WO2024126794A1 - Utilisation cosmétique d'une composition pour le soin des matières kératiniques comprenant au moins de l'acide indole-3-pyruvique - Google Patents

Utilisation cosmétique d'une composition pour le soin des matières kératiniques comprenant au moins de l'acide indole-3-pyruvique Download PDF

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Publication number
WO2024126794A1
WO2024126794A1 PCT/EP2023/086063 EP2023086063W WO2024126794A1 WO 2024126794 A1 WO2024126794 A1 WO 2024126794A1 EP 2023086063 W EP2023086063 W EP 2023086063W WO 2024126794 A1 WO2024126794 A1 WO 2024126794A1
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Prior art keywords
skin
composition
indole
pyruvic acid
salt
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PCT/EP2023/086063
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English (en)
Inventor
Amélie PREVOT-GUEGUINIAT
Magali MOREAU
Amina BOUSLIMANI
Okan ALTUNCU
Samira TAMOUTOUNOUR
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L'oreal
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Publication of WO2024126794A1 publication Critical patent/WO2024126794A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/08—Antiseborrheics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/007—Preparations for dry skin

Definitions

  • the present invention relates to the use of indole-3-pyruvic acid for improving the skin barrier function and moisturizing the skin.
  • the present invention aims to provide the cosmetic use, notably topical non-therapeutic cosmetic use, of a composition comprising, in a physiologically acceptable medium, indole- 3 -pyruvic acid, an isomer thereof or a salt thereof, for preventing a reduction in the skin barrier function and/or reinforcing the skin barrier function in an individual, in particular of dry skin.
  • the invention further relates to the cosmetic use, notably topical cosmetic use, of such a composition for preventing and/or treating atopic dermatitis or eczema.
  • the invention also relates to the cosmetic use, notably topical non-therapeutic cosmetic use, of such a composition for preventing and/or treating a skin disorder of sensitive skin, in an individual.
  • the invention additionally relates to the cosmetic use, notably topical cosmetic use, of such a composition for preventing and/or treating pruritus and/or inflammation of the skin of an individual, in particular present in a dermatological disorder, chosen from the group constituted of atopic dermatitis or eczema, psoriasis, nodular prurigo, seborrhoeic dermatitis, acne, folliculitis and rosacea.
  • a dermatological disorder chosen from the group constituted of atopic dermatitis or eczema, psoriasis, nodular prurigo, seborrhoeic dermatitis, acne, folliculitis and rosacea.
  • the skin is a tissue of which the cells are joined together and integrally attached to each other.
  • the skin tissue forms an outer covering comprising sebaceous or sweat glands, and hair follicles.
  • the skin, and in particular the scalp, are epithelia which undergo continual renewal.
  • the renewal, or desquamation, is a coordinated and finely regulated process resulting in the imperceptible and invisible removal of the superficial cells.
  • Human skin is constituted of two compartments, namely an upper compartment, the epidermis, and a deep compartment, the dermis.
  • the epidermis is conventionally divided into a basal layer of keratinocytes that constitutes the germinal layer of the epidermis, a spinous layer constituted of several layers of polyhedral cells positioned on the germinal layers, one to three "granular" layers constituted of flattened cells containing distinct cytoplasmic inclusions, keratohyalin granules, and finally a set of upper layers referred to as the cornified layers (or stratum comeum), constituted of keratinocytes at the terminal stage in their differentiation, referred to as corneocytes.
  • cornified layers or stratum comeum
  • Comeocytes are anucleated cells mainly constituted of a fibrous material containing cytokeratins, surrounded by a cornified envelope. New keratinocytes are constantly being produced to compensate for the continuous loss of epidermal cells at the cornified layer by a mechanism referred to as desquamation.
  • an imbalance between the production of cells at the basal layer and the rate of desquamation may particularly lead to the formation of scales on the surface of the skin.
