WO2006016014A1

WO2006016014A1 - Novel compounds of a 6-methyl-pyrimidine-2,4-diamine family, method for synthesising, compositions containing said compounds and the use thereof

Info

Publication number: WO2006016014A1
Application number: PCT/FR2004/001847
Authority: WO
Inventors: Philippe Breton; Maria Dalko; Serge Forestier; Géraldine Lerebour
Original assignee: L'oreal
Priority date: 2004-07-13
Filing date: 2004-07-13
Publication date: 2006-02-16

Abstract

The invention relates to novel compounds of a 6-methyl-pyrimidine-2,4-diamine family of formula (I), to a method for synthesising said compounds, to cosmetic or pharmaceutical compositions containing the inventive compounds and to the use thereof in the form of base neutralising agents, or active deodorants, or for treating acne and greasy skins or flakes of scurf.

Description

Novel compounds of the 6-methyl-pyrimidine-2,4-diamine family, synthetic process, compositions comprising them and uses

The invention relates to novel derivatives of the 6-methyl-2,4-diaminopyrimidine family, to their synthetic process and to their uses in cosmetic or pharmaceutical compositions, especially dermatological compositions, preferably intended for topical application. .

It is common to seek to introduce into the cosmetic or dermatological compositions, acidic additives or active agents which have the disadvantage of generating irritating side effects on the skin and / or of unstable reaction the composition in which they are introduced because of this acidi¬ té. In order to overcome these drawbacks, it is known to introduce into these compositions basic organic or inorganic neutralizing agents, in particular sodium hydroxide or triethanolamine. However, triethanolamine has a slight ammonia-like odor and a tendency to brown in contact with air and light, which does not always make it compatible in a composition, especially a cosmetic composition. The importance of having new basic neutralizing compounds which are compatible with a topical application to the skin and which do not have the disadvantages of the derivatives of the prior art is thus understood.

The Applicant has found, surprisingly and unexpectedly, that certain derivatives of the 6-methyl-2,4-diaminopyrimidine family have a basic function on the pyrimidine unit whose pKa value is greater than or equal to 7 , 5, which makes them compatible as basic neutralizing agents, especially in cosmetic or dermatological compositions.

Among the pyrimidine derivatives, 2-amino-4-morpholino-6-methylpyrimidine and 2-amino-4-piperidino-6-methylpyrimidine are already known, the synthetic procedures of which are described by Maggiolo et al in J. Am.Chem.Soc., 1950, pp. 376-381. This document, however, does not mention any particular use of these two compounds. DE19917784 discloses 6-trifluoromethyl-2,4-diamino-pyrimidine compounds comprising a benzyl or phenyl substituent, and their use for phytosanitary protection and the protection of technical materials (wood, leather, cardboard, textiles, wood glues) against bacteria, fungi and molds. DE3717480 discloses halogenated 2,6-diaminepyrimidine compounds and their use as herbicides and microbicides. The documents Egypt.J.Pharm.Sci., 1978, 28, (1-4), pp.117-126 and J.Chem.Soc.1986, pp.914-917 describe in particular the synthesis of compo¬ sés 6- methyl-pyrimidine-2,4-diamine whose amine in position 2 is substituted by aryl and report antimicrobial activities for some of these compounds. However, none of these documents mention the derivatives according to the invention, in the intended uses according to the invention.

An object of the present invention is constituted by new compounds of the family of 6-methyl-pyrimidine-2,4-diamine, and corresponding to the formula (I).

Another subject of the present invention is a cosmetic, der¬ matological or pharmaceutical composition comprising, in a physiologically acceptable medium, at least one compound of the 6-methyl-pyrimidine-2,4-diamine family, formula (I) as defined below.

Yet another object of the invention is a process for preparing said com¬ poses of formula (I).

Another subject of the invention is the use of at least one compound of formula (I) as basic neutralizing agent.

Furthermore, in the field of cosmetics, it is well known to use, in topical application, deodorant products containing active substances of the antiperspirant or bactericidal type in order to reduce, or even eliminate, generally unpleasant axillary odors.

Antiperspirant substances have the effect of limiting the flow of sweat. They generally consist of aluminum salts which, on the one hand, are irritating to the skin and which, on the other hand, reduce the flow of sweat by modifying skin physiology, which is unsatisfactory.

The bactericidal substances inhibit the development of cutaneous flora responsible for axillary odors. Of the bactericidal products, the most commonly used is Triclosan (2,4,4'-trichloro-2'-hydroxydiphenyl ether), which has the disadvantage of significantly modifying the ecology of the cutaneous flora. be inhibited by certain compounds, such as nonionic surfactants, commonly used in the formulation of cosmetic compositions. In addition, the insoluble nature of Triclosan in water does not allow its incorporation into essentially aqueous formulas. In order to achieve long-term effectiveness, new products with a deodorant action, that is, products that are capable of modifying, reducing and / or removing or preventing the development, are sought. body odor (this definition is given in the book "Cosmetic Science and Technology Series" - 1988 / Volume 7 chap.10 - IHc). In addition, products which do not have the drawbacks of the active substances used in the prior art are sought.

After much research on the subject, the Applicant has now unexpectedly and surprisingly found that the compounds of formula (I) according to the invention have the property of preventing the development of body sweat odors, without the disadvantages of the active substances previously used in the deodorant compositions.

The compounds of formula (I) according to the invention have the advantage of being effective in terms of deodorant activity, of being odorless at the concentrations of use, and of respecting the cutaneous bacterial flora.

Thus, the subject of the present invention is the use of a compound of formula (I) as a deodorant active agent in a cosmetic composition or in the preparation of a cosmetic composition.

The subject of the invention is also the use of at least one compound of formula (I) described below for the manufacture of deodorant cosmetic products intended for human topical application.

The invention also relates to a process for treating human axillary odors comprising applying to the axillary surface an effective amount of deodorant composition comprising at least one compound of formula (I).

It also relates to a method for treating human axillary odors, comprising applying to the axillary surface an effective amount of at least one compound of formula (I).

The invention also relates to a deodorant cosmetic composition comprising in a cosmetically acceptable medium at least one compound of formula (I).

For the purposes of the present invention, the term "deodorant active agent" means any substance capable of reducing the flow of sweat and / or of masking, improving or reducing the unpleasant odor resulting from the decomposition of human sweat by bacteria.

Furthermore, the Applicant has also unexpectedly and surprisingly found that the compounds according to the invention have good acne and skin imperfection properties related to hyperseborrhoea. not predictable by reading the above documents.

The secretion of sebum is a normal phenomenon and useful to the skin. However, during adolescence in particular, hypersecretion of sebum and disruption of the keratinization of the pilosebaceous follicle may occur. consequences obstruction of the pilosebaceous follicle and the formation of com¬¬ donations.

Anaerobic bacteria proliferate in this environment rich in sebum and follicular cells and can locally produce inflammation, by the release of lipases that leads to the formation of free fatty acids. These are themselves comedogenic and primary irritants.

To combat these pathogens, active agents such as triclosan, hexamidine, hexetidine and benzalkonium chloride are commonly used. But the use of these assets is not devoid of side effects. Thus, triclosan has been found to be insufficiently effective in certain vehicles where its activity is inhibited by surfactants. Hexamidine and hexetidine in the form of salts are sensitizing substances that can cause allergies. Furthermore, benzalkonium chloride can be irritating at usual doses of use. In addition, it destabilizes compositions containing anionic surfactants.

The Applicant has also discovered that the compounds of formula (I) may find an application in the treatment against acne and skin imperfections related to hyperseborrhoea.

The subject of the present invention is therefore a process for the cosmetic treatment of cutaneous imperfections of oily skin comprising the topi¬ application on the skin of a composition comprising, in a physiologically acceptable medium, at least one compound of formula (I ).

The subject of the present invention is also the use of a compound of formula (I) for the preparation of a composition intended for the treatment of acne.

Furthermore, the Applicant has also unexpectedly and surprisingly discovered that the compounds of formula (I) have anti-dandruff properties.

The subject of the invention is therefore also a process for the cosmetic treatment of hair films comprising the topical application to the scalp of a composition comprising, in a physiologically acceptable medium, at least one compound of formula (I).

It also relates to the use of compound of formula (I) for the preparation of a composition for the treatment of films.

In contrast to the compounds of the prior art, the compounds according to the invention have the advantage of not comprising aryl groups derived from aromatic amines, especially compounds of aniline and / or Halogenated aryl moieties, especially chlorinated or fluorinated. These substituents are well known for generating cutaneous irritations and chlorinated and / or fluorinated aryl compounds are known to be ecotoxic.

Furthermore, the compounds according to the invention have the advantage of a chemical structure clearly defined and characterized, hence reproducibility of their easy manufacture; their industrial feasibility is also quite simple. In addition, they have good solubility or compatibility with media commonly used in cosmetics, including aqueous media. In addition, they have the advantage of being odorless.

The compounds according to the present invention are therefore derivatives of the family of 6-methyl-2,4-diaminopyrimidine and correspond to the following formula (I):

in which R 1 and R ₂ , which are identical or different, represent:

a hydrogen atom, it being understood that R 1 and R ₂ do not simul¬ simultaneously represent a hydrogen atom,

a linear or branched, saturated or unsaturated, C 1 -C 20, advantageously C 1 -C 6, hydrocarbon radical which may be substituted with at least one radical chosen from:

(i) a radical -NH ₂ , -CN, -CF ₃ , -OZ or -COOZ with Z representing a hydrogen atom or a linear or branched, saturated or unsaturated C1-C4 alkyl radical, advantageously a methyl radical, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl;

(ii) an -NRR 'radical with R and R', which may be identical or different, represents a linear or branched, saturated or unsaturated C 1 -C 8 alkyl radical, advantageously C 1 -C 3; R and R 'taken together may form with the nitrogen atom a hetero ring, which may be aromatic, of 5, 6, 7 or 8 members may include at least one additional heteroatom selected from O, N and / or S said heterocycle, including the nitrogen atom, may be substituted with a C1-C6 alkyl chain, said alkyl chain may itself be substituted by at least one -NR ¹¹ R ¹ "radical with R"; and R '' represent independently of each other a hydrogen atom or a hydrocarbon radical, saturated or unsaturated, linear or branched C1-6;

(iii) a radical -Si (CH ₃ ) ₂ -OH; -Si (CH ₃ ) ₂ -OEt; -Si (CH ₃ ) ₂ -O-CH ₂ -Phenyl, - Si (CH ₃ ) ₂ -OMe or -Si (JPr) ₂ -OEt;

(iv) a 5-, 6-, 7- or 8-membered heterocycle comprising at least one heteroatom selected from O, N and / or S, said heterocycle, including nitrogen when it is present, which may be substituted by a C1-C6 alkyl chain, advantageously C1-C3;

(v) a 5-, 6-, 7- or 8-membered aromatic heterocycle comprising at least one heteroatom selected from O, N and / or S, said heterocycle may be substituted by a C1-C6 alkyl chain; preferably methyl, ethyl or propyl;

(vi) a cycloalkyl comprising 5, 6, 7 or 8 members, which may be substituted by a C 1 -C 6 alkyl chain which may itself be substituted with at least one radical -NR ¹¹ R " ¹ with R" and R '"independently of one another a hydrogen atom or a linear or branched, saturated or unsaturated C 1 -C 6 hydrocarbon-based radical, and / or a cycloalkyl comprising 5, 6, 7 or 8-membered rings;

- R 1 and R ₂ taken together capable of forming with the nitrogen atom a first non-aromatic heterocycle of 5, 6, 7 or 8 members which may comprise at least one additional heteroatom selected from O, N and / or S, said first heterocycle, including the nitrogen atom, which may be substituted by (a) a C 1 -C 6 alkyl chain which may itself be substituted by at least one radical -NR "R '" with R "and R"" independently of one another, a C1-C6 linear or branched, saturated or unsaturated hydrocarbon or hydrocarbon radical; and / or (b) a cycloalkyl or a second heterocycle, which may be aroma¬ tick, of 5, 6, 7 or 8 members, which may comprise at least one other heteroatom chosen from O, N and / or S, said ring or second heterocycle may be substituted with a C1-C6 alkyl chain; as well as their salts.

