WO2002047645A1 - Composition containing 7-hydroxy dhea and/or 7-keto dhea and at least a peeling agent - Google Patents

Composition containing 7-hydroxy dhea and/or 7-keto dhea and at least a peeling agent Download PDF

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Publication number
WO2002047645A1
WO2002047645A1 PCT/FR2001/003602 FR0103602W WO0247645A1 WO 2002047645 A1 WO2002047645 A1 WO 2002047645A1 FR 0103602 W FR0103602 W FR 0103602W WO 0247645 A1 WO0247645 A1 WO 0247645A1
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Prior art keywords
dhea
composition according
hydroxy
composition
chosen
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PCT/FR2001/003602
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French (fr)
Inventor
Nathalie Pineau
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L'oreal
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Priority to AU2002221985A priority Critical patent/AU2002221985A1/en
Publication of WO2002047645A1 publication Critical patent/WO2002047645A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/63—Steroids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/28—Rubbing or scrubbing compositions; Peeling or abrasive compositions; Containing exfoliants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists

Definitions

  • the present invention relates to a composition suitable for topical application to the skin or scalp, containing 7-hydroxy DHEA and / or 7-keto DHEA and at least one scaling agent, as well as the use of said composition, in particular for preventing or treating the signs of skin aging.
  • DHEA dehydroepiandrosterone
  • Exogenous DHEA administered topically or orally, is known for its ability to promote keratinization of the epidermis (JP-07 196 467) and to treat dry skin by increasing endogenous production and sebum secretion and by thus reinforcing the barrier effect of the skin (US-4,496,556).
  • JP-07 196 467 keratinization of the epidermis
  • US-4,496,556 The use of DHEA to remedy atrophy of the dermis by inhibiting the loss of collagen and connective tissue has also been described in US Pat. No. 5,843,932.
  • 7 ⁇ -hydroxy DHEA is, with 5-androstene 3 ⁇ , 17 ⁇ -diol, a major metabolite of DHEA, obtained by the action of 7 ⁇ -hydroxylase on DHEA.
  • minor metabolites of DHEA there may be mentioned 7 ⁇ -hydroxy DHEA, obtained by the action of 7 ⁇ -hydroxylase on DHEA and 7-keto DHEA, which is itself a metabolite of 7 ⁇ -hydroxy DHEA.
  • 7-hydroxy DHEA will be used to designate indifferently 7 ⁇ -hydroxy DHEA and 7 ⁇ -hydroxy DHEA.
  • the present invention therefore has. relates to a composition suitable for topical application to the skin or scalp, containing, in a physiologically acceptable medium: (a) at least one DHEA derivative chosen from 7-hydroxy DHEA and 7-keto DHEA, and ( b) at least one scaling agent.
  • the 7-hydroxy DHEA is preferably 7 -OH DHEA.
  • a process for the preparation of this compound is described in particular in patent applications FR-2 771 105 and WO 94/08588.
  • 7 ⁇ -OH DHEA is also suitable for use in the present invention.
  • the concentration of DHEA derivative in the composition according to the invention is advantageously between 0.0001% and 10% by weight, preferably between 0.001% and 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention contains, in association with the DHEA derivative, at least one desquamating agent.
  • the scaling agents capable of being used in the compositions according to the invention notably comprise ⁇ -hydroxy acids and ⁇ -hydroxy acids; ⁇ -keto acids and ⁇ -keto acids; retinoids; HMG-CoA reductase inhibitors, and sugar derivatives.
  • ⁇ -hydroxy acids which can be used in the present invention, mention may in particular be made of citric, lactic, glycolic, mandelic, malic and tartaric acids.
  • ⁇ -hydroxy acids are in particular salicylic acid and its derivatives described in applications FR-A-2 581 542, EP-875 495, WO 98/35973 and EP-756 866.
  • the salicylic acid derivative is a 5-acyl-salicylic acid such as n-octanoyl-5-salicylic acid, n-dodecanoyl-5-salicylic acid and n-decanoyl-5 acid -salicylic, in free or salified form, in particular in the form of salts obtained by salification with a mineral or organic base. It is particularly preferred to use n-octanoyl-5- acid. salicylic. This compound can be prepared as described in application FR-2,581,542 in the name of the Applicant.
  • a retinoid such as retinoic acid (all-trans or 13-cis) and its derivatives, retinaldehyde, retinol (vitamin A) and its esters such as retinyl palmitate, retinyl acetate and retinyl propionate, and mixtures thereof.
  • Retinol and retinyl palmitate are preferred for use in the present invention.
  • the desquamating agent can be chosen from HMG-CoA reductase inhibitors, as described in application EP-738 510.
  • the inhibitors of GMG-CoA-reductase can be, for example, the following compounds: mevastatin, lovastatin , pravastatin, simvastatin, fluvastatin, dalyastatin ,. and their derivatives and salts, especially their sodium salts.