  • a lack of terminal differentiation of the cells of the stratum comeum can result in the formation of large, thick cell clusters which are visible to the naked eye and are referred to as "squamae", or in other situations, in a thinning of the stratum comeum.
  • weakening of the skin barrier can occur in the presence of external attacking factors, notably chosen from irritants (detergents, acids, bases, oxidizing agents, reducing agents, concentrated solvents, gases or noxious fumes, pollutants), thermal or climatic imbalances (cold, drought, radiation), xenobiotics (undesirable microorganisms, allergens) or internal attacking factors such as psychological stress.
  • external attacking factors notably chosen from irritants (detergents, acids, bases, oxidizing agents, reducing agents, concentrated solvents, gases or noxious fumes, pollutants
  • thermal or climatic imbalances cold, drought, radiation
  • xenobiotics undesirable microorganisms, allergens
  • internal attacking factors such as psychological stress.
  • This deterioration of the skin barrier may result in skin discomfort, sensory phenomena and notably unpleasant phenomena.
  • the individual who is affected thereby may then experience a feeling of skin discomfort, which may be manifested in particular by stinging, tautness, hotness and/or itching.
  • These feelings of skin discomfort, of cosmetic and non-therapeutic order are more common in the most exposed areas of the body, namely the hands, the feet, the face and the scalp.
  • CE cornified envelope
  • the moisturizing active ingredients conventionally used such as humectants, moisturizing polymers or fatty substances such as liquid petroleum jelly, temporarily modify the surface properties of the skin.
  • These active ingredients may lead to mechanical softening of the stratum corneum, to an increase in the state of moisturization thereof and/or an improvement in the skin’s microrelief by the formation of a film at the surface of the skin.
  • these effects are not necessarily particularly persistent over time.
  • these active ingredients can be eliminated by cleansing actions.
  • TSLP thymic stromal lymphopoietin
  • IL-29 being able to be regulated by the IL-4 present in type 2 immune responses and atopic dermatitis (Megjugorac et al. Blood. 2010 May 27; 115 (21): 4185-90).
  • IL-4 present in type 2 immune responses and atopic dermatitis
  • active agents that enable the prevention and/or treatment of pruritus and/or inflammation of the skin of an individual, in particular inflammation of skin affected by a dermatological disorder chosen from the group constituted of atopic dermatitis or eczema, psoriasis, nodular prurigo, seborrhoeic dermatitis, acne, folliculitis and rosacea, or by a dermatological disorder following exposure of the skin to pollutants and/or UV rays.
  • a dermatological disorder chosen from the group constituted of atopic dermatitis or eczema, psoriasis, nodular prurigo, seborrhoeic dermatitis, acne, folliculitis and rosacea, or by a dermatological disorder following exposure of the skin to pollutants and/or UV rays.
  • the aim of the present invention is to solve the abovementioned technical problems.
  • indole- 3 -pyruvic acid in a cutaneous model of atopic dermatitis, makes it possible to significantly reduce the production of the chemokine TSLP, the cytokines IL- la, IL-29 and the proteins MCP-1 and MIP-la.
  • the present invention relates to the cosmetic use, notably topical non-therapeutic cosmetic use, of a composition
  • a composition comprising, in a physiologically acceptable medium, indole-3-pyruvic acid, an isomer thereof or a salt thereof, for preventing a reduction in the skin barrier function and/or reinforcing the skin barrier function in an individual, in particular of dry skin.
  • the present invention also relates to the cosmetic use, notably topical non-therapeutic cosmetic use, of a composition comprising, in a physiologically acceptable medium, indole-3-pyruvic acid, an isomer thereof or a salt thereof, for preventing and/or treating atopic dermatitis or eczema.
  • the present invention relates to the cosmetic use, notably topical non-therapeutic cosmetic use, of a composition comprising, in a physiologically acceptable medium, indole-3-pyruvic acid, an isomer thereof or a salt thereof, for preventing and/or treating a skin disorder of sensitive skin, in an individual.
