WO2001026619A2 - Composition, in particular cosmetic, containing dihydroepiandosterone (dhea) and a desquamative agent - Google Patents

Composition, in particular cosmetic, containing dihydroepiandosterone (dhea) and a desquamative agent Download PDF

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Publication number
WO2001026619A2
WO2001026619A2 PCT/FR2000/002682 FR0002682W WO0126619A2 WO 2001026619 A2 WO2001026619 A2 WO 2001026619A2 FR 0002682 W FR0002682 W FR 0002682W WO 0126619 A2 WO0126619 A2 WO 0126619A2
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function
composition according
composition
skin
chosen
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PCT/FR2000/002682
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French (fr)
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WO2001026619A3 (en
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Olivier De Lacharriere
Stéphanie Nouveau
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L'oreal
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Priority claimed from FR9912773A external-priority patent/FR2799645B1/en
Application filed by L'oreal filed Critical L'oreal
Priority to AU2000276682A priority Critical patent/AU2000276682A1/en
Publication of WO2001026619A2 publication Critical patent/WO2001026619A2/en
Publication of WO2001026619A3 publication Critical patent/WO2001026619A3/en

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    • 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
    • A61Q19/007—Preparations for dry skin
    • 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
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • 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
    • A61K8/37—Esters of carboxylic 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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
    • 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
    • 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
    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening 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
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists

Definitions

  • composition in particular cosmetic, containing DHEA and a scaling agent
  • the present invention relates to a composition containing DHEA, in combination with at least one scaling agent.
  • DHEA dehydroepiandrosterone
  • Exogenous DHEA administered topically or orally, is particularly 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). It has also been described in US Pat. No. 5,843,932 the use of DHEA for remedying atrophy of the dermis by inhibiting the loss of collagen and connective tissue.
  • the subject of the present invention is therefore a new composition
  • a composition comprising, in a physiologically acceptable medium, (a) DHEA, and (b) at least one desquamating agent chosen from retinoids, acyl derivatives of salicylic acid, inhibitors of HMG-CoA reductase and sugar derivatives.
  • DHEA has the following formula (I):
  • the DHEA which can be used according to the invention is for example available from the company AKZO NOBEL.
  • the concentration of DHEA in the composition according to the invention is advantageously between 0.001% and 20% by weight, preferably between 0.01 and 10% by weight, more preferably between 0.1 and 3% by weight, relative to the total weight of the composition.
  • retinoids such as retinoic acid (all-trans or 13-cis) and its derivatives, retinaldehyde, retinol (vitamin A) and its esters such as retinol palmitate, acetate can be used. retinol and retinol propionate, and mixtures thereof.
  • the desquamating agent can be an acylated derivative of salicylic acid, in particular a 5-acyl-saiicylic acid such as n-octanoyl-5-saiicylic acid, n-dodecanoyl-5-salicylic acid and n-decanoyl-5-salicylic acid, 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-salicylic acid.
  • This compound can be prepared as described in application FR-2,581,542 in the name of the Applicant.
  • the desquamating agent can be chosen from HMG-CoA reductase inhibitors.
  • HMG-CoA-reductase inhibitors can be, for example, the following compounds: mevastatin, lovastatin, pravastatin, simvastatin, fluvastatin, dalvastatin, and their derivatives and salts, in particular their sodium salts.
  • the desquamating agent can be a sugar derivative, in particular a carbohydrate or carbohydrate derivative corresponding to formula (I),
  • A 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 thiol, 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 linking R and A, such as for example an amine, ether, amide, ester, urea, carbamate, thioester, thioether or sulfonamide function.
  • sugar derivatives there may be mentioned N-butanoyI-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 0.1 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 can be in all dosage forms normally used for topical application to the skin, in particular in the form of an oily solution, of an oil-in-water or water-in-oil or multiple emulsion.
  • 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, into the aqueous phase, into the lipid vesicles and / or into the nanoparticles.
  • These adjuvants, as well as their concentrations must be such that they do not harm the advantageous properties of the combination of active 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 co-emulsifier 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 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 (oil) can be used. avocado, soybean oil), oils of animal origin (lanolin), 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.
  • emulsifiers and coemulsifiers which can be used in the invention, mention may, for example, be made of fatty acid and polyethylene glycol esters such as PEG-100 stearate, PEG-50 stearate and PEG-40 stearate; polyol fatty acid esters such as glyceryl stearate, sorbitan tristearate and oxyethylenated sorbitan stearates available under the trade names Tween® 20 or Tween® 60, for example; and their mixtures.
  • fatty acid and polyethylene glycol esters such as PEG-100 stearate, PEG-50 stearate and PEG-40 stearate
  • polyol fatty acid esters such as glyceryl stearate, sorbitan tristearate and oxyethylenated sorbitan stearates available under the trade names Tween® 20 or Tween® 60, for example; and their mixtures.
  • hydrophilic gelling agents mention may in particular be made of carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkyl acrylate copolymers, polyacryiamides, 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
  • polyacryiamides 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 also contains a progestogen, such as pregnenoion and 17-OH progesterone.
  • composition according to the invention finds in particular an application in the prevention and the treatment of the cutaneous signs of chronological or actinic aging.
  • the present invention therefore also relates to the cosmetic use of the composition mentioned above for preventing or treating the skin signs of chronological or actinic aging, in particular:
  • composition according to the invention comprises an effective amount of DHEA, sufficient to obtain the desired effect, and a physiologically acceptable medium.
  • phase A1, A2 and B are prepared separately by mixing their constituents under hot conditions, with stirring. Phases A1 and A2 are mixed hot, then phase B is added to them. The mixture thus obtained was transferred to a high pressure homogenizer where it is subjected to three passages at 600 bars before incorporation of phase C.
  • This composition can be used in twice-daily applications to prevent or treat the signs of aging such as wrinkles and fine lines, loss of radiance and dryness of the skin.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention concerns a composition containing: (a) DHEA, and (b) at least a desquamative agent selected among retinoids, acylated salicylic acid derivatives, HMG-CoA reductase inhibitors and sugar derivatives. The inventive composition is useful for fighting against chronological or actinic skin ageing, in particular for preventing or reducing the papery appearance of the skin, and/or for brightening up complexion, and/or for treating wrinkles and fine lines, and/or for toning up the skin, and/or for fighting against or preventing cutaneous atrophy.