By linear or branched C1-C20 alkyl radical is meant according to the invention acyclic radicals resulting from the removal of a hydrogen atom in the molecule of a hydrocarbon, linear or branched having 1 to 20 carbon atoms. carbon and in particular the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl and octyl radicals, as well as their corresponding isomers of position.

By heterocycle is meant according to the invention a chain of atoms closed on itself and having at least one link (heteroatom) different from the others.

Advantageously according to the invention, the non-aromatic heterocycles of 5, 6, 7 or 8 members which may comprise at least one other heteroatom selected from oxygen and / or nitrogen and / or sulfur, are piperidine, piperazine, morpholine, pyridine, pyrrole, pyrazole, oxadiazole, thiadiazole, triazole, tetrazole, thiazole, imidazole, pyrimidine, furan, indole, benzimidazole, benzothioazole, benzofuran, benzothiophene, benzoxazole.

According to the invention, the second heterocycle, which may be aromatic and comprises 5, 6, 7 or 8 members, is advantageously chosen from piperidine, piperazine, morpholine, pyridine, pyrrole, pyrazole and oxadiazole. thiadiazole, triazole, tetrazole, thiazole, imidazole, pyrimidine, furan, indole, benzimidazole, benzothioazole, benzofuran, benzothiophene, benzoxazole.

Among the salts, in particular of mineral acid or of organic acid, compounds of formula (I), mention may be made of the salts obtained by adding the compound of formula (I) with a mineral acid chosen from hydrochloric acids, sulfuric, nitric and phosphoric acid, or with an organic acid selected from carbonic acid, acetic acid, succinic acid, fumaric acid, lactic acid, glycolic acid, citric acid, gluconic acid, salicylic acid and tartaric acid.

Preferably, R 1 represents hydrogen.

Preferably, R2 is a linear or branched, saturated or unsaturated, C1-C20, advantageously C1-C6, hydrocarbon radical which may be substituted with (i) -NH ₂ ,

(iv) a 5-, 6-, 7- or 8-membered heterocycle comprising at least one nitrogen heteroatom, said heterocycle, including nitrogen, possibly being substituted with a C1-C6 alkyl chain, advantageously with C1-C6 alkyl, C3;

(v) a 5-, 6-, 7- or 8-membered aromatic heterocycle comprising at least one oxygen heteroatom;

(vi) a cycloalkyl comprising 5, 6, 7 or 8 members, which may be substituted by a C 1 -C 6 alkyl chain which may itself be substituted with at least one -NH 2 radical.

Also preferably, R 1 and R ₂ taken together form with the nitrogen atom a first non-aromatic 5-, 6-, 7- or 8-membered heterocycle capable of com¬ taking at least one additional heteroatom of nitrogen, said first heterocycle, y including the nitrogen atom, which may be substituted by (a) a C 1 -C 6 alkyl chain which may itself be substituted by at least one -NR "R"'radical with R "and R'" representing, independently of one of the other, a linear or branched C 1 -C 6 saturated or unsaturated hydrocarbon radical; and / or (b) a cycloalkyl or a second heterocyclic, which may be aromatic, of 5, 6, 7 or 8 members, which may comprise at least one other heteroatom selected from O, said ring or second heterocycle may be substituted by a C1-C6 alkyl chain. Among the compounds corresponding to formula (I), the following compounds are particularly preferred:

4-N- [4- (methoxydimethylsilyl) butyl] -6-methyl-pyrimidine-2,4-diamine; 4-N- (4- (n-butyldimethylsilanol)) 6-methylpyrimidine-2,4-diamine; 4-N - [- [3- (ethoxydimethylsilyl) propyl] -6-methyl-pyrimidine-2,4-diamine; 4-N - [- [3- (ethoxydiisopropylsilyl) propyl] -6-methyl-pyrimidine-2,4-diamine; 4-N- [4-piperidinylmethyl] -6-methyl-pyrimidine-2,4-diamine; 4-N - [(2S) -2-pyrrolidinylmethyl] -6-methyl-pyrimidine-2,4-diamine; 4-N - [- [1-ethylpyrrolidinyl-2-ylmethyl] -6-methyl-pyrimidine-2,4-diamine; 4-methyl-6- [4- (3-pyrrolidin-1-yl-propyl) - [1,4] diazepan-1-yl] -pyrimidin-2-ylamine

4-Methyl-6- (4-methyl- [1,4] diazepan-1-yl) -pyrimidin-2-ylamine

2- [4- (2-Amino-6-methyl-pyrimidin-4-yl) - [1,4] diazepan-1-yl] ethanol;

4- (4-Butyl- [1,4] diazepan-1-yl) -6-methyl-pyrimidin-2-ylamine;

4-Methyl-6- (4-phenethyl- [1,4] diazepan-1-yl) -pyrimidin-2-ylamine; 4- {4- [2- (4-Fluoro-phenyl) -ethyl] - [1,4] diazepan-1-yl} -6-methyl-pyrimidin-2-ylamine

4-Methyl-6- [4- (3-trifluoromethyl-pyridin-2-yl) - [1,4] diazepan-1-yl] pyrimidin-2-ylamine

4- [4- (2-dimethylamino-ethyl) -piperazin-1-yl] -6-methyl-pyrimidin-2-ylamine; 4-Methyl-6- (4-methyl-piperazin-1-yl) -pyrimidin-2-ylamine;

2- [4- (2-Amino-6-methyl-pyrimidin-4-yl) -piperazin-1-yl] ethanol;

3- [4- (2-Amino-6-methyl-pyrimidin-4-yl) -piperazin-1-yl] -propionitrile;

4- [4- (2-Methoxy-ethyl) -piperazin-1-yl] -6-methyl-pyrimidin-2-ylamine;

4- (4-Cyclopentyl-piperazin-1-yl) -6-methyl-pyrimidin-2-ylamine; 4- [4- (3-Methoxy-propyl) -piperazin-1-yl] -6-methyl-pyrimidin-2-ylamine;

4-Methyl-6- (4-phenyl-piperazin-1-yl) -pyrimidin-2-ylamine;

4-Methyl-6- (4-pyridin-2-yl-piperazin-1-yl) -pyrimidin-2-ylamine;

4-Methyl-6- (4-pyrimidin-2-yl-piperazin-1-yl) -pyrimidin-2-ylamine;

4-Methyl-6- (2,3,5,6-tetrahydro- [1,2 '] bipyrazinyl-4-yl) -pyrimidin-2-ylamine; 4- (4-Cyclohexyl-piperazin-1-yl) -6-methyl-pyrimidin-2-ylamine;

4- (4-Hexyl-piperazin-1-yl) -6-methyl-pyrimidin-2-ylamine; 4-N - [- (2-amino-2-methyl-propyl) -6-methyl-pyrimidine-2,4-diamine; 4-N - [- (2-piperazin-1-yl-ethyl) -6-methyl-pyrimidine-2,4-diamine; 4-N - [- (5-methyl-furan-2-ylmethyl) -6-methyl-pyrimidine-2,4-diamine; 4-N - [(Furan-2-ylmethyl-) 6-methylpyrimidine-2,4-diamine;

4-Methyl-6- [4- (1-methyl-piperidin-4-yl) -piperazin-1-yl] -pyrimidin-2-ylamine;

4-Methyl-6- (4-imidazol-2-yl-piperazin-1-yl) -pyrimidin-2-ylamine; 4-N - [- (3-aminomethylcyclohexylmethyl) -6-methylpyrimidine-2,4-diamine; 4-Methyl-6-piperidin-1-yl-pirimidin-2-ylamine; 4-Methyl-6-pyrrolidin-1-yl-pyrimidin-2-ylamine;

1- (2-Amino-6-methyl-pyrimidin-4-yl) -pyrrolidin-3-ol;

- [1- (2-Amino-6-methyl-pyrimidin-4-yl) -pyrrolidin-3-yl] -methanol;

4-Methyl-6- (2-methyl-pyrrolidin-1-yl) -pyrimidin-2-ylamine; 4- (2-Isopropyl-pyrrolidin-1-yl) -6-methyl-pyrimidin-2-ylamine;

1- (2-Amino-6-methyl-pyrimidin-4-yl) -pyrrolidine-2-carbonitrile;

4-Methyl-6- (3-phenyl-pyrrolidin-1-yl) -pyrimidin-2-ylamine; 4-Methyl-6- (3-pyridin-3-yl-pyrrolidin-1-yl) -pyrimidin-2-ylamine; 4-Methyl-6- (3-pyridin-2-yl-pyrrolidin-1-yl) -pyrimidin-2-ylamino; 4-N-Hexyl-6-methyl-pyrimidine-2,4-diamine.

The compounds of formula (I) are novel compounds with the exception of 2-amino-4-morpholino-6-methylpyridine and 2-amino-4-piperidino-6-methylpyridine, which are described in US Pat. prior art cited above (JAm.Chem.Soc, 1950, 376-381).

The compounds of formula (I) according to the invention are easily accessible from the point of view of synthesis: they can be obtained in a single step from 2-amino-4-chloro-6-methyl-pyrimidine or 2- amino-4-methoxy-6-methylpyrimidine which are commercial products and a base, especially a primary or secondary amine.

The formation of the compounds of formula (I) results from the aromatic nucleophilic substitution of a chlorine or a methoxy, resulting from 2-amino-4-chloro-6-methyl-pyrimidine or 2-amino-4- methoxy-6-methyl-pyrimidine, by a primary or secondary amine. This type of reaction is amply documented.

Reference may be made to one of the following documents:

Quintela et al., Monatsh Chem 1996, 127 (6), 739-745;

- Abdel-Fattah et al. ; J Chem Res, Synop 1994 (11), 412-413; HuII et al .; J Chem Soc 1946, 357;

Curd et al; J Chem Soc 1946, p 343 and p 362.

Advantageously, the process for preparing the compounds of formula (I) is characterized in that it essentially consists of the following steps: (i) dissolving a primary or secondary amine in a po¬ lar organic solvent, preferably chosen from ethanol, methanol, THF, dioxane and N-methyl-pyrrolidone;

(ii) adding an organic or inorganic base, preferably selected from potassium carbonate (K ₂ CO ₃ ), sodium carbonate (Na ₂ CO ₃ ), calcium carbonate (CaCO ₃ ), sodium hydroxide, diisopropylethylamine, preferably diisopropylethylamine, in an amount of from 1 to 3 equivalents, preferably from 1 to 2 equivalents, preferably from 1.5 to 1.7 equivalents; (iii) adding 2-amino-4-chloro-6-methyl-pyrimidine or 2-amino-4-methoxy-6-methyl-pyrimidine, preferably 2-amino-4-chloro-6-methyl-pyrimidine in an amount of 0.5 to 1.1 equivalents, preferably 0.7 to 0.9 equivalents;

(iv) leave the medium at ambient temperature or bring it to a temperature of between 20 ^° C. and 85 ^° C., preferably at reflux of the solvent, for a period of duration between 2h and 48h, preferably between 12h and 30h, preferably 20-26 h;

(v) optionally evaporating the reaction medium under vacuum to dryness after returning to ambient temperature; (vi) optionally dissolving the residue in water and extracting the aqueous solution with an organic solvent preferably chosen from ethyl acetate, dichloromethane, diethyl ether, preferably ethyl acetate; (vii) optionally drying and evaporating the organic phase to dryness then optionally purifying the residue, in particular by chromatography on a column of silica gel.

