WO2003035023A1 - Cosmetic composition containing a dhea derivative and a soothing agent - Google Patents
Cosmetic composition containing a dhea derivative and a soothing agent Download PDFInfo
- Publication number
- WO2003035023A1 WO2003035023A1 PCT/FR2002/003510 FR0203510W WO03035023A1 WO 2003035023 A1 WO2003035023 A1 WO 2003035023A1 FR 0203510 W FR0203510 W FR 0203510W WO 03035023 A1 WO03035023 A1 WO 03035023A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dehydroepiandrosterone
- oxo
- hydroxy
- skin
- acetyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
Classifications
-
- 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
- A61Q19/004—Aftersun preparations
-
- 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
- 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
- A61Q19/005—Preparations for sensitive skin
-
- 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
- A61K2800/75—Anti-irritant
-
- 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
- Cosmetic composition containing a DHEA derivative and a soothing agent
- the invention relates to a composition containing, in a physiologically acceptable medium, at least one DHEA derivative in combination with at least one agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases.
- the invention also relates to the cosmetic use of this composition, in particular for soothing skin disorders and skin disturbances chosen from sensitive skin, skin discomfort, skin tightness, itching of the skin, skin irritations, swelling skin redness and / or feelings of skin heat.
- the invention also relates to a soothing cosmetic treatment method comprising the topical application of such a composition.
- compositions with soothing activity in particular for skin disturbances such as, for example, sensitive skin, skin discomfort, skin tightness, itchy skin, skin irritations, swelling of the skin, redness of the skin, sensations of skin heat.
- PHA2 phospholipases A2
- Arachidonic acid is then oxidized enzymatically by lipoxygenases (Lox) or by human prostaglandins synthetases (PGHS) to give pro-inflammatory mediators such as prostaglandins and leukotrienes (William L. Smith, 1989, biochem J, 259.315-324).
- Lix lipoxygenases
- PGHS human prostaglandins synthetases
- DHEA or dehydroepiandrosterone is a natural steroid produced mainly 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 strengthening thus the barrier effect of the skin (US Pat. No. 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.
- DHEA has effects of a hormonal nature which can make its use delicate. Therefore, we understand that we have sought to have DHEA derivatives having properties as interesting as DHEA itself, but having no hormonal effects.
- DHEA derivatives 3 ⁇ -acetoxy-7-oxo-DHEA or ⁇ 5- androstene-3 ⁇ -acetoxy-7,17-dione, which has been described as being effective in modulating the immune system, is already known.
- -5,292,730; US-5,585,371; US-5,641,766) the treatment of Alzheimer's disease (US-5,707,983) and the treatment of HIV syndrome (US-5,885,977) and to promote weight loss (US-5,296,481; US 5,807,848).
- Document WO 99/25333 also mentions the use, in particular topical use, of 3 ⁇ -acetoxy-7-oxo-DHEA in the prophylactic and curative treatment of lupus erythematosus, which is a disorder of the immune system capable of affecting several organs. and manifested, in the skin, by a transverse redness of the face and / or by plaques of scaly erythema disseminated on the body.
- the 3 ⁇ -hydroxy group is transformed into a carbamate or is esterified with (i) a C2-C22 aliphatic acid, normal, branched, saturated or unsaturated, (ii) a C7-C22 aromatic acid, (iii) a dicarboxylic acid in C3 or more, for which only one carbonyl group is esterified with the 3-hydroxy group of the steroid, (iv) an inorganic acid such as sulfuric acid and phosphoric acid.
- Document US 5,424,463 describes 7-keto-DHEA and its hydrolyzable derivatives as being effective in promoting weight loss.
- DHEA derivatives with at least one agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases.
- the object of the present invention is therefore to be able to have new compositions thus exhibiting an enhanced soothing activity while not presenting any significant side effects.
- composition comprising, in a physiologically acceptable medium, at least one derivative of DHEA in association with at least one agent capable of inhibiting at least one enzyme, chosen among phospholipases A2, lipoxygenases and / or human prostaglandins synthetases, the said agent not being an inhibitor of 5 ⁇ -reductase.
- at least one derivative of DHEA in association with at least one agent capable of inhibiting at least one enzyme, chosen among phospholipases A2, lipoxygenases and / or human prostaglandins synthetases, the said agent not being an inhibitor of 5 ⁇ -reductase.
- the DHEA derivative according to the invention corresponds to the following formula (I):
- heterocycle can advantageously be chosen from an indole, a pyrimidine, a piperidine, a morpholine, a pyran , furan, piperazine, pyridine;
- alkylcarbonyl group the C1-C24 alkyl part of which is saturated or unsaturated, linear or branched, cyclic, and optionally substituted by one or more groups chosen from -OR 'and / or -SR' and / or -COOR 'and / or -NR'R 'and / or halogen and / or sulfate and / or phosphate and or aryl and / or heterocycle
- said heterocycle can advantageously be chosen from an indole, a pyrimidine, piperidine, morpholine, pyran, furan, piperazine, pyridine;
- an arylcarbonyl group preferably a phenylcarbonyl, or an arylalkylcarbonyl group, preferably a benzylcarbonyl, optionally substituted by one or more groups -OR 'and / or -SR' and / or -COOR 'and / or -NR'R' and / or halogen and / or aryl and / or heterocycle;
- R ′ is chosen from a hydrogen atom, a C1-C12, preferably C1-C6, saturated or unsaturated, linear or branched, cyclic alkyl group which may optionally contain one or more heteroatoms, optionally functionalized with one or several groups -OR ", -COOR", halogen, -NR “R”; or by an aryl group, preferably a phenyl, optionally functionalized by one or more groups -OR ", -COOR", halogen or -NR “R”; preferably R 'represents a hydrogen atom, methyl, ethyl, butyl, propyl, isopropyl; and,
- R represents a hydrogen atom, an alkyl chain, preferably C1-C6, saturated or unsaturated, linear or branched or cyclic, preferably R" represents a hydrogen atom, a methyl, an ethyl, a butyl, propyl, isopropyl;
- the substituents R', respectively R " are identical or different, and that advantageously the group -NR'R 'represents an amino acid, preferably chosen from L-alanine, L-arginine, L-asparagine, L-aspartic acid, L-cysteine, L-glutamine, L-glutamic acid, glycine, L-histidine, L-isoleucine, L-leucine, L-lysine, L-methionine, L-phenylalanine, L-proline, L-serine, L-threonine, L-tryptophan, L-tyrosine, L-valine;
- the invention also relates to the optical and / or geometric isomers of the DHEA derivatives of formula (I) alone or as a mixture in all proportions, as well as the physiologically acceptable salts of these derivatives.
- the stereochemistry in position 7 of the DHEA derivatives of formula (I) for which R3 represents an OR4 radical can be alpha ( ⁇ ), beta ( ⁇ ) or the mixture of the two in any proportion.
- the preferred DHEA derivatives of formula (I) are those for which R2 represents a hydrogen atom, R3 represents a radical OR4, with R4 having the same definitions as those given above of preferred way for R1.
- the compounds corresponding to formula (I) are chosen from at least one of the following compounds: - ⁇ 5-androstene-3 ⁇ -hydroxy-7,17-dione or 7-oxo-dehydroepiandrosterone (7-oxo-
- DHEA derivatives of formula (I) according to the invention are easily accessible from a synthetic point of view, in particular not the implementation of one of the synthesis methods described in US Patents 5,424,463; FR-2,771,105; US-5,869,709; US-6, 111, 118 or WO-94/085888.
- the agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases is chosen from at least one of the following substances: pentacyclic triterpenes and extracts of plant (in particular Glycyrrhiza glabra) containing it, in particular oleanolic acid, ursolic acid and its salts, boswellic acid and its salts; betullic acid and its salts; ⁇ glycyrrhetinic acid and its salts and / or its derivatives such as glycyrrhetic acid monoglucuronide, stearyl glycyrrhetinate, 3-stearoyloxy glycyrrhetic acid); - extracts of Paeonia suffruticosa;
- oils unsaturated in omega 3 such as oils of rose musca, blackcurrant oils, ecchium oils, fish oils;
- Centipeda cunnighami extracts in particular phytoplenolin ® from Bio-Botanica; - Helianthus annuus extracts, in particular Helioxin ® from Silab;
- the agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases is chosen from at least one of the following substances:
- DHEA derivative of formula (I) and of agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases present in the composition obviously depends on the effect. research.
- the composition according to the invention may contain from 0.0001% to 10% by weight, preferably from 0.01% to 5% by weight, of DHEA derivative of formula (I) as defined above, relative to the total weight of the composition.
- the composition according to the invention may contain from 0.0001 to 10%, preferably from 0.001 to 5% by weight, of agent capable of inhibiting at least one enzyme chosen from phospholipases A2 , lipoxygenases and / or human prostaglandins synthetases as defined above, relative to the total weight of the composition.
- compositions according to the invention can be in all the galenical forms normally used.
- the compositions according to the invention can be intended for a cosmetic or pharmaceutical application, particularly dermatological.
- the compositions according to the invention are intended for a cosmetic application.
- another object of the invention relates to the cosmetic use of a composition containing, in a physiologically acceptable medium, at least one DHEA derivative of formula (I) as defined above with at least agent capable of 'inhibit at least one enzyme selected from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases, to soothe the skin and / or scalp.
- Another subject of the invention also relates to the cosmetic use of a composition containing, in a physiologically acceptable medium, at least one DHEA derivative of formula (I) as defined above with at least agent capable of inhibit at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases, to prevent and / or treat sensitive skin and / or skin discomfort and / or skin tightness and / or itching of the skin and / or skin irritations and / or skin swelling and / or skin redness and / or feelings of skin heat.
- at least agent capable of inhibit at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases
- compositions according to the invention are preferably suitable for topical application to keratin materials such as the skin, the scalp, the mucous membranes, the hair, the eyelashes or the nails. They 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 emulsion, a silicone emulsion , a microemulsion or nanoemulsion, an aqueous or oily gel or a liquid, pasty or solid anhydrous product.
- compositions 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. They can optionally be applied to the skin in the form of an aerosol, patch or powder. They can also be in solid form, and for example in the form of a stick. They can be used as a care product and / or as a make-up product for the skin. They may alternatively be in the form of a shampoo or conditioner.
- compositions in the form of a foam or also in the form of aerosol compositions also comprising a propellant under pressure it is also possible to envisage a composition in the form of a foam or also in the form of aerosol compositions also comprising a propellant under pressure.
- the composition of the invention may also contain the adjuvants usual in the cosmetic field, such as hydrophilic or lipophilic gelling agents, preservatives, antioxidants, solvents, perfumes, fillers, pigments, absorbents of odor and coloring matter.
- the amounts of these various adjuvants are those conventionally used in the field 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.
- the proportion of the fatty phase can range from 2 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.
- the emulsion may, in addition, contain lipid vesicles.
- the fatty phase can represent more than 90% of the total weight of the composition.
- the cosmetic composition can also contain adjuvants customary in the cosmetic field, such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic additives, preservatives, antioxidants, solvents, perfumes, fillers, filters, odor absorbers and coloring matters.
- adjuvants customary in the cosmetic field such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic additives, preservatives, antioxidants, solvents, perfumes, fillers, filters, odor absorbers and coloring matters.
- the amounts of these various adjuvants are those conventionally used in the cosmetic field, and for example from 0.01% to 10% of the total weight of the composition.