  • a skin disorder may notably be a feeling of discomfort, and in particular tautness, stinging, hotness and/or itching.
  • the present invention relates to the cosmetic use, notably topical cosmetic use, of a composition
  • a composition comprising, in a physiologically acceptable medium, indole- 3 -pyruvic acid, an isomer thereof or a salt thereof, for preventing and/or treating pruritus and/or inflammation of the skin of an individual.
  • a dermatological disorder chosen from the group constituted of atopic dermatitis or eczema, psoriasis, nodular prurigo, seborrhoeic dermatitis, acne, folliculitis and rosacea; or
  • the invention also relates to a non-therapeutic cosmetic method for caring for keratin materials, preferably the skin, comprising the topical application to these keratin materials of a composition comprising, in a physiologically acceptable medium, indole-3- pyruvic acid, an isomer thereof or a salt thereof.
  • a composition used according to the invention may be applied to fragile, weakened, dry, atopic and/or sensitive skin.
  • a composition used according to the invention may notably be suitable for topical administration.
  • composition used according to the invention is Composition used according to the invention.
  • a composition used according to the invention is preferentially suitable for topical application to keratin materials, in particular to the skin, and thus comprises a physiologically acceptable medium, i.e. a medium that is compatible with the skin.
  • cosmetic means a composition that is compatible with keratin materials, in particular the skin, mucous membranes and the integuments.
  • the composition used according to the invention is non-therapeutic.
  • keratin materials is intended to denote in particular the skin, mucous membranes, fibres, eyelashes and skin appendages.
  • skin is intended to mean all of the skin of the body, and preferably the skin of the face, scalp, neckline, neck, arms and forearms, or more preferably still the skin of the face, the skin of the face (in particular of the forehead, nose, cheeks and chin), of the neckline and of the neck.
  • a composition used according to the invention preferably comprises a cosmetically acceptable medium, i.e. one which has a pleasant colour, odour and feel and which does not cause any unacceptable discomfort, i.e. stinging or tautness, liable to discourage the user from applying this composition.
  • a cosmetically acceptable medium i.e. one which has a pleasant colour, odour and feel and which does not cause any unacceptable discomfort, i.e. stinging or tautness, liable to discourage the user from applying this composition.
  • treat and “treatment” mean the alleviation of the symptoms associated with a specific disorder or condition and/or the elimination of said symptoms and also the complete disappearance of the disorder or condition in question.
  • prevent and “prevention” denote the reduction, to a lesser degree, of the risk or probability of occurrence of a given phenomenon.
  • a composition used according to the present invention thus makes it possible to confer beneficial properties on the skin, notably in a long-lasting manner, in particular: effective barrier function; moisturizing effect; elasticity and smooth texture of the skin; surface morphology with low roughness, good tissue cohesion, good thickness of the stratum comeum and an improvement in the visual appearance of the skin.
  • composition used according to the invention may be used on fragile, weakened, dry, atopic and/or sensitive skin of an individual.
  • fragile skin has a disruption of the barrier function leading to permeability and therefore greater reactivity to environmental stresses or aggressions compared with "normal skin” (non-fragile skin). This type of skin is therefore less resistant to stress or environmental aggressions. In addition to the dysfunction of the barrier function, these stresses can also lead to skin inflammation. Lastly, fragile skin is also slower to recover its basal state once exposed to such conditions.
  • Fragile skin is referred to as constitutionally fragile skin, and corresponds, for example, to baby skin, to the skin of an elderly person, or else to the skin of delicate areas of the body (eyelids, face, etc.).
  • atopic skin is understood here to mean skin of a patient exhibiting the same physiological and molecular characteristics as skin of a patient suffering from atopic dermatitis, in particular exhibiting pruritus or inflammation, these manifestations being chronic and interspersed with periods of remission.
  • skin disorder covers feelings of discomfort and also the temporary visible and unattractive cutaneous signs liable to affect this same individual.
