FR2702766A1 - New synthetic compounds, process for preparing them and use in cosmetic and dermopharmaceutical preparations for improving suntanning (bronzing) - Google Patents

New synthetic compounds, process for preparing them and use in cosmetic and dermopharmaceutical preparations for improving suntanning (bronzing) Download PDF

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FR2702766A1
FR2702766A1 FR9303055A FR9303055A FR2702766A1 FR 2702766 A1 FR2702766 A1 FR 2702766A1 FR 9303055 A FR9303055 A FR 9303055A FR 9303055 A FR9303055 A FR 9303055A FR 2702766 A1 FR2702766 A1 FR 2702766A1
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tyrosine
ester
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acid
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FR2702766B1 (en
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Greff Daniel
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Sederma SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/49—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin

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  • Animal Behavior & Ethology (AREA)
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  • Dermatology (AREA)
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Abstract

The patent describes the synthesis and use of new tyrosine derivatives as precursors of natural melanin, stimulators of suntanning and anti-free-radical agents having, in particular, the advantage of being water-resistant. They are in particular N-oleoyl-L-tyrosine and its homologues. The products are intended for cosmetics and dermopharmaceuticals.

Description

L'utilisation cosmétique et dermopharmaceutique de l'acide aminé tyrosine et de certains dérivés pour accélérer le bronzage naturel est connue. La tyrosine libre n'est pourtant pas très soluble aux concentrations nécessaires et efficaces, son emploi est donc limité. La solution à ce problème, apportée à ce jour, est la dérivatisation de la tyrosine soit par voie chimique soit par voie enzymatique pour faire des produits plus hydrosolubles et donc plus compatibles avec les crèmes et autres produits destinés à la protection solaire: L-malyl-L-tyrosine (brevet français n" 2621916), N-acétyl-tyrosine (UK patent application GB 2198042), gluconate de tyrosine et autres.The cosmetic and dermopharmaceutical use of the amino acid tyrosine and certain derivatives for accelerating natural tanning is known. Free tyrosine is however not very soluble at the necessary and effective concentrations, its use is therefore limited. The solution to this problem, brought to date, is the derivatization of tyrosine either chemically or enzymatically to make more water-soluble products and therefore more compatible with creams and other products intended for sun protection: L-malyl -L-tyrosine (French patent no. 2621916), N-acetyl-tyrosine (UK patent application GB 2198042), tyrosine gluconate and others.

Ces produits ont des inconvénients technologiques (brunissement dans le temps, odeur, prix) que l'objet de la présente invention se propose de combler.These products have technological drawbacks (browning over time, odor, price) which the object of the present invention proposes to overcome.

II a été découvert, que certains dérivés de la tyrosine, la N-oléoyl-L -tyrosine en particulier, présentent des avantages considérables par rapport aux autres produits dérivés de la tyrosine: la N-oléoyl-Ltyrosine n'est pas soluble dans l'eau, mais soluble dans des lipides, ce qui fait qu'elle peut être facilement incorporée dans des émulsions (crèmes, laits, pommades) à différentes doses. Le faible coût de sa synthèse permet son utilisation à des concentrations très efficaces. It has been discovered that certain derivatives of tyrosine, N-oleoyl-L-tyrosine in particular, present considerable advantages compared to the other products derived from tyrosine: N-oleoyl-Ltyrosine is not soluble in l water, but soluble in lipids, which means that it can be easily incorporated into emulsions (creams, milks, ointments) in different doses. The low cost of its synthesis allows its use at very effective concentrations.

Elle se présente sous forme huileuse ou pâteuse, ce qui permet d'éviter toute étape de prédissolution lors de l'emploi. It comes in oily or pasty form, which avoids any predissolution step during use.

La chaîne monoinsaturée est stable dans le temps et confère à la molécule une activité antiradicalaire supplémentaire, ce qui complète son action de protection solaire.The monounsaturated chain is stable over time and gives the molecule additional anti-free radical activity, which completes its sun protection action.

Nous allons décrire ces points plus en détail.We will describe these points in more detail.