The compounds of formula (I) are, for some of them, new. Among these novel compounds, those for which:

- R1 represents hydrogen; and or

- R2 is a linear or branched hydrocarbon radical, saturated or unsaturated, C1-C20, advantageously C1-C6, preferably substituted with:

(O -NH ₂ , (iv) a 5-, 6-, 7- or 8-membered heterocycle comprising at least one nitrogen heteroatom, said heterocycle, including nitrogen, possibly being substituted by a C1-C6 alkyl chain; C6, advantageously C1-C3;

(v) a 5-, 6-, 7- or 8-membered aromatic heterocycle comprising at least one oxygen heteroatom; (vi) a cycloalkyl comprising 5, 6, 7 or 8 members, which may be substituted by a C 1 -C 6 alkyl chain which may itself be substituted with at least one -NH 2 radical; and or

- R 1 and R ₂ taken together form with the nitrogen atom a first non-aromatic heterocycle of 5, 6, 7 or 8 members which may comprise at least one additional nitrogen hé¬ teroatom, said first heterocycle, including the nitrogen atom, which may be substituted by (a) a C 1 -C 6 alkyl chain which may itself be substituted with at least one radical -NR ¹¹ R '"with R" and R ¹ "representen¬ as, independently the one of the other, a hydrocarbon radical, saturated or unsaturated, linear or branched, C1-C6; and / or (b) a cycloalkyl or a second heterocycle, which may be aromatic, of 5, 6, 7 or 8 members, which com¬ take at least another heteroatom selected from O, said ring or second heterocycle may be substituted by a C1-C6 alkyl chain.

The compounds of formula (I) according to the invention can be employed advantageously in cosmetic or pharmaceutical compositions, especially dermatological compositions, furthermore comprising a physiologically acceptable medium, ie a medium which is compatible with the skin. , its integuments (eyelashes, on- gles, hair), the mucous membranes and / or the scalp, and in particular a cosmetically or pharmaceutically acceptable medium.

The compounds of formula (I) may be present in the cosmetical or pharmaceutical compositions in an amount sufficient to obtain the effect sought, and which may be in particular from 0.001 to 30% by weight, preferably from 0.01 to 15% by weight, and more particularly from 0.1 to 5% by weight, relative to the total weight of the composition.

The compositions comprising said compounds may be in any of the galenic forms suitable for topical application, especially in the form of aqueous, aqueous-organic, organic or oily solution; suspension or dispersion in solvents or fatty substances, of the type lo¬ tion or serum; as a vesicular dispersion; in the form of W / O, O / W or multiple emulsion such as cream or milk; in the form of an ointment, a gel, a solid stick, anhydrous pasty or solid products, a particular aerosol foam or a spray.

The physiologically acceptable medium, its constituents, their quantity, the galenic form of the composition and its method of preparation, may be chosen by those skilled in the art on the basis of their general knowledge according to the type of composition sought.

In particular, the composition may comprise any fatty substance usually used in the intended field of application. Mention may in particular be made of silicone fatty substances such as oils, gums and silicone waxes, as well as non-silicone fatty substances such as oils and waxes of vegetable, mineral, animal and / or synthetic origin. The oils may optionally be volatile or non-volatile. Mention may also be made of hydrocarbons, esters and synthetic ethers, fatty alcohols and fatty acids.

The composition may also comprise an aqueous medium that comprises water; an aqueous-alcoholic medium comprising a monoalcohol, in particular a C1-C6 alcohol such as ethanol or isopropanol, or an organic medium comprising common organic solvents such as C ₁ -C ₆ monoalcohols, in particular ethanol and isopropanol, glycols such as propylene glycol, ketones. The composition may comprise at least one conventional emulsifier chosen from amphoteric, anionic, cationic or nonionic emulsifiers, used alone or as a mixture. It may also comprise the usual adjuvants in the relevant range, such as hydrophilic or lipophilic thickeners or gelling agents, hydrophilic or lipophilic additives, especially cosmetic active agents, antioxidants, perfumes, fillers, pigments, UV filters, odor absorbers, dyes, moisturizers (glycerin), vitamins, acids essential fatty acids, liposoluble polymers especially hydrocarbon-based, opacifiers, stabilizers, sequestering agents, conditioners, propellants.

Of course, those skilled in the art will take care to choose this or these optional additional adjuvants and / or their quantity in such a way that the advantageous properties of the composition according to the invention are not, or substantially not, impaired by the envisaged addition.

Advantageously, the composition according to the invention comprises at least one additional active ingredient. As active agents, mention may be made of the compounds chosen from, alone or as a mixture, the desquamating agents; moisturizing agents; depig¬ menting or propigmenting agents; anti-glycation agents; NO-synthase inhibitors; agents stimulating the synthesis of dermal or epidermal macromolecules and / or preventing their degradation; agents stimulating the proliferation of fibroblasts and / or keratinocytes or stimulating the differentiation of keratinocytes; muscle relaxants; tensors; anti-pollution and / or anti-radical agents; agents acting on microcirculation; agents acting on the energetic metabolism of cells.

Preferably, the composition comprises at least one acid additive and / or an active ingredient with an irritating side effect, preferably chosen from alpha- and beta-hydroxy-carboxylic acids or alpha and beta-keto carboxylic acids, and more particularly alpha-beta-ketocarboxylic acids. and beta-hydroxy acids such as citric acid, malic acid, mandelic acid, tartaric acid, lactic acid, glycolic acid, generally fruit acids, salicylic acid and n-octanoyl-5-salicylic acid and ascorbic acid.

The pH of the compositions according to the invention is preferably between 5 and 9, preferably between 6 and 8.5, advantageously 7.

The compositions comprising the compounds of formula (I) may be presented as follows:

- in the form of a makeup product for the skin of the face, body or lips, such as a foundation, a blush or eyeshadow, a concealer stick, a camouflaging stick, an eye liner, mascara, lipstick, nail polish, nail care;

- in the form of a cosmetic care product for the skin of the face, the body including the scalp, lips, such as a base for care of the lips, a fixing base to be applied to a classic lipstick , a solar composition or artificial tanning; a care composition (day, night, anti-wrinkle, moisturizing, etc.) for the face; a gel or a cream for cleaning or removing make-up;

in the form of a pharmaceutical composition, especially a dermatological composition; in the form of a solid composition such as a soap;

in the form of an aerosol composition comprising in particular a propellant under pressure;

in the form of a hair composition, and in particular a shampoo, a setting lotion, a treatment lotion, a cream or a styling gel, a dyeing composition (in particular of oxidation) optionally in the form of a coloring shampoo, of restructuring lotion for hair, a permanent composition,

in the form of a composition for oral use, for example a toothpaste.

The compounds of formula (I) can be used as basic neutralizing agents.

In a particular embodiment of the invention, the compounds of formula (I) may be employed in a deodorant composition. The compounds of formula (I) according to the invention are preferably present at concentrations ranging from 0.001 to 10% by weight and more particularly from 0.01 to 5%, and even more preferentially from 0.1 to 5% by weight. relative to the total weight of the deodorant composition.

The deodorant compositions in accordance with the invention may further comprise one or more additional deodorant active agents.

The additional deodorant active agents are preferably present at concentrations ranging from 0.001% to 20% by weight and more preferably from 0.1% to 10% by weight relative to the total weight of the composition.

Additional deodorant active agents include antiperspirants which are generally selected from aluminum and / or zirconium salts; complexes of zirconium hydroxychloride and of aluminum hydroxychloride with an amino acid such as those described in patent US-3792068. Such complexes are generally known under the name ZAG (when the amino acid is Glycine) . ZAG complexes usually have a quotient Al / Zr ranging from about 1.67 to 12.5 and a quotient Metal / Cl ranging from about 0.73 to 1.93. Among these products, mention may be made of aluminum zirconium octachlorohydrex GLY, aluminum zirconium pentachlorohydrex GLY, alumi- nium zirconium tetrachlorohydrate GLY and aluminum zirconium trichlorohyrate-GLY.

Among the aluminum salts, mention may be made of aluminum chlorohydrate, aluminum chlorohydrex, aluminum chlorohydrex PEG, aluminum chlorohydrex PG, aluminum dichlorohydrate, aluminum dichlorohydrex PEG, aluminum dichlorohydrex PG, aluminum sesquichlorohydrate, aluminum sesquichlorohydrate PEG, aluminum sesquichlorohydrex PG, alum salts, aluminum sulfate, aluminum zirconium octachlorohydrate, aluminum zirconium penta chlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium trichlorohydrate and more particularly aluminum hydroxychloride marketed by the company REHEIS under the name REACH 301 or by the company GUILINI CHEMIE under the name ALOXICOLL PF 40. the other additional deodorants which may also be mentioned are the water-soluble zinc salts, for example zinc pyrrolidone carboxylate (more commonly known as zinc pidolate), zinc sulphate, zinc chloride, zinc lactate, zinc gluconate.

Bactericides such as 2,4,4'-trichloro-2'-hydroxydiphenyl ether (Triclosan), 3,7,11-trimethyldodeca-2,5,10-trienol (Farnesol) may also be mentioned.

The deodorant cosmetic composition according to the invention is formulated conventionally according to the form of presentation for which it is intended. It may be formulated in a cosmetically acceptable vehicle which may especially be essentially aqueous, or may contain organic solvents and in particular mono-C ₄ alcohols, preferably ethanol to accelerate the evaporation of the product, or propylene. glycol, dipropylene glycol or their ethers. The deodorant cosmetic composition according to the invention may also be formulated in water-in-oil, oil-in-water or triple emulsion, especially water-in-oil-in-water emulsion.

The deodorant cosmetic composition of the invention may also comprise conventional cosmetic adjuvants chosen from fats, gelling agents, emollients, softeners, antioxidants, opacifiers, stabilizers, antifoaming agents, agents and the like. suspending agents, moisturizing agents, vitamins, perfumes, preservatives, surfactants, fillers, sequestering agents, polymers, propellants, alkalizing or acidifying agents, perfumes, dyes, pigments, agents thickeners, or any other ingredient usually used in cosmetics for this type of application.

The fatty substances may consist of an oil or a wax or their mixture, petrolatum, paraffin, lanolin, hydrogenated lanolin, acetylated lanolin; they also include fatty acids, fatty alcohols such as lauryl, cetyl, myristic, stearic, palmitic, oleic alcohol as well as 2-octyldodecanol, fatty acid esters such as glycerol monostearate, polyethylene glycol monostearate. , isopropyl myristate, isopropyl adipate, isopropyl palmitate, octyl palmitate, C1 ₂ -C ₁₅ fatty alcohol benzoates (Finsolv TN of FINETEX), alcohol myristic polyoxypropylenated with 3 moles of propylene oxide (WITCONOL APM WITCO), triglycerides of C- ₆ -C- ₁₈ fatty acids such as caprylic / capric acid triglycerides. The oils are chosen from animal, vegetable, mineral or synthesis and in particular hydrogenated palm oil, hydrogenated castor oil, liquid petrolatum, paraffin oil, purcellin oil (stearyl octanoate), silicone oils and isoparaffins.

The waxes are chosen from animal, fossil, vegetable, mineral or synthetic waxes. These include beeswax, Carnauba wax, Candelilla wax, sugar cane, Japan, ozokerites, Montan wax, microcrystalline waxes, paraffins, waxes and silicate resins. cone.

The thickeners, preferably nonionic, may be selected from guar gums and modified or unmodified celluloses such as hydroxypropyl guar gum, cetylhydroxyethylcellulose, silicas such as for example Bentone Gel MiO sold by the company NL INDUSTRIES or the Veegum Ultra, sold by POLYPLASTIC.