  • the desquamating agent can be a sugar derivative, in particular a carbohydrate or carbohydrate derivative such as those described in application EP-853472, corresponding to formula (I):
  • ⁇ represents a chain composed of one to twenty carbohydrate units or carbohydrate derivatives, each comprising 3 to 6 carbon atoms, linked together, preferably by acetal bridges, each of these units possibly being substituted, for example by a halogen , by an amino function, an acid function, an ester function, a thioi, an alkoxy function, a thio-ether function, a thio-ester function, an amide function, a carbamate function and / or a urea function,
  • R represents an alkyl chain or an alkenyl chain, comprising from 4 to 24 carbon atoms, branched or linear, which can be interrupted by ether bridges, optionally carrying a hydroxyl function, a carboxylic acid function, an amino function, an ester function, an acyloxy function, an amide function, an ether function, a carbamate function and / or a urea function,
  • X represents a function connecting R and A, such as for example an amino function, ether, amide, ester, urea, carbamate, thioester, thioether or sulfonamide.
  • sugar derivatives there may be mentioned N-butanoyl-D-glucosamine, N-octanoyl-D-glucosamine, N-octyloxycarbonyl-N-methyl-D-glucamine, N-2-ethyl-hexyloxycarbonyl-N -methyl-D-glucamine, 6-0-octanoyl-D-glucose, 6'-0-dodecanoyl-D-maltose and 6'-0-octanoyl-D-maltose, the latter compound being particularly preferred.
  • the scaling agent can be used in the composition according to the invention in an amount representing from 0.01 to 10%, preferably from 0.1 to 5% and, better still, from 0.5 to 3% by weight of the total weight of the composition.
  • composition according to the invention is preferably suitable for topical application to the skin. It can be in all dosage forms normally used for this type of application, in particular in the form of an aqueous or oily solution, an oil-in-water or water-in-oil or multiple emulsion, a silicone emulsion, a microemulsion or nanoemulsion, an aqueous or oily gel or a liquid, pasty or solid anhydrous product.
  • This composition can be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, a foam. or a gel. It can optionally be applied to the skin in the form of an aerosol. It can also be in solid form, and for example in the form of a stick. It can be used as a care product and / or as a skin makeup product.
  • the composition of the invention may also contain the adjuvants usual in the cosmetic and dermatological fields, such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic active agents, preservatives, antioxidants, solvents, perfumes, fillers, filters, pigments, odor absorbers and coloring matter.
  • the amounts of these various adjuvants are those conventionally used in the fields under consideration, and for example from 0.01 to 20% of the total weight of the composition.
  • These adjuvants depending on their nature, can be introduced into the fatty phase or into the aqueous phase.
  • These adjuvants, as well as their concentrations must be such that they do not harm the advantageous properties of the DHEA derivatives, nor of the desquamating agents according to the invention.
  • the proportion of the fatty phase can range from 5 to 80% by weight, and preferably from 5 to 50% by weight relative to the total weight of the composition.
  • the fats, emulsifiers and coemulsifiers used in the composition in the form of an emulsion are chosen from those conventionally used in the field under consideration.
  • the emulsifier and the coemulsifier are preferably present in the composition in a proportion ranging from 0.3 to 30% by weight, and preferably from 0.5 to 20% by weight. weight relative to the total weight of the composition.
  • oils and in particular mineral oils such as mineral oils (petroleum jelly oil), oils of vegetable origin (avocado oil, soybean oil), oils of animal origin (lanolin) can be used.
  • synthetic oils perhydrosqualene
  • silicone oils cyclomethicone
  • fluorinated oils perfluoropolyethers.
  • Fatty alcohols such as cetyl alcohol, fatty acids, waxes and gums and in particular silicone gums can also be used as fats.
  • emulsifiers and coemulsifiers which can be used in the invention, there may be mentioned, for example, fatty acid esters of polyethylene glycol such as PEG-100 stearate, PEG-50 stearate and PEG-40 stearate; fatty acid esters of polyols such as glyceryl stearate, sorbitan tristearate and the oxyethylenated sorbitan stearates available under the tradenames Tween ® 20 or Tween ® 60, for example; and their mixtures.
  • polyethylene glycol such as PEG-100 stearate, PEG-50 stearate and PEG-40 stearate
  • fatty acid esters of polyols such as glyceryl stearate, sorbitan tristearate and the oxyethylenated sorbitan stearates available under the tradenames Tween ® 20 or Tween ® 60, for example; and their mixtures.
  • hydrophilic gelling agents mention may be made in particular of carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkyl acrylate copolymers, polyacrylamides, polysaccharides, natural gums and clays, and, as lipophilic gelling agents, cite modified clays such as bentones, metal salts of fatty acids and hydrophobic silica.
  • carboxyvinyl polymers carboxyvinyl polymers
  • acrylic copolymers such as acrylate / alkyl acrylate copolymers
  • polyacrylamides polysaccharides
  • natural gums and clays and, as lipophilic gelling agents, cite modified clays such as bentones, metal salts of fatty acids and hydrophobic silica.
  • composition according to the invention comprises an effective amount of DHEA derivative and an effective amount of scaling agent, sufficient to obtain the desired effect, in a physiologically acceptable environment.
  • composition according to the invention finds particular application in the prevention and treatment of the signs of skin aging.
  • the present invention therefore also relates to the cosmetic use of the composition mentioned above for preventing or treating the signs of skin aging.
  • N-octanoyl-5-salicylic acid 5.0% Vaseline 94.0%
  • N-octanoyl-5-salicylic acid 0.5% Vaseline 49.50%
  • compositions are applied once or twice a day to the skin for a period of one week to two months.