LA SYNTHESE
La synthèse des dérivés N-acylés de la L-Tyrosine peut être réalisée par les voies classiques de la formation d'une liaison amide entre un acide et une amine, à savoir par un chlorure d'acide, par un azoture, par un anhydride, par un ester de paranitrophénol, par un ester de succinimide, par un ester de dicyclohexylcarbodiimide, par un ester de pentafluorophenol, par un ester d'alkyle inférieur, en milieu an hydre ou partiellement aqueux ou, dans des solvants tels que le tétrahydrofuranne, la pyridine, le diméthylformamide et le dichlorométhane.SYNTHESIS
The synthesis of N-acylated derivatives of L-Tyrosine can be carried out by the conventional routes of the formation of an amide bond between an acid and an amine, namely by an acid chloride, by an azide, by an anhydride , with a paranitrophenol ester, with a succinimide ester, with a dicyclohexylcarbodiimide ester, with a pentafluorophenol ester, with a lower alkyl ester, in an aqueous or partially aqueous medium or, in solvents such as tetrahydrofuran, pyridine, dimethylformamide and dichloromethane.

A titre d'exemple, nous décrivons la synthèse suivante:
On mélange sous agitation 38 g d'acide oléique, 170 g de tetrahydrofurane et 14.5 g de triéthylamine. On refroidit à -5 C et on ajoute, toujours en dessous de 0 C, 14.8 g de chloroformate d'éthyle pour former l'anhydride mixte de formule RCOOCOOC2H5 où R est le radical de l'acide oléique. On agite 30 minutes à 0 C, puis on ajoute entre 0 et 5"C une suspension de 5.4 g de soude et de 23,56 g de tyrosine, dissous dans 125 g d'eau.As an example, we describe the following synthesis:
38 g of oleic acid, 170 g of tetrahydrofuran and 14.5 g of triethylamine are mixed with stirring. Cool to -5 ° C. and add, still below 0 ° C., 14.8 g of ethyl chloroformate to form the mixed anhydride of formula RCOOCOOC2H5 where R is the radical of oleic acid. The mixture is stirred for 30 minutes at 0 ° C., then a suspension of 5.4 g of sodium hydroxide and 23.56 g of tyrosine, dissolved in 125 g of water, is added between 0 and 5 ° C.

On agite pendant une heure à 0 C, puis 15 heures à 20"C. On ajoute de l'acide chlorhydrique jusqu'à pH 2-3 et on filtre l'insoluble sur Clarcel. On décante la phase aqueuse inférieure et on lave le THF par 3 fois 50 g d'eau salée. The mixture is stirred for one hour at 0 ° C., then 15 hours at 20 ° C. Hydrochloric acid is added to pH 2-3 and the insoluble material is filtered through Clarcel. The lower aqueous phase is decanted and the mixture is washed. THF per 3 times 50 g of salt water.

On sèche sur 15 g de sulfate de magnésium, puis on concentre sous vide à 50"C; on obtient ainsi 57 g d'une huile jaune de "N-oléoyl-Ltyrosine" contenant 25-30% d'acide oléique libre (tous les pourcentages indiqués par la suite sont des pourcentages massiques).Dried over 15 g of magnesium sulfate, then concentrated in vacuo at 50 "C; thus obtaining 57 g of a yellow oil of" N-oleoyl-Ltyrosine "containing 25-30% of free oleic acid (all the percentages indicated below are mass percentages).

Une purification par chromatographie liquide permettrait d'éliminer l'acide oléique en excès mais, pour l'utilisation prévue ceci n'est pas nécessaire.Purification by liquid chromatography would remove excess oleic acid, but for the intended use this is not necessary.

On peut donc employer dans les produits cosmétiques ou dermopharmaceutiques, des dérivés N-acyl-tyrosine décrits sous forme pure ou sous forme de mélange avec l'acide gras libre correspondant en excès. Cette dernière forme a l'avantage supplémentaire, en ce qui concerne l'acide oléique, de profiter de l'activité connue de cet acide5 à savoir la capacité de faire pénétrer un principe actif à travers la couche cornée vers l'épiderme.It is therefore possible to use, in cosmetic or dermopharmaceutical products, N-acyl-tyrosine derivatives described in pure form or in the form of a mixture with the corresponding free fatty acid in excess. This latter form has the additional advantage, as regards oleic acid, of taking advantage of the known activity of this acid5, namely the ability to make an active principle penetrate through the stratum corneum towards the epidermis.

Les proportions de l'acide gras libre associé au dérivé de la tyrosine peuvent varier entre 0.1 et 40%.The proportions of the free fatty acid associated with the tyrosine derivative can vary between 0.1 and 40%.