The deodorant cosmetic composition may include emollients, which contribute to a soft, dry, non-sticky feel to the application of the composition to the skin. These emollients can be chosen from volatile silicone type products, non-volatile silicones and other non-volatile emollients. Volatile silicones are defined in a known manner as volatile compounds at room temperature. Among these compounds, mention may be made of cyclic and linear volatile silicones of the dimethylsiloxane type, the chains of which contain from 3 to 9 silicone residues. The cyclomethicines D ₄ or D ₅ are preferably chosen. Nonvolatile silicones are defined in a known manner as low vapor pressure compo¬s at room temperature. Among these compounds are included: polyalkylsiloxanes, in particular linear polyalkylsiloxanes, for example linear polydimethylsiloxanes, or dimethicones, marketed by Dow Corning under the name "Dow Corning 200 Fluid"; polyalkylarylsiloxanes, for example polymethylphenylsiloxanes, marketed by Dow Corning under the name "Dow Corning 556 Fluid"; polyether and siloxane copolymers, for example dimethicone copolyols. The non-volatile emollients useful in the present invention include for example: hydrocarbon-based derivatives, mineral oils, fatty alcohols, alcohol esters of C ₃ -C ₁₈ acids with C ₃ -C _18, esters of benzoic acid with C ₁₂ -C ₁₈ alcohols and mixtures thereof, C ₂ -C ₆ polyols preferably chosen from glycerol, propylene glycol or sorbitol, and polyalkylene glycol polymers.

The propellants may be chosen from dimethyl ether; volatile hydrocarbons such as n-butane, propane, isopropane, isobutane, pentane and isopentane and mixtures thereof; volatile fluorinated hydrocarbons such that 1,1-difluoroethane and 1,1,1-trifluoro-2-fluoroethane. Carbon dioxide, nitrous oxide, nitrogen or compressed air can also be used as the propellant.

The suspending agents may preferably be chosen from hydrophobic modified montmorillonite clays, such as hydrophobic modified bentonites or hectorites. Mention may be made, for example, of the product Stearalkonium Bentonite (CTFA name) (reaction product of bentonite and of quaternary ammonium stearalkonium chloride), such as the commercial product sold under the name Tixogel MP 250 by the company Sud Chemie Rheologicals, United Catalysts Inc. The suspending agents are preferably present in amounts ranging from 0.1 to 5% by weight and more preferably from 0.2 to 2% by weight relative to the total weight of the composition.

Among the fillers that may be used according to the invention, mention may be made of organic powders. As used herein, the term "organic powder" means any solid that is insoluble in the medium at room temperature (25 ° C.). Organic powders that may be used in the composition of the invention include, for example, polyamide particles and especially those sold under the names ORGASOL by Atochem; polyethylene powders; microspheres based on acrylic copolymers, such as those made of ethylene glycol dimethacrylate / lauryl methacrylate copolymer sold by Dow Corning under the name Polytrap; polymethyl methacrylate microspheres, marketed under the name MICROSPHERE M-100 by the company Matsumoto or under the name COVABEAD LH85 by the company Wackherr; ethylene-acrylate copolymer powders, such as those sold under the name FLOBEADS by Sumitomo Seika Chemicals; expanded polymers such as hollow microspheres and in particular microspheres formed of a terpolymer of vinylidene chloride, acrylonitrile and methacrylate and marketed under the name Expancel by the Kemanord Plast Company, or microspheres sold under the name MICROPEARL F 80 ED by the company Matsumoto; powders of natural organic materials such as starch powders, in particular corn starch, wheat or rice, crosslinked or otherwise, such as starch powders cured by octenylsuccinate anhydride, marketed under the name DRY-FLO by the company National Starch; silicone resin microbeads such as those sold under the name Tospearl by the Toshiba Silicone company, in particular Tospearl 240; amino acid powders such as the Lauroyllysine powder marketed under the name Amihope LL-11 by the Ajinomoto Company; the particles of wax mi¬ crodispersion, which preferably have average dimensions infereu¬ res to 1 micron and in particular ranging from 0.02 microns to 1 micron, and which consist es- a wax or a mixture of waxes, such as the products marketed under the name Aquacer by Byk Cera; and their clothes. The amounts of these various constituents that may be present in the deodorant cosmetic composition according to the invention are those conventionally used for the presentation forms considered.

The deodorant composition according to the invention may thus be in the form of a lotion, a cream or a fluid gel dispensed in an aerosol spray, in a pump bottle or in a roll-on, in the form of a gel, a thick cream distributed in a tube and in the form of stick, roll-on or powder, and contain in this respect the ingredients generally used in this type of products and well known to those skilled in the art.

In another embodiment of the invention, the compounds of formula (I) may be employed in a composition for the treatment of imperfection oily skin or acne.

The compounds of formula (I) according to the invention are preferably present at concentrations ranging from 0.001 to 10% by weight and more particularly from 0.01 to 5% by weight, relative to the total weight of the composition.

Preferably, the compound of formula (I) is used in admixture with at least one compound conventionally used in cosmetic or der¬ matological compositions intended for the treatment of oily skin with imperfection or acne. Also, the subject of the invention is also a cosmetic composition suitable for topical application to the skin and comprising, in a physiologically acceptable medium, from 0.001% to 10% by weight of at least one compound of formula (I and from 0.001 to 20% by weight of at least one other compound chosen from desquamating agents, soothing agents, anti-seborrhoeic agents and their mixtures, the% being based on the total weight of the composition.

By desquamating agents is meant active agents capable of acting either directly on desquamation by promoting exfoliation, or on the enzymes involved in the desquamation or degradation of the coméodesmosomes, the glycosidases, the stratum corneum chymotryptic enzym (SCCE) or even other proteases (trypsin, chymotrypsin-like). In particular, mention may be made of α-hydroxy acids such as lactic, glycolic, citric, malic, mandelic and tartaric acids; β-hydroxy acids, in particular salicylic acid and its derivatives (including n-octanoyl-5-salicylic acid); urea; gentisic acid; oligofucoses; cinnamic acid; extracts of Saphora japonica; resveratrol; aminosulfonic compounds and in particular (N-2-hydroxyethylpiperazine-N-2-ethane) sulfonic acid (HEPES); 2-oxothiazolidine-4-carboxylic acid derivatives (procysteine); alpha acid derivatives glycine-type amines (as described in EP852949, as well as sodium methyl glycine diacetate marketed by BASF under the tradename TRILON M); honey; sugar derivatives such as O-octanoyl-6-D-maltose and N-acetyl glucosamine. As soothing agents, there may be mentioned ursolic acid, oleanic acid and their salts and mixtures; extracts of Paeonia suffruticosa, allantoin, extracts of Laminaria saccharina, bisabolol and capryloyl glycine. Anti-seborrhoeic agents include retinoids, and in particular retinol and its esters, zinc salts, and pyridoxine.

In another embodiment of the invention, the compounds of formula (I) may be employed in a composition for the treatment of pellicles. The compounds of formula (I) according to the invention are present therein preferably in a proportion of from 0.001 to 10% by weight, preferably from 0.01 to 5% by weight, relative to the total weight of the composition.

The compound of formula (I) may be combined with additional compounds that favor the regrowth and / or limit the fall of keratin fibers (hair, eyelashes). Also, the subject of the invention is also a cosmetic composition suitable for topical application to the scalp, and comprising, in a physiologically acceptable medium, from 0.001% to 10% by weight of at least one compound of formula (I). ) and from 0.001% to 20% by weight of at least one other compound chosen from the additional compounds promoting regrowth and / or limiting the drop in keratinous fibers, in particular as mentioned below, the% being relative to the total weight of the composition.

These additional compounds may in particular be chosen from the lipoxygenase inhibitors as described in EP 648488, the inhibitors of BKK described in EP 845700, the prostaglandins and derivatives thereof, in particular those described in WO 98/33497, WO 95/11003, JP 97-100091, JP 96-134242, agonists or antagonists of prostaglandin receptors, non-prostanoid prostaglandin analogs as described in EP 1175891 and EP1175890, WO 01/74307, WO 01/74313, WO 01/74314, WO 01/74315 or WO 01/72268, their mixtures. As other additional active compounds that promote the growth of keratinic fibers and / or limit their fall (in particular the hair or the eyelashes) that may be present in the composition according to the invention, mention may be made of vasodilators, antiandrogens and cyclosporins. and their analogues, antimicrobials and antifungals, anti-inflammatories, retinoids, alone or in a mixture.

The vasodilators that can be used include potassium channel agonists including minoxidil and the compounds described in the patents. US 3,382,247; 756092; 772990; 760043; 466694; 438058; 973474; cromakalim, nicorandil and diaxozide, alone or in combination. Useful antiandrogens include, but are not limited to, steroidal or nonsteroidal 5α-reductase inhibitors, such as finasteride and the compounds described in US 5,516,779, cyprosterone acetate, azelaic acid, its salts and derivatives, and compounds described in US 5,480,913, flutamide, oxendolone, spironolactone, diethylstilbestrol and the compounds described in US Pat. Nos. 4,411,981, 5,565,467 and 4,910,226. The antimicrobial or antifungal compounds may be chosen from the following: selenium, including selenium disulfide, octopirox, triclocaran, triclosan, pyrithione zinc, itraconazole, asiatic acid, hinokitiol, mipirocine, tetracyclines, especially erythromycin and the compounds described in EP 0680745, clinycin hydrochloride, benzoyl or benzyl peroxide, minocycline and compounds belonging to the imidazoles class such as peconazole, ketocona zole or miconazole or their salts, nicotinic acid esters, including in particular tocopherol nicotinate, benzyl nicotinate and C1-C6 alkyl nicotinates such as methyl or hexyl nicotine. The anti-inflammatory drugs may be selected from steroidal anti-inflammatory agents such as glucocorticoids, corticosteroids (for example: hydrocortisone) and nonsteroidal anti-inflammatory drugs such as glycyrrhetinic acid and α-anti-inflammatory drugs. bisabolol, benzydamine, salicylic acid and the compounds described in EP 0770399, WO 94/06434 and FR 2 268523. The retinoids may be chosen from isotretinoin, acitretin, tazarotene, retinal and the like. adapalene.

As other additional active compounds for promoting the growth and / or limiting the fall of keratinous fibers such as hair and eyelashes, used in combination with the compound of formula (I), mention may be made of aminexil, 6-0 [(9Z, 12Z) -octadeca-9,12-dienoyl] hexapyranose, benzalkonium chloride, benzethonium chloride, phenol, oestradiol, chlorpheniramine maleate, chlorophyllin derivatives, cholesterol, cysteine, methionine, menthol, peppermint oil, calcium panthotenate, panthenol, resorcinol, protein kinase C activators, glycosidase inhibitors, glycosaminoglycanase inhibitors, esters of pyroglutamic acid, hexosaccharide or acyl hexosaccharic acids, substituted aryl ethenes, N-acyl amino acids, flavonoids, ascomycin derivatives and analogues, histamine antagonists, saponins, inhibitors of proteogly canase, estrogen agonists and antagonists, pseudotrienes, cytokines and promoters of growth factors, inhibitors of IL-1 or IL-6, IL-10 promoters, inhibitors of TNF, benzophenones and hydantoin, retinoic acid; vitamins such as vitamin D, vitamin B12 analogues, panthotenol; triterpenes such as ursolic acid and the compounds described in US 5529769, US 5468888, US 5631282 ; antipruritic agents such as thenaldine, trimeprazine or cypropeptadine; antiparasitics, particularly metronidazole, crotamiton or pyrethroids; calcium antagonists, such as cinnarizine, diltiazem, nimodipine, verapamil, alverine and nifedipine; hormones such as estriol or its analogues, thyroxine and its salts, progesterone; agonists of the FP receptor (F-type prostaglandin receptor) such as latanoprost, (5E) -7 - {(1R, 2R, 3R, 5S) -3,5-dihydroxy-2 - [(3R)) 3-hydroxy-5-phenylpentyl] cyclopentyl} hept-5-enoic, bimatoprost, travoprost, unoprostone and butaprost; their mixtures. Advantageously, the composition according to the invention comprises at least one inhibitor of 15-PGDH as defined above and at least one prostaglandin or a prostaglandin derivative such as, for example, prostaglandins of series 2, in particular PGF2-α and PGE 2 in saline or ester form (eg isopropyl esters), their derivatives such as 16,16 dimethyl PGE 2, 17 phenyl PGE 2, 16,16 dimethyl PGF 2 -α, 17 phenyl PGF 2 -α prostaglandins of the series 1, such as deoxyprostatin E1, deoxypropyline E1 in salt or ester form, and their analogues, in particular lata¬ noprost, (5E) -7 - {(1 R, 2R, 3R, 5S) acid) 1,3,5-dihydroxy-2 - [(3R) -3-hydroxy-5-phenylpentyl] cyclopentyl} hept-5-enoic acid, viprostol, bimatoprost, clo-prostenol travoprost, fluprostenol, cloprostenol, butaprost, unopros¬ tone, misoprostol, their salts or their esters.