- These adjuvants depending on their nature, can be introduced into the fatty phase, into the aqueous phase and / or into the lipid spherules.
- 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; fatty acid and polyol 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
- fatty acid and polyol 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.
- solvents which can be used in the invention mention may be made of lower alcohols, in particular ethanol and isopropanol, propylene glycol.
- hydrophilic gelling agents which can be used in the invention, mention may be made of carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkyl acrylate copolymers, polyacrylamides, polysaccharides such as hydroxypropylcellulose, natural gums and clays, and, as lipophilic gelling agents, mention may be made of modified clays such as bentones, metal salts of fatty acids such as aluminum stearates and hydrophobic silica, ethylcellulose, polyethylene.
- carboxyvinyl polymers carboxyvinyl polymers
- acrylic copolymers such as acrylate / alkyl acrylate copolymers
- polyacrylamides polysaccharides
- polysaccharides such as hydroxypropylcellulose
- natural gums and clays and, as lipophilic gelling agents
- modified clays such as bentones, metal salts of fatty acids such as aluminum stearates and hydrophobic silica
- the combination according to the invention can be used in cosmetics to soothe the skin and / or the scalp.
- another object of the present invention relates to cosmetic use as a soothing agent, by topical application to the skin and / or the scalp, of the combination comprising at least one DHEA derivative of formula (I) as defined above with at least one agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases as defined above.
- the present invention also relates to cosmetic use as an agent for preventing and / or treating sensitive skin, skin discomfort, skin tightness, itchy skin, skin irritation, skin swelling, skin rash and / or the sensations of skin heat, by topical application to the skin and / or leather, of the combination comprising at least one DHEA derivative of formula (I) as defined above with at least agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases as defined above.
- sensitive skins is meant the skins which have been characterized by the Applicant in patent EP 0 680 749 B1.
- the Applicant has been able to show that the symptoms linked to sensitive skin consist of more or less painful sensations felt in a skin area, such as tingling, tingling, itching or itching, burning, redness, heating, discomfort, tightness, etc.
- These symptoms can appear in response to various factors such as, among others, sweat, friction, emotions, food, wind, friction, razor, soap, surfactants, hard water with a high concentration of limestone, temperature variations or wool.
- sensitive skin covers both irritable skin and intolerant skin.
- the present invention also relates to a soothing cosmetic treatment process for keratin materials comprising the topical application thereon of a composition containing, in a physiologically acceptable medium, at least one DHEA derivative of formula (I) such as defined previously with at least agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases.
- a composition containing, in a physiologically acceptable medium, at least one DHEA derivative of formula (I) such as defined previously with at least agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases.
- It relates more particularly to a cosmetic treatment process for sensitive skin, skin discomfort, skin tightness, itching of the skin, skin irritations, swelling of the skin, redness of the skin, sensations of skin heat comprising the application topical on the skin or scalp of a composition containing, in a physiologically acceptable medium, at least one DHEA derivative of formula (I) as defined above in combination with at least agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases.
- compositions illustrate the invention without limiting it in any way.
- proportions indicated are percentages by weight, unless otherwise indicated.
- the above composition can be prepared in the following manner: the polymer of phase A is dispersed in water at 40 ° C. The constituents of phase B are heated to 70 ° C until complete dissolution and then the temperature is reduced to 40 ° C. The constituents of phase C are mixed at 50 ° C. '
- Phase D is introduced into the mixture previously obtained.
- This cream is particularly well suited to the treatment of sensitive skin in single or bi daily application.
- This cream is beige in color and suitable for the treatment of the skin, by application to the face twice a day.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Description
Composition cosmétique renfermant un dérivé de la DHEA et un agent apaisant Cosmetic composition containing a DHEA derivative and a soothing agent
L'invention se rapporte à une composition renfermant, dans un milieu physiologiquement acceptable, au moins un dérivé de la DHEA en association avec au moins un agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases.The invention relates to a composition containing, in a physiologically acceptable medium, at least one DHEA derivative in combination with at least one agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases.
L'invention se rapporte également à l'utilisation cosmétique de cette composition, notamment pour apaiser les désordres cutanés et les perturbations cutanées choisis parmi les peaux sensibles, l'inconfort cutané, les tiraillements cutanés, les démangeaisons cutanées, les irritations cutanées, les gonflements cutanés, les rougeurs cutanées et/ou les sensations de chaleur cutanée.The invention also relates to the cosmetic use of this composition, in particular for soothing skin disorders and skin disturbances chosen from sensitive skin, skin discomfort, skin tightness, itching of the skin, skin irritations, swelling skin redness and / or feelings of skin heat.
L'invention a également pour objet un procédé de traitement cosmétique apaisant comprenant l'application topique d'une telle composition.The invention also relates to a soothing cosmetic treatment method comprising the topical application of such a composition.
On sait que l'être humain peut subir des phénomènes de types agressifs qui se caractérisent par un sentiment d'inconfort cutané, des tiraillements, des démangeaisons, la sensation de chaleur cutanée, ou des rougeurs.We know that the human being can undergo phenomena of aggressive types which are characterized by a feeling of cutaneous discomfort, tightness, itching, the sensation of cutaneous heat, or redness.
On recherche depuis de nombreuses années des substances permettant de lutter contre ces types d'agression.We have been looking for many years for substances to fight against these types of aggression.
Même si des solutions ont déjà été proposées, il demeure constamment intéressant de disposer de nouvelles compositions à activité apaisante, notamment pour des perturbations cutanées telles que, par exemple, les peaux sensibles, l'inconfort cutané, les tiraillements cutanés, les démangeaisons cutanées, les irritations cutanées, les gonflements cutanés, les rougeurs cutanées, les sensations de chaleur cutanée.Even if solutions have already been proposed, it remains constantly interesting to have new compositions with soothing activity, in particular for skin disturbances such as, for example, sensitive skin, skin discomfort, skin tightness, itchy skin, skin irritations, swelling of the skin, redness of the skin, sensations of skin heat.
Parmi les facteurs responsables de ces phénomènes de type agressif on peut citer les enzymes impliquées dans la cascade de l'acide arachidonique. Les principales enzymes impliquées dans la cascade de l'acide arachidonique sont au nombre de trois. Les premières sont les phospholipases A2 (PLA2) dont la fonction physiologique est la libération des acides gras estérifiés dans les phospholipides membranaires qui sont transformés en acide arachidonique. L'acide arachidonique est ensuite oxydé par voie enzymatique par les lipoxygénases (Lox) ou par les prostaglandines humaines synthetases (PGHS) pour donner des médiateurs pro-inflammatoires tels que les prostaglandines et les leukotriènes (William L. Smith, 1989, biochem J, 259,315-324). (Among the factors responsible for these aggressive type phenomena, mention may be made of the enzymes involved in the arachidonic acid cascade. There are three main enzymes involved in the arachidonic acid cascade. The first are the phospholipases A2 (PLA2) whose physiological function is the release of the esterified fatty acids in the membrane phospholipids which are transformed into arachidonic acid. Arachidonic acid is then oxidized enzymatically by lipoxygenases (Lox) or by human prostaglandins synthetases (PGHS) to give pro-inflammatory mediators such as prostaglandins and leukotrienes (William L. Smith, 1989, biochem J, 259.315-324). (
De nombreuses substances sont connues dans l'art antérieur pour inhiber au moins une de ces enzymes.Many substances are known in the prior art to inhibit at least one of these enzymes.
A cet égard, on peut citer par exemple les huiles végétales (Lipids, 32(7), 759-767), les triterpènes et les huiles de poissons (Heller and Coll. Lipdi mediators in inflammatory disorders, Drugs, 55 (4),487-496).In this regard, there may be mentioned for example vegetable oils (Lipids, 32 (7), 759-767), triterpenes and fish oils (Heller and Coll. Lipdi mediators in inflammatory disorders, Drugs, 55 (4), 487-496).
Toutefois, il subsiste le besoin de renforcer l'efficacité de ces composés pour apaiser certains désordres et perturbations, notamment cutanés.However, there remains the need to reinforce the effectiveness of these compounds to soothe certain disorders and disturbances, in particular cutaneous.
Or, il est apparu à la Demanderesse que l'association d'un dérivé de la DHEA avecun agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases pouvait permettre d'améliorer l'efficacité des compositions comprenant ledit agent inhibiteur des dites enzymes.However, it appeared to the Applicant that the combination of a DHEA derivative with an agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases could make it possible to improve the effectiveness of the compositions comprising said agent inhibiting said enzymes.
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 2803513), à moduler la pigmentation de la peau et des cheveux EP-1092423 et à lutter contre l'atrophie de l'épiderme (FR 00/06154).DHEA or dehydroepiandrosterone is a natural steroid produced mainly 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 strengthening thus the barrier effect of the skin (US Pat. No. 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 2803513), to modulate the pigmentation of the skin and of the hair EP-1092423 and to fight against the atrophy of the 'epidermis (FR 00/06154).
Toutefois, la DHEA présente des effets de nature hormonale pouvant rendre son utilisation délicate. De ce fait, on comprend que l'on ait cherché à disposer de dérivés de la DHEA présentant des propriétés aussi intéressantes que la DHEA elle-même, mais n'ayant pas d'effets hormonaux. Parmi les dérivés de la DHEA, on connaît déjà la 3β-acétoxy-7-oxo-DHEA ou Δ5- androstène-3β-acétoxy-7,17-dione, qui a été décrite comme étant efficace dans la modulation du système immunitaire (US-5,292,730 ; US-5,585,371 ; US-5,641 ,766), le traitement de la maladie d'Alzheimer (US-5,707,983) et le traitement du syndrome HIV (US-5,885,977) et pour favoriser la perte de poids (US-5,296,481 ; US-5,807,848).However, DHEA has effects of a hormonal nature which can make its use delicate. Therefore, we understand that we have sought to have DHEA derivatives having properties as interesting as DHEA itself, but having no hormonal effects. Among the DHEA derivatives, 3β-acetoxy-7-oxo-DHEA or Δ5- androstene-3β-acetoxy-7,17-dione, which has been described as being effective in modulating the immune system, is already known. -5,292,730; US-5,585,371; US-5,641,766), the treatment of Alzheimer's disease (US-5,707,983) and the treatment of HIV syndrome (US-5,885,977) and to promote weight loss (US-5,296,481; US 5,807,848).
Le document WO 99/25333 mentionne en outre l'utilisation, notamment topique, de la 3β-acétoxy-7-oxo-DHEA dans le traitement prophylactique et curatif du lupus érythémateux, qui est un trouble du système immunitaire susceptible d'affecter plusieurs organes et se manifestant, au niveau de la peau, par une rougeur transversale de la face et/ou par des plaques d'érythème squameux disséminées sur le corps.Document WO 99/25333 also mentions the use, in particular topical use, of 3β-acetoxy-7-oxo-DHEA in the prophylactic and curative treatment of lupus erythematosus, which is a disorder of the immune system capable of affecting several organs. and manifested, in the skin, by a transverse redness of the face and / or by plaques of scaly erythema disseminated on the body.
