FR2860431A1 - Use of phenylazo benzene, pyridine or pyridazine derivatives as agents for inducing and/or stimulating growth of human keratinic fibers and/or inhibiting their loss and/or increasing their density - Google Patents

Abstract

Use of phenylazo benzene, pyridine or pyridazine derivatives (I) as agents for inducing and/or stimulating growth of human keratinic fibers and/or inhibiting their loss and/or increasing their density : Use of phenylazo benzene, pyridine or pyridazine derivatives of formula (I) as agents for inducing and/or stimulating growth of human keratinic fibers and/or inhibiting their loss and/or increasing their density [Image] Ra, Rb : H, halo, CF3, CN, OR, SR, NRR, NRC(NR)NRR, COR, CSR, COOR, CONRR, CH2COOR, CSNRR, NRCSR, NRCSNRR, NRCOR, NRCONRR, SO2NRR, NRSO2R, NRSO2NRR, SO2R or NO2; 1-10C (un)saturated alkyl optionally substituted with A1 or with (un)saturated 3- to 7-membered rings optionally containing heteroatoms, optionally substituted with A2 and optionally fused with at least one ring optionally containing heteroatoms; or aryl or heteroaryl optionally substituted with A2 and optionally fused with at least one ring optionally containing heteroatoms; X, Y : CRc or N, optionally in N-oxide or quaternized form, but not both N in N-oxide or quaternized form; Rc : Ra or Rb; n, m : 0-5; R : H, (un)saturated 1-10C alkyl, or aryl or heteroaryl optionally substituted with A2; A1H, halo, CF3, CN, OR, SR, NRR, NRC(NR)NRR, COR, CSR, COOR, CONRR, CH2COOR, CSNRR, NRCSR, NRCSNRR, NRCOR, NRCONRR, SO2NRR, NRSO2R, NRSO2NRR, SO2R or NO2; A21-10C alkyl, OR1, SR1, NR1R1, COOR1, COR1 or CH2COOR1; R1H or (un)saturated 1-10C alkyl; and heteroatoms : N, O, S or Se. Independent claims are also included for: (1) Topical composition for care or make-up of human keratinic fibers, comprising at least one compound (I); (2) Cosmetic treatment of human keratinic fibers and/or the skin from which they emerge by applying the above composition to the fibers and/or skin. ACTIVITY : Endocrine-Gen. No biological data available. MECHANISM OF ACTION : None given.

Description

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The subject of the invention is a care or makeup composition for keratinous fibers, containing an effective amount of an azo compound and more particularly an azoaromatic compound, intended to increase their density and / or to improve their appearance. More particularly, the invention relates to a composition for the care or makeup of hair or eyelashes, intended to induce and / or stimulate their growth and / or to slow down their fall. It also relates to a cosmetic treatment process intended to stimulate the growth of keratinous fibers and in particular the hair and / or to slow down their fall.

Hair growth and renewal are mainly determined by the activity of hair follicles and their matrix environment. Their activity is cyclic and comprises essentially three phases, namely the anagen phase, the catagen phase and the telogen phase.

In the anagen phase (active or growth phase), which lasts several years and during which the hair lengthens, follows a very short and transient catagen phase that lasts a few weeks. During this phase, the hair undergoes an evolution, the follicle atrophies and its dermal implantation appears more and more high.

The terminal phase or telogen phase, which lasts a few months, corresponds to a rest phase of the follicle and the hair eventually falls. At the end of this rest period, a new follicle is regenerated, on the spot, and another cycle begins again.

The hair is therefore constantly renewed and about 150,000 hairs of hair, about 10% are at rest and will be replaced in a few months.

The fall or natural loss of hair can be estimated, on average, to a few hundred hairs a day for a normal physiological state. This process of permanent physical renewal undergoes a natural evolution during aging, the hair becomes thinner and their cycles shorter.

In addition, various causes can lead to a significant loss, temporary or permanent hair. It can be a fall and a deterioration of the hair at the end of a pregnancy (post partum), during states of malnutrition or imbalances of food or during states of asthenia or hormonal dysfunction as this may be the case during or after menopause. It can also be a fall or alterations of the hair in relation to seasonal phenomena.

It may also be alopecia, which is mainly due to a disruption of capillary renewal leading initially to the acceleration of the frequency of the cycles at the expense of the quality of the hair, then their quantity. Successive growth cycles result in increasingly fine and shorter hair, gradually turning into an unpigmented down, resulting in progressive depletion of the hair. Areas are affected preferentially, including the temporal or frontal gulfs in humans, and in women, there is diffuse alopecia of the vertex.

The term alopecia also covers a whole family of damage to the hair follicle, the final consequence of which is definitive, partial or general loss of hair. It is more particularly androgenic alopecia. In a large number of cases, the early fall of the hair occurs in subjects predisposed genetically, it is then andro-chrono-genetic alopecia; this form of alopecia concerns especially men.

It is known, moreover, that certain factors such as a hormonal imbalance, a physiological stress, the malnutrition, can accentuate the phenomenon.

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 In certain dermatoses of the scalp with an inflammatory characteristic, such as, for example, psoriasis or seborrheic dermatitis, the hair loss can be greatly accentuated or cause cycles of the highly disturbed follicles.

For many years, it has been sought in the cosmetic or pharmaceutical industry compositions that make it possible to eliminate or reduce alopecia, and in particular to induce or stimulate hair growth or to reduce hair loss.

In this regard, it has already been proposed a large number of compositions comprising a wide variety of active agents, such as, for example, 2,4-diamino-6-piperidinopyrimidine 3-oxide or "minoxidil" described in US Pat. Nos. 4,139,619 and 4,596,619. 812 or its many derivatives such as those described for example in patent applications EP 0353123, EP 0356271, EP 0408442, EP 0522964, EP 0420707, EP 0459890, EP 0519819.

Clinical studies have demonstrated that PGF2-α analogs have the property of causing hair and eyelash growth in humans and animals (Murray A. and Johnstone, MD, 1997. Am. J. Opht., 124 (4), 544-547). In humans, tests on the scalp have shown that an analogue of prostaglandin E2 (viprostol) has the property of increasing capillary density (Roenigk HH, 1988. Clinic Dermatol., 6 (4), 119 -121).

Furthermore, WO 98/33497 discloses pharmaceutical compositions containing prostaglandins or prostaglandin derivatives intended to combat hair loss in humans. Prostaglandins of the type A2, F2 [alpha] and E2 are mentioned as preferred.

However, prostaglandins are molecules with a very short half-life time and acting autocrine or paracrine, reflecting the local and labile nature of prostaglandin metabolism (Narumiya S. et al., 1999, Physiol. 79 (4), 1193-1226).

It therefore appears important, in order to maintain and / or increase the capillary density in humans, to preserve the endogenous reserves of PGF2-a and PGE2 of the different compartments of the hair follicle or of its near skin environment.

A solution giving good results is the administration of lipoxygenase inhibiting compounds and / or cyclooxygenase inducers to promote hair growth; One hypothesis is that the administration of such compounds directs the metabolism of fatty acids towards endogenous prostaglandin synthesis in preference to other pathways.

However, to further improve the results, it would be desirable to be able to prolong the activity of prostaglandins involved in the growth and maintenance of the hair alive.

It is also well known that the differentiation programs of the keratinocytes of the epidermis and the hair follicle are clearly different. Thus, it is known that the keratins of the hair shaft represent a family (Langbein et al., 2001, J. Biol Chem 276: 35132) distinct from that expressed in the epidermis, that the markers of differentiation such as the K1 and K10 keratins are not expressed in the hair follicle and in particular in the outer sheath (Lenoir et al., 1988, Dev Biol 130: 610-620), that trichohyaline (O'Guin et al., 1992 J. Invest Dermatol 98: 24-32) and K6irs keratin (Porter et al., 2001, Br. J. Dermatol.

145: 558-568) are expressed in the hair follicle especially in the inner sheath but not in the epidermis, and that cyclooxygenase type 1, if expressed in the epidermis, is not in keratinocytes of the hair follicle but in the dermal papilla (Michelet et al., 1997, J. Invest Dermatol 108: 205-209).

Surprisingly, the Applicant has now demonstrated that an enzyme specifically involved in the degradation of these prostaglandins is present in the dermal papilla of the hair, which is a critical compartment for the life of the hair. Indeed, the plaintiff has now proved the presence of 15-hydroxy prostaglandin

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 dehydrogenase (15-PGDH abbreviated) at this level. It has further shown that the specific inhibition of 15-PGDH has a beneficial effect on hair growth.

This is why the present invention relates to a care or treatment composition for human keratinous fibers, and in particular human hair, containing at least one particular inhibitor of 15-hydroxyprostaglandin dehydrogenase and a physiologically acceptable medium.

15-PGDH is a key enzyme in the deactivation of prostaglandins, particularly PGF2-a, and PGE2, which are important mediators of hair growth and survival. It meets the EC 1.1.141 classification and is NAD + dependent. She was isolated from pork kidney; in particular, it has been observed to be inhibited by a thyroid hormone, triiodothyronine, at doses much higher than the physiological doses.

However, it has never been proposed to use a 15-PGDH inhibitor to maintain and / or increase the density of human keratinous fibers and in particular human hair and / or to reduce the heterogeneity of the diameters of human keratinous fibers and including human hair. By increasing the density of the keratinous fibers, and in particular the capillary density, it is intended to increase the number of keratinous fibers and in particular of the hair per cm.sup.2 of skin or scalp.

The applicant has found that certain azo compounds and in particular certain azoaromatic, salified or non-salified, are surprisingly provided with an activity that is favorable for improving the density of human keratin fibers such as capillary density. These azoaromatic compounds have the distinction of being inhibitors of 15-PGDH.

By inhibitor of 15-hydroxyprostaglandin dehydrogenase is meant a compound of formula (I) which has little or no inhibitory effect on prostaglandin synthesis, in particular on the synthesis of PGF2-a or PGE2. Preferably, the 15-PGDH inhibitor will be little or no inhibitor of prostaglandin synthase (PGF synthase).