Description

Composition, notamment cosmétique, renfermant la DHEA et un agent desquamant Composition, in particular cosmetic, containing DHEA and a scaling agent
La présente invention se rapporte à une composition renfermant la DHEA, en association avec au moins un agent desquamant.The present invention relates to a composition containing DHEA, in combination with at least one scaling agent.
La DHEA, ou déhydroépiandrostérone, est un stéroïde naturel produit essentiellement par les glandes corticosurrénales. La DHEA exogène, administrée par voie topique ou orale, est notamment 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.DHEA, or dehydroepiandrosterone, is a natural steroid produced primarily by the adrenal cortex. Exogenous DHEA, administered topically or orally, is particularly 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). It has also been described in US Pat. No. 5,843,932 the use of DHEA for remedying atrophy of the dermis by inhibiting the loss of collagen and connective tissue.
II a déjà été proposé dans le document US-4,542,129 d'associer la DHEA à un agent kératolytique tel que l'acide salicylique ou les α-hydroxyacides, pour contrer la formation de lésions cutanées acnéiformes qui pourraient apparaître sur les peaux prédisposées à l'acné, traitées avec la DHEA.It has already been proposed in document US Pat. No. 4,542,129 to combine DHEA with a keratolytic agent such as salicylic acid or α-hydroxy acids, to counter the formation of acneiform skin lesions which could appear on the skin predisposed to acne, treated with DHEA.
Toutefois, à la connaissance de la Demanderesse, il n'a encore jamais été suggéré que l'association de la DHEA avec d'autres agents desquamants choisis pouvait permettre de lutter efficacement contre les signes du vieillissement cutané.However, to the knowledge of the Applicant, it has never been suggested that the combination of DHEA with other selected desquamating agents could make it possible to effectively combat the signs of skin aging.
La présente invention a donc pour objet une nouvelle composition comprenant, dans un milieu physiologiquement acceptable, (a) la DHEA, et (b) au moins un agent desquamant choisi parmi les rétinoïdes, les dérivés acylés d'acide salicylique, les inhibiteurs d'HMG-CoA reductase et les dérivés de sucre.The subject of the present invention is therefore a new composition comprising, in a physiologically acceptable medium, (a) DHEA, and (b) at least one desquamating agent chosen from retinoids, acyl derivatives of salicylic acid, inhibitors of HMG-CoA reductase and sugar derivatives.
La DHEA a la formule (I) suivante :
Figure imgf000002_0001
La DHEA utilisable selon l'invention est par exemple disponible auprès de la société AKZO NOBEL.DHEA has the following formula (I):
Figure imgf000002_0001
The DHEA which can be used according to the invention is for example available from the company AKZO NOBEL.
La concentration en DHEA dans la composition selon l'invention est avantageusement comprise entre 0,001 % et 20% en poids, de préférence entre 0,01 et 10% en poids, plus préférentiellement entre 0,1 et 3% en poids, par rapport au poids total de la composition.The concentration of DHEA in the composition according to the invention is advantageously between 0.001% and 20% by weight, preferably between 0.01 and 10% by weight, more preferably between 0.1 and 3% by weight, relative to the total weight of the composition.
Comme agent desquamant, on peut utiliser les rétinoïdes tels que l'acide rétinoïque (all-trans ou 13-cis) et ses dérivés, le rétinaldehyde, le rétinol (vitamine A) et ses esters tels que le palmitate de rétinol, l'acétate de rétinol et le propionate de rétinol, ainsi que leurs mélanges.As scaling agent, retinoids such as retinoic acid (all-trans or 13-cis) and its derivatives, retinaldehyde, retinol (vitamin A) and its esters such as retinol palmitate, acetate can be used. retinol and retinol propionate, and mixtures thereof.
En variante, l'agent desquamant peut être un dérivé acylé d'acide salicylique, en particulier un acide 5-acyl-saiicylique tel que l'acide n-octanoyl-5-saiicylique, 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.Alternatively, the desquamating agent can be an acylated derivative of salicylic acid, in particular a 5-acyl-saiicylic acid such as n-octanoyl-5-saiicylic acid, n-dodecanoyl-5-salicylic acid and n-decanoyl-5-salicylic acid, 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-salicylic acid. This compound can be prepared as described in application FR-2,581,542 in the name of the Applicant.
