EP1003471A1 - Use of a lipoaminoacid in a cosmetic formulation - Google Patents

Use of a lipoaminoacid in a cosmetic formulation

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Publication number
EP1003471A1
EP1003471A1 EP98940310A EP98940310A EP1003471A1 EP 1003471 A1 EP1003471 A1 EP 1003471A1 EP 98940310 A EP98940310 A EP 98940310A EP 98940310 A EP98940310 A EP 98940310A EP 1003471 A1 EP1003471 A1 EP 1003471A1
Authority
EP
European Patent Office
Prior art keywords
palmitoyl
formula
mixture
acid
glutamic acid
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.)
Withdrawn
Application number
EP98940310A
Other languages
German (de)
French (fr)
Inventor
Corinne Stoltz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Original Assignee
Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA filed Critical Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Publication of EP1003471A1 publication Critical patent/EP1003471A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products 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

Definitions

  • the subject of the present invention is a new use of compounds with a lipoamino acid structure, as well as new synergistic compositions.
  • cosmetic product any substance or preparation intended to be put in contact with the various surface parts of the human body (epidermis, hair and capillary system nails, lips and genitals) or with teeth and oral mucous membranes for the sole or exclusive purpose of cleaning, perfuming, modifying their appearance and / or correct body odors and / or protect or maintain them in good condition.
  • soothing product or formulation will be called any cosmetic product which gives a feeling of well-being of the skin, whether it is in particular a feeling of freshness, softness, elasticity, and / or comfort, felt. by the subject through the application of said product on his skin.
  • Certain cosmetic products thus have the property of protecting the skin against solar irritation, against mechanical irritation and / or against chemical irritation and thus avoiding inflammation thereof.
  • cosmetic formulations comprising as active principles, one or more lipoaminacids, have all at the same time a hydrating activity, a germicidal and antimicrobial activity and an anti-inflammatory activity whether by inhibiting radicals free formed in particular by ultraviolet radiation or by inhibiting enzymes, such as lipases, lipooxygenase, 5-alpha-reductase which is in particular responsible for the production of sebum, elastase and hyaluronidase which are in particular responsible for the degradation of the tissue matrix, and an antagonistic activity of substance P.
  • the subject of the invention is the use of at least one antagonist of substance P in a cosmetic formulation for soothing and / or protecting all types of skin and in particular sensitive skin, characterized in that the antagonist of the substance P is a compound of formula (I):
  • R represents the characterizing chain of a fatty acid, saturated or unsaturated, linear or branched, comprising from 3 to 30 carbon atoms
  • Ri represents a characterizing chain of an amino acid and m is between 1 and 5
  • R 2 represents a hydrogen atom or an alkyl radical containing from 1 to 3 carbon atoms.
  • topically acceptable salt means any salt of the acid of formula (I) which is biologically acceptable for the skin and / or the mucous membranes, ie any salt which can in particular adjust the pH of the composition to a value between 3 and 8 and preferably approximately equal to 5, that is to say at a pH close to that of the skin.
  • alkaline salts such as the sodium, potassium or lithium salts, alkaline earth salts such as the calcium, magnesium or strontium salts; it can also be metallic salts such as divalent zinc or manganese salts or alternatively trivalent salts of iron, lantanum, cerium or aluminum.
  • the compound of formula (I) present in the composition which is the subject of the present invention may be in the form of free acid or in the form of partially or totally salified.
  • characterizing chain used in the context of the present application designates the non-functional main chain of the fatty acid or of the amino acid considered.
  • the characterizing chain will be the chain represented by R.
  • the radical R represents in particular a radical comprising from 5 to 22 carbon atoms chosen from the pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl radicals , unicosyle, docosyle, heptadécènyle, eicosènyle, uneicosènyle, docosènyle ou heptadécadiènyle ou strictlynyle.
  • R - CO fragment contains from 7 to 22 carbon atoms and represents in particular one of the hexanoyl, heptanoyl radicals, octanoyl (capryloyl), decanoyl (caproyl), undecylenoyl, dodecanoyl (lauroyle), tetradecanoyl (myristyle), hexadecanoyle (palmitoyle), octadecanoyl (stearoyl, eicosanoyle (arachidoyle), docosanoyle (arachidoyle), docosanoyle (arachidoyle) , docosenoyl (erucyle), octadecadienoyl (linolenoyl)
  • the formula (erucyle) in the formula (I)
  • the R-CO fragment (I) contains from 10 to 18 carbon atoms, and, more particularly, a lauroyl radical or a palmitoyl radical.
  • Ri represents in particular the characterizing chain of one of the amino acids chosen from glycine, alanine, serine, aspartic acid, glutamic acid, valine, threonine, arginine, lysine, proline, leucine, phenylalanine, isoleucine, phistidine, tyrosine, tryptophan, asparagine, cysteine, cystine, methionine, hydroxyproline, hydroxylysine, ornithine and sarcosine.
  • amino acids chosen from glycine, alanine, serine, aspartic acid, glutamic acid, valine, threonine, arginine, lysine, proline, leucine, phenylalanine, isoleucine, phistidine, tyrosine, tryptophan, asparagine, cysteine, cystine, methionine, hydroxyproline, hydroxylysine, ornithine
  • the cosmetic formulation according to the invention may contain one or more of these compounds.
  • the compounds of formula (I) are generally obtained by acylation of compounds of formula (F) (F)
  • proteins of all origins can be of animal origin, such as, for example, collagen, elastin, fish flesh protein, fish gelatin, keratin or casein, of vegetable origin, such as, for example , those from soy, sunflower, oats, wheat, corn, barley, potato, lupine, horse bean, sweet almond, silk, or obtained from chorelles (unicellular algae), pink algae or yeast.
  • This hydrolysis can be carried out, for example, by heating at a temperature between 60 and 130 ° C. a protein placed in an acidic or alkaline medium.
  • This hydrolysis can also be carried out enzymatically with a protease, optionally coupled to an alkaline or acid post-hydrolysis.
  • the cosmetic formulation as defined above comprises as active principle, at least one of the compounds chosen from lauroyl alanine, lauroyl lysine, lauroyl aspartic acid, lauroyl glutamic acid, l palmitoyl glutamic acid, stearoyl glutamic acid, palmitoyl proline or palmitoyl sarcosine or their topically acceptable salts and, more particularly, the cosmetic formula comprises as active principle the mixture N-palmitoyl proline and N-palmitoyl glutamic acid or their salts topically acceptable or the mixture N-palmitoyl proline, N-palmitoyl glutamic acid and N-palmitoyl sarcosine (or their topically acceptable salts).
  • the cosmetic formulation may also contain zinc gluconate and / or mixed potassium and magnesium aspartate.
  • the acylation reaction allowing the abovementioned compounds of formula (I) to be obtained can be carried out chemically in an alkaline medium (pH 8 to 10) according to the reaction of
  • the currently preferred embodiment for the preparation of the lipoamino acid compounds of formula (I) comprises the following steps: a) Acylation in an alkaline medium (pH 8 to 10) of an excess mixture of amino acids (mixture extemporaneous or obtained by complete hydrolysis of a protein) with a fatty acid (or a mixture of fatty acids), in the form of acid chloride or anhydride.
  • the compounds of formula (I) are obtained from a cut of Copra oil (Coco oil), palm kern oil, palm oil or beef tallow.
  • the amino acid / acid chloride ratio is preferably 1.05 to 1.30 equivalents.
  • the optimal acylation temperature is around 80 ° C but varies from one amino acid to another between 60 and 110 ° C.
  • the duration of acylation depends on the equipment used (size, agitation); it is approximately 2 hours for an acylated mass of 500 kg and approximately 5 hours for an acylated mass of 5,000 kg.
  • the cosmetic formulation is usually in the form of an aqueous solution, a dilute alcoholic solution, or a single or multiple emulsion, such as a water in oil (EH), oil in water (O / W) emulsion. or water in oil in water
  • EH water in oil
  • O / W oil in water
  • W / O E Mention may be made, for example, of creams, milks, lotions, wipes, gels such as shower gels, oils, soaps, liquid soaps, syndets, intimate hygiene products, or shampoos.
  • This formulation is prepared by mixing, by one or more steps of methods known to those skilled in the art, the cosmetic active ingredient (s), comprising the active ingredient (s) of formula (I) as defined above with the cosmetic excipients.
  • the present invention also relates to cosmetic active agents comprising, as active principle, from 15% to 60% and, more particularly, 20% to 40% by weight of a mixture of compounds of formula (I) as defined previously chosen from the following mixtures:
  • -N-palmitoyl proline and N-palmitoyl glutamic acid or a mixture of their topically acceptable salts
  • -N-palmitoyl proline, N-palmitoyl glutamic acid and N-palmitoyl sarcosine or a mixture of their topically acceptable salts.
  • the formulation is in the form of an oil-in-water emulsion having the appearance of a milk having a viscosity of less than 1 Pa.s. comprising as emulsifier a self-emulsifiable composition based on fatty alcohols.
  • the cosmetic formulation comprises, as active principle antagonist of substance P, from 0.001% to 6% by weight of at least one compound of formula (I) and if desired up to 5% zinc gluconate and / or up to 5% mixed potassium and magnesium aspartate.
  • the invention particularly relates to the use as defined above for which the formulation cosmetic comprises, as active principle antagonist of substance P, from 0.5% to 2% by weight of a compound of formula (I) and if desired from 0.025% to 0.2% of zinc gluconate, and the use as defined above for which the cosmetic formulation comprises, as active principle antagonist of substance P from 0.001% to 0.005% by weight of at least one compound of; formula (I) and if desired from 0.0001% to 0.0005% zinc gluconate.
  • a cosmetic formulation as defined above further comprising a product of surface abrasion of the skin.
  • surface abrasion product of the skin is meant in particular the exfoliating agents and the agents causing the cell renewal of the skin; as examples of such agents, mention may be made of alpha and beta-hydroxy acids such as lactic, glycolic or salicylic acids, alpha-keto acids such as pyruvic acid, as well as acetic acid, trichloacetic acid, l-pyrrolidone-5-carboxylic acid, capryloyl salicylic acid, alpha-hydroxy decanoic acid, alpha-hydroxy octanoic acid, gluconolactone, methoxy gluconamide, oxalic acid, l , malic acid, tartaric acid, mandelic acid, benzylic acid, gluconic acid, peroxides, phenols and retinoids.
  • alpha and beta-hydroxy acids such as lactic, glycolic or salicylic acids,
  • Example 1 Determination of the antagonistic properties of substance P.
  • Proteol SAV 50 S Cocoyl amino acid Proteol OAT Cocoyl oat amino acids Proteol LW30 Cocoyl w eat amino acids Proteol VS 22 Cocoyl Soya amino acids ORAMIX L 30 Cocoyl sodium sarcosinate MONTEUSE LCT Lauroyl collagen amino acids Proteol CO Cocoyl collagen amino acids.