In addition, the Applicant has found that PGF synthase is also expressed in the dermal papilla. Maintaining an effective amount of prostaglandins at the site of action therefore results from a complex biological balance between the synthesis and degradation of these molecules.

The exogenous supply of compounds that inhibit catabolism will therefore be less effective if this activity is combined with inhibition of synthesis.

Thanks to the present invention, it is now possible to use compounds of formula (1), in salt form or not, particularly active, for which the inhibitory activity of 15PGDH is significantly greater than the inhibition activity of PGF synthase.

The subject of the present invention is therefore a care or makeup composition for human keratin fibers, applied topically, containing, in a physiologically acceptable medium, an effective amount of an azo compound of formula (I) or a salt thereof:

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b) un radical alkyle en C1-C10, linéaire ou ramifié, saturé ou non, éventuellement substitué par au moins un substituant AI ou par les cycles C1 saturés ou insaturés, comportant de
3 à 7 atomes et/ou incluant éventuellement au moins un hétéroatome et/ou étant éventuellement substitués par au moins un substituant A2 et/ou éventuellement accolés à au moins un cycle C3 incluant éventuellement au moins un hétéroatome (pour couvrir les cycles condensés) ou c) un cycle aromatique C2 incluant éventuellement au moins un hétéroatome et/ou étant éventuellement substitué par au moins un substituant A2 et/ou éventuellement accolé à un cycle C3 incluant éventuellement au moins un hétéroatome (pour couvrir les cycles condensés) ; 2 ) X et Y identiques ou différents représentent-CRc ou un atome d'azote éventuellement sous forme NO ou quaternisé, Rc ayant la signification de Ra ou Rb, à condition que X et Y ne représentent pas simultanément un atome d'azote sous forme NO ou quaternisé ; 3 ) n et m représentent des entiers allant de 0 à 5 ; - où R, R', R" et R'" identiques ou différents désignent :

#l'atome d'hydrogène ou un radical alkyle en Ci-Cio, linéaire ou ramifié, saturé ou non, # un cycle aromatique C2 incluant éventuellement au moins un hétéroatome, éventuellement substitué par au moins un substituant A2 ; - où A1 est choisi parmi un atome d'halogène, un groupe CF3, CN, OR, SR, NRR',
NRC(=NR')NR"R"', COR, CSR, COOR, CONRR', CSNRR', NRCSR', NRCSNR'R", NRCOR',
NRCONR'R", S02NRR', NRS02R', NRS02NR'R", S02R, N02 ;

- où A2 est choisi parmi les radicaux alkyle en Cl-Clo, linéaires ou ramifiés, OR1, SRi, NRiR'i, COORi, COR1. CH2COOR1, avec R1 et R'1 identiques ou différents désignant l'hydrogène, un radical alkyle en Cl-Clo, linéaire ou ramifié, saturé ou non ; - où l'hétéroatome est choisi parmi N, 0, S ou Se. in which: 1) Ra and Rb, which are identical or different, are chosen from: a) a hydrogen atom, a halogen atom, a CF3, CN, OR, SR, NRR 'group,
NRC (= NR ') NR "R"', COR, CSR, COOR, CONRR ', CH2COOR, CSNRR', NRCSR ',
NRCSNR'R ", NRCOR ', NRCONR'R", SO2NRR', NRSO2R ', NRSO2NR'R ", SO2R, NO2,

b) a linear or branched, saturated or unsaturated C1-C10 alkyl radical, optionally substituted by at least one substituent AI or by saturated or unsaturated C1 rings, comprising
3 to 7 atoms and / or possibly including at least one heteroatom and / or being optionally substituted with at least one substituent A2 and / or optionally contiguous with at least one C3 ring optionally including at least one heteroatom (to cover the condensed rings) or c) an aromatic ring C2 optionally including at least one heteroatom and / or being optionally substituted by at least one substituent A2 and / or optionally attached to a C3 ring optionally including at least one heteroatom (to cover the condensed rings); 2) X and Y, which are identical or different, represent-CRc or a nitrogen atom optionally in NO or quaternized form, Rc having the meaning of Ra or Rb, provided that X and Y do not simultaneously represent a nitrogen atom in the form of NO or quaternized; 3) n and m represent integers ranging from 0 to 5; - where R, R ', R "and R'" identical or different designate:

# the hydrogen atom or a linear or branched, saturated or unsaturated C 1 -C 10 alkyl radical, # a C 2 aromatic ring optionally including at least one heteroatom, optionally substituted with at least one substituent A2; where A1 is selected from a halogen atom, a group CF3, CN, OR, SR, NRR ',
NRC (= NR ') NR "R"', COR, CSR, COOR, CONRR ', CSNRR', NRCSR ', NRCSNR'R ", NRCOR',
NRCONR'R ", SO2NRR ', NRSO2R', NRSO2NR'R", SO2R, NO2;

where A2 is selected from linear or branched C1-C15 alkyl radicals OR1, SR1, NR1R'1, COOR1, COR1. CH2COOR1, with R1 and R'1 identical or different designating hydrogen, a linear or branched C1-C10 alkyl radical, saturated or not; wherein the heteroatom is selected from N, O, S or Se.

This composition is intended in particular to limit the fall of keratinous fibers such as hair and / or increase their density.

Thus, the invention also relates to the particularly cosmetic use of at least one azo compound of formula (I) or a salt thereof, as defined above, as an agent for inducing and / or stimulating the growth of especially human keratin fibers and / or curb their fall and / or increase their density.

The invention also applies to keratinous fibers of mammals of the animal species (dog, horse or cat for example).

The human keratinous fibers to which the invention applies are in particular the hair, the eyebrows, the eyelashes, the beard hair, the mustache hair and the pubic hair. More specifically, the invention is applicable to human hair and / or eyelashes.

Also, the invention also relates to the use of at least one azo compound of formula (I) or one of its salts, as defined above, as an agent for inducing and / or stimulating

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 hair growth of human beings and / or curb their fall and / or increase their density.

The invention also relates to the cosmetic use of at least one azo compound of formula (I) or one of its salts, in a human hair care cosmetic composition for reducing hair loss and / or increase their density and / or treat andro-chrono-genetic alopecia. It also relates to the use of at least one azo compound of formula (I) or a salt thereof for the preparation of a hair composition for human beings, intended to induce and / or stimulate the growth of hair and / or curb their fall and / or increase their density and / or treat androgenic alopecia.

The invention also relates to the cosmetic use of at least one azo compound of formula (I) or a salt thereof, in a human hair care cosmetic composition for treating alopecia of origin natural and in particular androgenic as well as the use of at least one azo compound of formula (I) or a salt thereof for the preparation of a hair care composition of human being, intended to treat the alopecia of natural origin and in particular androgenic. Thus, this composition makes it possible to maintain the hair in good condition and / or to fight against the natural fall of the hair and more particularly that of the men.

The subject of the invention is also the cosmetic use of at least one azo compound of formula (I) or a salt thereof, in a cosmetic composition for the care and / or makeup of human eyelashes, such as agent for inducing and / or stimulating the growth of eyelashes and / or increasing their density and the use of at least one azo compound of formula (I) or a salt thereof, for the preparation of a composition of care and / or treatment of human eyelashes, intended to induce and / or stimulate the growth of eyelashes and / or increase their density. This composition thus makes it possible to maintain the eyelashes in good condition and / or to improve their condition and / or their appearance.

In the remainder of the text, and except express mention, the use of the term compound of formula (I) must be understood as meaning both the compound of formula (1), as one of its salts.

"At least one" according to the invention means one or more (2,3 or more). In particular, the composition may contain one or more compounds of formula (I). This or these compounds may be cis or trans isomers or a mixture of cis / trans isomers.

By "alkyl radical" is meant in the sense of the invention a hydrocarbon radical which may be linear or branched and saturated or unsaturated. In particular, the alkyl radical contains from 1 to 10 carbon atoms and in particular from 1 to 5 atoms. As an example of an alkyl radical which may be used in the invention, mention may be made of the methyl, ethyl, isopropyl, tert-butyl and isopropyl radicals.

As the halogen atom, it is possible to use the chlorine, fluorine or bromine atoms, and better the chlorine and fluorine atoms.

According to the invention, the rings C1, C2 and C3 of the formula (1) comprise from 3 to 7 atoms and better still from 5 to 6 atoms and may comprise one or more heteroatoms such as S, N, O, Se or their associations and thus forming heterocycles Hy. The hydrogen atoms of these rings may, in addition, be partly substituted by a substituent A2. In addition, the cycles Ci and C3 can be saturated or not.

As saturated hydrocarbon rings that may be used in the invention, mention may be made of the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl radical. As unsaturated hydrocarbon rings, mention may be made of the cyclohexenyl or phenyl radical.

According to the invention, C1 and / or C2 and / or C3 may represent a heterocycle Hy comprising from 3 to 7 atoms and better still from 5 to 6 atoms, and including from 1 to 4 heteroatoms chosen from N, O, S, Se and their associations, and better chosen among N, O and their associations. For exemple

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 saturated heterocycle which can be used in the invention, mention may be made of the following heterocycles: azetidine, pyrrolidine, tetrahydrofuran, tetrahydrothiophene, imidazolidine, thiazolidine, pyrazolidine, oxazolidine, isoxazolidine, isothiazole, dihydroisothiazole, isothiazolidine, triazolidine, oxadiazolidine, thiadiazolidine, tetrahydropyridine , piperidine, tetrahydropyran, tetrahydropyrimidine, piperazine, hexahydrotriazines, morpholine.