  • “Sensitive skin” will therefore present feelings of discomfort much more quickly and frequently than other skin types. Dry skin appears rough to the touch and appears to be covered with squamae and manifests essentially in a feeling of tautness and/or tension. Indeed, dry skin is generally accompanied by desquamation. In physiological terms, dry skin is often particularly associated with a decrease in the degree of skin moisturization and with an adverse effect on the barrier function, measured by the insensible water loss. In sensory terms, it is particularly characterized by feelings of skin tautness and/or tension.
  • Dry skin also known as "xerosis”
  • xerosis Dry skin, also known as "xerosis”
  • a composition according to the invention thus proves to be very particularly effective for treating tautness, stinging, hotness and/or itching, notably associated with fragile, weakened, dry, atopic and/or sensitive skin, for physiologically restoring a suitable state of moisturization of the stratum corneum, for restoring an altered thickness, and in particular thinned thickness, of the stratum corneum of the skin, for improving the comfort of fragile, weakened, dry, atopic and/or sensitive skin, or for combating the dull and/or lifeless appearance of such skin.
  • the indole-3-pyruvic acid is of formula I below:
  • a “salt” of an indole according to the invention is understood to mean a salt formed by an inorganic or organic acid or else an inorganic or organic base.
  • acid salts mention may be made of the sulfate, citrate, acetate, oxalate, chloride, bromide, iodide, nitrate, bisulfate, phosphate, isonicotinate, lactate, salicylate, tartrate, oleate, tannate, pantothenate, bitartrate, ascorbate, succinate, maleate, gentisinate, fumarate, gluconate, glucuronate, saccharate, formate, benzoate, glutamate, methanesulfonate, ethanesulfonate, benzenesulfonate, p-toluenesulfonate and pamoate (i.e.
  • base salts examples include hydroxides of alkali metals such as sodium, potassium and lithium; hydroxides of alkaline earth metals such as calcium and magnesium; hydroxides of other metals such as aluminium and zinc, aqueous ammonia and organic amines such as unsubstituted or hydroxy-substituted mono-, di- or trialkylamines; dicyclohexylamines; tributylamines, pyridine, N-methyl-N-ethylamine; diethylamine; triethylamine; mono-, bis- or tris(2-hydroxyalkylamines) such as mono-, bis- or tris(2-hydroxyethyl)amine, 2-hydroxy-tert-butylamine or tris(hydroxymethyl)methylamine, N,N-di-alkyl-N-(hydroxyalkyl)amines, such
  • a salt of indole-3-pyruvic acid according to the invention is preferably a base salt, and in particular a sodium or potassium salt.
  • a composition used according to the invention may comprise a content of indole-3-pyruvic acid, an isomer thereof or a salt thereof, of at least 0.0001% by weight relative to the total weight of the composition, preferably a content of between 0.0001% and 5% by weight, more preferentially a content of between 0.001% and 1% by weight, better still a content of between 0.001% and 0.01% by weight relative to the total weight of the composition.
  • a composition used according to the invention may further comprise at least one adjuvant chosen from the group constituted of liquid, pasty or solid fatty substances; organic solvents chosen from linear or branched C1-C6 monoalcohols such as ethanol, isopropanol, tert-butanol; polyols such as glycerol, propylene glycol, pentylene glycol, caprylyl glycol, hexylene glycol (or 2-methyl-2,4-pentanediol) and polyethylene glycols; polyol ethers such as dipropylene glycol monomethyl ether; ionic or nonionic, hydrophilic or lipophilic, thickeners; softeners; humectants; emollients; opacifiers; stabilizers; silicones; antifoams; fragrances; preservatives; anionic, cationic, nonionic, zwitterionic or amphoteric surfactants; fillers; polymers; propellant
  • Such an adjuvant may represent from 0.01% to 20%, preferably from 0.1% to 10% and better still from 1% to 5% by weight relative to the total weight of the composition.