  • composition A a composition comprising, as active principle, from 15% to 40% by weight of at least one compound of formula (I), the following cosmetic formulations were prepared:
  • Composition A 3%
  • SEPIGEL ® 501 is a thickening agent based on acrylamide copolymers sold by the company SEPPIC
  • Composition A 3%
  • Perfluoropolymethylisopropylether 0.5% stearyl alcohol: 1% stearic alcohol: 0.5% preservative: 0.65%
  • a Composition A 3% SEPIGEL ® 501: 1.5% water: qs 100%
  • SEPICIDE ® CI 0.50% Perfume: 0.20% ethanol 95 °: 10.0%
  • MIROPEARL ® M 100 is an ultra-fine powder with a very soft touch and matifying action sold by the company MATSUMO
  • SEPICIDE ® CI imidazolin urea, is a preservative marketed by the company SEPPIC
  • PROCEDURE Add B to A.
  • SEPICIDE ® CI 0.3%
  • SEPICIDE ® HB 0.5%
  • Sodium pyrolidinone carboxylate 1% (hydrating agent) (SIMULSOL ® 165 (glycerol stearate / PEGIOO stearate) is a self-emulsifying composition sold by the company SEPPIC)
  • LANOL ® 1688 is a non-greasy emollient ester marketed by the company SEPPIC
  • LANOL 14M and LANOL ® S are consistency factors sold by the company SEPPIC
  • SEPICIDE ® HB (mixture of phenoxyethanol / methyl paraben / ethylparaben / propylparaben / butylparaben), is a preservative sold by the company SEPPIC)
  • Example 6 Body milk FORMULA
  • Composition A 3% SEPIGEL ® 501: 0.35%
  • SEPICIDE ® HB 0.5% fragrance: 0.20%
  • SIMULSOL ® 165 5.0% LANOL ® 1688: 20.0% LANOL ® P: 1.0% (additive with stabilizing effect)
  • Composition A 3% SEPIGEL ® 501: 2.5%
  • LANOL ® P is an additive with stabilizing effect marketed by the company SEPPIC
  • PROCEDURE Introduce B into A at around 75 ° C; add C around 60 ° C, then D around 45 ° C
  • Example 8 non-greasy sun gel FORMULA
  • a Composition A 3% 0 SEPIGEL ® 501: 0.8% water: 30%
  • SEPICIDE ® HB 0.30% fragrance: 0.10%
  • PARSOL ® MCX is octyl paramethoxycinnamate; it is marketed by the company GIVAUDAN)
  • PROCEDURE Introduce B into A; add C, then D, then E.
  • SEPIPERL ® N is a pearling agent, marketed by the company SEPPIC, based on a mixture of alkyl polyglucosides such as those described in WO 95/13863
  • composition A 3%
  • composition A 3%
  • SEPICIDE ® HB 0.30% fragrance: 0.05%
  • LANOL ® 1688 2% (MICROPEARL ® SQL is a mixture of microparticles containing squalane which is released under the action of massage; it is marketed by the company MATSUMO)
  • Example 12 Brightening Gel FORMULA A Composition A: 3%
  • PROCEDURE Melt A at around 75 ° C. Emulsify B in A at 75 ° C then add C around 60 ° C, then D
  • Example 14 Make-up removing emulsion with sweet almond oil FORMULA MONTANOV ® 68: 5% sweet almond oil: 5% water: qsp100% O 99/04757 18
  • Composition A 1% SEPIGEL ® 501: 0.3% glycerin: 5% preservative: 0.2% perfume: 03%
  • Composition A 2%
  • SEPICIDE ® HB 0.8 fragrance: 03%
  • Composition A 0.1 to 5%
  • SEPIGEL ® 501 1.5% gluconic acid: 1.50% triethylamine: 0.9% SEPICIDE ® HB: 0.3%
  • Composition A 3%
  • SEPIGEL ® 501 2.5%
  • SEPICIDE ® HB 0.3%
  • SEPICIDE ® CI 0.2% fragrance: 0.4% dye: 0.03%
  • Composition A 2% SEPIGEL ® 501: 0.8% preservative: 0.2%
  • Example 20 Body milk FORMULA
  • Composition A 2%
  • SEPIGEL ® 501 0.8% preservative: 0.2% fragrance: 0.4%
  • LANOL ® 37T is glyceroltriheptanoate, marketed by Seppic).
  • SOLAGUM ® L is a carrageenan sold by the company SEPPIC).
  • Composition A 4%
  • SEPIGEL ® 501 1.5%
  • MARCOL ® 82 is a paraffin oil sold by the company ESSO
  • Composition A 3%
  • SEPIGEL ® 501 1.2% preservative: 0.2% perfume: 0.4%
  • LANOL ® 84D is dioctylmalate sold by the company SEPPIC).
  • EUSOLEX ® 4360 2.0% water: qsp100%
  • Composition A 3%
  • SEPIGEL ® 501 1.8% preservative: 0.2% perfume: 0.4%
  • PARSOL NOX ® and the EUSOLEX ® 4360 are two sun filters marketed respectively by the companies GIVAUDAN and MERCK).
  • Example 25 leave-in care composition FORMULA
  • Composition A 3%
  • DOW CORNING ® 245 FLuid is cyclomethicone, sold by the company DOW CORNING:
  • Composition A 5%
  • Composition A 3% SEPIGEL ® 305: 2%
  • Composition A 3%
  • Composition A 3%
  • SEPIGEL ® 600 2% isohexadecane 5% borage oil 1%
  • SEPIGEL ® 600 is a thickening agent based on acrylamide copolymers sold by the company SEPPIC
  • Example 30 Soothing After Sun Care
  • Composition A 3%
  • SEPIGEL ® 501 4% cyclomethicone and dimethiconol: 5%
  • LANOL ® 189 is a rich and silky touch ester, marketed by the company SEPPIC).
  • Composition A 3%
  • Isostearyl isostearate 5%
  • MICROPEARL ® M305 1% glycerin: 10%
  • MECROPEARL ® M305 is a crosslinked copolymer of polymethyl methacrylate is sold by the company MATSUMO).
  • Isostearyl isostearate 5% Dimethicone: 10% water: qsp100% Composition A: 2% SEPIGEL ® 305: 1% SEPICIDE ® HB: 0.3% SEPICIDE ® CI: 0.2% perfume: 0.2%
  • Example 33 self-tanning care composition A: 3% DHA 1% Sepigel ® 305: 2%

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

The invention concerns the use of at least an antagonist of the substance P in a cosmetic formulation for soothing and/or protecting all types of skin and, in particular, sensitive skin, characterised in that the antagonist of substance P is a compound of formula (I) or its topically acceptable salts, in which: R represents the characterising chain of a fatty acid, saturated or unsaturated, linear or branched, comprising 3 to 30 carbon atoms; R1 represents a characterising chain of an amino acid and m ranges between 1 and 5.

Description

UTILISAΉON DE LIPOAMINOACIDE DANS UNE FORMULAΗON COSMETIQUE USE OF LIPOAMINOACID IN A COSMETIC FORMULA
La présente invention a pour objet une nouvelle utilisation de composés à structure lipoaminoacide, ainsi que de nouvelles compositions synergiques.The subject of the present invention is a new use of compounds with a lipoamino acid structure, as well as new synergistic compositions.
Les composés à structure lipoaminoacide, comme par exemple ceux décrits dans les demandes internationales de brevet publiées sous les numéros WO92/20647, WO92/21318, WO94/26694 et WO94/27561, sont, en raison de leur structure amphiphile, des vecteurs biologiques particulièrement intéressants en tant que régulateurs de la physiologie cutanée et s'avèrent appropriés à de multiples applications, notamment en cosmétique. Selon la directive du Conseil de la Communauté Economique EuropéenneCompounds with a lipoamino acid structure, such as for example those described in international patent applications published under the numbers WO92 / 20647, WO92 / 21318, WO94 / 26694 and WO94 / 27561, are, because of their amphiphilic structure, particularly biological vectors interesting as regulators of skin physiology and prove to be suitable for multiple applications, in particular in cosmetics. According to the directive of the Council of the European Economic Community
N°76/768/ CEE du 27 juillet 1976 modifiée par la directive N°93/35/CEE du 14 juin 1993, on entend par " produit cosmétique " toute substance ou préparation destinée à être mise en contact avec les diverses parties superficielles du corps humain (épiderme, système pileux et capillaire ongles, lèvres et organes génitaux) ou avec les dents et les muqueuses buccales en vue, exclusivement ou principalement, de les nettoyer, de les parfumer, d'en modifier l'aspect et/ou de corriger les odeurs corporelles et/ou de les protéger ou de les maintenir en bon état.N ° 76/768 / CEE of July 27, 1976 modified by the directive N ° 93/35 / CEE of June 14, 1993, one understands by "cosmetic product" any substance or preparation intended to be put in contact with the various surface parts of the human body (epidermis, hair and capillary system nails, lips and genitals) or with teeth and oral mucous membranes for the sole or exclusive purpose of cleaning, perfuming, modifying their appearance and / or correct body odors and / or protect or maintain them in good condition.
Du fait de la plus en plus grande prise en compte des problèmes de pollution liés à la vie moderne, notamment dans les lieux fortement urbanisés, l'aspect protection de la peau est devenu prépondérant dans la recherche de nouveaux produits cosmétiques. En réponse aux agressions ou aux sensations d'agression de la peau, on a développé le concept de produit cosmétique apaisant.Due to the increasing consideration of pollution problems linked to modern life, especially in highly urbanized places, the skin protection aspect has become preponderant in the search for new cosmetic products. In response to aggressions or feelings of aggression on the skin, we developed the concept of a soothing cosmetic product.
On appellera dans l'exposé suivant, produit ou formulation apaisant, tout produit cosmétique qui procure une sensation de bien-être de la peau, que ce soit notamment une sensation de fraîcheur de douceur, d'élasticité, et/ou de réconfort, ressentie par le sujet grâce à l'application dudit produit sur sa peau. Certains produits cosmétiques présentent ainsi la propriété de protéger la peau contre l'irritation solaire, contre l'irritation mécanique et ou contre l'irritation chimique et ainsi d'éviter les inflammations de celle-ci.In the following description, soothing product or formulation will be called any cosmetic product which gives a feeling of well-being of the skin, whether it is in particular a feeling of freshness, softness, elasticity, and / or comfort, felt. by the subject through the application of said product on his skin. Certain cosmetic products thus have the property of protecting the skin against solar irritation, against mechanical irritation and / or against chemical irritation and thus avoiding inflammation thereof.