Selon une autre possibilité, l'agent desquamant peut être choisi parmi les inhibiteurs • d'HMG-CoA reductase. Les inhibiteurs d'HMG-CoA-réductase peuvent être par exemple les composés suivants : mévastatine, lovastatine, pravastatine, simvastatine, fluvastatine, dalvastatine, 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. The HMG-CoA-reductase inhibitors can be, for example, the following compounds: mevastatin, lovastatin, pravastatin, simvastatin, fluvastatin, dalvastatin, and their derivatives and salts, in particular 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 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 corresponding to formula (I),
R-X-A (I)R-X-A (I)
dans laquelle : A 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 thiol, une fonction alcoxy, une fonction thio-éther, une fonction thio-ester, une fonction amide, une fonction carbamate et/ou une fonction urée,in which : A 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 thiol, 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 linking R and A, such as for example an amine, ether, amide, ester, urea, carbamate, thioester, thioether or sulfonamide function.
Ces composés sont décrits, ainsi que leur procédé de préparation, dans la demande EP-0 853 472.These compounds are described, as well as their preparation process, in application EP-0 853 472.
Comme dérivés de sucre préférés, on peut citer le N-butanoyI-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-butanoyI-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 0,1 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 0.1 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 peut se présenter sous toutes les formes galéniques normalement utilisées pour une application topique sur la peau, notamment sous forme d'une solution huileuse, d'une émulsion huile-dans-eau ou eau-dans-huiie ou multiple, d'une émulsion siiiconée, d'une microémulsion ou nanoémulsion, d'un gel huileux, d'un produit anhydre liquide, pâteux ou solide, d'une dispersion d'huile dans une phase aqueuse en présence de sphérules, ces sphérules pouvant être des nanoparticules polymériques telles que les nanosphères et les nanocapsules ou, mieux, des vésicules lipidiques de type ionique et/ou non-ionique.The composition according to the invention can be in all dosage forms normally used for topical application to the skin, in particular in the form of an oily solution, of an oil-in-water or water-in-oil or multiple emulsion. , a silicone emulsion, a microemulsion or nanoemulsion, an oily gel, a liquid, pasty or solid anhydrous product, an oil dispersion in an aqueous phase in the presence of spherules, these spherules possibly being polymeric nanoparticles such as nanospheres and nanocapsules or, better, lipid vesicles of ionic and / or nonionic type.
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, dans la phase aqueuse, dans les vésicules lipidiques et/ou dans les nanoparticules. Ces adjuvants, ainsi que leurs concentrations, doivent être tels qu'ils ne nuisent pas aux propriétés avantageuses de l'association d'actifs 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, into the aqueous phase, into the lipid vesicles and / or into the nanoparticles. These adjuvants, as well as their concentrations, must be such that they do not harm the advantageous properties of the combination of active 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 co- émulsionnant 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 co-emulsifier 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 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 (oil) can be used. avocado, soybean oil), oils of animal origin (lanolin), 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 glyceryle, 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, mention may, for example, be made of fatty acid and polyethylene glycol esters such as PEG-100 stearate, PEG-50 stearate and PEG-40 stearate; polyol fatty acid esters such as glyceryl stearate, sorbitan tristearate and oxyethylenated sorbitan stearates available under the trade names 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 polyacryiamides, 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 in particular be made of carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkyl acrylate copolymers, polyacryiamides, polysaccharides, natural gums and clays, and, as lipophilic gelling agents, cite modified clays such as bentones, metal salts of fatty acids and hydrophobic silica.