The compositions according to the invention can be in different forms. Among these, there may be mentioned shampoos, compositions to be applied before or after shampooing, these being in the form of a lotion more or less thickened, a gel or an emulsion. The compositions according to the invention, especially in the form of shampoo, also contain at least one anionic, nonionic, zwitterionic, amphoteric or cationic surfactant. The proportion of surfactant is generally between 0.01% and 50% by weight, but preferably between 0.05% and 30% by weight relative to the total weight of the composition. When a surfactant of the nonionic type is used, it is generally used in a proportion of between 0.1 and 40% by weight, and preferably between 1% and 20% by weight relative to to the total weight of the composition. Surfactants of the cationic type, because of their low de¬ tergent power, are more particularly used in the compositions according to the invention in the form of care compositions before or after shampooing. Among the anionic surfactants that can be used, alone or in mixtures, according to the present invention, mention may be made especially of alkaline salts, in particular sodium salts, ammonium salts, amine salts, aminoalcohol salts or magnesium salts. , the following compounds: alkyl sulphates, alkyl ether sulphates, alkylamido ether sulphates, sulphate monoglycerides, alkyl glyceryl sulphonates, alkyl sulphonates, alkyl phosphates, sulphonyl alkylamines, alkylarylsulfonates, α-olefinsulfonates, paraffinsulfonates, alkylsulfosuccinates, alkylethersulfosuccinates, alkylamidesulfosuccinates, alkylsulfosuccinamates, alkylsulfoacetates, alkyletherphosphates, acylisethionates, N-acyltaurates, N-acylaminoacids, such as N-acylsarcosinates, N-acylglutamates. It is also possible to use salts of fatty acids such as those of undecenylic, oleic, ricinoleic, palmitic and stearic acids, of coconut oil acid or of hydrogenated coconut oil; acylhydroxyacids such as acyl lactylates. It is also possible to use weakly anionic surfactants, such as alkyl-D-galactoside uronic acids and their salts, as well as polyoxyalkylenated carboxylic ether acids or their salts. The alkyl or acyl radical of the various tensio¬ enoactive agents listed above preferably has from 8 to 22 carbon atoms. Among the nonionic surfactants, mention may be made of alcohols, alpha-diols, alkylphenols or polyethoxylated, polypropoxylated or polyglycerolated fatty acids, having a fatty chain comprising from 8 to 22 carbon atoms, the number of groups ethylene oxide or propylene oxide ranging from 2 to 50 and that of glycerol in particular from 2 to 30. Mention may also be made of copolymers of ethylene oxide and propylene oxide, amines or polyethoxylated fatty amides having preferably from 2 to 30 moles of ethylene oxide, the fats of the polyglycerolated fats having on average 1 to 5 glycerol groups, the polyglycerolated diglycolamides, the fatty acid esters of optionally sorbitan oxyethylenated, the acid esters Sucrose fatty acids, optionally oxyalkylenated alkylpolyglycosides, alkylglucoside esters, N-alkylglucamine derivatives and amine oxides.

Among the amphoteric or zwitterionic surfactants, mention may be made of aliphatic secondary or tertiary amine derivatives, in which the aliphatic radical is a linear or branched chain containing 8 to 22 carbon atoms and containing at least one water-soluble anionic group (for example: carboxyl, boxylate, sulphonate, sulphate, phosphate or phosphonate), such as for example alkylbetaines, alkylaminocarboxylates, sulphobetaines, alkylamidoalkylbetaines, alkylamidoalkylsulphobetaines, imidazolium derivatives, especially those of amphocarboxyglycinate or amphocarboxypropionate. Among the cationic surfactants, mention may in particular be made of optionally polyoxyalkylenated and / or quaternized fatty amine salts, fatty acid esters of optionally polyoxyalkylenated and / or quaternized amino alcohols, quaternary ammonium salts such as chlorides or bromides of tetraalkylammonium, alkylamidoalkyl trialkylammonium, trialkylbenzylammonium, trialkylhydroxyalkylammonium, dialkylamidoalkyldimethylammonium, alkylpyridinium and imidazolium derivatives. The aqueous vehicle of the compositions according to the invention is either water or a mixture of water and a cosmetically acceptable solvent such as ethanol, glycol or a glycol ether.

The compositions according to the invention may also comprise at least one cosmetically or dermatologically acceptable additive chosen from a conditioning agent, a thickening agent, a polymer of cationic, anionic, nonionic or amphoteric type, a sunscreen, a ceramide, a hyaluronic acid, hydroxyacid, a preservative, an antimicrobial agent, an additional anti-dandruff agent, a pearlescent agent, a coloring agent, a perfume, an electrolyte or a suspending agent.

As conditioning agent that can be used in the compositions according to the invention, there may be mentioned in particular hydrogenated or non-hydrogenated natural oils, synthetic hydrocarbon, cyclic or aliphatic, linear or branched, saturated or unsaturated synthetic oils, such as, for example, polyolefins, in particular especially polydecenes and polyisobutenes, volatile or nonvolatile silicone oils, organomodified or not, soluble or not, fluorinated or perfluorinated oils, fatty esters, esters of polyhydric alcohols and glycerides. It is also possible to use as conditioning agent in the compositions se¬ lon the invention, synthetic or natural waxes, silicone gums and resins, protein or protein hydrolysates quaternized or otherwise or a mixture of these various agents.

The present invention also relates to a cosmetic treatment method comprising the application on the hair of a sufficient amount of a composition as defined above.

In general, the composition is applied 1 to 3 times a week for 6 to 8 weeks. When the composition according to the invention is applied in the form of a lotion or a cream before or after shampooing, it is optionally left on the hair for about 30 seconds to 5 minutes, and then rinsed off if necessary. the water.

The following examples illustrate the invention in more detail without limiting in any way the scope.

Example 1

Synthesis of 4- (2-Amino-6-methyl-pyrimidin-4-ylamino) -butyl-dimethyl-silanol

In a monocolumn flask, 4-aminobutyl dimethylmethoxysilane (4.45 g, 27.6 mmol), 2-amino-4-chloro-6-methylpyrimidine (3.30 g, 23 mmol) and diisopropylethylamine (8 ml, 46 mmol) are introduced. ) in 150 ml of ethanol. The medium is heated at reflux for 24 hours, then cooled and the solvent is evaporated. The oil obtained is purified by chromatography on silica gel, eluting with 9/1 (v / v) dichloromethane / methanol. NMR ^(1H, 400MHz, δ ppm, DMSO-d _6): 6.69 (s, 1H); 5.84 (s, 2H); 5.59 (s, 1H); 3.16 (d, 2H); 2.00 (s, 3H); 1.49 (tt, 2H); 1.34 (tt, 2H); 0.48 (m, 2H); 0.01 (s, 6H) MS (ES +): 255 (M + H ⁺ ) 100%

Example 2

The compounds of formula (I) according to the invention can also be synthesized according to the following general procedure: In a tube, 2-amino-4-chloro-6-methylpyrimidine (28.7 mg, 0.2 mmol) is introduced. ), diisopropylethylamine (70 μl, 0.4 mmol) and the amine correspon¬ dant (0.24 mmol). The medium is refluxed for 24 hours. The reaction medium is concentrated and then purified by chromatography on a column of silica gel. The products are detected in electrospray ion mass spectrometry.

4-N-hexyl-6-methyl-pyrimidine-2,4-diamine was synthesized according to this general procedure.

Structure:

NMR ^(1H, 400MHz, δ ppm, DMSO-d _6): 7.74 (s, 1H); 6.71 (s, 2H); 5.74 (s, 1H); 2.08 (s, 3H); 1.47 (m, 3H); 1.26 (m, 7H); 0.86 (m, 3H).

Example 3

Determination of the ionization constants of the compounds of formula (I)

Material and method: The ionization constants are determined experimentally by potentiometric titration according to the operating conditions described below and evaluated by the prediction software ACD / pK DB, Version 5.12. By default, the software uses an internal database to calculate the pKa value of an ionizable function. The accuracy of the result is greater by using a database that contains substructures with an experimentally determined pKa value.

A base containing the following 2 molecules is used (experimental pKa in water, 0.15M NaCl): 4-aminopyrimidine: pKa = 6.00 2-aminopyridine: pKa = 3.90

Operating conditions of the potentiometric titration

- Equipment used: (Radiometer-Tacussel): TIM 900 titrator SAC 90 Autosampler software Tim TaIk 9

- Test sample: 10 ^"4 mole

- Dissolving: (solubilization with autosampler)

5 ml of the DMSO 70 / Ethanol 10 / water mixture (stirring for 3 minutes with nitrogen sparge)

10 ml of a solution of 0.225M NaCl in water 80 / DMSO (stirring for 3 minutes with sparging with nitrogen)

- Titration method:

Calibration of the electrode between pH4 and pH10

Direct titration with 1 N NaOH or after addition of 1 N HCl

Inflection detection with continuous addition of titrant minimum addition speed: 1% / min max. Addition rate: 1% / min

Nitrogen flux at the surface of the solution during titration

- Calculations:

2 polynomial functions are used to obtain the pKa in water in 0.15M NaCl medium: for the acid functions: pKaH20 = -0.0208 (pKa _SO ) ² + 1, 257pKa _SO ι _V ant - 1, 6 for the basic functions: pKaH2o = -0.0208 (pKa _S oive) ² + 1, 257pKa _NA ivant - 0.75

Results

The structure of the molecules and the pKa values obtained experimentally and by prediction are presented in the tables above. The value of the pKa of the NH ⁺ / N function of the pyrimidine unit is indicated in bold.

The compounds according to the invention have a basic function on the pyrimidine unit whose pKa value is greater than or equal to 7.5, which makes them compatible as basic neutralizing agents.

Example 4: Gel for the face

- Glyceryl polyacrylate (Norgel) 30%

- Polyacrylamide / C13-14 lsoparaffin / laureth-7 (Sepigel 305) 2%

- Silicone oil 10%

compound of Example 2 5% - Water qs 100%

Example 5: lotion

- compound of example 3c 0.2%

- glycerin 2%

- ethyl alcohol 20%

- oxyethylenated butanol (26OE) oxypropylene (26OP), hydrogenated castor oil oxyethylenated (40 EO) in water 1%

- demineralized water qs 100%

Example 6: Treatment gel for acne skin

- compound of example 3g 1%

- xanthan gum 1%

- glycerin 2%

- ethanol. 20%

- oxyethylenated butyl alcohol (26OE) oxypropylene mixture (26OP), hydrogenated castor oil oxyethylenated (40OE) in water 1%

- perfume qs

- demineralized water qs 100% This gel is suitable for the treatment of oily skin, applied once or twice a day on the face.

