound healing is a complex and dynamic biological process that involves the interaction of many local and systemic factors in normal tissue repair. The progress of wound healing has three interrelated phases: hemostasis and inflammation, proliferation, and remodeling (Witte, MB, Barbul A. Surg Clin North Am., 1997 Jun; 77 (3): 509). -28.). Proliferation involves three observable processes: granulation, contraction and re-epithelialization. During granulation, there is proliferation and migration to the wound bed of the cells that will be involved in the rest of the repair process. Thus, macrophages, fibroblasts and endothelial cells are found. Macrophages are constantly releasing chemotactic factors and growth factors. Fibroblasts build the new cell matrix necessary for cell growth at the bottom of the wound. This scaffold promotes cell migration. Finally, the endothelial cells trigger the formation of vascular buds that will form new capillaries, which will restore the perfusion and ensure the supply of oxygen and nutrients essential to the metabolic activity of cells in the wound. The contraction of the wound is a mechanism for reducing the size of the wound and the fibroblasts play a leading role in this contraction. Re-epithelialization is the regeneration of an epidermis that covers a wound to reform an effective barrier against the external environment, capable of pigmentation and regain its sensory and immune functions. It therefore involves the cellular processes of migration and proliferation of keratinocytes, but also the differentiation of this neoepithelium and the restoration of a basement membrane that reconnects the dermis and the epidermis. When the migration of basal cells towards the wound center allows both edges of the wound to join, a wave of cellular mitosis occurs to fill the spaces left by the migration and provide cells for regenerating epithelial tissue. -dimensional. The proliferation steps of keratinocyte cells, fibroblasts or endothelial cells can be considered as one of the functional phenomena testifying to the healing activity of an active ingredient. An increase in fibroblast proliferation would participate in the healing of a deep wound (damage to the dermis), whereas the increase in keratinocyte proliferation would participate in reepithelialization. There is still a need to propose new cosmetic compositions to combat the signs of skin aging. The applicant has demonstrated the existence of a synergy between hyaluronic acid and a low molecular weight sulphated polysaccharide on the proliferation of fibroblasts. This activity is particularly interesting in the field of anti-aging but also in tissue regeneration and healing of skin lesions. DETAILED DESCRIPTION The subject of the present invention is an association comprising a hyaluronic acid or one of its salts and a sulphated polysaccharide whose molecular weight is between 5 and 25 kDa. In the context of the present invention, the terms "hyaluronic acid", "fragments of hyaluronic acid", "AH" and "hyaluronan" are used interchangeably to designate hyaluronic acid. When hyaluronic acid is in salt form, it will be called hyaluronate.
    [0007] In a particular embodiment of the invention, the combination comprises a hyaluronic acid or one of its salts whose weight average molecular weight (Mw) will be between 50,000 and 750,000 Da. In a particular embodiment of the invention, the AH fragment or a salt thereof is characterized by a weight average molecular weight of between 60 and 120 kDa, said molecular mass being measured by an analytical method combining a Size Exclusion Chromatography (SEC) with a Multi-Angle Light Scattering Photometer (MALS) coupled to a Viscometer (VIS) and a Differential Refractometer (RI). In a particular embodiment, it will be sodium hyaluronate. The molecular weight of HA or a salt can be measured using the European Pharmacopoeia method, which measures intrinsic viscosity with a Ubbelohde capillary viscometer (see European Pharmacopoeia 7.6, sodium hyaluronate monograph ref. .: 01/2011: 1472). This viscosity value is then related to the average molecular weight by the Mark-Houwink relationship. This method is long and requires perfect reproducibility. In the context of the present invention, the weight average molecular weight of HA or a salt thereof is measured by the SEC-MALS-VIS-RI method, which is an analytical method combining a size exclusion chromatography technique. (Size Exclusion Chromatography - SEC) with a multi-angle light scattering photometer (MALS) coupled to a viscometer (VIS) and a differential refractometer. This technique makes it possible to obtain the weight average molecular weight (Mw). This technique makes it possible to characterize the molecular weights of HAs accurately and reproducibly (Stepan Podzimek & al., Solution of Hyaluronic Acid and Comparison of SEC-MALLS-VIS Data with Off-line Capillary Viscometry Journal of Applied Polymer Science 2009).
