JP2007533708A - 2-Oxy-acetamide compounds, their use and compositions for delaying stimulation or induction and / or loss of keratin fiber growth - Google Patents

Abstract

The present invention relates to the following 2-oxy-acetamide compounds, their salts and / or solvates (II) (III) (IV) (V) as inhibitors of 15-PGDH, wherein: (i) R7 and R8, H, _{halogen, CF 3, CN, oR 4} , 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 represents OCF ₃ and R ₄ , R ′ ₄ , R ″ ₄ , R ₆ , R ′ ₆ are alkyl optionally substituted by H or phenyl, optionally substituted Alkyl represents a (hetero) ring optionally fused to another ring; (ii) Z represents (ii); (iii) X and Y represent H or A ₂ or optional (Iv) A represents (iv); (v) R ₃ represents an optionally substituted alkyl, substituted and / or fused to another ring; Represents a (hetero) ring optionally fused to another ring, said ring being optionally substituted; And (vi) A ₂ is _{halogen, 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 , optionally substituted alkyl, (hetero) ring optionally fused to another ring, rings C ¹¹ and C ¹² can be substituted.

Description

  The present invention relates to a composition for caring for or making up keratin fibers, said composition being effective in increasing the density of the fibers and / or improving their appearance. Of 2-oxyacetamide compound. More particularly, the present invention relates to compositions for caring for or making up hair or eyelashes, delaying the induction and / or irritation and / or loss of their growth. The present invention also relates to novel 2-oxyacetamide compounds and keratin fibers, particularly stimulating hair growth and / or cosmetic treatment methods for delaying their loss.

  Human keratin fibers to which the present invention is applied are in particular head hair, eyebrows, eyelashes, beard, mustache and pubic hair. The invention more particularly applies to human hair and / or eyelashes.

  In particular, the present invention relates to compositions for topical application that care and / or make up hair or eyelashes, which compositions increase their density and / or their appearance. In order to improve the above, a 2-oxyacetamide compound is contained.

  Hair growth and hair regeneration are mainly determined by the activity of the hair follicles and their matrix environment. Their activity is periodic and essentially comprises three phases: the developmental phase, the degenerative phase and the resting phase.

  The developmental period (active or proliferative), which lasts for several years, during which the hair becomes longer, is followed by a very short transient degenerative period lasting a few weeks. During this period, the hair undergoes changes, the follicles atrophy, and the skin implantation appears progressively higher.

  A terminal or resting period lasting a few months corresponds to the resting period of the follicle and the hair end due to shedding. At the end of this resting phase, new follicles are regenerated in situ and another cycle begins.

  Thus, the hair is under permanent regeneration, out of the approximately 150 000 hairs that make up the hair, about 10% are in the rest period and are replaced within a few months.

  It can be estimated that the natural loss or loss of hair averages a few hundred per day under normal physiological conditions. This process of permanent physical regeneration undergoes natural changes during aging, hair becomes thinner and their cycles become shorter.

  In addition, various causes can cause substantial, primary or permanent loss of hair. During late pregnancy (postpartum), there can be hair loss and disability during malnutrition or imbalance of the diet, during physiological stress, or during hormonal dysfunction that is in the case of helplessness or menopause or late menopause. It can also be hair loss and damage associated with seasonal phenomena.

  It can also be an alopecia event that is essentially due to hair regeneration disorders, occurring in the first step in accelerating the cycle frequency for loss of quantity followed by hair quality. This continuous growth cycle gradually converts to depigmentation, resulting in progressively thinner and progressively shorter hair. In certain areas, particularly men, the temporal or frontal head is preferentially affected, and sporadic alopecia at the top of the head is seen in women.

  The term alopecia also encompasses diseases of the entire family of hair follicles, the end result being permanent, partial or total loss of hair. This is more particularly the case for androgenic alopecia. In many cases, premature loss of hair occurs in individuals given a genetic predisposition; therefore, this is a situation of Andro-Chrono-Genetic Alopecia. This form of alopecia particularly affects men.

  In skin diseases with scalp inflammatory elements such as psoriasis or seborrheic dermatitis, hair loss is greatly enhanced or results in a highly destructive follicular cycle.

  The cosmetic and pharmaceutical industry has, for many years, continued to explore compositions for removing or reducing alopecia, particularly those that induce or stimulate hair growth or reduce its loss. .

  In this view, compositions containing a wide variety of active agents have already been proposed, for example 2,4-diamino-6 described in US Pat. No. 4,139,619 and US Pat. No. 4,596,812. -Piperidinopyridine 3-oxide, or "minoxidil" or the documents EP 0 353 123, EP 0 356 271, EP 0 408 442, EP 0 522 964, EP 0 420 707, EP 0 459 890 and EP 0 519 819 There are numerous derivatives thereof, such as those described in.

  Clinical studies have shown that PGF2-α analogs have the property of inducing human and animal hair and eyelash growth (Murray A. and Johnstone MD, 1997, Am. J. Opht., 124 (4), pages 544-547). In humans, studies performed on the scalp have shown that prostaglandin E2 analogs (biprostol) have the property of increasing hair density (Roenigk HH, 1988, Clinic Dermatol., 6 (4), pages 119-121).

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

  However, prostaglandins are very short biological half-life molecules that act in an autocrine or paracrine manner, reflecting the local and unstable nature of prostaglandins metabolism. (Narumiya S. et al., 1999, Physiol. Rev., 79 (4), pages 1193 to 1226).

  Therefore, it is important to protect the endogenous preservation of PGF2-α and also PGE2 in various compartments of the hair follicle or its direct skin environment in order to maintain and / or increase hair density in humans Conceivable.

  One solution with good results to promote hair growth is the use of lipoxygenase-inhibiting compounds and / or cyclooxygenase-inducing compounds; as a principle, the use of such compounds in other routes Preferentially direct fatty acid metabolism towards the endogenous synthesis of prostaglandins.

  However, to further improve this result, it would be desirable to be able to prolong the activity of prostaglandins involved in growing hair alive.

Furthermore, it is well known that epidermal keratinocytes and hair follicle differentiation programs are clearly different. Thus, hair shaft keratins represent a different family than those expressed in the epidermis (Langbein et al., 2001, J. Biol. Chem. 276: 35123-35132), differentiation such as keratin K ₁ and k ₁₀ Markers are not expressed in hair follicles, especially in the outer sheath (Lenoir et al., 1988, Dev. Biol. 130: 610-620), trichohyalin (O'Guin et al., 1992, J. Invest. Dermatol. 98 : Pp. 24-32) and keratin K6irs (Porter et al., 2001, Br. J. Dermatol. 145: 558-568) are expressed in the hair follicle, not in the epidermis, especially in the inner sheath, expressed in the epidermis It is known that type 1 cyclooxygenase is not expressed in keratinocytes in the hair follicle but expressed in the dermal papilla (Michelet et al., 1997, J. Invest. Dermatol. 108: 205-209).
U.S. Pat.No. 4,139,619 U.S. Pat.No. 4,596,812 EP 0 353 123 EP 0 356 271 EP 0 408 442 EP 0 522 964 EP 0 420 707 EP 0 459 890 EP 0 519 819 WO 98/33497 Murray A. and Johnstone MD, 1997, Am. J. Opht., 124 (4), 544-547 Roenigk HH, 1988, Clinic Dermatol., 6 (4), 119-121 Narumiya S. et al., 1999, Physiol. Rev., 79 (4), 1193-1226 Langbein et al., 2001, J. Biol. Chem. 276: 35123-35132 Lenoir et al., 1988, Dev. Biol. 130: 610-620 O'Guin et al., 1992, J. Invest. Dermatol. 98: 24-32 Porter et al., 2001, Br. J. Dermatol. 145: 558-568. Michelet et al., 1997, J. Invest. Dermatol. 108: 205-209

  The Applicant has now demonstrated that the enzymes specifically involved in the degradation of these prostaglandins are present in the hair dermal papilla, a compartment of hair life determinants. The applicant has now demonstrated the existence of type 1 15-hydroxy-prostaglandin dehydrogenase (abbreviated 15-PGDH) specifically at this level. Applicants have also shown that inhibition of type 1 15-PGDH has a beneficial effect on hair growth.

  As a result, the present invention relates to a hair care composition or hair treatment composition containing at least one specific inhibitor of type 1 15-hydroxy-prostaglandin dehydrogenase and a physiologically acceptable medium.

Type 1 15-PGDH is an important enzyme in the inactivation of prostaglandins, particularly PGF2-α and PGE2, which are important mediators of hair growth and survival. It corresponds to the classification EC 1.1.1.141 and depends on NAD ⁺ . It has been isolated from porcine kidney; its inhibition is particularly seen with the thyroid hormone triiodothyronine at doses much greater than physiological doses. Type 2 15-PGDH itself relies on NADP.

However, to maintain and / or increase the density of human keratin fibers, especially human hair, and / or to reduce the heterogeneity of the diameter of keratin fibers, particularly human hair, type 1 15-PGDH inhibitors It has never been proposed to use it. The term “increasing the density of keratin fibers”, in particular the density of hair, means increasing the number or diameter of hair per cm ^{2 of} keratin fibers, in particular the skin or scalp.

  Applicants have shown that certain 2-oxyacetamide compounds of formula (I) in chlorinated or non-chlorinated forms are surprisingly conferred with favorable activity in improving the density of human keratin fibers. Heading. Furthermore, these compounds have been found to be inhibitors of type 1 15-hydroxy-prostaglandin dehydrogenase.