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Abstract

The invention concerns a composition for topical application on the skin or the scalp containing, in a physiologically acceptable medium: (a) at least a DHEA derivative selected among 7-hydroxy DHEA and 7-keto DHEA, and (b) at least a peeling agent. The peeling agent can in particular be selected among α-hydroxyacids and β-hydroxyacids, α-ketoacids and β-ketoacids, retinoids, HMG-CoA reductase inhibitors, and sugar derivatives. The invention also concerns cosmetic use of said composition for preventing or treating skin ageing symptoms.

Description

COMPOSITION RENFERMANT LA 7-HYDROXY DHEA ET/OU LA 7-CETO DHEA ET AU MOINS UN AGENT DESQUAMANTCOMPOSITION CONTAINING 7-HYDROXY DHEA AND / OR 7-CETO DHEA AND AT LEAST ONE DEQUAMANT
La présente invention se rapporte à une composition adaptée à une application topique sur la peau ou le cuir chevelu, renfermant la 7-hydroxy DHEA et/ou la 7-céto DHEA et au moins un agent desquamant, ainsi qu'à l'utilisation de ladite composition, notamment pour prévenir ou traiter les signes du vieillissement cutané.The present invention relates to a composition suitable for topical application to the skin or scalp, containing 7-hydroxy DHEA and / or 7-keto DHEA and at least one scaling agent, as well as the use of said composition, in particular for preventing or treating the signs of skin aging.
La DHEA, ou déhydroépiandrostérone, est un stéroïde naturel produit essentiellement par les glandes corticosurrénales. La DHEA exogène, administrée par voie topique ou .orale, est connue pour sa capacité à promouvoir la kératinisation de l'épiderme (JP-07 196 467) et à traiter les peaux sèches en augmentant la production endogène et la sécrétion de sébum et en renforçant ainsi l'effet barrière de la peau (US-4,496,556). Il a également été décrit dans le brevet US-5, 843,932 l'utilisation de la DHEA pour remédier à l'atrophie du derme par inhibition de la perte de collagène et de tissu conjonctif. Enfin, la Demanderesse a mis en évidence la capacité de la DHEA à lutter contre l'aspect papyracé de la peau (FR 00/00349), à moduler la pigmentation de la peau et des cheveux (FR 99/12773) et à lutter contre l'atrophie de l'épiderme (FR 00/06154). Ces propriétés de la DHEA en font un candidat de choix comme actif anti-âge.DHEA, or dehydroepiandrosterone, is a natural steroid produced primarily by the adrenal cortex. Exogenous DHEA, administered topically or orally, is known for its ability to promote keratinization of the epidermis (JP-07 196 467) and to treat dry skin by increasing endogenous production and sebum secretion and by thus reinforcing the barrier effect of the skin (US-4,496,556). The use of DHEA to remedy atrophy of the dermis by inhibiting the loss of collagen and connective tissue has also been described in US Pat. No. 5,843,932. Finally, the Applicant has demonstrated the ability of DHEA to fight against the papery appearance of the skin (FR 00/00349), to modulate the pigmentation of the skin and hair (FR 99/12773) and to fight against atrophy of the epidermis (FR 00/06154). These properties of DHEA make it a candidate of choice as an anti-aging active.
Parmi les métabolites de la DHEA, une attention particulière a été portée ces dernières années à la 7α-hydroxy DHEA. Il a en effet été démontré que ce métabolite, qui ne possède pas l'activité hormonale de la DHEA, permettait d'augmenter la prolifération des fibroblastes et la viabilité des kératinocytes humains et présentait des effets anti- radicalaires (WO 98/40074). Il a également été mis en évidence sur le rat (WO 00/28996) que la 7α-hydroxy DHEA augmentait l'épaisseur du derme et le contenu en élastine et collagène de la peau. Il a ainsi été suggéré d'utiliser ce métabolite de DHEA pour prévenir et/ou traiter les effets néfastes des UV sur la peau, lutter contre les rides et augmenter la fermeté et la tonicité de la peau.Among the metabolites of DHEA, particular attention has been paid in recent years to 7α-hydroxy DHEA. It has indeed been shown that this metabolite, which does not have the hormonal activity of DHEA, makes it possible to increase the proliferation of fibroblasts and the viability of human keratinocytes and has anti-radical effects (WO 98/40074). It has also been demonstrated in rats (WO 00/28996) that 7α-hydroxy DHEA increases the thickness of the dermis and the elastin and collagen content of the skin. It has thus been suggested to use this metabolite of DHEA to prevent and / or treat the harmful effects of UV on the skin, fight against wrinkles and increase the firmness and tone of the skin.
La 7α-hydroxy DHEA est, avec le 5-androstène 3β,17β-diol, un métabolite majeur de la DHEA, obtenu par action de la 7α-hydroxylase sur la DHEA. Parmi les métabolites mineurs de la DHEA, on peut citer la 7β-hydroxy DHEA, obtenue par action de la 7β- hydroxylase sur la DHEA et la 7-céto DHEA, qui est elle-même un métabolite de la 7β- hydroxy DHEA.7α-hydroxy DHEA is, with 5-androstene 3β, 17β-diol, a major metabolite of DHEA, obtained by the action of 7α-hydroxylase on DHEA. Among the minor metabolites of DHEA, there may be mentioned 7β-hydroxy DHEA, obtained by the action of 7β-hydroxylase on DHEA and 7-keto DHEA, which is itself a metabolite of 7β-hydroxy DHEA.