Le document US 5,424,463 décrit notamment la 7-céto-DHEA (ou Δ5-androstène-3β- ol-7,17-dione) ainsi que ses dérivés hydrolysables obtenus par modification du groupe 3β-hydroxy, lesdits dérivés étant susceptibles de redonner la 7-céto-DHEA après hydrolyse. Le groupe 3β-hydroxy est transformé en carbamate ou est estérifié par (i) un acide aliphatique en C2-C22, normal, branché, saturé ou insaturé, (ii) un acide aromatique en C7-C22, (iii) un acide dicarboxylique en C3 ou plus, pour lequel seul un groupement carbonyl est estérifié avec le groupe 3-hydroxy du stéroïde, (iv) un acide inorganique tel que l'acide sulfurique et l'acide phosphorique. Le document US 5,424,463 décrit la 7-céto-DHEA et ses dérivés hydrolysables comme étant efficaces pour favoriser la perte de poids.Document US 5,424,463 describes in particular 7-keto-DHEA (or Δ5-androstene-3β-ol-7,17-dione) as well as its hydrolysable derivatives obtained by modification of the 3β-hydroxy group, said derivatives being capable of restoring 7 -keto-DHEA after hydrolysis. The 3β-hydroxy group is transformed into a carbamate or is esterified with (i) a C2-C22 aliphatic acid, normal, branched, saturated or unsaturated, (ii) a C7-C22 aromatic acid, (iii) a dicarboxylic acid in C3 or more, for which only one carbonyl group is esterified with the 3-hydroxy group of the steroid, (iv) an inorganic acid such as sulfuric acid and phosphoric acid. Document US 5,424,463 describes 7-keto-DHEA and its hydrolyzable derivatives as being effective in promoting weight loss.
Le document WO98/40074 décrit encore l'utilisation de dérivés de la 7-hydroxy-DHEA estérifiés en position 3 et/ou 7 pour traiter le vieillissement cutané.Document WO98 / 40074 further describes the use of 7-hydroxy-DHEA derivatives esterified in position 3 and / or 7 to treat skin aging.
Cependant, à la connaissance de la Demanderesse, il n'a encore jamais été suggéré d'associer des dérivés de la DHEA avec au moins un agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases. Le but de la présente invention est donc de pouvoir disposer de nouvelles compositions présentant ainsi une activité apaisante renforcée tout en ne présentant pas d'effets secondaires notables.However, to the knowledge of the Applicant, it has never been suggested to associate DHEA derivatives with at least one agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases. The object of the present invention is therefore to be able to have new compositions thus exhibiting an enhanced soothing activity while not presenting any significant side effects.
Ce but et d'autres sont atteints par la présente invention qui a pour objet une composition comprenant, dans un milieu physiologiquement acceptable, au moins un dérivé de la DHEA en association avec au moins un agent capable d'inhiber au moins une enzyme, choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases, le dit agent n'étant pas un inhibiteur de la 5α- réductase.This object and others are achieved by the present invention which relates to a composition comprising, in a physiologically acceptable medium, at least one derivative of DHEA in association with at least one agent capable of inhibiting at least one enzyme, chosen among phospholipases A2, lipoxygenases and / or human prostaglandins synthetases, the said agent not being an inhibitor of 5α-reductase.
Le dérivé de la DHEA selon l'invention répond à la formule (I) suivante :The DHEA derivative according to the invention corresponds to the following formula (I):
(I) dans laquelle : - R1 est choisi parmi : (I) in which: - R1 is chosen from:
- un atome d'hydrogène ;- a hydrogen atom;
- un groupe alkyle en C1-C24, saturé ou insaturé, linéaire ou ramifié, cyclique pouvant éventuellement contenir un ou plusieurs hétéroatomes, et éventuellement substitué par un ou plusieurs groupes choisis parmi -OR' et/ou -SR' et ou -COOR' et/ou -NR'R' et/ou halogène et/ou sulfate et/ou phosphate et/ou aryle et/ou hétérocycle, ledit hétérocycle pouvant avantageusement être choisi parmi un indole, une pyrimidine, une pipéridine, une morpholine, un pyrane, un furane, une pipérazine, une pyridine ;- a C1-C24 alkyl group, saturated or unsaturated, linear or branched, cyclic which may optionally contain one or more heteroatoms, and optionally substituted by one or more groups chosen from -OR 'and / or -SR' and or -COOR ' and / or -NR'R 'and / or halogen and / or sulfate and / or phosphate and / or aryl and / or heterocycle, said heterocycle can advantageously be chosen from an indole, a pyrimidine, a piperidine, a morpholine, a pyran , furan, piperazine, pyridine;
- un groupe alkylcarbonyle, dont la partie alkyle en C1-C24 est saturée ou insaturée, linéaire ou ramifiée, cyclique, et éventuellement substituée par un ou plusieurs groupes choisi parmi -OR' et/ou -SR' et/ou -COOR' et/ou -NR'R' et/ou halogène et/ou sulfate et/ou phosphate et ou aryle et/ou hétérocycle, ledit hétérocycle pouvant avantageusement être choisi parmi un indole, une pyrimidine, une pipéridine, une morpholine, un pyrane, un furane, une pipérazine, une pyridine ;an alkylcarbonyl group, the C1-C24 alkyl part of which is saturated or unsaturated, linear or branched, cyclic, and optionally substituted by one or more groups chosen from -OR 'and / or -SR' and / or -COOR 'and / or -NR'R 'and / or halogen and / or sulfate and / or phosphate and or aryl and / or heterocycle, said heterocycle can advantageously be chosen from an indole, a pyrimidine, piperidine, morpholine, pyran, furan, piperazine, pyridine;
- un groupe arylcarbonyle, de préférence un phénylcarbonyle, ou un groupe arylalkylcarbonyle, de préférence un benzylcarbonyle, éventuellement substitué par un ou plusieurs groupes -OR' et/ou -SR' et/ou -COOR' et/ou -NR'R' et/ou halogène et/ou aryle et/ou hétérocycle ;- an arylcarbonyl group, preferably a phenylcarbonyl, or an arylalkylcarbonyl group, preferably a benzylcarbonyl, optionally substituted by one or more groups -OR 'and / or -SR' and / or -COOR 'and / or -NR'R' and / or halogen and / or aryl and / or heterocycle;
- un groupe O=P(OH)OR' ;- a group O = P (OH) OR ';
- un groupe (O)2SOR' ;- a group (O) 2 SOR ';
- un groupe trialkylsilyle (SiR'3) dans lequel les 3 groupes R' peuvent être identiques ou différents ;- a trialkylsilyl group (SiR ' 3 ) in which the 3 R' groups can be identical or different;
- un groupe carbonyloxyalkyle (R'OCO) ;- a carbonyloxyalkyl group (R'OCO);
- un groupe carbonylaminealkyle (R'NHCO) ;- a carbonylaminealkyle group (R'NHCO);
dans lesquels R' est choisi parmi un atome d'hydrogène, un groupe alkyle en C1- C12, de préférence en C1-C6, saturé ou insaturé, linéaire ou ramifié, cyclique pouvant éventuellement contenir un ou plusieurs heteroatomes, éventuellement fonctionnalisé par un ou plusieurs groupes -OR", -COOR", halogène, -NR"R"; ou par un groupe aryle, de préférence un phényle, éventuellement fonctionnalisé par un ou plusieurs groupes -OR", -COOR", halogène ou -NR"R" ; de préférence R' représente un atome d'hydrogène, un méthyle, un éthyle, un butyle, un propyle, un isopropyle ; et,in which R ′ is chosen from a hydrogen atom, a C1-C12, preferably C1-C6, saturated or unsaturated, linear or branched, cyclic alkyl group which may optionally contain one or more heteroatoms, optionally functionalized with one or several groups -OR ", -COOR", halogen, -NR "R"; or by an aryl group, preferably a phenyl, optionally functionalized by one or more groups -OR ", -COOR", halogen or -NR "R"; preferably R 'represents a hydrogen atom, methyl, ethyl, butyl, propyl, isopropyl; and,
R" représente un atome d'hydrogène, une chaîne alkyle, de préférence en C1-C6, saturée ou insaturée, linéaires ou ramifiées ou cycliques, de préférence R" représente un atome d'hydrogène, un méthyle, un éthyle, un butyle, un propyle, un isopropyle ;R "represents a hydrogen atom, an alkyl chain, preferably C1-C6, saturated or unsaturated, linear or branched or cyclic, preferably R" represents a hydrogen atom, a methyl, an ethyl, a butyl, propyl, isopropyl;
étant entendu que dans chacun des groupes -NR'R' et -NR"R", les substituants R', respectivement R", sont identiques ou différents, et que avantageusement le groupe -NR'R' représente un acide aminé, de préférence choisi parmi la L-alanine, la L-arginine, la L-asparagine, acide L-aspartique, la L-cystéine, la L-glutamine, acide L-glutamique, la glycine, la L-histidine, la L-isoleucine, la L-leucine, la L- lysine, la L-méthionine, la L-phénylalanine, la L-proline, la L-sérine, la L-thréonine, le L-tryptophane, la L-tyrosine, la L-valine ;it being understood that in each of the groups -NR'R 'and -NR "R", the substituents R', respectively R ", are identical or different, and that advantageously the group -NR'R 'represents an amino acid, preferably chosen from L-alanine, L-arginine, L-asparagine, L-aspartic acid, L-cysteine, L-glutamine, L-glutamic acid, glycine, L-histidine, L-isoleucine, L-leucine, L-lysine, L-methionine, L-phenylalanine, L-proline, L-serine, L-threonine, L-tryptophan, L-tyrosine, L-valine;
- R2 et R3 représentent ensemble un groupe céto (=O) ou, lorsque R2 représente un atome d'hydrogène, R3 représente un radical OR4 avec R4 ayant les mêmes définitions que celles données précédemment pour R1.- R2 and R3 together represent a keto group (= O) or, when R2 represents a hydrogen atom, R3 represents an OR4 radical with R4 having the same definitions as those given above for R1.
L'invention concerne également les isomères optiques et/ou géométriques des dérivés de la DHEA de formule (I) seule ou en mélange en toutes proportions, ainsi que les sels physiologiquement acceptables de ces dérivés. En particulier, la stéréochimie en position 7 des dérivés de la DHEA de formule (I) pour lesquels R3 représente un radical OR4 peut être alpha (α), béta (β) ou le mélange des deux en toute proportion.The invention also relates to the optical and / or geometric isomers of the DHEA derivatives of formula (I) alone or as a mixture in all proportions, as well as the physiologically acceptable salts of these derivatives. In particular, the stereochemistry in position 7 of the DHEA derivatives of formula (I) for which R3 represents an OR4 radical can be alpha (α), beta (β) or the mixture of the two in any proportion.
Selon une forme préférée de l'invention, les dérivés de la DHEA de formule (I) préférés sont ceux pour lesquels R2 et R3 représentent ensemble un groupe céto (=O) et R1 représente un atome hydrogène ou un groupe alkyle en C1-C24, de préférence en C1- C18, saturé ou insaturé, linéaire ou ramifié, ou cyclique pouvant contenir un ou plusieurs heteroatomes, et éventuellement substitué par un ou plusieurs groupes choisis parmi -OR' et/ou -SR' et/ou -COOR' et/ou -NR'R' et/ou halogène.According to a preferred form of the invention, the preferred DHEA derivatives of formula (I) are those for which R2 and R3 together represent a keto group (= O) and R1 represents a hydrogen atom or a C1-C24 alkyl group , preferably C1-C18, saturated or unsaturated, linear or branched, or cyclic which may contain one or more heteroatoms, and optionally substituted by one or more groups chosen from -OR 'and / or -SR' and / or -COOR ' and / or -NR'R 'and / or halogen.