De la même façon peuvent être synthétisés les dérivés N-palmitoléyl
L-tyrosine, N-eicosénoyl-L-tyrosine et N-linoléoyl-L-tyrosine.In the same way can be synthesized N-palmitoleyl derivatives
L-tyrosine, N-eicosenoyl-L-tyrosine and N-linoleoyl-L-tyrosine.

Ces produits sont pourtant plus chers. L'acide oléique utilisé peut provenir de toute source. II peut être employé sous forme très pure ou bien sous forme dite "technique", contenant au moins 65 % d'acide oléique, ce qui implique qu'il contienne un certain pourcentage d'acides gras insaturés autres qu'oléique (linoléique, linolénique, palmitoléique), mais aussi des acides gras saturés. La proportion d'acides gras saturés ne doit toutefois pas dépasser 20%. These products are however more expensive. The oleic acid used can come from any source. It can be used in very pure form or in so-called "technical" form, containing at least 65% oleic acid, which implies that it contains a certain percentage of unsaturated fatty acids other than oleic (linoleic, linolenic , palmitoleic), but also saturated fatty acids. The proportion of saturated fatty acids must not, however, exceed 20%.

Une remarque identique s'applique aux autres acides gras insaturés éventuellement utilisés.The same remark applies to other unsaturated fatty acids that may be used.

Pour modifier encore la solubilité du produit, il peut être avantageux de préparer un amide ou un ester méthylique ou éthylique de la molécule.To further modify the solubility of the product, it may be advantageous to prepare an amide or a methyl or ethyl ester of the molecule.

La formule générale des produits objets du brevet est donc
R1-CO-Tyr-Y (I) dans laquelle:
R1 désigne un radical hydrocarboné C11 à C19 linéaire et portant une ou plusieurs insaturations éthyléniques, et notamment une ou deux, ou un mélange de radicaux hydrocarbonés en C11-C19, linéaires, saturés ou portant une ou plusieurs insaturations éthyléniques et notamment une ou deux, dans lequel la proportion de radicaux saturés ne peut excéder 20%.The general formula of the products which are the subject of the patent is therefore
R1-CO-Tyr-Y (I) in which:
R1 denotes a linear C11 to C19 hydrocarbon radical bearing one or more ethylenic unsaturations, and in particular one or two, or a mixture of C11-C19 hydrocarbon radicals, linear, saturated or bearing one or more ethylenic unsaturations and in particular one or two, in which the proportion of saturated radicals cannot exceed 20%.

Y désigne OH, O M+, OCH3, OC2H5 ou Nu, avec M+ = Na+, K+ ou NH4+. Y denotes OH, O M +, OCH3, OC2H5 or Nu, with M + = Na +, K + or NH4 +.

Tyr désigne le résidu Tyrosyle tel qu'il est employé dans la description des protéines.Tyr denotes the Tyrosyle residue as used in the description of proteins.

L'activité bronzante:
Des crèmes solaires ont été préparées contenant 0.0% (placebo), 0.5%, 1% et 1.5% de N-oléoyl-L-tyrosine. Quinze personnes volontaires de phototype Il à IV ont appliqué les crèmes, en quantité égales, sur des zones définies de l'avant-bras. Des irradiations UVA, à doses constantes, ont été administrées pendant 2 semaines. La coloration progressive de la peau est mesurée par chromamètrie (MINOLTA).Tanning activity:
Sun creams were prepared containing 0.0% (placebo), 0.5%, 1% and 1.5% of N-oleoyl-L-tyrosine. Fifteen volunteers of phototype II to IV applied the creams, in equal quantities, to defined areas of the forearm. UVA irradiation, at constant doses, was administered for 2 weeks. The progressive coloring of the skin is measured by chromametry (MINOLTA).

On constate un bronzage plus rapide avec les crèmes contenant la
N-oléoyl-L-tyrosine qu'avec le placebo: I'effet dose est significatif. There is a faster tan with creams containing
N-oleoyl-L-tyrosine than with placebo: the dose effect is significant.

En comparaison, d'autres dérivés de la tyrosine à la concentration équivalente ont une activité d'accélération de bronzage inférieure.In comparison, other tyrosine derivatives at the equivalent concentration have a lower tanning acceleration activity.

La résistance à l'eau:
Un test de bronzage supplémentaire avec 3 personnes a été entrepris.Water resistance:
An additional tanning test with 3 people was undertaken.

