WO2006048339A2 - Composition cosmetique comprenant un agent actif et un compose d'uree - Google Patents

Composition cosmetique comprenant un agent actif et un compose d'uree Download PDF

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Publication number
WO2006048339A2
WO2006048339A2 PCT/EP2005/013527 EP2005013527W WO2006048339A2 WO 2006048339 A2 WO2006048339 A2 WO 2006048339A2 EP 2005013527 W EP2005013527 W EP 2005013527W WO 2006048339 A2 WO2006048339 A2 WO 2006048339A2
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WIPO (PCT)
Prior art keywords
composition according
acid
chosen
active agent
skin
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PCT/EP2005/013527
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English (en)
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WO2006048339A3 (fr
Inventor
Véronique Burnier
Raluca Lorant
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L'oréal
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Priority claimed from FR0452518A external-priority patent/FR2877223B1/fr
Priority claimed from FR0412368A external-priority patent/FR2877221B1/fr
Application filed by L'oréal filed Critical L'oréal
Publication of WO2006048339A2 publication Critical patent/WO2006048339A2/fr
Publication of WO2006048339A3 publication Critical patent/WO2006048339A3/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides

Definitions

  • Cosmetic composition comprising an active agent and a urea compound
  • the present invention relates to a cosmetic or dermatological composition comprising a urea compound and an active agent.
  • the invention also relates to a method of treating the skin of a human being, comprising the application of the composition to the skin.
  • Active agents can also be retained because of specific affinities with an adjuvant pre ⁇ sent in the cosmetic composition delivering the active agent, making the latter insuffi ⁇ ciently available for crossing the stratum corneum.
  • the aim of the present invention is therefore to provide a composition for caring for or making up the skin, comprising a skincare active agent which makes it possible, after application of the composition to the skin, to promote the penetration of the active agent in the skin so as to reach the living layers of the dermis, of the epidermis and of the hypodermis.
  • the active agent crosses the stratum corneum and reaches, in the dermis and the epidermis, the biological targets (cells, enzymes) to be activated or in ⁇ hibited so as to promote the cosmetic effects beneficial to the skin.
  • Such effects are es ⁇ pecially the prevention or the treatment of signs of skin ageing, and in particular of wrin ⁇ kles, the loss of firmness and of tonicity of the skin, slimming and/or refining of the figure and/or of the contours of the face, the prevention or the treatment of cellulite and/or of the « orange-peel » appearance, the prevention or the combating of skin irritations and/or dry patches and/or erythema and/or pruritis of the skin and/or feelings of heating of the skin and/or feelings of tautness of the skin and/or feelings of pins and needles of the skin and/or feelings of redness of the skin.
  • the inventors have discovered that such a composition is obtained by combining a spe ⁇ cific urea compound with the skincare active agent.
  • a subject of the invention is a composition comprising, in a physiologi ⁇ cally acceptable medium, at least one urea compound of formula (I) as defined hereinaf- ter, and at least one active agent as described hereinafter.
  • active agent » is intended to mean a skincare active agent capable, on its own, of modifying a biological function of the skin.
  • a subject of the invention is also a cosmetic method of non-therapeutic treatment of the skin or of making up the skin, comprising the application to the skin of a composition as defined above.
  • the urea compound present in the composition according to the invention is a com- pound of formula (I) below:
  • , R2, R3 and R4 each represent, independently of one another, a hydrogen atom, a C-
  • R-j denotes a C2-C6 hydroxyalkyl group
  • R2, R3 and R4 denote, inde ⁇ pendently of one another, a hydrogen atom or a C-J -C4 alkyl group
  • denotes a C2-C6 hydroxyalkyl group comprising from 1 to 5 hydroxyl groups, in particular one hydroxyl group, and R2, R3 and R4 denote a hydrogen atom;
  • denotes a C2-C4 hydroxyalkyl group comprising one hydroxyl group
  • R2, R3 and R4 denote a hydrogen atom.
  • alkyl groups mention may be made of methyl, ethyl, n-propyl, isopropyl, n- butyl, isobutyl and tert-butyl groups.
  • hydroxyalkyl groups preference is given to those containing a single hy- droxyl group, and in particular hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl and hydroxyethyl groups.
  • salts of inorganic acids such as sulphuric acid, hydrochloric acid, hydrobromic acid, hydriodic acid, phosphoric acid or boric acid.
  • salts of organic acids may contain one or more carboxylic, sulphonic or phosphonic acid groups. They may be linear, branched or cyclic aliphatic acids or else aromatic acids. These acids may also contain one or more hetero atoms chosen from O and N, for example in the form of hydroxyl groups.
  • Mention may in particular be made of propionic acid, acetic acid, terephthalic acid, citric acid and tar ⁇ taric acid.
  • solvate » is intended to mean a stoichiometric mixture of said compound of formula (I) with one or more molecules of water or of organic solvent, such a mixture being derived from the synthesis of the compound of formula (I).
  • N-(2- hydroxyethyl)urea N-(2-hydroxypropyl)urea; N-(3-hydroxypropyl)urea; N-(2,3- dihydroxypropyl)urea; N-(2,3,4,5,6-pentahydroxyhexyl)urea; N-methyl-N-(1 ,3,4,5,6- pentahydroxy-2-hexyl)urea; N-methyl-N'-(1-hydroxy-2-methyl-2-propyl)urea; N-(1- hydroxy-2-methyl-2-propyl)urea; N-(1 ,3-dihydroxy-2-propyl)urea; N-
  • the compound of formula (I) is N-(2-hydroxyethyl)urea.
  • the compounds of formula (I) are compounds that are known and are in particular de- scribed in application DE-A-2703185.
  • N-(2-hydroxyethyl)urea is also commercially available, in the form of a mixture at 50% by weight in water, from the company National Starch under the trade name Hydrovance ® .