Selon une autre forme préférée de l'invention, les dérivés de la DHEA de formule (I) préférés sont ceux pour lesquels R2 et R3 représentent ensemble un groupe céto (=O) et R1 représente un groupe alkylcarbonyle, dont la partie alkyle en C1-C24, de préférence en C1-C18, est saturée ou insaturée, linéaire ou ramifié ou cyclique et éventuellement substituée par un ou plusieurs groupes choisis parmi -OR' et/ou -SR' et/ou -COOR' et/ou -NR'R' et/ou halogène.According to another preferred form of the invention, the preferred DHEA derivatives of formula (I) are those for which R2 and R3 together represent a keto group (= O) and R1 represents an alkylcarbonyl group, including the C1 alkyl part -C24, preferably C1-C18, is saturated or unsaturated, linear or branched or cyclic and optionally substituted by one or more groups chosen from -OR 'and / or -SR' and / or -COOR 'and / or -NR 'R' and / or halogen.
Selon encore une autre forme préférée de l'invention les dérivés de la DHEA de formule (I) préférés sont ceux pour lesquels R2 représente un atome d'hydrogène, R3 représente un radical OR4, avec R4 ayant les mêmes définitions que celles données précédemment de manière préférée pour R1.According to yet another preferred form of the invention, the preferred DHEA derivatives of formula (I) are those for which R2 represents a hydrogen atom, R3 represents a radical OR4, with R4 having the same definitions as those given above of preferred way for R1.
Parmi les dérivés de la DHEA de formule (I) selon l'invention, on préfère tout particulièrement au moins l'un des composés suivants :Among the DHEA derivatives of formula (I) according to the invention, any particularly at least one of the following compounds:
- Δ5-androstène-3β-hydroxy-7,17-dione ou 7-oxo-déhydroépiandrostérone (7-oxo- DHEA) ;- Δ5-androstene-3β-hydroxy-7,17-dione or 7-oxo-dehydroepiandrosterone (7-oxo-DHEA);
- 3β-O-acétyl-7-oxo-déhydroépiandrostérone (ou 3β-acétyloxy-7-oxo-DHEA commercialisée sous le nom de 7 Keto par la société Humanetics);- 3β-O-acetyl-7-oxo-dehydroepiandrosterone (or 3β-acetyloxy-7-oxo-DHEA sold under the name of 7 Keto by the company Humanetics);
- 3β-O-propionyl-7-oxo-déhydroépiandrostérone (ou 3β-propionyloxy-7-oxo-DHEA) ;- 3β-O-propionyl-7-oxo-dehydroepiandrosterone (or 3β-propionyloxy-7-oxo-DHEA);
- 3β-O-butanoyl-7-oxo-déhydroépiandrostérone (ou 3β-butanoyloxy-7-oxo-DHEA) ;- 3β-O-butanoyl-7-oxo-dehydroepiandrosterone (or 3β-butanoyloxy-7-oxo-DHEA);
- 3β-O-iso-butanoyl-7-oxo-déhydroépiandrostérone ;- 3β-O-iso-butanoyl-7-oxo-dehydroepiandrosterone;
- 3β-O-pentanoyl-7-oxo-déhydroépiandrostérone ; - 3β-O-hexanoyl-7-oxo-déhydroépiandrostérone ;- 3β-O-pentanoyl-7-oxo-dehydroepiandrosterone; - 3β-O-hexanoyl-7-oxo-dehydroepiandrosterone;
- 3β-O-héptanoyl-7-oxo-déhydroépiandrostérone ; 3β-O-octanoyl-7-oxo-déhydroépiandrostérone ; 3β-O-nonanoyl-7-oxo-déhydroépiandrostérone ; 3β-O-décanoyl-7-oxo-déhydroépiandrostérone ; - 3β-O-dodécanoyl-7-oxo-déhydroépiandrostérone ;- 3β-O-heptanoyl-7-oxo-dehydroepiandrosterone; 3β-O-octanoyl-7-oxo-dehydroepiandrosterone; 3β-O-nonanoyl-7-oxo-dehydroepiandrosterone; 3β-O-decanoyl-7-oxo-dehydroepiandrosterone; - 3β-O-dodecanoyl-7-oxo-dehydroepiandrosterone;
3β-O-myristoyl-7-oxo-déhydroépiandrostérone ;3β-O-myristoyl-7-oxo-dehydroepiandrosterone;
3β-O-palmitoyl-7-oxo-déhydroépiandrostérone ;3β-O-palmitoyl-7-oxo-dehydroepiandrosterone;
3β-O-stéaroyl-7-oxo-déhydroépiandrostérone ;3β-O-stearoyl-7-oxo-dehydroepiandrosterone;
3β-O-arachidoyl-7-oxo-déhydroépiandrostérone ; - 3β-O-docosanoyl-7-oxo-déhydroépiandrostérone ;3β-O-arachidoyl-7-oxo-dehydroepiandrosterone; - 3β-O-docosanoyl-7-oxo-dehydroepiandrosterone;
- 3β-O-lignoceroyl-7-oxo-déhydroépiandrostérone ;- 3β-O-lignoceroyl-7-oxo-dehydroepiandrosterone;
- 3β-O-oléoyl-7-oxo-déhydroépiandrostérone ;- 3β-O-oleoyl-7-oxo-dehydroepiandrosterone;
- 3β-O-linoléoyl-7-oxo-déhydroépiandrostérone ;- 3β-O-linoleoyl-7-oxo-dehydroepiandrosterone;
- 3β-O-linolénoyl-7-oxo-déhydroépiandrostérone ; - 3β-O-pétroselinoyl-7-oxo-déhydroépiandrostérone ;- 3β-O-linolenoyl-7-oxo-dehydroepiandrosterone; - 3β-O-petroselinoyl-7-oxo-dehydroepiandrosterone;
- 3β-O-méthyl-7-oxo-déhydroépiandrostérone ;- 3β-O-methyl-7-oxo-dehydroepiandrosterone;
- 3β-O-éthyl-7-oxo-déhydroépiandrostérone ;- 3β-O-ethyl-7-oxo-dehydroepiandrosterone;
- 3β-O-carboxyméthyl-7-oxo-déhydroépiandrostérone :- 3β-O-carboxymethyl-7-oxo-dehydroepiandrosterone:
- 3β-O-glucosyl-7-oxo-déhydroépiandrostérone ; - 3β-O-glucoronyl-7-oxo-déhydroépiandrostérone ;- 3β-O-glucosyl-7-oxo-dehydroepiandrosterone; - 3β-O-glucoronyl-7-oxo-dehydroepiandrosterone;
- 3β-O-(2-tétrahydropyranyl)-7-oxo-déhydroépiandrostérone ;- 3β-O- (2-tetrahydropyranyl) -7-oxo-dehydroepiandrosterone;
- 3β-O-(2-tétrahydrofuranyl)-7-oxo-déhydroépiandrostérone ;- 3β-O- (2-tetrahydrofuranyl) -7-oxo-dehydroepiandrosterone;
- Glycinate de 3β-O-7-oxo-déhydroépiandrostérone ; - Lysinate de 3β-O-7-oxo-déhydroépiandrostérone ;- 3β-O-7-oxo-dehydroepiandrosterone glycinate; - 3β-O-7-oxo-dehydroepiandrosterone lysinate;
- Sérinate de 3β-O-7-oxo-déhydroépiandrostérone ;- 3β-O-7-oxo-dehydroepiandrosterone serinate;
- α-Glutamate de 3β-O-7-oxo-déhydroépiandrostérone ;- 3β-O-7-oxo-dehydroepiandrosterone α-glutamate;
- α-Aspartate de 3β-O-7-oxo-déhydroépiandrostérone ; - 3β-Hemisuccinoyloxyandrost-5-ene-7,17-dione ;- α-Aspartate of 3β-O-7-oxo-dehydroepiandrosterone; - 3β-Hemisuccinoyloxyandrost-5-ene-7,17-dione;
- 3β-O-(2-hydroxy-malonyl)-7-oxo-déhydroépiandrostérone ;- 3β-O- (2-hydroxy-malonyl) -7-oxo-dehydroepiandrosterone;
- 3β-O-(2-malonyl-amino-carbonyl)-7-oxo-déhydroépiandrostérone ;- 3β-O- (2-malonyl-amino-carbonyl) -7-oxo-dehydroepiandrosterone;
- 3β-O-(2-succinyl-amino-carbonyl)-7-oxo-déhydroépiandrostérone ;- 3β-O- (2-succinyl-amino-carbonyl) -7-oxo-dehydroepiandrosterone;
- 3β-O-(2-glutaryl-amino-carbonyl)-7-oxo-déhydroépiandrostérone ; - 3β-méthylcarbonate-7-oxo-déhydroépiandrostérone ;- 3β-O- (2-glutaryl-amino-carbonyl) -7-oxo-dehydroepiandrosterone; - 3β-methylcarbonate-7-oxo-dehydroepiandrosterone;
- 3β-O-(trifluroacétyl)-7-oxo-déhydroépiandrostérone ;- 3β-O- (trifluroacetyl) -7-oxo-dehydroepiandrosterone;
- 3β-O-(4-carboxy-butanoyl)-7-oxo-déhydroépiandrostérone ;- 3β-O- (4-carboxy-butanoyl) -7-oxo-dehydroepiandrosterone;
- 3β-O-(4-cyclopentyl-butanoyl)-7-oxo-déhydroépiandrostérone ; 3β-O-benzoyl-7-oxo-déhydroépiandrostérone ; - 3β-O-(3,4-dihyroxy-benzoyl)-7-oxo-déhydroépiandrostérone ;- 3β-O- (4-cyclopentyl-butanoyl) -7-oxo-dehydroepiandrosterone; 3β-O-benzoyl-7-oxo-dehydroepiandrosterone; - 3β-O- (3,4-dihyroxy-benzoyl) -7-oxo-dehydroepiandrosterone;
3β-O-(ascorbyl-phosphate)-7-oxo-déhydroépiandrostérone ;3β-O- (ascorbyl phosphate) -7-oxo-dehydroepiandrosterone;
3β-O-(ascorbyl-sulfate)-7-oxo-déhydroépiandrostérone ;3β-O- (ascorbyl sulfate) -7-oxo-dehydroepiandrosterone;
3β-O-phosphonyl-7-oxo-déhydroépiandrostérone ;3β-O-phosphonyl-7-oxo-dehydroepiandrosterone;
3β-O-monoacétyl-phosphonyl-7-oxo-déhydroépiandrostérone ; - 3β-O-sulfonyl-7-oxo-déhydroépiandrostérone ;3β-O-monoacetyl-phosphonyl-7-oxo-dehydroepiandrosterone; - 3β-O-sulfonyl-7-oxo-dehydroepiandrosterone;
- 3β-O-(tertio-butyl-diméthyl-silyl)-7-oxo-déhydroépiandrostérone ;- 3β-O- (tert-butyl-dimethyl-silyl) -7-oxo-dehydroepiandrosterone;
- 3β-O-(tertio-butyl-diphényl-silyl)-7-oxo-déhydroépiandrostérone ;- 3β-O- (tert-butyl-diphenyl-silyl) -7-oxo-dehydroepiandrosterone;
- 3β-O-(triméthyl silyl)-7-oxo-déhydroépiandrostérone ;- 3β-O- (trimethyl silyl) -7-oxo-dehydroepiandrosterone;
- Δ5-androstène-3β,7β-dihydroxy-17-dione ou 7β-OH-déhydroépiandrostérone (7β- hydroxy-DHEA) ;- Δ5-androstene-3β, 7β-dihydroxy-17-dione or 7β-OH-dehydroepiandrosterone (7β-hydroxy-DHEA);
- Δ5-androstène-3β,7α-dihydroxy-17-dione ou 7α-OH-déhydroépiandrostérone (7α- hydroxy-DHEA) ;- Δ5-androstene-3β, 7α-dihydroxy-17-dione or 7α-OH-dehydroepiandrosterone (7α-hydroxy-DHEA);
- 3β-O-acétyl-7-hydroxy-déhydroépiandrostérone (3-béta-acétoxy-7-hydroxy-DHEA);- 3β-O-acetyl-7-hydroxy-dehydroepiandrosterone (3-beta-acetoxy-7-hydroxy-DHEA);
- 3β-O-propionyl-7-hydroxy-déhydroépiandrostérone (3-béta-propionyloxy-7- hydroxy-DHEA) ;- 3β-O-propionyl-7-hydroxy-dehydroepiandrosterone (3-beta-propionyloxy-7-hydroxy-DHEA);
- 3β-O-butanoyl-7-hydroxy-déhydroépiandrostérone (3-béta-butanoyloxy-7-hydroxy- DHEA) ;- 3β-O-butanoyl-7-hydroxy-dehydroepiandrosterone (3-beta-butanoyloxy-7-hydroxy-DHEA);
- 3β-O-iso-butanoyl-7-hydroxy-déhydroépiandrostérone ; - 3β-O-pentanoyl-7-hydroxy-déhydroépiandrostérone ;- 3β-O-iso-butanoyl-7-hydroxy-dehydroepiandrosterone; - 3β-O-pentanoyl-7-hydroxy-dehydroepiandrosterone;
- 3β-O-hexanoyl-7-hydroxy-déhydroépiandrostérone ;- 3β-O-hexanoyl-7-hydroxy-dehydroepiandrosterone;
