FR2964866A1 - Use of new of known at least one ortho-diphenol compound as antidandruff agent to treat dandruff associated with the proliferation of Malassezia yeasts on the scalp - Google Patents

Abstract

Use of at least one ortho-diphenol compound (I) and their salts and solvates as antidandruff agent, is claimed. Use of at least one ortho-diphenol compound of formula (I) and their salts and solvates as antidandruff agent, is claimed. R1-R4 : H, halo, carboxyl group (COOH), 1-6C alkyl carboxylate group of formula (COOR), amine group of formula (NRR1a), linear 1-40C or branched 3-40C alkyl group (saturated) (optionally one or more non-adjacent carbon atoms are replaced by a divalent radical comprising -NR7, -S-, -O- and/or -C(O)-, preferably -OC(O)-, -C(O)-O-, -C(O)-NR7-, -NR7-C(O)- and/or -NR7-C(O)-NR7-, and optionally substituted by one or more OH and/or aryl group, which is optionally substituted by one or more 1-6C alkyl group, OH or NRR1a), linear 2-40C or branched 3-40C (poly)alkenyl group having one or more unsaturations (optionally one or more non-adjacent carbon atoms are replaced by a divalent radical comprising -NR7, -S-, -O- and/or -C(O)-, preferably -OC(O)-, -C(O)-O-, -C(O)-NR7-, -NR7-C(O)- and/or -NR7-C(O)-NR7-, and optionally substituted by one or more OH and/or aryl group, which is optionally substituted by one or more 1-6C alkyl group, OH or NRR1a), or aryl group (optionally substituted by one or more 1-30C alkyl group optionally one or more non-adjacent carbon atoms are replaced by divalent radical comprising -NR7, -S-, -O- and/or -C(O)-, preferably -OC(O)-, -C(O)-O-, -C(O)-NR7-, -NR7-C(O)- and/or -NR7-C(O)-NR7-), preferably R1, R3 and R4 is H; R7 : H or 1-6C alkyl, optionally substituted by one or more 1-4C alkyl and/or OH; and R, R1a : H or 1-6C alkyl group. Provided that at least one of R1-R4 is different from H. An independent claim is included for ortho-diphenol compound of formula (Iaa) or (Ibb) and their salts or solvates. R8 : H or 1-4C alkyl, preferably H; Y1 : saturated linear 1-10C or branched 2-10C alkyl group; Z1 : linear 15-30C or branched 15-30C alkyl group (optionally one or more non-adjacent carbon atoms are replaced by a divalent radical comprising -NR7, -S-, -O- and/or -C(O)-, preferably -OC(O)-, -C(O)-O-, -C(O)-NR7-, -NR7-C(O)- and/or -NR7-C(O)-NR7-, and optionally substituted by one or more OH and/or aryl group, which is optionally substituted by one or more 1-6C alkyl group or OH), or linear 15-30C or branched 15-30C (poly)alkenyl group (optionally one or more non-adjacent carbon atoms are replaced by a divalent radical comprising -NR7, -S-, -O- and/or -C(O)-, preferably -OC(O)-, -C(O)-O-, -C(O)-NR7-, -NR7-C(O)- and/or -NR7-C(O)-NR7-, and optionally substituted by one or more OH and/or aryl group, which is optionally substituted by one or more 1-6C alkyl group, or OH); Z2 : linear 9-30C or branched 9-30C alkyl group (optionally one or more non-adjacent carbon atoms are replaced by a divalent radical comprising -NR7, -S-, -O- and/or -C(O)-, preferably -OC(O)-, -C(O)-O-, -C(O)-NR7-, -NR7-C(O)- and/or -NR7-C(O)-NR7-, and optionally substituted by one or more OH and/or aryl group, which is optionally substituted by one or more 1-6C alkyl group or OH), or linear 9-30C or branched 9-30C (poly)alkenyl group (optionally one or more non-adjacent carbon atoms are replaced by a divalent radical comprising -NR7, -S-, -O- and/or -C(O)-, preferably -OC(O)-, -C(O)-O-, -C(O)-NR7-, -NR7-C(O)- and/or -NR7-C(O)-NR7-, and optionally substituted by one or more OH and/or aryl group, which is optionally substituted by one or more 1-6C alkyl group, or OH); and R7 : H or 1-6C alkyl, optionally substituted by one or more 1-4C alkyl and/or OH. Provided that (I) excludes (E)-3-(3,4-dihydroxy-phenyl)-N-((Z)-octadec-9-enyl)-acrylamide. [Image] [Image] ACTIVITY : Dermatological. MECHANISM OF ACTION : None given.