Example 7 Foaming Cleansing Cream

- Ethylene glycol monostearate 2%

- compound of example 3c 0.5%

- magnesium aluminum silicate hydrate 1, 7%

- hydroxypropyl methylcellulose 0,8% - mixture of sodium cocoyl isethionate and coconut fatty acids (Elfan AT 84 G from Akzo) 15%

- stearic acid 1, 25%

- lauroyl sodium sarcosinate at 30% in water 10%

- perfume qs - demineralised water qs 100%

Example 8: Care Cream

sorbitan tristearate 1% - compound of Example 3g 1, 5%

cross-linked carboxyvinyl homopolymer 0.4%

- 0.5% xanthan gum

- ethylene glycol dimethacrylate / lauria methacrylate copolymer

- cyclopentadimethylsiloxane 6% - glycerin 3%

- emulsifying 4%

- perfume qs

- demineralized water qs 100%

Example 9: Camouflaging Stick for Oily Skin

- waxes (Camauba and Ozokerite) 14%

- liquid fraction of shea butter 4%

- oxides of titanium and zinc 22% - iron oxides 4%

- composed of example 3c 1%

- polydimethylsiloxane / 0.1% hydrated silica

- cetyl alcohol 1, 4% - isoparaffin qs 100% The stick obtained can be applied to the face several times a day.

Example 10: Tinted Cream - hydrogenated lecithin 2.4%

- apricot almond oil 6%

- ethylene glycol dimethacrylate copolymer / Iauryl methacrylate 1%

oxyethylenated soy sterols (5 EO) 1, 6% - compound of Example 2 1%

- iron oxides 0.9%

- 5% titanium oxide

polyacrylamide / Ci ₃ -Ci ₄ -lsoparaffin / Laureth-7 (Sepigel 305) 4%

- cyclopentadimethylsiloxane 6% - glycerin 6%

- propylene glycol 6%

- perfume qs

- demineralized water qs 100%

Example 11: Face cream (oil-in-water emulsion)

Compound of example 1 0.15%

Glycerol Stearate 2.00%

Polysorbate 60 (Tween 60 sold by the company ICI) 1, 00% stearic acid 1, 40%

N-octanoyl-5-salicylic acid 0.50%

Triethanolamine 0.70%

Carbomer 0.40%

Liquid fraction of shea butter 12.00% Perhydrosqualene 12.00%

0.05% antioxidant

Perfume 0.5% Water qs 100%

Example 12 Foaming Cleansing Cream

- Ethylene glycol monostearate 2%

- Composed of example 3b 0.5%

- magnesium aluminum silicate hydrate 1, 7% - hydroxypropyl methylcellulose 0,8%

- mixture of sodium cocoyl isethionate and coconut fatty acids (Elfan AT 84 G from Akzo) 15%

- stearic acid 1, 25%

- lauroyl sodium sarcosinate at 30% in water 10% - perfume qs

- demineralized water qs 100% The cream thus obtained is suitable for cleaning the acne skin, for example by use on the face twice a day.

Example 13 Anti-Dandruff Shampoo

- Compound of Example 1 0.35 g

- Sodium and magnesium lauryl ether sulphate (80/20) oxyethylenated with 4 moles of ethylene oxide

(Albright & Wilson BSD Empicol) 10 g MA - cocoylamidopropylbetaine / glycerol monolaurate (Goldschmidt-tegobetaine-HS) mixture in aqueous solution at 30% MA (active ingredient) 5 g MA

- Polydimethylsiloxane (MW 250,000)

(Silbione oil 70047 V 500.000 from Rhône Poulenc) 2 g - Mixture of cetyl ether and 2-hydroxy cetylstearyl / cetyl alcohol (60/40) 2.5 g

- Mono-isopropanolamide of coconut acid 1, 5 g

(C10-C30) alkyl acrylate-crosslinked acrylic acid copolymer (Goodrich Carbopol 1382) 0.5 g - NaOH q.s. pH 4

- Water q.s. p. 100 g

After moistening the hair, apply a sufficient amount of shampoo then lather and let pause about 2 min. The hair is then thoroughly rinsed.

EXAMPLE 14 Anti-Dandruff Shampoo

- Compound of Example 2 1 g

- Dodecanediol polyglycerolated with 3.5 moles of glycerol 20 g MA - Perhydrosqualene 2 g

- xanthan gum 1 g

- Preservative, perfume q.s.

- Hydrochloric acid q.s. pH 4

- Water q.s. p. 100 g

Example 15 Anti-dandruff composition after shampooing

- Compound of example 3c 1 g

Polyacrylamide (Sepigel 305 from Seppic) 3 g MA - Cyclomethicone (and) dimethiconol (Dow Corning 1401)

Dow Corning Substantivity Aid Fluid) 20 g

- Hydrochloric acid qs pH 4 - Water qs 100 g After having thoroughly rinsed the hair previously shampooed, a sufficient amount of composition is applied to the whole of the hair. Let it pause for about 2 to 5 minutes and rinse evenly.

Examples 16 and 17: Deodorant gels

Claims

1. A cosmetic, dermatological or pharmaceutical composition comprising, in a physiologically acceptable medium, at least one compound of the 6-methyl-2,4-diaminopyrimidine form of formula (I):

in which R 1 and R ₂ , which are identical or different, represent: a hydrogen atom, it being understood that R 1 and R 2 do not simul¬ simultaneously represent a hydrogen atom,

(i) a radical -NH ₂ , -CN, -CF ₃ , -OZ or -COOZ with Z representing a hydrogen atom or a linear or branched, saturated or unsaturated C1-C4 alkyl radical, advantageously a methyl radical, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl; (ii) an -NRR ¹ radical with R and R ', which may be identical or different, represents a linear or branched, saturated or unsaturated C ¹ -C ⁸ alkyl radical, advantageously C ¹ -C ³ ; R and R 'taken together may form with the nitrogen atom a hetero ring, which may be aromatic, of 5, 6, 7 or 8 members may include at least one additional heteroatom selected from O, N and / or S said heterocycle, including the nitrogen atom, may be substituted by a C1-C6 alkyl chain, said alkyl chain being itself substituted by at least one -NR ¹¹ R ¹ "radical with R" and R '"independently of one another is a linear or branched C 1-6 hydrogen or hydrocarbon radical, saturated or unsaturated, (iii) a radical -Si (CH ₃ ) ₂ - OH; -Si (CH ₃ ) ₂ -OEt; -Si (CH ₃ ) ₂ -O-CH ₂ -Phenyl, - Si (CH ₂ ) ₂ -OMe or -Si (JPr) ₂ -OEt;

(iv) a 5-, 6-, 7- or 8-membered heterocycle comprising at least one heteroatom selected from O, N and / or S, said heterocycle, including nitrogen when present, which may be substituted by a chain C1-C6 alkyl, preferably C1-C3 alkyl;

(v) a 5-, 6-, 7- or 8-membered aromatic heterocycle comprising at least one heteroatom selected from O, N and / or S, said heterocycle possibly being substituted with a C1-C6 alkyl chain; preferably methyl, ethyl or propyl; (vi) a cycloalkyl comprising 5, 6, 7 or 8 members, which may be substituted by a C 1 -C 6 alkyl chain which may itself be substituted with at least one radical -NR ¹¹ R '"with R" and R " ¹ represents, independently of one another, a linear or branched, saturated or unsaturated C 1 -C 6 hydrogen or hydrocarbon radical, and / or a cycloalkyl comprising 5, 6, 7 or 8 members;

- R 1 and R ₂ taken together capable of forming with the nitrogen atom a first non-aromatic heterocycle of 5, 6, 7 or 8 members which may comprise at least one additional heteroatom selected from O, N and / or S, said first heterocycle, including the nitrogen atom, which may be substituted by (a) a C 1 -C 6 alkyl chain which may itself be substituted by at least one -NR ¹¹ R ¹ "radical with R" and R " ¹ independently of one another, a linear or branched, saturated or unsaturated C 1 -C 6 hydrocarbon or hydrocarbon radical, and / or (b) a cycloalkyl or a second heterocycle, which may be aromatic, of 5, 6, 7 or 8 members, which may comprise at least one other heteroatom selected from O, N and / or S, said ring or second heterocycle may be substituted by an alkyl chain in C1 -C6, as well as their salts.

2. Composition according to claim 1, wherein R2 is a linear or branched, saturated or unsaturated C 1 -C 20, advantageously C 1 -C 6, hydrocarbon radical which may be substituted by

O) -NH ₂ , (iv) a 5-, 6-, 7- or 8-membered heterocycle comprising at least one heteroatom of nitrogen, said heterocycle, including nitrogen, possibly being substituted by a C1-C6 alkyl chain; C6, advantageously C1-C3;

(v) a 5-, 6-, 7- or 8-membered aromatic heterocycle comprising at least one oxygen heteroatom; (vi) a cycloalkyl comprising 5, 6, 7 or 8 members, which may be substituted by a C 1 -C 6 alkyl chain which may itself be substituted with at least one -NH 2 radical.

3. Composition according to one of the preceding claims, wherein R1 represents hydrogen.

4. Composition according to claim 1, in which R 1 and R ₂ taken together form, with the nitrogen atom, a first non-aromatic heterocycle of 5, 6, 7 or 8 members which may comprise at least one additional heteroatom of nitrogen, said heterocycle, including the nitrogen atom, which can be substituted with (a) a C1-C6 alkyl chain which can itself be substituted by at least one radical -NR ¹¹ R ¹ "with R" and R "representing, independently of one another, a hydrocarbon radical, saturated or unsaturated, linear or branched, in C1-C6 alkyl; and / or (b) a cycloalkyl or a second aromatic heterocyclic ring of 5, 6, 7 or 8 members, which may comprise at least one other heteroatom selected from O, said ring or second heterocycle being substituted by a C1-C6 alkyl chain.

5. Composition according to one of the preceding claims, in which the salts are chosen from the salts of mineral acid or of organic acid, in particular of mineral acid chosen from hydrochloric, sulfuric, nitric and phosphoric acids, or organic acid selected from carbonic acid, acetic acid, succinic acid, fumaric acid, lactic acid, glycolic acid, citric acid, gluconic acid, salicylic acid and tartaric acid.