- 3β-O-héptanoyl-7-hydroxy-déhydroépiandrostérone ;- 3β-O-heptanoyl-7-hydroxy-dehydroepiandrosterone;
- 3β-O-octanoyl-7-hydroxy-déhydroépiandrostérone ; - 3β-O-nonanoyl-7-hydroxy-déhydroépiandrostérone ;- 3β-O-octanoyl-7-hydroxy-dehydroepiandrosterone; - 3β-O-nonanoyl-7-hydroxy-dehydroepiandrosterone;
- 3β-O-décanoyl-7-hydroxy-déhydroépiandrostérone ;- 3β-O-decanoyl-7-hydroxy-dehydroepiandrosterone;
- 3β-O-dodécanoyl-7-hydroxy-déhydroépiandrostérone ; 3β-O-myristoyl-7-hydroxy-déhydroépiandrostérone ;- 3β-O-dodecanoyl-7-hydroxy-dehydroepiandrosterone; 3β-O-myristoyl-7-hydroxy-dehydroepiandrosterone;
- 3β-O-palmitoyl-7-hydroxy-déhydroépiandrostérone ; - 3β-O-stéaroyl-7-hydroxy-déhydroépiandrostérone ;- 3β-O-palmitoyl-7-hydroxy-dehydroepiandrosterone; - 3β-O-stearoyl-7-hydroxy-dehydroepiandrosterone;
- 3β-O-arachidoyl-7-hydroxy-déhydroépiandrostérone ; 3β-O-docosanoyl-7-hydroxy-déhydroépiandrostérone ; 3β-O-lignoceroyl-7-hydroxy-déhydroépiandrostérone ; 3β-O-oléoyl-7-hydroxy-déhydroépiandrostérone ; - 3β-O-linoléoyl-7-hydroxy-déhydroépiandrostérone ;- 3β-O-arachidoyl-7-hydroxy-dehydroepiandrosterone; 3β-O-docosanoyl-7-hydroxy-dehydroepiandrosterone; 3β-O-lignoceroyl-7-hydroxy-dehydroepiandrosterone; 3β-O-oleoyl-7-hydroxy-dehydroepiandrosterone; - 3β-O-linoleoyl-7-hydroxy-dehydroepiandrosterone;
3β-O-linolénoyl-7-hydroxy-déhydroépiandrostérone ;3β-O-linolenoyl-7-hydroxy-dehydroepiandrosterone;
3β-O-pétroselinoyl-7-hydroxy-déhydroépiandrostérone ;3β-O-petroselinoyl-7-hydroxy-dehydroepiandrosterone;
3β-O-acétyl-7-hydroxy-déhydroépiandrostérone ;3β-O-acetyl-7-hydroxy-dehydroepiandrosterone;
3β-O-acétyl-7-O-acétyl-déhydroépiandrostérone ; - 3β-O-acétyl-7-O-propionyl-déhydroépiandrostérone ;3β-O-acetyl-7-O-acetyl-dehydroepiandrosterone; - 3β-O-acetyl-7-O-propionyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-butanoyl-déhydroépiandrostérone ; 3β-O-acétyl-7-O-iso-butanoyl-déhydroépiandrostérone ;- 3β-O-acetyl-7-O-butanoyl-dehydroepiandrosterone; 3β-O-acetyl-7-O-iso-butanoyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-pentanoyl-déhydroépiandrostérone ;- 3β-O-acetyl-7-O-pentanoyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-hexanoyl-déhydroépiandrostérone ; - 3β-O-acétyl-7-O-héptanoyl-déhydroépiandrostérone ;- 3β-O-acetyl-7-O-hexanoyl-dehydroepiandrosterone; - 3β-O-acetyl-7-O-heptanoyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-octanoyl-déhydroépiandrostérone ;- 3β-O-acetyl-7-O-octanoyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-nonanoyl-déhydroépiandrostérone ;- 3β-O-acetyl-7-O-nonanoyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-décanoyl-déhydroépiandrostérone ;- 3β-O-acetyl-7-O-decanoyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-dodécanoyl-déhydroépiandrostérone ; - 3β-O-acétyl-7-O-myristoyl-déhydroépiandrostérone ;- 3β-O-acetyl-7-O-dodecanoyl-dehydroepiandrosterone; - 3β-O-acetyl-7-O-myristoyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-palmitoyl-déhydroépiandrostérone ;- 3β-O-acetyl-7-O-palmitoyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-stéaroyl-déhydroépiandrostérone ;- 3β-O-acetyl-7-O-stearoyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-arachidoyl-déhydroépiandrostérone ; - 3β-O-acétyl-7-O-docosanoyl-déhydroépiandrostérone ;- 3β-O-acetyl-7-O-arachidoyl-dehydroepiandrosterone; - 3β-O-acetyl-7-O-docosanoyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-lignoceroyl-déhydroépiandrostérone ;- 3β-O-acetyl-7-O-lignoceroyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-oléoyl-déhydroépiandrostérone ;- 3β-O-acetyl-7-O-oleoyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-linoléoyl-déhydroépiandrostérone ; - 3β-O-acétyl-7-O-linolénoyl-déhydroépiandrostérone ;- 3β-O-acetyl-7-O-linoleoyl-dehydroepiandrosterone; - 3β-O-acetyl-7-O-linolenoyl-dehydroepiandrosterone;
- 3β-O-acétyl-7-O-pétroselinoyl-déhydroépiandrostérone.- 3β-O-acetyl-7-O-petroselinoyl-dehydroepiandrosterone.
Avantageusement, les composés répondant à la formule (I) sont choisis parmi au moins l'un des composés suivants : - Δ5-androstène-3β-hydroxy-7,17-dione ou 7-oxo-déhydroépiandrostérone (7-oxo-Advantageously, the compounds corresponding to formula (I) are chosen from at least one of the following compounds: - Δ5-androstene-3β-hydroxy-7,17-dione or 7-oxo-dehydroepiandrosterone (7-oxo-
DHEA) ;DHEA);
3β-O-acétyl-7-oxo-déhydroépiandrostérone (ou 3β-acétoxy-7-oxo-DHEA) ;3β-O-acetyl-7-oxo-dehydroepiandrosterone (or 3β-acetoxy-7-oxo-DHEA);
- Δ5-androstène-3β,7α-dihydroxy-17-dione ou 7α-OH-déhydroépiandrostérone (7α- hydroxy-DHEA).- Δ5-androstene-3β, 7α-dihydroxy-17-dione or 7α-OH-dehydroepiandrosterone (7α-hydroxy-DHEA).
Les dérivés de la DHEA de formule (I) selon l'invention sont facilement accessibles d'un point de vue synthétique, notamment pas la mise en œuvre d'une des méthodes de synthèse décrites dans les brevets US-5,424,463 ; FR-2 771 105 ; US-5,869,709 ; US-6, 111 , 118 ou WO-94/085888.The DHEA derivatives of formula (I) according to the invention are easily accessible from a synthetic point of view, in particular not the implementation of one of the synthesis methods described in US Patents 5,424,463; FR-2,771,105; US-5,869,709; US-6, 111, 118 or WO-94/085888.
Selon l'invention, l'agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases est choisi parmi au moins l'une de substances suivantes: les triterpènes pentacycliques et les extraits de plante (notamment Glycyrrhiza glabra) en contenant, en particulier l'acide oléanolique, l'acide ursolique et ses sels, l'acide boswellique et ses sels; l'acide bétullique et ses sels; l'acide β glycyrrhétinique et ses sels et/ou ses dérivés tels que l'acide glycyrrhétique monoglucuronide, le glycyrrhétinate de stéaryle, l'acide 3-stéaroyloxy glycyrrhétique) ; - les extraits de Paeonia suffruticosa ;According to the invention, the agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases is chosen from at least one of the following substances: pentacyclic triterpenes and extracts of plant (in particular Glycyrrhiza glabra) containing it, in particular oleanolic acid, ursolic acid and its salts, boswellic acid and its salts; betullic acid and its salts; β glycyrrhetinic acid and its salts and / or its derivatives such as glycyrrhetic acid monoglucuronide, stearyl glycyrrhetinate, 3-stearoyloxy glycyrrhetic acid); - extracts of Paeonia suffruticosa;
- les extraits de Paeonia lactiflora ;- extracts of Paeonia lactiflora;
- l'huile de calophilum ; - les phycosaccharides, en particulier hydrolysed algin® ou hydrolysed algin and zinc sulfate® de la société Codif ;- calophilum oil; - phycosaccharides, in particular hydrolyzed algin ® or hydrolyzed algin and zinc sulfate ® from the company Codif;
- l'huile de Canola ;- Canola oil;
- l'huile de Tamanu ; - l'huile de calophillum ;- Tamanu oil; - calophillum oil;
- l'alphabisabolol ;- alphabisabolol;
- les extraits de camomille ;- chamomile extracts;
- Pallantoine ;- Pallantoine;
- Le diesterphosphorique de vitamine E et C, en particulier le Sépivital EPC® de Seppic ;- The diesterphosphoric acid of vitamin E and C, in particular the Sepivital EPC ® from Seppic;
- les huiles insaturées en oméga 3 telles que les huiles de rosier musca, les huiles de cassis, des huiles d'ecchium, les huiles de poisson ;- oils unsaturated in omega 3 such as oils of rose musca, blackcurrant oils, ecchium oils, fish oils;
- Les extraits de plancton, en particulier l'Oméga plancton® de Secma ;- Plankton extracts, in particular the Omega plankton ® from Secma;
- L'associatition de sodium palmitoylproline et de Nymphéa alba, en particulier le Seppicalm VG® de Séppic ;- The combination of palmitoylproline sodium and Nymphea alba, in particular Seppicalm VG ® from Séppic;
- les extraits du pygeum ;- extracts from the pygeum;
- Les extraits de Boswellia serrata, en particulier le Soothex® de Quest ;- Boswellia serrata extracts, in particular Quest Soothex ® ;
- Les extraits de Centipeda cunnighami, en particulier le phytoplenolin® de Bio- Botanica ; - Les extraits d'Hélianthus annuus, en particulier l'Hélioxine® de Silab ;- Centipeda cunnighami extracts, in particular phytoplenolin ® from Bio-Botanica; - Helianthus annuus extracts, in particular Helioxin ® from Silab;
- Les extraits de Linum usitatissimum, en particulier la Sensiline® de Silab ;- Linum usitatissimum extracts, in particular Sensiline ® from Silab;
- les tocotrienols ;- tocotrienols;
- les extraits de Cola nitida ;- extracts of Cola nitida;
- le piperonal ; - les extraits de clou de girofle ;- the piperonal; - clove extracts;
- les extraits d'épilobe (Epilobium angustifolium) ;- willowherb extracts (Epilobium angustifolium);
- les extraits d'Aloe vera.- Aloe vera extracts.