Après l'application de la crème contenant la N-oléoyl-L-tyrosine (1.5%) suivie d'une période d'attente de 10 minutes, I'endroit d'application a été lavé à l'aide d'une éponge imbibée d'eau. L'irradiation UVA a été effectuée directement après sèchage du bras à l'aide d'une serviette.After applying the cream containing N-oleoyl-L-tyrosine (1.5%) followed by a waiting period of 10 minutes, the place of application was washed using a soaked sponge of water. UVA irradiation was performed directly after drying the arm with a towel.

La N-oléoyl-L-tyrosine a été comparée aux dérivés hydrosolubles de la tyrosine du commerce aux concentrations équivalentes.N-oleoyl-L-tyrosine was compared with water-soluble derivatives of commercial tyrosine at equivalent concentrations.

II en résulte que la N-oléoyl-L-tyrosine reste absorbée dans la peau et peut agir en tant qu'accélérateur de bronzage, alors que les dérivés hydrosolubles ont été en grande partie éliminés par le "lavage"'.  As a result, N-oleoyl-L-tyrosine remains absorbed into the skin and can act as a tanning accelerator, while the water-soluble derivatives have been largely eliminated by "washing".

Test d'activité "antiradicalaire"
Pour ce test, on met des acides gras polyinsaturés (lécithines naturelles) en présence d'un système fortement oxydatif (H2O2 + FeCI2). On rajoute le produit à tester aux concentrations habituelles et on mesure l'apparition des peroxydes lipidiques qui peuvent être dosés par voie chimique ou spectroscopique."Anti-free radical" activity test
For this test, polyunsaturated fatty acids (natural lecithins) are put in the presence of a strongly oxidative system (H2O2 + FeCI2). The product to be tested is added at the usual concentrations and the appearance of lipid peroxides is measured, which can be measured chemically or spectroscopically.

La N-oléoyl-L-tyrosine à 1% et à 2% montre une forte activité antiradicalaire (95% et 98% d'inhibition de la peroxydation).1% and 2% N-oleoyl-L-tyrosine shows strong anti-free radical activity (95% and 98% inhibition of peroxidation).

Les dérivés de la tyrosine objets du brevet peuvent être avantageusement utilisés dans tout produit cosmétique ou dermopharmaceutique, dans les gels, les lotions, les émulsions H/E ou E/H, les laits, les pommades et onguents, pâtes, dans les huiles corporelles, les lotions capillaires, les shampooings les savons, les sticks et les crayons, les sprays.The tyrosine derivatives which are the subject of the patent can be advantageously used in any cosmetic or dermopharmaceutical product, in gels, lotions, O / W or W / O emulsions, milks, ointments and ointments, pastes, in body oils. , hair lotions, shampoos, soaps, sticks and pencils, sprays.

Ils s'emploient non seulement dans les produits pour la préparation au soleil, dans les produits de protection solaire et dans les produits aprèssoleil, mais également dans toute préparation cosmétique de soins, permettant de protéger la peau durant la journée même contre les faibles doses d'irradiation (exposition quotidienne normale): les crèmes de jour, les fonds de teint, les produits de maquillage, les masques, lipsticks.They are used not only in products for sun preparation, in sun protection products and in after-sun products, but also in any cosmetic care preparation, which protects the skin during the day even against low doses of 'irradiation (normal daily exposure): day creams, foundations, make-up products, masks, lipsticks.

Cette liste n'est pas limitative.This list is not exhaustive.

Pour être efficace, il faut employer des doses variant de 0.05 à 10%, de préférence entre 0.1 et 5% du composé de formule (I) selon l'effet désiré.To be effective, it is necessary to use doses varying from 0.05 to 10%, preferably between 0.1 and 5% of the compound of formula (I) depending on the desired effect.

On emploie le composé de formule (I) en présence d'un adjuvant choisi parmi les corps gras, les solvants1 I'eau, les épaississants, les émulsions, les produits hydratants, les adoucissants, les filtres solaires, les germicides, les colorants, les conservateurs, les parfums, les propulseurs et les tensio-actifs.The compound of formula (I) is used in the presence of an adjuvant chosen from fatty substances, water solvents, thickeners, emulsions, moisturizers, softeners, sun filters, germicides, dyes, preservatives, perfumes, propellants and surfactants.