As an example of unsaturated (or aromatic) heterocycle, the following heterocycles may be used: pyrrole, dihydropyrrole, furan, dihydrofuran, thiophene, dihydrothiophene, imidazole, dihydroimidazole, dihydrothiazole, dihydropyrazole, oxazole, dihydrooxazole, isoxazole , dihydroisoxazole, triazole, dihydrotriazole, oxadiazole, dihydro-oxadiazole, thiadiazole, dihydrothiadiazole, tetrazole, pyridine, dihydropyridine, pyran, dihydropyran, pyrimidine, dihydropyrimidine, pyridazine, pyrazine, pyrazine, diazepine, triazine.

In addition, the C2 rings and the C3 rings may form condensed (hetero) rings, saturated or unsaturated and for example rings naphthalene, tetrahydronaphthalene, quinoline, isoquinoline, indole, benzimidazole, benzothiophene, benzofuran, purine or pteridine or carbazole.

According to the invention, the compounds of formula (I) are in isolated form, that is to say non-polymeric. In addition, the substituents Ra and Rb may be located at any position of the phenyl ring bearing them.

According to the invention, the Ra and Rb carried by the same cycle may be identical or different.

Similarly, the substituents A1 and A2 borne respectively by the same alkyl radical or the same ring may be identical or different.

Preferably, n is an integer representing 0.1, 2.3 or 5. Moreover, m is an integer of in particular 0.1 or 2.

S02NRR', CH2COOR, un radical alkyle en Cl-C5, saturé ou non, tel que méthyle, éthyle ou allyle, éventuellement substitué par un hétérocycle morpholine ou un groupe COOH, avec R et R' ayant la signification indiquée précédemment. En particulier R et/ou R' représentent un atome d'hydrogène, un radical méthyle ou un groupe pyridine. Advantageously, at least one of Ra and Rb represents a group COOR, OR, NO2, CF3,

S02NRR ', CH2COOR, a saturated or unsaturated C1-C5 alkyl radical, such as methyl, ethyl or allyl, optionally substituted by a morpholine heterocycle or a COOH group, with R and R' having the meaning indicated above. In particular, R and / or R 'represent a hydrogen atom, a methyl radical or a pyridine group.

In addition, X and Y independently represent a nitrogen atom or better still a CRc group with Rc representing in particular a hydrogen atom, NO 2, OH, a COOR group or a C 1 -C 5 alkyl radical, saturated or unsaturated, such as methyl or allyl, where R is H, methyl or ethyl.

By salts of compound of formula (1) is meant according to the invention, the organic or inorganic salts of a compound of formula (1).

As inorganic salts that may be used according to the invention, mention may be made of sodium or potassium salts as well as salts of zinc (Zn 2+), calcium (Ca 2+), copper (Cu 2+), iron (Fe 2+), strontium (Sr 2+ ), magnesium (Mg2 +) and manganese (Mn2 +), ammonium; hydroxides, carbonates, halides (such as chlorides), sulphates, nitrates, phosphates. Preferably, the salt is a sodium salt.

The organic salts which can be used according to the invention are, for example, triethanolamine, monoethanolamine, diethanolamine, hexadecylamine and N, N, N ', N'-tetrakis (2-hydroxypropyl) ethylene diamine salts.

As an example of an azo compound of formula (1) that can be used in the invention, mention may be made of the following compounds:

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Composé 1 COOH / OH Me00C NN COOMe Composé 2 0 oH HO N ue 0 H N N Composé 3 on<0-N"NO~-OH 10 0 Composé 4 Ho OH F N'N 1 \ F Composé 5 /)#N=)#<' #OH Composé 6 OH N N' Composé 7 Ho 1 N'N

Compound 1 COOH / OH MeO 2CNN COOMe Compound 2 0 oH HO N ue 0 HNN Compound 3 on <0-N "NO ~ -OH 10 0 Compound 4 Ho OH F N'N 1 \ F Compound 5 /) # N =) # <'#OH Compound 6 OH NN' Compound 7 Ho 1 N'N

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Composé 8 Composé )-("'-0 Composé N/--\0 HO HO 1 / N'N Composé 10 COOH me0oc r- OH MeOOCNJJ iN COOMe Composé 11 COOH me0oc N60" '1YNN INN Composé 12 COOH MEOOC 7' OH Me00C N\N N De préférence, les composés auxquels s'applique l'invention sont des inhibiteurs sélectifs de la 15-PGDH, à savoir qu'ils présentent une activité inhibitrice de la 15-PGDH supérieure à l'activité d'inhibition de la PGF synthase. Autrement dit, le rapport entre les activités inhibitrices respectivement de la PGF synthase et de la 15-PGDH pour une concentration donnée, déterminées notamment par les concentrations inhibitrices de 50% de l'activité enzymatique,

respectivement de la PGF synthase (IC5ofs) et de la 15-PGDH (IC50dh) est au moins supérieur à 1, et notamment d'au moins 3:1, avantageusement supérieur ou égal à 5:1. Les composés préférés de l'invention présentent un ratio IC50f,/IC50dh supérieur ou égal à 10:1, et en particulier supérieur ou égal à 15.

Compound 8 Compound) Compound N / - HO HO 1 / N'N Compound 10 COOH MeOHOCOH COMPOUND 11 COOH MEOHOC N60 "1YNN INN Compound 12 COOH MEOOC 7 'OH Preferably, the compounds to which the invention applies are selective inhibitors of 15-PGDH, namely, that they exhibit 15-PGDH inhibitory activity greater than the inhibitory activity of 15-PGDH. In other words, the ratio between the PGF synthase and 15-PGDH inhibitory activities for a given concentration, determined in particular by the inhibitory concentrations of 50% of the enzymatic activity,

respectively PGF synthase (IC5ofs) and 15-PGDH (IC50dh) is at least greater than 1, and especially at least 3: 1, preferably greater than or equal to 5: 1. The preferred compounds of the invention have a ratio IC50f, / IC50dh greater than or equal to 10: 1, and in particular greater than or equal to 15.

The compounds of formula (1), salified or not, are known as such. They can be manufactured in a known manner and especially as described in the documents VOGEL's Textbook of Practical Organic Chemistry, 5th edition, 1989.

To the applicant's knowledge, no document of the prior art describes or suggests that the azo compounds of formula (1) or their salts have the property of inducing and / or stimulating the growth of human keratin fibers and in particular hair and eyelashes and / or to curb their fall or that these compounds can be used topically to increase the density of human keratinous fibers such as hair and eyelashes.

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 The effective amount of a compound of formula (I) or of one of its salts corresponds to the amount necessary to obtain the desired result (namely to increase the density of keratinous fibers such as hair and eyelashes or to promote their growth) . Those skilled in the art are therefore able to evaluate this effective amount which depends on the nature of the compound used, the person to whom it is applied, and the time of this application.

In the rest of the text, and unless otherwise indicated, the amounts of the various ingredients of the composition are given as a percentage by weight relative to the total weight of the composition.

To give an order of magnitude, according to the invention, the compound of formula (I) or one of its salts or a mixture of compounds of formula (I) and / or their salts may be used in a quantity representing from 10-3% to 10% of the total weight of the composition and preferably in an amount representing from 10-3% to 5% and better still from 10-2% to 2% of the total weight of the composition, for example 0.5 at 2%.

The composition of the invention may be for cosmetic or pharmaceutical use.

Preferably, the composition of the invention is for cosmetic use. Also, the composition must contain a physiologically acceptable medium that is non-toxic and may be applied to the skin, including the scalp and the eyelids, and to the keratinous fibers of human beings. By "cosmetic" is meant in the sense of the invention a composition of appearance, smell and pleasant touch.

The compound of formula (1), salified or not, may be used in a composition that must be ingested, injected or applied to the skin or keratin fibers (on any area to be treated).

According to the invention, the compound of formula (1) or a mixture of compounds of formula (1) may be used orally in an amount of 0.1 to 300 mg per day, especially 5 to 10 mg / day.

A preferred composition of the invention is a composition for cosmetic use and in particular for topical application to the skin and / or keratinous fibers, and more particularly to the scalp, the hair and the eyelashes.

This composition can be in any known galenic forms adapted to the mode of use.

For topical application to the skin or keratinous fibers, the composition may be in the form of an aqueous, alcoholic or aqueous-alcoholic solution or suspension or of an oily suspension, of an emulsion of more or less fluid consistency, and in particular liquid or semi-liquid, obtained by dispersion of a fatty phase in an aqueous phase (O / W) or conversely (W / O), of a solid (O / W) or (W / O) emulsion, of an aqueous gel, hydro-alcoholic or oily more or less fluid or solid, a free or compacted powder for use as such or to incorporate in a physiologically acceptable medium, or microcapsules or microparticles, vesicular dispersions ionic type and or nonionic. It can thus be in the form of a lotion, serum, milk, O / W or W / O cream, ointment, ointment, balm, patch, soaked pad.

It is also possible to envisage a composition in the form of a foam or in the form of a spray or an aerosol then comprising a propellant under pressure.

In particular, the composition for application to the scalp or the hair may be in the form of a hair care lotion, for example a daily or biweekly application, a shampoo or a hair conditioner, in particular application bi-weekly or weekly, a liquid soap or solid scalp daily application, a product shaping the hairstyle (lacquer, product

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 for styling, styling gel), a treating mask, a cream or a foaming gel for cleaning the hair. It can still be in the form of hair dye or mascara to be applied by brush or comb.

Furthermore, for an application on the eyelashes or the hairs, the composition to which the invention applies may be in the form of a mascara, pigmented or not, to be applied to the brush on the eyelashes or on the hairs beard or mustache.

For an injection-use composition, the composition may be in the form of an aqueous lotion or an oily suspension. For oral use, the composition may be in the form of capsules, granules, oral syrups or tablets.

According to a particular embodiment, the composition according to the invention is in the form of hair cream or lotion, shampoo or hair conditioner, hair mascara or eyelash.

The amounts of the various constituents of the composition according to the invention are those generally used in the fields under consideration. In addition, these compositions are prepared according to the usual methods.