Comme actifs, on préfère que la composition selon l'invention renferme en outre un progestatif, tel que la prégnénoione et la 17-OH progestérone.As active agents, it is preferred that the composition according to the invention also contains a progestogen, such as pregnenoion and 17-OH progesterone.
La composition selon l'invention trouve en particulier une application dans la prévention et le traitement des signes cutanés du vieillissement chronologique ou actinique.The composition according to the invention finds in particular an application in the prevention and the treatment of the cutaneous signs of chronological or actinic aging.
La présente invention concerne donc également l'utilisation cosmétique de la composition mentionnée ci-dessus pour prévenir ou traiter les signes cutanés du vieillissement chronologique ou actinique, en particulier :The present invention therefore also relates to the cosmetic use of the composition mentioned above for preventing or treating the skin signs of chronological or actinic aging, in particular:
- pour prévenir ou réduire l'aspect papyracé de la peau, et/ou- to prevent or reduce the papery appearance of the skin, and / or
- pour raviver l'éclat du teint, et/ou- to revive the radiance of the complexion, and / or
- pour traiter les rides et ridules, et/ou - pour lutter contre le relâchement cutané, et/ou- to treat fine lines and wrinkles, and / or - to combat sagging skin, and / or
- pour lutter contre ou prévenir l'atrophie de la peau, et/ou- to fight against or prevent atrophy of the skin, and / or
- pour lutter contre la sécheresse de la peau.- to fight against dryness of the skin.
Dans tous les cas, la composition selon l'invention comprend une quantité efficace de DHEA, suffisante pour obtenir l'effet recherché, et un milieu physiologiquement acceptable.In all cases, the composition according to the invention comprises an effective amount of DHEA, sufficient to obtain the desired effect, and a physiologically acceptable medium.
L'invention sera maintenant illustrée par l'exemple non limitatif suivant. Dans cet exemple, les quantités sont indiquées en pourcentage pondéral, sauf indication contraire.The invention will now be illustrated by the following nonlimiting example. In this example, the quantities are indicated in percentage by weight, unless otherwise indicated.
EXEMPLE : composition cosmétiqueEXAMPLE: cosmetic composition
Phase A1Phase A1
2-octyldodécanol 20 %2-octyldodecanol 20%
DHEA 1 %DHEA 1%
Phase A2 Distéarate polyglycérolé (2 mol) 2 %Phase A2 Polyglycerolated distearate (2 mol) 2%
Mono-stéarate de PEG (8 OE) 1 ,35 %PEG mono-stearate (8 EO) 1.35%
Acide stéarique 1 %Stearic acid 1%
Conservateur 0,1 %Preservative 0.1%
Phase BPhase B
Acide n-octanoyl-5-salicylique 1 %1-octanoyl-5-salicylic acid 1%
Conservateurs 0,35 %Preservatives 0.35%
Neutralisants 0,25%Neutralizers 0.25%
Propylène glycol 10 % Eau qsp 100 %Propylene glycol 10% Water qs 100%
Phase CPhase C
Gélifiant 0,5 %0.5% gelling agent
Neutralisant 0,2 % Eau qspNeutralizing 0.2% Water qs
Cette composition peut être préparée de la manière suivante : les phases A1 , A2 et B sont préparées séparément par mélange de leurs constituants à chaud, sous agitation. Les phases A1 et A2 sont mélangées à chaud, puis la phase B leur est ajoutée. Le mélange ainsi obtenu a été transféré vers un homogénéisateur haute pression où il est soumis à trois passages à 600 bars avant incorporation de la phase C.This composition can be prepared in the following manner: phases A1, A2 and B are prepared separately by mixing their constituents under hot conditions, with stirring. Phases A1 and A2 are mixed hot, then phase B is added to them. The mixture thus obtained was transferred to a high pressure homogenizer where it is subjected to three passages at 600 bars before incorporation of phase C.
Cette composition peut être utilisée en applications bi-quotidiennes pour prévenir ou traiter les signes du vieillissement tels que les rides et ridules, la perte d'éclat du teint et le dessèchement de la peau. This composition can be used in twice-daily applications to prevent or treat the signs of aging such as wrinkles and fine lines, loss of radiance and dryness of the skin.