  • a composition used according to the invention may comprise from 1% to 95% by weight, preferably from 20% to 80% by weight of water, better still from 30% to 60% by weight, relative to the total weight of the composition.
  • the pH of a composition used according to the invention is advantageously less than or equal to 8, preferably ranging from 4 to 7, better still ranging from 5.5 to 6.5.
  • composition used according to the invention may comprise one or more water-miscible organic solvents.
  • water-miscible solvent denotes a compound that is liquid at room temperature and water-miscible notably having a miscibility with water of greater than 50% by weight at 25°C and atmospheric pressure.
  • the water- miscible organic solvents can be chosen from linear or branched C1-C6 monoalcohols, such as ethanol, isopropanol or tert-butanol; polyols such as glycerol, propylene glycol, pentylene glycol, caprylyl glycol, hexylene glycol (or 2-methyl-2,4- pentanediol) and polyethylene glycols; polyol ethers, for instance dipropylene glycol monomethyl ether; and mixtures thereof.
  • linear or branched C1-C6 monoalcohols such as ethanol, isopropanol or tert-butanol
  • polyols such as glycerol, propylene glycol, pentylene glycol, caprylyl glycol, hexylene glycol (or 2-methyl-2,4- pentanediol) and polyethylene glycols
  • polyol ethers for instance dipropylene glyco
  • water-miscible organic solvents may be present in a composition used according to the invention in a concentration ranging from 0.01% to 20% by weight, preferably from 0.1% to 10% by weight and better still from 1% to 5% by weight, relative to the total weight of the composition.
  • composition used according to the invention may also comprise at least one additional cosmetic active agent.
  • It may in particular be at least one active agent for caring for fragile, weakened, atopic and/or sensitive skin.
  • additional active agent means a compound which has, by itself, that is to say not requiring the intervention of an external agent in order to activate it, a biological activity which may in particular be:
  • the additional active agent which can be used in the compositions used according to the invention may in particular be chosen from humectants such as glycerol and/or urea, emollients such as liquid petroleum jelly, anti-irritant agents, and mixtures thereof in any proportion.
  • the additional active agent used in the composition used according to the invention may represent from 0.0001% to 20%, preferably from 0.01% to 10% and better still from 0.01% to 5% by weight relative to the total weight of the composition.
  • a composition used according to the invention may in particular be in any presentation form normally used in the cosmetic field, and in particular any presentation form normally available for the selected mode of administration.
  • the support may be of diverse nature according to the type of composition considered.
  • compositions according to the invention may be in any presentation form conventionally used for topical application and notably in the form of aqueous or aqueous- alcoholic solutions, oil-in-water (O/W), water-in-oil (W/O) or multiple (triple: W/O/W or O/W/O) emulsions, aqueous gels, or dispersions of a fatty phase in an aqueous phase using spherules, it being possible for these spherules to be lipid vesicles of ionic and/or nonionic type (liposomes, niosomes or oleosomes).
  • These compositions are prepared according to the usual methods.
  • a composition used according to the invention is preferentially suitable for topical administration.
  • compositions intended for topical administration may be aqueous, aqueous-alcoholic or oily solutions, dispersions of the solution type or dispersions of the lotion or serum type, emulsions of liquid or semi-liquid consistency of the milk type, suspensions or emulsions of the cream type, aqueous or anhydrous gels, microemulsions, microcapsules, microparticles, or vesicular dispersions of ionic and/or nonionic type.
  • a composition used according to the invention may advantageously comprise at least one liquid fatty substance.
  • liquid fatty substance means a compound with a melting point below about 30- 35°C, as opposed to solid fatty substances, such as waxes, which have a melting point above about 50 °C.
  • oils which may be used in the composition of the invention, mention may for example be made of:
  • esters and ethers notably of fatty acids, for instance oils of formulae R’COOR2 and R’OR2 in which R’ represents a fatty acid residue including from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain containing from 3 to 30 carbon atoms;
  • hydrocarbon-based oil means any oil mainly including carbon and hydrogen atoms, and possibly ester, ether, fluoro, carboxylic acid and/or alcohol groups.