D'autres comme ceux décrits la demande de brevet européen publiée sous le numéro EP 0 680 749, présentent la propriété de soulager les sensations dysesthesiques, voire douloureuses, de part leur propriété d'antagonistes de la substances P, qui conduit à une sorte d'analgésie périphérique. Cependant cette propriété n'est mise en évidence que sur un certain type de peaux, celles réagissant à une application topique de capsaïcine, selon un test décrit dans ladite demande de brevet. Or, la demanderesse a trouvé de façon inattendue que les formulations cosmétiques comprenant comme principes actifs, un ou plusieurs lipoaminacides, possédaient toute à la fois une activité hydratante, une activité germicide et anti-microbienne et une activité antiinflammatoire que ce soit en inhibant les radicaux libres formés notamment par le rayonnement ultraviolet ou en inhibant des enzymes, tels que les lipases, la lipooxygènase, la 5-alpha-réductase qui est notamment responsable de la production de sébum, l' elastase et la hyaluronidase qui sont notamment responsables de la dégradation de la matrice tissulaire, et une activité antagoniste de la substance P. Elle a de plus découvert que le caractère apaisant tel que défini précédemment n'était pas ressentie spécifiquement sur un seul type de peaux, celles réagissant à une application topique de capsaïcine, mais sur tous les types de peaux. L'invention a pour objet l'utilisation d'au moins un antagoniste de la substance P dans une formulation cosmétique pour apaiser et/ou protéger tous les types de peaux et notamment les peaux sensibles, caractérisée en ce que l'antagoniste de la substance P est un composé de formule (I):Others, such as those described in the European patent application published under the number EP 0 680 749, have the property of relieving dysesthesic or even painful sensations, due to their property of antagonists of substances P, which leads to a kind of analgesia. However, this property is only demonstrated on a certain type of skin, those reacting to a topical application of capsaicin, according to a test described in said patent application. However, the Applicant has unexpectedly found that cosmetic formulations comprising as active principles, one or more lipoaminacids, have all at the same time a hydrating activity, a germicidal and antimicrobial activity and an anti-inflammatory activity whether by inhibiting radicals free formed in particular by ultraviolet radiation or by inhibiting enzymes, such as lipases, lipooxygenase, 5-alpha-reductase which is in particular responsible for the production of sebum, elastase and hyaluronidase which are in particular responsible for the degradation of the tissue matrix, and an antagonistic activity of substance P. It further discovered that the soothing nature as defined above was not felt specifically on a single type of skin, those reacting to a topical application of capsaicin, but on all skin types. The subject of the invention is the use of at least one antagonist of substance P in a cosmetic formulation for soothing and / or protecting all types of skin and in particular sensitive skin, characterized in that the antagonist of the substance P is a compound of formula (I):
R-CO- (N(R2>— CH— CO)m— O— H (I)R-CO- (N (R 2 > - CH— CO) m - O— H (I)
\ I\ I
' Rι ou ses sels topiquement acceptables, ou un mélange desdits composés ou de leurs sels. dans laquelle R représente la chaîne caractérisante d'un acide gras, saturé ou insaturé, linéaire ou ramifié, comportant de 3 à 30 atomes de carbone, Ri représente une chaîne caractérisante d'un acide aminé et m est compris entre 1 et 5, et R2 représente un atome d'hydrogène ou un radical alkyle comportant de 1 à 3 atomes de carbone.'Rι or its topically acceptable salts, or a mixture of said compounds or their salts. in which R represents the characterizing chain of a fatty acid, saturated or unsaturated, linear or branched, comprising from 3 to 30 carbon atoms, Ri represents a characterizing chain of an amino acid and m is between 1 and 5, and R 2 represents a hydrogen atom or an alkyl radical containing from 1 to 3 carbon atoms.
Par sel topiquement acceptable, on entend tout sel de l'acide de formule (I) biologiquement acceptable pour la peau et/ou les muqueuses, c'est à dire tout sel pouvant notamment régler le pH de la composition à une valeur comprise entre 3 et 8 et de préférence environ égale à 5, c'est à dire à un pH voisin de celui de la peau.The term “topically acceptable salt” means any salt of the acid of formula (I) which is biologically acceptable for the skin and / or the mucous membranes, ie any salt which can in particular adjust the pH of the composition to a value between 3 and 8 and preferably approximately equal to 5, that is to say at a pH close to that of the skin.
Il peut s'agir notamment de sels alcalins tels que les sels de sodium, de potassium ou de lithium, de sels alcalino-terreux tels que les sels de calcium, de magnésium ou de strontium; il peut aussi s'agir de sels métalliques tels que les sels divalents de zinc ou de manganèse ou encore les sels trivalents de fer, de lantane, de cérium ou d'aluminium.They may especially be alkaline salts such as the sodium, potassium or lithium salts, alkaline earth salts such as the calcium, magnesium or strontium salts; it can also be metallic salts such as divalent zinc or manganese salts or alternatively trivalent salts of iron, lantanum, cerium or aluminum.
Le composé de formule (I) présent dans la composition objet de la présente invention, peut être sous forme d'acide libre ou sous forme partiellement ou totalement salifiée.The compound of formula (I) present in the composition which is the subject of the present invention, may be in the form of free acid or in the form of partially or totally salified.
L'expression " chaîne caractérisante " utilisée dans le cadre de la présente demande désigne la chaîne principale non fonctionnelle de l'acide gras ou de l'acide aminé considéré. Ainsi, pour un acide gras répondant à la formule générale R-COOH, la chaîne caractérisante sera la chaîne représentée par R.The expression "characterizing chain" used in the context of the present application designates the non-functional main chain of the fatty acid or of the amino acid considered. Thus, for a fatty acid corresponding to the general formula R-COOH, the characterizing chain will be the chain represented by R.
Le radical R représente notamment un radical comportant de 5 à 22 atomes de carbone choisi parmi les radicaux pentyle, hexyle, heptyle, octyle, nonyle, décyle, undécyle, dodécyle, tridécyle, tétradécyle, pentadécyle, hexadécyle, heptadécyle, octadécyle, nonadécyle, eicosyle, uneicosyle, docosyle, heptadécènyle, eicosènyle, uneicosènyle, docosènyle ou heptadécadiènyle ou décènyle.The radical R represents in particular a radical comprising from 5 to 22 carbon atoms chosen from the pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl radicals , unicosyle, docosyle, heptadécènyle, eicosènyle, uneicosènyle, docosènyle ou heptadécadiènyle ou décènyle.
L'invention a plus particulièrement pour objet l'utilisation telle que définie précédemment pour laquelle, dans la formule (I), le fragment R — CO comporte de 7 à 22 atomes de carbone et représente notamment l'un des radicaux hexanoyle, heptanoyle, octanoyle (capryloyle), décanoyle (caproyle), undécylènoyle, dodécanoyle (lauroyle), tétradécanoyle (myristyle), hexadécanoyle (palmitoyle), octadécanoyle (stéaroyle, eicosanoyle (arachidoyle), docosanoyle (behènoyle), octodécènoyle (oléyle), éicosènoyle (gadoloyle), docosènoyle (érucyle), octadécadiènoyle (linolènoyle). Dans une première variante particulière de la présente invention, dans la formuleA more particular subject of the invention is the use as defined above for which, in formula (I), the R - CO fragment contains from 7 to 22 carbon atoms and represents in particular one of the hexanoyl, heptanoyl radicals, octanoyl (capryloyl), decanoyl (caproyl), undecylenoyl, dodecanoyl (lauroyle), tetradecanoyl (myristyle), hexadecanoyle (palmitoyle), octadecanoyl (stearoyl, eicosanoyle (arachidoyle), docosanoyle (arachidoyle), docosanoyle (arachidoyle) , docosenoyl (erucyle), octadecadienoyl (linolenoyl) In a first particular variant of the present invention, in the formula
(I), le fragment R-CO (I) comporte de 10 à 18 atomes de carbone, et, plus particulièrement, un radical lauroyle ou un radical palmitoyle. Pour un acide aminé représenté par la formule générale(I), the R-CO fragment (I) contains from 10 to 18 carbon atoms, and, more particularly, a lauroyl radical or a palmitoyl radical. For an amino acid represented by the general formula
HN(R2)-CHR COOH, la chaîne caractérisante sera la chaîne représentée par Ri.HN (R 2 ) -CHR COOH, the characterizing chain will be the chain represented by Ri.
Ri représente notamment la chaîne caractérisante d'un des acides aminés choisis parmi la glycine, l'alanine, la serine, l'acide aspartique, l'acide glutamique, la valine, la thréonine, l'arginine, la lysine, la proline, la leucine, la phénylalanine, l'isoleucine, Phistidine, la tyrosine, le tryptophane, l'asparagine, la cystéine, la cystine, la méthionine, Phydroxyproline, l'hydroxylysine, l'ornithine et la sarcosine.Ri represents in particular the characterizing chain of one of the amino acids chosen from glycine, alanine, serine, aspartic acid, glutamic acid, valine, threonine, arginine, lysine, proline, leucine, phenylalanine, isoleucine, phistidine, tyrosine, tryptophan, asparagine, cysteine, cystine, methionine, hydroxyproline, hydroxylysine, ornithine and sarcosine.
Pour un acide aminé représenté par la formuleFor an amino acid represented by the formula
HN-CH-COOH LHN-CH-COOH L
La chaîne caractérisante sera le cycle représenté The characterizing chain will be the cycle represented
Par au moins un composé de formule (I), on indique que la formulation cosmétique selon l'invention peut contenir un ou plusieurs de ces composés.By at least one compound of formula (I), it is indicated that the cosmetic formulation according to the invention may contain one or more of these compounds.
Les composés de formule (I) sont généralement obtenus par acylation de composés de formule (F) (F)The compounds of formula (I) are generally obtained by acylation of compounds of formula (F) (F)
ou de leur sels, eux-mêmes obtenus par hydrolyse totale ou partielle de protéines de toutes origines. Ces protéines peuvent être d'origine animale, telles que, par exemple, le collagène, l'élastine, la protéine de chair de poissons, la gélatine de poissons, la kératine ou la caséine, d'origine végétale, telles que, par exemple, celles issues du soja, du tournesol, de l'avoine, du blé, du maïs, de l'orge, de la pomme de terre, du lupin, de la féverolle, de l'amande douce, de la soie, ou encore obtenues à partir de chorelles (algues unicellulaires), d'algues roses ou de levures. Cette hydrolyse peut être réalisée par exemple par chauffage à des températures comprises entre 60 et 130°C d'une protéine placée dans un milieu acide ou alcalin. Cette hydrolyse peut également être réalisée par voie enzymatique avec une protéase, couplée éventuellement à une post-hydrolyse alcaline ou acide.or their salts, themselves obtained by total or partial hydrolysis of proteins of all origins. These proteins can be of animal origin, such as, for example, collagen, elastin, fish flesh protein, fish gelatin, keratin or casein, of vegetable origin, such as, for example , those from soy, sunflower, oats, wheat, corn, barley, potato, lupine, horse bean, sweet almond, silk, or obtained from chorelles (unicellular algae), pink algae or yeast. This hydrolysis can be carried out, for example, by heating at a temperature between 60 and 130 ° C. a protein placed in an acidic or alkaline medium. This hydrolysis can also be carried out enzymatically with a protease, optionally coupled to an alkaline or acid post-hydrolysis.