Claims

REVENDICATIONS
1. Composition renfermant la DHEA, caractérisée en ce qu'elle comprend en outre au moins un agent desquamant choisi parmi les rétinoïdes, les dérivés acylés d'acide salicylique, les inhibiteurs d'HMG-CoA reductase et les dérivés de sucre.1. Composition containing DHEA, characterized in that it also comprises at least one desquamating agent chosen from retinoids, acylated derivatives of salicylic acid, HMG-CoA reductase inhibitors and sugar derivatives.
2. Composition selon la revendication 1 , caractérisée en ce qu'elle renferme de 0,01 à 10% en poids de DHEA, par rapport au poids total de la composition.2. Composition according to claim 1, characterized in that it contains from 0.01 to 10% by weight of DHEA, relative to the total weight of the composition.
3. Composition selon la revendication 2, caractérisée en ce qu'elle renferme de 0,1 à 3% en poids de DHEA, par rapport au poids total de la composition.3. Composition according to claim 2, characterized in that it contains from 0.1 to 3% by weight of DHEA, relative to the total weight of the composition.
4. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce qu'elle comprend de 0,1 % à 5% en poids d'agent desquamant, par rapport au poids total de la composition.4. Composition according to any one of the preceding claims, characterized in that it comprises from 0.1% to 5% by weight of scaling agent, relative to the total weight of the composition.
5. Composition selon la revendication 4, caractérisée en ce qu'elle comprend de 0,5% à 3% en poids d'agent desquamant, par rapport au poids total de la composition.5. Composition according to claim 4, characterized in that it comprises from 0.5% to 3% by weight of scaling agent, relative to the total weight of the composition.
6. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce que ledit rétinoïde est choisi parmi l'acide rétinoïque (all-trans ou 13-cis) et ses dérivés, le rétinaldehyde, le rétinol (vitamine A) et ses esters tels que le palmitate de rétinol, l'acétate de rétinol et le propionate de rétinol, ainsi que leurs mélanges.6. Composition according to any one of the preceding claims, characterized in that said retinoid is chosen from retinoic acid (all-trans or 13-cis) and its derivatives, retinaldehyde, retinol (vitamin A) and its esters such as retinol palmitate, retinol acetate and retinol propionate, and mixtures thereof.
7. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce que ledit dérivé acylé d'acide salicylique est choisi parmi l'acide n-octanoyl-5- salicyiique, l'acide n-dodécanoyl-5-salicylique et l'acide n-décanoyl-5-salicylique, sous forme libre ou salifiée.7. Composition according to any one of the preceding claims, characterized in that said acylated derivative of salicylic acid is chosen from n-octanoyl-5-salicyic acid, n-dodecanoyl-5-salicylic acid and n-decanoyl-5-salicylic acid, in free or salified form.
8. Composition selon la revendication 7, caractérisée en ce que ledit dérivé acylé d'acide salicylique est l'acide n-octanoyl-5-salicylique.8. Composition according to claim 7, characterized in that said acylated derivative of salicylic acid is n-octanoyl-5-salicylic acid.
9. Composition selon l'une quelconque des revendications précédentes, 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, notamment leurs sels de sodium.9. Composition according to any one of the preceding claims, characterized in that the said HMG-CoA reductase inhibitor is chosen from the compounds following mevastatin, lovastatin, pravastatin, simvastatin, fluvastatin, dalvastatin, and their derivatives and salts, especially their sodium salts.
10. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce que ledit dérivé de sucre est choisi parmi un carbohydrate ou dérivé de carbohydrate répondant à la formule (I),10. Composition according to any one of the preceding claims, characterized in that said sugar derivative is chosen from a carbohydrate or carbohydrate derivative corresponding to formula (I),
R-X-A (I)R-X-A (I)
dans laquelle :in which :