  • the compound of formula (I) may be present in the composition according to the inven- tion in an amount ranging from 0.1% to 50% by weight, relative to the total weight of the composition, preferably ranging from 0.1% to 20% by weight, and preferentially ranging from 0.1% to 10% by weight.
  • the active agents present in the composition according to the invention are chosen from dermal relaxant active agents, agents that stimulate the synthesis of dermal or epidermal extracellular matrix fibres or fibres located in the dermal-epidermal junction and/or that prevent their degradation, anti-glycation agents, lipolytic active agents or active agents that inhibit lipogenesis, anti-irritants, and mixtures thereof.
  • the active agents present in the composition according to the invention can also be chosen from carotenoids, retinoids, flavanones, flavonols, isoflavones, coumarins, lignans, stilbenoids, sapogenins, pentacyclic triterpenic acids, ⁇ -hydroxy acids, hydroxyphenols and ether or heteroside derivatives thereof, phenolic acids, monomers that are tanin precursors, amino sugars, peptides, and mixtures thereof.
  • the active agents described above may be present in the composition according to the invention in an amount ranging from 0.01% to 10% by weight, relative to the total weight of the composition, and preferably ranging from 0.1 % to 8% by weight, preferentially ranging from 0.1 % to 5% by weight, and more preferentially ranging from 0.1% to 3% by weight.
  • a subject of the invention is therefore a composition
  • a composition comprising, in a physiologically acceptable medium, at least one urea compound of formula (I) as defined above, and at least one active agent chosen from dermal relaxant active agents, agents that stimulate the synthesis of dermal or epidermal extracellular matrix fibres or of fibres located in the dermal-epidermal junction and/or that prevent their degradation, anti-glycation agents, lipolytic active agents or active agents that inhibit lipogenesis, anti-irritants, and mixtures thereof.
  • dermal relaxant active agents agents that stimulate the synthesis of dermal or epidermal extracellular matrix fibres or of fibres located in the dermal-epidermal junction and/or that prevent their degradation, anti-glycation agents, lipolytic active agents or active agents that inhibit lipogenesis, anti-irritants, and mixtures thereof.
  • composition according to the invention is generally suitable for topical application to the skin and therefore generally comprises a physiologically acceptable medium, i.e. a medium that is compatible with the skin. It is preferably a cosmetically acceptable me ⁇ dium, i.e. a medium that has a pleasant colour, odour and feel, and that does not gen- erate any unacceptable discomfort (tingling, tautness, redness) that may put the con ⁇ sumer off using this composition.
  • a physiologically acceptable medium i.e. a medium that is compatible with the skin.
  • me ⁇ dium i.e. a medium that has a pleasant colour, odour and feel, and that does not gen- erate any unacceptable discomfort (tingling, tautness, redness) that may put the con ⁇ sumer off using this composition.
  • composition according to the invention may comprise a dermal relaxant active agent.
  • Some wrinkles of the skin are caused by fibroblast microcontractions which create areas of tension by pulling the protein fibres of the extracellular matrix. It is therefore necessary for the dermal relaxant active agents to be able to reach the dermal cells in order to bring about cellular relaxation.
  • the dermal relaxant active agent By combining the dermal relaxant active agent with a urea compound of formula (I), the penetration of the dermal relaxant active agent into the skin is promoted, and the effect on the wrinkles and fine lines, in particular the expression wrinkles and fine lines, is thus improved.
  • the dermal relaxant active agents that can be used in the composition according to the invention comprise in particular alverine and its salts, magnesium chlorides or gluconates or manganese chlorides or gluconates, diazepam, the hexapeptide glutamic acid-glutamic acid-methionine-glutamic acid-arginine-arginine, the first (N-terminal) being acetylated and the last (C-terminal) being amidated, as sold under the name Argireline by the company Lipotec, carbonylated secondary and tertiary amines as described in application EP-A-1405633, the content of which is incorporated into the present application by way of reference (in particular, 3-(ethyl-(3-hydroxy-3- pentyloctyl)amino)propiophenone), adenosine, and also sapogenins and the natural extracts, in particular of wild yam, containing them, and also 3-O-acetyl 11-keto
  • the dermal relaxant active agents are chosen from adenosine, the copper salt of the tripeptide glycine-histidine-lysine, magnesium gluconate, manganese gluconate, sapogenins extracted from wild yam, and mixtures thereof.
  • the composition comprises, in a physiologically acceptable medium, a urea compound of formula (I) and at least one dermal relaxant active agent as defined above.
  • composition according to the invention comprising these dermal relaxant active agents is preferentially intended to be used for preventing or treating the signs of skin ageing, and in particular wrinkles, and/or for decontracting the skin.
  • the subject of the invention is therefore also a method of non-therapeutic treatment of wrinkled skin, comprising the application to the wrinkled skin of a composition comprising, in a physiologically acceptable medium, a urea composition of formula (I) and at least one dermal relaxant active agent as defined above.
  • composition according to the invention may comprise an agent that stimulates the synthesis of dermal or epidermal extracellular matrix fibres or of fibres located in the dermal-epidermal junction and/or that prevents their degradation.
  • the cells of the dermis in particular the fibroblasts, produce collagen and elastin fibres.
  • These fibres give the skin its volume and its density, and also its firmness.
  • age or alternatively under the effect of UV rays, a notable decrease in these molecules occurs, and also a degradation of the collagen and elastin fibres under the effect of collagenase or of elastase, which are enzymes in the skin.
  • This degradation or decrease in the production of these fibres induces a loss of firmness of the skin, and also the appearance of wrinkles at the surface of the skin.