When the composition is an emulsion, the proportion of the fatty phase may range from 2% to 80% by weight, and preferably from 5% to 50% by weight relative to the total weight of the composition. The aqueous phase is adjusted as a function of the content of the fatty phase and of the compound (s) (I) as well as that of any additional ingredients, to obtain 100% by weight. In practice, the aqueous phase represents from 5% to 99.9% by weight.

The fatty phase may contain fatty or oily compounds which are liquid at ambient temperature (25 ° C.) and atmospheric pressure (760 mmHg), generally called oils. These oils may or may not be compatible with each other and form a macroscopically homogeneous liquid fatty phase or a two- or three-phase system.

The fatty phase may, in addition to the oils, contain waxes, gums, lipophilic polymers, "pasty" or viscous products containing solid parts and liquid parts.

proportion à l'eau comme les alcools inférieurs en Cl à C8 tel que l'éthanol, l'isopropanol, les polyols comme le propylène glycol, le glycérol, le sorbitol ou encore l'acétone ou l'éther. The aqueous phase contains water and optionally a miscible ingredient in all

proportion to water, such as lower C1 to C8 alcohols such as ethanol, isopropanol, polyols such as propylene glycol, glycerol, sorbitol, or acetone or ether.

The emulsifiers and co-emulsifiers used to obtain a composition in emulsion form are generally used in the cosmetic and pharmaceutical fields. Their nature is, moreover, a function of the meaning of the emulsion. In practice, the emulsifier and optionally the coemulsifier are present in the composition in a proportion ranging from 0.1% to 30% by weight, preferably from 0.5% to 20% by weight and better still from 1% to 8% by weight. .

The emulsion may further contain lipid vesicles and in particular liposomes.

When the composition is in the form of an oily solution or gel, the fatty phase may represent more than 90% of the total weight of the composition.

Advantageously, the composition is an aqueous, alcoholic or hydro-alcoholic solution or suspension and better a water / ethanol solution or suspension. The alcoholic fraction can represent from 5% to 99.9% and better still from 8% to 80%.

For a mascara application, the composition of the invention is especially in the form of a wax-in-water or wax-in-oil dispersion, a gelled oil, an aqueous gel, pigmented or not.

<Desc / Clms Page number 11>

 The composition of the invention may comprise, in addition, other ingredients usually used in the relevant fields, chosen from solvents, thickeners or gelling agents of aqueous phase or oily phase, the dyestuffs soluble in the medium of the composition , solid particles of the fillers or pigments type, antioxidants, preservatives, perfumes, electrolytes, neutralizers, film-forming polymers, UV blocking agents as sunscreens, cosmetic and pharmaceutical active agents with beneficial action for the skin or keratinous fibers, other than the compounds of formula (1), their mixtures. These additives may be present in the composition according to the amounts generally used in the cosmetic and dermatological field and in particular in a proportion of from 0.01 to 50% of the total weight of the composition and better still from 0.1 to 20% and for example from 0 to , 1 to 10%.

Of course, those skilled in the art will take care to choose any additional additives and / or their quantity in such a way that the advantageous properties of the composition according to the invention, namely the specific inhibition of 15-PGDH in particular, are not or substantially not, impaired by the addition contemplated.

As solvents that can be used in the invention, mention may be made of C 2 to C 8 lower alcohols, such as ethanol, isopropanol, propylene glycol and certain light cosmetic oils, such as C 6 to C 16 alkanes.

As oils that can be used in the invention, mention may be made of oils of mineral origin (vaseline oil, hydrogenated isoparaffin), oils of vegetable origin (liquid fraction of shea butter, sunflower oil, apricot oil, alcohol or fatty acid), oils of animal origin (perhydrosqualene), synthetic oils (fatty acid ester, Purcellin oil), silicone oils (linear or cyclic polydimethylsiloxane, phenyltrimethicone) and fluorinated oils (perfluoropolyethers). As waxes, mention may be made of silicone waxes, beeswax, rice waxes, candellila waxes, carnauba or paraffin waxes, and polyethylene waxes.

alkyle > 8) et leurs mélanges pour une émulsion E/H. On peut aussi utiliser le monostéarate ou monolaurate de polyéthylène glycol, le stéarate ou oléate de sorbitol polyoxyéthyléné, les diméthiconecopolyols et leurs mélanges pour une émulsion H/E. As emulsifiers that can be used in the invention, mention may be made, for example, of glycerol stearate or laurate, sorbitol stearates or oleates, and alkyl dimethiconecopolyol (with

alkyl> 8) and mixtures thereof for W / O emulsion. It is also possible to use polyethylene glycol monostearate or monolaurate, polyoxyethylenated sorbitol stearate or oleate, dimethiconecopolyols and their mixtures for an O / W emulsion.

As hydrophilic gelling agents that may be used in the invention, mention may be made of carboxyvinyl polymers (carbomer), acrylic copolymers such as acrylate / alkylacrylate copolymers, polyacrylamides, polysaccharides such as hydroxypropylcellulose, natural gums and clays, and, as lipophilic gelling agents, mention may be made of modified clays such as Bentones, metal salts of fatty acids such as aluminum stearates, hydrophobic treated silica, ethylcellulose, and mixtures thereof.

As cosmetic or pharmaceutical active, other than the compound of formula (1) that can be used in the invention, mention may be made of hydrophilic active agents such as proteins or protein hydrolysates, amino acids, polyols, urea and allantoin sugars and sugar derivatives, water-soluble vitamins, plant extracts (those of Iridaceae or soya) and hydroxy acids such as fruit acids or salicylic acid; and lipophilic active agents, such as retinol (vitamin A) and its derivatives (retinol palmitate), tocopherol (vitamin E) and its derivatives (tocopherol acetate), essential fatty acids, ceramides, essential oils, derivatives salicylic acid such as 5-octanoyl salicylic acid, esters of hydroxy acids, phospholipids such as lecithin, and mixtures thereof.

According to a particular embodiment of the invention, it is possible to associate with the compound of formula (1) or one of its salts at least one additional compound promoting the regrowth and / or limiting the fall of keratinous fibers (hair, eyelashes). ). These additional compounds are chosen in particular from the lipoxygenase inhibitors as described in EP 648488, the inhibitors of bradykinin described in particular in EP 845700, and prostaglandins and their derivatives.

<Desc / Clms Page number 12>

 especially those described in WO 98/33497, WO 95/11003, JP 97-100091, JP 96-134242, prostaglandin receptor agonists or antagonists, nonprostanoic prostaglandin analogs as described in EP 1175891 and EP1175890, WO 1 / 74307, WO 01/74313, WO 01/74314, WO 01/74315 or WO 01/72268, mixtures thereof.

As other additional active compounds that promote the growth of keratin fibers and / or limit their fall that may be present in the composition according to the invention, mention may be made of vasodilators, antiandrogens, cyclosporins and their analogs, antimicrobials or antifungals, anti-inflammatory drugs, retinoids, tri-terpenes, alone or as a mixture.

Vasodilators which may be used include potassium channel agonists including minoxidil and the compounds described in US Pat. Nos. 3,382,247, 5,706,092, 5,772,990, 5,700,443, 46,694,5, 43,805, 97,374, chromakalim, 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 the compounds described in US Pat. No. 5,480,913, flutamide, oxendolone, spironolactone, diethylstilbestrol and the compounds described in US 5,411,981, 5,565,467 and 4,910,226.

C1-C6 comme les nicotinates de méthyle ou d'hexyle. The anti-microbial or antifungal compounds may be chosen from selenium derivatives, octopirox, triclocarban, triclosan, pyrithione zinc, itraconazole, asiatic acid, hinokitiol, mipirocine, tetracyclines, in particular erythromycin and the compounds described in EP 680745, 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 alkyl nicotinates in

C1-C6 such as methyl or hexyl nicotinates.

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 a-bisabolol, benzydamine, acid salicylic acid and the compounds described in EP 770399, WO 94/06434 and FR 2268523.

The retinoids may be selected from isotretinoin, acitretin, tazarotene, retinal and adapalene.

Other compounds that are active to promote the growth and / or limit the fall of keratinous fibers such as hair and eyelashes, which can be used in combination with the compound of formula (1), which may or may not be salified, include aminexil, 0 - [(9Z, 12Z) -octadeca-9,12-dianoyl] hexapyranose, benzalkonium chloride, benzethonium chloride, phenol, estradiol, chlorpheniramine maleate, chlorophyllin derivatives, 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, substituted aryl ethenes, 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, IL-1 or IL-6 inhibitors, IL-10 promoters, TNF inhibitors, benzophenones , hydantoin, retinoic acid; vitamins such as vitamin D, vitamin B12 analogues and panthotenol; triterpenes such as ursolic acid and the compounds described in US 5529769, US 5468888, US 5631282; antipruritic agents such as thenaldine, trimeprazine or cyproheptadine; antiparasitic agents, particularly metronidazole, crotamiton or pyrethrinoids; calcium antagonists, such as cinnarizine, diltiazem, nimodipine, verapamil, alverine and nifedipine; hormones such as

<Desc / Clms Page number 13>

 estriol or analogues, thyroxine and its salts, progesterone; FP (F-type prostaglandin receptor) receptor agonists such as latanoprost, bimatoprost, travoprost, unoprostone and butaprost; their mixtures.

Advantageously, the composition according to the invention will comprise at least one inhibitor of 15PGDH as defined above and at least one prostaglandin or a prostaglandin derivative such as, for example, prostaglandins of series 2, in particular PGF2-a and PGE2 in saline form or esters (eg isopropyl esters), their derivatives such as 16,16 dimethyl PGE2, 17 phenyl PGE2, 16,16 dimethyl PGF2-a, 17 phenyl PGF2-a prostaglandins of series 1 such as 11 deoxyprostaglandin E1 , 1 deoxy prostaglandin E1 in saline or ester form, their analogues including latanoprost, travoprost, bimatoprost, unoprostone, fluprostenol, cloprostenol, viprostol, butaprost, misoprostol, their salts or their esters.