Description

Use as antidandruff of ortho-diphenol derivatives, novel compounds and cosmetic composition comprising them

The present invention relates to the use of the particular ortho-diphenol derivatives as an anti-dandruff agent, in particular in the cosmetic treatment of dandruff conditions related to the excessive proliferation of yeasts of the genus Malassezia on the scalp. The invention also relates to a cosmetic treatment method for eliminating and / or reducing dandruff, in particular that caused by yeasts of the genus Malassezia, employing said derivatives. The invention also relates to novel ortho-diphenol derivatives and the cosmetic compositions comprising them.

Dandruff problems affect up to 50% of the world's population. They affect men as well as women and are perceived as having a very negative psychosocial impact. The appearance of dandruff is inconvenient both from the point of view of aesthetics and the inconvenience it causes (itching, redness, etc.), so that many people confronted with this problem to varying degrees wish to get rid of it. effective and definitive.

Dandruff is an excessive and visible desquamation of the scalp, resulting from the rapid multiplication of epidermal cells and their abnormal maturation. This phenomenon can be provoked in particular by microtrauma of a physical or chemical nature, such as overly aggressive hair treatments, extreme weather conditions, nervousness, diet, fatigue, pollution; but it has been shown that dandruff conditions are most often the result of a disorder of the microflora of the scalp, and more particularly the excessive colonization of a fungus which belongs to the family of yeasts of the genus Malassezia (formerly called Pytirosporum ovale). ) and that is naturally present on the scalp.

Many anti-dandruff treatments have been developed with the main goal of eradicating Malassezia yeasts from the scalp. Thus, the activity of today's major anti-dandruff active agents, such as zinc pyrithione, piroctone olamine or selenium disulfide, is based primarily on their fungicidal properties. However, these anti-dandruff agents are not totally satisfactory in terms of effectiveness (immediate effectiveness or duration of the effect) and / or in terms of impact on the environment.

The object of the present invention is to provide non-irritating anti-dandruff agents for the skin and the scalp, which are as effective as the known anti-dandruff agents, while having a more favorable impact in terms of the environment (low bioaccumulation and good biodegradability in particular ). The invention also aims to propose active agents to restore the ecoflora of the scalp and in particular to prevent excessive colonization of the scalp by Malassezia sp. The Applicant has now found, surprisingly, that the use of at least one compound of formula (I) makes it possible to effectively treat the dandruff states, in particular those associated with the proliferation of yeasts of the genus Malcesia, and to remedy the disadvantages. of the prior art. It has been observed that by employing the compounds of formula (I), it is possible to eliminate and / or reduce the number of yeasts of the genus Malassezia, the number of dandruff, as well as the itching and redness on the scalp.

The subject of the present invention is therefore the use, as anti-dandruff agent, of at least one compound of formula (I), as well as its salts and solvates, as defined below. The invention particularly relates to the use of these compounds for treating the dandruff conditions associated with the proliferation of yeasts of the genus Malassezia on the scalp. The invention also relates to a cosmetic treatment method for eliminating and / or reducing dandruff, in particular that caused by yeasts of the genus Malassezia, characterized in that it comprises the application to the hair and / or the scalp. of at least one compound as defined below or a cosmetic composition, in particular a capillary composition, comprising it. The invention also relates to certain novel compounds of formula (I ') or (II') as defined below, and the cosmetic compositions comprising them.

The compounds according to the invention thus correspond to the formula (I), as well as their salts and solvates: RI (I) HO R3 R4 in which R1 to R4, which may be identical or different, denote: - a hydrogen atom, - a halogen, - a carboxyl radical (COOH); a C1-C6 alkyl carboxylate radical (COOR); an NRR 'radical with R and R', independently of one another, representing H or C 1 -C 6 alkyl; a linear (saturated) C1-C40 or branched C3-C40 alkyl radical, in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from: -NR7, -S-, -O- and -C (O) - and combinations thereof, such as -OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7- C (0) -NR 7; and / or said alkyl radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, identical or otherwise, chosen from C1-C6 alkyls and OH and NRR ';

a C2-C40 or branched C3-C40 linear (poly) alkenyl radical (one or more unsaturations), in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from: -NR7, -S -, - 0- and -C (O) - and combinations thereof, such as -OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (0) -, -NR7-C (O) -NR7-; and / or said alkenyl radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, which may be identical or different, chosen from C1-C6 alkyls and OH and NRR ';

an aryl group, optionally substituted with one or more C1-C30 alkyl radicals in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from: -NR7, -S-, -O- and -C (0) - and combinations thereof, such as -OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7-C ( 0) -NR7-;

in all these radicals, R7 denoting a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more C1-C4 and / or OH alkyls; it being understood that at least one of the radicals R1, R2, R3 and / or R4 is different from hydrogen.