  • elastin such as the extract of Saccharomyces cerivisiae sold by the company LSN under the trade name Cytovitin ® ; and the extract of the alga Macrocystis pyrifera sold by the company Secma under the trade name Kelpadelie ® ; melibiose; soybean proteins; lactose, a magnesium aspartate/zinc gluconate/copper gluconate mixture, such as that sold by the company Seppic under the name « Sepivital » extracts of red clover (Trifolium pratense) containing isoflavones;
  • Trifolium pratense Trifolium pratense
  • fibronectin such as the extract of the zooplancton Artemia salina sold by the company Seporga under the trade name GP4G ® ; the yeast extract available in particular from the company Alban M ⁇ ller under the trade name Drieline ® ; and the palmitoyl of lysine-threonine-threonine-lysine-serine pentapeptide sold in particular under the name « Matrixyl » by the company Sederma;
  • MMPs matrix metalloproteinases
  • peptide extract of leguminous plant sold by the company LSN under the trade name Parelastyl ® ; heparinoids; and pseudodipeptides, such as ⁇ 2-[acetyl-(3-trifluoromethylphenyl)amino]-3- methylbutyrylamino ⁇ acetic acid.
  • the active agents that stimulate the synthesis of dermal or epidermal fibres or that prevent their degradation are chosen from extracts of Centella asiatica, ascorbic acid and its derivatives, peptides extracted from plants, such as the soybean hydrolysate sold by the company Coletica under the trade name Phytokine; ⁇ 2-[acetyl-(3-trifluoromethylphenyl)amino]-
  • 3-methylbutyrylamino ⁇ acetic acid the palmitoyl of lysine-threonine-threonine-lysine-serine pentapeptide sold in particular under the name « Matrixyl » by the company Sederma; dipalmitoyl hydroxyproline sold by the company Seppic under the name « Seppilift DPHP » and phytosterol sulphate, such as that sold by the company Vincience under the name
  • the compounds of formula (I) descibed above, combined with vitamin C may make it possible to decrease, or even prevent, the oxidation of vitamin C by oxygen, in particular in contact with water when the latter is present in the composition.
  • the vitamin C is thus given greater stability with respect to the oxidation caused by oxygen.
  • the composition comprises, in a physiologically acceptable medium, a urea compound of formula (I) and an agent that stimulates the synthesis of dermal or epidermal extracellular matrix fibres or the synthesis of fibres located in the dermal-epidermal junction and/or that prevents their degradation, as described above.
  • composition according to the invention comprising these active agents is preferentially intended to be used for preventing or treating the signs of skin ageing, and in particular wrinkles and loss of firmness.
  • a subject of the invention is also a method of non-therapeutic cosmetic treatment for the purpose of preventing and/or combating the signs of skin ageing, in particular wrinkles and/or loss of firmness of the skin, comprising the application to the skin of a composition comprising, in a physiologically acceptable medium, a urea compound of formula (I) and an agent that stimulates the synthesis of dermal or epidermal extracellular matrix fibres or of fibres located at the dermal-epidermal junction and/or that prevents their degradation, as described above.
  • a composition comprising, in a physiologically acceptable medium, a urea compound of formula (I) and an agent that stimulates the synthesis of dermal or epidermal extracellular matrix fibres or of fibres located at the dermal-epidermal junction and/or that prevents their degradation, as described above.
  • composition according to the invention may comprise an anti-glycation agent.
  • Glycation is a non-enzymatic process involving a monosaccharide (glucose or ribose) that reacts according to the Maillard reaction with an amino group of an amino acid residue (such as, for example, lysine), particularly an amino acid residue of a protein, so as to form a Schiffs base.
  • a monosaccharide such as, for example, lysine
  • amino acid residue such as, for example, lysine
  • the latter after « Amadori » molecular rearrangement, can, by means of a succession of reactions, result in bridging, particularly intramolecular bridging, for instance of pentosidine type.
  • the glycation products are, for example, pyrraline, carboxymethyl-lysine, pentosidine, crossline, N ⁇ -(2-carboxyethyl)lysine (CEL), glyoxallysine dimer (GOLD), methylglyoxallysine dimer (MOLD), 3DG-ARG imida- zolone, versperlysines A, B and C, threosidine, or else advanced glycation end products (or AGEs).
  • CEL N ⁇ -(2-carboxyethyl)lysine
  • GOLD glyoxallysine dimer
  • MOLD methylglyoxallysine dimer
  • 3DG-ARG imida- zolone versperlysines A, B and C, threosidine, or else advanced glycation end products (or AGEs).
  • the glycation of proteins is therefore a universal phenomenon that is well known in the skin, particularly in its dermal component, and mainly in the collagen fibres. Collagen glycation in fact increases regularly with age, resulting in a regular increase in the con- tent of glycation products in the skin.
  • glycation is involved in the characteristic "or ⁇ ange-peel" appearance of cellulite. Specifically, in cellulite, the glycation of the collagen constituting the majority of the connective sections results in a rigidification of the tis- sues, which then imprison the fat globules. The skin thus shows a succession of bumps formed by fatty lumps and of hollows formed by rigidified connective sections, which are characteristic of the "orange-peel" appearance.
  • the compounds of formula (I) described above combined with an anti-glycation agent, promote the penetration of the active agent in the skin and thus improve the effect of the active agent for the prevention or treatment of the signs of skin ageing associated with glycation, in particular for preventing or treating the loss of tonicity of the skin due to age; for slimming and/or refining the figure and/or the contours of the face; for preventing or treating the « orange-peel » appearance.
  • anti-glycation agent is intended to mean a compound that prevents and/or decreases glycation of the proteins of the skin, in particular of the proteins of the dermis, such as collagen.
  • anti-glycation agents are extracts of plants of the family Ericaceae, such as an extract of blueberry (Vaccinium angustifolium), for example that sold under the name « Blueberry Herbasol Extract PG » by the company Cosmetochem; ergothioneine and its derivatives; hydroxystilbenes and their derivatives, such as resveratrol and 3,3', 5,5'- tetrahydroxystilbene (these anti-glycation agents are described in applications FR 2 802 425, FR 2 810 548, FR 2 796 278 and FR 2 802 420, respectively); arginine and lysine polypeptides such as that sold under the name « Amadorine » by the company Solabia; carsinine hydrochloride (sold by Exsymol under the name « Austin »); and mixtures thereof.