  Accordingly, an object of the present invention is to provide a keratin fiber containing an effective amount of at least one 2-oxyacetamide compound of formula (I), or a salt and / or solvate thereof, in a physiologically acceptable medium, A composition for hair care and / or makeup in particular, or a mascara composition for topical application:

Where:
a) R ₁ and R ₂ are
1) Hydrogen, where R ₁ is different from R ₂
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) at least 1 to form 3 to 7 hydrocarbon-based ring C ¹ , heterocycle Hy ₂ optionally fused to at least one ring C ² of 4 to 7 atoms a ring C ² optionally containing pieces of heteroatoms, these are rings C ¹ substituted optionally contain a carbonyl functional group or a thiocarbonyl functional group, and / or at least by one substituent a ₂ And ring C ² ,
4) fused to any of four of up to 7 atoms in the ring C ² and has heterocycle Hy _1, in the ring C ² optionally containing at least one hetero atom to form a heterocyclic ring Hy ₂ A ring Hy ₁ and a ring C ² , which possibly contain a carbonyl function or a thiocarbonyl function and / or is substituted by at least one substituent A ₁ ,
5) group C (= NR) R ', C (= NR) NR'R'', COR, CSR, COOR, CONRR', SO 2 R or SO ₂ NRR '
One of, independently selected;
b) R ₃ is
1) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
2) 3 to 7 optionally fused to at least one ring C ⁴ of 4 to 7 atoms optionally containing at least 1 heteroatom to form a heterocycle Hy ₄ a hydrocarbon-based atom in the ring C ^3, these are carbonyl functional group or containing a thiocarbonyl functional group optionally and / or at least one ring C ³ and the ring which is substituted with a substituent a ₂ C ⁴ ,
3) Heterocyclic Hy ₃ selected from pyrrole ring, furan ring, thiophene ring and pyrazole ring optionally fused to ring C ⁵ representing phenyl, pyridine or pyrimidine, optionally substituted by at least one substituent A ₁ A heterocycle Hy ₃ and a ring C ⁵ ,
4) Unlike Hy ₃ , a heterocycle Hy ₅ optionally fused to a ring C ⁶ of from 4 to 7 atoms, which is used to form the heterocycle Hy ₆ ⁶ optionally contains at least one heteroatom, optionally containing a carbonyl function or a thiocarbonyl function and / or substituted with at least one substituent A ₁ and ring Hy ₅ and ring C ⁶ , selected from;
c) R, R 'and R''are:
1) hydrogen,
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) 4 to ₇ optionally containing at least one heteroatom to form heterocycle Hy ₇ and / or optionally containing at least one heteroatom to form heterocycle Hy ₈ a ring C ⁷ atoms from four fused to an optionally ring C ⁸ atoms up pieces up to 7, which is optionally substituted by at least one substituent a _1, or carbonyl function Independently selected from ring C ⁷ and ring C ⁸ , optionally containing a thiocarbonyl functionality;
d) A ₁ is:
1) halogen,
2) C ₁ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
3) optionally contain at least one hetero atom to form a heterocyclic ring Hy _9, and / or 15 in atom ring C ¹⁰ of from four to seven from four fused to optionally Ring C ⁹ of atoms up to and including at least one substituent A selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C ₁ -C ₂₀ alkyl groups Ring C ⁹ and ring C ¹⁰ optionally containing ₃ ,
4) R ₄ , R ′ ₄ , R ″ ₄ and R ′ ″ ₄ are independently C ₁ -C ₂₀ alkyl optionally substituted with hydrogen or heterocyclic Hy ₁₀ or CONR ₅ R ′ ₅ group 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 , selected from Si (OR ₄ ) (OR' ₄ ) OR '' ₄ , and one of SO ₃ H;
e) A ₂ is:
1) halogen,
2) R ₄ , R ′ ₄ and R ″ ₄ independently represent a group CF ₃ , CN, OR ₄ , SR ₄ which represents a C ₁ -C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group. , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR ₄ R' ₄ R '' ₄ , one of NO ₂ and OCF ₃ ,
3) C ₁ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
4) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ A ring C ¹¹ of atoms up to and including at least one substituent A selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C ₁ -C ₂₀ alkyl groups Selected from ring C ¹¹ and ring C ¹² , optionally including ₃ ;
f) R ₅ and R ' ₅ are
1) hydrogen,
2) C ₁ ~C ₂₀ alkyl group, independently selected from;
g) Hy ₁ , Hy ₂ , Hy ₄ to Hy ₈ , Hy ₁₀ and Hy ₁₁ are independently selected from N, O and S and combinations thereof, and / or have a carbonyl or thiocarbonyl function. Represents a heterocycle of 4 to 7 atoms potentially containing 1 to 4 heteroatoms inclusive;
h) Hy ₉ is selected from N, O and S and combinations thereof and / or from 4 possibly containing 1 to 5 heteroatoms containing a carbonyl function or a thiocarbonyl function Represents a heterocycle of up to 15 atoms.

  The present invention also particularly relates to the cosmetic use of at least one 2-oxyacetamide compound of formula (I), or a salt and / or solvate thereof, as defined above, keratin fibers, in particular human keratin fibers. And / or their use as agents for inducing and / or stimulating proliferation and delaying their loss and / or increasing their density.

  An object of the present invention is also to provide at least one 2- of formula (I) in compositions for increasing their loss delay and / or their density for the care or treatment of keratin fibers, in particular human keratin fibers. Cosmetic use of oxyacetamide compounds, or salts and / or solvates thereof. The composition can also maintain keratin fibers in good condition and / or improve their appearance.

  One object of the present invention is also to induce and / or stimulate and / or delay the loss of and / or increase the density of said fibers for the care or treatment of keratin fibers, in particular human keratin fibers Use of at least one 2-oxyacetamide compound of formula (I), or a salt and / or solvate thereof, for the preparation of a composition to be prepared.

  The invention also applies to keratin fibers of mammals (eg, dogs, horses or cats).

  Human keratin fibers to which the present invention is applied are in particular head hair, eyebrows, eyelashes, beard, mustache and pubic hair. The invention more particularly applies to human hair and / or eyelashes.

  Thus, the present invention also provides at least one of the formula (I) in a human cosmetic hair care composition for the treatment of delayed hair loss and / or increased density and / or treatment of andro-chrono-genetic alopecia To the cosmetic use of 2-oxyacetamide compounds or salts and / or solvates thereof. One object of the present invention is also a composition for human hair that induces and / or stimulates hair growth and / or increases its delayed loss and / or their density and / or treats androgenic alopecia For the preparation of at least one 2-oxyacetamide compound of formula (I), or a salt and / or solvate thereof.

  The present invention also relates to a human cosmetic hair care composition for treating naturally occurring alopecia, in particular androgenic alopecia, at least one 2-oxyacetamide compound of formula (I), or a salt thereof and / or Or at least one 2-oxyacetamide compound of formula (I) for the cosmetic use of solvates and for the preparation of human hair care compositions for the treatment of naturally occurring alopecia, in particular androgenic alopecia Or the use of salts and / or solvates thereof. Thus, the composition can maintain the hair in good condition and / or combat natural hair loss, especially in men.

  One subject of the present invention is also a cosmetic composition for inducing and / or stimulating the growth of the eyelashes and / or increasing the density for the care and / or make-up of human eyelashes, at least one of the formula (I) For the cosmetic use of certain 2-oxyacetamide compounds, or salts and / or solvates thereof, and for the induction and / or stimulation of eyelash growth and / or increase in density for the care or treatment of human eyelashes Use of at least one 2-oxyacetamide compound of formula (I) for the preparation of a composition for Thus, the composition can maintain eyelashes in good condition and / or improve their condition and / or appearance.

  One subject of the present invention is also at least one 2-oxyacetamide compound of formula (I), or a salt and / or solvate thereof, especially as an inhibitor of type 1 15-hydroxyprostaglandin dehydrogenase in human skin. Is the use of. One subject of the present invention is also at least one 2-oxy of formula (I) for the manufacture of a composition for treating disorders associated with the presence of type 1 15-hydroxyprostaglandin dehydrogenase, especially in men. Use of an acetamide compound, or a salt and / or solvate thereof.

  The subject of the present invention is also a cosmetic method for treating the skin in which said fibers appear, such as human keratin fibers (especially hair or eyelashes) and / or scalp, and eyelids, which comprises said keratin fibers and / or said The cosmetic composition comprises at least one compound of formula (I) or a salt and / or solvate thereof, the composition comprising keratin fibers in which said fibers appear and / or Contacting the skin and optionally rinsing the fibers and / or the skin.

  In fact, this treatment method has strong cosmetic properties as long as it can improve the aesthetics of human keratin fibers, especially hair and eyelashes, by providing greater vitality and improved appearance. In addition, it can be used daily for several months without a medical prescription.

  More particularly, one object of the present invention is a cosmetic method for caring for human hair and / or scalp to improve their condition and / or appearance, which is applied to said hair and / or said scalp. The cosmetic composition comprises at least one compound of formula (I) or a salt and / or solvate thereof, wherein the composition is contacted with the hair and / or scalp, and the hair and / or scalp Is optionally rinsed.

  The subject of the present invention is also a cosmetic method for caring for and / or making up human eyelashes in order to improve their condition and / or appearance, comprising applying to the eyelashes and / or eyelids, The composition comprises at least one compound of formula (I) or a salt and / or solvate thereof, characterized in that the composition is contacted with eyelashes and / or eyelids. The mascara composition can be applied alone or as a base for a standard colored mascara and can be removed like a standard colored mascara.

  The subject of the invention is also a care composition and / or a mascara composition containing a cosmetically acceptable medium for topical application and one compound of formula (I) or a salt and / or solvate thereof. .

  The subject of the present invention is also a physiologically acceptable medium, in particular a cosmetic medium, at least one compound of formula (I) or a salt and / or solvate thereof, and aminexil, an FP receptor agonist. , Prostaglandins and their derivatives, vasodilators, and more particularly aminexyl, minoxidil, latanoprost, (5E) -7-{(1R, 2R, 3R, 5R) -3,5-dihydroxy-2 -[(3R) -3-hydroxy-5-phenylpentyl] cyclopentyl} hepta-5-enoic acid, selected from butaprost and travoprost, promotes regeneration and / or limits loss of human keratin fibers A composition for the care and / or make-up of keratin fibers comprising at least one additional active agent.

  The subject of the present invention is also the cosmetic use of 2-oxyacetamide compounds of formula (I) or salts and / or solvates thereof as agents for protecting the amount and / or activity of prostaglandins in the hair follicle. is there.

  The subject of the present invention is also for the production of a composition that protects the amount and / or activity of prostaglandins in the hair follicle, at least one 2-oxyacetamide compound of the formula (I) or a salt thereof and / Or use solvates.