    [0008] The coupling of size exclusion chromatography SEC to an MALS detector allows after injection of a solution of polymers into a chromatographic system, to separate these polymers by size in the chromatographic column, to measure this size by light scattering and to quantify them using a differential refractometer or a UV spectrometer. The hyaluronic acid or one of its salts is solubilized in an aqueous solution of 0.1M NaCl and then eluted on a column filled with polystyrene-divinylbenzene beads of calibrated porosity. Large polymer chains do not pass through all pores and are therefore eluted before small chains. - The MALS detector measures the scattering of incident light at different angles. These angles make it possible, by extrapolation, to measure RO which is 0-angle scattering. RO is directly proportional to the size of the molecule. The response Si of the differential refractometer is proportional to the total mass Ci of the polymer of degree of polymerization i according to the following equation (1): Si = K'.dn / dc.Ci where: Si is therefore the response of the differential refractometer K 'is a device-related constant, and C, is the total mass (weight) of polymer of degree of polymerization i (Ci = Ni x Mi), where N is the number of chains of molar mass M ,. The increment of refractive index dn / dc is furthermore a specific value of the polymer studied. This dn / dc ratio can be measured according to the following protocol exemplified with sodium hyaluronate. a / Apparatus and preparation of the solutions: The measurements are carried out on a refractometer such as the BricePhoenix model having as incident light source a helium-neon laser (X = 633nm). Different polymer concentrations to be studied are prepared independently by weighing (solution time = 24 hours). The respective refractive indices (dn) are then measured using the refractometer. b / Result The results are presented as a graph dn = f (concentration) (see Figure 1). A linear regression of the type Y = A + B * X is then determined. In the case of sodium hyaluronate, the values A and B determined are respectively A = -2.030 and B = 14927.911.
    [0009] The ratio dn / dc then corresponds to k x B where k represents the constant of the apparatus which is equal to 0.97.10-5 in the present example. For sodium hyaluronate, dn / dc is therefore evaluated at 0.97 × 10 -5 × 14927.911 = 0.145 ml / g.
    [0010] The following formula gives the relation between all the measured parameters: RO = where: RO is the diffusion angle RAYLEIG ratio 0, K is the constant of the apparatus, Ci represents the total mass of the polymer of degree of polymerization i [ calculated according to equation (1)] of the injected solution, and Mi represents the molar mass of the desired polymer chain. The weight average molecular weight Mw can then be calculated according to the formula: Mw = / CiMi / / Ci. All molecular weights are expressed in Daltons. Hyaluronic acid or its salt, which is the subject of the present invention, may be obtained according to one of the processes known to those skilled in the art, such as those described in document EP1987153. HA is mainly obtained industrially by bacterial fermentation: the hyaluronic acid filaments are synthesized by bacteria.
    [0011] Thus, in a particular embodiment of the invention, a high molecular weight native HA ranging generally from 1 MDa to 2 MDa is obtained by bacterial fermentation using a selected bacterial strain.
    [0012] The polymer obtained can then be separated from the bacterium. The solution is then purified and then hydrolysed by controlled acid hydrolysis until the desired molecular weight is obtained. In the case of the preparation of sodium hyaluronate, proceed to a neutralization step by adding NaOH. The salt of hyaluronic acid will preferably be sodium hyaluronate. In the context of the present invention, the low molecular weight sulphated polysaccharides may be chosen from sulphated fucans and sulphated ulvans with a molecular weight of between 5 and 25 kDa. Sulphated fucans are polysaccharides comprising sulfated L-fucose. These polysaccharides can be extracted in particular from brown algae, for example of the order Fucales or Laminariales.
    [0013] Sulphated ulvans are sulfated anionic polysaccharides comprising uronic acids (eg glucuronic acid, iduronic acid) and sulphates (eg 3-sulphate rhamnose, galactose, xylose, glucose) distributed in repeating units. The main reasons are: ulvanobiuronic 3-sulphate type A consisting of 3-sulphate α-rhamnose bound to PD-glucuronic acid by a 1-4-type linkage, and ulvanobiuronic 3-sulphate type B consisting of 3-sulfate α-Rhamnose bound to α-iduronic acid by a 1-> 4-type bond. Ulvans can be extracted in particular from green algae of the ulva type or enteromorph (Ulva sp., And Enteromorpha sp.).
    [0014] According to a particular embodiment, the sulphated fucan of low molecular weight is as described in WO 2010/086197. We can mention the commercial specialty Ascophyscient® Seaweed and sea extract of the seaweed Ascophyllum nodosum.