Avantageusement, l'agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases est choisi parmi au moins l'une des substances suivantes :Advantageously, the agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases is chosen from at least one of the following substances:
- les extraits de Glycyrrhiza glabra, l'acide oléanolique et ses sels; l'acide ursolique et ses sels; l'acide boswellique et ses sels; l'acide bétullique et ses sels; l'acide β glycyrrhétinique et ses sels et/ou ses dérivés tels que l'acide glycyrrhétique monoglucuronide, le glycyrrhétinate de stéaryle, l'acide 3-stéaroyloxy glycyrrhétique ;- extracts of Glycyrrhiza glabra, oleanolic acid and its salts; ursolic acid and its salts; boswellic acid and its salts; betullic acid and its salts; β glycyrrhetinic acid and its salts and / or its derivatives such as glycyrrhetic acid monoglucuronide, stearyl glycyrrhetinate, 3-stearoyloxy glycyrrhetic acid;
- les extraits de Paeonia suffruticosa ;- extracts of Paeonia suffruticosa;
- les extraits de Paeonia lactiflora ; - les phycosaccharides, en particulier hydrolysed algin® ou hydrolysed algin and zinc sulfate® de la société Codif ;- extracts of Paeonia lactiflora; - phycosaccharides, in particular hydrolyzed algin ® or hydrolyzed algin and zinc sulfate ® from the company Codif;
- l'huile de calophillum ;- calophillum oil;
- l'alphabisabolol ; les extraits de camomille ; - l'allantoine ;- alphabisabolol; chamomile extracts; - allantoin;
- les tocotrienols ; les extraits d'Aloe vera.- tocotrienols; Aloe vera extracts.
Les quantités respectives de dérivé de DHEA de formule (I) et d'agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases présentes dans la composition dépend bien évidement de l'effet recherché.The respective amounts of DHEA derivative of formula (I) and of agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases present in the composition obviously depends on the effect. research.
Pour donner un ordre de grandeur, la composition selon l'invention peut renfermer de 0,0001% à 10%) en poids, de préférence de 0,01% à 5% en poids, de dérivé de la DHEA de formule (I) tel que défini précédemment, par rapport au poids total de la composition.To give an order of magnitude, the composition according to the invention may contain from 0.0001% to 10% by weight, preferably from 0.01% to 5% by weight, of DHEA derivative of formula (I) as defined above, relative to the total weight of the composition.
Pour donner un autre ordre de grandeur, la composition selon l'invention peut renfermer de 0,0001 à 10%, de préférence de 0,001 à 5% en poids, d'agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases tel que défini précédemment, par rapport au poids total de la composition.To give another order of magnitude, the composition according to the invention may contain from 0.0001 to 10%, preferably from 0.001 to 5% by weight, of agent capable of inhibiting at least one enzyme chosen from phospholipases A2 , lipoxygenases and / or human prostaglandins synthetases as defined above, relative to the total weight of the composition.
Selon le mode d'administration, cette composition peut se présenter sous toutes les formes galéniques normalement utilisées. Les compositions selon l'invention peuvent être destinées à une application cosmétique ou pharmaceutique, particulièrement dermatologique. De préférence les compositions selon l'invention sont destinées à une application cosmétique.Depending on the mode of administration, this composition can be in all the galenical forms normally used. The compositions according to the invention can be intended for a cosmetic or pharmaceutical application, particularly dermatological. Preferably, the compositions according to the invention are intended for a cosmetic application.
Ainsi, un autre objet de l'invention se rapporte à l'utilisation cosmétique d'une composition renfermant, dans un milieu physiologiquement acceptable, au moins un dérivé de la DHEA de formule (I) tel que défini précédemment avec au moins agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases, pour apaiser la peau et/ou le cuir chevelu.Thus, another object of the invention relates to the cosmetic use of a composition containing, in a physiologically acceptable medium, at least one DHEA derivative of formula (I) as defined above with at least agent capable of 'inhibit at least one enzyme selected from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases, to soothe the skin and / or scalp.
Un autre objet de l'invention se rapporte encore à l'utilisation cosmétique d'une composition renfermant, dans un milieu physiologiquement acceptable, au moins un dérivé de la DHEA de formule (I) tel que défini précédemment avec au moins agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases, pour prévenir et/ou traiter les peaux sensibles et/ou l'inconfort cutané et/ou les tiraillements cutanés et/ou les démangeaisons cutanées et/ou les irritations cutanées et/ou les gonflements cutanés et/ou les rougeurs cutanées et/ou les sensations de chaleur cutanée.Another subject of the invention also relates to the cosmetic use of a composition containing, in a physiologically acceptable medium, at least one DHEA derivative of formula (I) as defined above with at least agent capable of inhibit at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases, to prevent and / or treat sensitive skin and / or skin discomfort and / or skin tightness and / or itching of the skin and / or skin irritations and / or skin swelling and / or skin redness and / or feelings of skin heat.
Les compositions selon l'invention sont de préférence adaptées à une application topique sur les matières kératiniques telles que la peau, le cuir chevelu, les muqueuses, les cheveux, les cils ou les ongles. Elles peuvent 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, 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 compositions according to the invention are preferably suitable for topical application to keratin materials such as the skin, the scalp, the mucous membranes, the hair, the eyelashes or the nails. They 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 emulsion, a silicone emulsion , a microemulsion or nanoemulsion, an aqueous or oily gel or a liquid, pasty or solid anhydrous product.
Ces compositions peuvent 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. Elles peuvent éventuellement être appliquées sur la peau sous forme d'aérosol, de patch ou de poudre. Elles peuvent également se présenter sous forme solide, et par exemple sous forme de stick. Elles peuvent être utilisées comme produit de soin et/ou comme produit de maquillage de la peau. Elles peuvent en variante se présenter sous forme de shampooing ou d'après-shampooing.These compositions 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. They can optionally be applied to the skin in the form of an aerosol, patch or powder. They can also be in solid form, and for example in the form of a stick. They can be used as a care product and / or as a make-up product for the skin. They may alternatively be in the form of a shampoo or conditioner.
On peut également envisager une composition sous la forme d'une mousse ou encore sous forme de compositions pour aérosol comprenant également un agent propulseur sous pression.It is also possible to envisage a composition in the form of a foam or also in the form of aerosol compositions also comprising a propellant under pressure.
De façon connue, la composition de l'invention peut contenir également les adjuvants habituels dans le domaine cosmétique, tels que les gélifiants hydrophiles ou lipophiles, les conservateurs, les antioxydants, les solvants, les parfums, les charges, les pigments, les absorbeurs d'odeur et les matières colorantes. Les quantités de ces différents adjuvants sont celles classiquement utilisées dans le domaine considéré, 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 du dérivé de DHEA de formule (I) selon l'invention et de l'agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases.In a known manner, the composition of the invention may also contain the adjuvants usual in the cosmetic field, such as hydrophilic or lipophilic gelling agents, preservatives, antioxidants, solvents, perfumes, fillers, pigments, absorbents of odor and coloring matter. The amounts of these various adjuvants are those conventionally used in the field 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 derivative of formula (I) according to the invention and of the agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases.
Lorsque la composition selon l'invention est une émulsion, la proportion de la phase grasse peut aller de 2 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. L'émulsion peut, en outre, contenir des vésicules lipidiques.When the composition according to the invention is an emulsion, the proportion of the fatty phase can range from 2 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. The emulsion may, in addition, contain lipid vesicles.
Lorsque la composition est une solution ou un gel huileux, la phase grasse peut représenter plus de 90 % du poids total de la composition.When the composition is an oily solution or gel, the fatty phase can represent more than 90% of the total weight of the composition.
De façon connue, la composition cosmétique peut contenir également des adjuvants habituels dans le domaine cosmétique, tels que les gélifiants hydrophiles ou lipophiles, les additifs hydrophiles ou lipophiles, les conservateurs, les antioxydants, les solvants, les parfums, les charges, les filtres, les absorbeurs d'odeur et les matières colorantes. Les quantités de ces différents adjuvants sont celles classiquement utilisées dans le domaine cosmétique, et par exemple de 0,01 % à 10 % du poids total de la composition. Ces adjuvants, selon leur nature, peuvent être introduits dans la phase grasse, dans la phase aqueuse et/ou dans les sphérules lipidiques.In known manner, the cosmetic composition can also contain adjuvants customary in the cosmetic field, such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic additives, preservatives, antioxidants, solvents, perfumes, fillers, filters, odor absorbers and coloring matters. The amounts of these various adjuvants are those conventionally used in the cosmetic field, and for example from 0.01% to 10% of the total weight of the composition. These adjuvants, depending on their nature, can be introduced into the fatty phase, into the aqueous phase and / or into the lipid spherules.
Comme huiles ou cires utilisables dans l'invention, on peut citer les huiles minérales (huile de vaseline), les huiles végétales (fraction liquide du beurre de karité, huile de tournesol), les huiles animales (perhydrosqualène), les huiles de synthèse (huile de Purcellin), les huiles ou cires siliconées (cyclométhicone) et les huiles fluorées (perfluoropolyéthers), les cires d'abeille, de carnauba ou paraffine. On peut ajouter à ces huiles des alcools gras et des acides gras (acide stéarique).As oils or waxes which can be used in the invention, mention may be made of mineral oils (petroleum jelly oil), vegetable oils (liquid fraction of shea butter, sunflower oil), animal oils (perhydrosqualene), synthetic oils ( Purcellin oil), silicone oils or waxes (cyclomethicone) and fluorinated oils (perfluoropolyethers), beeswax, carnauba or paraffin. Fatty alcohols and fatty acids (stearic acid) can be added to these oils.
Comme emulsionnants et coemulsionnants 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 tristéarate 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; fatty acid and polyol 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 solvants utilisables dans l'invention, on peut citer les alcools inférieurs, notamment l'éthanol et l'isopropanol, le propylène glycol.As solvents which can be used in the invention, mention may be made of lower alcohols, in particular ethanol and isopropanol, propylene glycol.