  • the other fatty substances that may be present in the oily phase are, for example, fatty acids including from 8 to 30 carbon atoms, waxes, silicone resins and silicone elastomers.
  • fatty substances may be chosen in a varied manner by those skilled in the art in order to prepare a composition having the desired properties, for example in terms of consistency or texture.
  • the composition according to the invention is a water-in-oil (W/O) or oil-in-water (O/W) emulsion.
  • W/O water-in-oil
  • O/W oil-in-water
  • the proportion of the oily phase of the emulsion may range from 5% to 90% by weight and preferably from 5% to 60% by weight relative to the total weight of the composition.
  • the emulsions generally contain at least one emulsifier chosen from amphoteric, anionic, cationic and nonionic emulsifiers, used alone or as a mixture, and optionally a coemulsifier.
  • the emulsifiers are appropriately chosen according to the emulsion to be obtained (W/O or O/W).
  • the emulsifier and the coemulsifier are generally present in the composition in a proportion ranging from 0.3% to 30% by weight and preferably from 0.5% to 20% by weight, with respect to the total weight of the composition.
  • emulsifiers examples include dimethicone copolyols and alkyldimethicone copolyols.
  • a crosslinked elastomeric solid organopoly siloxane including at least one oxyalkylene group may also be used as W/O emulsion surfactant.
  • emulsifiers examples of emulsifiers that may be mentioned are nonionic emulsifiers.
  • compositions used according to the invention differs from compositions having an essentially detergent purpose with regard to the skin, hair and/or mucous membranes, such as soaps, shampoos and shower gels for washing and/or cleansing.
  • composition used according to the invention may be intended for topical application and may preferably be in the form of an emulsion, preferably an oil-in- water emulsion.
  • an emulsion is not intended to be rinsed off after application.
  • a composition used according to the invention may alternatively be in the form of a face and/or body care or makeup product, and may be packaged, for example, in the form of a cream in a jar or a fluid in a tube or a pump bottle or a dropper bottle.
  • the ingredients are mixed before forming, in the order and under conditions readily determined by a person skilled in the art.
  • the present invention relates to the cosmetic use, notably topical non-therapeutic cosmetic use, of a composition comprising, in a physiologically acceptable medium, indole- 3 -pyruvic acid, an isomer thereof or a salt thereof, for preventing a reduction in the skin barrier function and/or reinforcing the skin barrier function in an individual, in particular of dry skin, notably for improving skin moisturization.
  • the invention also relates to the cosmetic use, notably topical cosmetic use, of a composition comprising, in a physiologically acceptable medium, indole-3-pyruvic acid, an isomer thereof or a salt thereof, for preventing and/or treating atopic dermatitis or eczema.
  • the present invention additionally relates to the cosmetic use, notably topical non- therapeutic cosmetic use, of a composition comprising, in a physiologically acceptable medium, indole- 3 -pyruvic acid, an isomer thereof or a salt thereof, for preventing and/or treating a skin disorder of sensitive skin, in an individual.
  • the invention additionally relates to a non-therapeutic cosmetic method for caring for keratin materials, in particular the skin, comprising the topical application to these keratin materials of a composition comprising, in a physiologically acceptable medium, indole-3- pyruvic acid, an isomer thereof or a salt thereof.
  • the skin in particular affected by such a method, and thus the skin on which a composition used according to the invention is applied, may preferably be fragile, weakened, dry, atopic and/or sensitive skin.
  • composition used in a method of the present invention is preferably suitable for topical administration.
  • the cosmetic uses, methods and processes considered according to the invention are non- therapeutic.
  • the cosmetic uses and processes of the invention are preferentially performed by topically administering a composition according to the invention.
  • Topical administration consists of the external application to the skin of cosmetic compositions according to the usual techniques for the use of these compositions.