Preferably, in the formula (I), R1 = R2 = R3 = H or else R1 = R3 = R4 = H.

Preferably, in the formula (I), the radical or radicals R1 to R4 different from hydrogen, are chosen from: a linear (saturated) C2-C32, in particular C6-C30 or even C8-C28 alkyl radical, or branched C3-C32, especially C6-C30 or C8-C28, in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from -NR7, -O-, -OC (0) -, -C (O) O-, -C (O) NR7-, -NR7-C (O) -; and / or said alkyl radical being optionally substituted by an aryl, itself substituted or not by one or more radicals, identical or different, chosen from C1-C6 alkyls and OH and NRR 'radicals; and a (poly) alkenyl radical (one or more C = C unsaturations, especially one or two unsaturations) linear C2-C32, in particular C6-C30, even C8-C28, or branched C3-C32, in particular C6-C30 or C8-C28, in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from -NR7, -O-, -OC (O) -, -C (O) O-, -C ( 0) NR7-, -NR7-C (O) -; and / or said alkenyl radical being optionally substituted by an aryl, itself substituted or not by one or more radicals, which may be identical or different, chosen from C1-C6 alkyls and OH and NRR 'radicals.

Preferably, the compounds of the invention correspond to the following formulas (II) or (III), as well as their salts and / or solvates: ## STR2 ## in which: t = 0 or 1; X is -NR8- or -O-, with R8 = H or C1-C4 alkyl; Y denotes a linear saturated hydrocarbon chain C1-C10 or branched C2-C10; and Z denotes: (i) a linear C 1 -C 30 or branched C 3 -C 30 alkyl radical; in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from -NR7, -S-, -O- and -C (O) - and combinations thereof, in particular such as -OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7-C (O) -NR7-; said radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, which may be identical or different, chosen from C1-C6 alkyls and OH radicals; R7 denoting a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more C1-C4 and / or OH alkyls; or (ii) a C2-C30 or branched C3-C30 linear (poly) alkenyl radical; in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from -NR7, -S-, -O- and -C (O) - and combinations thereof, in particular such as -OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7-C (O) -NR7-; said radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, which may be identical or different, chosen from C1-C6 alkyls and OH radicals; R7 denoting a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more C1-C4 and / or OH alkyls.

Preferably, in formula (II): X = O or NH; and / or - Z denotes: (i) a linear C 1 -C 22, in particular C 4 -C 20, or branched C 3 -C 22, in particular C 4 -C 20, alkyl radical; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NH- and -O- and combinations thereof; said radical being optionally substituted with one or more OH and / or phenyl; or (ii) a linear (poly) alkenyl C2-C22, in particular C4-C20 or branched C3-C22, especially C4-C20 radical; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from - NH- and -O- and combinations thereof; said radical being optionally substituted by one or more OH and / or phenyl.

Preferably, in formula (III), - X = O or NH; and / or Y denotes a linear saturated hydrocarbon chain C1-C4, preferably -CH2-CH2-; and / or - Z denotes: (i) a linear C 1 -C 22, in particular C 4 -C 20 or branched C 3 -C 22, in particular C 4 -C 20, alkyl radical; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NH- and -O- and combinations thereof; said radical being optionally substituted with one or more OH and / or phenyl; or (ii) a linear (poly) alkenyl C2-C22, in particular C4-C20 or branched C3-C22, especially C4-C20 radical; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from - -NH- and -O- and combinations thereof; said radical being optionally substituted by one or more OH and / or phenyl.

Among the compounds corresponding to formula (I), mention may be made of the following compounds, as well as their salts and / or solvates: Compound HO name O octadecyl (2E) -3- (3,4-HO dihydroxyphenyl) prop-2- enoate HO o (2E) -3,7,11,15-HO ® tetramethylhexadec-2-en-1-yl (2E) -3- (3,4-dihydroxyphenyl) prop-2-enoate HO o docosyl (2E) 3- (3,4-HO ® / O dihydroxyphenyl) prop-2-enoate HO (2E) -3- (3,4-Ho H dihydroxyphenyl) -N-octadecyl prop-2-enamide HO o (2E ) N-2- [2- (3,4-HO N-dihydroxyphenyl) ethyl] hexadecanamide N- [2- (3,4-HO N-dihydroxyphenyl) -ethyl] -docosanamide HO (2E) -3- (3,4-HO dihydroxyphenyl) -N-octylpropyl N- [2- (3,4-HO N dihydroxyphenyl) ethyl] 2-enamide HO-Butyl (2E) -3- (3,4-Ho / dihydroxyphenyl) prop-2-enoate HO O2-phenylethyl (2E) -3-HO (3,4-dihydroxyphenyl) prop-2- enoate HO O Methyl (2E) -3- (3,4-HO 3 -CHH dihydroxyphenyl) prop-2-dihydroxyphenyl) prop-2-enoate Of course we can use a mixture of compounds of formula (I).

