WO2005107687A1

WO2005107687A1 - 2-oxy-acetamide compound, the uses thereof and compositions for stimulating or inducing the growth, and/or retarding the loss, of keratin fibres

Info

Publication number: WO2005107687A1
Application number: PCT/FR2005/000926
Authority: WO
Inventors: Roger Rozot; Philippe Breton; Michel Neuwels; Christophe Boulle
Original assignee: L'oreal
Priority date: 2004-04-22
Filing date: 2005-04-18
Publication date: 2005-11-17
Also published as: JP2007533708A; EP1763382A1

Abstract

The invention relates to the following 2-oxy-acetamide compounds, the salts and/or solvates thereof as an inhibitor of 15-PGDH, (II) (III) (IV) (V), wherein: (i) R7 and R8 represent H, halogen, CF3, CN, OR4, SR4, NHR6, NR6R'6, OCOR4, COR4, CSR4, COOR4, SO2R4, SiR4R'4R'4, OCF3, and R4, R'4, R'4, R6, R'6 represent H or an alkyl that is optionally substituted by phenyl, an optionally-substituted alkyl, a (hetero)cycle which is optionally fused to another ring; (ii) Z represents (ii); (iii) X and Y represent H or A2 or form a (hetero)cycle which is optionally substituted and/or fused to another ring; (iv) A represents (iv); (v) R3 represents an optionally-substituted alkyl, a (hetero)cycle which is optionally fused to another ring, said rings being optionally substituted; and (vi) A2 represents halogen, CF3, CN, OR4, SR4, NR4R'4, OCOR4, COR4, CSR4, COOR4, S02R4, SiR4R'4R'4, NO2, OCF3, an optionally-substituted alkyl, a (hetero)cycle which is optionally fused to another ring, where rings C11 and C12 can be substituted.

Description

2-oxy-acetamide compound, its uses and compositions for stimulating or inducing the growth of keratin fibers and / or curbing their fall FIELD OF THE INVENTION

The subject of the invention is a composition for caring for or making up keratin fibers, containing an effective amount of a 2-oxy-acetamide compound, intended to increase the density of these fibers and / or improve their appearance. More specifically, the invention relates to a composition for caring for or making up hair or eyelashes, intended to induce and / or stimulate their growth and / or slow down their fall. It also relates to new 2-oxy-acetamide compounds and to a cosmetic treatment process intended to stimulate the growth of keratin fibers and in particular of the hair and / or to curb their fall. The human keratin fibers to which the invention applies are in particular hair, eyebrows, eyelashes, beard hair, mustache hair and pubic hair. More specifically, the invention applies to human hair and / or eyelashes.

In particular, the invention relates to a composition for caring for and / or making up hair or eyelashes, for topical application, containing a 2-oxy-acetamide compound, intended to increase their density and / or their appearance. BACKGROUND OF THE INVENTION Hair growth and hair renewal are mainly determined by the activity of the hair follicles and their matrix environment. Their activity is cyclical and essentially comprises three phases, namely the anagen phase, the catagen phase and the telogen phase. The anagen phase (active or growth phase), which lasts several years and during which the hair lengthens, is followed by a very short and transient catagen phase which lasts a few weeks. During this phase, the hair undergoes an evolution, the follicle atrophies and its dermal implantation appears higher and higher.

The terminal phase or telogen phase, which lasts a few months, corresponds to a resting phase of the follicle and the hair ends up falling out. At the end of this rest period, a new follicle is regenerated on site, and another cycle begins again. The hair is therefore constantly renewed and of the approximately 150,000 hairs in hair, approximately 10% are at rest and will be replaced in a few months.

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

In addition, different causes can cause significant, temporary or permanent loss of hair. It can be hair loss and alteration during pregnancy (post partum), during states of undernutrition or food imbalances, during physiological stress or even during states of asthenia or hormonal dysfunction as may be the case during or after menopause. It can also be a question of hair loss or alterations in relation to seasonal phenomena. It can also be an alopecia, which is essentially due to a disturbance of the capillary renewal leading initially to the acceleration of the frequency of the cycles to the detriment of the quality of the hair, then of their quantity. Successive growth cycles result in increasingly thinner and shorter hair, gradually transforming into an unpigmented down. Areas are preferentially affected, in particular the temporal or frontal gulfs in men, and in women, there is a 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 the permanent, partial or general loss of hair. It is more particularly about androgenic alopecia. In a significant number of cases, early hair loss occurs in genetically predisposed subjects, it is then andro-chrono-genetic alopecia; this form of alopecia especially concerns men.

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

For many years, research has been carried out in the cosmetic or pharmaceutical industry on compositions which make it possible to suppress or reduce alopecia, and in particular to induce or stimulate hair growth or to reduce hair loss.

With this in mind, a large number of compositions have already been proposed comprising very diverse active agents, such as, for example, 2,4-diamino 6-piperidinopyrimidine 3-oxide or "minoxidil" described in US Patents 4,139,619 and US 4,596 812 or its numerous derivatives such as those described in documents EP 0353123, EP 0356271, EP 0408442, EP 0522964, EP 0420707, EP 0459890, EP 0519819.

Clinical studies have shown 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, scalp tests have shown that a prostaglandin E2 analog (viprostol) has the property of increasing hair density (Roenigk HH, 1988. Clinic Dermatol., 6 (4), 119 -121).

Furthermore, document WO 98/33497 describes pharmaceutical compositions containing prostaglandins or prostaglandin derivatives, intended to combat hair loss in humans. Prostaglandins of type A2, F2α and E2 are mentioned as preferred.

However, prostaglandins are molecules with a very short biological half-life time and acting in an autocrine or paracrine manner, this reflecting the local and labile nature of the metabolism of prostaglandins (Narumiya S. et al., 1999, Physiol. Rev., 79 (4), 1193-1226). It therefore appears to be important, in order to maintain and / or increase the capillary density in humans, to preserve the endogenous reserves of PGF2-α as of PGE2 in the various compartments of the hair follicle or of its close cutaneous environment. One solution giving good results is the administration of lipoxygenase inhibiting compounds and / or cyclooxygenase inducing agents in order to promote hair growth; one hypothesis is that the administration of such compounds directs the fatty acid metabolism 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 the prostaglandins involved in the growth and keeping the hair alive.

It is also well known that the differentiation programs of the keratinocytes of the epidermis and of 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: 35123-35132) distinct from that expressed in the epidermis, as the differentiation markers such that keratins K and K ₁₀ are not expressed in the hair follicle and in particular in the external sheath (Lenoir et al., 1988, Dev. Biol. 130: 610-620), than trichohyaline (O'Guin et al ., 1992, J. Invest. Dermatol. 98: 24-32) and keratin Kδirs (Porter et al., 2001, Br. J. Dermatol. 145: 558-568) are expressed in the hair follicle in particular in the internal sheath but not in the epidermis, and that type 1 cyclo-oxygenase, if it is expressed in the epidermis, is not expressed in the keratinocytes of the hair follicle but in the dermal papilla (Michelet. et al. , 1997, J. Invest. Dermatol. 108: 205-209).

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 determining compartment for the life of the hair. Indeed, the applicant has now proven the presence of 15-hydroxy prostaglandin dehydrogenase (15-PGDH for short) type 1 at this level. He also showed that inhibition of 15-PGDH type 1 has a beneficial effect on hair growth.

This is why the present invention relates to a hair care or treatment composition containing at least one particular inhibitor of 15-hydroxy prostaglandin dehydrogenase type 1 and a physiologically acceptable medium.

15-PGDH type 1 is a key enzyme in the deactivation of prostaglandins, in particular PGF2-α, and PGE2, which are important mediators of hair growth and survival. It meets the EC 1.1.1.141 classification and is NAD + dependent. She was isolated from pork kidney; in particular, its inhibition by a thyroid hormone, tri-iodo thyronine, has been observed at doses much higher than physiological doses. 15-PGDH type 2 is NADP dependent. However, it has never been proposed to use a 15-PGDH type 1 inhibitor to maintain and / or increase the density of human keratin fibers and in particular human hair and / or to reduce the heterogeneity of the diameters of the fibers. keratin and especially hair in humans. By increasing the density of keratin fibers, and in particular the hair density, is meant increasing the number or the diameter of keratin fibers and in particular of the hair per cm ² of skin or scalp. STATEMENT OF THE INVENTION The applicant has found that certain 2-oxy-acetamide compounds, salified or not, are surprisingly endowed with an activity favorable to improving the density of human keratin fibers. He also found that these compounds are inhibitors of 15-hydroxy prostaglandin dehydrogenase type 1. The present invention therefore relates to a composition for caring for and / or making up keratin fibers, in particular hair or mascara for topical application containing in a physiologically acceptable medium an effective amount of at least one 2-oxy-acetamide compound of formula (I) or one of its salts and / or its solvates:

in which: a) R and R ₂ are independently chosen from: 1) hydrogen, with Ri different from R ₂ , 2) a CC ₂₀ alkyl radical optionally substituted with at least one substituent AL 3) a C ¹ hydrocarbon ring of 3 to 7 atoms optionally attached to at least one C ² ring of 4 to 7 atoms, the C ² ring optionally containing at least one heteroatom to form a Hy ₂ heterocycle, these C ¹ and C ² rings optionally comprising a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent A ₂ , 4) a heterocycle Hy _! optionally attached to a C ² ring of 4 to 7 atoms, the C ² ring optionally containing at least one heteroatom to form a Hy ₂ heterocycle, these Hy-i and C ² rings possibly comprising a carbonyl or thiocarbonyl function and / or being substituted with at least one substituent Ai, 5) one of the groups C (= NR) R \ C (= NR) NR'R ", COR, CSR, COOR, CONRR ', SO ₂ R or SO ₂ NRR'; b) R ₃ is chosen from: 1) a Cι-C ₂₀ alkyl radical optionally substituted by at least one substituent AL 2) a C ³ hydrocarbon ring of 3 to 7 atoms optionally attached to at least one C ⁴ ring of 4 to 7 atoms containing optionally at least one heteroatom to form a heterocycle Hy ₄ , these cycles C ³ and C ⁴ optionally comprising a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent A ₂ , 3) a heterocycle Hy ₃ chosen from pyrrole rings , furan, thiophene and pyrazole and optionally attached to a C ⁵ ring representing a phenyl, a pyridine or a pyrimidine, the heterocycle Hy ₃ and the C ⁵ ring being optionally substituted by at least one substituent A _{1 (} 4) a heterocycle Hy ₅ different from Hy ₃ and optionally attached to a C ⁶ ring from 4 to 7 atoms, these Hy ₅ and C ⁶ rings possibly having a carbonyl or thiocarbonyl function and or being substituted by at least one substituent Ai, this C ⁶ ring optionally containing at least one heteroatom to form a Hy ₆ heterocycle; c) R, R 'and R "are independently chosen from: 1) hydrogen, 2) a CC ₂₀ alkyl radical optionally substituted with at least one substituent Ai, 3) a C ⁷ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₇ and / or being optionally joined to a C ⁸ ring of 4 to 7 atoms possibly containing at least one heteroatom to form a heterocycle Hy ₈ , the C ⁷ and C ⁸ rings being optionally substituted with at least substituent A ^ and which may contain a carbonyl or thiocarbonyl function; d) Ai is chosen from: 1) a halogen, 2) a CC ₂₀ alkyl radical optionally substituted by an OR ₅ group, 3) a C ⁹ ring of 4 to 15 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₉ and / or being optionally attached to a C ring of 4 to 7 atoms, these C ⁹ and C ¹⁰ rings optionally comprising a carbonyl or thiocarbonyl function and / or at least one substituent A ₃ chosen from OR ₅ , CF ₃ , a halogen , an alkyl radical in CC ₂ o, 4) one of the groups CF ₃ , CN, OFt ,, SR ", NF R ^, NR ₄ C (= NR ' ₄ ) NR" ₄ R'" ₄ , COR ₄ , CSR ₄ , COO ,, CONR ₄ R ' ₄ , N ^ COR', ”, NR ₄ CONR ' ₄ R" ₄ , SO ₂ NR ₄ R' ₄ , NR ₄ SO ₂ R ' ₄ , SO ₂ R ₄ , SiR4'" ₄ . If (OR ₄ ) (OR ' ₄ ) OR "_4> SO ₃ H, where R ₄ , R'_4>R" ₄ and R "" ₄ independently represent a hydrogen or a Cι-C ₂₀ alkyl radical optionally substituted by a heterocycle Hy ₁₀ or a group CONR ₅ R '₅; e) A ₂ is chosen from: 1) a halogen, 2) one of the groups CF ₃ , CN, OF, SR ₄ , NF ^ R' ^ OCOR ₄ , COR _4> CSP, COOR ₄ , SO ₂ R ₄ , SiR ₄ R 'R " ₄ , NO ₂ , OCF ₃ , where FI ,, R' ₄ and R" ₄ independently represent a hydrogen or a C ₁ -C alkyl radical ₂₀ optionally substituted by a phenyl radical, 3) a CC alkyl radical ₂₀ optionally substituted by an OR group ₅ , 4) a C ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy ^ and / or being optionally attached to a C ¹² ring of 4 to 7 atoms, these C ¹¹ and C ¹² rings can include a carbonyl or thiocarbonyl function and / or at least one substituent A ₃ chosen from OR ₅ , CF ₃ , a halogen, an alkyl radical in CC ₂₀ ; f) R ₅ and R ' ₅ are independently selected from: 1) hydrogen, 2) a CC ₂ o alkyl radical; g) Hy _{1 (} Hy ₂ , Hy ₄ to Hy ₈ , Hy ₁₀ and Hyu independently represent a heterocycle of 4 to 7 atoms which may contain from 1 to 4 heteroatoms chosen from N, O, S and their associations and / or include a function carbonyl or thiocarbonyl, h) Hy ₉ represents a heterocycle of 4 to 15 atoms which may contain from 1 to 5 heteroatoms chosen from N, O, S and their associations and / or contain a carbonyl or thiocarbonyl function.

The invention also relates to the in particular cosmetic use of at least one 2-oxy-acetamide compound of formula (I) or of one of its salts and / or of its solvates, as defined above, as agent for induce and / or stimulate the growth of keratin fibers in particular human and / or slow down their fall and / or increase their density.

It also relates to the cosmetic use of at least one 2-oxy-acetamide compound of formula (I) or of a salt and / or its solvates in a care or treatment composition for keratin fibers, in particular human fibers. to reduce their fall and / or increase their density. This composition also makes it possible to maintain the keratin fibers in good condition and / or to improve their appearance. Another subject of the invention is the use of at least one 2-oxy-acetamide compound of formula (I) or one of its salts and / or its solvates for the manufacture of a care or treatment composition for keratin fibers, especially human fibers, intended to induce and / or stimulate the growth of said fibers and / or slow down their fall and / or increase their density.

The invention also applies to keratin fibers of mammals of the animal species (dog, horse or cat for example). The human keratin fibers to which the invention applies are in particular hair, eyebrows, eyelashes, beard hair, mustache hair and pubic hair. More specifically, the invention applies to human hair and / or eyelashes.

Also, the invention also relates to the cosmetic use of at least one 2-oxy-acetamide compound of formula (I) or of one of its salts and / or of its solvates, in a cosmetic care composition. human capillary to reduce hair loss and / or increase their density and / or treat alopecia, andro-chrono-genetic.

It also relates to the use of at least one 2-oxy-acetamide compound of formula (I) or of one of its salts and / or of its solvates for the preparation of a hair composition for humans, intended inducing and / or stimulating hair growth and / or slowing hair loss and / or increasing their density and / or treating androgenic alopecia.

The invention also relates to the cosmetic use of at least one 2-oxy-acetamide compound of formula (I) or of one of its salts and / or of its solvates, in a cosmetic composition for hair care. human being to treat alopecia of natural origin and in particular androgenic as well as the use of at least one 2-oxy-acetamide compound of formula (I) or one of its salts and / or its solvates for the preparation of a hair care composition for human beings, intended for treating alopecia of natural origin and in particular androgenic. Thus, this composition makes it possible to maintain the hair in good condition and / or fight against natural hair loss and more particularly that of men.

Another subject of the invention is the cosmetic use of at least one 2-oxy-acetamide compound of formula (I) or one of its salts and / or its solvates, in a cosmetic care composition and / or for making up human eyelashes, to induce and / or stimulate the growth of eyelashes and / or increase their density, as well as the use of at least one 2-oxy-acetamide compound of formula (I) or of a its salts and / or its solvates, for the preparation of a composition for caring for or treating 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.

Another subject of the invention is the use of at least one 2-oxy-acetamide compound of formula (I) or one of its salts and / or its solvates as an inhibitor of the 15-hydroxy prostaglandin dehydrogenase type 1 including human skin. It also relates to the use of at least one 2-oxy-acetamide compound of formula (I) or of one of its salts and / or of its solvates for the manufacture of a composition intended for treating related disorders the presence of 15-hydroxy prostaglandin dehydrogenase type 1, in particular in humans. The present invention also relates to a process for the cosmetic treatment of human keratin fibers (hair or eyelashes in particular) and / or of the skin from which said fibers emerge, including the scalp and the eyelids, characterized in that it consists in applying to said keratin fibers and / or said skin, a cosmetic composition comprising at least one compound of formula (I) or one of its salts and / or its solvates, to leave it in contact with the keratin fibers and / or the skin from which said fibers emerge, and optionally rinsing said fibers and / or said skin.

This treatment process has the characteristics of a cosmetic process insofar as it makes it possible to improve the aesthetics of human keratin fibers and in particular of the hair and eyelashes by giving them greater vigor and an improved appearance. In addition, it can be used daily for several months, without 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 condition and / or their appearance, characterized in that it consists in applying to the hair and / or the scalp, a cosmetic composition comprising an effective amount of at least one compound of formula (I) or one of its salts and / or its solvates, to leave the latter in contact with the hair and / or the scalp, and possibly to rinse the hair and / or the scalp. The subject of the invention is also a method of cosmetic care and / or of making up human eyelashes, with a view to improving their condition 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 / or its solvates 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 can be removed as a conventional pigmented mascara.