  • blueberry Vaccinium angustifolium
  • Blueberry Herbasol Extract PG » by the company Cosmetochem
  • Extract of blueberry, arginine and lysine polypeptides (such as that sold under the name « Amadorine » by the company Solabia), carcinine hydrochloride, and mixtures thereof, are preferably used as anti-glycation agent.
  • the composition comprises, in a physiologically acceptable medium, a urea compound of formula (I) and an anti- glycation agent as described above.
  • a subject of the invention is therefore also a method of non-therapeutic treatment of the skin, for preventing or treating the signs of skin ageing associated with glycation and/or for preventing or treating the loss of tonicity of the skin due to age and/or for slimming and/or refining the figure and/or the contours of the face and/or for preventing or treating the « orange-peel » appearance, comprising the application to the skin of a composition comprising, in a physiologically acceptable medium, a urea compound of formula (I) and an anti-glycation active agent as defined above.
  • composition according to the invention may comprise a lipolytic active agent or an active agent that inhibits lipogenesis.
  • phosphodiesterase inhibitors such as:
  • xanthine derivatives such as caffeine and its derivatives, in particular the 1-hydroxyalkylxanthines described in document FR-A-2, 617,401 , caffeine citrate, theophylline and its derivatives, theobromine, acefylline, aminophylline, chloroethyltheophylline, diprofylline, diniprophylline, etamiphylline and its derivatives, etofylline and proxyphylline;
  • xanthine derivatives such as the combination of caffeine and silanol (caffeine methyl silanetriol derivative) and, for example, the product sold by the company Exsymol under the name cafeisilane C
  • xanthine derivatives such as the combination of caffeine and silanol (caffeine methyl silanetriol derivative) and, for example, the product sold by the company Exsymol under the name cafeisilane C
  • - compounds of natural origin containing xanthine bases, and in particular caffeine such as extracts of tea, of coffee, of guarana, of mate, of cola (Cola nitida) and in particular the dry extract of guarana fruit (Paulina sorbilis) containing 8 to 10% of caffeine
  • caffeine such as the combination of caffeine and silanol (caffeine methyl silanetriol derivative) and, for example, the product sold by the company Exsymol under the name cafeisilane C
  • caffeine such as extracts of tea, of coffee,
  • plant extracts and extracts of marine origin which either are active on the receptors to be inhibited, such as ⁇ -2-blockers or neuropeptide Y blockers (described in patent EP 838217), or which inhibit the synthesis of LDL (low density lipoprotein) or VLDL (very low density lipoprotein) receptors, or which are active in stimulating ⁇ -receptors and G proteins, resulting in the activation of adenylcyclase.
  • ⁇ -2-blockers or neuropeptide Y blockers described in patent EP 838217
  • LDL low density lipoprotein
  • VLDL very low density lipoprotein
  • inhibitors are in particular described in application EP-A6655235.
  • the lipolytic agents or agents that inhibit lipogenesis, present in the composition according to the invention may be chosen from caffeine and its derivatives, extracts of ginkgo biloba, diosgenin, extract of Laminaria digitata, and mixtures thereof.
  • the composition comprises, in a physiologically acceptable medium, a urea compound of formula (I) and a lipolytic active agent or active agent that inhibits lipogenesis as defined above.
  • composition according to the invention containing one or more of the compounds above is particularly suitable for use in preventing or combating cellulite and/or the « orange-peel » appearance and/or refining or slimming the figure or the contours of the face.
  • a subject of the invention is therefore also a method of non-therapeutic cosmetic treatment for the purpose of preventing and/or combating cellulite and/or the « orange- peel » appearance and/or of refining or slimming the figure or the contours of the face, comprising the topical application to the skin of the composition comprising, in a physiologically acceptable medium, a urea compound of formula (I) and a lipolytic active agent or active agent that inhibits lipogenesis as defined above.
  • Anti-irritants for the purpose of preventing and/or combating cellulite and/or the « orange- peel » appearance and/or of refining or slimming the figure or the contours of the face, comprising the topical application to the skin of the composition comprising, in a physiologically acceptable medium, a urea compound of formula (I) and a lipolytic active agent or active agent that inhibits lipogenesis as defined above.
  • composition according to the invention may comprise an anti-irritant.
  • anti-irritant » is intended to mean an active agent that modulates the mani ⁇ festations of sensitive skin, i.e. the manifestations of skin irritation, such as tingling, tautness, the feeling of heat and diffuse red blotches.
  • skin irritation is intended to mean any form of irritation resulting from the ap- plication to the skin of chemical products of natural or synthetic origin, for example used in cosmetics or dermatology, and which may be reflected in particular by red blotches, pain or tingling.
  • sensitive skin covers both irritable and/or reactive skin and intolerant skin.
  • Irritable and/or reactive skin is skin that reacts through pruritis, i.e. through itching or through tingling, to various factors such as the environment, emotions, foods, the wind, rubbing, shaving, soap, surfactants, hard water with a high calcium concentration, tem- perature variations or wool.
  • these signs are associated with dry skin with or without dry patches, or with skin that exhibits erythema.
  • Intolerant skin is skin that reacts through feelings of heating, of tautness, of pins and needles and/or of redness, to various factors such as the environment, emotions, foods and certain cosmetic products. In general, these signs are associated with hyperseborrhoeic or acneic skin with or without dry patches, and with erythema.
  • the manifestations of skin irritation are caused by the release of neuromediators by the nerve fibres, the ends of which are in the live epidermis.
  • neuromediators mention may be made of substance P, CGRP (calcitonin gene related peptide), vasoactive intestinal peptide (VIP) and bradykinin.