Dans la suite de cette description, l'expression "7-hydroxy DHEA" sera utilisée pour désigner indifféremment la 7α-hydroxy DHEA et la 7β-hydroxy DHEA.In the remainder of this description, the expression "7-hydroxy DHEA" will be used to designate indifferently 7α-hydroxy DHEA and 7β-hydroxy DHEA.
Il est maintenant apparu à la Demanderesse que l'association de la 7-hydroxy DHEA et/ou de la 7-céto DHEA avec un agent desquamant permettait de prévenir ou traiter plus efficacement les signes de vieillissement cutané.It has now appeared to the Applicant that the combination of 7-hydroxy DHEA and / or 7-keto DHEA with a desquamating agent makes it possible to more effectively prevent or treat the signs of skin aging.
La présente invention a donc. pour objet une composition adaptée à une application topique sur la peau ou le cuir chevelu, renfermant, dans un milieu physiologiquement acceptable : (a) au moins un dérivé de DHEA choisi parmi la 7-hydroxy DHEA et la 7- céto DHEA, et (b) au moins un agent desquamant.The present invention therefore has. relates to a composition suitable for topical application to the skin or scalp, containing, in a physiologically acceptable medium: (a) at least one DHEA derivative chosen from 7-hydroxy DHEA and 7-keto DHEA, and ( b) at least one scaling agent.
La 7-hydroxy DHEA est de préférence la 7 -OH DHEA. Un procédé de préparation de ce composé est notamment décrit dans les demandes de brevet FR-2 771 105 et WO 94/08588. Toutefois, la 7β-OH DHEA convient également à une utilisation dans la présente invention.The 7-hydroxy DHEA is preferably 7 -OH DHEA. A process for the preparation of this compound is described in particular in patent applications FR-2 771 105 and WO 94/08588. However, 7β-OH DHEA is also suitable for use in the present invention.
La concentration en dérivé de DHEA dans la composition selon l'invention est avantageusement comprise entre 0,0001% et 10% en poids, de préférence entre 0,001% et 5% en poids, par rapport au poids total de la composition.The concentration of DHEA derivative in the composition according to the invention is advantageously between 0.0001% and 10% by weight, preferably between 0.001% and 5% by weight, relative to the total weight of the composition.
La composition selon la présente invention renferme, en association avec le dérivé de DHEA, au moins un agent desquamant.The composition according to the present invention contains, in association with the DHEA derivative, at least one desquamating agent.
Les agents desquamants susceptibles d'être utilisés dans les compositions selon l'invention comprennent notamment les α-hydroxyacides et les β-hydroxyacides ; les α-cétoacides et les β-cétoacides ; les rétinoïdes ; les inhibiteurs d'HMG-CoA reductase, et les dérivés de sucre.The scaling agents capable of being used in the compositions according to the invention notably comprise α-hydroxy acids and β-hydroxy acids; α-keto acids and β-keto acids; retinoids; HMG-CoA reductase inhibitors, and sugar derivatives.
Comme α-hydroxyacides utilisables dans la présente invention, on peut citer en particulier les acides citrique, lactique, glycolique, mandelique, malique et tartrique. Des exemples de β-hydroxyacides sont notamment l'acide salicylique et ses dérivés décrits dans les demandes FR-A-2 581 542, EP-875 495, WO 98/35973 et EP-756 866. Selon une forme d'exécution préférée de l'invention, le dérivé d'acide salicylique est un acide 5-acyl-salicylique tel que l'acide n-octanoyl-5-salicylique, l'acide n- dodécanoyl-5-salicylique et l'acide n-décanoyl-5-salicylique, sous forme libre ou salifiée, en particulier sous forme de sels obtenus par salification avec une base minérale ou organique. On préfère en particulier utiliser l'acide n-octanoyl-5- salicylique. Ce composé peut être préparé comme décrit dans la demande FR-2 581 542 au nom de la Demanderesse.As α-hydroxy acids which can be used in the present invention, mention may in particular be made of citric, lactic, glycolic, mandelic, malic and tartaric acids. Examples of β-hydroxy acids are in particular salicylic acid and its derivatives described in applications FR-A-2 581 542, EP-875 495, WO 98/35973 and EP-756 866. According to a preferred embodiment of the invention, the salicylic acid derivative is a 5-acyl-salicylic acid such as n-octanoyl-5-salicylic acid, n-dodecanoyl-5-salicylic acid and n-decanoyl-5 acid -salicylic, in free or salified form, in particular in the form of salts obtained by salification with a mineral or organic base. It is particularly preferred to use n-octanoyl-5- acid. salicylic. This compound can be prepared as described in application FR-2,581,542 in the name of the Applicant.