6. Composition according to one of the preceding claims, wherein the compound is selected from: - 4-N- [4- (methoxydimethylsilyl) butyl] -6-methyl-pyrimidine-2,4-diamine;

4-N- (4- (n-butyldimethylsilanol)) 6-methylpyrimidine-2,4-diamine;

4-N - [- [3- (ethoxydimethylsilyl) propyl] -6-methyl-pyrimidine-2,4-diamine;

4-N - [- [3- (ethoxydiisopropylsilyl) propyl] -6-methyl-pyrimidine-2,4-diamine;

4-N- [4-piperidinylmethyl] -6-methyl-pyrimidine-2,4-diamine; 4-N - [(2S) -2-pyrrolidinylmethyl] -6-methyl-pyrimidine-2,4-diamine;

4-N - [- [1-ethylpyrrolidinyl-2-ylmethyl] -6-methyl-pyrimidine-2,4-diamine;

4-methyl-6- [4- (3-pyrrolidin-1-yl-propyl) - [1,4] diazepan-1-yl] -pyrimidin-2-ylamine

4-Methyl-6- (4-methyl- [1,4] diazepan-1-yl) -pyrimidin-2-ylamine

2- [4- (2-Amino-6-methyl-pyrimidin-4-yl) - [1,4] diazepan-1-yl] -ethanol; 4- (4-Butyl- [1,4] diazepan-1-yl) -6-methyl-pyrimidin-2-ylamine;

4-Methyl-6- (4-phenethyl- [1,4] diazepan-1-yl) -pyrimidin-2-ylamine;

4- {4- [2- (4-Fluoro-phenyl) -ethyl] - [1,4] diazepan-1-yl} -6-methyl-pyrimidin-2-ylamine

4-Methyl-6- [4- (3-trifluoromethyl-pyridin-2-yl) - [1,4] diazepan-1-yl] -pyrimidin-2-ylamine

4- [4- (2-dimethylaminoethyl) pipiperazin-1-yl] -6-methyl-pyrimidin-2-ylamine;

4-Methyl-6- (4-methyl-piperazin-1-yl) -pyrimidin-2-ylamine;

2- [4- (2-Amino-6-methyl-pyrimidin-4-yl) -piperazin-1-yl] ethanol;

3- [4- (2-Amino-6-methyl-pyrimidin-4-yl) -piperazin-1-yl] -propionitrile; 4- [4- (2-Methoxy-ethyl) -piperazin-1-yl] -6-methyl-pyrimidin-2-ylamine;

4- (4-Cyclopentyl-piperazin-1-yl) -6-methyl-pyrimidin-2-ylamine;

4- [4- (3-Methoxy-propyl) -piperazin-1-yl] -6-methyl-pyrimidin-2-ylamine;

4-Methyl-6- (4-phenyl-piperazin-1-yl) -pyrimidin-2-ylamine;

4-Methyl-6- (4-pyridin-2-yl-piperazin-1-yl) -pyrimidin-2-ylamine; 4-Methyl-6- (4-pyrimidin-2-yl-piperazin-1-yl) -pyrimidin-2-ylamine;

4-Methyl-6- (2,3,5,6-tetrahydro- [1,2 '] bipyrazinyl-4-yl) -pyrimidin-2-ylamine;

4- (4-Cyclohexyl-piperazin-1-yl) -6-methyl-pyrimidin-2-ylamine;

4- (4-Hexyl-piperazin-1-yl) -6-methyl-pyrimidin-2-ylamine; 4-N - [- (2-amino-2-methyl-propyl) -6-methyl-pyrimidine-2,4-cliamine; 4-N - [- (2-piperazin-1-yl-ethyl) -6-methyl-pyrimidine-2,4-diamino; 4-N - [- (5-methyl-furan-2-ylmethyl) -6-methyl-pyrimidine-2,4-diamine;

4-N - [(Furan-2-ylmethyl) -6-methyl-pyrimidine-2,4-diamine; 4-Methyl-6- [4- (1-methyl-piperidin-4-yl) -piperazin-1-yl] -pyrimidin-2-ylamine;

4-Methyl-6- (4-imidazol-2-yl-piperazin-1-yl) -pyrimidin-2-ylamine; 4-N - [- (3-aminomethylcyclohexylmethyl) -6-methylpyrimidine-2,4-diamine; 4-Methyl-6-piperidin-1-yl-pirimidin-2-ylamine;

4-Methyl-6-pyrrolidin-1-yl-pyrimidin-2-ylamine; 1- (2-Amino-6-methyl-pyrimidin-4-yl) -pyrrolidin-3-ol;

- [1- (2-Amino-6-methyl-pyrimidin-4-yl) -pyrrolidin-3-yl] -methanol;

4-Methyl-6- (2-methyl-pyrrolidin-1-yl) -pyrimidin-2-ylamine;

4- (2-Isopropyl-pyrrolidin-1-yl) -6-methyl-pyrimidin-2-ylamine;

1- (2-Amino-6-methyl-pyrimidin-4-yl) -pyrrolidine-2-carbonitrile; 4-Methyl-6- (3-phenyl-pyrrolidin-1-yl) -pyrimidin-2-ylamine;

4-Methyl-6- (3-pyridin-3-yl-pyrrolidin-1-yl) -pyrimidin-2-ylamine;

4-Methyl-6- (3-pyridin-2-yl-pyrrolidin-1-yl) -pyrimidin-2-ylamine; 4-N-hexyl-6-methyl-pyrimidine-2,4-diamine.

7. Composition according to one of the preceding claims, wherein the compound of formula (I), alone or as a mixture, is present in an amount of 0.001 to 30% by weight, preferably 0.01 to 15% by weight. and more particularly from 0.1 to 5% by weight, relative to the total weight of the composition.

8. Composition according to one of the preceding claims, being in the form of aqueous solution, hydroalcoholic, organic or oily; suspen¬ sion or dispersion in solvents or fats, lotion or serum type; as a vesicular dispersion; in the form of W / O, O / W or multiple emulsion such as cream or milk; in the form of ointment, gel, solid stick, anhydrous pasty or solid products, foam especially aerosol or spray.

9. Composition according to one of the preceding claims, comprising at least one constituent selected from silicone fatty substances such as oils, gums and silicone waxes; oils and waxes of vegetable, mineral, animal and / or synthetic origin; hydrocarbons, esters and synthetic ethers, fatty alcohols and fatty acids; some water; a C1-C6 monoalcohol; glycols such as propylene glycol, ketones; an amphoteric, anionic, cationic or nonionic emulsifier; a hydrophilic or lipophilic thickener or gelling agent; hydrophilic or lipophilic additives, especially cosmetic active agents, antioxidants, perfumes, fillers, pigments, UV filters, odor absorbers, dyes, moisturizers (glycerine), vitamins, fatty acids lipid-soluble polymers, particularly hydrocarbons, opacifiers, stabilizers, sequestering agents, conditioners, propellants.

10. Composition according to one of the preceding claims, comprising at least one additional active agent, in particular chosen from, alone or in mixture: the desquamating agents; moisturizing agents; depigmenting agents or pro¬ pigmenting agents; anti-glycation agents; NO-synthase inhibitors; agents stimulating the synthesis of dermal or epidermal macromolecules and / or preventing their degradation; agents stimulating the proliferation of fibroblasts and / or keratinocytes or stimulating the differentiation of keratinocytes; muscle relaxants; tensors; anti-pollution and / or anti-radical agents; agents acting on microcirculation; agents acting on the energetic metabolism of cells.

11. Composition according to one of the preceding claims, comprising at least one acid additive and / or an irritating side effect active agent, preferably chosen from alpha- and beta-hydroxy-carboxylic acids or alpha and beta-ketocarboxylic acids, and more especially alpha- and beta-hydroxy acids such as citric acid, malic acid, mandelic acid, tartaric acid, lactic acid, glycolic acid, fruit acids, salicylic acid, n-octanoyl-5-salicylic acid and ascorbic acid.

12. Composition according to one of the preceding claims, occurring:

- In the form of a make-up product of the skin of the face, body or lips, such as a foundation, a blush or eyeshadow, a concealer stick, a camouflaging stick, an eye liner, mascara, lipstick, nail polish, nail care;

in the form of an aerosol composition;

in the form of a composition for oral use, for example a toothpaste.

13. Use of at least one compound of formula (I) as defined in one of claims 1 to 6, as basic neutralizing agent.

14. Use of at least one compound of formula (I) as defined in any one of claims 1 to 6, as a deodorant active in a cosmetic composition or in the preparation of a cosmetic composition.

15. Use of at least one compound of formula (I) as defined in any one of claims 1 to 6 for the manufacture of deodorant cosmetics for human topical application.

16. A method for treating human axillary odors, comprising applying to the axillary surface an effective amount of at least one compound of formula (I) as defined in any one of claims 1 to 6.

17. A method for treating human axillary odors, comprising applying to the axillary surface an effective amount of deodorant composition com¬ taking at least one compound of formula (I) as defined in any one of claims 1 to 6 .

18. A deodorant cosmetic composition comprising in a cosmetically acceptable medium at least one compound of formula (I) as defined in any one of claims 1 to 6.

19. Composition according to claim 18, in which the compound or compounds of formula (I) are present in concentrations ranging from 0.001% to 10% by weight, more particularly from 0.01% to 5% by weight, and even more preferentially. from 0.1 to 5% by weight, relative to the total weight of the deodorant composition.

20. Composition according to any one of claims 18 to 19, further comprising at least one additional deodorant active.

21. Composition according to claim 20, in which the additional deodorant active agent (s) are present in concentrations ranging from 0.001% to 20% by weight and preferably from 0.1% to 10% by weight, relative to the total weight of the product. composition.

22. Composition according to any one of Claims 20 to 21, in which the additional deodorant active agent is chosen from antiperspirants, and especially from, alone or as a mixture, the aluminum salts and / or zirconium; complexes of zirconium hydroxychloride and hydroxychloride aluminum with an amino acid; water soluble salts of zinc; the bacteria.

23. A composition according to claim 22, wherein the complexes of zirconium hydroxychloride and of aluminum hydroxychloride are chosen from aluminum zirconium octachlorohydrex GLY, aluminum zirconium pentachlorohydrex GLY, aluminum zirconium tetrachlorohydrate GLY and aluminum zirconium trichlorohydrate-GLY.

24. The composition of claim 22, wherein the aluminum salts and / or zirconium are selected from aluminum chlorohydrate, aluminum chlorohydrex, aluminum chlorohydrex PEG, aluminum chlorohydrex PG, aluminum dichlorohydrate , aluminum dichlorohydrex PEG, aluminum dichlorohydrex PG, aluminum sesquichlorohydrate, aluminum sesquichlorohy- drex PEG, aluminum sesquichlorohydrex PG, alum salts, aluminum sulfate, aluminum zirconium octachlorohydrate, aluminum zirconium pentachlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium trichlorohydrate.

25. Composition according to claim 22, in which the water-soluble zinc salt is chosen from zinc pyrrolidone carboxylate (zinc pidolate), zinc sulphate, zinc chloride, zinc lactate and zinc gluconate. .

26. A composition according to claim 22, wherein the bactericide is selected from 2,4,4'-trichloro-2'-hydroxydiphenyl ether and 3,7,11-trimethyldodecane.

2,5,10-trienol.

27. Composition according to any one of claims 18 to 26, further comprising at least one cosmetic adjuvant selected from water, organic solvents, fatty substances, gelling agents, emollients, softeners, antioxidants, opacifiers, suspending agents, stabilizers, defoamers, moisturizers, vitamins, perfumes, preservatives, surfactants, fillers, sequestering agents, polymers, propellants, basifying or acidifying agents , perfumes, dyes, pigments, thickeners.

28. A process for the cosmetic treatment of cutaneous imperfections of oily skin comprising the topical application to the skin of a composition com¬ taking, in a physiologically acceptable medium, at least one compound of formula (I) as defined in one of the following: any of claims 1 to 6.

29. The process according to claim 28, wherein the composition comprises 0.001 to 10% by weight, especially 0.01 to 5% by weight of compound of formula mule (I), relative to the total weight of the composition.

30. Use of a compound of formula (I) as defined in any one of claims 1 to 6 for the preparation of a composition for the treatment of acne.

31. A cosmetic composition adapted for topical application to the skin and containing, in a physiologically acceptable medium, from 0.001 to 10% by weight of at least one compound of formula (I) as defined in any one of the following: Claims 1 to 6 and from 0.001 to 20% by weight of at least one other compound selected from desquamating agents, soothing agents and anti-seborrhoeic agents, the% being based on the total weight of the composition .

32. Composition according to claim 31, characterized in that said desquamating agent is chosen from α-hydroxy acids such as lactic, glycolic, citric, malic, mandelic and tartaric acids; β-hydroxy acids, in particular salicylic acid and its derivatives (including n-octanoyl-5-salicylic acid); urea; gentisic acid; oligofucoses; cinnamic acid; extracts of Saphora japonica; resveratrol; aminosulfonic compounds and in particular (N-2-hydroxyethylpiperazine-N-2-ethane) sulfonic acid (HEPES); 2-oxothiazolidine-4-carboxylic acid derivatives (procysteine); glycine-type alpha amino acid derivatives, as well as sodium methyl glycine diacetate; honey ; sugar derivatives such as O-octanoyl-6-D-maltose and N-acetyl glucosamine.