  • Anti-irritant active agents applied to the skin make it possible to decrease the effects of skin irritation, or even to make them disappear.
  • anti-irritants of: - sodium channel blockers, and/or - agents that interact specifically with neuromediator receptors or neurohormone recep ⁇ tors, chosen from substance P antagonists, CGRP antagonists, and bradykinin antago ⁇ nists.
  • sodium channel blocker is intended to mean a substance that responds like a sodium antagonist substance in the model de ⁇ scribed by Y. Jacques et al. (J. Biol. Chem., 1987, 253, page 7383) and/or a substance that responds like a substance which binds specifically in the sodium channel binding models described by W. A. Catterall et al. (J. Biol. Chem., 1979, 254, page 11379) or by G. B. Brown, (J. Neuroscience, 1986, 6, page 2064).
  • sodium channel inhibitors in the in ⁇ vention amiloride, quinidine, quinidine sulphate, apamine, cyproheptadine, loperamide and N-acetylprocainamide.
  • amiloride is used.
  • the term "substance P antagonist” is intended to mean a substance of organic or mineral origin capable of producing an inhibition of sub ⁇ stance P receptor binding or of producing an inhibition of the synthesis and/or of the re ⁇ lease of substance P by sensory nerve fibres.
  • the antagonist substance must have a selective affinity for tachykinin NK1 receptors, and/or - the antagonist substance must cause an inhibition of the release and/or of the synthe ⁇ sis of substance P and/or the antagonist substance must cause an inhibition of the smooth muscle contraction induced by the administration of substance P.
  • substance P antagonists are in particular: strontium salts; spring waters, and in particular the spring water of the Vichy basin and the spring water of La Roche Posay; dead sea salts; bacterial extracts, and in particular the extract of non- photosynthetic filamentous bacteria described in patent application EP-O 761 204, pref ⁇ erably prepared from bacteria belonging to the order Beggiatoales, and more particu ⁇ larly to the genera Beggiatoa, Vitreoscilla, Flexithrix or Leucothrix. According to the in ⁇ vention, a strain of Vitreoscilla filiformis, or the dead sea salts are preferentially used.
  • CGRP anta b ⁇ ,ts is intended to mean a substance of organic or mineral origin capable of producing an inhibition of CGRP re ⁇ ceptor binding or of producing an inhibition of the synthesis and/or of the release of CGRP by sensory nerve fibres.
  • CGRP- antagonist For a substance to be recognized as a CGRP antagonist, it must have a CGRP- antagonist pharmacological activity, i.e. it must induce a coherent pharmacological re ⁇ sponse in particular in one of the following tests:
  • the antagonist substance must have a selective affinity for the CGRP receptor and/or - the antagonist substance must cause an inhibition of the release of CGRP by sensory nerve fibres and/or
  • the antagonist substance must decrease inhibition of vas deferens smooth muscle contraction induced by CGRP.
  • a non-limiting example of a CGRP antagonist that can be used in the present invention consists of an extract of cells (preferably undifferentiated cells) of at least one plant of the family Iridaceae, obtained by in vitro culture.
  • the lridacea preferably belongs to one of the following genera: Romulea, Crocus, Iris, Gladiolus, Sisyrinchium and Hermodac- tylus.
  • an extract of plant material originating from Iris, better still from Iris pallida, as described in application EP-O 765 668, is preferably used.
  • Extracts of mint leaves such as those sold under the name « calmiskin » by the company Silab
  • extracts of linseed such as that sold under the name « Sensiline » by the company Silab.
  • bradykinin antagonist is intended to mean a substance capable of inhibiting the release and/or the synthesis and/or the receptor binding of bradykinin.
  • Antagonists that inhibit bradykinin receptor binding are agents specific for the bradykinin type-1 (B 1 ) and/or type-2 (B 2 ) receptor. Their mechanism of action is particularly described in patent application EP-O 756 862, the content of which is incorporated herein by way of reference.
  • a non-limiting example of a bradykinin antagonist that can be used in the present inven ⁇ tion consists of an extract of at least one plant of the family Rosaceae, preferably culti ⁇ vated in vivo.
  • the extract of Rosacea may preferentially belong to the following genera: Agrimonia, Amygdalus, Armeniaca, Cerasus, Malus, Mespilus, Persica, Pirus, Prunus, Rosa, Rubus.
  • an extract of a plant belonging to the Rosa genus advantageously prepared from material derived from at least one plant belonging to a species chosen from Rosa alba, Rosa alpina, Rosa canina, Rosa cinnamonea, Rosa gallica, Rosa repens, Rosa rubrifolia, Rosa rubiginosa, Rosa sem- pervirens, Rosa spinosissima, Rosa stylosa, Rosa tomentosa and Rosa villosa.
  • Rosa gallica as described in patent application EP- 0 909 556.
  • the anti-irritant used according to the invention may be of natural or synthetic origin.
  • natural origin » is intended to mean an inhibitor in pure form or in solution, whatever its concentration in said solution, obtained from a natural element by means of various methods.
  • synthetic origin » is intended to mean an anti-irritant in pure form or in solution, whatever its concentration in said solution, obtained by chemi- cal synthesis.
  • the composition comprises, in a physiologically acceptable medium, a urea compound of formula (I) and an anti-irritant as defined above.
  • a subject of the invention is also a non-therapeutic cosmetic method for preventing and/or combating skin irritations and/or dry patches and/or erythema and/or pruritis of the skin and/or feelings of heating of the skin and/or feelings of tautness of the skin and/or feelings of pins and needles in the skin and/or feelings of redness of the skin, comprising the application to the skin of a composition comprising, in a physiologically acceptable medium, a urea compound of formula (I) and an anti-irritant as defined above.