The subject of the present invention is also a novel 2-oxyacetamide compound satisfying at least one of the following formulas (II), (III), (IV) and (V), or a corresponding salt and / or Or a solvate:
Formula (II):

Formula (III):

Formula (IV):

Formula (V):

Where:
(i) R7 and R8 are independently:
1) hydrogen,
2) F or Cl halogen,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent hydrogen or a saturated C ₁ -C ₂₀ alkyl group optionally substituted by linear or branched, especially phenyl group, R ₆ And R ′ ₆ represents a C ₁ -C ₂₀ alkyl group optionally substituted by a phenyl group, the groups CF ₃ , CN, OR ₄ , SR ₄ , NHR ₆ , NR ₆ R ′ ₆ , OCOR ₄ , COR ₄ , one of CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR ₄ R ' ₄ R'' ₄ , and OCF ₃ ,
4) R ₅ is, C ₁ -C ₂₀ alkyl group which is optionally substituted by hydrogen or a linear or branched, particularly OR ₅ groups represents a saturated C ₁ -C ₂₀ alkyl group,
5) heterocyclic Hy optionally contain at least one heteroatom ₁₁ to form the, and / or 4 of four are fused to optionally atom saturated or unsaturated ring C ¹² of up to seven Ring C ¹¹ of from 1 to 7 atoms, which represents ring C ¹¹ and ring C ¹² possibly containing a carbonyl function or a thiocarbonyl function:
(ii) z is the following ring and heterocycle:

Represents one of the following;
(iii) X and Y independently represent hydrogen or the above defined (e.g. formula (I)) A ₂ or a condensed saturated or unsaturated ring of 4 to 7 atoms C ¹³ can be formed, which optionally contains at least one heteroatom, is optionally substituted with at least one substituent A ₂ and is optionally fused to another saturated or unsaturated ring C ^14. Represents ring C ¹³ ;
When Z represents a dibenzofuran heterocycle, X and Y are independently:
1) hydrogen,
2) Halogen, such as F or Cl,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent hydrogen or a linear or branched, especially saturated C ₁ -C ₂₀ alkyl group optionally substituted by a phenyl group, R ₉ Is a group CF ₃ , CN, OR ₉ , SR ₄ , NR ₄ R ′ ₄ , representing hydrogen or a linear or branched, especially saturated C ₂ -C ₂₀ alkyl group optionally substituted by a phenyl group, OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR ₄ R ' ₄ R'' ₄ , one of NO ₂ and OCF ₃ ,
4) linear or branched, in particular saturated C ₂ -C ₂₀ alkyl group optionally substituted by OR ₅ group,
5) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, provided that they represent ring C ¹¹ and ring C ¹² potentially containing a carbonyl function or a thiocarbonyl function; or
Z, ring:

Represents
X and Y are independently:
1) Hydrogen, in this case X is different from Y
2) Fluorine,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent hydrogen or a saturated C ₁ -C ₂₀ alkyl group optionally substituted by linear or branched, especially phenyl group, R ₆ is a linear or branched, in particular represents a saturated C ₁ -C ₂₀ alkyl group optionally substituted by a phenyl group, R ₁₀ is a hydrogen atom or a benzyl group or a linear or branched, in particular phenyl The group OR ₁₀ , SR ₄ , NR ₄ R ′ ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₆ , SiR ₄ R ′ ₄ R ′ represents a saturated C ₃ -C ₂₀ alkyl group optionally substituted by 'One of ₄ and OCF ₃ ,
4) linear or branched, in particular saturated C ₂ -C ₂₀ alkyl group optionally substituted by OR ₅ group,
5) X and Y can also form a saturated or unsaturated 5-atom ring C ¹³ , optionally containing 1 or 2 oxygen atoms, optionally fused to another saturated or unsaturated ring C ¹⁴ Under the condition that it represents ring C ¹³
(iv) A is the following three groups:

Represents one of
(v) R ₃ has the same definition as described above with respect to formula (I).

  The compounds of formula (II), formula (III), formula (IV) and formula (V) are advantageously inhibitors of type 1 15-PGDH, even better selective inhibitors.

  The term “15-hydroxyprostaglandin dehydrogenase inhibitor” refers to the ability to inhibit or reduce the activity of type 1 15-PGDH enzyme, particularly its human form, and / or prevent or reduce the reaction catalyzed by this enzyme. Or a compound of formula I that can be slowed down.

  According to one advantageous embodiment of the invention, the compound of formula (I) is a specific inhibitor of 15-PGDH; the term “specific inhibitor” refers to the synthesis of prostaglandins, in particular An active agent that has little or no inhibitory activity on the synthesis of PGF2-α or PGE2. According to one particular embodiment of the invention, the 15-PGDH inhibitor has little or no inhibitory activity on the synthesis of prostaglandins, in particular the synthesis of PGF2-α or PGE2. In particular, type 1 15-PGDH inhibitors have little or no inhibitory activity on prostaglandin synthesis (abbreviated as PGF synthase or PGFS).

  In particular, the present applicant has now found that PGF synthase is also expressed in the dermal papilla. Thus, maintenance of effective amounts of prostaglandins at the site of action is provided by a complex biological equilibrium between the synthesis and degradation of these molecules. Thus, when this activity is combined with inhibition of the synthesis of these prostaglandins, it will be less effective due to the exogenous supply of compounds that inhibit catabolism.

Advantageously, the compound of formula (I) in the chloride or non-chloride form, solvate or non-solvate form has an inhibitory activity against 15-PGDH that is higher than the inhibitory activity against PGF synthase. These compounds are referred to as selective inhibitors of 15-PGDH for PGF synthase. In particular, it is determined by the concentration that inhibits the enzyme activity of PGF synthase by 50% (IC _50fs ) relative to the concentration that inhibits the enzyme activity of 15-PGDH by 50% for a given concentration (IC 50 _fs ), respectively. Advantageously, the ratio of inhibitory activity between -PGDH is at least greater than 1, in particular at least equal to 3: 1, 5: 1 or more.

  Unless stated otherwise in the text below, the use of the term `` compound of formula (I) '' means not only a compound of formula (I) but also one of its salts or solvates, in particular hydrates, Or it should be understood as meaning one of its solvates (especially hydrated salts).

  According to the invention, the term “salts of the compound of formula (I)” means organic or inorganic salts of the compound of formula (I).

Examples of inorganic salts that can be used according to the present invention include sodium salts or potassium salts, and ammonium salts, zinc (Zn ²⁺ ) salts, calcium (Ca ²⁺ ) salts, copper (Cu ²⁺ ) salts, Iron (Fe ²⁺ and Fe ³⁺ ), strontium (Sr ²⁺ ), magnesium (Mg ²⁺ ) and manganese (Mn ²⁺ ) salts; hydroxides, hydrohalides (e.g. hydrochlorides), Mention may be made of carbonates, bicarbonates, sulfates, hydrogen phosphates and phosphates.

  Organic salts which can be used according to the invention are, for example, triethanolamine salts, monoethanolamine salts, diethanolamine salts, hexadecylamine salts and N, N, N ′, N′-tetrakis (2-hydroxypropyl) ethylenediamine salts. And organic acids such as citrate, lactate, glycolate, gluconate, acetate, propionate, fumarate, oxalate and tartrate.

  Possible solvates of the compounds of formula (I) may include hydrates, alkoxides or hydroalkoxides.

  According to the invention, the compound of formula (I) is isolated, i.e. in a non-polymeric form.

  According to the present invention, the term “at least one” 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 can be cis or trans isomers or Z or E isomers or a mixture of cis / trans isomers or Z / E isomers. They can also be tautomeric. The compound or compounds can be enantiomers and / or diastereoisomers or mixtures of these isomers, in particular racemic mixtures.

  For the purposes of the present invention, the term “hydrocarbon-based” refers to hydrogen atoms and carbon atom groups.

  For the purposes of the present invention, the term “alkyl group” means a hydrocarbon-based group that can be linear or branched and saturated or unsaturated. In particular, the alkyl group contains 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms. Examples of alkyl groups that can be used in the present invention include methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, n-hexyl group, 2-ethylhexyl group, ethylene group and propylene group. it can.

  Examples of the halogen atom that can be used in the present invention include a chlorine atom, a fluorine atom, and a bromine atom, and even better, a chlorine atom and a fluorine atom.

Rings C ¹ to C ⁴ and rings C ⁶ to C ¹⁴ and heterocycles Hy ₁ , Hy ₂ and Hy ₄ to Hy ₁₁ may be saturated or unsaturated. In particular they contain 5 to 6 atoms. According to one particular mode of the invention, the ring C ⁹ can contain up to 15 atoms and can represent, for example, a crown ether containing 5-CH ₂ CH ₂ O-units. Further, the rings C ¹ , C ³ , C ⁷ , C ⁹ , C ¹¹ , C ¹³ , Hy ₁ , Hy ₃ , Hy ₅ , Hy ₇ , Hy ₉ and Hy ₁₁ may be one of the same or different chemistries or Can be fused to multiple other rings.

  Examples of the saturated hydrocarbon base ring that can be used in the present invention include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. Unsaturated hydrocarbon-based rings that can be mentioned include cyclohexenyl groups and phenyl groups. Examples of the condensed hydrocarbon base ring that can be used in the present invention include a naphthyl group and an azulenyl group. Condensed rings of different properties that can be used in the present invention include benzofuran group, dibenzofuran group, benzothiophene group, benzothiazole group, indole group, benzimidazole group, quinoline group, isoquinoline group, quinazoline group, carboline group, chromene group, carbazole And fluorene groups.

According to the invention, R ₁ and / or R ₂ and / or R ₃ can represent a hydrocarbon-based ring as defined above, but also N, O and S, and combinations thereof Heterocycles containing 1 to 4 heteroatoms selected from the combination can be represented. In addition, these hydrocarbon-based rings or heterocyclic rings optionally contain a carbonyl function or a thiocarbonyl function.

  Examples of rings containing carbonyl or thiocarbonyl functions that can be used in the present invention include the following rings:

Can be mentioned.