    [0015] According to another particular embodiment, the sulphated ulvan of low molecular weight is as described in WO 2013/150253.
    [0016] We can also mention the fraction QT40® marketed by Green Tech based on a particular oligosaccharide from the alga Ulva Lactuca: a sulphooligorhamnoglucuronane.
    [0017] According to one particular embodiment of the invention, the mass ratio of hyaluronic acid / polysaccharide is between 0.1 and 10. According to another particular embodiment of the invention, the mass ratio of hyaluronic acid / polysaccharide is between 0 and 10. , 5 and 5, and preferably between 0.5 and 2.
    [0018] The present invention further relates to a combination of hyaluronic acid or a salt thereof and low molecular weight sulphated polysaccharide according to the invention (i.e., of molecular weight between 5 and 25 kDa) for its use to promote the proliferation of fibroblasts.
    [0019] The present invention also relates to a cosmetic composition comprising, as an anti-aging active ingredient, a combination of a hyaluronic acid or a salt thereof and a sulphated polysaccharide with a molecular weight of between 5 and 25 kDa and further comprising at least one cosmetically acceptable excipient. Preferably, the cosmetically acceptable excipients are suitable for topical administration. Acceptable excipients in particular ensure good stability, texture and a pleasant touch. It may also be for example formulating agents or additives of known and conventional use in cosmetics: mention may be made of surfactants, dyes, preservatives, perfumes, film-forming agents, thickeners, etc.
    [0020] The anti-aging compositions may be in the forms which are usually known for topical administration to the skin, that is to say in particular creams, emulsions, lotions, serums, masks, wrinkle-filler, eye contours, ...
    [0021] The object of the present invention is the cosmetic use of the combination according to the present invention or of this cosmetic composition according to the invention to fight against the signs of skin aging. The cosmetic use of the combination according to the present invention or the cosmetic composition according to the invention is more particularly intended to restore the material to the skin, strengthen its firmness and visibly reduce marked wrinkles and deep furrows. The present invention also relates to a method for combating the signs of cutaneous aging comprising the administration, preferably topically, of an effective amount of a combination according to the invention or of a cosmetic composition according to the invention to a person in need. Another subject of the present invention relates to a dermatological composition intended to accelerate cutaneous repair in order to restore the integrity and the quality of the skin comprising as a dermatological or cosmetic active ingredient the combination of a hyaluronic acid or one of its salts and a sulfated polysaccharide whose molecular weight is between 5 and 25 kDa above mentioned and further comprising at least one dermatologically or cosmetically acceptable excipient.
    [0022] In a preferred embodiment of the invention, the composition is intended for topical application. The dermatologically (pharmaceutically) or cosmetically compatible excipients may be any excipient among those known to those skilled in the art in order to obtain a composition for topical application in the form of a milk, a cream or a cream. a balm, an oil, a lotion, a gel, a foaming gel, an ointment, a spray, etc. In a preferred embodiment, the composition will be in the form of a cream or ointment.
    [0023] In a particular embodiment, the dermatological and cosmetic compositions according to the invention comprise at least one other active ingredient. This other active ingredient may in particular be selected from the group comprising anti-aging agents, healing agents, soothing agents, antipruritic agents, antioxidants, anti-radical agents, anti-UV agents, stimulating the synthesis of dermal macromolecules or energy metabolism, moisturizers, depigmenting agents and antibacterials. , anti-fungal, anti-inflammatory, or anesthetic.
    [0024] According to one particular embodiment, the compositions according to the invention, which are preferably cosmetic, also comprise retinaldehyde. This complementary anti-aging active ingredient is a direct precursor of retinoic acid for a reactivating effect of immediate cellular metabolism. Retinaldehyde increases the expression of AH receptors, CD44 and induces AH synthesis. The composition according to the invention then comprises a combination of hyaluronic acid or a salt thereof, low molecular weight sulphated polysaccharide and retinaldehyde. According to another embodiment of the invention, the composition will further comprise a tocopherol derivative including the delta tocopheryl glucopyranoside: its powerful antioxidant effects protect the skin and maintain its luminosity. The composition according to the invention then comprises a combination of hyaluronic acid or a salt thereof, low molecular weight sulphated polysaccharide and delta tocopheryl glucopyranoside.