Quand m est supérieur à 1, Ri représente plusieurs des chaînes caractérisantes des acides aminés, selon la protéine hydrolysée et le degré d'hydrolyse. Dans une variante préférée de la présente invention, la formulation cosmétique telle que définie précédemment, comprend comme principe actif, au moins un des composés choisis parmi le lauroyl alanine, le lauroyl lysine, l'acide lauroyl aspartique, l'acide lauroyl glutamique, l'acide palmitoyl glutamique, l'acide stéaroyl glutamique, le palmitoyl proline ou la palmitoyl sarcosine ou leurs sels topiquement acceptables et, plus particulièrement, la formule cosmétique comprend comme principe actif le mélange N-palmitoyl proline et acide N-palmitoyl glutamique ou leurs sels topiquement acceptables ou le mélange N-palmitoyl proline, acide N-palmitoyl glutamique et N-palmitoyl sarcosine (ou leurs sels topiquement acceptables).When m is greater than 1, Ri represents several of the characterizing chains of amino acids, depending on the hydrolyzed protein and the degree of hydrolysis. In a preferred variant of the present invention, the cosmetic formulation as defined above, comprises as active principle, at least one of the compounds chosen from lauroyl alanine, lauroyl lysine, lauroyl aspartic acid, lauroyl glutamic acid, l palmitoyl glutamic acid, stearoyl glutamic acid, palmitoyl proline or palmitoyl sarcosine or their topically acceptable salts and, more particularly, the cosmetic formula comprises as active principle the mixture N-palmitoyl proline and N-palmitoyl glutamic acid or their salts topically acceptable or the mixture N-palmitoyl proline, N-palmitoyl glutamic acid and N-palmitoyl sarcosine (or their topically acceptable salts).
La formulation cosmétique peut contenir en outre du gluconate de zinc et/ou de l'aspartate mixte de potassium et de magnésium.The cosmetic formulation may also contain zinc gluconate and / or mixed potassium and magnesium aspartate.
La réaction d'acylation permettant d'obtenir les composés de formule (I) précitée peut être réalisée par voie chimique en milieu alcalin (pH de 8 à 10) selon la réaction deThe acylation reaction allowing the abovementioned compounds of formula (I) to be obtained can be carried out chemically in an alkaline medium (pH 8 to 10) according to the reaction of
Schotten Bauman ou par voie enzymatique et l'homme de métier pourra se reporter notamment à la référence Surfactant Science Séries, volume 7, Anionic Surfactants, partie II, chapitre 16, pages 581 à 617 (Marcel Dekker - 1976).Schotten Bauman or by an enzymatic route and a person skilled in the art may refer in particular to the reference Surfactant Science Series, volume 7, Anionic Surfactants, part II, chapter 16, pages 581 to 617 (Marcel Dekker - 1976).
D'une façon générale, le mode de réalisation actuellement préféré pour la préparation des composés lipoaminoacides de formule (I) comprend les étapes suivantes : a) Acylation en milieu alcalin (pH 8 à 10) d'un excès de mélange d'acides aminés (mélange extemporané ou obtenu par hydrolyse complète d'une protéine) par un acide gras (ou un mélange d'acides gras), sous forme de chlorure d'acide ou d'anhydride.In general, the currently preferred embodiment for the preparation of the lipoamino acid compounds of formula (I) comprises the following steps: a) Acylation in an alkaline medium (pH 8 to 10) of an excess mixture of amino acids (mixture extemporaneous or obtained by complete hydrolysis of a protein) with a fatty acid (or a mixture of fatty acids), in the form of acid chloride or anhydride.
Selon une autre variante particulière de la présente invention, les composés de formule (I) sont obtenus à partir d'une coupe d'huile de Copra (Coco oil), d'huile de palmiste (palm kern oil), d'huile de palme (palm oil) ou de suif de boeuf (beef tallow).According to another particular variant of the present invention, the compounds of formula (I) are obtained from a cut of Copra oil (Coco oil), palm kern oil, palm oil or beef tallow.
Le rapport acides aminés/chlorure acide est de préférence de 1,05 à 1,30 équivalents.The amino acid / acid chloride ratio is preferably 1.05 to 1.30 equivalents.
La température d'acylation optimale se situe vers 80° C mais varie d'un acide aminé à l'autre entre 60 et 110° C. La durée d'acylation dépend de l'équipement utilisé (taille, agitation); elle est de 2 heures environ pour une masse acylée de 500 kg et de 5 heures environ pour une masse acylée de 5 000 kg. b) Cassage de l'acylat alcalin par acidification pour décanter les impuretés solubles dans l'eau et relarguer l'acylat organique acide (pH optimal de 0,5 à 3 selon les acides aminés). c) Purification par lavage à l'eau ou avec addition d'électrolytes ou de co-solvant pour favoriser la décantation.The optimal acylation temperature is around 80 ° C but varies from one amino acid to another between 60 and 110 ° C. The duration of acylation depends on the equipment used (size, agitation); it is approximately 2 hours for an acylated mass of 500 kg and approximately 5 hours for an acylated mass of 5,000 kg. b) Breakage of the alkaline acylate by acidification to decant the water-soluble impurities and release the organic acid acylate (optimal pH 0.5 to 3 depending on the amino acids). c) Purification by washing with water or with the addition of electrolytes or co-solvent to promote decantation.
La formulation cosmétique se présente habituellement sous forme d'une solution aqueuse, d'une solution alcoolique diluée, ou d'une émulsion simple ou multiple, telle qu'une émulsion eau dans huile (E H), huile dans eau (H/E) ou eau dans huile dans eauThe cosmetic formulation is usually in the form of an aqueous solution, a dilute alcoholic solution, or a single or multiple emulsion, such as a water in oil (EH), oil in water (O / W) emulsion. or water in oil in water
(E/H E). On peut citer, par exemple les crèmes, les laits, les lotions, les lingettes, les gels tels que les gels douches, les huiles, les savons, les savons liquides, les syndets, les produits d'hygiène intime, ou les shampooings. Cette formulation est préparée en mélangeant par une ou plusieurs étapes des méthodes connues de l'homme du métier le ou les actifs cosmétiques, comprenant le ou les principes actifs de formule (I) telle que définie précédemment avec les excipients cosmétiques.(W / O E). Mention may be made, for example, of creams, milks, lotions, wipes, gels such as shower gels, oils, soaps, liquid soaps, syndets, intimate hygiene products, or shampoos. This formulation is prepared by mixing, by one or more steps of methods known to those skilled in the art, the cosmetic active ingredient (s), comprising the active ingredient (s) of formula (I) as defined above with the cosmetic excipients.
La présente invention a aussi pour objet les actifs cosmétiques comprenant, à titre de principe actif, de 15 % à 60 % et, plus particulièrement, 20 % à 40 % en poids d'un mélange de composés de formule (I) telle que définie précédemment, choisi parmi les mélanges suivants :The present invention also relates to cosmetic active agents comprising, as active principle, from 15% to 60% and, more particularly, 20% to 40% by weight of a mixture of compounds of formula (I) as defined previously chosen from the following mixtures:
-N-palmitoyl proline et acide N-palmitoyl glutamique, ou un mélange de leurs sels topiquement acceptables, -N-palmitoyl proline, acide N-palmitoyl glutamique et N-palmitoyl sarcosine, ou un mélange de leurs sels topiquement acceptables.-N-palmitoyl proline and N-palmitoyl glutamic acid, or a mixture of their topically acceptable salts, -N-palmitoyl proline, N-palmitoyl glutamic acid and N-palmitoyl sarcosine, or a mixture of their topically acceptable salts.
De telles formulations sont connues de l'homme du métier; leur préparation sont décrites, par exemple, dans les demandes de brevet publiées sous les numéros,Such formulations are known to those skilled in the art; their preparation is described, for example, in patent applications published under the numbers,
WO92/06778, WO93/28204, WO95/13863, WO95/35089, ou WO96/22109. Dans une variante préférée de la présente invention, la formulation est sous forme d'une émulsion huile dans eau ayant l'aspect d'un lait ayant une viscosité inférieure à lPa.s. comprenant comme émulsionnant une composition auto-émulsionnable à base d'alcools gras.WO92 / 06778, WO93 / 28204, WO95 / 13863, WO95 / 35089, or WO96 / 22109. In a preferred variant of the present invention, the formulation is in the form of an oil-in-water emulsion having the appearance of a milk having a viscosity of less than 1 Pa.s. comprising as emulsifier a self-emulsifiable composition based on fatty alcohols.
Comme composition auto-émulsionnable préférée, on peut citer le MONTANOV® 68 commercialisé par la société SEPPIC. L'invention a particulièrement pour objet l'utilisation telle que définie précédemment pour laquelle la formulation cosmétique comprend à titre de principe actif antagoniste de la substance P, de 0,001% à 6 % en poids d'au moins un composé de formule (I) et si désiré jusqu'à 5 % de gluconate de zinc et/ou jusqu'à 5 % d'aspartate mixte de potassium et de magnésium.. L'invention a tout particulièrement pour objet l'utilisation telle que définie précédemment pour laquelle la formulation cosmétique comprend à titre de principe actif antagoniste de la substance P, de 0,5 % à 2 % en poids d'un composé de formule (I) et si désiré de 0.025% à 0.2% de gluconate de zinc, et l'utilisation telle que définie précédemment pour laquelle la formulation cosmétique comprend à titre de principe actif antagoniste de la substance P de 0,001 % à 0,005 % en poids d'au moins un composé de; formule (I) et si désiré de 0,0001 % à 0.0005% de gluconate de zinc.As self-emulsifying preferred composition include MONTANOV 68 ® marketed by Seppic. The invention particularly relates to the use as defined above for which the cosmetic formulation comprises, as active principle antagonist of substance P, from 0.001% to 6% by weight of at least one compound of formula (I) and if desired up to 5% zinc gluconate and / or up to 5% mixed potassium and magnesium aspartate. The invention particularly relates to the use as defined above for which the formulation cosmetic comprises, as active principle antagonist of substance P, from 0.5% to 2% by weight of a compound of formula (I) and if desired from 0.025% to 0.2% of zinc gluconate, and the use as defined above for which the cosmetic formulation comprises, as active principle antagonist of substance P from 0.001% to 0.005% by weight of at least one compound of; formula (I) and if desired from 0.0001% to 0.0005% zinc gluconate.