According to one particular embodiment of the invention, R ₁ and / or R ₂ is azetidine, pyrrole, dihydropyrrole, pyrrolidine, furan, dihydrofuran, tetrahydrofuran, thiophene, dihydrothiophene, tetrahydrothiophene, imidazole, dihydroimidazole, Imidazolidine, dihydrothiazole, thiazolidine, dihydropyrazole, pyrazolidine, oxazole, dihydrooxazole, oxazolidine, isoxazole, dihydroisoxazole, isoxazolidine, isothiazole, dihydroisothiazole, isothiazolidine, triazole, dihydrotriazole, triazolidine, oxadiazole, Dihydrooxadiazole, oxadiazolidine, thiadiazole, dihydrothiadiazole, thiadiazolidine , Tetrazole, pyridine, dihydropyridine, tetrahydropyridine, piperidine, pyran, dihydropyran, tetrahydropyran, pyrimidine, dihydropyrimidine, tetrahydropyrimidine, piperazine, pyridazine, pyrazine, triazine, morpholine, azepine, heterocycle Hy _1, which is especially selected from diazepin Represents. In particular Hy ₁ represents γ-butyrolactone, piperidine or 1,3-benzodioxazole, which is linear or branched, in particular optionally substituted by a saturated C ₁ -C ₄ alkyl group.

R ₁ represents hydrogen and R ₂ represents the following group:
- linear or branched saturated C ₁ -C ₁₀ alkyl group, for example, one or two substituted methyl groups by group A ₁ is optionally substituted, an ethyl group, butyl group, propyl group, pentyl or hexyl Group,
-Saturated hydrocarbon-based rings of 3 to 6 carbon atoms,
- wherein O, N and S, optionally carbonyl functional groups and / or 1 to 4 substituents A '2 heteroatoms from one selected from _2, 5, 6 or 7 atoms A saturated or unsaturated heterocycle Hy ₁ ,
- halogen (especially fluorine or _{chlorine), NO 2, OCF 3,} CF 3, OR 4, OCH 2 R 4, COOR 4, C 1 ~C 10 alkyl group (e.g., ethyl, propyl in particular saturated, t- butyl , Hexyl or methyl), and a phenyl ring optionally substituted by one or two substituents A '' ₂ selected from a hydrocarbon-based ring or a heterocyclic aromatic ring,
A phenyl ring fused to one or two saturated or unsaturated hydrocarbon-based or heterocyclic rings of 5 to 6 atoms, thus forming a condensed ring, for example an indane ring, carbazole Advantageously, it represents one of a ring, a benzodioxole ring, a fluorene ring or a dibenzofuran ring.

According to the invention, the substituents A ₁ or A ₂ generated by the same ring or the same alkyl group may be the same or different. Furthermore, they may be the same or different with respect to R ₁ , R ₂ and R ₃ . Similarly, R ₄ , R ′ ₄ , R ″ ₄ and R ′ ″ ₄ may be the same or different with respect to substituent A ₂ from the same group, the same group or substituent A ₁ .

In particular, A ₁ represents a hydrocarbon-based ring or heterocycle containing 1 or 2 heteroatoms selected from O and N, wherein the hydrocarbon-based ring or heterocycle is 5 to 6 atoms And optionally a carbonyl functional group and / or substituent A ₃ ; or SiR ₄ R ′ ₄ R ″ ₄ , COOR ₄ , NR ₄ R ′ ₄ , OR ₄ , SR ₄ and CONR ₄ R ′ ₄ .

According to one particular embodiment of the invention, R ₄ , R ′ ₄ , R ″ ₄ and R ′ ″ ₄ are hydrogen, a phenyl group or a C ₁ -C ₁₀ alkyl group, for example a methyl group, ethyl Represents a group, t-butyl group, n-butyl group, n-propyl group, isopropyl group or pentyl group.

A ′ ₂ advantageously represents a linear or branched, especially saturated C ₁ -C ₁₀ alkyl group such as methyl.

According to one particular embodiment of the invention, A ₃ is linear or branched, in particular a saturated C ₁ -C ₁₀ alkyl group such as methyl, CF ₃ , a halogen atom such as F, OH or OCH _3. Represents.

According to one particular embodiment of the invention, R ₃ is azetidine, dihydropyrrole, pyrrolidine, dihydrofuran, tetrahydrofuran, dihydrothiophene, tetrahydrothiophene, imidazole, dihydroimidazole, imidazolidine, thiazole, dihydrothiazole, thiazolidine, dihydro Pyrazole, pyrazolidine, oxazole, dihydrooxazole, oxazolidine, isoxazole, dihydroisoxazole, isoxazolidine, isothiazole, dihydroisothiazole, isothiazolidine, triazole, dihydrotriazole, triazolidine, oxadiazole, dihydrooxadiazole, oxadiazolidine, Thiadiazole, dihydrothiadiazole, thiadiazolidine, tetrazole, dihydropyridine Tetrahydropyridine, piperidine, pyran, dihydropyran, tetrahydropyran, represented pyrimidine, dihydropyrimidine, tetrahydropyrimidine, piperazine, pyridazine, pyrazine, triazine, morpholine, heterocycle Hy ₅ selected from azepine and diazepine.

R ₃ is the following group:
-To saturated or unsaturated containing phenyl group, COOR ₄ , OR ₄ , COR ₄ , CN, 5 or 6 atoms, containing 1 or 2 heteroatoms selected from O, S and N heterocycle, e.g., pyrrole or imidazole, halogen (fluorine or chlorine), CN, a linear or branched, in particular saturated C ₁ -C ₁₀ alkyl group, for example, ethyl, methyl, isopropyl, by isobutyl or t- butyl, A saturated or unsaturated hydrocarbon-based ring optionally substituted with one or more substituents A ′ '' ₂ selected from optionally substituted phenyl groups, wherein R ₄ is hydrogen or a line Jo or branched, in particular saturated C ₁ -C ₁₀ alkyl group, for example, a methyl group or an ethyl group,
A phenyl ring fused to one or two saturated or unsaturated 5- to 6-atom hydrocarbon-based or heterocyclic ring C ⁴ , wherein ring C ⁴ optionally contains a carbonyl group , and / or linear or branched, which is optionally substituted in particular saturated C ₁ -C ₁₀ alkyl group, for example by a methyl group or an ethyl group, which, it or by condensing these rings C ^4, A phenyl ring forming a condensed ring such as an indane ring, a benzothiazole ring, a quinoline ring, a carbazole ring, a fluorene ring, a fluorenone ring or a dibenzofuran ring;
Advantageously representing one or two substituents A ₁ , for example one of linear or branched, optionally saturated by a phenyl group, in particular a saturated C ₁ -C ₁₀ alkyl group, for example methyl It is.

Examples of the heterocycles Hy ₂ , Hy ₄ , Hy ₆ , Hy ₇ , Hy ₈ , Hy ₉ , Hy ₁₀ and Hy ₁₁ that can be used in the present invention include azetidine ring, pyrrole ring, dihydropyrrole ring, pyrrolidine ring, furan ring , Dihydrofuran ring, tetrahydrofuran ring, thiophene ring, dihydrothiophene ring, tetrahydrothiophene ring, imidazole ring, dihydroimidazole ring, imidazolidine ring, thiazole ring, dihydrothiazole ring, thiazolidine ring, pyrazole ring, dihydropyrazole ring, pyrazolidine ring, Oxazole ring, dihydrooxazole ring, oxazolidine ring, isoxazole ring, dihydroisoxazole ring, isoxazolidine ring, isothiazole ring, dihydroisothiazole ring, isothiazolidine ring, triazole ring, dihydrotriazole ring, triazolidine ring, ox Sadiazole ring, dihydrooxadiazole ring, oxadiazolidine ring, thiadiazole ring, dihydrothiadiazole ring, thiadiazolidine ring, tetrazole ring, pyridine ring, dihydropyridine ring, tetrahydropyridine ring, piperidine ring, pyran ring, dihydropyran ring, tetrahydro A pyran ring, a pyrimidine ring, a dihydropyrimidine ring, a tetrahydropyrimidine ring, a piperazine ring, a pyridazine ring, a pyrazine ring, a triazine ring, a morpholine ring, an azepine ring, and a diazepine ring or Hy ₉ independently for 15-C-5 crown ether Can be mentioned. Pyrrole ring, pyrrolidine ring, imidazole ring, furan ring, thiophene ring, oxazole ring, thiazole ring, isoxazole ring, isothiazole ring, oxadiazole ring, pyrazole ring, tetrazole ring, pyridine ring, pyrimidine ring, triazole ring, pyrazine ring Pyridazine ring, piperidine ring, piperazine ring or morpholine ring or Hy ₉ is preferably used with 15-C-5 crown ether.