The salts and solvates of the compounds of formula (I) are also part of the present invention.

The salts include conventional non-toxic salts of said compounds such as those formed from organic or inorganic acids. There may be mentioned salts of mineral acids, such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid and boric acid. It is also possible to mention the salts of organic acids, which may comprise one or more carboxylic acid, sulphonic or phosphonic acid groups. It may be linear, branched or cyclic aliphatic acids or aromatic acids. These acids may furthermore comprise one or more heteroatoms chosen from 0 and N, for example in the form of hydroxyl groups. In particular, propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid may be used. Among the organic or inorganic base salts, mention may be made of triethanolamine, aminopropanediol, sodium, zinc or calcium salts. The solvates acceptable for the cosmetic use of the compounds according to the invention comprise conventional solvates such as those formed during the last step of preparation of said compounds due to the presence of solvents. There may be mentioned solvates due to the presence of water or linear or branched alcohols such as ethanol or isopropanol.

Some of the compounds of formula (I) are novel and form an object as such of the present invention. Cosmetic compositions comprising in a cosmetically acceptable medium at least one such novel compound form another subject of the invention.

The novel compounds correspond to one of the following formulas (I ') and (II'), their salts and solvates being included: ## STR1 ## in which: R8 = H or alkyl C1-C4, preferably H1-Y denotes a linear saturated hydrocarbon chain C1-C10 or branched C2-C10;

Z1 denotes: (i) a linear C15-C30 or branched C15-C30 alkyl radical; in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from -NR7, -S-, -O- and -C (O) - and combinations thereof, in particular such as -OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7-C (O) -NR7-; said alkyl radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, which may be identical or different, chosen from C1-C6 alkyls and OH radicals; R7 denoting a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more C1-C4 and / or OH alkyls; or (ii) a C15-C30 or branched C15-C30 linear (poly) alkenyl radical; in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NR7, -S-, -O- and-C (O) - and combinations thereof, such as -OC ( 0) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7- C (O) -NR7-; said alkenyl radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, identical or different, chosen from C1-C6 alkyls and OH radicals; R7 denoting a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more C1-C4 and / or OH alkyls; Z2 denotes: (i) a linear C9-C30 or branched C9-C30 alkyl radical; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NR7, -S-, -O- and-C (O) - and combinations thereof, such as -OC (0) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7-C (O) -NR7-; said alkyl radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, which may be identical or different, chosen from C1-C6 alkyls and OH radicals; R7 denoting a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more C1-C4 and / or OH alkyls; or (ii) a C9-C30 or branched C9-C30 linear (poly) alkenyl radical; in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from -NR7, -S-, -O- and -C (O) - and combinations thereof, in particular such as -OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7-C (O) -NR7-; said radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, which may be identical or different, chosen from C1-C6 alkyls and OH radicals; R7 denoting a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more C1-C4 and / or OH alkyls; the following compound being excluded: Preferably, in the formula (I '), Z1 denotes: (i) a linear C15-C22, in particular C16-C20, or branched C15-C22, in particular C16-C20; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NH- and -O- and combinations thereof; said radical being optionally substituted by one or more OH and / or phenyl; or (ii) a linear C15-C22, especially C16-C20 or branched C15-C22 (poly) alkenyl radical, especially C16-C20; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NH- and -O- and combinations thereof; said radical being optionally substituted by one or more OH and / or phenyl.

Preferably, in the formula (II '), Y denotes a saturated linear hydrocarbon chain C1-C4, preferably -CH2-CH2-; and / or - Z2 denotes: (i) a linear C9-C22, in particular C10-C20 or branched C9-C22, in particular C10-C20 alkyl radical; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NH- and -O- and combinations thereof; said radical being optionally substituted with one or more OH and / or phenyl; or (ii) a linear (poly) alkenyl radical C 9 -C 22, in particular C 10 -C 20 or branched C 9 -C 22, in particular C 10 -C 20; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NH- and -O- and combinations thereof; said radical being optionally substituted by one or more OH and / or phenyl.