Dans un dernier aspect de la présente invention celle-ci a pour objet une formulation cosmétique telle que définie précédemment comprenant en outre un produit d'abrasion superficielle de la peau. Par produit d'abrasion superficielle de la peau, on entend notamment les agents exfoliants et les agents provoquant le renouvellement cellulaire de la peau; on peut citer, comme exemples de tels agents, les alpha et béta-hydroxy-acides tels que les acides, lactique, glycolique ou salicylique, les alpha-céto-acides tels que l'acide pyruvique, ainsi que l'acide acétique, l'acide trichloacétique, l'acide l-pyrrolidone-5-carboxylique, l'acide capryloyl salicylique, l'acide alpha-hydroxy décanoïque, l'acide alpha-hydroxy octanoïque, le gluconolactone, le méthoxy gluconamide, l'acide oxalique, l'acide malique, l'acide tartrique, l'acide mandélique, l'acide benzylique, l'acide gluconique, les peroxydes ,les phénols et les rétinoïdes.In a last aspect of the present invention, its subject is a cosmetic formulation as defined above, further comprising a product of surface abrasion of the skin. By surface abrasion product of the skin is meant in particular the exfoliating agents and the agents causing the cell renewal of the skin; as examples of such agents, mention may be made of alpha and beta-hydroxy acids such as lactic, glycolic or salicylic acids, alpha-keto acids such as pyruvic acid, as well as acetic acid, trichloacetic acid, l-pyrrolidone-5-carboxylic acid, capryloyl salicylic acid, alpha-hydroxy decanoic acid, alpha-hydroxy octanoic acid, gluconolactone, methoxy gluconamide, oxalic acid, l , malic acid, tartaric acid, mandelic acid, benzylic acid, gluconic acid, peroxides, phenols and retinoids.
Les exemples suivants illustrent l'invention sans toutefois la limiter. Exemple 1 : Détermination des propriétés antagonistes de la substance P.The following examples illustrate the invention without, however, limiting it. Example 1: Determination of the antagonistic properties of substance P.
L'activité antagoniste de la substance P des composés de formule (I) a été mise en évidence par la mise en oeuvre pour chacun des composés de formule (I) testés, de la méthode expérimentale illustrée par les essais A à C décrits aux pages 82 à 87 de la demande internationale de brevet publiée sous le numéro WO93/04040 et dans M. A CASCIERI et al, MOLECULAR PHARMACOLOGY 42 (1992) pp 458-463, sur les récepteurs NKi issus de tissu recombinant humain (cellules CHO) en utilisant comme ligand marqué [3H] [Sar9, Met (02)11] - substance P (SP) à une concentration de 0,5 nM, et les composés à tester à des concentrations de 0,05 % , 0,1% et 0,5% pendant un temps d'incubation de 60 min à 22°C.The antagonistic activity of substance P of the compounds of formula (I) was demonstrated by the use, for each of the compounds of formula (I) tested, of the experimental method illustrated by tests A to C described on pages 82 to 87 of the international patent application published under the number WO93 / 04040 and in M. A CASCIERI et al, MOLECULAR PHARMACOLOGY 42 (1992) pp 458-463, on the NKi receptors from human recombinant tissue (CHO cells) using as labeled ligand [ 3 H] [Sar 9 , Met (02) 11 ] - substance P (SP) at a concentration of 0.5 nM, and the compounds to be tested at concentrations of 0.05%, 0.1% and 0.5% for an incubation time of 60 min at 22 ° C.
Les résultats sont exprimés en % d'affinité vis-à-vis du récepteur NKX :The results are expressed in% of affinity towards the NK X receptor:
Proteol SAV 50 S Cocoyl amino acid Proteol OAT Cocoyl oat amino acids Proteol LW30 Cocoyl w eat amino acids Proteol VS 22 Cocoyl Soya amino acids ORAMIX L 30 Cocoyl sodium sarcosinate MONTEUSE LCT Lauroyl collagen amino acids Proteol CO Cocoyl collagen amino acids.Proteol SAV 50 S Cocoyl amino acid Proteol OAT Cocoyl oat amino acids Proteol LW30 Cocoyl w eat amino acids Proteol VS 22 Cocoyl Soya amino acids ORAMIX L 30 Cocoyl sodium sarcosinate MONTEUSE LCT Lauroyl collagen amino acids Proteol CO Cocoyl collagen amino acids.
b. Résultats obtenusb. Results obtained
Les résultats montrent que de façon inattendue les amino acides N-lauroylés ou leurs sels topiquement acceptables, et les aminoacides N-palmitoylés ou leurs sels topiquement acceptables, présentent une activité antagoniste de la substance P.The results show that unexpectedly the N-lauroylated amino acids or their topically acceptable salts, and the N-palmitoylated amino acids or their topically acceptable salts, exhibit a substance P antagonist activity.
Exemples de formulation cosmétiques (Exemples 2 à 32.Examples of cosmetic formulation (Examples 2 to 32.
En utilisant comme composition A, une composition comprenant à titre de principe actif, de 15 % à 40 % en poids d'au moins d'un composé de formule (I), on a préparé les formulations cosmétiques suivantes :Using as composition A, a composition comprising, as active principle, from 15% to 40% by weight of at least one compound of formula (I), the following cosmetic formulations were prepared:
Exemple 2: Crème de soinEXAMPLE 2 Care Cream
Cyclométhicone: 10%Cyclomethicone: 10%
Composition A: 3%Composition A: 3%
SEPIGEL® 501: 0,8%SEPIGEL ® 501: 0.8%
MONTANOV®68: 2% alcool stéarylique: 1% alcool stéarique: 0,5% conservateur: 0,65%MONTANOV ® 68: 2% stearyl alcohol: 1% stearic alcohol: 0.5% preservative: 0.65%
Lysine: 0,025% EDTA (sel disodique): 0,05%Lysine: 0.025% EDTA (disodium salt): 0.05%
Gomme de xanthane: 0,2%Xanthan gum: 0.2%
Glycérine: 3% eau: q.s.p. 100%Glycerin: 3% water: q.s.p. 100%
(Le MONTANOV® 68 (cétéaryl glucoside), est une composition auto-émulsionnable telle que décrite dans WO 92/06778, commercialisée par la société SEPPIC) (® Montanov 68 (cetearyl glucoside) is a self-emulsifying composition as described in WO 92/06778, sold by Seppic)
(Le SEPIGEL® 501 est un agent épaississant à base de copolymères d'acrylamide commercialisé par la société SEPPIC)(SEPIGEL ® 501 is a thickening agent based on acrylamide copolymers sold by the company SEPPIC)
Exemple 3: Crème de soinExample 3: Care Cream
Cyclométhicone: 10%Cyclomethicone: 10%
Composition A: 3%Composition A: 3%
SEPIGEL® 501: 0,8%SEPIGEL ® 501: 0.8%
MONTANOV® 68: 2%MONTANOV ® 68: 2%
Perfluoropolymethylisopropylether: 0,5% alcool stéarylique: 1% alcool stéarique: 0,5% conservateur: 0,65%Perfluoropolymethylisopropylether: 0.5% stearyl alcohol: 1% stearic alcohol: 0.5% preservative: 0.65%
Lysine: 0,025%Lysine: 0.025%
EDTA (sel disodique): 0,05%EDTA (disodium salt): 0.05%
PEMULEN®TR: 0,2%PEMULEN ® TR: 0.2%
Glycérine: 3% eau: q.s.p. 100%Glycerin: 3% water: q.s.p. 100%
(Le PEMULEN®TR est un polymère acrylique commercialisé par GOODRICH) Exemple 4: Baume après-rasage FORMULE(PEMULEN ® TR is an acrylic polymer marketed by GOODRICH) EXAMPLE 4 After Shave Balm FORMULA
A Composition A: 3% SEPIGEL® 501: 1,5% eau: q.s.p 100%A Composition A: 3% SEPIGEL ® 501: 1.5% water: qs 100%
B MICROPEARL® M 100: 5,0%B MICROPEARL ® M 100: 5.0%
SEPICIDE® CI: 0,50% Parfum: 0,20% éthanol 95°: 10,0% (Le MICROPEARL® M 100 est une poudre ultra-fine au toucher très doux et à action matifiante commercialisée par la société MATSUMO)SEPICIDE ® CI: 0.50% Perfume: 0.20% ethanol 95 °: 10.0% (MICROPEARL ® M 100 is an ultra-fine powder with a very soft touch and matifying action sold by the company MATSUMO)
(Le SEPICIDE® CI ,imidazolin urée, est un agent conservateur commercialisé par la société SEPPIC)(SEPICIDE ® CI, imidazolin urea, is a preservative marketed by the company SEPPIC)
MODE OPERATOIRE Ajouter B dans A.PROCEDURE Add B to A.