  According to a preferred embodiment of the present invention, the 2-oxyacetamide compound has the following formula (Ia):

Or a salt and / or solvate thereof,
Where:
α) R ₁₁ is:
1) a linear or branched, in particular at least one optionally substituted by substituents A ₄ saturated C ₁ -C ₁₀ alkyl group,
2) selected from a saturated or unsaturated hydrocarbon-based ring C ^{15 of} 5 to 6 atoms, optionally substituted by at least one substituent A ₅ ;
β) R ₁₂ is:
1) a linear or branched, in particular at least one optionally substituted by substituents A ₄ saturated C ₁ -C ₁₀ alkyl group,
2) From 5 optionally fused to at least one saturated or unsaturated ring C ¹⁷ of 5 to 6 atoms optionally containing at least one heteroatom to form a heterocycle Hy ₁₇ 6-saturated or unsaturated hydrocarbon-based ring C ^16, which optionally contains a carbonyl function and / or is substituted by at least one substituent A ₅ and ring C ¹⁶ and ring C ^{16 17} , selected from;
γ) A ₄ is:
1) a 5 to 6 atom saturated or unsaturated ring C ¹⁸ optionally containing at least one heteroatom to form a heterocycle Hy ₁₈ , wherein the ring or these heterocycles are Rings optionally substituted by at least one substituent A ₆ selected from OR ₁₄ , CF ₃ , halogen such as fluorine or chlorine, and linear or branched, especially saturated C ₁ -C ₁₀ alkyl groups C ¹⁸ ,
2) R ₁₃ , R ′ ₁₃ , R ″ ₁₃ and R ′ ″ ₁₃ independently represent hydrogen or a linear or branched, especially saturated C ₁ -C ₁₀ alkyl group, the group 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, one of _{NR 13 COR '13 R''} 13, SO 2 NR 13 R' 13, NR 13 SO 2 R '13, SO 2 R 13, SiR 13 R' 13 R '' 13 and SO ₃ H, Selected from;
δ) A ₅ is:
1) Halogen, such as fluorine or chlorine,
2) R ₁₅ , R ′ ₁₅ and R ″ ₁₅ independently represent a linear or branched, optionally substituted by a hydrogen or phenyl group, in particular a saturated CF _{1 to} C ₁₀ alkyl group, the group CF _3, CN, one of the _{oR 15, SR 15, NR 15} R '15, OCOR 15, COR 15, COOR 15, SO 2 R 15, SiR 15 R' 15 R '' 15, NO 2 and OCF ₃ ,
3) linear or branched optionally substituted by OR ₁₄ groups, particularly saturated C ₁ -C ₁₀ alkyl group,
4) optionally containing at least one hetero atom to form a heterocyclic ring Hy _19, and / or 5 to 6 saturated or unsaturated ring C ¹⁹ atoms, including possibly a carbonyl function, Selected from;
ε) R ₁₄ is:
1) hydrogen,
2) linear or branched, selected especially saturated C ₁ -C ₁₀ alkyl group from;
η) Hy ₁₇ , Hy ₁₈ and Hy ₁₉ potentially contain 1 to 4 heterocycles independently selected from N, O and S and combinations thereof and / or carbonyl functional groups Represents a heterocycle of 5 to 6 atoms including

According to a preferred embodiment of the present invention, the 2-oxyacetamide compound is represented by the following formulas (II) to (V):
Formula (II):

Formula (III):

Formula (IV):

Formula (V):

Satisfying one of them, or the corresponding salt and / or solvate thereof,
Where:
(i) R7 and R8 are independently:
1) hydrogen,
2) F or Cl halogen,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent a C _{1 to} C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group, and R ₆ and R ′ ₆ represent a phenyl group The groups CF ₃ , CN, OR ₄ , SR ₄ , NHR ₆ , NR ₆ R ′ ₆ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO represent an optionally substituted C ₁ -C ₂₀ alkyl group _{1 of 2} R ₄ , SiR ₄ R ' ₄ R'' ₄ , and OCF ₃ ,
4) R5 is, C ₁ -C ₂₀ alkyl group optionally substituted by OR ₅ groups represent hydrogen or C ₁ -C ₂₀ alkyl group,
5) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, which represent ring C ¹¹ and ring C ¹² possibly containing a carbonyl function or a thiocarbonyl function:
(ii) z is the following ring and heterocycle:

Represents one of
(iii) X and Y independently represent hydrogen or A ₂ as defined above with respect to formula (I), or at least one heteroatom selected from N, O and S and combinations thereof From 4 to 7, and even better from 5 to 6, optionally substituted with one or more substituents A ₂ and optionally fused to another ring C ¹⁴ Can form a condensed ring of atoms C ¹³ ;
-When Z represents a dibenzofuran heterocycle, X and Y are independently:
1) hydrogen,
2) Halogen (F or Cl),
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent a C _{1 to} C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group, and R ₉ is optionally substituted with hydrogen or a phenyl group. It represents a C ₂ -C ₂₀ alkyl group substituted, group _{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 , one of NO ₂ and OCF ₃ ,
4) C ₂ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
5) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, provided that they represent ring C ¹¹ possibly containing a carbonyl function or a thiocarbonyl function; or
-Z, ring:

Represents
X and Y are independently:
1) Hydrogen, in this case X is different from Y
2) Fluorine,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent a C _{1 to} C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group, and R ₆ is optionally substituted with a phenyl group. R ₁₀ represents a C ₁ -C ₂₀ alkyl group, and a group OR ₁₀ , SR ₄ , NR ₄ represents a C ₃ -C ₂₀ alkyl group optionally substituted by a hydrogen atom or a benzyl group or phenyl group one of _{R '4, OCOR 4, COR} 4, CSR 4, COOR 6, SiR 4 R' 4 R '' 4 and OCF _3,
4) C ₂ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
5) X and Y can also form a saturated or unsaturated 5-membered (or 5-atom) ring C ¹³ , optionally containing one or two oxygen atoms, and another saturated or unsaturated ring C ¹⁴ On the condition that it represents ring C ¹³ optionally fused to
(iv) A is the following three groups:

Represents a representative one of
(v) R ₃ has the same meaning as described above for formula (I).

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

  To the best of the Applicant's knowledge, 2-oxyacetamide compounds of formula (I) or salts and / or solvates thereof induce and / or stimulate the growth of human keratin fibers, in particular human hair and eyelashes, and / or Prior art literature has been described or suggested that these compounds can be used topically to have the property of delaying their loss or to increase the density of keratin fibers (especially hair and eyelashes). Absent.

  An effective amount of a compound of formula (I) (chlorinated or non-chlorinated, or solvated or non-solvated) is intended to increase the density of the desired result (i.e., keratin fibers, especially hair and eyelashes, or This is equivalent to the amount of compound necessary to obtain Thus, one skilled in the art can assess this effective amount by the nature of the compound used, the person receiving the application and the time of application.

  In the following text, unless stated otherwise, the amounts of the various components in the composition are given as weight percentages relative to the total weight of the composition.

In order to obtain quantities of orders according to the invention, the compounds of formula (I) (salified or non-chlorinated, or solvates or non-solvates) or compounds of formula (I) and / or their salts The mixture is in an amount representing from 10 ⁻³ to 10% by weight of the total weight of the composition, preferably from 10 ⁻³ to 5% by weight of the total weight of the composition, even better 10 ⁻² It can be used in an amount representing from% to 2% by weight, for example from 0.5% to 2% by weight.

  The composition of the present invention may be intended for cosmetic or pharmaceutical use. The composition of the present invention is preferably used for cosmetic purposes. In addition, the composition must contain non-toxic, physiologically acceptable media that can be applied to human skin such as the scalp and eyelids, and keratin fibers. For the purposes of the present invention, the term “cosmetic” means a composition with a pleasant appearance, odor and feel.

  Chlorinated or non-chlorinated and solvated or non-solvated compounds of formula (I) are compositions to be applied orally, injected or applied to the skin or keratin fibers (skin or fibers in any area to be treated) Can be used for

  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 mg to 300 mg per day, for example 5 mg to 10 mg / day.

  Preferred compositions of the present invention are compositions for cosmetic use, especially for topical application to skin and keratin fibers, more particularly to the scalp, hair and eyelashes.

  The composition can be in any known form that is suitable for the mode of use.

  For topical application to the skin or keratin fibers, the composition may be an aqueous, alcoholic or aqueous-alcoholic solution or suspension, or an oily suspension or solution, a fatty phase in an aqueous phase (O / W ) Or vice versa (W / O), solid (O / W) or (W / O) emulsions or dispersions, more or less liquid consistency, especially liquid or semi-liquid consistency Emulsions or dispersants, more or less liquid or solid aqueous, aqueous-alcoholic or oily gels, free or compacted powders used in unmodified form or incorporated in physiologically acceptable media, or micro It can be in the form of capsules, microparticles or ionic and / or non-ionic type vesicular dispersions.

  Compositions comprising foamed forms or sprays or aerosols and thus pressurized sprays can also be envisaged.

  The composition can also be in the form of lotion, serum, milk, O / W or W / O cream, gel, ointment, ointment, powder, balm, patch, impregnated pad, cake or foam. .

  In particular, the composition for application to the scalp or hair is for example a hair care lotion applied daily or twice a week, in particular a shampoo or hair conditioner applied twice or weekly, a liquid or solid scalp cleansing soap applied daily, a hairstyle It can be in the form of a shaped product (lacquer, hair set product or styling gel), treatment mask, foam gel or cream for hair cleansing. The composition may also be in the form of a hair dye or mascara applied by brush or comb.

  Further, for application to the eyelashes or body hair, the composition to which the present invention is applied may be in the form of a colored or non-colored mascara for application to the eyelashes or beard or mustache by brush.

  For compositions for injectable use, the compositions may be in the form of an aqueous lotion or oily suspension. For oral use, the composition may be in the form of capsules, granules, drinkable syrups or tablets.

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

  The amounts of the various constituents according to the present invention take into account those generally used in the field. 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%, preferably from 5% to 50% by weight relative to the total weight of the composition. The aqueous phase is adjusted as a function of the content of the fatty phase and compound (I), as well as the content of any additional ingredients to obtain 100% by weight. In fact, the aqueous phase represents 5% to 99.9% by weight.

  The fatty phase can contain fatty or oily compounds that are liquid at room temperature (25 ° C.) and atmospheric pressure (760 mmHg), commonly known as oils. These oils may be compatible or incompatible with each other and can form a macroscopically uniform liquid fatty phase system or two-phase or three-phase system.

  In addition to oils, the fatty phase can contain waxes, gums, lipophilic polymers or “pasty” or viscous products containing solid and liquid portions.

The aqueous phase is water and optionally, miscibility of the components in all proportions with water, for example, lower alcohols from C ₁ such as ethanol or isopropanol to C _8, polyols, such as propylene glycol, glycerol or sorbitol, Alternatively, it contains acetone or ether.

  The emulsifiers and coemulsifiers used to obtain the composition in the form of an emulsion are those commonly used in cosmetics and pharmaceuticals. Their properties also depend on the content of the emulsion. Indeed, the emulsifier and optionally the co-emulsifier are present in the composition in the range of 0.1% to 30% by weight, preferably 0.5% to 20% by weight and better still 1% to 8% by weight. Emulsions can also contain liquid vesicles, especially liposomes.

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

  For hair application, the compositions of the invention are advantageously aqueous, alcoholic or aqueous-alcoholic solutions or suspensions, and better still water / ethanol solutions or suspensions. This alcohol part can represent from 5% to 99.9%, better still from 8% to 80%.