The compounds of formula (I) can be obtained according to the synthetic routes described below. The functionalization of the COOH function in COYR function can be carried out according to the conventional methods of acid activation, in particular described in US Pat. "Comprehensive Organic Transformation of R. LAROCK Wiley 5th ed.", In the chapter 'Interconversion of nitriles, carboxylic acids and derivatives'; the reaction of the activated form is then carried out with RYH. Preferably, the activation methods are the formation of methyl ester or acid chloride, for example by the use of thionyl chloride or oxalyl chloride, or 1-chloron.n.2-trimethyl-1 -propenamine; or the formation of mixed anhydride for example with the aid of alkyl chloroformate; or the use of carbodiimides such as, for example, DCC, DIC or EDC; or else diethylcyanophosphate as described in "Phosphorus in organic synthesis-XI, Amino acids and peptides-XXI, Reaction of diethyl phosphorocyanidate with carboxylic acids A new synthesis of carboxylic esters and amides, Tetrahedron, 32, 1976, 2211-2217" . R5 + X-R6 R5 1 NR6 HO HO HO The amine is reacted with an alkylating agent such as, for example, a haloalkane, an alkyl mesylate or an alkyl tosylate. An ion exchange can be carried out if necessary after the reaction, by contact with an ion exchange resin chosen according to the desired exchanges. These resins are, for example, IRA 402 (alkyl sulphate exchange in chlorides), IRA 400 (iodide exchange in chloride). The alkylation can also be by reductive alkylation as described in Advanced Organic Chemistry, J March, 4th ed. p. 898-900; or addition by addition to a double bond, for example of Mickaël type as described in Advanced Organic Chemistry, J March, 4th ed. p. 768-770.

The compounds of formula (I) find a very particular application in the field of cosmetics, in particular capillary. They may be present in the cosmetic composition, in particular a capillary composition, in solubilized form, for example in water or an organic solvent, in particular ethanol, benzyl alcohol, butyl acetate, ethyl acetate or myristate. isopropyl, PEG (polyethylene glycols) liquid at 25 ° C, isododecane, vegetable oils, petroleum jelly, or in a silicone solvent such as volatile silicone oils, especially D5; as well as their mixtures. They may also be present in the form of an aqueous or organic or silicone dispersion, in particular in one of these solvents.

The cosmetic compositions according to the invention comprise a cosmetically acceptable medium, that is to say a medium that is compatible with keratin materials such as the skin of the face or of the body, the lips, the hair, the eyelashes, the eyebrows and the skin. nails.

Preferably, the compound of formula (I), alone or as a mixture, is present in an amount of 0.01 to 10%, preferably 0.1 to 5%, and more preferably 0.2 to 2% by weight. , relative to the total weight of the cosmetic composition. The compound (s) according to the invention are generally used for topical application. In particular, they may be used as anti-dandruff agents in a cosmetic composition which may be in any galenic form normally used for topical application. The cosmetic composition used according to the invention may be a hair composition, which may be rinsed or not rinsed. Said hair composition is preferably a shampoo, a cream, a mousse (aerosol or not), a paste, a gel, an emulsion, a lotion, a stick. Preferably, the cosmetic composition is a shampoo or a gel.

The cosmetic composition used according to the invention generally comprises a cosmetically acceptable mid-point. Preferably, said medium comprises water and / or one or more cosmetically acceptable organic solvents. The organic solvent (s) may be chosen from linear or branched C 1 -C 6 monoalcohols, such as ethanol, isopropanol, tert-butanol or n-butanol; polyols such as glycerol, propylene glycol, hexylene glycol (or 2-methyl-2,4-pentanediol), and polyethylene glycols; polyol ethers such as dipropylene glycol monomethyl ether; and their mixtures. Preferably, the cosmetic composition used according to the invention comprises an amount of organic solvents ranging from 0.05% to 60%, preferably from 0.5% to 50%, and more preferably from 1% to 40% by weight, relative to to the total weight of the cosmetic composition.

The cosmetically acceptable medium may further advantageously comprise thickeners; surfactants selected from anionic, cationic, nonionic and / or amphoteric or zwitterionic surfactants; conditioning agents; silicones; fall arrest agents; other anti-dandruff agents; oxidizing agents, vitamins; waxes, sunscreens, inorganic or organic pigments, colored or unstained; dyes; pearlescent and opacifying agents, sequestering agents, plasticizing agents, perfumes; conservatives. Of course, those skilled in the art will take care to choose this or these optional additional compounds and / or their quantity in such a way that the advantageous properties of the composition according to the invention are not, or not substantially, impaired by the addition envisaged. .

The subject of the invention is also a cosmetic treatment method intended to eliminate and / or reduce dandruff, in particular that caused by yeasts of the genus Malassezia, characterized in that it comprises the application, on the hair and / or the scalp, at least one compound of formula (I) and / or (I ') and / or (II'), or a cosmetic composition comprising at least one compound of formula (I) and / or I ') and / or (II'). The cosmetic composition may then be rinsed or not with water. Preferably, this cosmetic treatment process is repeated at least twice a week.

The invention is illustrated in more detail in the following examples.