  • the active agents present in the composition according to the invention can also be chosen from carotenoids, retinoids, flavanones, flavonols, isoflavones, coumarins, lignans, stilbenoids, sapogenins, pentacyclic triterpenic acids, ⁇ -hydroxy acids, hydroxyphenols and their ether or heteroside derivatives, phenolic acids, monomers that are tanin precursors, amino sugars, peptides, and mixtures thereof.
  • a subject of the invention is therefore also a composition
  • a composition comprising, in a physiologically acceptable medium, at least one urea compound of formula (I) as defined above, and at least one active agent chosen from carotenoids, retinoids, flavanones, flavonols, isoflavones, coumarins, lignans, stilbenoids, sapogenins, pentacyclic triterpenic acids, ⁇ -hydroxy acids, hydroxyphenols and their ether or heteroside derivatives, phenolic acids, monomers that are tanin precursors, amino sugars, peptides, and mixtures thereof.
  • active agent chosen from carotenoids, retinoids, flavanones, flavonols, isoflavones, coumarins, lignans, stilbenoids, sapogenins, pentacyclic triterpenic acids, ⁇ -hydroxy acids, hydroxyphenols and their ether or heteroside derivatives, phenolic acids, monomers that are
  • the carotenoids may, for example, be ⁇ -carotene, ⁇ -carotene, lycopene; zeaxanthin; lutein; ataxanthin, bixin, canthaxanthin, cryptoxanthin.
  • the retinoids may be chosen from retinol, retinol esters such as retinol acetate, retinol propionate, retinol caprylate, retinol caprate, retinol palmitate, retinol linoleate, retinol linolenate; retinal, 13-cis-retinoic acid, all-trans-retinoic acid.
  • the carotenoids or the retinoids are thus in a greater stability with respect to the oxidation caused by oxygen and the carotenoids are given greater stability with respect to light and/or to heat.
  • the flavanones may, for example, be naringenin, or hesperetin and its esters such as hesperetin laurate ( « Flavagrum » from Coletica) or glycosyl hesperetin.
  • the flavonols may in particular be kaempferol and quercetol.
  • the isoflavones may, for example, be daidzein and genistein.
  • the coumarins may be chosen from esculoside, visnadine, esculetol, 4-methylesculetol, and the sodium salt of methylesculetin acetate (Permethol from Syphetal).
  • the lignans may in particular be silymarin, nordihydroguaiaretic acid, secoisolariciresinol and matairesinol.
  • the stilbenoids are, for example, resveratrol and its alkoxylated and glycosylated derivatives.
  • the sapogenins are, for example, hederagenin, diosgenin, hecogenin, smilagenin, sarsapogenin and ruscogenin. Use may also be made of plant extracts containing sapogenins (i.e. hydrolyzed saponins).
  • Diosgenin is in particular available from the company Sabinsa under the trade name Diosgenin ® .
  • the plant extracts containing it are essentially extracted from plants of the genus Dioscorea, in particular chosen from the species Dioscorea villosa, Dioscorea opposita and Dioscorea composita.
  • Such an extract is in particular available from the company Active Organics under the trade names Actigen Y ® and Actiphyte Mexican Wild Yam ® .
  • it may be obtained from the company Osst under the trade name Wild Yam P. E. ® , from the company Alban M ⁇ ller under the trade name Extrait sec igname sauvage ® or from Sederma under the reference Dioschol ® .
  • Dioscorea villosa and Dioscorea opposita root extracts are preferred.
  • the pentacyclic triterpenic acids may in particular be glycyrretinic acid, glycyrrhizic acid, betulinic acid, oleanic acid, asiatic acid, madecassic acid, and their heteroside or glycosylated forms.
  • the ⁇ -hydroxy acids may, for example, be salicylic acid and 5-n-octanoylsalicylic acid.
  • the hydroxyphenols and their ether or heteroside derivatives may, for example, be hydroquinone, arbutin, homogentisic acid, gentisic acid, catechol, guaiacol, resorcinol, lucinol and mequinol.
  • the phenolic acids are in particular chosen from coumarinic acid, caffeic acid, rosmarinic acid, ferrulic acid and chlorogenic acid.
  • the monomers that are tanin precursors may, for example, be gallic acid, ellagic acid and extracts of witch hazel.
  • amino sugars are, for example, N-acetylglucosamine and N-acetylgalactosamine.
  • the peptides are, for example, the palmitoyl of glycine-histidine-lysine tripeptide such as that sold under the name « Biopeptide CL » by the company Sederma; the palmitoyl of valine-glycine-valine-alanine-proline-glycine hexapeptide such as that sold under the name « Biopeptide EL » by the company Sederma; the hexapeptide glutamic acid- glutamic acid-methionine-glutamic acid-arginine-argine, the first (N-terminal) being acetylated and the last (C-terminal) being amidated, as sold under the name Argireline by the company Lipotec; the palmitoyl of lysine-threonine-threonine-lysine-serine pentapeptide sold in particular under the name « Matrixyl » by the company Sederma; the N- ⁇ -alanine-L-histidine dipeptide such as
  • the particularly preferred active compounds are adenosine and ellagic acid.
  • the composition may comprise: - ellagic acid and N-(2-hydroxyethyl)urea,
  • compositions used according to the invention are intended for topical application to the skin, especially the skin of a human being, in particular the skin of the face, of the neck and of the body.
  • This physiologically acceptable medium may more particularly consist of water and, optionally, of a physiologically acceptable organic solvent.
  • the physiologically acceptable medium is an aqueous medium
  • it generally has a pH compatible with the skin, preferably ranging from 3 to 9, and better still from 3.5 to 7.5, preferentially from 5 to 7, and more preferentially ranging from 5 to 6.
  • compositions according to the invention may be in any of the pharmaceutical forms conventionally used for topical application, and in particular in the form of aqueous or aqueous-alcoholic solution; of oil-in-water (O/W) or water-in-oil (VWO) or multiple (triple: W/O/W or O/W/O) emulsions, or of aqueous gels.