Comme agent desquamant, on peut en variante utiliser un rétinoïde tel que l'acide rétinoïque (all-trans ou 13-cis) et ses dérivés, le rétinaldéhyde, le rétinol (vitamine A) et ses esters tels que le palmitate de rétinyle, l'acétate de rétinyle et le propionate de rétinyle, ainsi que leurs mélanges. Le rétinol et le palmitate de rétinyle sont préférés pour une utilisation dans la présente invention.As a desquamating agent, it is alternatively possible to use a retinoid such as retinoic acid (all-trans or 13-cis) and its derivatives, retinaldehyde, retinol (vitamin A) and its esters such as retinyl palmitate, retinyl acetate and retinyl propionate, and mixtures thereof. Retinol and retinyl palmitate are preferred for use in the present invention.
Selon une autre possibilité, l'agent desquamant peut être choisi parmi les inhibiteurs d'HMG-CoA reductase, comme décrit dans la demande EP-738 510. Les inhibiteurs dΗMG-CoA-réductase peuvent être par exemple les composés suivants : mévastatine, lovastatine, pravastatine, simvastatine, fluvastatine, dalyastatine,. et leurs dérivés et sels, notamment leurs sels de sodium.According to another possibility, the desquamating agent can be chosen from HMG-CoA reductase inhibitors, as described in application EP-738 510. The inhibitors of GMG-CoA-reductase can be, for example, the following compounds: mevastatin, lovastatin , pravastatin, simvastatin, fluvastatin, dalyastatin ,. and their derivatives and salts, especially their sodium salts.
Selon encore une autre possibilité, l'agent desquamant peut être un dérivé de sucre, en particulier un carbohydrate ou dérivé de carbohydrate tels que ceux décrits dans la demande EP-853472, répondant à la formule (I) :According to yet another possibility, the desquamating agent can be a sugar derivative, in particular a carbohydrate or carbohydrate derivative such as those described in application EP-853472, corresponding to formula (I):
R-X-A (l)R-X-A (l)
dans laquelle :in which :
 représente une chaîne composée de une à vingt unités carbohydrate ou dérivé de carbohydrate, comprenant chacune 3 à 6 atomes de carbone, reliées entre elles, de préférence par des ponts acétals, chacune de ces unités pouvant être éventuellement substituée, par exemple par un halogène, par une fonction aminé, une fonction acide, une fonction ester, un thioi, une fonction alcoxy, une fonction thio-éther, une fonction thio-ester, une fonction amide, une fonction carbamate et/ou une fonction urée, represents a chain composed of one to twenty carbohydrate units or carbohydrate derivatives, each comprising 3 to 6 carbon atoms, linked together, preferably by acetal bridges, each of these units possibly being substituted, for example by a halogen , by an amino function, an acid function, an ester function, a thioi, an alkoxy function, a thio-ether function, a thio-ester function, an amide function, a carbamate function and / or a urea function,
R représente une chaîne alcoyle ou une chaîne alcényle, comprenant de 4 à 24 atomes de carbone, ramifiée ou linéaire, pouvant être interrompue par des ponts éthers, portant éventuellement une fonction hydroxyle, une fonction acide carboxylique, une fonction aminé, une fonction ester, une fonction acyloxy, une fonction amide, une fonction éther, une fonction carbamate et/ou une fonction urée,R represents an alkyl chain or an alkenyl chain, comprising from 4 to 24 carbon atoms, branched or linear, which can be interrupted by ether bridges, optionally carrying a hydroxyl function, a carboxylic acid function, an amino function, an ester function, an acyloxy function, an amide function, an ether function, a carbamate function and / or a urea function,
X représente une fonction reliant R et A, comme par exemple une fonction aminé, éther, amide, ester, urée, carbamate, thioester, thioéther ou sulfonamide.X represents a function connecting R and A, such as for example an amino function, ether, amide, ester, urea, carbamate, thioester, thioether or sulfonamide.
Ces composés sont décrits, ainsi que leur procédé de préparation, dans la demande EP-0 853472.These compounds are described, as well as their preparation process, in application EP-0 853472.
Comme dérivés de sucre préférés, on peut citer le N-butanoyl-D-glucosamine, le N- octanoyl-D-glucosamine, le N-octyloxycarbonyl-N-méthyl-D-glucamine, le N-2-éthyl- hexyloxycarbonyl-N-méthyl-D-glucamine, le 6-0-octanoyl-D-glucose, le 6'-0- dodécanoyl-D-maltose et le 6'-0-octanoyl-D-maltose, ce dernier composé étant particulièrement préféré.As preferred sugar derivatives, there may be mentioned N-butanoyl-D-glucosamine, N-octanoyl-D-glucosamine, N-octyloxycarbonyl-N-methyl-D-glucamine, N-2-ethyl-hexyloxycarbonyl-N -methyl-D-glucamine, 6-0-octanoyl-D-glucose, 6'-0-dodecanoyl-D-maltose and 6'-0-octanoyl-D-maltose, the latter compound being particularly preferred.
A titre d'exemple, l'agent desquamant peut être utilisé dans la composition selon l'invention en une quantité représentant de 0,01 à 10 %, de préférence de 0,1 à 5 % et, mieux, de 0,5 à 3 % en poids du poids total de la composition.By way of example, the scaling agent can be used in the composition according to the invention in an amount representing from 0.01 to 10%, preferably from 0.1 to 5% and, better still, from 0.5 to 3% by weight of the total weight of the composition.