Exemple 5: Emulsion satinée pour le corpsExample 5: Satin Emulsion for the Body
FORMULEFORMULA
A SIMULSOL® 165: 5,0%A SIMULSOL ® 165: 5.0%
LANOL® 1688: 8,50% beurre de Karité: 2% huile de parafine: 6,5%LANOL ® 1688: 8.50% Shea butter: 2% paraffin oil: 6.5%
LANOL® 14M: 3%LANOL ® 14M: 3%
LANOL® S: 0,6%LANOL ® S: 0.6%
B eau: 66,2%B water: 66.2%
C MICROPEARL® M 100: 5% D Composition A: 3%C MICROPEARL ® M 100: 5% D Composition A: 3%
SEPIGEL® 501: 3%SEPIGEL ® 501: 3%
E SEPICIDE® CI: 0,3% SEPICIDE® HB: 0,5%E SEPICIDE ® CI: 0.3% SEPICIDE ® HB: 0.5%
MONTEINE® CA: 1% parfum: 0,20% acétate de vitamine E: 0,20%MONTEINE ® CA: 1% perfume: 0.20% vitamin E acetate: 0.20%
Sodium pyrolidinone carboxylate: 1% (agent hydratant) (Le SIMULSOL® 165 (stéarate de glycérol/stéarate de PEGIOO) est une composition auto- émulsionnable commercialisée par la société SEPPIC)Sodium pyrolidinone carboxylate: 1% (hydrating agent) (SIMULSOL ® 165 (glycerol stearate / PEGIOO stearate) is a self-emulsifying composition sold by the company SEPPIC)
(Le LANOL® 1688 est un ester émollient à effet non gras commercialisé par la société SEPPIC)(LANOL ® 1688 is a non-greasy emollient ester marketed by the company SEPPIC)
(Le LANOL 14M et le LANOL® S sont des facteurs de consistance commercialisés par la société SEPPIC)(LANOL 14M and LANOL ® S are consistency factors sold by the company SEPPIC)
(Le SEPICIDE® HB , (mélange de phénoxyéthanol/ méthyl paraben/éthylparaben/ propylparaben/butylparaben), est un agent conservateur commercialisé par la société SEPPIC)(SEPICIDE ® HB, (mixture of phenoxyethanol / methyl paraben / ethylparaben / propylparaben / butylparaben), is a preservative sold by the company SEPPIC)
(Le MONTEINE® CA est un agent hydratant commercialisé par la société SEPPIC)(MONTEINE ® CA is a moisturizing agent marketed by the company SEPPIC)
MODE OPERATOIREOPERATING MODE
Ajouter C dans B, émulsionner B dans A à 70°C, puis ajouter D à 60°C puis E à 30°CAdd C in B, emulsify B in A at 70 ° C, then add D at 60 ° C then E at 30 ° C
Exemple 6: Lait corporel FORMULEExample 6: Body milk FORMULA
A SIMULSOL® 165: 5,0%A SIMULSOL ® 165: 5.0%
LANOL® 1688: 12,0%LANOL ® 1688: 12.0%
LANOL® 14M: 2,0% alcool cétylique: 0,3% SCHERCEMOL® OP: 3% B eau: q.s.p. 100%LANOL ® 14M: 2.0% cetyl alcohol: 0.3% SCHERCEMOL ® OP: 3% B water: qs 100%
Composition A: 3% SEPIGEL® 501: 0,35%Composition A: 3% SEPIGEL ® 501: 0.35%
D SEPICIDE® CI: 0,2%D SEPICIDE ® CI: 0.2%
SEPICIDE® HB: 0,5% parfum: 0,20%SEPICIDE ® HB: 0.5% fragrance: 0.20%
(Le SCHERCEMOL® OP est un ester émollient à effet non gras)(SCHERCEMOL ® OP is a non-greasy emollient ester)
MODE OPERATOIREOPERATING MODE
Emulsionner B dans A vers 75°C ; ajouter C vers 60°C, puis D vers 30°CEmulsify B in A at around 75 ° C; add C around 60 ° C, then D around 30 ° C
Exemple 7: crème H/E FORMULEExample 7: O / W FORMULA cream
A SIMULSOL® 165: 5,0% LANOL® 1688: 20,0% LANOL® P: 1,0% (additif à effet stabilisant)A SIMULSOL ® 165: 5.0% LANOL ® 1688: 20.0% LANOL ® P: 1.0% (additive with stabilizing effect)
B eau: q.s.p. 100%B water: q.s.p. 100%
Composition A: 3% SEPIGEL® 501: 2,5%Composition A: 3% SEPIGEL ® 501: 2.5%
D SEPICIDE® CI: 0,20%D SEPICIDE ® CI: 0.20%
SEPICIDE® HB: 0,30%SEPICIDE ® HB: 0.30%
(Le LANOL® P est un additif à effet stabilisant commercialisé par la société SEPPIC)(LANOL ® P is an additive with stabilizing effect marketed by the company SEPPIC)
MODE OPERATOIRE Introduire B dans A vers 75°C ; ajouter C vers 60°C, puis D vers 45°C Exemple 8: gel solaire non gras FORMULEPROCEDURE Introduce B into A at around 75 ° C; add C around 60 ° C, then D around 45 ° C Example 8: non-greasy sun gel FORMULA
A Composition A: 3% 0 SEPIGEL® 501: 0,8% eau: 30%A Composition A: 3% 0 SEPIGEL ® 501: 0.8% water: 30%
B SEPICIDE® CI: 0,20%B SEPICIDE ® CI: 0.20%
SEPICIDE® HB: 0,30% parfum: 0,10%SEPICIDE ® HB: 0.30% fragrance: 0.10%
C colorant: q.s. eau: 30%C dye: q.s. water: 30%
D MICROPEARL® M 100: 3,00% eau: q.s.p 100%D MICROPEARL ® M 100: 3.00% water: qs 100%
E huile de silicone: 2,0%E silicone oil: 2.0%
PARSOL® MCX: 5,00%PARSOL ® MCX: 5.00%
(Le PARSOL® MCX est de l'octyl paraméthoxycinnamate; il est commercialisé par la société GIVAUDAN)(PARSOL ® MCX is octyl paramethoxycinnamate; it is marketed by the company GIVAUDAN)
MODE OPERATOIRE Introduire B dans A; ajouter C, puis D, puis E.PROCEDURE Introduce B into A; add C, then D, then E.
Exemple 9: Lait solaire FORMULEExample 9: SUN MILK FORMULA
A SEPIPERL®N: 3,0% huile de sésame: 5,0%A SEPIPERL ® N: 3.0% sesame oil: 5.0%
PARSOL® MCX: 5,0%PARSOL ® MCX: 5.0%
Carraghénane λ: 0,10% B eau: q.s.p.100%Λ carrageenan: 0.10% B water: qs100%
C Composition A: 3% SEPIGEL® 501: 0,8%C Composition A: 3% SEPIGEL ® 501: 0.8%
D parfum: q.s. conservateur: q.s.D perfume: q.s. curator: q.s.
(Le SEPIPERL®N est un agent nacrant, commercialisé par la société SEPPIC, à base d'un mélange d'alkyl polyglucosides tels que ceux décrits dans WO 95/13863)(SEPIPERL ® N is a pearling agent, marketed by the company SEPPIC, based on a mixture of alkyl polyglucosides such as those described in WO 95/13863)
MODE OPERATOIREOPERATING MODE
Emulsionner B dans A à 75°C puis ajouter C vers 60°C, puis D vers 30°C et ajuster le pH si nécessaireEmulsify B in A at 75 ° C then add C around 60 ° C, then D around 30 ° C and adjust the pH if necessary
Exemple 10: Gel de massageEXAMPLE 10 Massage Gel
FORMULEFORMULA
A Composition A: 3%A Composition A: 3%
SEPIGEL® 501: 3,5% eau: 20,0%SEPIGEL ® 501: 3.5% water: 20.0%
B colorant: 2 gouttes/100g eau: q.s.B dye: 2 drops / 100g water: q.s.
C alcool: 10% menthol: 0,10%C alcohol: 10% menthol: 0.10%
D huile de silicone: 5,0%D silicone oil: 5.0%
MODE OPERATOIREOPERATING MODE
Ajouter B dans A; puis ajouter au mélange, C puis D Exemple 11: gel soin de massage FORMULEAdd B to A; then add to the mixture, C then D Example 11: FORMULA massage treatment gel
A Composition A: 3%A Composition A: 3%
SEPIGEL® 501: 3,0%SEPIGEL ® 501: 3.0%
eau: 30%water: 30%
B SEPICIDE® CI: 0,20%B SEPICIDE ® CI: 0.20%
SEPICIDE® HB: 0,30% parfum: 0,05%SEPICIDE ® HB: 0.30% fragrance: 0.05%
C colorant: q.s. eau: q.s.p 100%C dye: q.s. water: q.s.p 100%
D MICROPEARL® SQL: 5,00%D MICROPEARL ® SQL: 5.00%
LANOL® 1688: 2% (Le MICROPEARL® SQL est un mélange de microparticules renfermant du squalane qui se libère sous l'action du massage; il est commercialisé par la société MATSUMO)LANOL ® 1688: 2% (MICROPEARL ® SQL is a mixture of microparticles containing squalane which is released under the action of massage; it is marketed by the company MATSUMO)
MODE OPERATOIREOPERATING MODE
Préparer A; additionner B, puis C, puis D.Prepare A; add B, then C, then D.
Exemple 12: Gel coup d'éclat FORMULE A Composition A: 3%Example 12: Brightening Gel FORMULA A Composition A: 3%
SEPIGEL® 501: 4% eau: 30%SEPIGEL ® 501: 4% water: 30%
B ELASTINE HPM: 5,0%B ELASTINE HPM: 5.0%
C MICROPEARL® M 100: 3% eau: 5% D SEPICIDE® CI: 0,2%C MICROPEARL ® M 100: 3% water: 5% D SEPICIDE ® CI: 0.2%
SEPICIDE® HB: 0,3%SEPICIDE ® HB: 0.3%
Parfum: 0,06% Sodium pyrolidinone carboxylate 50%: 1% eau: q.s.p. 100%Perfume: 0.06% Sodium pyrolidinone carboxylate 50%: 1% water: q.s.p. 100%
MODE OPERATOIREOPERATING MODE
Préparer A; additionner B, puis C, puis D.Prepare A; add B, then C, then D.
Exemple 13: Lait corporelExample 13: Body Milk
FORMULEFORMULA
A SEPIPERL®N: 3,0%A SEPIPERL ® N: 3.0%
Triheptonate de glycerol 10,0%Glycerol triheptonate 10.0%
B eau q.s.p.100%B water q.s. 100%
C Composition A: 1,5%C Composition A: 1.5%
SEPIGEL® 501 : 1,0%SEPIGEL ® 501: 1.0%
D parfum: q.s. conservateur: q.s.D perfume: q.s. curator: q.s.
MODE OPERATOIRE Fondre A à environ 75°C . Emulsionner B dans A à 75°C puis ajouter C vers 60°C, puis DPROCEDURE Melt A at around 75 ° C. Emulsify B in A at 75 ° C then add C around 60 ° C, then D
Exemple 14: Emulsion démaquillante à l'huile d'amande douce FORMULE MONTANOV® 68: 5% huile d'amandes douces: 5% eau: q.s.p.100% O 99/04757 18Example 14: Make-up removing emulsion with sweet almond oil FORMULA MONTANOV ® 68: 5% sweet almond oil: 5% water: qsp100% O 99/04757 18
Composition A: 1% SEPIGEL® 501: 0,3% glycérine: 5% conservateur: 0,2% parfum: 03%Composition A: 1% SEPIGEL ® 501: 0.3% glycerin: 5% preservative: 0.2% perfume: 03%
Exemple 15: Crème hydratante pour peaux grasses FORMULEEXAMPLE 15 Hydrating Cream for Oily Skin FORMULA
MONTANOV® 68: 5% cétylstéaryloctanoate: 8% octyl palmitate: 2% eau: q.s.p.100%MONTANOV ® 68: 5% cetylstearyl octanoate: 8% octyl palmitate: 2% water: qsp100%
Composition A: 2%Composition A: 2%
SEPIGEL® 501 : 0,6% MICROPEARL® M100: 3,0%SEPIGEL ® 501: 0.6% MICROPEARL ® M100: 3.0%
Mucopolysaccharides: 5%Mucopolysaccharides: 5%
SEPICIDE® HB: 0,8 parfum: 03%SEPICIDE ® HB: 0.8 fragrance: 03%
Exemple 16: Baume après-rasage apaisant sans alcool FORMULEEXAMPLE 16 Soothing Alcohol-Free Aftershave Balm FORMULA
LANOL® 99: 2% huile d'amandes douces: 0,5% eau: q.s.p 100% Composition A: 3%LANOL ® 99: 2% sweet almond oil: 0.5% water: qs 100% Composition A: 3%
SEPIGEL® 501: 3%SEPIGEL ® 501: 3%
SEPICIDE® HB: 0,3%SEPICIDE ® HB: 0.3%
SEPICIDE® CI: 0,2% parfum: 0,4% (Le LANOL® 99 est de l'isononyl isononanoate commercialisé par la société SEPPIC). Exemple 17: Crème aux AHA pour peaux sensibles FORMULESEPICIDE ® CI: 0.2% perfume: 0.4% (LANOL ® 99 is isononyl isononanoate sold by the company SEPPIC). EXAMPLE 17 AHA Cream for Sensitive Skin FORMULA
LANOL® 99: 2%LANOL ® 99: 2%
MONTANOV® 68: 5,0% eau: q.s.p.100%MONTANOV ® 68: 5.0% water: qs100%
Composition A: 0,1 à 5%Composition A: 0.1 to 5%
SEPIGEL® 501: 1,5% acide gluconique: 1,50% triéthylamine: 0,9% SEPICIDE® HB: 0,3%SEPIGEL ® 501: 1.5% gluconic acid: 1.50% triethylamine: 0.9% SEPICIDE ® HB: 0.3%
SEPICIDE® CI: 0,2% parfum: 0,4%SEPICIDE ® CI: 0.2% fragrance: 0.4%
Exemple 18: Soin apaisant après-soleil FORMULEExample 18: Soothing after-sun care FORMULA
LANOL® 99: 10,0% eau: q.s.p.100%LANOL ® 99: 10.0% water: qs100%
Composition A: 3%Composition A: 3%
SEPIGEL® 501: 2,5% SEPICIDE® HB: 0,3%SEPIGEL ® 501: 2.5% SEPICIDE ® HB: 0.3%
SEPICIDE® CI: 0,2% parfum: 0,4% colorant: 0,03%SEPICIDE ® CI: 0.2% fragrance: 0.4% dye: 0.03%
Exemple 19: Lait démaquillant FORMULEExample 19: Cleansing milk FORMULA
SEPIPERL®N 3% PRIMOL 352: 8,0% huile d'amandes douces: 2% eau: q.s.p.100%SEPIPERL ® N 3% PRIMOL 352: 8.0% sweet almond oil: 2% water: qsp100%
Composition A: 2% SEPIGEL® 501: 0,8% conservateur: 0,2%Composition A: 2% SEPIGEL ® 501: 0.8% preservative: 0.2%
Exemple 20: Lait corporel FORMULEExample 20: Body milk FORMULA
SEPIPERL®N: 3,5% 0SEPIPERL ® N: 3.5% 0
LANOL® 37T: 8,0%LANOL ® 37T: 8.0%
SOLAGUM®L: 0,05% eau: q.s.p.100% benzophénone: 2,0% diméthicone 350cPs: 0,05%SOLAGUM ® L: 0.05% water: qs 100% benzophenone: 2.0% dimethicone 350cPs: 0.05%
Composition A: 2%Composition A: 2%
SEPIGEL® 501: 0,8% conservateur: 0,2% parfum: 0,4%SEPIGEL ® 501: 0.8% preservative: 0.2% fragrance: 0.4%
(Le LANOL® 37T est du triheptanoate de glycérol, commercialisé par la société SEPPIC). (Le SOLAGUM®L, est un carraghénane commercialisé par la société SEPPIC).(LANOL ® 37T is glyceroltriheptanoate, marketed by Seppic). (SOLAGUM ® L, is a carrageenan sold by the company SEPPIC).