  • O/W oil-in-water
  • VWO water-in-oil
  • multiple (triple: W/O/W or O/W/O) emulsions or of aqueous gels.
  • the composition is an oil-in-water emulsion.
  • compositions used according to the invention may be more or less fluid and may have the appearance of a white or coloured cream, of an ointment, of a milk, of a lotion, of a serum or of a paste.
  • the cosmetic or dermatological composition of the invention may also contain adjuvants that are usual in the cosmetics or dermatological field, such as oils (in particular oils of animal origin, oils of plant origin, synthetic oils), emulsifiers (in particular non-ionic emulsifiers), geling agents, preserving agents, solvents, fragrances, fillers, UV-screening agents, bactericides, odour absorbers, dyestuffs, salts, or tocopherol esters (or esters of vitamin E) such as tocopheryl acetate, tocopheryl linoleate, the phosphoric diester of vitamin E and C (as sold under the name « Sepivital EPC » by the company Seppic) or tocopheryl nicotinate.
  • oils in particular oils of animal origin, oils of plant origin, synthetic oils
  • emulsifiers in particular non-ionic emulsifiers
  • geling agents preserving agents, solvents, fragrances, fillers, UV-screening agents, bactericides
  • these various adjuvants are those conventionally used in the field under consideration, and are, for example, from 0.01 to 20% of the total weight of the composition. Depending on their nature, these adjuvants can be introduced into the fatty phase or into the aqueous phase.
  • the composition may comprise a preserving agent, in particular chosen from para- hydroxybenzoic acid esters, also called Parabens ® (in particular methyl paraben, ethyl paraben, propyl paraben), phenoxyethanol, compounds that release formol, for instance imidazolidinylurea, or diazolidinylurea, chlorhexidine digluconate, sodium benzoate, caprylyl glycol, iodo propynyl butyl carbamate, pentylene glycol, alkyl trimethylammonium bromide, such as myristyltrimethylammonium bromide (CTFA name: myrtrimonium bromide), dodecyltrimethylammonium bromide, hexadecyl- trimethylammoniuim bromide, and mixtures thereof such as the mixture sold under the name Cetrimide ® by the company FEF Chemicals.
  • Parabens ® in particular methyl paraben, eth
  • the preserving agent may be present in the composition according to the invention in an amount ranging from 0.001 to 10% by weight, relative to the total weight of the com ⁇ position, especially ranging from 0.1 to 5% by weight, and in particular ranging from 0.2 to 3% by weight.
  • the composition according to the invention may be a skincare product, in particular for the face, the neck, the area around the eye, the body; or alternatively, a composition for making up the skin, such as a product of the complexion (in particular a foundation), an eyeshadow, a blusher, an eyeliner, a concealer product, or a body makeup product.
  • the composition is a composition that is not rinsed off.
  • the invention also relates to a cosmetic assembly compris ⁇ ing: i) a container delimiting at least one compartment, said container being closed by means of a closing member; and ii) a composition as defined above and placed inside said compartment.
  • the container may be in any appropriate form. It may in particular be in the form of a bottle, a tube, a jar, a case, a box, a sachet or a carton.
  • the closing member may be in the form of a removable stopper, a lid, a cap, a tear-off strip or a capsule, in particular of the type comprising a body attached to the container and a cover cap articulated on the body. It may also be in the form of a member for se- lectively closing the container, especially a pump, a valve or a flap valve.
  • the container may be combined with an applicator, in particular in the form of a brush comprising an arrangement of bristles maintained by a twisted wire.
  • a twisted brush is described in particular in US patent 4 887 622.
  • It may also be in the form of a comb comprising a plurality of application members, obtained in particular by moulding. Such combs are described, for example, in patent FR 2 796 529.
  • the applicator may be in the form of a fine brush, as described, for example, in patent FR 2 722 380.
  • the ap ⁇ plicator may be in the form of a block of foam or of elastomer, a felt or a spatula.
  • the applicator may be free (tuft or sponge) or securely fastened to a rod worn by the closing member, as described, for example, in US patent 5 492 426.
  • the applicator may be se ⁇ curely fastened to the container, as described, for example, in patent FR 2 761 959.
  • the product may be contained directly in the container, or indirectly.
  • the product may be placed on an impregnated support, in particular in the form of a wipe or of a pad, and placed (individually or in plurality) in a box or in a sachet.
  • an impregnated support in particular in the form of a wipe or of a pad, and placed (individually or in plurality) in a box or in a sachet.
  • Such a support incorporating the product is described, for example, in application WO 01/03538.
  • the closing member may be coupled to the container by screwing.
  • the coupling between the closing member and the container is done other than by screwing, in particular via a bayonet mechanism, by click-fastening, gripping, welding, bonding or by magnetic attraction.
  • click-fastening is intended to mean in particular any system involving the crossing of a bead or cord of material by elastic deformation of a portion, in particular of the closing member, followed by return to the elastically uncon- strained position of said portion after the crossing of the bead or cord.
  • the container may be at least partially made of thermoplastic material.
  • thermoplastic material By way of ex ⁇ amples of thermoplastic materials, mention may be made of polypropylene or polyethyl ⁇ ene.
  • the container is made of non-thermoplastic material, in particular glass or metal (or alloy).
  • the container may have rigid walls or deformable walls, in particular in the form of a tube or a tubular bottle.
  • the container may comprise means intended to bring about or facilitate the distribution of the composition.
  • the container may have deformable walls so as to cause the composition to exit in response to a positive pressure inside the container, this positive pressure being caused by elastic (or non-elastic) squeezing of the walls of the container.
  • the container may consist of a carton with a base delimiting at least one housing con ⁇ taining the composition, and a lid, in particular articulated on the base, and capable of at least partially covering said base.