Example 1 Compound 1: octadecyl (2E) -3- (3,4-dihydroxyphenyl) prop-2-enoate (synthesis described in Bioorganic and Medicinal Chemistry 2008, 16 (16), 7795-7803): A 2-fold solution is prepared % by weight of compound 1 in liquid modified Leeming and Notman (MLNA) as follows: 0.2048 g of compound 1 in 10 ml of liquid modified Leeming and Notman was weighed; solubilized by heating and use of Ultrasound. The test product solutions are twice as concentrated as the final test concentration, to account for the dilution upon contact with the Malassezia suspension. One of the previously prepared 2% solutions is diluted 1/2 in liquid modified Leeming and Notman to obtain a final test concentration of 0.5%; the other solution is used as it is (at 2%) to finally obtain a test concentration of 1%.

The Malassezia strains are contacted according to the table below: Growth control Test composition 0.5 ml strain 0.5 ml Test solution - 0.5 ml MLNA medium 0.5 ml - 20 ml deposits on the surface of MLNA agar, the mixture. Spread with a sterile rake all over the surface before recovering the excess. It is left in-cuber for at least 5 days at 30 ° C. The antifungal effect of the compound is evaluated by the lack of growth of the tested Malassezia strain. This inhibition is evaluated with respect to the growth control. Inhibitions are noted from 0 to 3, by assessing the density of the culture on the agar surface in comparison with the growth control, as follows: Notation Inhibition Interpretation 100% No growth 2 75% Growth < in the control box 1 25% Growth <in the control box 0 0% Growth comparable to the control box 30 The following results are obtained: Malassezia Malassezia restricta globosa Growth control Dense culture Dense culture Tests Test 1 Test 2 Test 1 Test 2 Compound 1 1% 2 2 1 1 0.5% 2 2 0 0 Example 2 Synthesis of compound 2: (2E) -3- (3,4-dihydroxyphenyl) -N-octadecylprop-2-enamide 10.3 g of N, N'-dicyclohexylcarbodiimide (50 mmol) to a solution of 9 g of (2E) -3- (3,4-dihydroxyphenyl) prop-2-enoic acid (caffeic acid) (50 mmol) and 13.5 g of octadecan-1-amine (octadecylamine) (50 mmol) in 600 ml of THF. The solution is stirred at 60 ° C for 3 hours. The final product is obtained by filtration and evaporation of the solvent, followed by drying under reduced pressure. 21 g (49 mmol) of the title compound are obtained in the form of a white powder with a yield of 97%.

1H NMR (DMSO): δ 0.8 ppm (t, 3H); 1.20 ppm (m, 32H); 3.16 ppm (t, 2H); 6.2 ppm (s, 1H); 6.44 ppm (s, 1H); 6.76 ppm (s, 1H); 6.94 ppm (s, 1H); 7.16 ppm (s, 1H); 7.34 ppm (s, 1H), 7.84 ppm (m, 2H), 8.8 ppm (m, 1H) Elemental Analysis: Measured:% C: 75.25,% H: 10.52,% N: 3.44,% O: 11.22 expected:% C: 75.13,% H: 10.51,% N: 3.24,% O: 11.12

Claims (15)