Preferably, the composition contains at least one non-prostanoic agonist of the EP2 and / or EP4 receptors, in particular as described in EP 1175892.

It is also conceivable that the composition comprising at least the compound of formula (1), salified or not, is in liposome form, such as in particular described in WO 94/22468. Thus, the liposome encapsulated compound can be delivered selectively to the hair follicle.

The composition according to the invention can be applied to the alopecic areas of the scalp and hair of an individual, and possibly left in contact for several hours and possibly rinsed.

For example, it is possible to apply the composition containing an effective amount of a compound of formula (1), salified or not, in the evening, keep it in contact all night and possibly shampoo in the morning. These applications can be renewed daily for one or more months depending on the individual.

Thus, the subject of the present invention is also a process for the cosmetic treatment of human keratinous fibers and / or of the skin from which said fibers, including scalp and eyelids, emerge, intended to stimulate the growth of keratinous fibers. being human and / or curbing their fall, characterized in that it consists in applying to the keratinous fibers and / or the skin from which said fibers emerge, a cosmetic composition comprising an effective amount of at least one compound of formula (1) or one of its salts, to leave it in contact with the fibers and / or the skin, and optionally to rinse the fibers and / or the skin.

This treatment method has the characteristics of a cosmetic process insofar as it makes it possible to improve the aesthetics of human keratin fibers by giving them greater vigor and an improved appearance. In addition, it can be used daily for several months, without a medical prescription.

More specifically, the subject of the present invention is a process for the cosmetic care of human hair and / or scalp, with a view to improving their state and / or their appearance, characterized in that it consists in applying to the hair and or or the scalp, a cosmetic composition comprising an effective amount of at least one compound of formula (1) or a salt thereof, to leave the latter in contact with the hair and / or the scalp, and possibly rinsing the hair and / or the scalp.

Advantageously, in the process according to the invention, 5 to 500 L of a solution or composition as defined above, comprising from 0.001% to 5% of inhibitor of the invention, are applied to areas to be treated or treated with scalp. 15-PGDH.

The invention also relates to a method of cosmetic care and / or makeup of eyelashes

<Desc / Clms Page number 14>

 in order to improve their state and / or their appearance, characterized in that it consists in applying to the eyelashes and / or the eyelids a mascara composition comprising at least one compound of formula (I) or one of its salts and to leave it in contact with the eyelashes and / or the eyelids. This mascara composition can be applied alone or as an undercoat of a conventional pigmented mascara and removed as a conventional pigmented mascara.

The subject of the invention is also a composition for the care or makeup of keratinous fibers, comprising in a physiologically acceptable medium, in particular a cosmetic medium, at least one derivative of formula (I) or one of its salts and at least one active ingredient. additional promoting the regrowth of human keratin fibers and / or limiting the fall selected from aminexil, FP receptor agonists and vasodilators and more particularly selected from aminexil, minoxidil, latanoprost, butaprost and travoprost.

Examples of embodiments of the invention which will not in any way limit its scope will now be given by way of illustration.

 EXAMPLE 1: Demonstration of the specific inhibitory properties of 15-PGDH of the compounds of formula (1).

1) Test on 15-PGDH The 15-PGDH enzyme is obtained as described in application FR 02/05067 filed in the name of L'Oréal, in suspension in a medium adapted to a concentration of 0.3 mg / ml and then blocked at -80 C. For testing purposes, this suspension is thawed and stored in ice.

Quentin Fallavier), 50 uM de Prostaglandine E2 (P4172, Sigma-Aldrich, L'isle D'Abeau Chesne, BP 701, 38297, Saint Quentin Fallavier). In addition, a 100 mM Tris buffer, pH = 7.4, containing 0.1 mM of dithiothreitol (D5545, Sigma-Aldrich, L'Isle d'Abeau Chesne, BP 701.38297, Saint Quentin Fallavier), 1, is prepared. 5 mM p-NAD (N6522, Sigma-Aldrich, L'Isle d'Abeau Chesne, BP 701, 38297, Saint

Quentin Fallavier), 50 μM Prostaglandin E2 (P4172, Sigma-Aldrich, The Isle of Abeau Chesne, BP 701, 38297, Saint Quentin Fallavier).

In the tank of a spectrophotometer (Perkin-Elmer, Lambda 2) thermostated at 37 C, whose measuring wavelength is set at 340 nm, are introduced 0.965 ml of this buffer (previously heated to 37 C). 0.035 ml of 37 C enzyme suspension are introduced into the cuvette at the same time as the recording (corresponding to an increase in the optical density at 340 nm). The maximum reaction rate is recorded.

composé (I)) ; les résultats indiqués représentent la concentration à laquelle le composé de formule (I) réduit de 50% de l'activité enzymatique, notés IC50dh de 15-PGDH. The test values (containing the compound (I)) are compared with the control value (without

compound (I)); the results indicated represent the concentration at which the compound of formula (I) reduces by 50% of the enzymatic activity, denoted IC50dh of 15-PGDH.

2) Test on PGF Synthase The PGFS enzyme is obtained as described in document FR-A-02/05067, at a concentration of 0.5 mg / ml, suspended in a suitable medium, and blocked at -80 ° C. For test purposes, this suspension is thawed and stored in ice.

Chesne, BP 701, 38297, Saint Quentin Fallavier) et 100 uM de (3-NADPH (N1630, Sigma- Aldrich, L'isle D'Abeau Chesne, BP 701, 38297, Saint Quentin Fallavier). Furthermore, a 100 mM Tris buffer, pH = 6.5, containing 20 M of 9,10 phenanthrene quinone * (P2896, Sigma-Aldrich, L'Isle d'Abeau) is prepared in a brown bottle (protected from light).

Chesne, PO Box 701, 38297, Saint Quentin Fallavier) and 100 μM of (3-NADPH (N1630, Sigma-Aldrich, The Isle of Abeau Chesne, BP 701, 38297, Saint Quentin Fallavier).

* A stock solution titrant 1 mM is prepared in absolute ethanol, heated to 40 C; the bottle is placed in an ultrasound tank to facilitate the solubilization of the product.

<Desc / Clms Page number 15>

 In the tank of a spectrophotometer (Perkin-Elmer, Lambda 2) thermostated at 37 C, whose measuring wavelength is set at 340 nm are introduced 0.950 ml of this buffer (previously heated to 37 C). 0.05 ml of 37 C enzyme suspension are introduced into the cuvette at the same time as the recording (corresponding to a drop in the optical density at 340 nm). The maximum reaction rate is recorded.

composé (I)) ; les résultats indiqués représentent la concentration à laquelle le composé de formule (I) réduit de 50% l'activité enzymatique de PGFS, à savoir IC50fs.

The test values (containing the compound (I)) are compared with the control value (without

compound (I)); the results indicated represent the concentration at which the compound of formula (I) reduces by 50% the enzymatic activity of PGFS, ie IC50fs.

<Tb>
<Tb>

Compound <SEP> Inhibition <SEP> 15-PGDH <SEP> Inhibition <SEP> of <SEP> PGFS
<tb> IC50 <SEP>% <SEP>% <SEP>% <SEP>% <SE> IC50
<tb> (nm) <SEP> inhibition <SEP> inhibition <SEP> inhibition <SEP> inhibition <SEP> (M)
<Tb>

à 50 Ilm à5 à50 à5 m%

at 50 Ilm at 5 to 50 to 5 m%

<Tb>
<tb> 1
<tb> COOH
<Tb>

1 200 100 - -* -* > 50 MEOOC -Çl N,6 200 100 MeOOC.NJJ

1,200 100 - - * - *> 50 MEOOC-E N N, 6 200 100 MeOOC.NJJ

<Tb>
<tb> COOMe
<tb> 2
<Tb>

0 " HO N"N -* 90 50 100 i , '1 " H N N

0 "HO N" N - * 90 50 100 i, '1 "HNN

<Tb>
<tb> O- # N + <SEP> N # N <SEP> OH
<tb> O <SEP> O <SEP> ONa +
<tb> 4
<tb>#OH<SEP> F <SEP> F
<Tb>

H07LON" N \ / F * 60

H07LON "N \ / F * 60

<Tb>
<tb> 5
<Tb>

G-N-N r-< OH ~ \==/ * 60 ~* ~* * *

GNN r- <OH ~ \ == / * 60 ~ * ~ * * *

<Desc / Clms Page number 16>

<Tb>
<tb> Compound <SEP> Inhibition <SEP> 15-PGDH <SEP> Inhibition <SEP> of <SEP> PGFS <SEP>
<Tb>

!Cso % % % % IC50 (nm) inhibition inhibition inhibition inhibition (gm) à 50 nm à 5 iim à 50 jim à 5 !lm %

IC 50 (nm) inhibition inhibition inhibition (gm) at 50 nm at 5 μm at 50 μm at 5 μm

<Tb>
<tb> 6
<tb> OH
<tb> N # N <SEP> 50
<Tb>
<tb># O # O
<tb> HO # <SEP> N # <SEP> - * <SEP> 15
<tb> * <SEP> 15 <SEP> *
<Tb>

'9 N"-o ECo N-0 HO ,9 N"N-Q -* 15 * Non déterminé De ce tableau, il ressort que le composé 1 est bien un inhibiteur de 15-PGDH. De plus, il inhibe de façon plus efficace et sélective la 15-PGDH que la PGFS. Ainsi le rapport IC5ofs/IC5odh est supérieur à 130.

## STR1 ## It is apparent from this table that compound 1 is indeed an inhibitor of 15-PGDH. In addition, it more efficiently and selectively inhibits 15-PGDH than PGFS. Thus the ratio IC5ofs / IC5odh is greater than 130.

The compositions below are obtained by the usual techniques commonly used in the cosmetics or pharmaceutical field.