  For topical maraca applications, the compositions of the invention are in particular in the form of wax-in-water or wax-in-oil dispersants, gelled oils or aqueous gels which may be colored or uncolored.

  The composition of the present invention comprises an aqueous or oil phase solvent, a thickener or gelling agent, a solid particle such as a dye, filler or pigment that can be dissolved in the composition medium, an antioxidant, a preservative, a fragrance, For cosmetics and pharmaceuticals having an advantageous effect on the skin or keratin fibers other than electrolytes, neutralizers, film-forming polymers, UV blockers such as sunscreens, compounds of formula (I) and mixtures thereof Other active ingredients selected from active agents and considered in the art and commonly used may also be included. These additives are generally used in cosmetics and dermatology, in particular from 0.01% to 50% by weight, better still from 0.1% to 20% by weight, for example from the total weight of the composition, for example It can be present in the composition in a proportion from 0.1% to 10% by weight. Depending on their nature, these additives can be introduced into the fatty phase, aqueous phase and / or lipid vesicles, in particular liposomes.

  It goes without saying that the person skilled in the art knows that the advantageous features of the composition according to the invention, i.e. the inhibition of type 1 15-PGDH, in particular the increase in the density of keratin fibers, has no adverse effect or is substantially Care will be taken to select the optional additional ingredients and / or amounts thereof so as not to overwhelm.

Solvents that can be used in the present invention include C ₂ to C ₈ lower alcohols such as ethanol, isopropanol, propylene glycol and certain cosmetic light oils such as C ₆ to C ₁₆ alkanes.

  Oils that can be used in the present invention include mineral source oils (liquid petroleum jelly or hydrogenated isoparaffin), plant source oils (fraction of shea butter, sunflower oil, apricot oil, fatty alcohol or fatty acid), animal sources Oils (perhydrosqualene), synthetic oils (fatty acid esters, pruselin oil), silicone oils (linear or cyclic polydimethylsiloxane, phenyltrimethicone) and fluoro oils (perfluoropolyethers) Can do. Waxes that can be mentioned include silicone waxes, beeswax, rice wax, candelilla wax, carnauba wax, paraffin wax and polyethylene wax.

  Examples of emulsifiers that can be used in the present invention include glyceryl stearate, glyceryl laurate, sorbitol stearate, sorbitol oleate, alkyl dimethicone copolyols (with 8 or more alkyls) for W / O emulsion ) And mixtures thereof. For O / W emulsions, polyethylene glycol monostearate or monolaurate, polyoxyethylenated sorbitol stearate or oleate, and dimethicone copolyols, and mixtures thereof can also be used.

  Hydrophilic gelling agents that can be used in the present invention include carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkyl acrylate copolymers, polyacrylamides, polysaccharides such as hydroxypropylcellulose, natural rubbers and clays. Lipophilic gelling agents that can be used include modified clays such as bentones, metal salts of fatty acids such as aluminum stearate, hydrophobically treated silica and ethylcellulose, and mixtures thereof. Can be mentioned.

  Cosmetic or pharmaceutical active agents other than the compound of formula (I) that can be used in the present invention include proteins or protein hydrolysates, amino acids, polyols, urea, allantoin, saccharides and sugar derivatives, water-soluble vitamins, Hydrophilic actives selected from plant extracts (from Iridaceae or soy) and hydroxy acids such as fruit acids or salicylic acid; and retinol (vitamin A) and its derivatives, in particular esters (retinyl palmitate), Phenol (vitamin E) and its derivatives, especially esters (tocopheryl acetate), essential fatty acids, ceramides, essential oils, salicylic acid derivatives such as 5-octanoylsalicylic acid, hydroxy acid esters, and phospholipids such as List fat-soluble active agents such as lecithin, and mixtures thereof It can be.

  According to one particular embodiment of the invention, the compound of formula (I) or a salt and / or solvate thereof promotes the regeneration of keratin fibers and / or reduces the loss of keratin fibers (hair or eyelashes). Can be combined with additional compounds to limit. These additional compounds are in particular the lipoxygenase inhibitors described in EP 648 488, in particular the bradykinin inhibitors described in EP 845 700, in particular WO 98/33497, WO 95/11003, JP 09-100 091. And prostaglandins and derivatives thereof described in JP-A-08-134242, EP 1 175 891, EP 1 175 890, WO 01/74307, WO 01/74313, WO 01/74314, Prostaglandin receptor agonists or antagonists described in WO 01/74315 or WO 01/72268, non-prostannic acid prostaglandin analogs, and mixtures thereof.

  Other additional active compounds that may be present in the composition according to the invention to promote the regeneration of keratin fibers and / or limit their loss (especially hair and eyelashes) include vasodilators, antiandrogens Mention may be made of substances, cyclosporines and their analogs, antibacterial and antifungal agents, anti-inflammatory agents, and retinoids, alone or in mixtures.

  Vasodilators that can be used are, in particular, potassium channel agonils containing minoxidil, U.S. Pat.No. 3,382,247, U.S. Pat.No. 5,756,092, U.S. Pat.No. 5,772,990, U.S. Pat. The compounds described in US Pat. No. 5,466,694, US Pat. No. 5,438,058 and US Pat. No. 4,973,474, cromakalim, nicorandil and dioxozide, alone or in combination.

  Anti-androgenic substances that can be used are in particular steroidal or non-steroidal 5α-reductase inhibitors, such as the compounds described in finasteride and US Pat.No. 5,516,779, cyprosterone acetate, azelaic acid and its salts And derivatives, as well as the compounds described in US Pat. No. 5,480,913, flutamide, oxendron, spironolactone, diethylstilbestrol and US Pat. No. 5,411,981, US Pat. No. 5,565,467 and US Pat. And compounds described in No. 226.

Antifungal or antifungal compounds include selenium derivatives, octopirox, triclocarban, triclosan, zinc pyrithione, itraconazole, asiatic acid, hinokitiol, mipyrosin, tetracyclines, especially erythromycin And compounds described in EP 0 680 745, clyncin hydrochloride, benzoyl peroxide or benzyl peroxide, minocycline and econazole, ketoconazole or miconazole or salts thereof, in particular tocopheryl nicotinate, It can be selected from nicotinic acid esters such as benzyl nicotinate and C ₁ -C ₆ alkyl nicotinates, for example methyl nicotinate or hexyl nicotinate.

  Anti-inflammatory agents include steroidal anti-inflammatory agents such as glucocorticoids, corticosteroids (e.g .: hydrocortisone) and non-steroidal anti-inflammatory agents such as glycyrrhetinic acid and α-bisabolol, benzydamine, salicylic acid and EP 0 770 399, WO 94/06434 and FR 2 268 523.

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

  Formulas that promote the regeneration of keratin fibers such as hair and eyelashes and / or limit the loss of keratin fibers and may or may not be salified and solvated ( Other additional active compounds that can be used in combination with compounds of I) include aminexyl, 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 pantothenate, panthenol, resorcinol, protein kinase C activator, glycosidase inhibitor, glycosaminoglycanase inhibition Agent, pyroglutamate, hexosaccharide or reed Hexosaccharides, substituted arylethylenes, N-acylamino acids, flavonoids, ascomycin derivatives and analogs, histamine antagonists, saponins, proteoglycanase inhibitors, estrogen agonists and antagonists, pseudoterins, cytokines, Growth factor promoters, IL-1 or IL-6 inhibitors, IL-10 promoters, TNF inhibitors, benzophenones, hydantoin, retinoic acid; vitamins such as vitamin D, vitamin B12 analogs and pantothenol; triterpenes Compounds such as ursolic acid and compounds described in U.S. Pat.No. 5,529,769, U.S. Pat.No. 5,468,888 and U.S. Pat. Diene; antiparasitic agent, especially metronida Sol, crotamiton or pyrethroids; calcium antagonists such as cinnarizine, ziltriazem, nimodipine, verapamil, alberine and nifedipine; hormones such as estriol or its analogs, thyroxine and its salts, and progesterone; latanoprost, (5E) -7-{(1R, 2R, 3R, 5S) -3,5-dihydroxy-2-[(3R) -3-hydroxy-5-phenylpentyl] cyclopentyl} hept-5-enoic acid, bimatoprost, travoprost, Mention may be made of FP receptor (F-type prostaglandin receptor) agonists such as unoprostone and butaprost; mixtures thereof.

  The composition according to the invention comprises at least one 15-PGDH inhibitor as defined above and at least one prostaglandin or prostaglandin derivative, for example in the salt or ester form (for example isopropyl esters) in particular. Series 2 prostaglandins including PGF2-α and PGE2, such as 16,16-dimethyl PGE2, 17-phenyl PGE2, 16,16-dimethyl PGF2-α, 17-phenyl PGF2-α, series 1 prostagland Gins such as 11-prostaglandin E1, 1-deoxyprostaglandin E1 in salt or ester form, its analogs, in particular latanoprost, (5E) -7-{(1R, 2R, 3R, 5S) -3 , 5-Dihydroxy-2-[(3R) -3-hydroxy-5-phenylpentyl] cyclopentyl} hept-5-enoic acid, biprostol, bimatoprost, cloprostenol, travoprost, fluprostenol Advantageously, chloroprostenol, butaprost, unoprostone, misoprostol, and salts or esters thereof.

  The composition preferably contains at least one non-prostanoic acid EP2 and / or EP4 receptor agonist, as described in particular in EP 1 175 892.

  The composition also comprises at least a chlorinated or non-chlorinated, solvated or non-solvated compound of formula (I) to form a liposome, particularly as described in document WO 94/22468 It can be assumed about things. Thus, compounds encapsulated in liposomes can be selectively delivered to the hair follicle.

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

  A composition containing an effective amount of a chlorinated or non-chlorinated, solvated or non-solvated compound of formula (I) is applied, for example, in the evening and maintained in contact throughout the night, optionally shampooed in the morning. To do. These applications can be repeated daily for one or more months depending on the individual.

  In the method according to the invention, between 5 μL and 500 μL of a solution or composition as defined above containing 0.001% to 5% 15-PGDH inhibitor is applied to the area of the scalp for care or treatment This is advantageous.

  Although typical embodiment of this invention is illustrated, this invention is not limited to these.