  • the cosmetic use or method according to the invention may be implemented by topical, for example daily, application of at least one composition according to the invention, which may be formulated, for example, in the form of a cream, gel, serum, lotion, emulsion, or makeup-removing milk, preferably in the form of an emulsion.
  • the application can be repeated, for example, once to twice daily for one or more days and generally over an extended period of at least 4 weeks, or even 4 to 15 weeks, with, where appropriate, one or more periods of stoppage.
  • the application is daily (once a day) and generally over an extended period of at least 4 weeks, or even 4 to 15 weeks, with, where appropriate, one or more periods of stoppage.
  • the cosmetic treatment method according to the invention may comprise a single application.
  • the temperature is room temperature (20°C) and is expressed in degrees Celsius
  • the pressure is atmospheric pressure.
  • the 3T3 fibroblasts (ATCC, CRL-1658), used as feeders for the keratinocytes, were initially cultured in DMEM (Ref 12491015, ThermoFisher) and treated with a 0.5 mg/ml solution of mitomycin (Sigma, M4287) before freezing. The mitomycin-treated 3T3 are then inoculated at 2.1 million per flask in 30 ml of G7 and incubated in an oven at 37°C, 5% CO2 (2-3 hours).
  • NHEK normal human epidermal keratinocytes
  • NHEK When the flasks with 3T3 feeder are at 80-90% confluence, 50 000 NHEK are seeded in a 48-well plate with 1 ml of KGM Gold medium without hydrocortisone and 1 ml BPE (bovine pituitary extract) (instead of the 2 ml contained in the supplements of the KGM Gold kit); Y27632 10 pM. This is followed by an incubation step in an oven for 72 h at 37°C, 5% CO 2 .
  • BPE bovine pituitary extract
  • a step of exposure to a stimulation cocktail as defined below is carried out in order to induce a phenotype similar to that observed in patients with atopic dermatitis in terms of chemokines produced.
  • - IL-4 5 pg/ml (used at 50 ng/ml in the well) ref. 204-IL, RnDSystems; and
  • the various molecules of interest are added to the KGM Gold culture medium:
  • - IALD ref 129445, Sigma: stock solution 10 mg/ml in DMSO diluted in the culture medium to the final concentration of 10 pg/ml and 25 pg/ml; or - FICZ ref: SML1489, Sigma: stock solution 0.5 mg/ml in DMSO diluted in culture medium at the final concentration of 0.05 and 0.1
  • IALD is also a positive control. Indeed, in the study by Yu et al. (J Allergy Clin Immunol, 2019 Jun;143(6):2108-2119.el2), topical application of IALD made it possible to reduce skin inflammation in a dermatitis-like mouse model.
  • TSLP (thymic stromal lymphopoietin) is a key chemokine of keratinocyte communication due to its ability to induce itching by directly activating certain types of neurons (TRPA- 1+) and also the type 2 immune responses involved in atopic dermatitis.
  • MCP-1 and MIP-la are proteins involved in inflammatory processes in type 2 immune responses, in particular in patients suffering from atopic dermatitis where they are markedly increased (Kaburagi et al., Arch Dermatol Res. 2001 Jul;293(7):350-5). These tables show a significant reduction in the production of the chemokines TSLP, IL- la, and IL-29 and also of the proteins MCP-1 and MIP-la for I3P and FICZ, which reduction cannot be observed with IALD. In conclusion, all of these results demonstrate that I3P has a very good ability to restore the barrier function of the epidermis, notably compared to IALD.