  • a carton is described, for example, in application WO 03/018423 or in patent FR 2 791 042.
  • the container may be equipped with a drainer arranged in the region of the aperture of the container.
  • a drainer makes it possible to wipe the applicator and possibly the rod to which it may be securely fastened.
  • Such a drainer is described, for example, in patent FR 2 792 618.
  • the amounts are expressed as percentage by weight.
  • the mixture is heated, with moderate stirring, to 75 0 C.
  • Phase B is added to phase A and the mixture is stirred at 75 0 C for 10 minutes. The mixture is cooled to 45 0 C with slow stirring.
  • Phase C Phase C, mixed beforehand, is added and the mixture is cooled to ambient temperature with slow stirring.
  • composition obtained is applied to the skin of the body. After prolonged use, a de ⁇ crease in cellulite and a slimming of the figure are noted.
  • Phase B is heated to approximately 75 0 C; stirring is carried out until a homogeneous gel is obtained.
  • Phase A is heated to approximately 75 0 C.
  • the emulsion is formed by incorporating phase A into phase B.
  • phase C is incorporated, and the stirring is maintained until complete cooling.
  • the composition is applied to the face. After prolonged application, a decrease in the wrinkles and a relaxation of the lines of the face are noted.

Abstract

L'invention concerne une composition comprenant un composé d'urée hydroxylée et un agent actif choisi parmi les agents actifs pour la peau et relaxants, les agents stimulant la synthèse des fibres matricielles extracellulaires dermiques ou épidermiques, ou des fibres situées à la jonction dermique-épidermique ou empêchant leur dégradation, les agents anti-glycation, les agents actifs lipolytiques ou les agents actifs qui inhibent la lipogenèse, les anti-irritants, et des mélanges de ceux-ci. L'invention concerne également une composition comprenant un composé d'urée hydroxylée et un agent actif choisi parmi les caroténoïdes, les rétinoïdes, les flavanones, les flavanoles, les isoflavones, les coumarines, les lignanes, les stilbénoïdes, les sapogénines, les acides pentacycliques triterpéniques, les acides β-hydroxy, les hydroxyphénols et leurs dérivés éther ou hétherosides, les acides phénoliques, les monomères qui sont des précurseurs de tanin, les sucres aminés, les peptides, et des mélanges de ceux-ci. L'invention concerne enfin l'application de la composition pour les soins de la peau et pour son maquillage.
PCT/EP2005/013527 2004-11-04 2005-11-04 Composition cosmetique comprenant un agent actif et un compose d'uree WO2006048339A2 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
FR0452518A FR2877223B1 (fr) 2004-11-04 2004-11-04 Composition cosmetique comprenant un actif et un compose d'uree
FR0452518 2004-11-04
US62728404P 2004-11-15 2004-11-15
US60/627,284 2004-11-15
FR0412368A FR2877221B1 (fr) 2004-11-04 2004-11-22 Composition cosmetique comprenant un actif et un compose d'uree
FR0412368 2004-11-22

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006095098A2 (fr) * 2005-03-11 2006-09-14 L'oreal UTILISATION D'UN EXTRAIT DE BACTERIE FILAMENTEUSE NON FRUCTIFIANTE NON PHOTOSYNTHETIQUE COMME AGENT PROTECTEUR ET/OU ACTIVATEUR DES LYMPHOCYTES ϜδT
US20140228291A1 (en) * 2013-02-11 2014-08-14 Jan Marini Skin Research Post procedure skin care gel and methods of use thereof
US10376557B2 (en) * 2006-06-13 2019-08-13 Helix Biomedix Inc. Peptide fragments for inducing synthesis of extracellular matrix proteins
WO2023077338A1 (fr) * 2021-11-04 2023-05-11 深圳市维琪科技股份有限公司 Dérivé d'hexapeptide et composition cosmétique ou composition pharmaceutique et utilisation associée

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WO2006018198A1 (fr) * 2004-08-13 2006-02-23 Henkel Kommanditgesellschaft Auf Aktien Compositions cosmetiques et dermatologiques a base de (2-hydroxyethyl)uree

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DE2703185A1 (de) * 1977-01-27 1978-08-10 Henkel Kgaa Kosmetische mittel mit einem gehalt an haut-feuchthaltemitteln
WO2006018198A1 (fr) * 2004-08-13 2006-02-23 Henkel Kommanditgesellschaft Auf Aktien Compositions cosmetiques et dermatologiques a base de (2-hydroxyethyl)uree

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006095098A2 (fr) * 2005-03-11 2006-09-14 L'oreal UTILISATION D'UN EXTRAIT DE BACTERIE FILAMENTEUSE NON FRUCTIFIANTE NON PHOTOSYNTHETIQUE COMME AGENT PROTECTEUR ET/OU ACTIVATEUR DES LYMPHOCYTES ϜδT
WO2006095098A3 (fr) * 2005-03-11 2007-04-05 Oreal UTILISATION D'UN EXTRAIT DE BACTERIE FILAMENTEUSE NON FRUCTIFIANTE NON PHOTOSYNTHETIQUE COMME AGENT PROTECTEUR ET/OU ACTIVATEUR DES LYMPHOCYTES ϜδT
US10376557B2 (en) * 2006-06-13 2019-08-13 Helix Biomedix Inc. Peptide fragments for inducing synthesis of extracellular matrix proteins
US20140228291A1 (en) * 2013-02-11 2014-08-14 Jan Marini Skin Research Post procedure skin care gel and methods of use thereof
US9808654B2 (en) * 2013-02-11 2017-11-07 Jan Marini Skin Research Post procedure skin care gel and methods of use thereof
WO2023077338A1 (fr) * 2021-11-04 2023-05-11 深圳市维琪科技股份有限公司 Dérivé d'hexapeptide et composition cosmétique ou composition pharmaceutique et utilisation associée

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