A further subject of the invention is a hair or eyelash care and / or mascara composition containing a cosmetically acceptable medium and for topical application and a compound of formula (I) or one of its salts and / or its solvates.

The subject of the invention is also a composition for caring for and / or making up keratin fibers, comprising in a physiologically acceptable medium, in particular a cosmetic medium, at least one compound of formula (I) or one of its salts and / or of its solvates and at least one additional active agent promoting the regrowth of human keratin fibers and / or limiting their fall chosen from aminexil, agonists of the FP receptor, prostaglandins and their derivatives, and vasodilators and more especially chosen from aminexil, minoxidil, latanoprost, acid (5E) -7 - {(1 R, 2R, 3R, 5S) -3.5- dihydroxy-2 - [(3R) -3-hydroxy-5-phenyl pentyl ] cyclopentyl} hept-5-enoique, butaprost and travoprost.

Another subject of the invention is the cosmetic use of a 2-oxy-acetamide compound of formula (I) or of one of its salts and / or of its solvates, as an agent for preserving the quantity and / or the prostaglandin activity in the hair follicle.

Another subject of the invention is the use of at least one 2-oxy-acetamide compound of formula (I) or one of its salts and / or its solvates for the manufacture of a composition intended to preserve the amount and / or activity of prostaglandins in the hair follicle.

The subject of the invention is also new 2-oxy-acetamide compounds satisfying at least one of the formulas (II), (III), (IV) and (V) below or one of the salts and / or corresponding solvates: Formula (Ih

Formula (III)

Formula (IV)

Formula (V)

in which :

(i) R ₇ and R ₈ independently represent: 1) hydrogen, 2) halogen such as F or Cl, 3) one of the groups CF ₃ , CN, OF ^, SR ₄ , NHRe, NReR'e, OCOR ₄ , COR ₄ , CSR ₄ , COOR _4l SO ₂ R ₄ , SiR ₄ R ' ₄ R " ₄ , OCF ₃ , OÙ R ₄ , R' ₄ and R" ₄ independently represent a hydrogen or a linear or branched alkyl radical, in particular saturated , in Cι-C _2Q optionally substituted by a phenyl radical and where R ₆ and R ' ₆ represent an alkyl radical in CC ₂₀ optionally substituted by a phenyl radical, 4) an alkyl radical in C _r C ₂₀ optionally substituted by an OR group ₅ where R ₅ represents a hydrogen or a linear or branched alkyl radical, in particular saturated, in Cι-C ₂₀ , 5) a C ¹¹ ring saturated or not with 4 to 7 atoms optionally containing at least one heteroatom to form a Hyu heterocycle and / or being optionally attached to a C ¹² ring, saturated or not, from 4 to 7 atoms, these C ¹¹ and C ¹² rings may contain a carbonyl function e or thiocarbonyl; (ii) Z represents one of the following cycles and heterocycles:

(iii) X and Y independently represent a hydrogen or A ₂ as defined above (confers formula (I)) or can form a C ¹³ ring, saturated or not, saturated with 4 to 7 atoms, this C ¹³ ring optionally comprising at least one heteroatom, being optionally substituted by at least one substituent A ₂ and optionally joined to another C ¹⁴ ring, saturated or not; provided that when Z represents the dibenzofuran heterocycle, X and Y independently represent: 1) hydrogen, 2) halogen such as F and Cl, 3) one of the groups CF ₃ , CN, OR ₉ , SR ₄ , NF ^ R ', ”, OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R, SiR ₄ R'R" ₄ , NO ₂ , OCF ₃ , where F, R ' ₄ and R " ₄ independently represent hydrogen or a CC ₂ o alkyl radical, linear or branched, in particular saturated, and optionally substituted by a phenyl radical and where R ₉ represents a hydrogen or a C ₂ -C ₂₀ alkyl radical linear or branched, in particular saturated, and optionally substituted by a phenyl radical, 4) a linear or branched C ₂ -C ₂ alkyl radical, in particular saturated, and optionally substituted with an OR group ₅ , 5) a saturated or unsaturated C ¹¹ ring of 4 to 7 atoms optionally containing at least a heteroatom to form a Hyu heterocycle and / or being optionally joined to a C ¹² ring, saturated or unsaturated, from 4 to 7 atoms, these C ¹¹ and C ¹² rings which may include a carbonyl or thiocarbonyl function; or condition that when Z represents the cycle

X and Y independently represent: 1) hydrogen, in this case X different from Y, 2) fluorine, 3) one of the groups OR ₁₀ , SR ₄ , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₆ , SiR ₄ R ' ₄ R " ₄ , OCF ₃ , where R ₄ , R' ₄ and R" ₄ independently represent a hydrogen or an alkyl radical in CrC _20, linear or branched, in particular saturated, and optionally substituted by a phenyl radical, where R ₆ represents a Cι-C ₂₀ alkyl radical, linear or branched, in particular saturated, and optionally substituted by a phenyl radical and where Rio represents a hydrogen or a benzyl radical or a C ₃ alkyl radical - C ₂₀ , linear or branched, in particular saturated, and optionally substituted by a phenyl radical, 4) a C ₂ -C ₂₀ alkyl radical, linear or branched, in particular saturated, and optionally substituted by an OR group ₅ , 5) X and Y can also form a C ¹³ ring saturated or unsaturated with 5 atoms optionally containing one or two atoms of o xygene and possibly being joined to another C ¹⁴ cycle, saturated or not; (iv) A represents one of the following three groups:

(v) R ₃ has the same definition as given above for formula (I)).

Advantageously, the compounds of formula (II), (III), (IV) and (V) are inhibitors of 15-PGDH type 1 and better selective inhibitors. DETAILED DESCRIPTION OF THE EMBODIMENTS OF THE INVENTION

By 15-hydroxy prostaglandin dehydrogenase inhibitor is meant a compound of formula (I) capable of inhibiting or decreasing the activity of the 15-PGDH type 1 enzyme, in particular human, and / or capable of inhibit, decrease or slow down the reaction catalyzed by this enzyme.

According to an advantageous embodiment of the invention, the compound of formula (I) is a specific inhibitor of 15-PGDH; by specific inhibitor is meant an active which is little or no inhibitor of the synthesis of prostaglandins, in particular of the synthesis of PGF2-α or of PGE2. According to a particular embodiment of the invention, the 15-PGDH inhibitor is little or no inhibitor of prostaglandin synthesis, in particular of the synthesis of PGF2-α or of PGE2. In particular, the 15-PGDH type 1 inhibitor is little or no inhibitor of prostaglandin synthase (denoted PGF synthase or PGFS).

Indeed, the applicant has now 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 the degradation of these molecules. The exogenous supply of compounds inhibiting catabolism will therefore be less effective if this activity is combined with an inhibition of the synthesis of these prostaglandins.

Advantageously, the compounds of formula (I), in salified form or not, solvated or not, exhibit an inhibitory activity of 15-PGDH superior to the inhibitory activity of PGF synthase. These compounds are called selective 15-PGDH inhibitors over PGF synthase. In particular, the ratio between the inhibitory activities of PGF synthase and 15-PGDH respectively for a given concentration, determined in particular by the inhibitory concentration of 50% of the enzymatic activity of PGF synthase (IC _50fS ) relative to the inhibitory concentration of 50% of the enzymatic activity of 15-PGDH (IC ₅₀ d). is at least greater than 1, and in particular at least 3: 1, advantageously greater than or equal to 5: 1.

In the remainder of the text, and unless expressly stated, the use of the term compound of formula (I) must be understood to mean both the compound of formula (I) and one of its salts, of its solvates, in particular particular hydrates or one of its solvated salts (hydrated in particular). By compound salts of formula (I) is meant according to the invention, the organic or inorganic salts of a compound of formula (I). As inorganic salts which can be used according to the invention, mention may be made of the sodium or potassium salts as well as the ammonium, zinc (Zn ²⁺ ), calcium (Ca ²⁺ ), copper (Cu ²⁺ ) salts, iron (Fe ²⁺ and Fe ³⁺ ), strontium (Sr ^{2 *} ), magnesium (Mg ²⁺ ) and manganese (Mn ²⁺ ); hydroxides, halohydrates (hydrochlorides for example), carbonates, hydrogen carbonates, sulfates, hydrogen phosphates, phosphates.

The organic salts which can be used according to the invention are, for example, the salts of tri-ethanolamine, mono-ethanolamine, ethanolamine, hexadecylamine and N, N, N ', N'-tetrakis- (hydroxy-propyl-2) ethylene diamine as well as those organic acids such as citrates, lactates, glycolates, gluconates, acetates, propionates, fumarates, oxalates and tartrates. As possible solvates of the compounds of formula (I), mention may be made of hydrates, alcoholates or hydroalcoholates.

According to the invention, the compounds of formula (I) are in isolated form, that is to say non-polymeric.

"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 or Z or E isomers or a mixture of cis / trans or Z / E isomers. They can also be in tautomeric form. This or these compounds may be enantiomers and / or diastereoisomers or a mixture of these isomers, in particular a racemic mixture.

By "hydrocarbon" is meant within the meaning of the invention a group of hydrogen and carbon atoms.

By "alkyl radical" is meant within the meaning of the invention a hydrocarbon radical which can be linear or branched and saturated or unsaturated. In particular, the alkyl radical contains from 1 to 20 carbon atoms, preferably from 1 to 10. As an example of an alkyl radical which can be used in the invention, mention may be made of methyl, ethyl, isopropyl, n-butyl, fer- butyl, n-hexyl, ethyl-2-hexyl, ethylene, propylene.

As halogen atom which can be used in the invention, mention may be made of chlorine, fluorine or bromine atoms, and better still chlorine and fluorine atoms. The rings C ¹ to C ⁴ , C ⁶ to C ^{14 as} well as the heterocycles Hy _{1 (} Hy ₂ , and Hy to Hyu can be saturated or unsaturated. They contain in particular from 5 to 6 atoms. According to a particular mode of the invention, the C ⁹ ring can have up to 15 atoms and represent, for example, a crown ether having 5 -CH ₂ CH ₂ O- units. In addition, the C ¹ , C ³ , C ⁷ , C ⁹ , C rings ¹¹ , C ¹³ , Hy _{1 (} Hy ₃ , Hy ₅ , Hy ₇ , Hy ₉ , Hyu can be combined with one or more other cycles of identical or different chemical nature.

As saturated hydrocarbon rings which can 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. As combined hydrocarbon rings which can be used in the invention, mention may be made of the naphthyl, azulenyl radical. As contiguous cycles of different types which can be used in the invention, mention may be made of the benzofuran, dibenzofuran, benzothiophene, benzothiazole, indole, benzimidazole, quinoline, isoquinoline, quinazoline, carboline, chromene, carbazole, fluorene radicals. According to the invention, Ri and / or R ₂ and / or R ₃ may represent a hydrocarbon ring as defined above but also a heterocycle comprising from 1 to 4 heteroatoms chosen from N, O, S and their associations. In addition, these hydrocarbon or heterocyclic rings optionally include a carbonyl or thiocarbonyl function.

As an example of a cycle with a carbonyl or thiocarbonyl function which can be used in the invention, mention may be made of the following cycles:

According to a particular embodiment of the invention R ₁ and / or R ₂ represent a heterocycle Hyi chosen in particular from: azetidine, pyrrole, dihydropyrrole, pyrrolidine, furan, dihydrofuran, tetrahydrofuran, thiophene, dihydrothiophene, tetrahydrothiophene, imidazole, dihydroimidazole , dihydrothiazole, thiazolidine, dihydropyrazole, pyrrazolidine, oxazole, dihydrooxazole, oxazolidine, isoxazole, dihydroisoxazole, isoxazolidine, isothiazole, dihydroisothiazole, isothiazolidine, triazole, dihydrotriazole, triadolid dihydradiazole, triazolidine, diadiazide, , tetrahydropyridine, piperidine, pyran, dihydropyran, tetrahydropyran, pyrimidine, dihydropyrimidine, tetrahydropyrimidine, piperazine, pyridazine, pyrazine, triazine, morpholine, azepine, diazepine. In particular, that Hy _! represents a γ-butyrolactone, a piperidine, a 1,3-benzodioxole optionally substituted by a linear or branched alkyl radical, in particular saturated with C ₁ -C ₄ . Advantageously, Ri represents hydrogen and R ₂ represents one of the following groups: - a saturated C 10 or linear C 10 alkyl radical, such as a methyl, ethyl, butyl, propyl, pentyl, hexyl radical, optionally substituted by one or two substituents AL - a saturated hydrocarbon ring of 3 to 6 carbon atoms, - a heterocycle Hyi saturated or not with 5, 6 or 7 atoms, comprising from 1 to 2 heteroatoms chosen from O, N and S and optionally a carbonyl function and / or from one to four substituents A ' ₂ , - a phenyl ring optionally substituted by one or two substituents A " ₂ chosen from a halogen (fluorine or chlorine in particular), NO ₂ , OCF ₃ , CF ₃ , OR ₄ , OCH ₂ R ₄ , COOR ₄ , an alkyl radical in C Cι _{0 in} particular saturated (such as ethyl, propyl, tert-butyl, hexyl or methyl), an aromatic hydrocarbon or heterocyclic ring, - a phenyl ring joined to one or two hydrocarbon or heterocyclic rings , saturated or not, d e 5 to 6 atoms, thus forming condensed rings such as indane, carbazole, benzodioxole, fluorene, dibenzofuran. According to the invention, the substituents Ai or A ₂ carried by the same ring or the same alkyl radical can be identical or different. In addition, they can be identical or different for Ri, R ₂ and R ₃ . Likewise, the radicals R ₄ ,, R ', R "and R'" ₄ may be identical or different for the same group, the same radical or from a substituent A ^ to a substituent A ₂ . In particular, Ai represents a hydrocarbon ring or a heterocycle comprising 1 to 2 heteroatoms chosen from O and N, this hydrocarbon or heterocyclic ring having 5 or 6 atoms and optionally a carbonyl function and / or a substituent A ₃ ; or a group chosen from SiR ₄ R ' ₄ R " _4. COOR ,, NR ₄ R' _4l OR ₄ , SR ₄ , CONR ₄ R ' _4. According to a particular embodiment of the invention, R, R' ₄ , R " ₄ and R '" ₄ represent a hydrogen, a phenyl radical or an alkyl radical in CC ₁₀ such as a methyl, ethyl, ter-butyl, n-butyl, n-butyl, n-propyl, isopropyl or pentyl radical.

Advantageously, A ′ ₂ represents a linear or branched alkyl radical, in particular saturated with C Cι ₀ such as methyl.

According to a particular embodiment of the invention, A ₃ represents a linear or branched alkyl radical in particular saturated with CC ₁₀ such as methyl, CF ₃ , a halogen atom such as F, OH or OCH ₃

According to a particular embodiment of the invention R ₃ represents a heterocycle Hy ₅ chosen from: azetidine, dihydropyrrole, pyrrolidine, dihydrofuran, tetrahydrofuran, dihydrothiophene, tetrahydrothiophene, imidazole, dihydroimidazole, imidazolidine, thiazole, dihydrothiazole, thiazole oxazole, dihydro-oxazole, oxazolidine, isoxazole, dihydro-isoxazole, isoxazolidine, isothiazole, dihydro-isothiazole, isothiazolidine, triazole, dihydrotriazole, triazolidine, oxadiazole, dihydro-oxadiazole, tyradidiazide, thiadiazolidine, thiadiazolidine piperidine, pyran, dihydropyran, tetrahydropyran, pyrimidine, dihydropyrimidine, tetrahydropyrimidine, piperazine, pyridazine, pyrazine, triazine, morpholine, azepine, diazepine.

Advantageously, R ₃ represents one of the following groups: - a saturated or unsaturated hydrocarbon ring, optionally substituted by one or more substituents A '" ₂ chosen from a phenyl radical, COOR ₄ , OR, COR ₄ , CN, a heterocycle with 5 or 6 saturated or unsaturated atoms comprising from 1 to 2 heteroatoms chosen from O, S and N as pyrrole or imidazole, a halogen (fluorine or chlorine), a phenyl radical optionally substituted by CN, a linear or branched Cι- alkyl radical C _{10 in} particular saturated as ethyl, methyl, isopropyl, isobutyl, ter-butyl, with R ₄ representing a hydrogen or a linear or branched alkyl radical in CrC _{10 in} particular saturated as methyl or ethyl, - a phenyl ring joined to one or two rings C ⁴ hydrocarbon or heterocyclic, saturated or unsaturated, of 5 to 6 atoms, the C ⁴ ring or rings optionally comprising a carbonyl function and / or being optionally substituted by a linear or branched alkyl radical é in CC _{10, in} particular saturated as methyl or ethyl, this phenyl ring joined to this or these C ⁴ cycles, thus forming condensed cycles such as indane, benzothiazole, quinoline, carbazole, fluorene, fluorenone, dibenzofuran, - an alkyl radical linear or branched in CrCio, in particular saturated as methyl, optionally substituted by one or two substituents Ai such as a phenyl radical. As an example of the heterocycles Hy _2l Hy, Hy ₆ , Hy ₇ , Hy ₈ , Hy ₉ , Hy ₁₀ and Hyu which can be used in the invention, mention may be made independently of the azetidine, pyrrole, dihydropyrrole, pyrrolidine, furan, dihydrofuran, tetrahydrofuran rings. , thiophene, dihydrothiophene, tetrahydrothiophene, imidazole, dihydro-imidazole, imidazolidine, thiazole, dihydrothiazole, thiazolidine, pyrazole, dihydropyrazole, pyrazolidine, oxazole, dihydro-oxazole, isazazine isole, isoxazole isiazole, isoxazole , triazole, dihydrotriazole, triazolidine, oxadiazole, dihydro-oxadiazole, oxadiazolidine, thiadiazole, dihydrothiadiazole, thiadiazolidine, tetrazole, pyridine, dihydropyridine, tetrahydropyridine, piperidine, pyran, dihydropyran, tetrahydropyran, pyrimidine, dihydropyrimidine, tetrahydropyrimidine, piperazine, pyridazine, pyrazine, triazine, morpholine, azepine, diazepine or crown ether 15-C-5 for Hy ^. Preferably, use is made of the pyrrole, pyrrolidine, imidazole, furan, thiophene, oxazole, thiazole, isoxazole, isothiazole, oxadiazole, pyrazole, tetrazole, pyridine, pyrimidine, triazole, pyrazine, pyridazine, piperidine, piperazine, morpholine or even ether rings. crown 15-C-5 for Hy ₉ .