REVENDICATIONS1. Use, as anti-dandruff agent, of at least one compound of formula (I), and its salts and solvates: R1 (I) HO R3 R4 in which R1 to R4, which may be identical or different, denote: a hydrogen atom a halogen, a carboxyl radical (COOH); a C1-C6 alkyl carboxylate radical (COOR); an NRR 'radical with R and R', independently of one another, representing H or C 1 -C 6 alkyl; a linear (saturated) C1-C40 or branched C3-C40 alkyl radical, in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from: -NR7, -S-, -O- and -C (O) - and combinations thereof, such as -OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7- C (0) -NR 7; and / or said alkyl radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, identical or otherwise, chosen from C1-C6 alkyls and OH and NRR '; a C2-C40 or branched C3-C40 linear (poly) alkenyl radical (one or more unsaturations), in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from: -NR7, -S-, -O- and -C (O) - and combinations thereof, such as -OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (0) -, -NR7-C (O) -NR7-; and / or said alkenyl radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, which may be identical or different, chosen from C1-C6 alkyls and OH and NRR '; an aryl group, optionally substituted by one or more C1-C30 alkyl radicals in which, optionally, one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from: -NR7, -S-, -O- and -C (0) - and combinations thereof, such as -OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7-C ( 0) -NR7-; in all of these radicals, R7 denoting a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more C1-C4 and / or OH alkyls; it being understood that at least one of the radicals R1, R2, R3 and / or R4 is different from hydrogen. 2. Use according to claim 1, wherein in the formula (I), R1 = R2 = R3 = H or R1 = R3 = R4 = H. 3. Use according to one of the preceding claims, wherein, in the formula (I), the radical or radicals R1 to R4 different from hydrogen, are chosen from a linear C2- (saturated) alkyl radical. C32, in particular C6-C30, or even C8-C28, or branched C3-C32, in particular C6-C30, or even C8-C28, in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from -NR7, -O-, -OC (O) -, -C (O) O-, -C (O) NR7-, -NR7-C (O) -; and / or said alkyl radical being optionally substituted by an aryl, itself substituted or not by one or more radicals, identical or different, chosen from C1-C6 alkyls and OH and NRR 'radicals; and a (poly) alkenyl radical (one or more C = C unsaturations, in particular one or two unsaturations) linear C2-C32, in particular C6-C30, even C8-C28, or C3-C32, in particular C6 -C30 or C8-C28, wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NR7, -O-, -OC (O) -, -C (O) O-, - C (O) NR7-, -NR7-C (O) -; and / or said alkenyl radical being optionally substituted by an aryl, itself substituted or not by one or more radicals, which may be identical or different, chosen from C1-C6 alkyls and OH and NRR 'radicals. 4. Use according to one of the preceding claims, wherein the compound of formula (I) corresponds to one of the following formulas (II) or (III), and their salts and / or solvates: in which: - t = 0 or 1; X is -NR8- or -O-, with R8 = H or C1-C4 alkyl; Y denotes a linear saturated hydrocarbon chain C1-C10 or branched C2-C10; and Z denotes: (i) a linear C 1 -C 30 or branched C 3 -C 30 alkyl radical; in which optionally one or more non-adjacent carbon atoms are replaced by H 030 a divalent radical chosen from -NR7, -S-, -O- and -C (O) - and combinations thereof, especially such that -OC (0) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7-C (O) -NR7-; said radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, which may be identical or different, chosen from C1-C6 alkyls and OH radicals; R7 denoting a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more C1-C4 and / or OH alkyls; or (ii) a C2-C30 or branched C3-C30 linear (poly) alkenyl radical; in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from -NR7, -S-, -O- and -C (O) - and combinations thereof, in particular such as -OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7-C (O) -NR7-; said radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, which may be identical or different, chosen from C1-C6 alkyls and OH radicals; R7 denoting a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more C1-C4 and / or OH alkyls. 5. Use according to claim 4, wherein in the formula (II): X = O or NH; and / or - Z denotes: (i) a linear C 1 -C 22, in particular C 4 -C 20, or branched C 3 -C 22, in particular C 4 -C 20, alkyl radical; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NH- and -O- and combinations thereof; said radical being optionally substituted by one or more OH and / or phenyl; or (ii) a linear (poly) alkenyl C2-C22, in particular C4-C20 or branched C3-C22, especially C4-C20 radical; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from - NH- and -O- and combinations thereof; said radical being optionally substituted by one or more OH and / or phenyl. 6. Use according to claim 4, wherein in the formula (III), X = O or NH; and / or Y denotes a linear saturated C 1 -C 4 hydrocarbon-based chain, preferably -CH 2 -CH 2 -; and / or - Z denotes: (i) a linear C 1 -C 22, in particular C 4 -C 20 or branched C 3 -C 22, in particular C 4 -C 20, alkyl radical; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NH-and-O-40 and combinations thereof; said radical being optionally substituted with one or more OH and / or phenyl; or (ii) a linear (poly) alkenyl C2-C22, in particular C4-C20 or branched C3-C22, especially C4-C20 radical; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from - NH- and -O- and combinations thereof; said radical being optionally substituted by one or more OH and / or phenyl. 