EXAMPLE 2: Hair lotion - Compound 1 0.80 g - Propylene glycol 10.00 g - Isopropyl alcohol qs 100.00 g This lotion is applied to the scalp, once or twice a day, at a rate of 1 ml per ml. application, gently massaging the scalp to penetrate the asset. The hair is then dried in the open air. This lotion helps reduce hair loss and promote their regrowth.

EXAMPLE 3: Hair Lotion - Compound 4 1.00 g - Propylene glycol 30.00 g

<Desc / Clms Page number 17>

 - Ethyl alcohol 40.00 g - Water qs 100.00 g This lotion is applied to the scalp, once or twice a day, at the rate of 1 ml per application, by gently massaging the scalp to penetrate the scalp. active. The hair is then dried in the open air.

EXAMPLE 4: Hair lotion - Compound 3 in acid form 1 g - Ethyl alcohol 40.00 g - NaOH qs (*) - Water qs 100.00 g (*) enough to neutralize the acid function carried by phenyl ring (Rb) This lotion is applied to the scalp, once or twice a day, at a rate of 1 ml per application by gently massaging the scalp to penetrate the active ingredient.

 EXAMPLE 5 Mascaracire / Water - Beeswax 6.00% - Paraffin Wax 13.00% - Hydrogenated Jojoba Oil 2% - Water-soluble Film-forming Polymer 3% - Triethanolamine Stearate 8% - Compound 1 1% - Black Pigment 5% - Preservative qs - Water qs 100% This mascara is applied on eyelashes like a classic mascara with a mascara brush.

EXAMPLE 6: Hair Lotion - Compound 1 0.10 g - Latanoprost 0.10 g - Propylene glycol 30.00 g - Ethyl alcohol 40.00 g - Water qs 100.00 g This lotion is applied to the scalp, one to twice a day, at a rate of 1 ml per application by gently massaging the scalp to penetrate the asset.

Claims (3)

 NRCSNR'R ", NRCOR ', NRCONR'R", SO2NRR', NRS02R ', NRS02NR, R ", SO2R, NO2, b) a linear or branched, C1-C10 alkyl radical, saturated or unsaturated, optionally substituted with at least one substituent A1 or with saturated or unsaturated C1 rings containing

NRC (= NR ') NR "R"', COR, CSR, COOR, CONRR ', CH2COOR, CSNRR', NRCSR ',  in which: 1) Ra and Rb, which are identical or different, are chosen from: a) a hydrogen atom, a halogen atom, a CF3, CN, OR, SR, NRR 'group,

 1. Use of an effective amount of at least one azo compound of formula (I) or a salt thereof,  where A2 is chosen from linear or branched C1-C10 alkyl radicals, OR1, SR1, NR1R'1, COLORI, COR1, CH2COORi, with R1 and R'1 being identical or different and denoting hydrogen, an alkyl radical containing C1-C10, linear or branched, saturated or not; wherein the heteroatom is chosen from N, O, S or Se, as an agent for inducing and / or stimulating the growth of human keratinous fibers and / or curbing their fall and / or increasing their density.

NRCONR'R ", SO2NRR ', NRSO2R', NRSO2NR'R", SO2R, NO2; 3 to 7 atoms and / or possibly including at least one heteroatom and / or being optionally substituted by at least one substituent A2, and / or optionally contiguous to at least one C3 ring optionally including at least one heteroatom, or c) an aromatic ring C2 optionally including at least one heteroatom and / or being optionally substituted with at least one substituent A2 and / or optionally fused to at least one C3 ring optionally including at least one heteroatom; 2) X and Y, which are identical or different, represent-CRc or a nitrogen atom optionally in NO or quaternized form, Rc having the meaning of Ra or Rb, provided that X and Y do not simultaneously represent a nitrogen atom in the form of NO or quaternized; 3) n and m represent integers ranging from 0 to 5; where R, R, 'R' and R '"identical or different designate: # the hydrogen atom or a linear or branched, saturated or unsaturated C1-C10 alkyl radical, # a C2 aromatic ring optionally including minus one heteroatom, optionally substituted with at least one substituent A2; where A1 is selected from a halogen atom, a CF3 group, CN, OR, SR, NRR ', NRC (= NR') NR "R" ', COR, CSR, COOR, CONRR', CSNRR ', NRCSR ', NRCSNR'R', NRCOR ', <Desc / Clms Page number 19> NRCSNR'R ", NRCOR ', NRCONR'R", SOzNRR', NRS02R ', NRSO2NR'R ", SO2R, NO2, b) a C1-C10 alkyl radical, linear or branched, saturated or unsaturated, optionally substituted with at least one substituent A1 or with saturated or unsaturated C1 rings containing NRC (= NR ') NR "R"', COR, CSR, COOR, CONRR ', CH2COOR, CSNRR', NRCSR ',  in which: 1) Ra and Rb, which are identical or different, are chosen from: a) a hydrogen atom, a halogen atom, a CF3, CN, OR, SR, NRR 'group,

 2. Cosmetic use of at least one azo compound of formula (I) or a salt thereof,  NRCONR'R ", SOzNRR ', NRSO2R', NRSOZNR'R", SO2R, NO2; where A2 is chosen from linear or branched C1-C1Q alkyl radicals, OR1, SR1. NR1R'1, COOR, COR1, CH2COOR1, with R1 and R'1 identical or different designating hydrogen, a linear or branched C1-C10 alkyl radical, saturated or not; - Where the heteroatom is selected from N, 0, S or Se, in a cosmetic composition care and / or makeup of human keratin fibers to induce and / or stimulate their growth, slow down their fall and / or increase their density.

3 to 7 atoms and / or possibly including at least one heteroatom and / or being optionally substituted by at least one substituent A2, and / or optionally contiguous to at least one C3 ring optionally including at least one heteroatom, or c) an aromatic ring C2 optionally including at least one heteroatom and / or being optionally substituted with at least one substituent A2 and / or optionally fused to at least one C3 ring optionally including at least one heteroatom; 2) X and Y, which are identical or different, represent-CRc or a nitrogen atom optionally in NO or quaternized form, Rc having the meaning of Ra or Rb, provided that X and Y do not simultaneously represent a nitrogen atom in the form of NO or quaternized; 3) n and m represent integers ranging from 0 to 5; where R, R, 'R' and R '"identical or different designate: # the hydrogen atom or a linear or branched, saturated or unsaturated C1-C10 alkyl radical, # a C2 aromatic ring optionally including minus one heteroatom, optionally substituted with at least one substituent A2; where A1 is selected from a halogen atom, a group CF3, CN, OR, SR, NRR ', NRC (= NR') NR "R '", COR, CSR, COOR, CONRR', CSNRR ', NRCSR ', NRCSNR'R', NRCOR ', <Desc / Clms Page number 20> NRCSNR'R ", NRCOR ', NRCONR'R", SO2NRR', NRS02R ', NRS02NR'R ", SO2R, NO2, b) an alkyl radical C1-C10, linear or branched, saturated or unsaturated, optionally substituted with at least one substituent A1 or with saturated or unsaturated C1 rings containing NRC (= NR ') NR "R"', COR, CSR, COOR, CONRR ', CH2COOR, CSNRR', NRCSR ',  in which: 1) Ra and Rb, which are identical or different, are chosen from: a) a hydrogen atom, a halogen atom, a CF3, CN, OR, SR, NRR 'group,

 3. Use of at least one azo compound of formula (I) or a salt thereof  where A2 is chosen from linear or branched C1-C15 alkyl radicals, OR1, SR1, NR, R ', COOR, COR1, CH2COOR1, with R1 and R'1 being identical or different, denoting hydrogen, a radical; C1-C10 alkyl, linear or branched, saturated or unsaturated; wherein the heteroatom is chosen from N, O, S or Se, for the manufacture of a composition for the care or treatment of human keratinous fibers, intended to induce and / or stimulate the growth of the fibers and / or to slow down their fall and / or increase their density.

NRCONR'R ", SO2NRR ', NRSO2R', NRSO2NR'R", SO2R, NO2; NRC (= NR ') NR "R"', COR, CSR, COOR, CONRR ', CSNRR', NRCSR ', NRCSNR'R ", NRCOR', 3 to 7 atoms and / or possibly including at least one heteroatom and / or being optionally substituted by at least one substituent A2, and / or optionally contiguous to at least one C3 ring optionally including at least one heteroatom, or c) an aromatic ring C2 optionally including at least one heteroatom and / or being optionally substituted with at least one substituent A2 and / or optionally fused to at least one C3 ring optionally including at least one heteroatom; 2) X and Y, which are identical or different, represent-CRc or a nitrogen atom optionally in NO or quaternized form, Rc having the meaning of Ra or Rb, provided that X and Y do not simultaneously represent a nitrogen atom in the form of NO or quaternized; 3) n and m represent integers ranging from 0 to 5; where R, R, 'R' and R '"identical or different designate: # the hydrogen atom or a linear or branched, saturated or unsaturated C1-C10 alkyl radical, # a C2 aromatic ring optionally including minus one heteroatom, optionally substituted with at least one substituent A2; where A1 is selected from a halogen atom, a group CF3, CN, OR, SR, NRR ', 4. Use according to one of the preceding claims, characterized in that the keratin fibers are hair, eyebrows, eyelashes, beard hair, mustache and pubic hair. <Desc / Clms Page number 21> NRCSNR'R ", NRCOR ', NRCONR'R", SO2NRR', NRS02R ', NRS02NR'R ", SO2R, NO2, b) a C1-C10 alkyl radical, linear or branched, saturated or unsaturated, optionally substituted with at least one substituent A1 or with saturated or unsaturated C1 rings containing NRC (= NR ') NR "R"', COR, CSR, COOR, CONRR ', CHzCOOR, CSNRR', NRCSR ',  in which: 1) Ra and Rb, which are identical or different, are chosen from: a) a hydrogen atom, a halogen atom, a CF3, CN, OR, SR, NRR 'group,

 5. Use of an effective amount of at least one azo compound of formula (I) or a salt thereof  where A2 is chosen from linear or branched C1-C15 alkyl radicals, OR1, SR1, NR1R'1, COOR1, COR1, CH2COOR1, with R1 and R'1 being identical or different and denoting hydrogen, an alkyl radical containing C1-C10, linear or branched, saturated or not; wherein the heteroatom is selected from N, O, S or Se, in a human hair care cosmetic composition for reducing hair loss and / or increasing its density and / or treating andro-chronological alopecia. genetics and / or to treat alopecia of natural origin.