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Abstract

La présente invention concerne l'utilisation cosmétique, notamment l'utilisation cosmétique non thérapeutique topique, d'une composition comprenant, dans un milieu physiologiquement acceptable, de l'acide indole-3-pyruvique, un isomère de celui-ci ou un sel de celui-ci, pour prévenir une réduction de la fonction barrière cutanée et/ou renforcer la fonction barrière cutanée chez un individu, en particulier de la peau sèche. L'invention concerne également l'utilisation d'une telle composition pour prévenir et/ou traiter un trouble cutané dans la peau sensible chez un individu, ainsi que l'utilisation d'une telle composition pour prévenir et/ou traiter le prurit et/ou l'inflammation de la peau d'un individu. Enfin, l'invention concerne un procédé cosmétique non thérapeutique pour le soin des matières kératiniques, en particulier de la peau, comprenant l'application topique sur ces matières kératiniques d'une telle composition.
PCT/EP2023/086063 2022-12-16 2023-12-15 Utilisation cosmétique d'une composition pour le soin des matières kératiniques comprenant au moins de l'acide indole-3-pyruvique WO2024126794A1 (fr)

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Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
ANONYMOUS: "Atopic dermatitis", WIKIPEDIA, 6 December 2022 (2022-12-06), pages 1 - 15, XP093060392, Retrieved from the Internet <URL:https://en.wikipedia.org/w/index.php?title=Atopic_dermatitis&oldid=1125844347> [retrieved on 20230703] *
ANONYMOUS: "QU'EST-CE QU'UN COUP DE SOLEIL ?", VIDAL.FR, 11 October 2022 (2022-10-11), pages 1 - 1, XP093060907, Retrieved from the Internet <URL:https://www.vidal.fr/maladies/peau-cheveux-ongles/coup-soleil-erytheme-solaire.html> [retrieved on 20230704] *
AOKI REIJI ET AL: "Protective Effect of Indole-3-Pyruvate against Ultraviolet B-Induced Damage to Cultured HaCaT Keratinocytes and the Skin of Hairless Mice", PLOS ONE, vol. 9, no. 5, 8 May 2014 (2014-05-08), pages e96804, XP093060697, DOI: 10.1371/journal.pone.0096804 *
DVORÁK ZDENEK ET AL: "Drug Mimicry: Promiscuous Receptors PXR and AhR, and Microbial Metabolite Interactions in the Intestine", TRENDS IN PHARMACOLOGICAL SCIENCES, ELSEVIER, HAYWARTH, GB, vol. 41, no. 12, 20 October 2020 (2020-10-20), pages 900 - 908, XP086341456, ISSN: 0165-6147, [retrieved on 20201020], DOI: 10.1016/J.TIPS.2020.09.013 *
HAFTEK ET AL., CLIN COSMET INVESTIG DERMATOL, vol. 6, 2013, pages 289 - 294
KABURAGI ET AL., ARCH DERMATOL RES, vol. 293, no. 7, July 2001 (2001-07-01), pages 350 - 5
KIM KYUNGHEE ET AL: "Effects of Indole-3-Lactic Acid, a Metabolite of Tryptophan, on IL-4 and IL-13-Induced Human Skin-Equivalent Atopic Dermatitis Models", INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, vol. 23, no. 21, 4 November 2022 (2022-11-04), pages 13520, XP093060761, DOI: 10.3390/ijms232113520 *
MALIKKANNEGANTI, IMMUNOL REV, vol. 281, no. 1, January 2018 (2018-01-01), pages 124 - 137
MEGJUGORAC ET AL., BLOOD, vol. 115, no. 21, 27 May 2010 (2010-05-27), pages 4185 - 90
YU ET AL., J ALLERGY CLIN IMMUNOL, vol. 143, no. 6, June 2019 (2019-06-01), pages 2108 - 2119
YU JINLEI ET AL: "A tryptophan metabolite of the skin microbiota attenuates inflammation in patients with atopic dermatitis through the aryl hydrocarbon receptor", JOURNAL OF ALLERGY AND CLINICAL IMMUNOLOGY, vol. 143, no. 6, 1 June 2018 (2018-06-01), pages 2108, XP085705057, ISSN: 0091-6749, DOI: 10.1016/J.JACI.2018.11.036 *

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