Comme gélifiants hydrophiles utilisables dans l'invention, on peut citer les polymères carboxyvinyliques (carbomer), les copolymères acryliques tels que les copolymères d'acrylates/alkylacrylates, les polyacrylamides, les polysaccharides tels que l'hydroxypropylcellulose, 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 comme les stéarates d'aluminium et la silice hydrophobe, éthylcellulose, polyéthylène.As hydrophilic gelling agents which can be used in the invention, mention may be made of carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkyl acrylate copolymers, polyacrylamides, polysaccharides such as hydroxypropylcellulose, natural gums and clays, and, as lipophilic gelling agents, mention may be made of modified clays such as bentones, metal salts of fatty acids such as aluminum stearates and hydrophobic silica, ethylcellulose, polyethylene.
Quel que soit son mode d'administration, l'association selon l'invention peut être utilisée en cosmétique pour apaiser la peau et/ou le cuir chevelu. Ainsi, un autre objet de la présente invention se rapporte à l'utilisation cosmétique en tant qu'agent apaisant, par application topique sur la peau et/ou le cuir chevelu, de l'association comprenant au moins un dérivé de la DHEA de formule (I) tel que défini précédemment avec au moins agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases tel que défini précédemment.Whatever its mode of administration, the combination according to the invention can be used in cosmetics to soothe the skin and / or the scalp. Thus, another object of the present invention relates to cosmetic use as a soothing agent, by topical application to the skin and / or the scalp, of the combination comprising at least one DHEA derivative of formula (I) as defined above with at least one agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases as defined above.
La présente invention se rapporte encore à l'utilisation cosmétique en tant qu'agent pour prévenir et/ou traiter les peaux sensibles, l'inconfort cutané, les tiraillements cutanés, les démangeaisons cutanées, les irritations cutanées, les gonflements cutanés, les rougeurs cutanées et/ou les sensations de chaleur cutanée, par application topique sur la peau et/ou le cuir, de l'association comprenant au moins un dérivé de la DHEA de formule (I) tel que défini précédemment avec au moins agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases tel que défini précédemment.The present invention also relates to cosmetic use as an agent for preventing and / or treating sensitive skin, skin discomfort, skin tightness, itchy skin, skin irritation, skin swelling, skin rash and / or the sensations of skin heat, by topical application to the skin and / or leather, of the combination comprising at least one DHEA derivative of formula (I) as defined above with at least agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases as defined above.
Par "peaux sensibles", on entend les peaux qui ont été caractérisées par la Demanderesse dans le brevet EP 0 680 749 B1. La Demanderesse a pu montrer que les symptômes liés aux peaux sensibles étaient constitués de sensations plus ou moins douloureuses ressenties dans une zone cutanée, tels que des picotements, fourmillements, démangeaisons ou prurits, brûlures, rougeurs, échauffements, inconforts, tiraillements, etc. Ces symptômes peuvent se manifester en réponse à différents facteurs tels que entre autres, la sueur, les frottements, les émotions, les aliments, le vent, les frottements, le rasoir, le savon, les tensioactifs, l'eau dure à forte concentration de calcaire, les variations de température ou la laine.By "sensitive skins" is meant the skins which have been characterized by the Applicant in patent EP 0 680 749 B1. The Applicant has been able to show that the symptoms linked to sensitive skin consist of more or less painful sensations felt in a skin area, such as tingling, tingling, itching or itching, burning, redness, heating, discomfort, tightness, etc. These symptoms can appear in response to various factors such as, among others, sweat, friction, emotions, food, wind, friction, razor, soap, surfactants, hard water with a high concentration of limestone, temperature variations or wool.
Par ailleurs, l'expression "peaux sensibles" recouvre à la fois les peaux irritables et les peaux intolérantes.Furthermore, the expression "sensitive skin" covers both irritable skin and intolerant skin.
La présente invention se rapporte encore à un procédé de traitement cosmétique apaisant des matières kératiniques comprenant l'application topique sur celles-ci d'une composition renfermant, dans un milieu physiologiquement acceptable, au moins un dérivé de la DHEA de formule (I) tel que défini précédemment avec au moins agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases.The present invention also relates to a soothing cosmetic treatment process for keratin materials comprising the topical application thereon of a composition containing, in a physiologically acceptable medium, at least one DHEA derivative of formula (I) such as defined previously with at least agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases.
Elle se rapporte plus particulièrement à un procédé de traitement cosmétique des peaux sensibles, de l'inconfort cutané, des tiraillements cutanés, des démangeaisons cutanées, des irritations cutanées, des gonflements cutanés, des rougeurs cutanées, des sensations de chaleur cutanée comprenant l'application topique sur la peau ou le cuir chevelu d'une composition renfermant, dans un milieu physiologiquement acceptable, au moins un dérivé de la DHEA de formule (I) tel que défini précédemment en association avec au moins agent capable d'inhiber au moins une enzyme choisie parmi les phospholipases A2, les lipoxygénases et/ou les prostaglandines humaines synthetases.It relates more particularly to a cosmetic treatment process for sensitive skin, skin discomfort, skin tightness, itching of the skin, skin irritations, swelling of the skin, redness of the skin, sensations of skin heat comprising the application topical on the skin or scalp of a composition containing, in a physiologically acceptable medium, at least one DHEA derivative of formula (I) as defined above in combination with at least agent capable of inhibiting at least one enzyme chosen from phospholipases A2, lipoxygenases and / or human prostaglandins synthetases.
Les exemples de compositions suivants illustrent l'invention sans la limiter aucunement. Dans les compositions, les proportions indiquées sont des pourcentages en poids, sauf indication contraire.The following examples of compositions illustrate the invention without limiting it in any way. In the compositions, the proportions indicated are percentages by weight, unless otherwise indicated.
Exemple 1 : Gel pour peaux sensiblesEXAMPLE 1 Gel for Sensitive Skin
A Copolymère acrylate / C10-30 alkylacrylate 0,50%A Acrylate / C10-30 alkylacrylate copolymer 0.50%
Eau 12,00%Water 12.00%
B Hexyldécanol 10,00%B Hexyldecanol 10.00%
Isononanoate d'isononyle 10,00 %Isononyl isononanoate 10.00%
Octyl methoxycinnamate 1 ,00 % 7-Kéto-DHEA 0,50%Octyl methoxycinnamate 1.00% 7-Keto-DHEA 0.50%
C Triethanolamine 0,50%C Triethanolamine 0.50%
Eau Qsp 100,00%Water Qs 100.00%
Glycérine 6,00%Glycerin 6.00%
Conservateurs 0,25 % Allantoine 0,10% α-bisabolol 0,10%Preservatives 0.25% Allantoin 0.10% α-bisabolol 0.10%
D Polyacrylamide et C13-14 isoparaffin et Laureth 7D Polyacrylamide and C13-14 isoparaffin and Laureth 7
(Sepigel 305 fourni par la société SEPPIC) 0,50 % Mode opératoire :(Sepigel 305 supplied by SEPPIC) 0.50% Procedure:
La composition ci-dessus peut être préparée de la manière suivante : le polymère de la phase A est dispersé dans l'eau à 40°C. Les constituants de la phase B sont chauffés à 70°C jusqu'à dissolution complète puis la température est ramenée à 40°C. Les constituants de la phase C sont mélangés à 50°C. 'The above composition can be prepared in the following manner: the polymer of phase A is dispersed in water at 40 ° C. The constituents of phase B are heated to 70 ° C until complete dissolution and then the temperature is reduced to 40 ° C. The constituents of phase C are mixed at 50 ° C. '
B est introduite dans A à 40°C sous agitation puis la phase C leur est ajoutée. La phase D est introduite dans le mélange précédemment obtenu.B is introduced into A at 40 ° C with stirring and then phase C is added to them. Phase D is introduced into the mixture previously obtained.
Cette crème est particulièrement bien adaptée au traitement des peaux sensibles en application mono ou bi quotidienne.This cream is particularly well suited to the treatment of sensitive skin in single or bi daily application.
Exemple 2 : lotion pour peau sensibleEXAMPLE 2 Lotion for Sensitive Skin
- Extrait de Paeonia suffruticosa 0,50%- Paeonia suffruticosa extract 0.50%
- 3β-acétoxy-7-céto-DHEA 0,01% - Propylène glycol 20,00%- 3β-acetoxy-7-keto-DHEA 0.01% - Propylene glycol 20.00%
- Hydroxy propycellulose 3,50%- Hydroxy propycellulose 3.50%
- Alcool éthylique Qsp 100,00 % - Eau 50,00%- Ethyl alcohol Qsp 100.00% - Water 50.00%
Exemple 3 : Gel de nettoyage pour peaux sensiblesExample 3: Cleansing gel for sensitive skin
Tous les pourcentages sont exprimés en poids de matières premières telles quelles.All percentages are expressed by weight of raw materials as such.
- Lauryl phosphate (1) 6,50%- Lauryl phosphate (1) 6.50%
- Decyl Glucoside (2) 16,25 % - Polyquaternium-7 (3) 5,70%- Decyl Glucoside (2) 16.25% - Polyquaternium-7 (3) 5.70%
- PEG-150 Pentaerythrityl Tetrastearte (4) 0,50 % - Glycerin 3,50% - Sorbitol 3,50%- PEG-150 Pentaerythrityl Tetrastearte (4) 0.50% - Glycerin 3.50% - Sorbitol 3.50%
- potassium Hydroxyde 1 ,70% - Hydroxypropylcellulose 0,20%- potassium Hydroxide 1.70% - Hydroxypropylcellulose 0.20%
- Disodium EDTA 0,05%- Disodium EDTA 0.05%
- Sodium chloride 0,10%- Sodium chloride 0.10%
- 7-Kéto-DHEA 0,10%>- 7-Keto-DHEA 0.10%>
- Acide β Glycyrrhétinique 1 ,00 % - Methylparaben 0,15%- β Glycyrrhetinic acid 1, 00% - Methylparaben 0.15%
- imidazolidinyl urea 0,15% - Eau Qsp 100,00%- imidazolidinyl urea 0.15% - Water Qsp 100.00%
(1) Mono-phosphate de Lauryle (mono-ester 75 %); MAP 20® de KAO CHEMICALS(1) Lauryle mono-phosphate (75% mono-ester); MAP 20 ® by KAO CHEMICALS
(2) Alkyl (C9/11) polyglucoside (1 ,4) en solution à 40% ; Mydol 10® de KAO CHEMICALS(2) Alkyl (C9 / 11) polyglucoside (1, 4) in 40% solution; Mydol 10 ® by KAO CHEMICALS
(3) Copolymère chlorure de di-méthyl di-allyl ammonium/ acrylamide dans l'eau à 8% ; Merquat S® de CALGON(3) Copolymer of di-methyl di-allyl ammonium chloride / acrylamide in water at 8%; CALGON Merquat S ®
(4) Tétrastéarate de pentaerythrityle oxyéthylène (150 OE) CROTHIX® de CRODA(4) Pentaerythrityl oxyethylene tetrastearate (150 EO) CROTHIX ® from CRODA
Exemple 4 : Crème teintée destinée au traitement de la peau grasse et sensible - Lécithine hydrogénée 2,4 %EXAMPLE 4 Tinted Cream intended for the treatment of oily and sensitive skin - Hydrogenated lecithin 2.4%
- Huile d'amandes d'abricot 6,0 %- Apricot almond oil 6.0%
- Huile de pépin de rosier musca 1 ,0 %- Musca rose seed oil 1.0%
- Copolymère diméthacrylate d'éthylèneglycol/méthacrylate de lauryle 1 ,0 %- Ethylene glycol dimethacrylate / lauryl methacrylate copolymer 1.0%
- Stérols de soja oxyéthylénés (5 OE) 1 ,6 % - 7 alpha hydroxy-DHEA 0,5 %- Soy sterols oxyethylenated (5 EO) 1.6% - 7 alpha hydroxy-DHEA 0.5%
- Serenoa repens 1 ,0 %- Serenoa repens 1.0%
- Oxydes de fer 0,9 %- Iron oxides 0.9%
- Oxyde de titane 5,0 %- Titanium oxide 5.0%
- Polyacrylamide / C13-C14-lsoparaffine / Laureth-7 (Sepigel 305) 4,0 % - Cyclopentadiméthylsiloxane 6,0 %- Polyacrylamide / C 13 -C 14 -lsoparaffin / Laureth-7 (Sepigel 305) 4.0% - Cyclopentadimethylsiloxane 6.0%
- Glycérine 6,0 %- Glycerin 6.0%
- Propylène glycol 6,0 %% - Aloes vera 1 ,0 %- Propylene glycol 6.0 %% - Aloes vera 1, 0%
- Parfum qs - Eau déminéralisée Qsp 100,0 %- Perfume qs - Demineralized water Qsp 100.0%
Cette crème est de couleur beige et convient pour le traitement de la peau, par application sur le visage deux fois par jour. This cream is beige in color and suitable for the treatment of the skin, by application to the face twice a day.