According to a preferred embodiment of the invention, the 2-oxy-acetamide compounds satisfy the following formula (1a) or one of its salts and / or one of its solvates:

in which: α) Ru is chosen from: 1) a linear or branched C Cιo alkyl radical, in particular saturated and optionally substituted with at least one substituent A ₄ , 2) a C ¹⁵ hydrocarbon ring, saturated or not, of 5 to 6 atoms optionally substituted with at least one A ₅ substituent; β) R ₂ is chosen from: 1) a linear or branched CC ₁₀ alkyl radical, in particular saturated and optionally substituted with at least one substituent A ₄ , 2) a saturated or unsaturated C ¹⁶ hydrocarbon ring of 5 to 6 atoms optionally attached to at least one saturated or unsaturated C ¹⁷ ring of 5 to 6 atoms optionally containing at least one heteroatom to form a Hy ₁₇ heterocycle, these C ¹⁶ and C ¹⁷ rings optionally comprising a carbonyl function and / or being substituted by at least one substituent A ₅ ; γ) A ₄ is chosen from: 1) a C ¹⁸ ring, saturated or not, of 5 to 6 atoms optionally containing at least one heteroatom to form a Hyι ₈ heterocycle, this cycle or this heterocycle being optionally substituted by at least one Ag substituent chosen among OR ₁ , CF ₃ , a halogen such as fluorine and chlorine, a linear or branched CC ₁₀ alkyl radical, in particular saturated; 2) one of the groups CF ₃ , CN, OR ₁₃ , SRι ₃ , NR ₁₃ R _'13 , NRι ₃ C (= NR' ₁₃ ) NR " ₁₃ R"_'13 , COR ₁₃ , COOR ₁₃ , CONR ₁₃ R' ₁₃ , NR ₁₃ COR _'13 , NR ₁₃ CONR' ₁₃ R " ₁₃ , SO ₂ NR ₁₃ R _'13 , NR ₁₃ SO ₂ R' ₁₃ , SO ₂ Rι ₃ , SiRι ₃ R'ι ₃ R" ₁₃ , SO ₃ H , where R ₁₃ , R ' _13l R " ₁₃ and R'" ₁₃ independently represent a hydrogen or a linear or branched Cι-C ₁₀ alkyl radical, in particular saturated; δ) A ₅ is chosen from: 1) a halogen such as fluorine and chlorine, 2) one of the groups CF ₃ , CN, OR ₁₅ , SR ₁₅ , NR ₁₅ R _'15 , OCOR _15l COR ₁₅ , COOR ₁₅ , SO ₂ R ₁₅ . SiR ₁₅ R'i5R "i5, NO ₂ , OCF _3> where R ₁₅ , R _'15 and R" ₁₅ independently represent a hydrogen or a linear or branched alkyl radical in particular saturated with CC ₁₀ optionally substituted by a phenyl radical, 3) a linear or branched alkyl radical in particular saturated with CrC ₁₀ optionally substituted by a group ORι ₄ , 4) a C ¹⁹ ring saturated or not with 5 to 6 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₁₉ and / or possibly comprising a carbonyl function; ε) R ₁₄ is chosen from: 1) hydrogen, 2) a linear or branched alkyl radical, in particular saturated with CrC; η) Hyι ₇ , Hyι ₈ , and Hy ₁₉ independently represent a heterocycle of 5 to 6 atoms which may contain from 1 to 4 heteroatoms chosen from N, O, S and their associations and / or contain a carbonyl function.

According to a preferred embodiment of the invention, the 2-oxy-acetamide compounds satisfy one of the following formulas (II) to (V) or one of the corresponding salts and / or solvates:

Formula (II):

Formula (III)

Formula (IV)

Formula (V)

in which: (i) R7 and R8 independently represent: 1) hydrogen, 2) halogen F or Cl, 3) one of the groups CF ₃ , CN, OFl ,, SR ₄ , NHR ₆ , NR ₆ R ' ₆ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR ₄ R ' ₄ R " ₄ , OCF ₃ , where R ₄ , R' ₄ and R" ₄ represent independently hydrogen or a d-do alkyl radical optionally substituted by a phenyl radical and where Re and R ' ₆ represent a Cι-C ₂₀ alkyl radical optionally substituted by a phenyl radical, 4) a Cι-C ₂₀ alkyl radical optionally substituted by an OR ₅ group where R5> represents a hydrogen or a dC ₂₀ alkyl radical, 5) a C ¹¹ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a Hyu heterocycle and / or possibly being joined to a C ¹² ring of 4 to 7 atoms, these C ¹¹ and C ¹² rings possibly comprising a carbonyl or thiocarbonyl function; (ii) Z represents one of the following cycles and heterocycles:

(iii) X and Y independently represent a hydrogen or A ₂ as defined above for formula (I) or can form a C ¹³ ring joined from 4 to 7 atoms and better still from 5 to 6 atoms, optionally comprising at least one heteroatom chosen from N, O, S and their associations, and being optionally substituted by one or more substituent A ₂ , and optionally attached to another C ¹⁴ ring; provided that: - when Z represents the dibenzofuran heterocycle, X and Y independently represent: 1) hydrogen, 2) halogen (Fou Cl), 3) one of the groups CF ₃ , CN, OR ₉ , SR ₄ , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR ₄ R' ₄ R " ₄ , NO ₂ , OCF ₃ , where R, R ' ₄ and R" ₄ independently represent a hydrogen or a CC ₂ o alkyl radical optionally substituted by a phenyl radical and where R ₉ represents a hydrogen or a C ₂ -C ₂₀ alkyl radical optionally substituted by a phenyl radical, 4) a C ₂ -C ₂₀ alkyl radical optionally substituted by an OR group ₅ , 5) a C ring of 4 to 7 atoms optionally containing at least one heteroatom to form a Hyu heterocycle and / or being optionally joined to a C ¹² ring of 4 to 7 atoms, these C ¹¹ rings and C ¹² may have a carbonyl or thiocarbonyl function; or that when Z represents the cycle:

X and Y independently represent: 0 1) hydrogen, in this case X is different from Y 2) fluorine, 3) one of the groups OR ₁₀ , SR ₄ , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COORe, SiR ₄ R 'R " ₄ , OCF ₃ , where R ₄ , R' ₄ and R" independently represent a hydrogen or an alkyl radical in dC ₂₀ optionally substituted with a phenyl radical, where Rβ represents an alkyl radical in dC ₂₀ optionally substituted by a phenyl radical and where R ₁₀ represents a hydrogen or a benzyl radical or a C ₃ -C ₂₀ alkyl radical optionally substituted by a phenyl radical, 4) a C ₂ -C ₂₀ alkyl radical optionally substituted by an OR ₅ , 5) group X and Y can also form a C ¹³ ring with 5 links (or atoms), saturated or not and optionally containing one or two oxygen atoms and possibly being joined to another C ¹⁴ ring, saturated or not;

(iv) A represents one of the following three groups:

(v) R ₃ has the same meaning as given for formula (I).

Furthermore, cycles C ¹¹ and C ¹² have the same meaning as above.

To the knowledge of the applicant, no document of the prior art describes or suggests that the 2-oxy-acetamide compounds of formula (I) or their salts and / or their solvated forms have the property of inducing and / or stimulate the growth of human keratin fibers and in particular human hair and eyelashes and / or slow their fall, or that these compounds can be used topically to increase the density of keratin fibers (hair and eyelashes in particular).

The effective quantity of a compound of formula (I) (salified or not, solvated or not) corresponds to the quantity necessary to obtain the desired result (namely to increase the density of keratin fibers and in particular of hair and eyelashes or to promote their shoot). Those skilled in the art are therefore able to assess 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 following 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) (salified or not, solvated or not) or a mixture of compounds of formula (I) and / or their salts can be used in an amount 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 can 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 which is non-toxic and capable of being applied to the skin, including the scalp and the eyelids, and to the keratin fibers of human beings. By "cosmetic" is meant within the meaning of the invention a composition of pleasant appearance, odor and feel. The compound of formula (I), salified or not, solvated or not, can be used in a composition which must be ingested, injected or applied to the skin or to the keratin fibers (on any skin area or fibers to be treated). According to the invention, the compound of formula (I) or a mixture of compounds of formula (I) can be used orally in an amount of 0.1 to 300 mg per day, in particular from 5 to 10 mg / d. A preferred composition of the invention is a composition for cosmetic use and in particular for topical application to the skin and keratin fibers, and more especially to the scalp, hair and eyelashes.

This composition can be in any known dosage form adapted to the mode of use.

For topical application to the skin or keratin fibers, the composition may be in the form of an aqueous, alcoholic or hydroalcoholic solution or suspension or of an oily suspension or solution, of an emulsion or dispersion of more or less consistency. less fluid and in particular liquid or semi-liquid, obtained by dispersion of a fatty phase in an aqueous phase (O / W) or vice versa (W / O), of a solid emulsion or dispersion (O / W) or (E / H), a more or less fluid or solid aqueous, hydro-alcoholic or oily gel, a free or compacted powder to be used as it is or to be incorporated in a physiologically acceptable medium, or alternatively microcapsules or microparticles, Ionic and / or nonionic type vesicular dispersions.

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

It can thus be in the form of a lotion, serum, milk, O / W or W / O cream, gel, ointment, ointment, powder, balm, patch, soaked tampon, bread, mousse.

In particular, the composition for application to the scalp or the hair may be in the form of a hair care lotion, for example of daily or bi-weekly application, of a shampoo or of a hair conditioner, in particular bi-weekly or weekly application, a liquid or solid soap for cleaning the scalp of daily application, a product for shaping the hairstyle (hairspray, product for styling, styling gel ), a treating mask, a foaming cream or gel for cleaning the hair. It can also be in the form of a hair dye or mascara to be applied by brush or comb.

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

For a composition for use by injection, 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, drinkable syrups or tablets. According to a particular embodiment, the composition according to the invention is in the form of a hair cream or lotion, hair shampoo or conditioner, hair mascara or for eyelashes. 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 can 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 fatty phase and of 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 can contain fatty or oily compounds, liquid at room temperature (25 ° C) and atmospheric pressure (760 mm Hg), 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 can, in addition to oils, contain waxes, gums, lipophilic polymers, "pasty" or viscous products containing solid parts and liquid parts.

The aqueous phase contains water and optionally an ingredient miscible in any proportion with water, such as lower alcohols, C 1 to C ₈ such as ethanol, isopropanol, polyols such as propylene glycol, glycerol, sorbitol or acetone or ether.

The emulsifiers and coemulsifiers used to obtain a composition in the form of an emulsion are generally used in the cosmetic and pharmaceutical fields. Their nature is, moreover, a function of the direction 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% . The emulsion can, in addition, contain lipid vesicles and in particular liposomes. When the composition is in the form of an oily solution or gel, the fatty phase can represent more than 90% of the total weight of the composition.

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

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

The composition of the invention may also comprise other additional ingredients usually used in the fields concerned, chosen from solvents, thickeners or gelling agents of aqueous phase or of oily phase, coloring matters soluble in the medium of the composition, solid particles such as fillers or pigments, antioxidants, preservatives, perfumes, electrolytes, neutralizers, film-forming polymers, UV blocking agents such as sunscreens, cosmetic and pharmaceutical active agents with beneficial action for the skin or keratin fibers, other than the compounds of formula (I), their mixtures. These additives can be present in the composition according to the quantities generally used in the cosmetic and dermatological field and in particular at a rate of 0.01 to 50% of the total weight of the composition and better still from 0.1 to 20% and for example of 0 , 1 to 10%. These additives, depending on their nature, can be introduced into the fatty phase, into the aqueous phase and / or into the lipid vesicles and in particular liposomes. Of course, the person skilled in the art will take care to choose any additional ingredients and / or their amount in such a way that the advantageous properties of the composition according to the invention, namely the inhibition of type-15-PGDH and in particular the 'increase in the density of keratin fibers, are not or substantially not, altered by the planned addition.

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

As oils which can be used in the invention, mention may be made of oils of mineral origin (petrolatum 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, candellila, carnauba or paraffin, polyethylene.

As emulsifiers which can be used in the invention, mention may, for example, be made of glycerol stearate or laurate, sorbitol stearates or oleates, alkyl dimethiconecopolyol (with alkyl> 8) and their mixtures for a W / O emulsion. Polyethylene glycol monostearate or monolaurate, polyoxyethylenated sorbitol stearate or oleate, dimethiconecopolyols and their mixtures can also be used for an O / W emulsion.

As hydrophilic gelling agents which can be used in the invention, mention may be made of carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkyl acrylate 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, their mixtures.

As cosmetic or pharmaceutical active agent, other than the compounds of formula (I), which can be used in the invention, mention may be made of hydrophilic active agents such as proteins or protein hydrolysates, amino acids, polyols, urea, allantoin, sugars and sugar derivatives, water-soluble vitamins, plant extracts (those of Iridaceae or soybeans) and hydroxy acids such as fruit acids or salicylic acid; and lipophilic active agents, such as retinol (vitamin A) and its derivatives, in particular esters (retinol palmitate), tocopherol (vitamin E) and its derivatives, in particular esters (tocopherol acetate), essential fatty acids, ceramides, oils essential, salicylic acid derivatives such as 5-octanoyl salicylic acid, hydroxy acid esters, phospholipids such as lecithin, mixtures thereof. According to a particular embodiment of the invention, it is possible to combine with the compound of formula (I) or one of its salts and / or its solvates, additional compounds which promote regrowth and / or limit the fall of the fibers. keratin (hair, eyelashes). These additional compounds are in particular chosen from lipoxygenase inhibitors as described in EP 648488, bradykinin inhibitors described in particular in EP 845700, prostaglandins and their derivatives in particular those described in WO 98/33497, WO 95/11003, JP 97- 100091, JP 96-134242, prostaglandin receptor agonists or antagonists, non-prostanoic analogs prostaglandins 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 promoting the growth of keratin fibers and / or limiting their fall (in particular the hair or the eyelashes) which may be present in the composition according to the invention, mention may be made of vasodilators, antiandrogens, cyclosporins and their analogs, antimicrobials and antifungals, anti-inflammatories, retinoids, alone or in a mixture. The vasodilators which can be used are in particular the potassium channel agonists including minoxidil, as well as the compounds described in US Pat. diaxozide, alone or in combination. The antiandrogens which can be used in particular include the steroidal or nonsteroidal inhibitors of 5α-reductase, such as finasteride and the compounds described in US 5 516779, cyprosterone acetate, azelaic acid, its salts and its derivatives and the compounds described in US 5,480,913, flutamide, oxendolone, spironolactone, diethylstilbestrol and the compounds described in US patents 5,411,981, 5,565,467 and 4,910,226.

The antimicrobial or antifungal compounds can be chosen from selenium derivatives, octopirox, triclocarban, triclosan, pyrithione zinc, itraconazole, asian acid, hinokitiol, mipirocin, tetracyclines, in particular the erythromycin and the compounds described in EP 0680745, clinycin hydrochloride, benzoyl or benzyl peroxide, minocycline and the compounds belonging to the imidazole class such as econazole, ketoconazole or miconazole or their salts, esters nicotinic acid, including in particular tocopherol nicotinate, benzyl nicotinate and C ^ C _g alkyl nicotinates such as methyl or hexyl nicotinates.

The anti-inflammatory drugs can be chosen from steroidal anti-inflammatory drugs such as glucocorticoids, corticosteroids (for example: hydrocortisone) and non-steroidal anti-inflammatory drugs such as glycyrrhetinic acid and α-bisabolol, benzydamine, salicylic acid and the compounds described in EP 0770399, WO 94/06434 and FR 2 268523.

The retinoids can be chosen from isotretinoin, acitretin, tazarotene, retinal and adapalene.

As other additional active compounds for promoting the growth and / or limiting the fall of keratin fibers such as the hair and the eyelashes, which can be used in combination with the compound of formula (I), salified or not, solvated or not, mention may be made of aminexil, 6-0 - [(9Z, 12Z) -octadeca-9,12-dienoyl] 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 ethylenes, N-acylated amino acids, flavonoids, ascomycin derivatives and analogs, histamine antagonists, saponins, i proteoglycanase inhibitors, estrogen agonists and antagonists, pseudoterins, cytokines and growth factor promoters, IL-1 or IL-6 inhibitors, promoters IL-10, TNF inhibitors, benzophenones and hydantoin, retinoic acid; vitamins such as vitamin D, analogs of vitamin B12, 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; antiparasitics, in particular metronidazole, crotamiton or pyrethroids; calcium antagonists, such as cinnarizine, diltiazem, nimodipine, verapamil, alverine and nifedipine; hormones such as estriol or its analogs, thyroxine and its salts, progesterone; FP receptor agonists (prostaglandin type F receptor) such as latanoprost, (5E) -7 - {(1 R, 2R, 3R, 5S) -3,5-dihydroxy-2 - [(3R ) -3- hydroxy-5-phenyl pentyl] cyclopentyl} hept-5-enoic, bimatoprost, travoprost, unoprostone and butaprost; their mixtures.