    [0025] According to another particular embodiment, the other active ingredient will be chosen from healing agents, soothing agents and mixtures thereof. Such an active ingredient will preferably be used in dermatological compositions.
    [0026] Finally, another object of the present invention is a combination of hyaluronic acid or a salt thereof and low molecular weight sulphated polysaccharide or a dermatological composition containing it according to the invention for its use as a medicament (more particularly dermatological), especially for the treatment and healing of skin lesions.
    [0027] The present invention also relates to the use of a combination of a hyaluronic acid or a salt thereof and a sulphated polysaccharide of molecular weight between 5 and 25 kDa for the preparation of a medicament (more particularly dermatological), especially for the treatment and healing of skin lesions.
    [0028] The present invention also relates to a method for treating and healing skin lesions comprising administering, preferably topically, an effective amount of a combination of a hyaluronic acid or a salt thereof and a sulfated weight polysaccharide. molecular compound of between 5 and 25 kDa or a dermatological composition containing it according to the invention to a person in need thereof.
    [0029] The dermatological and cosmetic compositions according to the invention are intended in particular for the care of injured skin: - following invasive procedures / treatments: surgical procedures (exeresis, shavings) with or without suture, cryotherapy, ablative laser, medium or strong peels, mesotherapy , curettage, - in post traumatic during cuts or superficial burns, - following superficial (non-invasive) acts requiring a healing product which accelerates the cutaneous recovery, usable in the long run (until complete repair of the skin), - following slight external damage: superficial abrasions, sunburn.
    [0030] The treatment of lesions of the skin and mucous membranes according to the invention may in particular include the treatment of cuts, sutures, abrasions, scratches, scratches, scars post-surgery or post-act of cosmetic dermatology, superficial burns , sunburns. The present invention further relates to the use of a cosmetic composition according to the invention for improving healing and skin repair. The invention will be better understood by reading the results below which illustrate it without limiting its scope.
    [0031] FIGURES FIG. 1 represents the refractive index dn as a function of the concentration c for sodium hyaluronate.
    [0032] Figure 2 shows the effect of AH according to the invention (HAF120) at 100 and 1000 ug / ml and Ascophyscient® at 10 and 100 ug / ml on the proliferation of fibroblasts. *: p <0.05 and **: p <0.01. Representative experience of 3 independent experiments.
    [0033] FIG. 3 represents the effect of AH according to the invention (HAF120) at 100 μg / ml, Ascophyscient® at 1.1 g / ml and their association on the proliferation of fibroblasts. *: p <0.05. Representative experience of 3 independent experiments. FIG. 4 represents the effect of AH according to the invention (HAF120) at 1000 μg / ml, Ascophyscient® at 1.1 g / ml and their association on the proliferation of fibroblasts. *: p <0.05 and **: p <0.01. Representative experience of 3 independent experiments. EXAMPLES PHARMACOLOGICAL ASSESSMENT of the Association of a Sodium Hyaluronate Fragment with a Weight Average Molecular Weight of between 60 and 120 kDa (HAF120) and a Low Molecular Weight Sulfate Fucan (5-25kDa) on Fibroblast Proliferation The technique used is that of the incorporation of a thymidine-like nucleotide, 5-bromo-2'-deoxyuridine (BrdU), into the DNA of S-phase cells at 37 ° C. This technique makes it possible to quantify the cells whose advance in the cell cycle is characteristic of a proliferative cell (S phase or DNA synthesis). FNH (normal human fibroblasts), isolated from cutaneous surgical waste, are usually cultured in DMEM (Dulbecco's Modified Eagle Medium) with 10% FCS (fetal calf serum). In our experimental conditions, the dilutions of the products to be tested are carried out in DMEM with 3% FCS.