33. Composition according to claim 31, characterized in that said anti-seborrhoeic agent is selected from ursolic acid, oleanic acid and their salts and mixtures; extracts of Paeonia suffruticosa, allantoin, extracts of Laminaria sacchahna, bisabolol and capryloyl glycine.

34. Composition according to claim 31, characterized in that said soothing agent is chosen from retinoids, and in particular retinol and its esters, zinc salts, and pyridoxine.

35. A process for the cosmetic treatment of hair films comprising the topical application to the scalp of a composition comprising, in a physiologically acceptable medium, at least one compound of formula (I) as defined in any one of claims 1 to 6.

36. The method of claim 35, wherein the composition comprises 0.001 to 10% by weight, especially 0.01 to 5% by weight of for¬ mule compound (I), relative to the total weight of the composition.

37. Use of a compound of formula (I) as defined in any one of claims 1 to 6 for the preparation of a composition for trai¬ tement capillary films.

38. A cosmetic composition adapted for topical application on cheeched leather and comprising, in a physiologically acceptable medium, from 0.001 to 10% by weight of at least one compound of formula (I) as defined in any one of the following: claims 1 to 6, and from 0.001 to 20% by weight of at least one other compound selected from, the% being based on the total weight of the composition.

39. A composition according to claim 38, characterized in that said com¬ poses promoting regrowth and / or limiting the fall of keratin fibers are selected from lipoxygenase inhibitors; inhibitors of bradykinin; prostaglandins and their derivatives; prostaglandin receptor agonists or antagonists, nonprostanoic prostaglandin analogs; vasodilators and especially potassium channel agonists including minoxidil, cromakalim, nicorandil and diaxozide; antiandrogens and especially steroidal or nonsteroidal 5α-reductase inhibitors, such as finasteride, cyprosterone acetate, azelaic acid, its salts and derivatives, flutamide, oxendolone, spironolactone, diethylstilbestrol; cyclosporins and their analogues, antimicrobials and antifungals, and in particular selenium derivatives, in particular selenium disulphide, octopirox, triclocarban, triclosan, pyrithione zinc, itraconazole, and asiatic acid, hinokitiol, mipirocine, tetracyclines, especially erythromycin, clinycin hydrochloride, benzoyl or benzyl peroxide, minocycline and compounds belonging to the class of imidazoles such as econazole, ketoconazole or miconazole or their salts, nicotinic acid esters, including in particular tocopherol nicotinate, benzyl nicotinate and C1-C6 alkyl nicotinates such as methyl or hexyl nicotinates; anti-inflammatories, and especially steroidal anti-inflammatories such as glucocorticoids, corticosteroids such as hydrocortisone, and nonsteroidal anti-inflammatory drugs such as glycyrrhetinic acid and α-bisabolol, benzydamine, salicylic acid ; retinoids such as isotretinoin, pacretin, tazarotene, retinal and adapalene; aminexil, 6-0 - [(9Z, 12Z) -octadeca-9,12-dienoyl] hexapyranose, benzalkonium chloride, benzethonium chloride, phenol, oestradiol, chlorpheniramine maleate, derivatives thereof chlorophylline, cholesterol, cysteine, methionine, menthol, peppermint oil, calcium panthotenate, panthenol, resorcinol, protein kinase C activators, glycosidase inhibitors, glycosaminoglycanase inhibitors, pyroglutamic acid esters, hexosaccharide or acyl hexosaccharic acids, ethylene aryl N-acyl amino acids, flavonoids, ascomycin derivatives and analogs, histamine antagonists, saponins, proteoglycanase inhibitors, estrogen agonists and antagonists, pseudoterines, cytokines and promoters of growth factors, inhibitors of IL-1 or IL-6, IL-10 promoters, TNF inhibitors, benzophenones and hydantoin, retinoic acid; vitamins such as vitamin D, analogs of vitamin B12, panthotenol; triterpenes such as ursolic acid; antipruritic agents such as thenaldine, trimeprazine or cyprophenpine; antiparasitics, particularly metronidazole, crotamiton or pyrethroids; calcium antagonists, such as cinnariazine, diltiazem, nimodipine, verapamil, palverine and nifedipine; hor¬ mones such as estriol or its analogues, thyroxine and its salts, progesterone; agonists of the FP receptor (F-type prostaglandin receptor) such as latanoprost, (5E) -7 - {(1R, 2R, 3R, 5S) -3,5-dihydroxy-2 - [(3R)) 3-hydroxy-5-phenylpentyl] cyclopentyl} hept-5-enoic, bimatoprost, acroprostone, unoprostone and butaprost; and their mixtures.

40. Composition according to one of claims 38 to 39, further comprising at least one adjuvant chosen from anionic, nonionic, zwitterionic, amphoteric or cationic surfactants; the water; a cosmetically acceptable solvent such as ethanol, glycol or a glycol ether; a conditioning agent, a thickening agent, a polymer of cationic, anionic, nonionic or amphoteric type, a sunscreen, a ceramide, a hydroxy acid, a preserving agent, an antimicrobial agent, an anti-dandruff agent nel, a pearlescent agent, a coloring agent, a perfume, an electrolyte or a suspending agent.

41. Compound of the family of 6-methyl-2,4-diaminopyrimidine of formula (I):

in which R 1 and R ₂ , which are identical or different, represent:

(i) an -NH ₂ , -CN, -CF ₃ , -OZ or -COOZ radical with Z representing a hydrogen atom or a linear or branched, saturated or unsaturated C 1 -C 4 alkyl radical; advantageously a methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl radical;

(ii) a radical -NRR 'with R and R ^{1, which may be} identical or different, represents a linear or branched, saturated or unsaturated C ¹ -C 8 alkyl radical, advantageously C 1 -C 3; R and R ¹ taken together may form with the nitrogen atom a hetero ring, which may be aromatic, of 5, 6, 7 or 8 members may include at least one additional heteroatom selected from O, N and / or S said heterocycle, including the nitrogen atom, may be substituted with a C1-C6 alkyl chain, said alkyl chain being itself substitutable with at least one -NR ¹¹ R " ¹ radical with R" and R '' represent independently of each other a hydrogen atom or a hydrocarbon radical, saturated or unsaturated, linear or branched C1-6;

(iii) a radical -Si (CHa) ₂ -OH; -Si (CH ₃ ) ₂ -OEt; -Si (CH ₃ ) ₂ -O-CH ₂ -Phenyl, - Si (CH ₂ ) ₂ -OMe or -Si (JPr) ₂ -OEt; (iv) a 5-, 6-, 7- or 8-membered heterocycle comprising at least one heteroatom selected from O, N and / or S, said heterocycle, including nitrogen when present, which may be substituted by a chain C1-C6 alkyl, advantageously C1-C3; (v) a 5-, 6-, 7- or 8-membered aromatic heterocycle comprising at least one heteroatom selected from O, N and / or S, said heterocycle possibly being substituted with a C1-C6 alkyl chain; preferably methyl, ethyl or propyl;

(vi) a cycloalkyl comprising 5, 6, 7 or 8 members, which may be substituted by a C 1 -C 6 alkyl chain which may itself be substituted with at least one radical -NR ¹¹ R '"with R" and R'"independently of one another a hydrogen atom or a linear or branched, saturated or unsaturated C 1 -C 6 hydrocarbon-based radical, and / or a cycloalkyl comprising 5, 6, 7 or 8-membered rings;

- R 1 and R ₂ taken together which can form with the nitrogen atom a first non-aromatic heterocycle of 5, 6, 7 or 8 members which may comprise at least one additional heteroatom selected from O, N and / or S, said first heterocycle, including the nitrogen atom, which may be substituted by (a) a C1-C6 alkyl chain which may itself be substituted by at least one -NR "R"'radical with R "and R'"representing, independently of one another, a linear or branched C1-C6 hydrocarbon or saturated or unsaturated hydrocarbon radical; and / or (b) a cycloalkyl or a second heterocycle, which may be aroma¬ tick, of 5, 6, 7 or 8 members, which may comprise at least one other heteroatom chosen from O, N and / or S, said ring or second heterocycle may be substituted with a C1-C6 alkyl chain; as well as their salts. with the exception of 2-amino-4-morpholino-6-methylpyridine and 2-amino-4-piperidino-6-methylpyridine.

42. A compound according to claim 41, in which R2 is a linear or branched, saturated or unsaturated, C 1 -C 20, advantageously C 1 -C 6, hydrocarbon radical, preferably substituted with: (i) -NH ₂ ,

(iv) a 5-, 6-, 7- or 8-membered heterocycle comprising at least one nitrogen heteroatom, said heterocycle, including nitrogen, possibly being substituted with a C1-C6 alkyl chain, advantageously with C1-C6 alkyl, C3; (v) a 5-, 6-, 7- or 8-membered aromatic heterocycle comprising at least one oxygen heteroatom;

43. Compound according to one of claims 41 to 42, wherein R1 represents hydrogen.

44. A compound according to claim 41, in which Ft ₁ and R ₂ taken together with the nitrogen atom form a first non-aromatic heterocycle of 5, 6, 7 or 8 members which may comprise at least one additional heteroatom of nitrogen, said first heterocycle, including the nitrogen atom, may be substituted by (a) a C 1 -C 6 alkyl chain which may itself be substituted by at least one radical -NR ¹¹ R '"with R" and R " ¹ represents, independently of one another, a hydrocarbon radical, saturated or unsaturated, linear or branched, C1-C6; and / or (b) a cycloalkyl or a second heterocycle, which may be aromatic, of 5, 6, 7 or 8 members, which may comprise at least one other heteroatom selected from O, said ring or second heterocycle may be substituted by a C1-C6 alkyl chain.

45. Process for the preparation of the compounds of formula (I) as defined in one of claims 1 to 6, in which, in particular in a single step, 2-amino-4-chloro-6-methyl-is reacted. pyrimidine or 2-amino-4-methoxy-6-methylpyrimidine with a base, especially a primary or secondary amine.

46. Process for the preparation of the compounds of formula (I) as defined in one of claims 1 to 6, characterized in that it essentially consists of the following steps: (i) dissolving a primary or secondary amine in a solvent organic polar, preferably selected from ethanol, methanol, THF, dioxane and N-methyl-pyrrolidone;

(ii) adding an organic or inorganic base, preferably selected from potassium carbonate (K ₂ COa), sodium carbonate (Na ₂ CO ₃ ), carbon calcium nate (CaCOa), caries, diisopropylethylamine, preferably diisopropylethylamine, in an amount of from 1 to 3 equivalents, preferably from 1 to 2 equivalents, preferably from 1.5 to 1.7 equivalents; (iii) adding 2-amino-4-chloro-6-methyl-pyrimidine or 2-amino-4-methoxy-6-methyl-pyrimidine, preferably 2-amino-4-chloro-6-methyl-pyrimidine in an amount of 0.5 to 1.1 equivalents, preferably 0.7 to 0.9 equivalents;

(iv) leaving the medium at ambient temperature or bring it to a temperature of between 20 ^° C. and 85 ^° C., preferably at reflux of the solvent, for a period of between 2 h and 48 h, advantageously between 12 h and 30 h, preferably 20- 26 h;

(v) optionally evaporating the reaction medium under vacuum to dryness after returning to ambient temperature; (vi) optionally dissolving the residue in water and extracting the aqueous solution with an organic solvent preferably selected from ethyl acetate, dichloromethane, diethyl ether, preferably ethyl acetate; (vii) optionally drying and evaporating the organic phase to dryness then optionally purifying the residue, in particular by chromatography on a column of silica gel.