Advantageously, the composition according to the invention comprises at least one 15-PGDH inhibitor 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 PGE2 in the form saline or ester (eg isopropyl esters), their derivatives such as 16.16 dimethyl PGE2, 17 phenyl PGE2, 16.16 dimethyl PGF2-α, 17 phenyl PGF2-α prostaglandins of series 1 such as deoxy 11 prostaglandin E1, the 1 deoxy prostaglandin E1 in saline or ester form, their analogs in particular latanoprost, acid (5E) -7 - {(1R, 2R, 3R, 5S) -3.5- dihydroxy-2 - [( 3R) -3-hydroxy-5-phenylpentyl] cyclopentyl} hept-5-enoique, viprostol, bimatoprost, cloprostenol travoprost, fluprostenol, cloprostenol, butaprost, unoprostone, misoprostol, their salts or their salts 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 (I), salified or not, solvated or not, is in liposome form, as especially described in document WO 94/22468. Thus, the compound encapsulated in the liposomes 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 to the hair of an individual, and optionally left in contact for several hours and optionally rinsed.

One can, for example, apply the composition containing an effective amount of a compound of formula (I), salified or not, solvated or not, in the evening, keep it in contact overnight and possibly perform a shampoo in the morning . These applications can be renewed daily for one or more months depending on the individual.

Advantageously, in the method according to the invention, there are applied to the areas to be treated or treated the scalp between 5 and 500 μL of a solution or composition as defined above, comprising from 0.001% to 5% of inhibitor of the 15-PGDH. We will now give, by way of illustration, exemplary embodiments of the invention which cannot in any way limit its scope. EXAMPLES As examples of 2-oxy-acetamide compounds of formula (II) according to the invention, mention may be made of the following compounds: Compound 1

Lineups

As examples of 2-oxy-acetamide compounds of formula (III) according to the invention, mention may be made of the following compounds:

Compound 4

Compound 5

Compound 6

Compound 7

Compound 9

Compound 10

Compound 11

Compound 12

Compound 13

As examples of 2-oxy-acetamide compounds of formula (IV) according to the invention, mention may be made of the following compounds:

Compound 14

Compound 15

Compound 16

As examples of 2-oxy-acetamide compounds of formula (V) according to the invention, mention may be made of the following compounds:

Compound 17

Compound 19

According to another embodiment of the invention, the 2-oxy-acetamide compounds satisfy one of the following three formulas:

Compound 20

Compound 21

Compound 22

The compounds of formula (II), (III), (IV) and (V) as well as compounds 20, 21 and 22 are new.

The other compounds to which the invention applies are known as such. They can be manufactured in a known manner.

The compounds of formula (I) to which the invention applies, whether they are new or known, can be synthesized according to the following reaction scheme: Step 1 :

Etaoe 2: R

The operating conditions (solvent, base, temperature) for synthesis of the compounds of formula (I) depend on the starting reagents. As other examples of 2-oxy-acetamide compounds of formula (I), which can be used in the invention, mention may be made of the following compounds: Compound 23

Compound 24

Compound 26

Compound 27

Compound 28

Compound 29

Compound

Compound 32

Compound 33

Compound 35

Advantageously, the compounds to which the invention applies are compounds 2, 3, 5, 6, 8, 9, 10, 12, 13, 18, 19, 21, 23, 24, 28, 32, 34, 35 and in particular to the new compounds 2, 3, 5, 6, 8, 9, 10, 12, 13, 18, 19, 21, and to the compounds 23 and 24. Preferably, the compounds to which the invention applies are the new compounds 2, 3, 12, 13 and 21 as well as compounds 23 and 24.

We will now give, by way of illustration and without limitation, examples of synthesis of compounds in accordance with the invention which cannot in any way limit its scope.

EXAMPLE 1 Reaction scheme for the synthesis of compound 21:

1) NaH, anhydrous DMF 5 hours at 60 ° C

Operating mode

0.63 mL of freshly distilled cyclohexanol (6 mmol) is introduced into a three-necked flask under a stream of argon and diluted in 10 mL of anhydrous DiMéhtylFormamide. Sodium hydride at 60% (0.24 g; 6 mmol) is added in small portions to the reaction medium. The reaction mixture is then stirred at room temperature for 1 hour and then a solution of N-benzyl-2-chloroacetamide (1 g; 5.44 mmol) in 10 ml of anhydrous DMF is added thereto. The medium is brought to a temperature of 60 ° C for 5 hours. The reaction mixture is concentrated to the maximum and then diluted with 100 mL of dichloromethane. The organic phase is washed with water (2 times 50 mL) and then with a saturated sodium chloride solution. The organic phase is dried over sodium sulfate, filtered and then concentrated to the maximum. The crude is taken up in the minimum amount of ethyl ether and stirred for 30 minutes. The solid is removed and the filtrate purified on silica gel (eluent: dichloromethane). After distilling off the solvent and drying under vacuum in the presence of phosphorus pentoxide, a beige solid (0.36 g, with a yield (Yield) of 24%) is obtained.

The analyzes of the product (Nuclear Magnetic Resonance and Mass Spectrum) are in accordance with formula 21.

EXAMPLE 2 Reaction scheme for the synthesis of compound 22

NaH, anhydrous DMF 7 hours at 60 ° C

Operating mode

0.7 ml of anhydrous hexanol (5.44 mmol) is diluted in 20 ml of anhydrous DMF in a 50 ml three-necked flask fitted with a condenser, a thermometer and under nitrogen flow. Sodium hydride at 60% (0.24 g; 6 mmol) is added in small portions to the reaction medium. After addition, the reaction mixture is stirred at room temperature for 2 hours and then the solution of N-benzyl-2-chloroacetamide (1 g; 5.44 mmol) in 10 ml of anhydrous DMF is added. The medium is brought to a temperature of 60 ° C for 7 hours. The reaction mixture is concentrated to the maximum and then diluted with 100 ml of dichloromethane. The organic phase is washed with water (2 times 50 mL) and then with a saturated sodium chloride solution. The organic phase is dried over sodium sulfate, filtered and then concentrated to the maximum. The crude is taken up in the minimum amount of ethyl ether and stirred for 30 minutes. The solid is removed and the filtrate purified on silica gel (eluent: dichloromethane). After evaporation of the solvent and drying under vacuum, a yellow oil is obtained. (18.5 mg, Yield = 2%).

The analyzes of the product (R.M.N. and Mass Spectrum) are in accordance with those expected for compound 22.

EXAMPLE 3 Reaction scheme for the synthesis of compound 23:

Compound 23 is prepared in two stages. Step 1: Synthesis of chloroacetamide (a)

bc 40 ml of furfurylamine (c), 500 ml of dichloromethane and 69.9 ml of triethylamine (denoted Et ₃ N) are introduced into a three-necked bottle. After the reaction medium has cooled to 10 ° C., 37.1 ml of chloroacetyl chloride (b) diluted in 100 ml of dichloromethane are added dropwise while maintaining the temperature below 15 ° C. The reaction medium is then stirred for 3 h at room temperature; water is then added. The organic phase is washed with water (2 times, 100mL), then with a 1N dilute hydrochloric acid solution (2 times, 50 mL), again with water, then with a saturated solution of sodium chloride. The organic phase is dried over sodium sulphate then filtered and concentrated to give 66 g of a brown solid (compound a, yield = 84%).

Product analysis (a)

Mass spectrometry (MS): The quasi-molecular ions (MH) ⁺ , (MNa) ⁺ of the expected molecule C ₇ H ₈ CINO ₂ are mainly detected.

Nuclear Magnetic Resonance (NMR): ¹ H (DMSO, 400MHz) δ ppm: 8.66 (1 H, extended s, NH); 7; 58 (1H, dd, H _ar ); 6.40 (1H, dd, H _ar ); 6.27 (1H, dd, H _ar ); 4.30 (2H, d,

CH ₂ ); 4.09 (2H, s, CH ₂ ). s widened = widened singlet d = doublet dd = doublet of doublet

These results are in accordance with the formula of compound (a). Step 2: synthesis of compound 23 ((2- (3-Chloro-ohenoxy) -N-furan-2-ylmethyl- acetamide

d 2- (3-Chloro-phenoxy) -N-furan-2-ylmethyl-acetamide Compound 23

1 g of 3-chlorophenol (d), 20 ml of trihydrofuran (THF) and 1.9 g of cesium carbonate are introduced into a three-necked bottle under argon. A solution of 1.34 g of compound (a) previously prepared in 20 ml of dichloromethane (THF) is then added. The organic medium is brought to reflux for 5 h; water is then added. The organic phase is washed with water (2 times, 100 ml), with a 1N diluted sodium hydroxide solution (2 times, 50 ml), again with water (2 times, 100 ml), then with saturated sodium chloride solution. The organic phase is dried over sodium sulphate then filtered and concentrated to give 1.5 g of a light brown solid (compound 23, yield = 73%).

Analysis of the product obtained: NMR: ¹ H (DMSO, 400MHz) δ ppm: 8.59 (1 H, t, NH); 7.56 (1H, sc, Har); 7.32 (1H, m, Har); 7.04 (1H, d, Har); 7.02 (1H, dd, Har); 6.94 (1H, dd, Har); 6.38 (1H, m, Har);

6.21 (1H, m, Har); 4.57 (2H, s, CH ₂ ); 4.33 (2H, d, CH ₂ ). s = singlet s widened = widened singlet d = doublet dd = doublet of doublet t = triplet m = multiplet Har = aromatic hydrogen Mass spectrometry: The quasi-molecular ion (MH) ⁺ of the expected molecule 5 C ₁₃ H ₁₂ CINO ₃ is mainly detected. These results are in agreement with the formula of compound 23.

10 EXAMPLES 4. 5 and 6: Reaction scheme for the synthesis of compounds 24, 25 and 26: These compounds were produced according to the same process as compound 21 by replacing cyclohexane with phenol respectively for compound 24, 3- 15 chlorophenol for compound 25 and with 4-chlorophenol for compound 26. The mass spectra (ESU + and -) are in accordance with the expected structures.

EXAMPLES 7. 8 and 9: Reaction scheme for the synthesis of compounds 1, 2 and 3 of general formula (II): Reaction scheme for the synthesis of compound 1:

' ^y N- (2,6-Dimethyl-phenyl) -2- (quinolin-8-yloxy) -acetami e

-, - compound 1

Procedure

A suspension of 28 mg of potassium carbonate in 1 ml of acetone is introduced into a reaction tube fitted with a magnetic bar. A solution of 6.4 mg of 8-hydroxy quinoline (CAS: 148-24-3; Fluka reference: F55080) in 0.5 mL of acetone and a solution of 7.9 mg of 2-chloro-2 ', 6'-aceto-xylidide (CAS: 1131-01-7) in 0.5 mL of acetone are then added. The medium is diluted with 1 ml of acetone, the

35 tube is closed and heated at reflux for 24 hours. The reaction medium is cooled to room temperature, filtered through a frit, the solid is rinsed with 2.5 ml of acetone. The filtrate is concentrated under vacuum, taken up in 330 μL of a 9/1 dichloromethane / methanol mixture and added to a suspension of 80 mg of PL-TBD resin (resin 1, 3,4,6,7,8- hexahydro-2H -pyrimido [1, 2-a] pyrimidine charged at 2.7 mmol / g) in 1.5 ml of

40 dichloromethane. The medium is left for 24 hours then filtered through a frit and concentrated. Compound 1 (N- (2,6-Dimethyl-phenyl) -2- (quinolin-8-yloxy) -acetamide) is obtained in the form of a brown solid (9.2 mg) with a yield of 75%. Analysis

Mass spectrometry: (ESI + and -): (M + H) ⁺ = 307 and (M + Na) ⁺ = 330

Compounds 2 and 3 were obtained in a similar manner by reacting 8-hydroxy quinoline (CAS: 148-24-3; Fluka reference: F55080) with the following commercial chloroacetamides according to the same procedure:

N- (2-chlorophenyl) -2-chloroacetamide (3289-76-7) for compound 2 (N- (2-Chlorophenyl) -2- (quinolin-8-yloxy) -acetamide) obtained in the form of '' a brown solid (7.4 mg) with a yield of 59%.

N- (chloroacetyl) -2- (trifluoromethyl) aniline (3792-04-9) for compound 3 (2-

(Quinolin-8-yloxy) -N- (2-trifluoromethyl-phenyl) -acetamide) obtained in the form of an orange solid (6.5 mg) with a yield of 47%.

EXAMPLES 10 to 19: Reaction scheme for the synthesis of compounds 4 to 13 of general formula (III):

Reaction scheme for the synthesis of compound 4:

4- (2-Chloro-acetylaτnino) -benzoic acid ethyl ester

4- [2- (4-Acetyl-phenoxy) -acetylamino] -benzoic acid ethyl compound 4

The procedure is the same as that described for the synthesis of the compounds of general formula (II).

Thus compound 4 is obtained in the form of white crystals (11.2 mg) with a yield of 82% by reaction between 1- (4-hydroxy-phenyl) -ethanone (4-hydroxyacetophenone CAS: 99-93-4) and ethyl 4 (2-chloroacetamido) -benzoate (4- (2- Chloro-acetylamino) -benzoic acid ethyl ester CAS: 26226-72-2).

Similarly, compounds 5, 6, 7, 8, 9, 10, 11, 12 and 13 are obtained according to the table below:

EXAMPLES 20. 21 and 22: Reaction scheme for the synthesis of compounds 14, 15 and 16 of general formula (IV):

Reaction scheme for the synthesis of compound 14:

benzyloxyacetylchlonde (S) - (+) - tetrahydrofurfurylamine 2-Benzyloxy-N- (2-ethoxy-butyl) -acetamide compound 14

Procedure

In a reaction tube fitted with a magnetic bar, a solution of 9.6 mg of benzyloxyacetyl chloride (CAS: 19810-31-2; Aldrich reference: 30,101-9) in 0.5 mL of dichloromethane and a solution of 5 , 2 mg of (S) - (+) - tetrahydrofurfurylamine (CAS: 7175-81-7) in 0.5 mL of 1N sodium hydroxide are introduced. The medium is diluted with 0.5 ml of dichloromethane and then 1 ml of a 1N sodium hydroxide solution is introduced there. The reaction medium is maintained under magnetic stirring for 24 h then thrown onto a liquid-liquid extraction cartridge (Chem Elut Varian) and the organic phase is evaporated. Compound 14 (2-benzyloxy-N- (tetrahydro-furan-2-ylmethyl) -acetamide) is obtained with a yield of 72% (7.2 mg).

Analysis

Mass spectrometry: ESI (+ and -): (M + H) ⁺ = 250 and (M + Na) ⁺ = 272

Compounds 15 and 16 are obtained according to the same procedure. The data are collated in the following table:

EXAMPLES 23 to 25: Reaction scheme for the synthesis of compounds 17, 18 and 19 of general formula (V):

The procedure is the same as that described for the synthesis of the compounds of general formula (IV).

Compounds 17, 18 and 19 are obtained according to the data collected in the following table:

EXAMPLE 26 Reaction scheme for the synthesis of compound 20

Phenoxy acetyl chloride 2-Methylsulfanyl-ethylamine

N- (2-Methylsulfanyl-ethyl) -2-phenoxy-acetamide compound 20

The procedure is the same as that used for the synthesis of the compounds of general formula (IV). Compound 20 is obtained in the form of a white solid (7.8 mg) with a yield of 87%.

EXAMPLE 27 Demonstration of the specific inhibitory properties of 15-PGDH of the compounds of formula (I). 1) Test on 15-PGDH type 1: The enzyme 15-PGDH is obtained as described in application FR 02/05067 filed in the name of L'Oréal, in suspension in a medium suitable for a concentration of 0.3 mg / mL then blocked at - 80 ° C. For the purposes of the test, this suspension is thawed and stored in ice. In addition, a 100 mM Tris buffer, pH = 7.4, is prepared, containing 0.1 mM of dithiothreitol (D5545, Sigma-AIdrich, L'isie D'Abeau Chesne, BP 701, 38297, Saint Quentin Fallavier), 1, 5 mM of β-NAD (N6522, Sigma-AIdrich, L'isie D'Abeau Chesne, BP 701, 38297, Saint Quentin Fallavier), 50 μM of Prostaglandin E ₂ (P4172, Sigma- AIdrich, L'isie D'Abeau Chesne, BP 701, 38297, Saint Quentin Fallavier). 0.965 ml of this buffer (previously brought to 37 ° C) are introduced into the cell of a spectrophotometer (Perkin-Elmer, Lambda 2) thermostatically controlled at 37 ° C., the measurement wavelength of which is adjusted to 340 nm. . 0.035 mL of enzyme suspension at 37 ° C are introduced into the cell concomitantly with the recording (corresponding to an increase in the optical density at 340 nm). The maximum reaction speed is noted.

The test values (containing the compounds of formula (I)) are compared to the control value (without compound (I)); the results indicated represent either the percentage inhibition of the enzymatic activity of 15-PGDH for a given concentration of compound of formula (I), or the concentration at which the compound of formula (I) reduces the activity by 50% 15-PGDH enzyme, i.e. IC _50dh -

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, in suspension in an appropriate medium, and blocked at -80 ° C. For the purposes of the test, this suspension is thawed and stored in ice.

Furthermore, a 100 mM Tris buffer, pH = 6.5, containing 20 μM of phenanthrene quinone * (P2896, Sigma-AIdrich, L'isie D'Abeau Chesne) is prepared in a brown bottle (protected from light). , BP 701, 38297, Saint Quentin Fallavier) and 100 μM of β- NADPH (N1630, Sigma-AIdrich, L'isie D'Abeau Chesne, BP 701, 38297, Saint Quentin Fallavier).