Claims
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0113816A FR2831440B1 (en) | 2001-10-25 | 2001-10-25 | COSMETIC COMPOSITION CONTAINING A DHEA DERIVATIVE AND A SOOTHING AGENT |
| FR01/13816 | 2001-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2003035023A1 true WO2003035023A1 (en) | 2003-05-01 |
Family
ID=8868720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FR2002/003510 Ceased WO2003035023A1 (en) | 2001-10-25 | 2002-10-14 | Cosmetic composition containing a dhea derivative and a soothing agent |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2831440B1 (en) |
| WO (1) | WO2003035023A1 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003104254A3 (en) * | 2002-06-06 | 2004-05-06 | Forbes Medi Tech Inc | NOVEL ANDROSTANE AND ANDROSTENE DERIVATIVES WITH ASCORBIC ACID AND THEIR USE IN THE TREATMENT OR PREVENTION OF DIFFERENT CONDITIONS, DISEASES AND DISORDERS |
| US6930192B2 (en) | 2001-02-14 | 2005-08-16 | L'oreal | Methods for preparing 7alpha-hydroxy-dehydroepiandrosterone |
| US6964954B2 (en) | 2001-10-25 | 2005-11-15 | L'oreal | Use of DHEA derivatives on keratinous substances |
| WO2007118830A1 (en) | 2006-04-13 | 2007-10-25 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Azaheterocyclyl derivatives of androstanes and androstenes as medicaments for cardiovascular disorders |
| CN100434089C (en) * | 2006-08-22 | 2008-11-19 | 湖北中医学院 | Application of geese not herbivorous volatile oil in the preparation of inhibitors of tumor growth and proliferation |
| US7544714B2 (en) | 2004-07-16 | 2009-06-09 | University Of Massachusetts | Lipid-amino acid conjugates and methods of use |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7851477B2 (en) | 2003-05-22 | 2010-12-14 | L'oreal | Method for the treatment of skin |
| FR2855050B1 (en) * | 2003-05-22 | 2008-07-04 | Oreal | PROCESS FOR THE COSMETIC TREATMENT OF REDNESS |
| FR3099702B1 (en) | 2019-08-08 | 2022-03-25 | BASF Beauty Care Solutions FR | New cosmetic use of an extract of Epilobium angustifolium |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5823612A (en) * | 1981-08-04 | 1983-02-12 | Osaka Chem Lab | Cosmetic composition containing crude drug component |
| SE453724B (en) * | 1985-04-18 | 1988-02-29 | Nobel Consumer Goods Ab | Skin care prepn. |
| JPH09157172A (en) * | 1995-12-13 | 1997-06-17 | Lion Corp | Topical skin and eczema |
| WO1998005338A2 (en) * | 1996-08-01 | 1998-02-12 | University Of Utah Research Foundation | Use of a dehydroepiandrosterone derivative for enhancing or accelerating re-epithelialization or re-endothelialization of a tissue |
| WO1998040074A1 (en) * | 1997-03-10 | 1998-09-17 | Vitasterol (S.A.R.L.) | Cosmetic or dermatological use of 7-hydroxylated steroids |
| JP2000063224A (en) * | 1998-08-20 | 2000-02-29 | Kanebo Ltd | Cosmetic |
| WO2002047644A1 (en) * | 2000-12-15 | 2002-06-20 | L'oreal | COMPOSITION COMPRISING 7-HYDROXY DHEA AND/OR 7-KETO DHEA AND AT LEAST A 5α-REDUCTASE INHIBITOR |
-
2001
- 2001-10-25 FR FR0113816A patent/FR2831440B1/en not_active Expired - Fee Related
-
2002
- 2002-10-14 WO PCT/FR2002/003510 patent/WO2003035023A1/en not_active Ceased
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5823612A (en) * | 1981-08-04 | 1983-02-12 | Osaka Chem Lab | Cosmetic composition containing crude drug component |
| SE453724B (en) * | 1985-04-18 | 1988-02-29 | Nobel Consumer Goods Ab | Skin care prepn. |
| JPH09157172A (en) * | 1995-12-13 | 1997-06-17 | Lion Corp | Topical skin and eczema |
| WO1998005338A2 (en) * | 1996-08-01 | 1998-02-12 | University Of Utah Research Foundation | Use of a dehydroepiandrosterone derivative for enhancing or accelerating re-epithelialization or re-endothelialization of a tissue |
| WO1998040074A1 (en) * | 1997-03-10 | 1998-09-17 | Vitasterol (S.A.R.L.) | Cosmetic or dermatological use of 7-hydroxylated steroids |
| JP2000063224A (en) * | 1998-08-20 | 2000-02-29 | Kanebo Ltd | Cosmetic |
| WO2002047644A1 (en) * | 2000-12-15 | 2002-06-20 | L'oreal | COMPOSITION COMPRISING 7-HYDROXY DHEA AND/OR 7-KETO DHEA AND AT LEAST A 5α-REDUCTASE INHIBITOR |
Non-Patent Citations (4)
| Title |
|---|
| DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002214507, retrieved from STN Database accession no. 1989:13391 * |
| DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002214508, retrieved from STN Database accession no. 1983:149462 * |
| DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002214509, retrieved from STN Database accession no. 1997:435388 * |
| DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002214510, retrieved from STN Database accession no. 2000:136239 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6930192B2 (en) | 2001-02-14 | 2005-08-16 | L'oreal | Methods for preparing 7alpha-hydroxy-dehydroepiandrosterone |
| US6964954B2 (en) | 2001-10-25 | 2005-11-15 | L'oreal | Use of DHEA derivatives on keratinous substances |
| WO2003104254A3 (en) * | 2002-06-06 | 2004-05-06 | Forbes Medi Tech Inc | NOVEL ANDROSTANE AND ANDROSTENE DERIVATIVES WITH ASCORBIC ACID AND THEIR USE IN THE TREATMENT OR PREVENTION OF DIFFERENT CONDITIONS, DISEASES AND DISORDERS |
| US7544714B2 (en) | 2004-07-16 | 2009-06-09 | University Of Massachusetts | Lipid-amino acid conjugates and methods of use |
| WO2007118830A1 (en) | 2006-04-13 | 2007-10-25 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Azaheterocyclyl derivatives of androstanes and androstenes as medicaments for cardiovascular disorders |
| CN100434089C (en) * | 2006-08-22 | 2008-11-19 | 湖北中医学院 | Application of geese not herbivorous volatile oil in the preparation of inhibitors of tumor growth and proliferation |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2831440B1 (en) | 2003-12-26 |
| FR2831440A1 (en) | 2003-05-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0812184B1 (en) | Nitric oxide synthase inhibitors | |
| EP1064931B1 (en) | Cosmetic composition containing at least one hydroxystilbene and ascorbic acid | |
| CA2174598C (en) | Use of an inhibitor of an hmg-coenzyme-a reductase to prevent aging of the skin or to stimulate the process of epidermal renewal | |
| EP1252882B1 (en) | Process to increase the threshold tolerance of the sensitive skin | |
| CA2255229C (en) | Use of cinnamic acid, or of its derivatives, as a firming agent in a cosmetic composition | |
| FR2777186A1 (en) | Compositions for stimulating collagen synthesis and/or skin fibroblast proliferation, especially for cosmetic use | |
| EP1090629A1 (en) | Aescin and dextran sulfate association | |
| FR2740339A1 (en) | USE OF AT LEAST ONE NO-SYNTHASE INHIBITOR IN THE TREATMENT OF SENSITIVE SKIN | |
| EP1337234A1 (en) | Use of 2-oxothiazolidine 4-carboxylic acid derivatives as agents promoting skin peeling | |
| FR2831441A1 (en) | COSMETIC USE OF DHEA DERIVATIVES | |
| EP0904777B1 (en) | Use of an inhibitor of excitatory amino acids in cosmetic or dermatological compositions for sensitive skin and composition obtained | |
| EP0756862A1 (en) | Use of bradykinine antagonist in a cosmetic, pharmaceutical or dermatological composition and the composition obtained | |
| FR2848844A1 (en) | Use of alkyl ether of hydroxystilbene for preparation of cosmetic composition to treat disorders associated with oligoseborrhoeic dry skin e.g. dermatitis | |
| WO2003035023A1 (en) | Cosmetic composition containing a dhea derivative and a soothing agent | |
| WO2002039975A1 (en) | Use of at least a sulphonic amino derivative in a composition promoting skin peeling | |
| FR2839449A1 (en) | USE OF AT LEAST ONE METAL COMPLEX AS A DEQUAMANT | |
| EP1413291B1 (en) | Use of 5-Cholesten-3 beta,25-diol-7-one for the treatment of dry skin or scalp | |
| FR2837704A1 (en) | Use of sapogenins or compositions or natural extracts containing them to treat dry skin or scalp or associated disorders | |
| FR2850579A1 (en) | USE OF MONO-OR DI-ESTERS OF CINNAMIC ACID OR ONE OF ITS DERIVATIVES AND VITAMIN C, AS NO DONOR | |
| FR2850578A1 (en) | USE OF N-ARYLMETHYLENE ETHYLENEDIAMINETRIACETATES, N-ARYLMETHYLENEIMINODIACETATES OR N, N'-DIARYLMETHYLENE ETHYLENEDIAMINEACETATES AS NO DONORS | |
| CA2467734A1 (en) | Composition based on diosgenin ester for topical use | |
| FR2840216A1 (en) | USE OF A DHEA 7-OXIDE DERIVATIVE FOR THE TREATMENT OF DRY SKIN | |
| WO2002005779A1 (en) | Composition, in particular cosmetic, containing dhea and/or its precursors or derivatives, and a vitamin | |
| FR2801508A1 (en) | Topical compositions contain a HMG CoA-reductase inhibitor and a compound that completes its effect, for treatment of seborrhea and associated dermatoses | |
| WO2002034228A1 (en) | Cosmetic composition comprising dhea and at least a muscle relaxant |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
| AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LU MC NL PT SE SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
| DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
| 122 | Ep: pct application non-entry in european phase | ||
| NENP | Non-entry into the national phase |
Ref country code: JP |
|
| WWW | Wipo information: withdrawn in national office |
Country of ref document: JP |