Les composés de formule (I) peuvent être incorporés dans des vecteurs comme les liposomes, les chylomicrons, les macro-, micro- et nanoparticules ainsi que les macro-, micro- et nanocapsules ou, absorbés sur des polymères organiques poudreux, les talcs, bentonites et autres supports minéraux. The compounds of formula (I) can be incorporated into vectors such as liposomes, chylomicrons, macro-, micro- and nanoparticles as well as macro-, micro- and nanocapsules or, absorbed on powdery organic polymers, talcs, bentonites and other mineral supports.

Claims (10)

REVENDICATIONS 1) Nouveaux composés chimiques de formule générale:1) New chemical compounds of general formula: R1-CO-Tyr-Y (I) R1-CO-Tyr-Y (I) dans laquelle: * R1 désigne un radical hydrocarboné C11 à C19 linéaire et portant in which: * R1 denotes a linear C11 to C19 hydrocarbon radical bearing une ou plusieurs insaturations éthyléniques, et notamment une ou one or more ethylenic unsaturations, and in particular one or more deux, ou un mélange de radicaux hydrocarbonés en C11-C19, two, or a mixture of C11-C19 hydrocarbon radicals, linéaires, saturés ou portant une ou plusieurs insaturations linear, saturated or bearing one or more unsaturations éthyléniques et notamment une ou deux, dans lequel la proportion ethylenic and especially one or two, in which the proportion de radicaux saturés ne peut excéder 20%. of saturated radicals cannot exceed 20%. ou NH4+. or NH4 +. * Y désigne OH, O M+, OCH3, OC2H5 ou NH2 avec M+ = Na+, K+* Y denotes OH, O M +, OCH3, OC2H5 or NH2 with M + = Na +, K + description des protéines. description of proteins. * Tyr désigne le résidu Tyrosyle tel qu'il est employé dans la* Tyr indicates the Tyrosyle residue as used in the 2) Composés selon la revendication 1 caractérisés en ce que R1 est2) Compounds according to claim 1 characterized in that R1 is un radical dérivé de l'acide oléique ou linoléique. a radical derived from oleic or linoleic acid. 3) Composés selon l'une quelconque des revendications 1 et 23) Compounds according to any one of claims 1 and 2 caractérisés en ce que Y est OH ou O- M+ avec M+=Na+ ou K+ ou NH:.  characterized in that Y is OH or O- M + with M + = Na + or K + or NH :. 4) Composés selon l'une quelconque des revendications 1 à 34) Compounds according to any one of claims 1 to 3 caractérisés en ce que R1 est le radical de l'acide oléique technique characterized in that R1 is the radical of technical oleic acid contenant au moins 65% d'acide oléique et au plus 20% d'acide containing at least 65% oleic acid and at most 20% acid gras saturé. saturated fat. 5) Composés selon l'une quelconque des revendications 1 à 45) Compounds according to any one of claims 1 to 4 caractérisés en ce qu'ils sont utilisés sous forme de mélange avec characterized in that they are used in the form of a mixture with de l'acide gras libre, où la proportion de l'acide gras libre varie free fatty acid, where the proportion of free fatty acid varies entre 0,1 et 40 %.  between 0.1 and 40%. 6) Procédé de préparation d'un composé de formule (I) selon l'une6) Process for the preparation of a compound of formula (I) according to one quelconque des revendications 1 à 5 caractérisé par le fait qu'il any one of claims 1 to 5 characterized in that it consiste à acyler la fonction amine de la tyrosine ou d'un tyrosine consists in acylating the amine function of tyrosine or of a tyrosine amide par un chlorure d'acide, par un anhydride, par un azoture, amide with an acid chloride, with an anhydride, with an azide, par un ester paranitrophénol, par un ester de succinimide, par un by a paranitrophenol ester, by a succinimide ester, by a ester de dicyclohexylcarbodiimide, par un ester de dicyclohexylcarbodiimide ester, by an ester of pentafluorophénol, par un ester d'alkyle inférieur, en milieu anhydre pentafluorophenol, by a lower alkyl ester, in an anhydrous medium ou partiellement aqueux ou dans des solvants tels que le or partially aqueous or in solvents such as tetrahydrofuranne, la pyridine, le diméthylformamide et le tetrahydrofuran, pyridine, dimethylformamide and dichlorométhane.  dichloromethane. 7) Procédé de préparation d'un composé de formule (I) selon la7) Process for the preparation of a compound of formula (I) according to the revendication 6 caractérisé par le fait que l'anhydride est un claim 6 characterized in that the anhydride is a anhydride mixte de formule R1COOCOOC2H5, R1 étant le radical mixed anhydride of formula R1COOCOOC2H5, R1 being the radical de l'acide oléique. oleic acid. 8) Composition à usage cosmétique ou dermopharmaceutique8) Composition for cosmetic or dermopharmaceutical use caractérisée par le fait qu'elle contient 0.05 à 10% en poids, de characterized in that it contains 0.05 to 10% by weight, of préférence 0.1 à 5% de composé de formule (l) selon l'une preferably 0.1 to 5% of compound of formula (l) according to one quelconque des revendications de 1 à 5 en présence d'un adjuvant any of claims 1 to 5 in the presence of an adjuvant choisi parmi les corps gras, les solvants, I'eau, les épaississants, chosen from fatty substances, solvents, water, thickeners, les émulsions, les produits hydratants, les adoucissants, les filtres emulsions, moisturizers, softeners, filters solaires, les germicides, les colorants, les conservateurs, les sunscreen, germicides, dyes, preservatives, parfums, les propulseurs et les tensio-actifs. perfumes, propellants and surfactants. 9) Composition à usage cosmétique ou dermopharmaceutique, selon9) Composition for cosmetic or dermopharmaceutical use, according to la revendication 8 caractérisée en ce qu'elle est présentée dans claim 8 characterized in that it is presented in toute forme galénique employée en cosmétique ou any dosage form used in cosmetics or dermopharmacie : gels, lotions, émulsions H/E et E/H, laits, dermopharmacy: gels, lotions, O / W and W / O emulsions, milks, pommades et onguents, pâtes, huiles corporelles, lotions ointments and ointments, pastes, body oils, lotions capillaires, shampooings, savons, sticks et crayons, sprays.  capillaries, shampoos, soaps, sticks and pencils, sprays. 10) Composition à usage cosmétique ou dermopharmaceutique, selon10) Composition for cosmetic or dermopharmaceutical use, according to les revendications 8 et 9 caractérisée en ce que les composés, claims 8 and 9 characterized in that the compounds, selon revendications 1 à 5, sont incorporés dans des vecteurs according to claims 1 to 5, are incorporated into vectors comme les liposomes, les chylomicrons, les macro-, such as liposomes, chylomicrons, macro-, micro- et nanoparticules ainsi que les macrn-, micro- et micro- and nanoparticles as well as macrn-, micro- and nanocapsules, ou absorbés sur des polymères organiques nanocapsules, or absorbed on organic polymers poudreux, les talcs, bentonites et autres supports minéraux.  powdery, talcs, bentonites and other mineral supports.
FR9303055A 1993-03-15 1993-03-15 New synthetic compounds, process for obtaining them and use in cosmetic and dermopharamceutical preparations to improve tanning. Expired - Lifetime FR2702766B1 (en)