A 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 amine, une fonction acide, une fonction ester, un thiol, une fonction alcoxy, une fonction thio-éther, une fonction thio-ester, une fonction amide, une fonction carbamate et/ou une fonction urée,A 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 amine function, an acid function, an ester function, a thiol, 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 amine, 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 amine 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 amine, éther, amide, ester, urée, carbamate, thioester, thioéther ou sulfonamide.X represents a function linking R and A, such as for example an amine, ether, amide, ester, urea, carbamate, thioester, thioether or sulfonamide function.
11. Composition selon la revendication 10, caractérisée en ce que ledit dérivé de sucre est choisi parmi le N-butanoyI-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. 11. Composition according to claim 10, characterized in that the said sugar derivative is chosen from N-butanoyI-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.
12. Composition selon la revendication 11 , caractérisée en ce que ledit dérivé de sucre est le 6'-0-octanoyl-D-maltose.12. Composition according to claim 11, characterized in that said sugar derivative is 6'-0-octanoyl-D-maltose.
13. Composition selon l'une quelconque des revendications précédentes, caractérisé en ce qu'elle renferme en outre un progestatif.13. Composition according to any one of the preceding claims, characterized in that it also contains a progestin.
14. Composition selon la revendication 13, caractérisée en ce que ledit progestatif est choisi parmi la prégnénolone et la 17-OH progestérone.14. Composition according to Claim 13, characterized in that the said progestin is chosen from pregnenolone and 17-OH progesterone.
15. Utilisation cosmétique de la composition selon l'une quelconque des revendications précédentes pour prévenir ou traiter les signes cutanés du vieillissement chronologique ou actinique.15. Cosmetic use of the composition according to any one of the preceding claims for preventing or treating the skin signs of chronological or actinic aging.
16. Utilisation cosmétique de la composition selon l'une quelconque des revendications 1 à 14 pour prévenir ou réduire l'aspect papyrace de la peau, et/ou pour raviver l'éclat du teint, et/ou pour traiter les rides et ridules, et/ou pour lutter contre le relâchement cutané, et/ou pour lutter contre ou prévenir l'atrophie de la peau et/ou pour lutter contre la sécheresse de la peau. 16. Cosmetic use of the composition according to any one of claims 1 to 14 for preventing or reducing the papery appearance of the skin, and / or for reviving the radiance of the complexion, and / or for treating wrinkles and fine lines, and / or to combat sagging skin, and / or to combat or prevent atrophy of the skin and / or to combat dryness of the skin.
PCT/FR2000/002682 1999-10-13 2000-09-28 Composition, in particular cosmetic, containing dihydroepiandosterone (dhea) and a desquamative agent WO2001026619A2 (en)

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FR9912773A FR2799645B1 (en) 1999-10-13 1999-10-13 USE OF DHEA OR ITS PRECURSORS OR METABOLIC DERIVATIVES AS DEPIGMENTANT
FR0009228A FR2799649B1 (en) 1999-10-13 2000-07-13 COMPOSITION, PARTICULARLY COSMETIC, CONTAINING DHEA AND A DESQUAMANT AGENT
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FR2827767A1 (en) * 2001-07-27 2003-01-31 Oreal Aqueous suspension of nanocapsules containing dehydroepiandrosterone, useful in cosmetic or dermatological compositions

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FR2826577A1 (en) * 2001-06-29 2003-01-03 Oreal USE OF LYS-PRO-VAL TRIPEPTIDE (KPV) TO ENHANCE THE BARRIER FUNCTION OF THE SKIN
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FR2827767A1 (en) * 2001-07-27 2003-01-31 Oreal Aqueous suspension of nanocapsules containing dehydroepiandrosterone, useful in cosmetic or dermatological compositions
WO2003013445A1 (en) * 2001-07-27 2003-02-20 L'oreal Nanocapsules containing a steroid for cosmetic compositions

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