La composition selon l'invention est de préférence adaptée à une application topique sur la peau. Elle peut se présenter sous toutes les formes galéniques normalement utilisées pour ce type d'application, notamment sous forme d'une solution aqueuse ou huileuse, d'une émulsion huile-dans-eau ou eau-dans-huile ou multiple, d'une émulsion siliconée, d'une microémulsion ou nanoémulsion, d'un gel aqueux ou huileux ou d'un produit anhydre liquide, pâteux ou solide.The composition according to the invention is preferably suitable for topical application to the skin. It can be in all dosage forms normally used for this type of application, in particular in the form of an aqueous or oily solution, an oil-in-water or water-in-oil or multiple emulsion, a silicone emulsion, a microemulsion or nanoemulsion, an aqueous or oily gel or a liquid, pasty or solid anhydrous product.
Cette composition peut être plus ou moins fluide et avoir l'aspect d'une crème blanche ou colorée, d'une pommade, d'un lait, d'une lotion, d'un sérum, d'une pâte, d'une mousse ou d'un gel. Elle peut éventuellement être appliquée sur la peau sous forme d'aérosol. Elle peut également se présenter sous forme solide, et par exemple sous forme de stick. Elle peut être utilisée comme produit de soin et/ou comme produit de maquillage de la peau.This composition can be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, a foam. or a gel. It can optionally be applied to the skin in the form of an aerosol. It can also be in solid form, and for example in the form of a stick. It can be used as a care product and / or as a skin makeup product.
De façon connue, la composition de l'invention peut contenir également les adjuvants habituels dans les domaines cosmétique et dermatologique, tels que les gélifiants hydrophiles ou lipophiles, les actifs hydrophiles ou lipophiles, les conservateurs, les antioxydants, les solvants, les parfums, les charges, les filtres, les pigments, les absorbeurs d'odeur et les matières colorantes. Les quantités de ces différents adjuvants sont celles classiquement utilisées dans les domaines considérés, et par exemple de 0,01 à 20 % du poids total de la composition. Ces adjuvants, selon leur nature, peuvent être introduits dans la phase grasse ou dans la phase aqueuse. Ces adjuvants, ainsi que leurs concentrations, doivent être tels qu'ils ne nuisent pas aux propriétés avantageuses des dérivés de DHEA, ni des agents desquamants selon l'invention.In a known manner, the composition of the invention may also contain the adjuvants usual in the cosmetic and dermatological fields, such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic active agents, preservatives, antioxidants, solvents, perfumes, fillers, filters, pigments, odor absorbers and coloring matter. The amounts of these various adjuvants are those conventionally used in the fields under consideration, and for example from 0.01 to 20% of the total weight of the composition. These adjuvants, depending on their nature, can be introduced into the fatty phase or into the aqueous phase. These adjuvants, as well as their concentrations, must be such that they do not harm the advantageous properties of the DHEA derivatives, nor of the desquamating agents according to the invention.
Lorsque la composition selon l'invention est une émulsion, la proportion de la phase grasse peut aller de 5 à 80 % en poids, et de préférence de 5 à 50 % en poids par rapport au poids total de la composition. Les matières grasses, les émulsionnants et les coémulsionnants utilisés dans la composition sous forme d'émulsion sont choisis parmi ceux classiquement utilisés dans le domaine considéré. L'émulsionnant et le coémulsionnant sont de préférence présents, dans la composition, en une proportion allant de 0,3 à 30 % en poids, et de préférence de 0,5 à 20 % en. poids par rapport au poids total de la composition.When the composition according to the invention is an emulsion, the proportion of the fatty phase can range from 5 to 80% by weight, and preferably from 5 to 50% by weight relative to the total weight of the composition. The fats, emulsifiers and coemulsifiers used in the composition in the form of an emulsion are chosen from those conventionally used in the field under consideration. The emulsifier and the coemulsifier are preferably present in the composition in a proportion ranging from 0.3 to 30% by weight, and preferably from 0.5 to 20% by weight. weight relative to the total weight of the composition.
Comme matières grasses utilisables dans l'invention, on peut utiliser les huiles et notamment les huiles minérales (huile de vaseline), les huiles d'origine végétale (huile d'avocat, huile de soja), les huiles d'origine animale (lanoline), les huiles de synthèse (perhydrosqualène), les huiles siliconées (cyclométhicone) et les huiles fluorées (perfluoropolyéthers). On peut aussi utiliser comme matières grasses des alcools gras tels que l'alcool cétylique, des acides gras, des cires et des gommes et en particulier les gommes de silicone.As fats which can be used in the invention, oils and in particular mineral oils (petroleum jelly oil), oils of vegetable origin (avocado oil, soybean oil), oils of animal origin (lanolin) can be used. ), synthetic oils (perhydrosqualene), silicone oils (cyclomethicone) and fluorinated oils (perfluoropolyethers). Fatty alcohols such as cetyl alcohol, fatty acids, waxes and gums and in particular silicone gums can also be used as fats.