* A stock solution titrating 1 mM is prepared in absolute ethanol, brought to 40 ° C; the bottle is placed in an ultrasonic tank to facilitate the solubilization of the product.

0.950 mL of this buffer (previously brought to 37 ° C) is introduced into the cell of a spectrophotometer (Perkin-Elmer, Lambda 2) thermostatically controlled at 37 ° C, the measurement wavelength of which is adjusted to 340 nm. 0.05 mL of enzyme suspension at 37 ° C are introduced into the tank concomitantly with the recording (corresponding to a drop in optical density at 340 nm). The maximum reaction speed is noted.

The test values (containing the compound (I)) are compared to the control value (without compound (I)); the results indicated represent either the percentage inhibition of the PGFS enzymatic activity for a given concentration of compound of formula (I), or the concentration at which the compound of formula (I) reduces by 50% the enzymatic activity of PGFS, namely IC _50fS .

The results are given in the table below.

Furthermore, compounds 1 to 20, 27 to 35 do not inhibit the PGFS enzyme at 100 μM.

From these tables, it is clear that the compounds of formula (I) are inhibitors of 15-PGDH type 1, and this selectively with respect to the inhibition of PGFS.

The following compositions are obtained by the usual techniques commonly used in the cosmetic or pharmaceutical field.

EXAMPLE 28: Compound hair lotion 23 1.00 g Propylene glycol 30.00 g 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, massaging the scalp lightly to make the active ingredient penetrate. The hair is then dried in the open air. This lotion reduces hair loss and promotes regrowth. It also improves the appearance of hair. EXAMPLE 29: Hair lotion - Compound 21 1, 00 - Propylene glycol 30.00 - Ethyl alcohol 40.00 - Water qs 100.00 This lotion is applied to the scalp, once or twice a day, at the rate of 1 ml per application, gently massaging the scalp to penetrate the active ingredient. The hair is then dried in the open air. This lotion reduces hair loss and promotes regrowth. It also improves the appearance of hair. EXAMPLE 30 Wax / water mascara

- Beeswax 6.00%

- Paraffin wax 13.00%

- Hydrogenated jojoba oil 2.00%

- Water-soluble film-forming polymer 3.00%

- Triethanolamine stearate 8.00%

- Compound 23 1, 00%

- Black pigment 5.00%

- Preservative qs

- Water qs 100.00%

This mascara is applied to the eyelashes like a classic mascara with a mascara brush.

EXAMPLE 31 Hair Lotion

- Compound 21 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, once or twice a day, at the rate of 1 ml per application, by gently massaging the scalp to penetrate the active ingredient. The hair is then dried in the open air. This lotion reduces hair loss and promotes regrowth. It also improves the appearance of hair.

EXAMPLE 32 Hair Lotion

- (5E) -7 - {(1R, 2R, 3R, 5S) -3,5-dihydroxy-2 - [(3R) -3- hydroxy-5-phenyl pentyl] cyclopentyl} hept-5-enoic acid 0, 10 g - Compound 21 0.10 g

- Propylene glycol 30.00 g

- Ethyl alcohol 40.00 g

Claims

1. Use of an effective amount of at least one 2-oxy-acetamide compound of formula (I) or of one of its salts and / or of its solvates:

in which: a) Ri and R ₂ are independently chosen from: 1) hydrogen, with R ^ different from R ₂ , 2) a C ₁ -C ₂₀ alkyl radical optionally substituted by at least one substituent AL 3) a ring C ¹ hydrocarbon of 3 to 7 atoms optionally attached to at least one C ² ring of 4 to 7 atoms, the C ² ring optionally containing at least one heteroatom to form a Hy ₂ heterocycle, these C ¹ and C ² rings optionally comprising a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent A ₂ , 4) a heterocycle H i optionally attached to a C ² ring of 4 to 7 atoms, the C ² ring optionally containing at least one heteroatom to form a heterocycle Hy ₂ , these Hyi and C ² cycles possibly comprising a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent A ^ 5) one of the groups C (= NR) R ', C (= NR) NR'R " , COR, CSR, COOR, CONRR ', SO ₂ R or SO ₂ NRR'; b) R ₃ is chosen from: 1) a C ₁ -C ₂₀ alkyl radical optionally substituted with at least one substituent AL 2) a C ³ hydrocarbon ring of 3 to 7 atoms optionally attached to at least one C ⁴ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a Hy ₄ heterocycle, these C ³ and C ⁴ rings optionally comprising a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent A ₂ , 3) a Hy ₃ heterocycle chosen from pyrrole, furan, thiophene rings and pyrazole and optionally attached to a C ⁵ ring representing a phenyl, a pyridine or a pyrimidine, the heterocycle Hy ₃ and the C ⁵ ring being optionally substituted with at least one substituent A ^ 4) a heterocycle Hy ₅ different from Hy ₃ and optionally fused to a C ⁶ ring of 4 to 7 atoms, these rings Hy ₅ and C ⁶ may contain a carbonyl or thiocarbonyl function and or being substituted with at least one substituent a ^ this cycle C ⁶ containing optionally at least one hetero atom to form a heterocycle Hy _6; c) R, R 'and R "are independently chosen from: 1) hydrogen, 2) a CC ₂₀ alkyl radical optionally substituted with at least one substituent A _{1 t} 3) a C ⁷ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₇ and / or being optionally joined to a C ⁸ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₈ , the cycles C ⁷ and C ⁸ being optionally substituted with at least substituent

and may include a carbonyl or thiocarbonyl function; d) A ^ is chosen from: 1) a halogen, 2) a Cι-C ₂₀ alkyl radical optionally substituted by an OR ₅ group, 3) a C ⁹ ring of 4 to 15 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₉ and / or being optionally attached to a C ring of 4 to 7 atoms, these C ⁹ and C ¹⁰ rings optionally comprising a carbonyl or thiocarbonyl function and / or at least one substituent A ₃ chosen from OR ₅ , CF ₃ , a halogen, a CC ₂₀ alkyl radical, 4) one of the groups CF ₃ , CN, OR ₄ , SR ₄ , NR ₄ R ' ₄ , NR ₄ C (= NR' ₄ ) NR " ₄ R '" ₄ , COR ₄ , CSR ₄ , COOR ₄ , CONR ₄ R ' ₄ , NR ₄ COR' ₄ , NR ₄ CONR ' ₄ R " ₄ , SO ₂ NR ₄ R' ₄ , NR ₄ SO ₂ R ' ₄ , SO ₂ R ₄ , SiR ₄ R ' ₄ R " ₄ , Si (OR ₄ ) (OR' ₄ ) OR" ₄ , SO ₃ H, where R ₄ , R ' ₄ , R " ₄ and R'" ₄ independently represent hydrogen or a C ^ C ^ alkyl radical optionally substituted by a heterocycle Hy ₁₀ or a group CONR ₅ R '₅; e) A ₂ is chosen from: 1) halogen, 2) one of the gro upes CF ₃ , CN, OF ^, SR, NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R, SiR R' R ", NO ₂ , OCF ₃ , where R ₄ , R ' ₄ and R "independently represent a hydrogen or an alkyl radical in Cι-C ₂₀ optionally substituted by a phenyl radical, 3) an alkyl radical in CrC ₂₀ optionally substituted by an OR group ₅ , 4) a C ¹¹ ring from 4 to 7 atoms optionally containing at least one heteroatom to form a Hyu heterocycle and / or being optionally joined to a C ¹² ring of 4 to 7 atoms, these C ¹¹ and C ¹² rings can include a carbonyl or thiocarbonyl function and / or at least one substituent A ₃ chosen from OR ₅ , CF ₃ , a halogen, a CC ₂₀ alkyl radical; f) R ₅ and R ' ₅ are independently chosen from: 1) hydrogen, 2) a Cι-C ₂₀ alkyl radical; g) Hy _1τ Hy ₂ , Hy ₄ to Hy ₈ , Hy ₁₀ , and Hyu independently represent a heterocycle of 4 to 7 atoms which may contain from 1 to 4 heteroatoms chosen from N, O, S and their associations and / or include a function carbonyl or thiocarbonyl. h) Hy ₉ represents a heterocycle of 4 to 15 atoms which may contain from 1 to 5 heteroatoms chosen from N, O, S and their associations and / or contain a carbonyl or thiocarbonyl function; as an agent for inducing and / or stimulating the growth of keratin fibers, especially human keratin fibers, and / or slowing their fall and / or increasing their density. 2. Cosmetic use of at least one 2-oxy-acetamide compound of formula (I) or of one of its salts and / or of its solvates,

in which: a) Ri and R ₂ are independently chosen from 1) hydrogen, with R different from R ₂ , 2) a C ¹ -C ₂₀ alkyl radical optionally substituted by at least one AL substituent 3) a C ¹ hydrocarbon ring of 3 to 7 atoms optionally attached to at least one C 4 ring with 7 atoms, the C ² ring optionally containing at least one heteroatom to form a Hy ₂ heterocycle, these C ¹ and C ² rings optionally comprising a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent A ₂ , 4) a Hy ^ heterocycle optionally attached to a C ² ring of 4 to 7 atoms, the C ² ring optionally containing at least one heteroatom to form a Hy ₂ heterocycle, these Hy and C ² rings possibly comprising a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent AL 5) one of the groups C (= NR) R ', C (= NR) NR'R ", COR, CSR, COOR, CONRR', SO ₂ R or SO ₂ NRR '; b ) R ₃ is chosen from: 1) a C ₁ -C ₂₀ alkyl radical optionally substituted by at least u n substituting AL 2) a C ³ hydrocarbon ring of 3 to 7 atoms optionally attached to at least one C ⁴ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a Hy ₄ heterocycle, these C ³ and C ⁴ rings comprising optionally a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent A ₂ , 3) a heterocycle Hy ₃ chosen from the pyrrole, furan, thiophene and pyrazole rings and optionally attached to a C ⁵ ring representing a phenyl, a pyridine or a pyrimidine, the heterocycle Hy ₃ and the C ⁵ ring being optionally substituted with at least one substituent AL 4) a heterocycle Hy ₅ different from Hy ₃ and optionally attached to a C ⁶ ring of 4 to 7 atoms, these Hy rings ₅ and C ⁶ may contain a carbonyl or thiocarbonyl function and or be substituted by at least one substituent A _{1 (} this C ⁶ ring optionally containing at least one heteroatom to form a heterocycle Hy ₆ ; c) R, R 'and R "are independently chosen from: 1) hydrogen, 2) a CC _∑ o alkyl radical optionally substituted by at least one substituent AL 3) a C ⁷ ring of 4 to 7 atoms optionally containing at at least one heteroatom to form a heterocycle Hy ₇ and / or being optionally attached to a C ⁸ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₈ , the C ⁷ and C ⁸ rings being optionally substituted with at less substituent Ai; d) Ai is chosen from: 1) a halogen, 2) a CC ₂₀ alkyl radical optionally substituted by an OR ₅ group, 3) a C ⁹ ring of 4 to 15 atoms optionally containing at least one heteroatom for forming a heterocycle Hy ₉ and / or being optionally attached to a C ring of 4 to 7 atoms, these C ⁹ and C ¹⁰ rings optionally comprising a carbonyl or thiocarbonyl function and / or at least one substituent A ₃ chosen from OR ₅ , CF ₃ , a halogen, a C ^ C ^ alkyl radical, 4) one of the groups CF ₃ , CN, OR ₄ , SR ₄ , NR ₄ R ' ₄ , NR ₄ C (= NR' ₄ ) NR " ₄ R '" ₄ , COR ₄ , CSR ₄ , COOR ₄ , CONR ₄ R ' ₄ , NR ₄ COR' ₄ , NR ₄ CONR ' ₄ R " ₄ , SO ₂ NR ₄ R' ₄ , NR ₄ SO ₂ R ' ₄ , SO ₂ R ₄ , SiR ₄ R ' ₄ R " ₄ , Si (OR ₄ ) (OR' ₄ ) OR" ₄ , SO ₃ H, where R ₄ , R ' ₄ , R " ₄ and R'" ₄ independently represent a hydrogen or an alkyl radical in CC _∑ o optionally substituted by a heterocycle Hyio or a group CONR ₅ R '₅; e) A is chosen from: 1) a halogen, 2) one of the groups CF ₃ , CN, OR ₄ , SR ₄ , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR ₄ R ' ₄ R " ₄ , NO ₂ , OCF ₃ , where R ₄ , R' ₄ and R" ₄ independently represent a hydrogen or a C ₁ -C ₂₀ alkyl radical optionally substituted by a phenyl radical, 3) an alkyl radical in CC ₂₀ optionally substituted by an OR group ₅ , 4) a C ¹¹ ring of 4 to 15 atoms optionally containing at least one heteroatom to form a Hyu heterocycle and / or being optionally joined to a C ring of 4 to 7 atoms, these C ¹¹ and C ¹² rings which may contain a carbonyl or thiocarbonyl function and / or at least one substituent A ₃ chosen from OR ₅ , CF ₃ , a halogen, an alkyl radical in CC ₂₀ ; f) R ₅ and R ' ₅ are independently chosen from: 1) hydrogen,

2) a CC ₂₀ alkyl radical; g) HyL Hy ₂ , Hy ₄ to Hy ₈ , Hy ₁₀ and Hyu independently represent a heterocycle of 4 to 7 atoms which may contain from 1 to 4 heteroatoms chosen from N, O, S and their associations and / or contain a carbonyl function or thiocarbonyl, h) Hy ₉ represents a heterocycle of 4 to 15 atoms which may contain from 1 to 5 heteroatoms chosen from N, O, S and their associations and / or contain a carbonyl or thiocarbonyl function; in a cosmetic composition for caring for and / or making up keratin fibers, in particular human fibers, in order to reduce their fall and / or increase their density.

3. Use of at least one 2-oxy-acetamide compound of formula (I) or one of its salts and / or its solvates,

in which: a) Ri and R ₂ are independently chosen from: 1) hydrogen, with Ri different from R ₂ , 2) a CC ₂₀ alkyl radical optionally substituted by at least one substituent AL 3) a C ¹ hydrocarbon ring of 3 to 7 atoms optionally attached to at least one C ² ring of 4 to 7 atoms, the C ² ring optionally containing at least one heteroatom to form a Hy ₂ heterocycle, these C ¹ and C ² rings optionally comprising a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent a _2, 4) heterocycle _t Hy optionally fused to a ring C ² of 4 to 7 atoms, the ring C ² optionally containing at least one hetero atom to form a heterocycle Hy ₂ these Hyi and C ² rings which may include a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent A 5) one of the groups C (= NR) R ", C (= NR) NR'R", COR, CSR , COOR, CONRR ', SO ₂ R or SO ₂ NRR'; b) R ₃ is chosen from: 1) a CC ₂₀ alkyl radical optionally substituted with at least one substituent AL 2) a C ³ hydrocarbon ring of 3 to 7 atoms optionally attached to at least one C ⁴ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₄ , these cycles C ³ and C ⁴ optionally comprising a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent A ₂ , 3) a heterocycle Hy ₃ chosen from the rings pyrrole, furan, thiophene and pyrazole and optionally attached to a C ⁵ ring representing a phenyl, a pyridine or a pyrimidine, the heterocycle Hy ₃ and the C ⁵ ring being optionally substituted with at least one substituent AL 4) a heterocycle Hy ₅ different from Hy ₃ and optionally attached to a C ⁶ ring of 4 to 7 atoms, these Hy ₅ and C ⁶ rings can contain a carbonyl or thiocarbonyl function and / or be substituted by at least one substituent AL ce C ⁶ ring optionally containing at least one heteroatom to form a Hy ₆ heterocycle; c) R, R 'and R "are independently chosen from: 1) hydrogen, 2) a C ^ C ^ alkyl radical optionally substituted by at least one substituent A 3) a C ⁷ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₇ and / or being optionally joined to a C ⁸ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₈ , the C ⁷ and C ⁸ rings being optionally substituted by at least substituent Ai and which may comprise a carbonyl or thiocarbonyl function; d) ^ is chosen from: 1) a halogen, 2) an alkyl radical in dC ₂ o optionally substituted by an OR ₅ group, 3) a C ⁹ of 4 ring with 15 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₉ and / or being optionally joined to a C ring of 4 to 7 atoms, these C ⁹ and C ¹⁰ rings optionally comprising a carbonyl or thiocarbonyl function and / or at least as ubstituant A ₃ chosen from OR ₅ , CF ₃ , a halogen, an alkyl radical in C ^ C ^, 4) one of the groups CF ₃ , CN, OR ₄ , SR ₄ , NR ₄ R ' ₄ , NR ₄ C (= NR ' ₄ ) NR " ₄ R'" ₄ , COR ₄ , CSR ₄ , COOR ₄ , CONR ₄ R '_4> NR ₄ COR' _4l NR ₄ CONR ' ₄ R " ₄ , SO ₂ NR ₄ R' ₄ , NR ₄ SO ₂ R ' ₄ , SO ₂ R ₄ , SiR ₄ R' ₄ R " ₄ , Si (OR ₄ ) (OR ' ₄ ) OR" ₄ , SO ₃ H, where R ₄ , R' ₄ , R " ₄ and R '" ₄ independently represent a hydrogen or a C 1 -C 4 alkyl radical optionally substituted by a Hyio heterocycle or a group CONR ₅ R'₅; e) A ₂ is chosen from: 1) a halogen, 2) one of the groups CF ₃ , CN, OR ₄ , SR ₄ , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR, COOR, SO ₂ R ₄ , SiR R ' ₄ R ", NO ₂ , OCF ₃ , where R, R' ₄ and R" independently represent a hydrogen or an alkyl radical in CrC ₂₀ optionally substituted by a phenyl radical, 3) an alk radical in CrC ₂₀ optionally substituted by an OR group ₅ , 4) a C ring of 4 to 15 atoms optionally containing at least one heteroatom to form a heterocycle Hy _Η and / or being optionally joined to a C ring of 4 to 7 atoms, these C ¹¹ and C ¹² may comprise a carbonyl or thiocarbonyl function and / or at least one substituent A ₃ chosen from OR ₅ , CF ₃ , a halogen, a Cι-C ₂₀ alkyl radical; f) R ₅ and R ' ₅ are independently chosen from: 1) hydrogen, 2) a Cι-C ₂₀ alkyl radical; g) Hy _L Hy ₂ , Hy ₄ to Hy ₈ , Hy ₁₀ and Hy ^ independently represent a heterocycle of 4 to 7 atoms which may contain from 1 to 4 heteroatoms chosen from N, O, S and their associations and / or contain a function carbonyl or thiocarbonyl, h) Hy ₉ represents a heterocycle of 4 to 15 atoms which may contain from 1 to 5 heteroatoms chosen from N, O, S and their associations and / or contain a carbonyl or thiocarbonyl function; for the manufacture of a care or treatment composition for keratin fibers, in particular human fibers, intended to induce and / or stimulate the growth of said fibers and / or slow their fall and / or increase their density.