    [0034] The cells are first deprived of FCS for 24 hours to stop the cell growth before incubating them in the presence of the molecules to be evaluated for 44 hours at 37 ° C. in a 5% CO 2 atmosphere. The incorporation of BrdU, proportional to the cell proliferation rate, is evaluated by a system of anti-BrdU antibodies (Roche Applied Science). The corresponding absorbance (OD) is measured at 450 nm. This data is therefore proportional to the cell proliferation rate. The evaluated assets are as follows: - Positive control: EGF (epidermal growth factor) at 10 ng / ml - Commercial specialty Ascophyscient® of Algae and Sea: 10 and 100 μg / ml (corresponding to 0.001 and 0) , 01% respectively) - sodium hyaluronate 60-120 kDa according to Example 1: 100 and 1000 μg / ml (corresponding to 0.01 and 0.1% respectively) - Association comprising respectively Ascophyscient® and sodium hyaluronate 60120 kDa to respective concentrations: 10 μg / ml + 100 μg / ml, 10 μg / ml + 1000 μg / ml. Analysis of the results: - in DO (proportional to the BrdU incorporation and therefore to the cell proliferation rate) - as a percentage of stimulation: treated OD E x 100] - 100 reference OD - in standard error of the mean: esm = deviation -type (Sd) / Vn Statistical analyzes: Statistical analyzes using the unpaired bilateral Student T test were performed on the raw OD values. This test then gives the values of the "p value" characterizing the significance of the results obtained for the different conditions. The degree of significance is established as follows: significant for p <0.05 (*) very significant for p <0.01 (**) highly significant for p <0.001 (***) not significant for p> 0.05 Results: Under these experimental conditions, Ascophyscient® induced the proliferation of fibroblasts in a very reproducible and statistically significant manner, especially at 100 μg / ml (FIG. 2). - Sodium hyaluronate alone has a moderate effect on the proliferation of fibroblasts (Figure 2). The combination of these two compounds induced the proliferation of fibroblasts in a synergistic manner (FIGS. 3 and 4). Conclusions: Under these experimental conditions, Ascophyscient® induced the proliferation of fibroblasts in a very reproducible and statistically significant way. The combination of Ascophyscient® with HAF120 induced the proliferation of fibroblasts in a synergistic manner. By inducing the proliferation of fibroblasts, Ascophyscient® and its combination with the 60-120 kDa fragment of sodium hyaluronate restores cellular metabolism and participates in dermal repair and the fight against aging.
    [0035] EXAMPLES OF COMPOSITION Example 1: Name Percentage Purified water QSP 100% Glycerin 6 Disodium EDTA 0.1 Phenoxyethanol 0.35 Acrylates / C10-30 Alkyl Acrylate Crosspolymer (Carbopol® Ultrez 21) 0.4 Polyacrylate-13 & Polyisobutene & Polysorbate 20 & Water (SepiplusTM 400) 1 Glyceryl Stearate & PEG-100 Stearate (SimulsolTM 165) 4 Cetyl Alcohol 1 Caprylic / Capric Caprylic / Capric Triglycerides (Myritol® 318) Dimethicone (DC 200) 4 Dicaprylyl Carbonate 4 Sodium Hyaluronate 60-120 kDa 0.5 Ascophyscient ® 0.3 Fragrance 0.1 Example 2: Name Percentage Purified water QSP 100% Glycerin 6 Disodium EDTA 0.1 Phenoxyethanol 0.35 Acrylates / C10-30 Alkyl Acrylate Crosspolymer (Carbopol® Ultrez 21) 0.4 Polyacrylate-13 & Polyisobutene & Polysorbate 20 & Water (SepiplusTM 400) 1 Glyceryl Stearate & PEG-100 Stearate (SimulsolTM 165) 4 Cetyl Alcohol 1 Caprylic / Capric Triglycerides (Myritol® 318) 10 Dimethicone (DC 200) 4 Isododecane 4 Hyaluronate d Sodium 60-120 kDa according to the invention 0.5 Ascophyscient® 0.3 Retinaldehyde 0.05 Perfume 0.1
    权利要求:
    Claims (9)
    [0001]
    REVENDICATIONS1. A combination comprising a hyaluronic acid or a salt thereof and a sulfated polysaccharide having a molecular weight of 5 to 25 kDa.
    [0002]
    2. Association according to claim 1, characterized in that the hyaluronic acid or a salt thereof has a weight average molecular weight between 50 and 750 kDa.
    [0003]
    3. Association according to claim 2, characterized in that said weight average molecular weight is between 60 and 120 kDa.
    [0004]
    4. Association according to one of claims 1 to 3, characterized in that the sulfated polysaccharide whose molecular weight is between 5 and 25 kDa is a sulphated fucan or sulfated ulvan.
    [0005]
    5. Association according to claim 1, characterized in that the mass ratio of hyaluronic acid / polysaccharide is between 0.1 and 10.