Comme émulsionnants et coémulsionnants utilisables dans l'invention, on peut citer par exemple les esters d'acide gras et de polyéthylène glycol tels que le stéarate de PEG-100, le stéarate de PEG-50 et le stéarate de PEG-40 ; les esters d'acide gras et de polyol tels que le stéarate de glycéryle, le tristearate de sorbitane et les stéarates de sorbitane oxyéthylénés disponibles sous les dénominations commerciales Tween® 20 ou Tween® 60, par exemple ; et leurs mélanges.As emulsifiers and coemulsifiers which can be used in the invention, there may be mentioned, for example, fatty acid esters of polyethylene glycol such as PEG-100 stearate, PEG-50 stearate and PEG-40 stearate; fatty acid esters of polyols such as glyceryl stearate, sorbitan tristearate and the oxyethylenated sorbitan stearates available under the tradenames Tween ® 20 or Tween ® 60, for example; and their mixtures.
Comme gélifiants hydrophiles, on peut citer en particulier les polymères carboxyvinyliques (carbomer), les copolymères acryliques tels que les copolymères d'acrylates/alkylacrylates, les polyacrylamides, les polysaccharides, les gommes naturelles et les argiles, et, comme gélifiants lipophiles, on peut citer les argiles modifiées comme les bentones, les sels métalliques d'acides gras et la silice hydrophobe..As hydrophilic gelling agents, mention may be made in particular of carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkyl acrylate copolymers, polyacrylamides, polysaccharides, natural gums and clays, and, as lipophilic gelling agents, cite modified clays such as bentones, metal salts of fatty acids and hydrophobic silica.
La composition selon l'invention comprend une quantité efficace de dérivé de DHEA et une quantité efficace d'agent desquamant, suffisante pour obtenir l'effet recherché, dans un milieu physiologiquement acceptable.The composition according to the invention comprises an effective amount of DHEA derivative and an effective amount of scaling agent, sufficient to obtain the desired effect, in a physiologically acceptable environment.
La composition selon l'invention trouve notamment une application dans la prévention et le traitement des signes du vieillissement cutané.The composition according to the invention finds particular application in the prevention and treatment of the signs of skin aging.
La présente invention concerne donc également l'utilisation cosmétique de la composition mentionnée ci-dessus pour prévenir ou traiter les signes du vieillissement cutané.The present invention therefore also relates to the cosmetic use of the composition mentioned above for preventing or treating the signs of skin aging.
L'invention sera maintenant illustrée par l'exemple non limitatif suivant. Dans cet exemple, les quantités sont indiquées en pourcentage pondéral.The invention will now be illustrated by the following nonlimiting example. In this example, the quantities are indicated in percentage by weight.
Exemple 1 : Crème desquamanteExample 1: desquamating cream
7α-OH DHEA 1 ,0 %7α-OH DHEA 1.0%
Acide n-octanoyl-5-salicylique 5,0 % Vaseline 94,0 %N-octanoyl-5-salicylic acid 5.0% Vaseline 94.0%
Exemple 2 : Crème desquamanteExample 2: desquamating cream
7α-OH DHEA 0,1 %7α-OH DHEA 0.1%
Acide n-octanoyl-5-salicylique 1 ,0 %1.0% n-octanoyl-5-salicylic acid
Vaseline 49,4 %Vaseline 49.4%
Ether de diméthylpolytetrahydrofurane 49,5 %Dimethylpolytetrahydrofuran ether 49.5%
Exemple 3 : Crème desquamanteEXAMPLE 3 Flaking Cream
7α-OH DHEA 0,5 %7α-OH DHEA 0.5%
Acide n-octanoyl-5-salicylique 0,5 % Vaseline 49,50 %N-octanoyl-5-salicylic acid 0.5% Vaseline 49.50%
Perhydrosqualène 49,50 %Perhydrosqualene 49.50%
Ces compositions sont appliquées une à deux fois par jour sur la peau pendant une période de une semaine à deux mois. These compositions are applied once or twice a day to the skin for a period of one week to two months.

Claims

REVENDICATIONS
1. Composition adaptée à une application topique sur la peau, renfermant, dans un milieu physiologiquement acceptable : (a) au moins un dérivé de DHEA choisi parmi la 7-hydroxy DHEA et la 7-céto DHEA, et (b) au moins un agent desquamant.1. Composition suitable for topical application to the skin, containing, in a physiologically acceptable medium: (a) at least one DHEA derivative chosen from 7-hydroxy DHEA and 7-keto DHEA, and (b) at least one flaking agent.
2. Composition selon la revendication 1 , caractérisée en ce que la 7-hydroxy DHEA est la 7α-OH DHEA.2. Composition according to claim 1, characterized in that the 7-hydroxy DHEA is 7α-OH DHEA.
3. Composition selon la revendication 1 , caractérisée en ce que la 7-hydroxy DHEA est la 7β-OH DHEA.3. Composition according to claim 1, characterized in that the 7-hydroxy DHEA is 7β-OH DHEA.
4. Composition selon l'une quelconque des revendications 1 à 3, caractérisée en ce que ledit agent desquamant est choisi parmi : les α-hydroxyacides et les β- hydroxyacides ; les α-cétoacides et les β-cétoacides ; les rétinoïdes ; les inhibiteurs d'HMG-CoA reductase ; et les dérivés de sucre.4. Composition according to any one of claims 1 to 3, characterized in that said desquamating agent is chosen from: α-hydroxy acids and β-hydroxy acids; α-keto acids and β-keto acids; retinoids; HMG-CoA reductase inhibitors; and sugar derivatives.