4. Use of at least one 2-oxy-acetamide compound of formula (I) or one of its salts and / or its solvates,

in which: a) Ri and R ₂ are independently chosen from: 1) hydrogen, with Ri different from R ₂ , 2) a Cι-C ₂₀ alkyl radical optionally substituted by at least one substituent AL 3) a C hydrocarbon ring ¹ of 3 to 7 atoms optionally attached to at least one C ² ring of 4 to 7 atoms, the C ² ring optionally containing at least one heteroatom to form a Hy ₂ heterocycle, these C ¹ and C ² rings optionally comprising a carbonyl function or thiocarbonyl and / or being substituted by at least one substituent A ₂ , 4) a heterocycle Hy ₁ optionally attached to a C ² ring of 4 to 7 atoms, the C ² ring optionally containing at least one heteroatom to form a heterocycle Hy ₂ , these cycles Hy ^ and C ² possibly comprising a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent A _{1 (} 5) one of the groups C (= NR) R ', C (= NR) NR'R " , COR, CSR, COOR, CONRR ', SO ₂ R or S0 ₂ NRR'; b) R ₃ is chosen from : 1) a CC ₂₀ alkyl radical optionally substituted by at least one substituent AL 2) a C ³ hydrocarbon ring of 3 to 7 atoms optionally attached to at least one C ⁴ ring of 4 to 7 atoms optionally containing at least one hetero atom for forming a Hy ₄ heterocycle, these C ³ and C ⁴ rings optionally comprising a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent A ₂ , 3) a Hy ₃ heterocycle chosen from the pyrrole, furan, thiophene and pyrazole cycles and optionally attached to a C ⁵ ring representing a phenyl, a pyridine or a pyrimidine, the heterocycle Hy ₃ and the C ⁵ ring being optionally substituted with at least one substituent AL 4) a heterocycle Hy ₅ different from Hy ₃ and optionally attached to a C ⁶ ring of 4 to 7 atoms, these Hy ₅ and C ⁶ rings can comprise a carbonyl or thiocarbonyl function and / or be substituted by at least one substituent A _{1 f} this C ⁶ ring optionally containing at least one heteroatom to form a Hy ₆ heterocycle; c) R, R ', R "and R"' are independently chosen from: 1) hydrogen, 2) a CC ₂₀ alkyl radical optionally substituted by at least one AL substituent 3) a C ⁷ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₇ and / or possibly being joined to a C ⁸ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₈ , the cycles C ⁷ and C ⁸ being optionally substituted with at least substituent Ai and which may contain a carbonyl or thiocarbonyl function; d) Ai is chosen from: 1) a halogen, 2) a Cι-C ₂₀ alkyl radical optionally substituted by an OR group ₅ , 3) a C ring of 4 to 15 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₉ and / or being optionally attached to a C ¹⁰ ring of 4 to 7 atoms, these C ⁹ and C ¹⁰ rings optionally comprising a carbonyl or thiocarbonyl function and / or at least one substituent A ₃ chosen from OR ₅ , CF ₃ , a halogen, an alkyl radical in CC ₂ o, 4) one of the groups CF ₃ , CN, OR ₄ , SR ₄ , NR ₄ R ' ₄ , NR ₄ C (= NR' ₄ ) NR " ₄ R"" ₄ , COR ₄ , CSR ₄ , COOR ₄ , CONR ₄ R ' ₄ , NR ₄ COR' ₄ , NR ₄ CONR ' ₄ R " ₄ , S0 ₂ NR ₄ R' ₄ , NR ₄ SO ₂ R ' ₄ , SO ₂ R ₄ , SiR ₄ R ' ₄ R " ₄ , Si (OR ₄ ) (OR' ₄ ) OR" ₄ , SO ₃ H, where R ₄ , R ' ₄ , R " ₄ and R'" ₄ independently represent hydrogen or a CτC ₂ o alkyl radical optionally substituted by a heterocycle Hy ₁₀ or a group CONR ₅ R '₅; e) A ₂ is chosen from: 1) halogen, 2) a groups CF ₃ , CN, OR ₄ , SR ₄ , NR ₄ R ', OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR R' ₄ R " ₄ , N0 ₂ , OCF ₃ , where R ₄ , R ' ₄ and R " ₄ independently represent a hydrogen or an alkyl radical in CC ₂₀ optionally substituted by a phenyl radical, 3) an alkyl radical in C ^ C _∑ o optionally substituted by a group OR ₅ , 4) a C ring of 4 to 7 atoms optionally containing at least one heteroatom to form a Hyu heterocycle and / or being optionally joined to a C ring of 4 to 7 atoms, these C ¹¹ and C ¹² rings can include a carbonyl or thiocarbonyl function and / or at least one substituent A ₃ chosen from OR ₅ , CF ₃ , a halogen, a CC ₂₀ alkyl radical; f) R ₅ and R ' ₅ are independently chosen from: 1) hydrogen, 2) a C ₁ -C ₂₀ alkyl radical; g) HVL Hy ₂ , Hy ₄ to Hy ₈ , Hy ₁₀ and Hyu independently represent a heterocycle of 4 to 7 atoms which may contain from 1 to 4 heteroatoms chosen from N, O, S and their associations and / or contain a carbonyl function or thiocarbonyl, h) Hy ₉ represents a heterocycle of 4 to 15 atoms which may contain from 1 to 5 heteroatoms chosen from N, O, S and their associations and / or contain a carbonyl or thiocarbonyl function; as an inhibitor of 15-hydroxy prostaglandin dehydrogenase type 1, in particular human.

5. Use of at least one 2-oxy-acetamide compound of formula (I) or one of its salts and / or its solvates,

in which: a) Ri and R ₂ are independently chosen from: 1) hydrogen, with R different from R ₂ , 2) a C ^ C ^ alkyl radical optionally substituted with at least one substituent A ^, 3) a ring hydrocarbon C ¹ of 3 to 7 atoms optionally attached to at least one C ring of 4 to 7 atoms, the C ² ring optionally containing at least one heteroatom to form a Hy ₂ heterocycle, these C ¹ and C ² rings optionally comprising a function carbonyl or thiocarbonyl and / or being substituted by at least one substituent A ₂ , 4) a heterocycle Hy _! optionally attached to a C ² ring of 4 to 7 atoms, the C ² ring optionally containing at least one heteroatom to form a heterocycle Hy ₂ , these Hy rings _! and C ² may contain a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent AL 5) one of the groups C (= NR) R ', C (= NR) NR'R ", COR, CSR, COOR, CONRR ', SO ₂ R or S0 ₂ NRR'; b) R ₃ is chosen from: 1) a CC ₂₀ alkyl radical optionally substituted by at least one AL 2 substituent) a C ³ hydrocarbon ring of 3 to 7 atoms optionally attached with at least one C ⁴ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy, these C ³ and C ⁴ rings optionally comprising a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent A ₂ , 3) a heterocycle Hy ₃ chosen from the pyrrole, furan, thiophene and pyrazole cycles and optionally attached to a C ⁵ ring representing a phenyl, a pyridine or a pyrimidine, the heterocycle Hy ₃ and the C ⁵ ring being optionally substituted with at least one substituent AL 4) a heterocycle Hy ₅ different from d e Hy ₃ and optionally attached to a C ⁶ ring of 4 to 7 atoms, these Hy ₅ and C ⁶ rings being able to comprise a carbonyl or thiocarbonyl function and / or to be substituted by at least one substituent AL this C ⁶ ring optionally containing at least a heteroatom to form a Hy ₆ heterocycle; c) R, R 'and R "are independently chosen from: 1) hydrogen, 2) a CC ₂ alkyl radical optionally substituted with at least one substituent AL 3) a C ⁷ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₇ and / or being optionally joined to a C ⁸ ring of 4 to 7 atoms possibly containing at least one heteroatom to form a heterocycle Hy ₈ , the C ⁷ and C ⁸ rings being optionally substituted with at least substituent Ai and which may contain a carbonyl or thiocarbonyl function; d) Ai is chosen from: 1) a halogen, 2) an alkyl radical in

3) a C ⁹ ring of 4 to 15 atoms possibly containing at least one heteroatom to form a heterocycle Hy ₉ and / or being optionally joined to a C ring of 4 to 7 atoms, these C ⁹ and C ¹⁰ rings optionally comprising a function carbonyl or thiocarbonyl and / or at least one substituent A ₃ chosen from OR ₅ , CF ₃ , a halogen, a C ₁ -C ₂₀ alkyl radical, 4) one of the groups CF ₃ , CN, OR ₄ , SR ₄ , NR ₄ R ' ₄ , NR ₄ C (= NR ' ₄ ) NR " ₄ R'" ₄ , COR ₄ , CSR ₄ , COOR ₄ , CONR ₄ R ' ₄ , NR ₄ COR' ₄ , NR ₄ CONR ' ₄ R " ₄ , SO ₂ NR ₄ R ' ₄ , NR ₄ SO ₂ R' ₄ , SO ₂ R ₄ , SiR ₄ R ' ₄ R " ₄ , Si (OR ₄ ) (OR' ₄ ) OR" ₄ , SO ₃ H, where R ₄ , R ^* ₄ , R " ₄ and R '" ₄ independently represent a hydrogen or an alkyl radical in C ^ C ^ optionally substituted by a heterocycle Hy ₁₀ or a group CONR ₅ R'₅; e) A ₂ is chosen from: 1) halogen, 2) one of the groups CF ₃ , CN, OR ₄ , SR ₄ , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR, COOR ₄ , S0 ₂ R ₄ , SiR ₄ R' R " ₄ , NO ₂ , OCF ₃ , where R ₄ , R ' ₄ and R " ₄ independently represent a hydrogen or an alkyl radical in CC ^ optionally substituted by a phenyl radical, 3) an alkyl radical in CC ₂ o optionally substituted by an OR group ₅ , 4) a ring C ¹¹ of 4 to 7 atoms optionally containing at least one heteroatom to form a Hyu heterocycle and / or being optionally joined to a C ring of 4 to 7 atoms, these C ¹¹ and C ¹² rings can contain a carbonyl or thiocarbonyl function and / or at least one substituent A ₃ chosen from OR ₅ , CF ₃ , a halogen, a C-ι-C ₂₀ alkyl radical; f) R ₅ and R ' ₅ are independently chosen from: 1) hydrogen, 2) a CC ₂₀ alkyl radical; g) Hyi, Hy, Hy to Hy ₈ , Hy ₁₀ and Hyu independently represent a heterocycle of 4 to 7 atoms which may contain from 1 to 4 heteroatoms chosen from N, O, S and their associations and / or contain a carbonyl or thiocarbonyl function , h) Hy ₉ represents a heterocycle of 4 to 15 atoms which may contain from 1 to 5 heteroatoms chosen from N, O, S and their associations and / or comprise a carbonyl or thiocarbonyl function; for the manufacture of a composition for caring for or treating keratin fibers, in particular human fibers, intended for treating disorders linked to 15-hydroxy prostaglandin dehydrogenase type 1, in particular human.

6. Use according to one of the preceding claims, characterized in that the human keratin fibers are hair, eyebrows, eyelashes, beard hair, mustache hair and pubic hair.

7. Cosmetic use of at least one 2-oxy-acetamide compound of formula (I) or one of its salts and or its solvates, as defined in claim 1, in a cosmetic hair care composition of human being to reduce hair loss and / or increase their density and / or treat andro-chrono-genetic alopecia and / or treat alopecia of natural origin.

8. Use of at least one 2-oxy-acetamide compound of formula (I) or one of its salts and / or its solvates, as defined in claim 1, for the preparation of a hair cosmetic composition to be human, intended to induce and / or stimulate hair growth and / or slow down their fall and / or increase their density and / or treat androgenic alopecia and / or treat alopecia of natural origin.

9. Cosmetic use of at least one 2-oxy-acetamide compound of formula (I) or of one of its salts and / or of its solvates, as defined in claim 1, in a cosmetic care composition and / or make-up of human eyelashes to induce and / or stimulate their growth and / or increase their density.

10. Use of at least one 2-oxy-acetamide compound of formula (I) or one of its salts and / or its solvates, as defined in claim 1, for the preparation of a care composition or treatment of human eyelashes, intended to induce and / or stimulate their growth and / or increase their density.

11. Use according to one of the preceding claims, characterized in that Ri represents hydrogen and R ₂ represents one of the following groups: - a saturated C ₁ -C ₁₀ alkyl radical optionally substituted by one or two substituents A - a saturated hydrocarbon ring of 3 to 6 carbon atoms, - a heterocycle Hy-i saturated or not with 5, 6 or 7 atoms, comprising from 1 to 2 heteroatoms chosen from O, N and S and optionally a carbonyl function and / or from one to four substituents A ' ₂ , - a phenyl ring in particular substituted by one or two substituents A " ₂ chosen from a halogen, N0 ₂ , OCF ₃ , CF ₃ , OR ₄ , OCH ₂ R, COOR ₄ , a C ₁ -C ₁₀ alkyl radical, a hydrocarbon or heterocyclic aromatic ring, - a phenyl ring attached to one or two hydrocarbon or heterocyclic rings of 5 to 6 atoms, thus forming condensed rings.

12. Use according to one of the preceding claims, characterized in that Hyi represents a heterocycle chosen from azetidine, pyrrole, dihydropyrrole, pyrrolidine, furan, dihydrofuran, tetrahydrofuran, thiophene, dihydrothiophene, tetrahydrothiophene, imidazole, dihydroimidazole, imidazolidine, imidazolidine dihydropyrazole, pyrazolidine, oxazole, dihydro-oxazole, oxazolidine, isoxazole, dihydro-isoxazole, isoxazolidine, isothiazole, dihydro-isothiazole, isothiazolidine, triazole, dihydrotriazole, triazolidine, oxadiazole, dihydro-iadiazole, dihydro-iadiazole pyridine, dihydropyridine, tetrahydropyridine, piperidine, pyran, dihydropyran, tetrahydropyran, pyrimidine, dihydropyrimidine, tetrahydropyrimidine, piperazine, pyridazine, pyrazine, triazine, morpholine, azepine, diazepine.

13. Use according to one of the preceding claims, characterized in that R ₃ represents one of the following groups: - a hydrocarbon ring, optionally substituted by one or more substituents A '" ₂ chosen from a phenyl radical, COOR, OR , COR ₄ , CN, a heterocycle with 5 or 6 atoms comprising from 1 to 2 heteroatoms chosen from O, N and S, a halogen, a phenyl radical optionally substituted by CN, a linear or branched alkyl radical in CrC ₁₀ , with R ₄ representing a hydrogen or a CC ₁₀ alkyl radical, - a phenyl ring joined to one or two C ⁴ hydrocarbon or heterocyclic rings of 5 to 6 atoms, the C ring or rings optionally comprising a carbonyl function and / or being optionally substituted by a saturated Cidyl alkyl radical, this phenyl and this or these other C ⁴ rings forming condensed rings, - a saturated C ₁ -C ₁₀ alkyl radical optionally substituted with one or two substituents A

14. Use according to one of the preceding claims, characterized in that the heterocycles Hy ₂ , Hy, Hy ₆ , Hy ₇ , Hy ₈ , Hy ₉ , Hyio and Hyu independently represent the azetidine, pyrrole, dihydropyrrole, pyrrolidine, furan cycles, dihydrofuran, tetrahydrofuran, thiophene, dihydrothiophene, tetrahydrothiophene, imidazole, dihydro-imidazole, imidazolidine, thiazole, dihydrothiazole, thiazolidine, pyrazole, dihydropyrazole, pyrazolidine, isazro-isoxoxole, dihydro-oxazole, dihydro-oxazole, isothiazole, isothiazolidine, triazole, dihydrotriazole, triazolidine, oxadiazole, dihydro-oxadiazole, oxadiazolidine, thiadiazole, dihydrothiadiazole, thiadiazolidine, tetrazole, pyridine, dihydropyridine, tetrahydropyridine, tetrahydropyridine, piperidine, pyranne pyrazine, triazine, morpholine, azepine, diazepine or even crown ether 15-C-5 for Hy ₉ .

15. Use according to one of the preceding claims, characterized in that the heterocycles Hy ₂ , Hy ₄ , Hy ₆ , Hy ₇ , Hy ₈ , Hy ₉ , Hyι ₀ and Hyu independently represent pyrrole, pyrrolidine, imidazole, furan, thiophene , oxazole, thiazole, isoxazole, isothiazole, oxadiazole, pyrazole, tetrazole, pyridine, pyrimidine, triazole, pyrazine, pyridazine, piperidine, piperazine, morpholine, or crown ether 15-C-5 for Hy ₉ .