    [0006]
    6. Association according to one of claims 1 to 5 for its topical use for promoting the proliferation of fibroblasts.
    [0007]
    7. Topical use of an association according to one of claims 1 to 5 to combat the signs of skin aging.
    [0008]
    8. Association according to one of claims 1 to 5 for its topical use for treating skin lesions.
    [0009]
    9. Association according to one of claims 1 to 5 for its topical use for improving skin healing and recovery. 11. 12. 13. 14. 15. 16. Dermatological or cosmetic composition comprising as active ingredient a combination according to one of claims 1 to 5, with at least one dermatologically or cosmetically acceptable excipient. Composition according to Claim 10, characterized in that it further comprises another active ingredient. Composition according to Claim 11, characterized in that the other active ingredient is chosen from anti-aging, healing, soothing, anti-scouring and anti-radical agents. , anti-UV, stimulating the synthesis of dermal macromolecules or energy metabolism, moisturizing, depigmenting, antibacterial, antifungal, anti-inflammatory, anesthetic and their mixtures. Composition according to Claim 11, characterized in that the other active ingredient is retinaldehyde. Composition according to Claim 11, characterized in that the other active ingredient is delta tocopheryl glucopyranoside. Cosmetic use of the cosmetic composition according to any one of Claims 10 to 14 for combating the signs of cutaneous aging. Dermatological composition according to claim 10, for its use in the treatment of cuts, sutures, abrasions, scratches, scratches, scars post-surgery or post-act of cosmetic dermatology, superficial burns, sunburn.
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    同族专利:
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    KR20160145788A|2016-12-20|
    RU2683567C2|2019-03-29|
    RU2016146372A3|2018-10-03|
    WO2015166063A1|2015-11-05|
    MX2016014050A|2017-02-14|
    EP3137050B1|2020-03-04|
    CN106255490B|2019-10-01|
    RU2016146372A|2018-05-31|
    CA2946943A1|2015-11-05|
    EP3137050A1|2017-03-08|
    CN106255490A|2016-12-21|
    US9993417B2|2018-06-12|
    JP6625558B2|2019-12-25|
    BR112016024161B1|2021-03-02|
    AU2015254602B2|2019-10-24|
    FR3020570B1|2017-07-21|
    BR112016024161A2|2017-08-15|
    US20170049678A1|2017-02-23|
    JP2017514825A|2017-06-08|
    AU2015254602A1|2016-12-22|
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    优先权:
    申请号 | 申请日 | 专利标题
    FR1453973A|FR3020570B1|2014-04-30|2014-04-30|ASSOCIATION OF A HYALURONIC ACID AND A SULFATE POLYSACCHARIDE|FR1453973A| FR3020570B1|2014-04-30|2014-04-30|ASSOCIATION OF A HYALURONIC ACID AND A SULFATE POLYSACCHARIDE|
    AU2015254602A| AU2015254602B2|2014-04-30|2015-04-30|Combination of a hyaluronic acid and of a sulphated polysaccharide|
    MX2016014050A| MX2016014050A|2014-04-30|2015-04-30|Combination of a hyaluronic acid and of a sulphated polysaccharide.|
    US15/307,681| US9993417B2|2014-04-30|2015-04-30|Combination of a hyaluronic acid and of a sulphated polysaccharide|
    PCT/EP2015/059544| WO2015166063A1|2014-04-30|2015-04-30|Combination of a hyaluronic acid and of a sulphated polysaccharide|
    JP2016565157A| JP6625558B2|2014-04-30|2015-04-30|Combination of hyaluronic acid and sulfated polysaccharide|
    CN201580023077.3A| CN106255490B|2014-04-30|2015-04-30|The combination of hyaluronic acid and sulfated polysaccharides|
    BR112016024161-4A| BR112016024161B1|2014-04-30|2015-04-30|combination of hyaluronic acid and sulfated polysaccharide, dermatological or cosmetic composition, and use of the same|
    CA2946943A| CA2946943A1|2014-04-30|2015-04-30|Combination of a hyaluronic acid and of a sulphated polysaccharide|
    RU2016146372A| RU2683567C2|2014-04-30|2015-04-30|Combination of hyaluronic acid and sulphated polysaccharide|
    KR1020167032484A| KR20160145788A|2014-04-30|2015-04-30|Combination of a hyaluronic acid and of a sulphated polysaccharide|
    EP15718939.0A| EP3137050B1|2014-04-30|2015-04-30|Combination of a hyaluronic acid and of a sulphated polysaccharide|
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