Exemple 21: émulsion fluide à pH alcalinExample 21 Fluid Emulsion at Alkaline pH
MARCOL® 82: 5,0%MARCOL ® 82: 5.0%
NaOH: 10,0% eau: q.s.p.100%NaOH: 10.0% water: q.s.p. 100%
Composition A: 4%Composition A: 4%
SEPIGEL® 501: 1,5% (Le MARCOL® 82 est une huile paraffine commercialisée par la société ESSO)SEPIGEL ® 501: 1.5% (MARCOL ® 82 is a paraffin oil sold by the company ESSO)
Exemple 22: Fond de teint fluide FORMULEExample 22: FORMULA Fluid Foundation
SIMULSOL® 165 5,0% LANOL® 84D: 8,0%SIMULSOL ® 165 5.0% LANOL ® 84D: 8.0%
LANOL® 99: 5,0% _ l eau: q.s.p.100% pigments et charges minérales: 10,0%LANOL ® 99: 5.0% _ water: qs 100% pigments and mineral fillers: 10.0%
Composition A: 3%Composition A: 3%
SEPIGEL® 501: 1,2% conservateur: 0,2% parfum: 0,4% (Le LANOL® 84D est du dioctylmalate commercialisé par la société SEPPIC).SEPIGEL ® 501: 1.2% preservative: 0.2% perfume: 0.4% (LANOL ® 84D is dioctylmalate sold by the company SEPPIC).
Exemple 23: Lait solaire FORMULEExample 23: SUN MILK FORMULA
SEPIPERL®N 3,5%SEPIPERL ® N 3.5%
LANOL® 37T: 10,0%LANOL ® 37T: 10.0%
PARSOL NOX®: 5,0%PARSOL NOX ® : 5.0%
EUSOLEX® 4360: 2,0% eau: q.s.p.100%EUSOLEX ® 4360: 2.0% water: qsp100%
Composition A: 3%Composition A: 3%
SEPIGEL® 501: 1,8% conservateur: 0,2% parfum: 0,4% (Le PARSOL NOX® et l' EUSOLEX® 4360 sont deux filtres solaires commerciaUsés respectivement par les sociétés GIVAUDAN et MERCK).SEPIGEL ® 501: 1.8% preservative: 0.2% perfume: 0.4% (The PARSOL NOX ® and the EUSOLEX ® 4360 are two sun filters marketed respectively by the companies GIVAUDAN and MERCK).
Exemple 24: Gel contour des yeux FORMULE Composition A: 1%EXAMPLE 24 Eye Contour Gel FORMULA Composition A: 1%
SEPIGEL® 501: 2%SEPIGEL ® 501: 2%
Parfum: 0,06%Perfume: 0.06%
Sodium pyrrolidinonecarboxylate: 0,2%Sodium pyrrolidinonecarboxylate: 0.2%
DOW CORNING® 245 FLuid 2,0% eau: q.s.p. 100% (Le DOW CORNING® 245 FLuid est de la cyclométhicone, commercialisée par la société DOW CORNING):DOW CORNING ® 245 FLuid 2.0% water: qs 100% (DOW CORNING ® 245 FLuid is cyclomethicone, sold by the company DOW CORNING):
Exemple 25: composition de soin non rincée FORMULEExample 25: leave-in care composition FORMULA
Composition A: 3%Composition A: 3%
SEPIGEL® 501: 1,5%SEPIGEL ® 501: 1.5%
Parfum: q.s conservateur: q.s. DOW CORNING® X2 8360: 5,0%Perfume: qs preservative: qs DOW CORNING ® X2 8360: 5.0%
DOW CORNING® Q2 1401 : 15,% eau: q.s.p. 100%DOW CORNING ® Q2 1401: 15,% water: qs 100%
(Le DOW CORNING® 245 FLuid est de la cyclométhicone, commercialisée par la société DOW CORNING):(DOW CORNING ® 245 FLuid is cyclomethicone, sold by the company DOW CORNING):
Exemple 26: gel amincissantEXAMPLE 26 Slimming Gel
Composition A: 5%Composition A: 5%
SEPIGEL® 501: 5% Ethanol 30 %SEPIGEL ® 501: 5% Ethanol 30%
Menthol 0,1 %Menthol 0.1%
Caféine 2,5 % extrait de ruscus 2 % extrait de lierre 2 % SEPICIDE®HP 1 % eau q.s.p. 100 %Caffeine 2.5% ruscus extract 2% ivy extract 2% SEPICIDE ® HP 1% water qs 100%
Exemple 27: Crème confort pour peaux sensiblesEXAMPLE 27 Comfort Cream for Sensitive Skin
Composition A: 3% SEPIGEL® 305: 2%Composition A: 3% SEPIGEL ® 305: 2%
LIP ACIDE® C8G 0,5% MONTANOV® 202 0,3%LIP ACIDE ® C8G 0.5% MONTANOV ® 202 0.3%
Phytosqualan 5%Phytosqualan 5%
Cyclométhicone/polymethyl cyclosiloxane 10%Cyclomethicone / polymethyl cyclosiloxane 10%
SEPICIDE®HB 0,2% eau q.s.p. 100 %SEPICIDE ® HB 0.2% water qs 100%
(Le MONTANOV® 202 (arachidyl glucoside/alcool behenylique) est une composition auto- émulsionnable telle que décrite dans WO 92/06778, commercialisée par la société SEPPIC) (Le LIPACIDE®C8G (octanoyl glycine) est commercialisé par la société SEPPIC)(Montanov ® 202 (arachidyl glucoside / behenyl alcohol) is a self-emulsifiable composition as described in WO 92/06778, sold by Seppic) (Lipacide C8G ® (octanoyl glycine) is commercially available from Seppic)
Exemple 28: Soin apaisantExample 28: Soothing treatment
Composition A: 3%Composition A: 3%
SEPIGEL® 305: 0,7%SEPIGEL ® 305: 0.7%
SIMULSOL® 165 5% capric caprylic triglycéride 5%SIMULSOL ® 165 5% capric caprylic triglyceride 5%
SEPICIDE®HB 0,3%SEPICIDE ® HB 0.3%
SEPICIDE® CI 0,2% eau q.s.p. 100 %oSEPICIDE ® CI 0.2% water qs 100% o
Exemple 29: Gel crème pour peaux sensiblesEXAMPLE 29 Cream Gel for Sensitive Skin
Composition A: 3%Composition A: 3%
SEPIGEL® 600: 2% isohexadécane 5% huile de bourrache 1%SEPIGEL ® 600: 2% isohexadecane 5% borage oil 1%
SEPICIDE®HB 0,3%SEPICIDE ® HB 0.3%
SEPICIDE® CI 0,2% parfum 0,1% eau q.s.p. 100 %SEPICIDE ® CI 0.2% perfume 0.1% water qs 100%
(Le SEPIGEL® 600 est un agent épaississant à base de copolymères d'acrylamide commercialisé par la société SEPPIC) Exemple 30: soin apaisant après soleil(SEPIGEL ® 600 is a thickening agent based on acrylamide copolymers sold by the company SEPPIC) Example 30: Soothing After Sun Care
Composition A: 3%Composition A: 3%
SEPIGEL® 501: 4% cyclométhicone et diméthiconol: 5%SEPIGEL ® 501: 4% cyclomethicone and dimethiconol: 5%
LANOL® 189: 5%LANOL ® 189: 5%
SEPICIDE®HB 0,3%SEPICIDE ® HB 0.3%
SEPICIDE® CI 0,2% parfum 0,1% eau q.s.p. 100 %SEPICIDE ® CI 0.2% perfume 0.1% water qs 100%
(Le LANOL® 189 est un ester de toucher riche et soyeux, commercialisé par la société SEPPIC).(LANOL ® 189 is a rich and silky touch ester, marketed by the company SEPPIC).
Exemple 31: Gel apaisant pour les mainsExample 31: Soothing Hand Gel
Composition A: 3%Composition A: 3%
SEPIGEL® 305: 4%SEPIGEL ® 305: 4%
Isostéaryl isostéarate: 5%Isostearyl isostearate: 5%
MICROPEARL® M305: 1% glycérine: 10%MICROPEARL ® M305: 1% glycerin: 10%
SEPICIDE®HB 0,3%SEPICIDE ® HB 0.3%
SEPICIDE® CI 0,2% parfum 0,2% eau q.s.p. 100 %SEPICIDE ® CI 0.2% perfume 0.2% water qs 100%
(Le MECROPEARL®M305 est un copolymère réticulé de polyméthyl méthacrylate est commercialisé par la société MATSUMO).(MECROPEARL ® M305 is a crosslinked copolymer of polymethyl methacrylate is sold by the company MATSUMO).