16. Use according to one of the preceding claims, characterized in that Ai represents a hydrocarbon ring or a heterocycle comprising 1 to 2 heteroatoms chosen from O and N, this hydrocarbon or heterocyclic ring comprising 5 or 6 atoms and optionally a carbonyl function and / or a substituent A ₃ ; or a group chosen from SiR ₄ R ' ₄ R " ₄ , COOR ₄ , NR ₄ R' ₄ , OR ₄ , SR ₄ , CONR R ' ₄ .

17. Use according to one of the preceding claims, characterized in that A ₃ represents a Cι-C ₁₀ alkyl radical, CF ₃ , a halogen atom, OH or OCH ₃ .

18. Use according to one of the preceding claims, characterized in that Hyi represents a γ-butyrolactone, a piperidine, a 1,3-benzodioxole optionally substituted by a CC ₄ alkyl radical.

19. Use according to one of the preceding claims, characterized in that the salt of the compound of formula (I) is a salt chosen from sodium or potassium salts, ammonium salts, zinc salts (Zn ^{2 +} ), calcium (Ca ²⁺ ), copper (Cu ⁺ ), iron (Fe ²⁺ and Fe ³⁺ ), strontium (Sr ^{2 *} ), magnesium (Mg ²⁺ ), manganese (Mn ²⁺ ), the tri-ethanolamine, mono-ethanolamine, ethanolamine, hexadecylamine and N, N, N ', N'-tetrakis- (hydroxy-propyl-2) ethylene diamine salts, hydroxides, halohydrates, carbonates, hydrogen carbonates, citrates, lactates, glycolates, gluconates, acetates, propionates, fumarates, oxalates, tartrates, sulfates, phosphates, hydrogen phosphates.

20. Use according to one of the preceding claims, characterized in that the 2-oxy-acetamide compound is in the form of a hydrate.

21. Use according to one of the preceding claims, characterized in that the 2-oxy-acetamide compound satisfies the following formula or one of its salts and / or one of its solvates:

in which: α) R ^ is chosen from: 1) a CC ₁₀ alkyl radical optionally substituted with at least one substituent A ₄ , 2) a C ¹⁵ hydrocarbon ring of 5 to 6 atoms optionally substituted with at least one substituent A ₅ ; β) R ₁₂ is chosen from: 1) a Cι-C ₁₀ alkyl radical optionally substituted by at least one substituent A, 2) a C ¹⁶ hydrocarbon ring of 5 to 6 atoms optionally attached to at least one C ¹⁷ of 5 ring with 6 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₁₇ , these rings C ¹⁶ and C ¹⁷ optionally comprising a carbonyl function and / or being substituted by at least one substituent A ₅ ; γ) A ₄ is chosen from: 1) a C ¹⁸ ring of 5 to 6 atoms optionally containing at least one heteroatom to form a Hy ₁₈ heterocycle, this cycle or this heterocycle being optionally substituted by at least one substituent A ₆ chosen from ORι ₄ , CF ₃ , a halogen, an alkyl radical in C Cι ₀ ; 2) one of the groups CF ₃ , CN, OR ₁₃ , SR ₁₃ , NR ₁₃ R _'13 , NR ₁₃ C (= NR' ₁₃ ) NR " ₁₃ R '" ₁₃ , COR ₁₃ , COOR ₁₃ , CONR ₁₃ R' ₁₃ , NR ₁₃ COR _'13 , NR ₁₃ CONR' ₁₃ R " ₁₃ , S0 ₂ NR ₁₃ R _'13 , NR ₁₃ S0 ₂ R'ι ₃ , S0 ₂ Rι ₃ , SiR ₁₃ R' ₁₃ R" ι ₃ , S0 ₃ H, where R ₁₃ , R'ι ₃ , R "ι ₃ and R '" ₁₃ independently represent a hydrogen or a CC ₁₀ alkyl radical; δ) A ₅ is chosen from: 1) a halogen, 2) one of the groups CF ₃ , CN, OR ₁₅ , SR ₁₅ , NR ₁₅ R _'15 , OCOR ₁₅ , COR ₁₅ , COOR ₁₅ , S0 ₂ R ₁₅ , SiR ₁₅ R'ι ₅ R "i ₅ , N0 ₂ , OCF ₃ , where R _15l R _'15 and R" ₁₅ independently represent a hydrogen or an alkyl radical in CC ₁₀ optionally substituted by a phenyl radical, 3) an alkyl radical in C ₁ -C ₁₀ optionally substituted by an OR group ₁ , 4) a C ring of 5 to 6 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₁₉ and / or possibly comprising a carbonyl function; ε) R ₁₄ is chosen from: 1) hydrogen, 2) a C ₁ -C ₁₀ alkyl radical; η) Hyι ₇ , Hy ₁₈ , and Hy ₁₉ independently represent a heterocycle of 5 to 6 atoms which may contain from 1 to 4 heteroatoms chosen from N, O, S and their associations and / or contain a carbonyl function.

22. Use according to one of the preceding claims, characterized in that the 2-oxy-acetamide compound satisfies one of the following formulas (II) to (V) or one of the corresponding salts and or solvates: Formula (II)

Formula (III)

Formula (IV)

Formula (V)

in which :

(i) R7 and R8 independently represent: 1) hydrogen, 2) halogen F or Cl, 3) one of the groups CF ₃ , CN, OR ₄ , SR ₄ , NHR ₆ , NR ₆ R ' ₆ OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , S0 ₂ R ₄ , SiR ₄ R ' ₄ R " ₄ , OCF ₃ , where R ₄ , R' ₄ and R" ₄ independently represent a hydrogen or a C ^ C _M alkyl radical optionally substituted by a phenyl radical and where R ₆ and R ' ₆ represent an alkyl radical in CC ₂₀ optionally substituted by a phenyl radical, 4) an alkyl radical in Cι-C ₂₀ optionally substituted by an OR ₅ group where R ₅ represents a hydrogen or an alkyl radical in CrC ₂₀ , 5) a C ¹¹ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy ^ and / or being optionally joined to a C ring of 4 to 7 atoms, these cycles C ¹¹ and C ¹² may comprise a carbonyl or thiocarbonyl function; (ii) Z represents one of the following cycles and heterocycles:

(iii) X and Y independently represent a hydrogen or A ₂ or can form a C ¹³ ring joined from 4 to 7 atoms, this C ¹³ ring optionally comprising at least one heteroatom, being optionally substituted with at least one substituent A ₂ and optionally attached to another cycle C ¹⁴ ;

(iv) A represents one of the following three groups:

(v) R ₃ has the same meaning as given for formula (I); provided that when Z represents the dibenzofuran heterocycle, X and Y independently represent: 1) hydrogen, 2) halogen, 3) one of the groups CF ₃ , CN, OR ₉ , SR ₄ , NR ₄ R ' ₄₎ OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , S0 ₂ R ₄ , SiR R ' ₄ R " ₄ , N0 ₂ , OCF ₃ , where R ₄ , R' ₄ and R" ₄ independently represent hydrogen or an alkyl radical in CC ₂₀ optionally substituted by a phenyl radical and where R ₉ represents a hydrogen or a C ₂ -C ₂₀ alkyl radical optionally substituted by a phenyl radical, 4) a C ₂ -C ₂₀ alkyl radical optionally substituted by an OR ₅ group , 5) a C ring of 4 to 7 atoms optionally containing at least one heteroatom to form a Hyu heterocycle and / or being optionally joined to a C ring of 4 to 7 atoms, these C ¹¹ and C ¹² rings can include a carbonyl function or thiocarbonyl; or provided that when Z represents the cycle:

X and Y independently represent: 1) hydrogen, in this case X different from Y, 2) fluorine, 3) one of the groups OR ₁₀ , SR ₄ , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₆ , SiR ₄ R ' ₄ R " ₄ , OCF ₃ , where R ₄ , R' ₄ and R" ₄ independently represent a hydrogen or a dC ₂₀ alkyl radical optionally substituted by a phenyl radical, where R ₆ represents a CC ₂₀ alkyl radical optionally substituted by a radical phenyl and where Rio represents a hydrogen or a benzyl radical or a C ₃ -C ₂₀ alkyl radical optionally substituted by a phenyl radical, 4) a C ₂ -C ₂₀ alkyl radical optionally substituted by a group OR ₅ , 5) X and Y can also form a C ring with 5 atoms possibly containing one or two oxygen atoms and being optionally joined to another C ¹⁴ ring

23. Use according to one of claims 1 to 21, characterized in that the compound of formula (I) satisfies one of the following formulas or one of the corresponding salts and / or solvates:

Compound 2

Compound 3

Compound 5

Compound 6

Compound 9

Compound 10

Compound 12

Compound 13

Compound 18

Compound 19

Compound 21

Compound 23

Compound 24

Compound 28

Compound 32

Compound 34

Compound 35

24. 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 from 10 ^"2 to 2%, relative to the total weight of the composition.

25. Use according to one of the preceding claims, characterized in that the composition is a composition for topical application.

26. Composition for caring for and / or making up keratin fibers, containing a physiologically acceptable medium and an effective amount of at least one 2-oxy-acetamide compound of formula (I) or one of its salts and / or of its solvates:

in which: a) Ri and R ₂ are independently chosen from: 1) hydrogen, with RT different from R ₂ , 2) a CC ₂₀ alkyl radical optionally substituted by at least one substituent AL 3) a C ¹ hydrocarbon ring of 3 to 7 atoms optionally attached to at least one C ring of 4 to 7 atoms, the C ² ring optionally containing at least one heteroatom to form a Hy ₂ heterocycle, these C ¹ and C ² rings optionally comprising a carbonyl or thiocarbonyl function and / or being substituted with at least one substituent A ₂ , 4) a heterocycle Hy _! optionally attached to a C ² ring of 4 to 7 atoms, the C ² ring optionally containing at least one heteroatom to form a heterocycle Hy ₂ , these Hy rings _! and C ² may contain a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent AL 5) one of the groups C (= NR) R \ C (= NR) NR'R ", COR, CSR, COOR, CONRR ', SO ₂ R or S0 ₂ NRR'; b) R ₃ is chosen from: 1) a C ₁ -C ₂₀ alkyl radical optionally substituted with at least one AL 2 substituent) a C ³ hydrocarbon ring of 3 to 7 atoms optionally attached to at least one C ⁴ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy, these C ³ and C ⁴ rings optionally comprising a carbonyl or thiocarbonyl function and / or being substituted by at least one substituent A ₂ , 3) a heterocycle Hy ₃ chosen from the pyrrole, furan, thiophene and pyrazole rings and optionally attached to a C ⁵ ring representing a phenyl, a pyridine or a pyrimidine, the heterocycle Hy ₃ and the C ⁵ ring being optionally substituted with the minus one substituent AL 4) a heterocycle Hy different from Hy ₃ and optionally attached to a C ⁶ ring of 4 to 7 atoms, these Hy ₅ and C ⁶ rings can comprise a carbonyl or thiocarbonyl function and / or be substituted by at least one substituent A _{1 t} this C ⁶ ring optionally containing at least one heteroatom to form a Hy ₆ heterocycle; c) R, R 'and R "are independently chosen from: 1) hydrogen, 2) a dC- ₂₀ alkyl radical optionally substituted by at least one substituent AL 3) a C ⁷ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₇ and / or being optionally attached to a C ring ⁸ from 4 to 7 atoms optionally containing at least one heteroatom to form a Hy ₈ heterocycle, the C ⁷ and C ⁸ rings being optionally substituted with at least substituent Ai and possibly comprising a carbonyl or thiocarbonyl function; d) Ai is chosen from: 1) a halogen, 2) a Cι-C ₂₀ alkyl radical optionally substituted by an OR ₅ group, 3) a C ⁹ ring of 4 to 15 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₉ and / or being optionally joined to a C ¹⁰ ring of 4 to 7 atoms, these C ⁹ and C ¹⁰ rings optionally comprising a carbonyl or thiocarbonyl function and / or at least one substituent A ₃ chosen from OR ₅ , CF ₃ , halogen, a C ₁ -C ₂₀ alkyl radical, 4) one of the groups CF ₃ , CN, OR ₄ , SR ₄ , NR ₄ R ' ₄ , NR ₄ C (= NR' ₄ ) NR " ₄ R"" ₄ , COR ₄ , CSR ₄ , COOR ₄ , CONR ₄ R ' ₄ , NR ₄ COR' _4l NR ₄ CONR ' ₄ R" ₄ , S0 ₂ NR ₄ R' ₄ , NR ₄ S0 ₂ R ' _4l S0 ₂ R ₄ , SiR ₄ R ' ₄ R " ₄ , Si (OR ₄ ) (OR' ₄ ) OR" ₄ , SO ₃ H, where R ₄ , R ' _4l R " ₄ and R'" ₄ independently represent hydrogen or a CC _∑ o alkyl radical optionally substituted by a heterocycle Hy ₁₀ or a group CONR ₅ R '₅; e) A ₂ is chosen from: 1) halogen, 2) one of the groups CF ₃ , CN, OR ₄ , SR ₄ , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , S0 ₂ R ₄ , SiR ₄ R' ₄ R " ₄ , N0 ₂ , OCF ₃ , where R ₄ , R ' ₄ and R " ₄ independently represent a hydrogen or an alkyl radical in CC ₂₀ optionally substituted with a phenyl radical, 3) an alkyl radical in Cι-C ₂₀ optionally substituted with an OR group ₅ , 4 ) a C ¹¹ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a Hyu heterocycle and / or being optionally attached to a C ¹² ring of 4 to 7 atoms, these C ¹¹ and C ¹² rings can include a carbonyl function or thiocarbonyl and / or at least one substituent A ₃ chosen from OR, CF ₃ , a halogen, a C ₁ -C ₂₀ alkyl radical; f) R ₅ and R ' ₅ are independently chosen from: 1) hydrogen, 2) a Cι-C ₂₀ alkyl radical; g) Hyi, Hy ₂ , Hy ₄ to Hy ₈ , Hy ₁₀ and Hyu independently represent a heterocycle of 4 to 7 atoms which may contain from 1 to 4 heteroatoms chosen from N, O, S and their associations and / or contain a carbonyl function or thiocarbonyl, h) Hy ₉ represents a heterocycle of 4 to 15 atoms which may contain from 1 to 5 heteroatoms chosen from N, O, S and their associations and / or contain a carbonyl or thiocarbonyl function.

27. Composition according to the preceding claim, characterized in that R ^ represents hydrogen and R ₂ represents one of the following groups: - a saturated C ₁ -C ₁₀ alkyl radical optionally substituted by one or two AL substituents - a saturated hydrocarbon cycle of 3 to 6 carbon atoms, - a saturated or unsaturated Hyi heterocycle with 5, 6 or 7 atoms, comprising from 1 to 2 heteroatoms chosen from O, N and S and optionally a carbonyl function and / or from one to four substituents A ′ ₂ , - a phenyl ring in particular substituted by one or two substituents A " ₂ chosen from a halogen, N0 ₂ , OCF ₃ , CF ₃ , OR ₄ , OCH ₂ R ₄ , COOR ₄ , a C ₁ -C ₁₀ alkyl radical, an aromatic hydrocarbon or heterocyclic ring , - a phenyl ring joined to one or two hydrocarbon or heterocyclic rings of 5 to 6 atoms, thus forming condensed rings.

28. Composition according to claim 26 or 27, characterized in that Hy ₁ represents a heterocycle chosen from azetidine, pyrrole, dihydropyrrole, pyrrolidine, furan, dihydrofuran, tetrahydrofuran, thiophene, dihydrothiophene, tetrahydrothiophene, imidazole, dihydroimidazole, imidazolid , dihydropyrazole, pyrazolidine, oxazole, dihydro-oxazole, oxazolidine, isoxazole, dihydro-isoxazole, isoxazolidine, isothiazole, dihydro-isothiazole, isothiazolidine, triazole, dihydrotriazole, triazolidine, tadadole, thiadiazole, dihydro-diazide , pyridine, dihydropyridine, tetrahydropyridine, piperidine, pyran, dihydropyran, tetrahydropyran, pyrimidine, dihydropyrimidine, tetrahydropyrimidine, piperazine, pyridazine, pyrazine, triazine, morpholine, azepine, diazepine.

29. Composition according to one of claims 26 to 28, characterized in that R ₃ represents one of the following groups: - a hydrocarbon ring, optionally substituted by one or more substituents A '" ₂ chosen from a phenyl radical, COOR ₄ , OR ₄ , COR ₄ , CN, a heterocycle with 5 or 6 atoms comprising from 1 to 2 heteroatoms chosen from O, N and S, a halogen, a phenyl radical optionally substituted by CN, a C 1 -C alkyl radical, with R ₄ representing a hydrogen or a d-Cio alkyl radical, - a phenyl ring joined to one or two C ⁴ hydrocarbon or heterocyclic rings, of 5 to 6 atoms, the C ₄ ring or rings optionally comprising a carbonyl function and / or being optionally substituted by a C 10 alkyl radical, this phenyl and this or these other C ⁴ rings forming condensed rings - a C 10 alkyl radical optionally substituted by one or two substituents A _L

30. Composition according to one of claims 26 to 29, characterized in that the heterocycles Hy ₂ , Hy ₄ , Hy _6l Hy ₇ , Hy ₈ , Hy ₉ , Hy ₁₀ and Hy ^ independently represent the azetidine, pyrrole, dihydropyrrole cycles , pyrrolidine, furan, dihydrofuran, tetrahydrofuran, thiophene, dihydrothiophene, tetrahydrothiophene, imidazole, dihydro-imidazole, imidazolidine, thiazole, dihydrothiazole, thiazolidine, pyrazole, dihydropyrazole, isoxole diazole, oxazole , isothiazole, dihydro-isothiazole, isothiazolidine, triazole, dihydrotriazole, triazolidine, oxadiazole, dihydro-oxadiazole, oxadiazolidine, thiadiazole, dihydrothiadiazole, thiadiazolidine, tetrazoleyryridine, pyrethyridine, tetrahydropyridine, tetrahydropyridine, tetrahydropyridine, tetrahydropyridine, tetrahydropyridine , piperazine, pyridazine, pyrazine, triazine, morpholine, azepine, diazepine or crown ether 15-C-5 for Hy ₉ .