NRCONR'R ", SO2NRR ', NRSO2R', NRSO2NR'R", SO2R, NO2; NRC (= NR ') NR "R"', COR, CSR, COOR, CONRR ', CSNRR', NRCSR ', NRCSNR'R ", NRCOR', 3 to 7 atoms and / or optionally including at least one heteroatom and / or being optionally substituted by at least one substituent A2, and / or optionally contiguous to at least one C3 ring optionally including at least one heteroatom, or c) an aromatic ring C2 optionally including at least one heteroatom and / or being optionally substituted with at least one substituent A2 and / or optionally fused to at least one C3 ring optionally including at least one heteroatom; 2) X and Y, which are identical or different, represent-CRc or a nitrogen atom optionally in NO or quaternized form, Rc having the meaning of Ra or Rb, provided that X and Y do not simultaneously represent a nitrogen atom in the form of NO or quaternized; 3) n and m represent integers ranging from 0 to 5; where R, R, 'R' and R '"identical or different designate: # the hydrogen atom or a linear or branched, saturated or unsaturated C1-C10 alkyl radical, # a C2 aromatic ring optionally including minus one heteroatom, optionally substituted with at least one substituent A2; where A1 is selected from a halogen atom, a group CF3, CN, OR, SR, NRR ', <Desc / Clms Page number 22> NRCSNR'R ", NRCOR ', NRCONR'R", SO2NRR', NRS02R ', NRS02NR'R ", SO2R, NO2, b) a C1-C10 alkyl radical, linear or branched, saturated or unsaturated, optionally substituted with at least one substituent A1 or with saturated or unsaturated C1 rings containing  in which: 1) Ra and Rb, which are identical or different, are chosen from: a) a hydrogen atom, a halogen atom, a CF3 group, CN, OR, SR, NRR ', NRC (= NR') NR " R "', COR, CSR, COOR, CONRR', CH2COOR, CSNRR ', NRCSR',

 6. Cosmetic use of at least one azo compound of formula (I) or a salt thereof  where A2 is chosen from linear or branched C1-C15 alkyl radicals, OR1, SR1, NR1R'1, COLORI, COR1, CH2COOR1, with R1 and R'1 being identical or different and denoting hydrogen, an alkyl radical containing C1-C10, linear or branched, saturated or not; wherein the heteroatom is chosen from N, O, S or Se, for the preparation of a human hair composition, intended to induce and / or stimulate the growth of the hair and / or to curb their fall and / or to increase their density and / or treat androgenic alopecia and / or treat alopecia of natural origin.

NRCONR'R ", SO2NRR ', NRSO2R', NRSO2NR'R", SO2R, NO2; NRC (= NR ') NR "R"', COR, CSR, COOR, CONRR ', CSNRR', NRCSR ', NRCSNR'R ", NRCOR', 3 to 7 atoms and / or possibly including at least one heteroatom and / or being optionally substituted by at least one substituent A2, and / or optionally contiguous to at least one C3 ring optionally including at least one heteroatom, or c) an aromatic ring C2 optionally including at least one heteroatom and / or being optionally substituted with at least one substituent A2 and / or optionally fused to at least one C3 ring optionally including at least one heteroatom; 2) X and Y, which are identical or different, represent-CRc or a nitrogen atom optionally in NO or quaternized form, Rc having the meaning of Ra or Rb, provided that X and Y do not simultaneously represent a nitrogen atom in the form of NO or quaternized; 3) n and m represent integers ranging from 0 to 5; where R, R, 'R' and R '"identical or different designate: # the hydrogen atom or a linear or branched, saturated or unsaturated C1-C10 alkyl radical, # a C2 aromatic ring optionally including minus one heteroatom, optionally substituted with at least one substituent A2; where A1 is selected from a halogen atom, a group CF3, CN, OR, SR, NRR ', <Desc / Clms Page number 23> NRCSNR'R ", NRCOR ', NRCONR'R", SO2NRR', NRS02R ', NRS02NR'R ", SO2R, NO2, b) a C1-C10 alkyl radical, linear or branched, saturated or unsaturated, optionally substituted with at least one substituent A1 or with saturated or unsaturated C1 rings containing  in which: 1) Ra and Rb, which are identical or different, are chosen from: a) a hydrogen atom, a halogen atom, a CF3 group, CN, OR, SR, NRR ', NRC (= NR') NR " R "', COR, CSR, COOR, CONRR', CH2COOR, CSNRR ', NRCSR',

 7. Cosmetic use of at least one azo compound of formula (I) or of one of its salts  where A2 is chosen from linear or branched C1-C10 alkyl radicals, OR, SR1, NR1R'1, COOR1, COR1, CH2COOR1, with R1 and R'1 being identical or different and denoting hydrogen, a C1-alkyl radical; -C10, linear or branched, saturated or not; wherein the heteroatom is chosen from N, O, S or Se, in a cosmetic composition for the care and / or makeup of human eyelashes, as an agent for inducing and / or stimulating the growth of eyelashes and / or increasing their density.

NRCONR'R ", SO2NRR ', NRSO2R', NRSO2NR'R", SO2R, NO2; NRC (= NR ') NR "R"', COR, CSR, COOR, CONRR ', CSNRR', NRCSR ', NRCSNR'R ", NRCOR', 3 to 7 atoms and / or possibly including at least one heteroatom and / or being optionally substituted by at least one substituent A2, and / or optionally contiguous to at least one C3 ring optionally including at least one heteroatom, or c) an aromatic ring C2 optionally including at least one heteroatom and / or being optionally substituted with at least one substituent A2 and / or optionally fused to at least one C3 ring optionally including at least one heteroatom; 2) X and Y, which are identical or different, represent-CRc or a nitrogen atom optionally in NO or quaternized form, Rc having the meaning of Ra or Rb, provided that X and Y do not simultaneously represent a nitrogen atom in the form of NO or quaternized; 3) n and m represent integers ranging from 0 to 5; where R, R, 'R' and R '"identical or different designate: # the hydrogen atom or a linear or branched, saturated or unsaturated C1-C10 alkyl radical, # a C2 aromatic ring optionally including minus one heteroatom, optionally substituted with at least one substituent A2; where A1 is selected from a halogen atom, a group CF3, CN, OR, SR, NRR ', <Desc / Clms Page number 24> NRCSNR'R ", NRCOR ', NRCONR'R", SO2NRR', NRS02R ', NRS02NR'R ", SO2R, NO2, b) an alkyl radical C1-C10, linear or branched, saturated or unsaturated, optionally substituted with at least one substituent A1 or with saturated or unsaturated C1 rings containing NRC (= NR ') NR "R"', COR, CSR, COOR, CONRR ', CH2COOR, CSNRR', NRCSR ',  in which: 1) Ra and Rb, which are identical or different, are chosen from: a) a hydrogen atom, a halogen atom, a CF3, CN, OR, SR, NRR 'group,

 8. Use of at least one azo compound of formula (I) or one of its salts,  where A2 is chosen from linear or branched C1-C10 alkyl radicals, OR1, SR1, NR1R'1, COOR1, COR1, CH2COORi, with R1 and R'1 being identical or different and denoting hydrogen, C1-C10 alkyl radical, linear or branched, saturated or not; wherein the heteroatom is chosen from N, O, S or Se, for the preparation of a composition for the care and / or treatment of human eyelashes intended to induce and / or stimulate the growth of the eyelashes and / or to increase their density .

NRCONR'R ", SO2NRR ', NRSO2R', NRSO2NR'R", SO2R, NO2; 3 to 7 atoms and / or optionally including at least one heteroatom and / or being optionally substituted by at least one substituent A2, and / or optionally contiguous to at least one C3 ring optionally including at least one heteroatom, or c) an aromatic ring C2 optionally including at least one heteroatom and / or being optionally substituted with at least one substituent A2 and / or optionally fused to at least one C3 ring optionally including at least one heteroatom; 2) X and Y, which are identical or different, represent-CRc or a nitrogen atom optionally in NO or quaternized form, Rc having the meaning of Ra or Rb, provided that X and Y do not simultaneously represent a nitrogen atom in the form of NO or quaternized; 3) n and m represent integers ranging from 0 to 5; where R, R, 'R' and R '"identical or different designate: # the hydrogen atom or a linear or branched, saturated or unsaturated C1-C10 alkyl radical, # a C2 aromatic ring optionally including minus one heteroatom, optionally substituted with at least one substituent A2; where A1 is selected from a halogen atom, a CF3 group, CN, OR, SR, NRR ', NRC (= NR') NR "R" ', COR, CSR, COOR, CONRR', CSNRR ', NRCSR ', NRCSNR'R', NRCOR ', 9. Use according to one of the preceding claims, characterized in that at least one of Ra and Rb represent a group COOR, OR, NO2, CF3, SO2NRR ', CH2COOR, a C1-C5 alkyl radical, saturated or no. 10. Use according to one of the preceding claims, characterized in that R and / or R 'represent hydrogen or a methyl radical or a pyridine group. <Desc / Clms Page number 25> 11. Use according to one of the preceding claims, characterized in that X and Y represent a CRc group. 12. Use according to one of the preceding claims, characterized in that m is an integer worth in particular 0.1 or 2. 13. Use according to one of the preceding claims, characterized in that n is an integer representing 0.1, 2.3 or 5. 14. Use according to one of the preceding claims, characterized in that the salt of the compound of formula (I) is a salt selected from sodium or potassium salts, zinc salts (Zn2 +), calcium (Ca2 +) , copper (Cu2 +), iron (Fe2 +), strontium (Sr2 +), magnesium (Mg2 +), manganese (Mn2 +), ammonium, triethanolamine salts, monoethanolamine, diethanolamine, hexadecylamine and N, N, N ', N'-tetrakis (2-hydroxypropyl) ethylene diamine, hydroxides, carbonates, halides, sulphates, nitrates, phosphates. 15. Use according to claim 14, characterized in that the salt is a sodium salt.  Embedded image Compound 2 ON OH 0-- N, N 'N- <OH 10 0-r-.a + + Compound 3 HO N 0, -N H 0

16. Use according to one of the preceding claims, characterized in that the compound of formula (1) satisfies one of the following formulas: Compound 1 <Desc / Clms Page number 26>  Compound 4 HO H: - 0 HN, NF Compound 5 0- (OH Compound 6 OH F! 1 NN 'Compound 7 0 R N F N N-0 Compound 8 J- (N "N Compound N11-- 17. Use according to one of the preceding claims, characterized in that the compound of formula (I) or a mixture of compounds of formula (I) is used at a concentration ranging from 10-3 to 10. %, preferably 10-2 to 2%, based on the total weight of the composition.