(Example)
Examples of 2-oxyacetamide compounds of the formula (II) according to the invention that can be mentioned include the following compounds:
Compound 1

Compound 2

Compound 3

Is mentioned.

Examples of 2-oxyacetamide compounds of the formula (III) according to the invention that can be described include the following compounds:
Compound 4

Compound 5

Compound 6

Compound 7

Compound 8

Compound 9

Compound 10

Compound 11

Compound 12

Compound 13

Is mentioned.

Examples of 2-oxyacetamide compounds of the formula (IV) according to the invention that can be described include the following compounds:
Compound 14

Compound 15

Compound 16

Is mentioned.

Examples of 2-oxyacetamide compounds of the formula (V) according to the invention that can be described include the following compounds:
Compound 17

Compound 18

Compound 19

Is mentioned.

According to another embodiment of the present invention, the 2-oxyacetamide compound has the following three formulas:
Compound 20

Compound 21

Compound 22

Satisfy one of them.

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

  Other compounds to which the present invention applies are known per se. They can be manufactured in a known manner.

The compounds of formula (I) to which the present invention applies can be synthesized according to the following reaction scheme, in any case, even if they are known to be novel:
step 1:

  Step 2:

  The operating conditions (solvent, base, temperature) for the synthesis of the compound of formula (I) depend on the starting reagents.

Other examples of 2-oxyacetamide compounds of formula (I) that can be used in the present invention can include the following compounds:
Compound 23

Compound 24

Compound 25

Compound 26

Compound 27

Compound 28

Compound 29

Compound 30

Compound 31

Compound 32

Compound 33

Compound 34

Compound 35

  The compounds to which the present invention applies are compounds 2, 3, 5, 6, 8, 9, 10, 12, 13, 18, 19, 21, 23, 24, 28, 32, 34 and 35, particularly novel compound 2 3, 5, 6, 8, 9, 10, 12, 13, 18, 19 and 21 and compounds 23 and 24. The compounds to which the present invention is applied are preferably novel compounds 2, 3, 12, 13 and 21, and compounds 23 and 24.

  Examples of the synthesis of the compounds according to the invention are given here as non-limiting illustrations that do not limit the scope of the invention in any way.

  Example 1: Reaction scheme for the synthesis of compound 21:

Method
0.63 ml of freshly distilled cyclohexanol (6 mmol) is introduced into a three-necked flask under a stream of argon and diluted with 10 ml of anhydrous dimethylformamide. 60% sodium hydride (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 before adding a solution of N-benzyl-2-chloroacetamide (1 g; 5.44 mmol) in 10 ml of anhydrous DMF. The medium is maintained at a temperature of 60 ° C. for 5 hours. The reaction mixture is concentrated to maximum and then diluted with 100 ml of dichloromethane. The organic phase is washed with water (2 x 50 ml) and then with saturated sodium chloride solution. The organic phase is dried over sodium sulfate, filtered and concentrated to the maximum. The crude product is dissolved in a minimum amount of ethyl ether and stirred for 30 minutes. The solid is removed and the filtrate is purified on silica gel (eluent: dichloromethane). After evaporating the solvent and drying under reduced pressure in the presence of phosphorus pentoxide, a beige solid (0.36 g, yield (yld) 24%) is obtained.

  Analysis of the product (nuclear magnetic resonance and mass spectrum) is consistent with equation 21.

  Example 2: Reaction scheme for the synthesis of compound 22:

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

  Analysis of the product (NMR and mass spectrum) is consistent with that expected for compound 22.

Example 3: Reaction scheme for the synthesis of compound 23:
Compound 23 is prepared in two steps.

  Step 1: Synthesis of chloroacetamide (a)

40 ml furfurylamine (c), 500 ml dichloromethane and 69.9 ml triethylamine (abbreviated Et ₃ N) are introduced into a three-necked flask. After cooling the reaction medium to 10 ° C., 37.1 ml of chloroacetyl chloride (b) diluted with 100 ml of dichloromethane are added dropwise, maintaining the temperature below 15 ° C. The reaction medium is then stirred for 3 hours at room temperature. Then add water. The organic phase is washed with water (twice with 100 ml), 1N dilute hydrochloric acid solution (twice with 50 ml), again with water and then with saturated sodium chloride solution. The organic phase is dried over sodium sulfate, filtered and concentrated to give 66 g of a brown solid (compound a, yield = 84%).

Product analysis (a)
Mass spectrometry (MS): quasimolecular ions (MH) ⁺ , (MNa) ^{+ of the} expected molecule C ₇ H ₈ ClNO ₂ are mainly detected.

Nuclear magnetic resonance (NMR): ¹ H (DMSO, 400 MHz) δ ppm: 8.66 (1H, broad 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 ).
Broad s = Broad singlet
d = doublet
dd = double doublet

  These results are consistent with the formula of compound (a).

  Step 2: Synthesis of compound 23 (2- (3-chlorophenoxy) -N-furan-2-ylmethylacetamide)

  1 g of 3-chlorophenol (d), 20 ml of tetrahydrofuran (THF) and 1.9 g of cesium carbonate are introduced into a three-necked flask. Then 1.34 g of the compound (a) solution prepared above is added in 20 ml of dichloromethane (DCM). The organic medium is refluxed for 5 hours before adding water. The organic phase is washed with water (2 × 100 ml), 1N diluted sodium hydroxide solution (2 × 50 ml), again with water (2 × 100 ml) and then with saturated sodium chloride solution. The organic phase is dried over sodium sulfate and concentrated to give 1.5 g of a light brown solid (compound 23, yield = 73%).

Product analysis (a)
NMR: ¹ H (DMSO, 400 MHz) δ ppm: 8.59 (1H, t, NH); 7.56 (1H, bs, H-Ar); 7.32 (1H, m, H-Ar); 7.04 (1H, d, H -Ar); 7.02 (1H, dd, H-Ar); 6.94 (1H, dd, H-Ar); 6.38 (1H, m, H-Ar); 6.21 (1H, m, H-Ar); 4.57 ( _{2H, s, CH 2);} 4.33 (2H, d, CH 2).
s = singlet broad s = broad singlet
d = doublet
dd = double doublet
t = triplet
m = multiplet
H-Ar = aromatic hydrogen

Mass spectrometry (MS): The quasimolecular ion (MH) ^{+ of the} expected molecule C ₁₃ H ₁₂ ClNO ₃ is mainly detected.

  These results are consistent with the formula of compound 23.

Examples 4, 5 and 6: Reaction scheme for the synthesis of compounds 24, 25 and 26:
These compounds are prepared according to the same method as compound 21, replacing cyclohexane with phenol for compound 24, 3-chlorophenol for compound 25 and 4-chlorophenol for compound 26, respectively.

  The mass spectrum (+ and −ESU) is consistent with the expected structure.

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

Method
A suspension of 28 mg potassium carbonate in 1 ml acetone is introduced into a reaction tube equipped with a magnetic bar. Then 6.4 mg 8-hydroxyquinoline (CAS: 148-24-3; Fluka reference: F55080) solution in 0.5 ml acetone and 7.9 mg 2-chloro-2 ', 6'- in 0.5 ml acetone Add acetoxylidide (CAS: 1131-01-7) solution. This medium is diluted with 1 ml of acetone, stoppered and refluxed for 24 hours. The reaction medium is cooled to room temperature, filtered through a sintering funnel and the solid is rinsed with 2.5 ml of acetone. The filtrate was concentrated under reduced pressure, dissolved in 300 μl of a 9/1 dichloromethane / methanol mixture, and 80 mg PL-TBD resin (1,3,4,6,7, filled at 2.7 mmol / g in 1.5 ml dichloromethane). 8-Hexahydro-2H-pyrimido [1,2-a] pyrimidine resin) is added to the suspension. The medium is left for 24 hours, then filtered through a sintering funnel and concentrated. Compound 1 (N- (2,6-dimethylphenyl) -2- (quinolin-8-yloxy) acetamide) is obtained in the form of a brown solid (9.2 mg, 75% yield).

Analysis Mass spectrometry: (+ and −ESI): (M + H) ⁺ = 307 and (M + Na) ⁺ = 330.

  Compounds 2 and 3 were obtained in a similar manner by reacting 8-hydroxyquinoline (CAS: 148-24-3; see Fluka: F55080) with the following commercially available chloroacetamides according to the same method:

  For N- (2-chlorophenyl) -2-chloroacetamide (3289-76-7), compound 2 (N- (2-chlorophenyl) -2-quinolin-8-yloxy) acetamide) was converted to a brown solid (7.4 mg, Yield 59%).

  For N- (2-chloroacetyl) -2- (trifluoromethyl) aniline (3792-04-9), compound 3 (2- (quinolin-8-yloxy) -N- (2-trifluoromethylphenyl) Acetamide) was obtained in the form of an orange solid (6.5 mg, 47% yield).

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

  This method is the same as described in the compound synthesis of general formula (II).

  Thus, compound 4 contains 1- (4-hydroxyphenyl) ethanone (4-hydroxyacetophenone CAS: 99-93-4) and ethyl 4- (2-chloroacetamido) benzoate (4- (2-chloroacetylamino) Obtained in the form of white crystals (11.2 mg, 82% yield) by reaction with 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:

Method
9.6 mg benzyloxyacetyl chloride (CAS: 19810-31-2; Aldrich source: 30,101-9) 0.5 ml dichloromethane and 5.2 mg (S)-(+)-tetrahydrofurfurylamine (CAS: 7175-81- 7) 0.5 ml 1N sodium hydroxide solution is introduced into a reaction tube equipped with a magnetic bar. The medium is diluted with 0.5 ml of dichloromethane and then 1 ml of 1N sodium hydroxide solution is added to it. The reaction medium is maintained under magnetic stirring for 24 hours and then poured onto a liquid-liquid extraction cartridge (Chem Elut Varian) to evaporate the organic phase. Compound 14 (2-benzyloxy-N- (tetrahydrofuran-2-ylmethyl) acetamide) is obtained in a yield of 72% (7.2 mg).