31. Composition according to one of claims 26 to 30, characterized in that the heterocycles Hy ₂ , Hy ₄ , Hy ₆ , Hy ₇ , Hy ₈ , Hy ₉ , Hy ₁₀ and Hyu independently represent pyrrole, pyrrolidine, imidazole, furan , thiophene, oxazole, thiazole, isoxazole, isothiazole, oxadiazole, pyrazole, tetrazole, pyridine, pyrimidine, triazole, pyrazine, pyridazine, piperidine, piperazine, morpholine, or crown ether 15-C-5 for Hy ₉ .

32. Composition according to one of claims 26 to 31, characterized in that Ai represents a hydrocarbon ring or a heterocycle comprising 1 to 2 heteroatoms chosen from O and N, this hydrocarbon or heterocyclic ring comprising 5 or 6 atoms and optionally a function carbonyl and or a substituent A ₃ ; or a group chosen from SiR ₄ R ' ₄ R " ₄ , COOR ₄ , NR ₄ R' ₄ , OR ₄ , SR ₄ , CONR ₄ R ' ₄ .

33. Composition according to one of claims 26 to 32, characterized in that A ₃ represents a C- | -C ₁₀ alkyl radical, CF ₃ , a halogen atom, OH or OCH ₃

34. Composition according to one of claims 26 to 33, characterized in that, R ₄ , R ' ₄ , R " ₄ and R'" represent a hydrogen, a phenyl radical or an alkyl radical in

35. Composition according to one of claims 26 to 34, characterized in that H represents a γ-butyrolactone, a piperidine, a 1,3-benzodioxoxle optionally substituted by a CC ₄ alkyl radical.

36. Composition according to one of claims 26 to 35, characterized in that the salt of the compound of formula (I) is a salt chosen from sodium or potassium salts, ammonium salts, zinc salts ( Zn ²⁺ ), calcium (Ca ²⁺ ), copper (Cu ²⁺ ), iron (Fe ⁺ and Fe ³⁺ ), strontium (Sr ² *), magnesium (Mg ²⁺ ), manganese (Mn ²⁺ ), the tri-ethanolamine, mono-ethanolamine, ethanolamine, hexadecylamine and N, N, N ', N'-tetrakis- (hydroxy-propyl-2) ethylene diamine salts, hydroxides, halohydrates, carbonates, hydrogen carbonates, citrates, lactates, glycolates, gluconates, acetates, propionates, fumarates, oxalates, tartrates, sulfates, phosphates, hydrogen phosphates.

37. Composition according to one of claims 26 to 36, characterized in that the 2-oxy-acetamide compound is in the form of hydrate.

38. Composition according to one of claims 26 to 37, characterized in that the 2-oxy-acetamide compound satisfies the following formula or one of its corresponding salts and / or solvates:

in which: α) Ru is chosen from: 1) a CC ₁₀ alkyl radical optionally substituted with at least one substituent A ₄ , 2) a C ¹⁵ hydrocarbon ring of 5 to 6 atoms optionally substituted with at least one substituent A ₅ ; β) R ₁₂ is chosen from: 1) a C ₁ -C ₁₀ alkyl radical optionally substituted by at least one substituent A ₄ , 2) a C ¹⁶ hydrocarbon ring of 5 to 6 atoms optionally attached to at least one C ¹⁷ ring from 5 to 6 atoms optionally containing at least one heteroatom to form a Hyι ₇ heterocycle, these cycles C ¹⁶ and C ¹⁷ optionally comprising a carbonyl function and / or being substituted by at least one substituent A ₅ ; γ) A ₄ is chosen from: 1) a C ¹⁸ ring of 5 to 6 atoms optionally containing at least one heteroatom to form a Hyι ₈ heterocycle, this cycle or this heterocycle being optionally substituted by at least one substituent A ₆ chosen from OR ₁ , CF ₃ , halogen, C 1 -C 4 alkyl radical; 2) one of the groups CF ₃ , CN, OR ₁₃ , SR ₁₃ , NR ₁₃ R _'13 , NR ₁₃ C (= NR' ₁₃ ) NR " ₁₃ R '" ₁₃ , CORι ₃ , COOR ₁₃ , CONR ₁₃ R' ₁₃ , NR ₁₃ COR _'13 , NRι ₃ CONR' ₁₃ R " ₁₃ , SO ₂ NR ₁₃ R _'13 , NRι ₃ SO ₂ R'ι ₃ , SO ₂ Rι ₃ , SiRι ₃ R'ι ₃ R" ι ₃ , SO ₃ H, where Rι ₃ , R'ι ₃ , R "ι ₃ and R '" ι ₃ independently represent a hydrogen or a C ^ C alkyl radical; δ) A _s is chosen from: 1) a halogen, 2) one of the groups CF ₃ , CN, OR ₁₅ , SR ₁₅ , NRι ₅ R'ι ₅ , OCOR15, COR ₁₅ , COOR ₁₅ , S0 ₂ R ₁₅ , SiR ₁₅ R'i5R "i5, N0 ₂ , OCF ₃ , where R15, R'15 and R" ₁₅ independently represent a hydrogen or an alkyl radical in C Cι ₀ optionally substituted by a phenyl radical, 3) an alkyl radical in CrC optionally substituted by an OR group ₁₄ , 4) a C ¹⁹ ring of 5 to 6 atoms optionally containing at least one heteroatom to form a Hyι ₉ heterocycle and / or possibly comprising a carbonyl function; ε) R ₁₄ is chosen from: 1) hydrogen, 2) a Cι-C ₁₀ alkyl radical; η) Hy ₁₇ , Hy ₁₈ , and Hy ₁₉ independently represent a heterocycle of 5 to 6 atoms which may contain from 1 to 4 heteroatoms chosen from N, O, S and their associations and / or contain a carbonyl function.

39. Composition according to one of claims 26 to 38, characterized in that the 2-oxy-acetamide compound satisfies one of the following formulas (II) to (V) or one of the salts and / or solvates correspondent:

Formula (II):

Formula (III):

Formula (IV)

Formula (V)

in which :

(i) R7 and R8 independently represent: 1) hydrogen, 2) halogen F or Cl, 3) one of the groups CF ₃ , CN, OR ₄ , SR ₄ , NHR ₆ , NR ₆ R ' ₆ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , S0 ₂ R ₄ , SiR ₄ R ' ₄ R " ₄ , OCF ₃ , where R ₄ , R' ₄ and R" ₄ independently represent a hydrogen or a Cι-C ₂ alkyl radical o optionally substituted by a phenyl radical and where R ₆ and R ' ₆ represent an alkyl radical in CC ₂₀ optionally substituted by a phenyl radical, 4) an alkyl radical in Cι-C ₂₀ optionally substituted by an OR ₅ group where R5 represents a hydrogen or a Cι-C ₂₀ alkyl radical, 5) a C ¹¹ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a Hyu heterocycle and / or being optionally attached to a C ¹² ring of 4 to 7 atoms, these cycles C ¹¹ and C ¹² possibly comprising a carbonyl or thiocarbonyl function;

(ii) Z represents one of the following cycles and heterocycles

(iii) X and Y independently represent a hydrogen or A ₂ or can form a C ring joined from 4 to 7 atoms and better still from 5 to 6 atoms, optionally comprising at least one heteroatom chosen from N, O, S and their associations, and being optionally substituted by at least one substituent A ₂ and optionally attached to another C ¹⁴ ring;

(iv) A represents one of the following three groups:

(v) R ₃ has the same meaning as given for formula (I); provided that when Z represents the dibenzofuran heterocycle, X and Y independently represent: 1) hydrogen, 2) halogen, 3) one of the groups CF ₃ , CN, OR ₉ , SR ₄ , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR ₄ R ' ₄ R " ₄ , N0 ₂ , OCF ₃ , where R ₄ , R' ₄ and R" ₄ independently represent a hydrogen or an alkyl radical in CC ₂₀ optionally substituted by a phenyl radical and where Rg represents a hydrogen or a C ₂ -C ₂₀ alkyl radical optionally substituted by a phenyl radical, 4) a C ₂ -C ₂₀ alkyl radical optionally substituted by an OR ₅ group , 5) a C ring of 4 to 7 atoms possibly containing at least one heteroatom to form a Hyu heterocycle and / or being optionally attached to a C ¹² ring of 4 to 7 atoms, these C ¹¹ and C ¹² rings being able to include a function carbonyl or thiocarbonyl; or provided that when Z represents the cycle:

X and Y independently represent: 1) hydrogen, in this case X is different from Y 2) fluorine, 3) one of the groups OR ₁₀ , SR ₄ , NR ₄ R ' ₄ , OCOR ₄ , COR, CSR ₄ , COOR ₆ , SiR ₄ R ' ₄ R ", OCF ₃ , where R, R' ₄ and R" ₄ independently represent a hydrogen or an alkyl group in CC ₂₀ optionally substituted by a phenyl radical, where R ₆ represents an alkyl radical in C ^ C _∑ o optionally substituted by a phenyl radical and where R ₁₀ represents a hydrogen or a benzyl radical or a C ₃ -C ₂₀ alkyl radical optionally substituted by a phenyl radical, 4) a C ₂ -C ₂₀ alkyl radical optionally substituted by an OR ₅ , 5) group X and Y can also form a 5-membered C ¹³ ring (or atom) optionally containing one or two oxygen atoms and possibly being joined to another C ¹⁴ ring.

40. Composition according to one of claims 26 to 39, characterized in that the compound of formula (I) satisfies one of the following formulas:

Compound 3

Compound 5

Compound 6

Compound 8

Compound 9

Compound 10

Compound 12

Compound 13

Compound 18

Compound 19

Compound 21

Compound 23

Compound 24

Compound 28

Compound 32

Compound 34

Compound 35

41. Composition according to one of claims 26 to 40, 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.

42. Composition according to one of claims 26 to 41, characterized in that it is in the form of a hair cream or lotion, shampoo, conditioner, hair mascara or for eyelashes.

43. Composition according to one of claims 26 to 42, characterized in that it is in the form of aqueous, alcoholic or hydro-alcoholic solution or suspension.

44. Composition according to one of claims 26 to 43, characterized in that it contains other ingredients chosen from solvents, thickeners or gelling agents of aqueous phase or of oily phase, coloring matters soluble in 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 (I ), their mixtures.

45. Composition according to one of claims 26 to 44, characterized in that it also contains at least one active agent chosen from proteins or protein hydrolysates, amino acids, polyols, urea, l 'allantoin, sugars and sugar derivatives, water-soluble vitamins, plant extracts, hydroxy acids; retinol and its derivatives, tocopherol and its derivatives, essential fatty acids, ceramides, essential oils, salicylic acid derivatives, hydroxy acid esters, phospholipids, their mixtures.

46. Composition according to one of claims 26 to 45 characterized in that it contains at least one additional active compound promoting regrowth and / or limiting the fall of keratin fibers.

47. Composition according to the preceding claim, characterized in that the additional active compound is chosen from aminexil, 6-0- (9Z, 12Z) -octadeca-9,12- dienoyljhexapyranose, lipoxygenase inhibitors, inhibitors of bradykinin, prostaglandins and their derivatives, prostaglandin receptor agonists or antagonists, non-prostanoic prostaglandin analogs, vasodilators, antiandrogens, cyclosporins and their analogs, antimicrobials, anti-inflammatories, retinoids, chloride benzalkonium, 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, pyro acid esters glutamic, hexosaccharide or acyl-hexosaccharic acids, substituted aryl ethylenes, N-acylated amino acids, flavonoids, ascomycin derivatives and analogs, histamine antagonists, saponins, proteoglycanase inhibitors, agonists and estrogen antagonists, pseudoterins, cytokines and growth factor promoters, IL-1 or IL-6 inhibitors, IL-10 promoters, TNF inhibitors, vitamins, benzophenones, hydantoin, retinoic acid, antipruritic agents, antiparasitics, antifungals, calcium antagonists, hormones, triterpenes, antiandrogenic agents, steroidal or non-steroidal inhibitors of 5-α-reductases, potassium agonists, agonists of the FP receptor, their mixtures.

48. Composition for caring for and / or making up keratin fibers, comprising in a physiologically acceptable medium, in particular a cosmetic medium, at least one compound of formula (I) or one of its salts and / or its solvates and at least an additional active compound promoting the regrowth of keratin fibers and / or limiting their fall, chosen from aminexil, agonists of the FP receptor, prostaglandins and their derivatives, and vasodilators.

49. Composition according to one of claims 46 to 48, characterized in that the additional active compound is chosen from aminexil, minoxidil, latanoprost, acid (5E) -7 - ((1 R, 2R, 3R, 5S) -3,5-dihydroxy-2 - [(3R) -3-hydroxy-5-phenylpentyl] cyclopentyl} - nept-5-enoique, butaprost and travoprost.

50. Process for the cosmetic treatment of human keratin fibers and / or of the skin from which said fibers emerge, with a view to improving their condition and / or their appearance, characterized in that it consists in applying to keratin fibers and / or the skin, a cosmetic composition comprising at least one compound of formula (I) or one of its salts and / or its solvates, to leave the latter in contact with the keratin fibers and / or the skin from which said fibers emerge, and optionally rinsing said fibers and / or said skin.

51. Process for cosmetic treatment of the hair and / or scalp, characterized in that it consists in applying to the hair and / or the scalp, a cosmetic composition comprising an effective amount of at least one compound of formula (I) or one of its salts and / or its solvates, to leave it in contact with the hair and / or the scalp, and optionally to rinse.

52. Process for cosmetic care and / or make-up of human eyelashes, with a view to improving their condition 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 / or one of its solvates and to leave the latter in contact with the eyelashes and / or the eyelids.

53. Compound 2-oxy-acetamide, characterized in that it satisfies one of the following formulas (II) to (V) or one of the corresponding salts and / or solvates:

Formula (II):

Formula (III):

Formula (IV)

Formula (V)

in which : (i) R7 and R8 independently represent: 1) hydrogen, 2) halogen F or Cl, 3) one of the groups CF ₃ , CN, OR ₄ , SR ₄ , NHR ₆ , NR ₆ R ' ₆ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , S0 ₂ R ₄ , SiR ₄ R ' ₄ R " ₄ , OCF ₃ , where R ₄ , R' ₄ and R" ₄ independently represent hydrogen or an optionally substituted CC ₂₀ alkyl radical by a phenyl radical and where R ₆ and R ' ₆ represent a C ₁ -C ₂₀ alkyl radical optionally substituted by a phenyl radical, 4) a C ^ C _alk alkyl radical optionally substituted by an OR ₅ group where R5 represents a hydrogen or an alkyl radical in CC ₂₀ , 5) a C ¹¹ ring of 4 to 7 atoms optionally containing at least one heteroatom to form a Hyu heterocycle and / or being optionally attached to a C ¹² ring of 4 to 7 atoms, these C ¹¹ and C ¹² rings which may include a carbonyl or thiocarbonyl function;

(ii) Z represents one of the following cycles and heterocycles:

(iii) X and Y independently represent a hydrogen or A ₂ or can form a C ¹³ ring joined from 4 to 7 atoms and better still from 5 to 6 atoms, optionally comprising at least one heteroatom chosen from N, O, S and their associations , and being optionally substituted by at least one substituent A ₂ and optionally attached to another C ¹⁴ ring;

(iv) A represents one of the following three groups

(v) R ₃ has the same meaning as given for formula (I); provided that when Z represents the dibenzofuran heterocycle, X and Y independently represent: 1) hydrogen, 2) halogen, 3) one of the groups CF ₃ , CN, OR ₉ , SR ₄ , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , S0 ₂ R ₄ , SiR ₄ R ' ₄ R " ₄ , N0 ₂ , OCF ₃ , where R ₄ , R' ₄ and R" ₄ independently represent hydrogen or an alkyl radical in CC ₂₀ optionally substituted by a phenyl radical and where R ₉ represents a hydrogen or an alkyl radical in C ₂ -C ₂₀ optionally substituted with a phenyl radical, 4) an alkyl radical in C ₂ -C ₂₀ optionally substituted with an OR group ₅ , 5) a C ring of 4 to 7 atoms optionally containing at least one heteroatom to form a Hyu heterocycle and / or being optionally attached to a C ¹² ring of 4 to 7 atoms, these C ¹¹ and C ¹² rings may include a carbonyl or thiocarbonyl function; or provided that when Z represents the cycle:

X and Y independently represent: 1) hydrogen, in this case X is different from Y 2) fluorine, 3) one of the groups OR ₁₀ , SR ₄ , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₆ , SiR ₄ R ' ₄ R " ₄ , OCF ₃ , where R, R' and R" independently represent hydrogen or a C -C ₂₀ alkyl radical optionally substituted by a phenyl radical, where R ₆ represents a radical CC ₂₀ alkyl optionally substituted by a phenyl radical and where Rio represents a hydrogen or a benzyl radical or a C ₃ -C ₂₀ alkyl radical optionally substituted by a phenyl radical, 4) an optionally substituted C ₂ -C ₂₀ alkyl radical by an OR ₅ , 5) group X and Y can also form a 5-membered C ¹³ ring (or atom) possibly containing one or two oxygen atoms and possibly being joined to another C ¹⁴ ring.

54. Compound according to claim 53, characterized in that it satisfies one of the following formulas:

Compound 2

Compound 3

Compound 12

Compound 13

Compound 21