Exemple 32: Crème hydratante pour peaux sensiblesEXAMPLE 32 Moisturizing Cream for Sensitive Skin
MONTANOV® 68: 7%MONTANOV ® 68: 7%
Isostéaryl isostéarate: 5% Diméthicone: 10% eau: q.s.p.100% Composition A: 2% SEPIGEL® 305: 1% SEPICIDE® HB: 0,3% SEPICIDE® CI: 0,2% parfum: 0,2%Isostearyl isostearate: 5% Dimethicone: 10% water: qsp100% Composition A: 2% SEPIGEL ® 305: 1% SEPICIDE ® HB: 0.3% SEPICIDE ® CI: 0.2% perfume: 0.2%
Exemple 33: soin auto-bronzant Composition A : 3% DHA 1% SEPIGEL® 305: 2%Example 33: self-tanning care composition A: 3% DHA 1% Sepigel ® 305: 2%
MONTANOV® 202 3% Huile d'amande douce 7% Diméthicone: 3% Parfum 0,1% SEPIFILM®HB 0,3%MONTANOV ® 202 3% oil of sweet almond 7% Dimethicone 3% Perfume 0.1% SEPIFILM HB ® 0.3%
SEPΠ LM®CI 0,2% eau: q.s.p.100% SEPΠ LM ® CI 0.2% water: qsp100%

Claims

REVENDICATIONS
1. Utilisation d'au moins un antagoniste de la substance P dans une formulation cosmétique pour apaiser et/ou protéger tout type de peaux et notamment les peaux sensibles, caractérisée en ce que l'antagoniste de la substance P est un composé de formule (I) :1. Use of at least one substance P antagonist in a cosmetic formulation to soothe and / or protect any type of skin and in particular sensitive skin, characterized in that the substance P antagonist is a compound of formula ( I):
(I) Rι ou ses sels topiquement acceptables, ou un mélange de ces composés ou sels, dans laquelle R représente la chaîne caractérisante d'un acide gras, saturé ou insaturé, linéaire ou ramifié, comportant de 3 à 30 atomes de carbone, i représente une chaîne caractérisante d'un acide aminé et m est compris entre 1 et 5, et R2 représente un atome d'hydrogène ou un radical alkyle comportant de 1 à 3 atomes de carbone. (I) Rι or its topically acceptable salts, or a mixture of these compounds or salts, in which R represents the characterizing chain of a fatty acid, saturated or unsaturated, linear or branched, comprising from 3 to 30 carbon atoms, i represents a chain characterizing an amino acid and m is between 1 and 5, and R 2 represents a hydrogen atom or an alkyl radical containing from 1 to 3 carbon atoms.
2. Utilisation telle définie à la revendication 1, pour laquelle, dans la formule (I), le fragment R — CO comporte de 7 à 22 atomes de carbone et représente notamment l'un des radicaux hexanoyle, heptanoyle, octanoyle (capryloyle), décanoyle (caproyle), undécylènoyle, dodécanoyle (lauroyle), tétradécanoyle (myristyle), hexadécanoyle (palmitoyle), octadécanoyle (stéaroyle), eicosanoyle (arachidoyle), docosanoyle (behènoyle), octodécènoyle (oléyle), éicosènoyle (gadoloyle), docosènoyle (érucyle), octadécadiènoyle (linolènoyle).2. Use as defined in claim 1, for which, in formula (I), the R - CO fragment contains from 7 to 22 carbon atoms and represents in particular one of the hexanoyl, heptanoyl, octanoyl (capryloyl) radicals, decanoyl (caproyl), undecylenoyl, dodecanoyl (lauroyl), tetradecanoyl (myristyle), octadecanoyl (palmitoyl), eicosanoyle (arachidoyle), docosanoyle (behènoyle), octodecoyl (octosol) ), octadecadienoyl (linolenic).
3. Utilisation telle que définie à l'une quelconque des revendications 1 ou 2, pour laquelle, dans la formule (I), le fragment R-CO comporte de 10 à 18 atomes de carbone.3. Use as defined in any one of claims 1 or 2, for which, in formula (I), the R-CO fragment contains from 10 to 18 carbon atoms.
4. Utilisation telle que définie à la revendication 3 pour laquelle, dans la formule (I), le fragment R-CO- représente le radical lauroyle ou le radical palmitoyle.4. Use as defined in claim 3 for which, in formula (I), the R-CO- fragment represents the lauroyl radical or the palmitoyl radical.
5. Utilisation telle que définie à l'une des revendications 1 à 4, pour laquelle le ou les composés de formule (I) sont choisis parmi le lauroyl alanine, le lauroyl lysine, l'acide lauroyl aspartique, l'acide lauroyl glutamique, l'acide palmitoyl glutamique, l'acide stéaroyle glutamique, la palmitoyl proline ou la palmitoyl sarcosine, ou leurs sels topiquement acceptables. 5. Use as defined in one of claims 1 to 4, for which the compound or compounds of formula (I) are chosen from lauroyl alanine, lauroyl lysine, lauroyl aspartic acid, lauroyl glutamic acid, palmitoyl glutamic acid, stearoyl glutamic acid, palmitoyl proline or palmitoyl sarcosine, or their topically acceptable salts.
6. Utilisation telle que définie à l'une des revendications 1 à 5 pour laquelle la formule cosmétique comprend comme principe actif soit le mélange N-palmitoyl proline et acide N-palmitoyl glutamique ou un mélange de leurs sels topiquement acceptables, soit le mélange N-palmitoyl proline, acide N-palmitoyl glutamique et N-palmitoyl sarcosine ou un mélange de leurs sels topiquement acceptables.6. Use as defined in one of claims 1 to 5 for which the cosmetic formula comprises as active principle either the mixture N-palmitoyl proline and N-palmitoyl glutamic acid or a mixture of their topically acceptable salts, or the mixture N -palmitoyl proline, N-palmitoyl glutamic acid and N-palmitoyl sarcosine or a mixture of their topically acceptable salts.
7. Utilisation telle que définie à l'une des revendications 1 à 6, pour laquelle la formulation cosmétique comprend en outre du gluconate de zinc et/ou de l'aspartate mixte de magnésium et de potassium. 7. Use as defined in one of claims 1 to 6, for which the cosmetic formulation also comprises zinc gluconate and / or mixed magnesium and potassium aspartate.
8. Utilisation telle que définie à l'une des revendications 1 à 7 pour laquelle la formulation cosmétique est sous forme d'une émulsion huile dans eau ayant l'aspect d'un lait ayant une viscosité inférieure à lPa.s. comprend comme émulsionnant une composition auto-émulsionnable à base d'alcools gras.8. Use as defined in one of claims 1 to 7 for which the cosmetic formulation is in the form of an oil-in-water emulsion having the appearance of a milk having a viscosity of less than lPa.s. comprises as an emulsifier a self-emulsifiable composition based on fatty alcohols.
9. Utilisation telle que définie à l'une des revendications 1 à 8 pour laquelle la formulation cosmétique comprend à titre de principe actif antagoniste de la substance P, de9. Use as defined in one of claims 1 to 8 for which the cosmetic formulation comprises, as active principle antagonist of substance P, of
0,001 à 6 % en poids d'au moins un composé de formule (I).0.001 to 6% by weight of at least one compound of formula (I).
10. Utilisation telle que définie à l'une des revendications 1 à 9, pour laquelle la formulation cosmétique comprend à titre de principe actif antagoniste de la substance P, de 0,5 % à 2 % en poids d'un composé de formule (I) 11. Actif cosmétique comprenant à titre de principe actif de 15 % à 60 % et, plus particulièrement 20 % à 40 % en poids, d'un mélange de composés de formule (II) telle que définie précédemment, choisi parmi les mélanges suivants :10. Use as defined in one of claims 1 to 9, for which the cosmetic formulation comprises, as active principle antagonist of substance P, from 0.5% to 2% by weight of a compound of formula ( I) 11. Cosmetic active agent comprising, as active principle from 15% to 60% and, more particularly 20% to 40% by weight, of a mixture of compounds of formula (II) as defined above, chosen from mixtures following:
-N-palmitoyl proline et acide N-palmitoyl glutamique ou un mélange de leurs sels topiquement acceptables, -N-palmitoyl proline, acide N-palmitoyl glutamique et N-palmitoyl sarcosine ou un mélange de leurs sels topiquement acceptables. -N-palmitoyl proline and N-palmitoyl glutamic acid or a mixture of their topically acceptable salts, -N-palmitoyl proline, N-palmitoyl glutamic acid and N-palmitoyl sarcosine or a mixture of their topically acceptable salts.
EP98940310A 1997-07-24 1998-07-22 Use of a lipoaminoacid in a cosmetic formulation Withdrawn EP1003471A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9709424 1997-07-24
FR9709424A FR2766366B1 (en) 1997-07-24 1997-07-24 USE OF AT LEAST ONE LIPOAMINOACID AS AN ANTAGONIST OF THE SUBSTANCE P IN A COSMETIC FORMULATION FOR SOOTHING AND / OR PROTECTING ALL SKIN TYPES AND, IN PARTICULAR, SENSITIVE SKIN
PCT/FR1998/001617 WO1999004757A1 (en) 1997-07-24 1998-07-22 Use of a lipoaminoacid in a cosmetic formulation

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EP1003471A1 true EP1003471A1 (en) 2000-05-31

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FR2787323B1 (en) * 1998-12-22 2003-02-14 Seppic Sa USE OF N-ACYLATED AMINO ACID COMPOUNDS AS TEXTURING AGENT
FR2835252B1 (en) * 2002-01-25 2005-08-05 Seppic Sa USE OF A PROTEIN KINASE A INACTIFYING COMPOUND IN A COMPOSITION CONTAINING A COSMETICALLY ACCEPTABLE MEDIUM FOR LAMINATING THE SKIN
FR2923383B1 (en) * 2007-11-08 2010-03-19 Oreal USE OF AN N-ACYLATED SARCOSINATE AS A MICROBIAL ANTI-ADHESION AGENT.
JP5527414B2 (en) 2010-07-01 2014-06-18 トヨタ自動車株式会社 Manufacturing method of ceramic laminate
US9251188B2 (en) 2010-11-05 2016-02-02 Nec Corporation Information processing device
WO2012077241A1 (en) 2010-12-06 2012-06-14 L'oreal Powdery cosmetic composition
US8956633B2 (en) 2011-05-13 2015-02-17 L'oreal Powdery cosmetic composition
US9511144B2 (en) 2013-03-14 2016-12-06 The Proctor & Gamble Company Cosmetic compositions and methods providing enhanced penetration of skin care actives
JP6532646B2 (en) 2013-12-06 2019-06-19 ロレアル Powdery cosmetic composition
CN113862176A (en) * 2021-09-04 2021-12-31 赣州澳丽尔化妆品有限公司 Preparation method of aureobasidium pullulans

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JP2001510784A (en) 2001-08-07
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WO1999004757A1 (en) 1999-02-04

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