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WO2010082175A2 (en) 2009-01-16 2010-07-22 Sederma New compounds, in particular peptides, compositions comprising them and cosmetic and dermopharmaceutical uses
WO2010082176A2 (en) 2009-01-16 2010-07-22 Sederma Cosmetic composition containing kxk type peptides and uses
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US8361516B2 (en) 2006-08-03 2013-01-29 Sederma Composition comprising sarsasapogenin
US8404648B2 (en) 2006-02-16 2013-03-26 Sederma Polypeptides KXK and their use
US8507649B2 (en) 2006-05-05 2013-08-13 Sederma Cosmetic compositions comprising at least one peptide with at least one immobilized aromatic cycle
WO2014080376A2 (en) 2012-11-26 2014-05-30 Sederma Pro-pigmenting peptides
US8741357B2 (en) 2005-01-14 2014-06-03 Sederma Sas Cosmetic or dermopharmaceutical composition comprising an euglena extract
US8846019B2 (en) 2005-09-06 2014-09-30 Sederma Use of protoberberines as an active substance regulating the pilosebaceous unit
US9050477B2 (en) 2009-04-17 2015-06-09 Sederma Cosmetic compositions comprising oridonin and new cosmetic uses
FR3031301A1 (en) * 2015-01-05 2016-07-08 Jean-Noel Thorel NOVEL COMPOSITION COMPRISING CHROMIUM AND TYROSINE DERIVATIVES FOR SKIN TREATMENT
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2198042A (en) * 1986-12-03 1988-06-08 Induchem Ag Cosmetic sunscreen composition containing tyrosine derivatives
EP0313446A2 (en) * 1987-10-19 1989-04-26 Bioeurope Water soluble L-tyrosine derivatives and process for their preparation
WO1990014429A1 (en) * 1989-05-25 1990-11-29 Novo Nordisk A/S An enzyme-catalyzed process for preparing n-acyl amino acids and n-acyl amino acid amides
JPH03181417A (en) * 1989-12-12 1991-08-07 Nikko:Kk Local antimicrobial agent
EP0500332A2 (en) * 1991-02-19 1992-08-26 National Food Research Institute Ministry Of Agriculture, Forestry And Fisheries Novel acylamino acid compounds and a method for their production