18. Use according to one of the preceding claims, characterized in that the composition is a composition for topical application. <Desc / Clms Page number 27> NRCSNR'R ", NRCOR ', NRCONR'R", SO2NRR', NRS02R ', NRS02NR'R ", SO2R, NO2, b) an alkyl radical C1-C10, linear or branched, saturated or unsaturated, optionally substituted with at least one substituent A1 or with saturated or unsaturated C1 rings containing NRC (= NR ') NR "R"', COR, CSR, COOR, CONRR ', CH2COOR, CSNRR', NRCSR ',  in which: 1) Ra and Rb, which are identical or different, are chosen from: a) a hydrogen atom, a halogen atom, a CF3, CN, OR, SR, NRR 'group,

19. Skincare or makeup composition for human keratin fibers, topically applied, containing a physiologically acceptable medium and an effective amount of at least one azo compound of formula (I) or a salt thereof, 3 to 7 atoms and / or possibly including at least one heteroatom and / or being optionally substituted by at least one substituent A2, and / or optionally contiguous to at least one C3 ring optionally including at least one heteroatom, or c) an aromatic ring C2 optionally including at least one heteroatom and / or being optionally substituted with at least one substituent A2 and / or optionally fused to at least one C3 ring optionally including at least one heteroatom; 2) X and Y, which are identical or different, represent-CRc or a nitrogen atom optionally in NO or quaternized form, Rc having the meaning of Ra or Rb, provided that X and Y do not simultaneously represent a nitrogen atom in the form of NO or quaternized; 3) n and m represent integers ranging from 0 to 5; where R, R, 'R' and R '"identical or different designate: # the hydrogen atom or a linear or branched, saturated or unsaturated C1-C10 alkyl radical, # a C2 aromatic ring optionally including minus one heteroatom, optionally substituted with at least one substituent A2; where A1 is selected from a halogen atom, a group CF3, CN, OR, SR, NRR ', NRC (= NR ') NR "R"', COR, CSR, COOR, CONRR ', CSNRR', NRCSR ', NRCSNR'R ", NRCOR ', NRCONR'R ", SO2NRR', NRSO2R ', NRSO2NR'R", SO2R, NO2;

 where A2 is chosen from linear or branched C1-C10 alkyl radicals, OR1, SR1, NR1R'1, COOR1, COR1, CH2COOR1, with R1 and R 'being identical or different and denoting hydrogen, a C1-alkyl radical; -C10, linear or branched, saturated or not; wherein the heteroatom is selected from N, O, S or Se. 20. Composition according to the preceding claim, characterized in that at least one of Ra and Rb represent a group COOR, OR, NO2, CF3, SO2NRR ', CH2COOR, a C1-C5 alkyl radical, saturated or not. 21. Composition according to claim 19 or 20, characterized in that R and / or R 'represent hydrogen or a methyl radical or a pyridine group. <Desc / Clms Page number 28>  22. Composition according to one of claims 19 to 21, characterized in that X and Y represent a CRc group. 23. Composition according to one of claims 19 to 22, characterized in that m is an integer worth in particular 0.1 or 2. 24. Composition according to one of claims 19 to 23, characterized in that n is an integer representing 0, 1, 2,3 or 5. 25. Composition according to one of claims 19 to 24, characterized in that the salt of the compound of formula (I) is a salt selected from sodium or potassium salts, zinc salts (Zn2 +), calcium ( Ca2 +), copper (Cu2 +), iron (Fe2 +), strontium (Sr2 +), magnesium (Mg2 +), manganese (Mn2 +), ammonium, the salts of triethanolamine, monoethanolamine, diethanolamine, hexadecylamine and N, N, N ', N'-tetrakis (2-hydroxypropyl) ethylene diamine, hydroxides, carbonates, halides, sulphates, nitrates, phosphates. 26. Composition according to one of claims 19 to 25, characterized in that the salt is a sodium salt.  Embedded image Compound 2 O.-N VN "# 0 OH 0 # 0 Compound Compound 0 HO: 'N" 011-bzz Compound 40, HN f N, OFF \ OH F ", 1", - cf '

27. Composition according to one of claims 19 to 26, characterized in that the compound of formula (I) satisfies one of the following formulas: Compound 1 <Desc / Clms Page number 29>  Compound 5 Compound 0 "" Compound 6 OH NN δ Compound 7 0 0 '(N "N - o Ho 1 N N Compound 8 R" C HO 1 1 N Compound 9 -J: f N "N- Composition according to one of Claims 19 to 27, characterized in that compound of formula (I) or a mixture of compounds of formula (I) is used at a concentration ranging from 10-3 to 10%. preferably from 10-2 to 2%, relative to the total weight of the composition.

29. Composition according to one of claims 19 to 28, characterized in that it is in the form of hair cream or lotion, shampoo or conditioner, hair mascara or eyelash. 30. Composition according to one of claims 19 to 29, characterized in that it is in the form of aqueous solution or suspension, alcoholic or hydro-alcoholic. 31. Composition according to one of claims 19 to 30, characterized in that it contains other ingredients chosen from solvents, thickeners or gelling agents of aqueous phase or oily phase, the dyestuffs soluble in the medium of the composition, fillers, pigments, antioxidants, preservatives, perfumes, electrolytes, neutralizers, film-forming polymers, UV blocking agents, cosmetic and pharmaceutical active agents other than the compounds of formula (1), their mixtures. 32. Composition according to one of claims 19 to 31, characterized in that it contains at least one additional active compound promoting the regrowth and / or limiting the fall of keratin fibers. <Desc / Clms Page number 30>  33. A composition according to claim 32, characterized in that the additional active agent is chosen from aminexil, 6-0 - [(9Z, 12Z) -octadeca-9,12-dienoyl] hexapyranose, lipoxygenase inhibitors, inhibitors of bradykinin, prostaglandins and their derivatives, prostaglandin receptor agonists or antagonists, nonprostanoic prostaglandin analogues, vasodilators, antiandrogens, cyclosporins and their analogues, antimicrobials, anti-inflammatories, retinoids, mention benzalkonium chloride, benzethonium chloride, phenol, estradiol, chlorpheniramine maleate, chlorophyllin derivatives, 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, substituted aryl ethenes, N-acyl amino acids, flavonoids, ascomycin derivatives and analogs, histamine antagonists, saponins, proteoglycanase inhibitors, agonists and antagonists estrogens, pseudoterines, cytokines and promoters of growth factors, inhibitors of IL-1 or IL-6, IL-10 promoters, TNF inhibitors, vitamins, benzophenones, hydantoin, retinoic acid, antipruritic agents, antiparasitic agents, antifungals, calcium antagonists, hormones, triterpenes, antiandrogens, steroidal or non-steroidal 5-a-reductase inhibitors, agonists of potassium channels, the FP receptor agonists, their mixtures. 34. Composition according to one of Claims 19 to 33, characterized in that it contains, in addition, at least one active agent chosen from proteins, protein hydrolysates, amino acids, polyols, urea allantoin, sugars and sugar derivatives, water-soluble vitamins, plant extracts, hydroxy acids, retinol, tocopherol, retinol or tocopherol derivatives, essential fatty acids, ceramides, essential oils, derivatives of salicylic acid such as 5-n-octanoylsalicylic acid, esters of hydroxy acids, phospholipids, and mixtures thereof. 35. Care or makeup composition for keratinous fibers, comprising, in a physiologically acceptable medium, in particular a cosmetic medium, at least one compound of formula (1) or one of its salts and at least one additional active agent promoting the regrowth of fibers human keratin and / or limiting their fall selected from aminexil, FP receptor agonists and vasodilators. 36. Composition according to one of claims 32,33 or 35, characterized in that the additional active agent is chosen from aminexil, minoxidil, latanoprost, butaprost and travoprost 37. Process for the cosmetic treatment of keratinous fibers and / or the skin from which said fibers emerge, characterized in that it consists in applying to said fibers and / or said skin, a cosmetic composition as defined in any one of claims 19 to 36, to leave it in contact with said fibers and / or said skin, and possibly rinsing. 38. Process for the cosmetic care and / or makeup of human eyelashes, with a view to improving their state and / or their appearance, characterized in that it consists in applying to the eyelashes and / or the eyelids a mascara composition comprising at least one compound of formula (1) or one of its salts and to leave it in contact with eyelashes and / or eyelids. 39. Process for the cosmetic care of human hair and / or scalp, with a view to improving their condition and / or their appearance, characterized in that it consists in applying to the hair and / or the scalp, a composition cosmetic composition comprising an effective amount of at least one compound of formula (I) or a salt thereof, to leave it in contact with the hair and / or the scalp, and optionally to rinse the hair and / or scalp.