7. Use according to one of the preceding claims, wherein the compounds of formula (I) are chosen from the following compounds, and their salts and / or solvates: Compound HO name O octadecyl (2E) -3- (3, 4-OH dihydroxyphenyl) prop-2-enoate HO o (2E) -3,7,11,15-Ho-tetramethylhexadec-2-en-1-yl (2E) -3- (3,4-dihydroxyphenyl) prop-2-enoate HO o-docosyl (2E) -3- (3,4-Ho®-dihydroxyphenyl) prop-2-enoate HO o (2E) -3- (3,4-HOH dihydroxyphenyl) -N- octadecyl prop-2-enamide HO o (2E) -3- (3,4-HOH dihydroxyphenyl) -N-docosylprop-2-enamide HOC o N- [2- (3,4-HO N dihydroxyphenyl) ethyl] hexadecanamide N- [2- (3,4-OH N-dihydroxyphenyl) ethyl] octadecanamideH0, -O N- [2- (3,4-N dihydroxyphenyl) ethyl] docosanamide HO HO / H (2E) -3- ( 3,4-dihydroxyphenyl) -N-octylprop-2-enamide HO ®OH / d Butyl (2E) -3- (3,4-HO dihydroxyphenyl) prop-2-enoate HO o₂-phenylethyl (2E) ) HO (3,4-Dihydroxyphenyl) prop-2-enoate HO O Methyl (2E) -3- (3,4-HO-dihydroxy-3H) phenyl) prop-2-dihydroxyphenyl) prop-2-enoate 8. Use according to one of the preceding claims, for treating dandruff conditions associated with the proliferation of yeasts of the genus Malassezia on the scalp. 9. Use according to one of the preceding claims, wherein the compound of formula (I), alone or in admixture, is present in a hair cosmetic composition comprising a cosmetically acceptable medium. 10 10. Use according to one of the preceding claims, wherein the compound of formula (I), alone or in admixture, is present in an amount of 0.01 to 10%, preferably 0.1 to 5%, and better from 0.2 to 2% by weight, relative to the total weight of the cosmetic composition. 15 11. Cosmetic treatment process intended to eliminate and / or reduce dandruff, in particular that caused by yeasts of the genus Malassezia, characterized in that it comprises the application, on the hair and / or the scalp, of a minus a compound of formula (I) as defined in one of claims 1 to 7. 12. Compound corresponding to one of the following formulas (I ') and (II'), its salts and solvates being included: ## STR5 ## in which: R 8 = H or alkyl C1-C4, preferably H1-Y denotes a C1-C10 linear or branched C2-C10 saturated hydrocarbon-based chain, and - Z1 denotes: (i) a linear C15-C30 or branched C15 alkyl radical; -C30; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NR7, -S-, -O- and-C (O) - and combinations thereof, such as - OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7-C (O) -NR7-, said alkyl radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, which may be identical or different, chosen from C 1 -C 6 alkyls and OH radicals; R 7 denotes a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more alkyls C1-C4 and / or OH; or (ii) a C15-C30 or branched C15-C30 linear (poly) alkenyl radical; in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NR7, -S-, -O- and-C (O) - and combinations thereof, such as -OC ( 0) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7- C (O) -NR7-; said alkenyl radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, identical or different, chosen from C1-C6 alkyls and OH radicals; R7 denoting a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more C1-C4 and / or OH alkyls; Z2 denotes: (i) a linear C9-C30 or branched C9-C30 alkyl radical; in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from -NR7, -S-, -O- and -C (O) - and combinations thereof, in particular such as -OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7-C (O) -NR7-; Said alkyl radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, identical or otherwise, chosen from C1-C6 alkyls and OH radicals; R7 denoting a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more C1-C4 and / or OH alkyls; or (ii) a linear C9-C30 or branched C9-C30 (poly) alkenyl radical; in which optionally one or more non-adjacent carbon atoms are replaced by a divalent radical chosen from -NR7, -S-, -O- and -C (O) - and combinations thereof, in particular such as -OC (O) -, -C (O) -O-, -C (O) -NR7-, -NR7-C (O) -, -NR7-C (O) -NR7-; said radical being optionally substituted by one or more OH and / or by aryl, itself substituted or not by one or more radicals, which may be identical or different, chosen from C1-C6 alkyls and OH radicals; R7 denoting a hydrogen atom or a C1-C6 alkyl radical, optionally substituted with one or more C1-C4 and / or OH alkyls; the following compound being excluded: O 13. Compound according to claim 12, wherein, in the formula (I '), Z1 denotes (i) a linear C15-C22, in particular C16-C20, or branched C15-C22, in particular C16-C20; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NH- and -O- and combinations thereof; said radical being optionally substituted by one or more OH and / or phenyl; or (ii) a linear C15-C22, especially C16-C20 or branched C15-C22, especially C16-C20 (poly) alkenyl radical; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NH- and -O- and combinations thereof; said radical being optionally substituted by one or more OH and / or phenyl. 14. A compound according to claim 12, wherein in the formula (II '), Y denotes a linear saturated hydrocarbon chain C1-C4, preferably -CH2-CH2-; and / or - Z2 denotes: (i) a linear C9-C22, in particular C10-C20 or branched C9-C22, in particular C10-C20 alkyl radical; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NH- and -O- and combinations thereof; said radical being optionally substituted with one or more OH and / or phenyl; or (ii) a linear (poly) alkenyl radical C 9 -C 22, in particular C 10 -C 20 or branched C 9 -C 22, in particular C 10 -C 20; wherein optionally one or more non-adjacent carbon atoms are replaced by a divalent radical selected from -NH- and -O- and combinations thereof; said radical being optionally substituted by one or more OH and / or phenyl. 15. Cosmetic composition comprising, in a cosmetically acceptable medium, at least one compound of formula (I ') or (II') as defined in one of the claims 40 to 40. HO HO 7 7