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2198042A (en) * 1986-12-03 1988-06-08 Induchem Ag Cosmetic sunscreen composition containing tyrosine derivatives
EP0313446A2 (en) * 1987-10-19 1989-04-26 Bioeurope Water soluble L-tyrosine derivatives and process for their preparation
WO1990014429A1 (en) * 1989-05-25 1990-11-29 Novo Nordisk A/S An enzyme-catalyzed process for preparing n-acyl amino acids and n-acyl amino acid amides
JPH03181417A (en) * 1989-12-12 1991-08-07 Nikko:Kk Local antimicrobial agent
EP0500332A2 (en) * 1991-02-19 1992-08-26 National Food Research Institute Ministry Of Agriculture, Forestry And Fisheries Novel acylamino acid compounds and a method for their production

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 9138, Derwent Publications Ltd., London, GB; AN 91-276708 & JP-A-3 181 417 (NIKKO KK) *
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. vol. 112, no. 9, 25 Avril 1990, GASTON, PA US pages 3547 - 3554 NOEL G. HARVEY ET AL. 'Chiral Molecular Recognition in the Thermodynamics of Spreading and transition for Racemic and Enantiomeric Stearoyltyrosine films' *
SEIFEN, OLE, FETTE, WACHSE vol. 116, no. 10, 5 Juillet 1990, AUGSBURG, DE pages 406 - 410 W. TUR 'Kosmetische Wirkstoffkomplexe für Sonnenschutzpräparate,...' *

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US8741357B2 (en) 2005-01-14 2014-06-03 Sederma Sas Cosmetic or dermopharmaceutical composition comprising an euglena extract
US8846019B2 (en) 2005-09-06 2014-09-30 Sederma Use of protoberberines as an active substance regulating the pilosebaceous unit
US8404648B2 (en) 2006-02-16 2013-03-26 Sederma Polypeptides KXK and their use
US8507649B2 (en) 2006-05-05 2013-08-13 Sederma Cosmetic compositions comprising at least one peptide with at least one immobilized aromatic cycle
US8361516B2 (en) 2006-08-03 2013-01-29 Sederma Composition comprising sarsasapogenin
WO2010067327A1 (en) 2008-12-11 2010-06-17 Sederma Cosmetic composition containing acetylated oligoglucuronans
WO2010082176A2 (en) 2009-01-16 2010-07-22 Sederma Cosmetic composition containing kxk type peptides and uses
US8697656B2 (en) 2009-01-16 2014-04-15 Sederma Compounds, in particular peptides, compositions comprising them and cosmetic and dermo-pharmaceutical uses
WO2010082175A2 (en) 2009-01-16 2010-07-22 Sederma New compounds, in particular peptides, compositions comprising them and cosmetic and dermopharmaceutical uses
US9050477B2 (en) 2009-04-17 2015-06-09 Sederma Cosmetic compositions comprising oridonin and new cosmetic uses
WO2010136965A2 (en) 2009-05-26 2010-12-02 Sederma Cosmetic use of tyr-arg dipeptide to combat cutaneous sa
WO2014080376A2 (en) 2012-11-26 2014-05-30 Sederma Pro-pigmenting peptides
US9534015B2 (en) 2012-11-26 2017-01-03 Sederma Pro-pigmenting peptides
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FR3031301A1 (en) * 2015-01-05 2016-07-08 Jean-Noel Thorel NOVEL COMPOSITION COMPRISING CHROMIUM AND TYROSINE DERIVATIVES FOR SKIN TREATMENT
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