5. Composition selon la revendication 4, caractérisée en ce que ledit α-hydroxyacide est choisi parmi les acides citrique, lactique, glycolique, mandelique, malique et tartrique.5. Composition according to claim 4, characterized in that said α-hydroxy acid is chosen from citric, lactic, glycolic, mandelic, malic and tartaric acids.
6. Composition selon la revendication 4, caractérisée en ce que ledit β-hydroxyacide est choisi parmi l'acide salicylique et ses dérivés.6. Composition according to claim 4, characterized in that said β-hydroxy acid is chosen from salicylic acid and its derivatives.
7. Composition selon la revendication 6, caractérisée en ce que ledit dérivé d'acide salicylique est choisi parmi l'acide n-octanoyl-5-salicylique, l'acide n-dodécanoyl-5- salicylique et l'acide n-décanoyl-5-salicylique, sous forme libre ou salifiée.7. Composition according to claim 6, characterized in that said salicylic acid derivative is chosen from n-octanoyl-5-salicylic acid, n-dodecanoyl-5-salicylic acid and n-decanoyl- acid 5-salicylic, in free or salified form.
8. Composition selon la revendication 4, caractérisée en ce que ledit rétinoïde est choisi parmi : rétinoïde tel que l'acide rétinoïque (all-trans ou 13-cis) et ses dérivés, le rétinaldéhyde, le rétinol (vitamine A) et ses esters tels que le palmitate de rétinyle, l'acétate de rétinyle et le propionate de rétinyle.8. Composition according to claim 4, characterized in that said retinoid is chosen from: retinoid such as retinoic acid (all-trans or 13-cis) and its derivatives, retinaldehyde, retinol (vitamin A) and its esters such as retinyl palmitate, retinyl acetate and retinyl propionate.
9. Composition selon la revendication 4, caractérisée en ce que ledit inhibiteur d'HMG- CoA reductase est choisi parmi les composés suivants : mévastatine, lovastatine, pravastatine, simvastatine, fluvastatine, dalvastatine, et leurs dérivés et sels. 9. Composition according to claim 4, characterized in that said HMG-CoA reductase inhibitor is chosen from the following compounds: mevastatin, lovastatin, pravastatin, simvastatin, fluvastatin, dalvastatin, and their derivatives and salts.
10. Composition selon la revendication 4, caractérisée en ce que ledit dérivé de sucre est choisi parmi : le N-butanoyl-D-glucosamine, le N-octanoyl-D-glucosamine, le N- octyloxycarbonyl-N-méthyl-D-glucamine, le N-2-éthyl-hexyloxycarbonyl-N-méthyl-D- glucamine, le 6-0-octanoyl-D-glucose, le 6'-0-dodécanoyl-D-maltose et le 6'-0- octanoyl-D-maltose.10. Composition according to claim 4, characterized in that said sugar derivative is chosen from: N-butanoyl-D-glucosamine, N-octanoyl-D-glucosamine, N-octyloxycarbonyl-N-methyl-D-glucamine , N-2-ethyl-hexyloxycarbonyl-N-methyl-D-glucamine, 6-0-octanoyl-D-glucose, 6'-0-dodecanoyl-D-maltose and 6'-0-octanoyl-D -maltose.
11. Composition selon la revendication 10, caractérisée en ce que ledit dérivé de sucre est le 6'-0-octanoyl-D-maltose.11. Composition according to claim 10, characterized in that said sugar derivative is 6'-0-octanoyl-D-maltose.
12. Composition selon l'une quelconque des revendications 1 à 11 , caractérisée en ce qu'elle renferme de 0,0001 à 10% en poids de dérivé de DHEA, par rapport au poids total de la composition.12. Composition according to any one of claims 1 to 11, characterized in that it contains from 0.0001 to 10% by weight of DHEA derivative, relative to the total weight of the composition.
13. Composition selon la revendication 12, caractérisée en ce qu'elle renferme de 0,001 à 5% en poids de dérivé de DHEA, par rapport au poids total de la composition.13. Composition according to claim 12, characterized in that it contains from 0.001 to 5% by weight of DHEA derivative, relative to the total weight of the composition.
14. Composition selon l'une quelconque des revendications 1 à 13, caractérisée en ce qu'elle comprend de 0,1% à 5% en poids d'agent desquamant, par rapport au poids total de la composition.14. Composition according to any one of claims 1 to 13, characterized in that it comprises from 0.1% to 5% by weight of scaling agent, relative to the total weight of the composition.
15. Composition selon la revendication 14, caractérisée en ce qu'elle comprend de 0,5% à 3% en poids d'agent desquamant, par rapport au poids total de la composition.15. Composition according to claim 14, characterized in that it comprises from 0.5% to 3% by weight of scaling agent, relative to the total weight of the composition.
16. Utilisation cosmétique de la composition selon l'une quelconque des revendications 1 à 15 pour prévenir ou traiter les signes du vieillissement cutané. 16. Cosmetic use of the composition according to any one of claims 1 to 15 for preventing or treating the signs of skin aging.
PCT/FR2001/003602 2000-12-15 2001-11-16 Composition containing 7-hydroxy dhea and/or 7-keto dhea and at least a peeling agent WO2002047645A1 (en)

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