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

  Compounds 15 and 16 are obtained according to the same method. The data is collated with the table below:

Examples 23 to 25: Reaction scheme for the synthesis of compounds 17, 18 and 19 of general formula (V):
This method is the same as described in the synthesis of compounds of general formula (IV).

  Compounds 17, 18 and 19 are obtained according to the data collated in the table below:

  Example 26: Reaction Scheme for Synthesis of Compound 20:

  This method is the same as that used for the synthesis of 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 specific inhibitory properties against 15-PGDH of compounds of formula (I)
1) Test for Type 1 15-PGDH:
The enzyme 15-PGDH was obtained as described in patent application FR 02/05067 filed under the name L'Oreal, and as a suspension in a medium adapted to a concentration of 0.3 mg / ml, Freeze at 80 ° C. For testing purposes, this suspension is thawed and stored in ice.

Separately, 0.1 mM dithiothreitol (D5545, Sigma-Aldrich, L'isle D'Abeau Chesne, BP701, 38297, Saint Quentin Fallavier), 1.5 mM β-NAD (N6522, Sigma-Aldrich, L'isle D ' Abeau Chesne, BP701, 38297, Saint Quentin Fallavier), 50 mM prostaglandin E ₂ (P4172, Sigma-Aldrich, L'isle D'Abeau Chesne, BP701, 38297, Saint Quentin Fallavier) Prepare buffer.

  0.965 ml of this buffer (previously adjusted to 37 ° C.) is introduced into a spectrophotometer cuvette (Perkin-Elmer, Lambda 2) maintained at 37 ° C. under thermostat control, and its measurement wavelength is set to 340 nm. 0.035 ml of the enzyme suspension is introduced into a cuvette for simultaneous recording (corresponding to an increase in optical density at 340 nm) at 37 ° C. Record the maximum reaction rate.

Test values (containing compound of formula (I)) are compared to control values (no compound of formula (I)). This displayed result represents the percentage of inhibition of enzyme activity of 15-PGDH for a given concentration of compound of formula (I), or the compound of formula (I) reduced the enzyme activity of 15-PGDH by 50% It is expressed in either decreasing concentration, ie IC _50dh .

2) Testing for PGF synthase The enzyme PGFS was obtained as described in the literature patent application FR-A-02 / 05067 and frozen at −80 ° C. at a concentration of 0.5 mg / mL as a suspension in a suitable medium. Let For testing purposes, the suspension is thawed and stored in ice.

  In parallel, 20 μM 9,10-phenanthrenequinone * (P2896, Sigma-Aldrich, L'isle D'Abeau Chesne, BP701, 38297, Saint Quentin Fallavier) and 100 μM β-NADPH (N1630, Sigma-Aldrich, L A 100 mM pH 6.5 Tris buffer containing 'isle D'Abeau Chesne, BP701, 38297, Saint Quentin Fallavier) is prepared in a brown flask (protected from light).

  * A stock solution having a titer of 1 mM is prepared in absolute ethanol and adjusted to 40 ° C .; the flask is placed in an ultrasonic cuvette to facilitate dissolution of the product.

  0.950 mL of this buffer (previously adjusted to 37 ° C.) is introduced into a spectrophotometer cuvette (Perkin-Elmer, Lambda 2) maintained at 37 ° C. under thermostat control, and its measurement wavelength is set to 340 nm. 0.05 mL of the enzyme suspension is introduced into a cuvette for simultaneous recording (corresponding to a decrease in optical density at 340 nm) at 37 ° C. Record the maximum reaction rate.

Test values (containing compound of formula (I)) are compared to control values (no compound of formula (I)). This displayed result represents the percentage of inhibition of enzyme activity of PGFS for a given concentration of compound of formula (I) or the concentration at which compound of formula (I) reduces the enzyme activity of PGFS by 50%, That is, it is expressed by one of IC _50fs .

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

  From these tables it is clear that the compound of formula (I) is an inhibitor of type-1 15-PGDH and inhibits it very selectively when compared to inhibition of PGFS.

  The following compositions are obtained according to conventional techniques normally used in the cosmetic or pharmacological field.

Example 28: Hair Lotion-Compound 23 1.00 g
-30.00 g of propylene glycol
-40.00 g of ethyl alcohol
-Water total 100.00g

  This lotion is applied once or twice a day by gently massaging the scalp so that the active agent penetrates the scalp at a rate of 1 ml per application. The hair is then air dried. This lotion can delay hair loss and promote hair regeneration. It is also possible to improve hair growth.

Example 29: Hair lotion-Compound 21 1.00 g
-30.00 g of propylene glycol
-40.00 g of ethyl alcohol
-Water total 100.00g

  This lotion is applied once or twice a day by gently massaging the scalp so that the active agent penetrates the scalp at a rate of 1 ml per application. The hair is then air dried. This lotion can delay hair loss and promote hair regeneration. It is also possible to improve hair growth.

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 appropriate amount-Water Total 100.00%

  This mascara is applied to the eyelashes like a normal mascara using a mascara brush.

Example 31: Hair Lotion-Compound 21 0.10 g
-Latanoprost 0.10g
-30.00 g of propylene glycol
-40.00 g of ethyl alcohol
-Water total 100.00g

  This lotion is applied once or twice a day by gently massaging the scalp so that the active agent penetrates the scalp at a rate of 1 ml per application. The hair is then air dried. This lotion can delay hair loss and promote hair regeneration. It is also possible to improve hair growth.

Example 32: Hair Lotion- (5E) -7-{(1R, 2R, 3R, 5S) -3,5-Dihydroxy-2-[(3R) -3-hydroxy-5-phenylpentyl] -cyclopentyl} hept -5-enoic acid 0.10g
-Compound 0.10 g
-30.00 g of propylene glycol
-40.00 g of ethyl alcohol
-Water total 100.00g

  This lotion is applied once or twice a day by gently massaging the scalp so that the active agent penetrates the scalp at a rate of 1 ml per application. The hair is then air dried. This lotion can delay hair loss and promote hair regeneration. It is also possible to improve hair growth.

Claims (54)

Effective amount formula (I):

Where:
a) R ₁ and R ₂ are
1) Hydrogen, where R ₁ is different from R ₂
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) 3 to 7 hydrocarbon-based ring C ¹ optionally fused to at least one ring C ² of 4 to 7 atoms, wherein ring C ² is a heterocycle Hy ₂ Optionally containing at least one heteroatom to form a ring C ¹ and a ring C ² optionally containing a carbonyl function or a thiocarbonyl function and / or at least one substituent A ₂ Is replaced by,
4) A heterocyclic Hy ₁ fused to any of four of up to 7 atoms in the ring C ^2, the ring C ² is optionally at least one heteroatom to form a heterocyclic Hy ₂ These rings Hy ₁ and C ² , possibly containing a carbonyl function or a thiocarbonyl function, and / or substituted by at least one substituent A ₁ ,
5) group C (= NR) R ', C (= NR) NR'R'', COR, CSR, COOR, CONRR', SO 2 R or SO ₂ NRR '
One of, independently selected;
b) R ₃ is
1) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
2) 3 to 7 optionally fused to at least one ring C ⁴ of 4 to 7 atoms optionally containing at least 1 heteroatom to form a heterocycle Hy ₄ A hydrocarbon-based ring C ³ of these atoms, wherein ring C ³ and ring C ⁴ optionally comprise a carbonyl function or a thiocarbonyl function and / or are substituted by at least one substituent A ₂ ing,
3) A heterocyclic Hy ₃ selected from a pyrrole ring, a furan ring, a thiophene ring and a pyrazole ring, optionally fused to a ring C ⁵ representing phenyl, pyridine or pyrimidine, wherein the heterocyclic Hy ₃ and the ring C ⁵ are Optionally substituted with at least one substituent A ₁ ,
4) Unlike Hy ₃ , a heterocycle Hy ₅ optionally fused to a ring C ⁶ of 4 to 7 atoms, wherein the ring Hy ₅ and ring C ⁶ are carbonyl functional groups or thio This ring C ⁶ optionally contains at least one heteroatom to form a heterocycle Hy ₆ possibly containing a carbonyl function and / or substituted by at least one substituent A ₁ Selected from;
c) R, R 'and R''are:
1) hydrogen,
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) 4 to ₇ optionally containing at least one heteroatom to form heterocycle Hy ₇ and / or optionally containing at least one heteroatom to form heterocycle Hy ₈ a ring C ⁷ atoms from four fused to an optionally ring C ⁸ atoms up pieces up to 7, optionally substituted by rings C ⁷ and ring C ⁸ is at least one substituent a ₁ Independently selected from, optionally including a carbonyl function or a thiocarbonyl function;
d) A ₁ is:
1) halogen,
2) C ₁ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
3) optionally contain at least one hetero atom to form a heterocyclic ring Hy _9, and / or 15 in atom ring C ¹⁰ of from four to seven from four fused to optionally Ring C ⁹ of atoms up to, wherein these ring C ⁹ and ring C ¹⁰ are selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C _{1 to} C ₂₀ alkyl groups Optionally containing at least one substituent A ₃
4) R ₄ , R ′ ₄ , R ″ ₄ and R ′ ″ ₄ are independently C ₁ -C ₂₀ alkyl optionally substituted with hydrogen or heterocyclic Hy ₁₀ or CONR ₅ R ′ ₅ group 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 , selected from Si (OR ₄ ) (OR' ₄ ) OR '' ₄ , and one of SO ₃ H;
e) A ₂ is:
1) halogen,
2) R ₄ , R ′ ₄ and R ″ ₄ independently represent a group CF ₃ , CN, OR ₄ , SR ₄ which represents a C ₁ -C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group. , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR ₄ R' ₄ R '' ₄ , one of NO ₂ and OCF ₃ ,
3) C ₁ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
4) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, wherein these ring C ¹¹ and ring C ¹² are selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C ₁ -C ₂₀ alkyl groups that at least one substituent a ₃ possibly is selected from;
f) R ₅ and R ' ₅ are
1) hydrogen,
2) C ₁ ~C ₂₀ alkyl group, independently selected from;
g) Hy ₁ , Hy ₂ , Hy ₄ to Hy ₈ , Hy ₁₀ and Hy ₁₁ are potentially 1 to 4 heteroatoms independently selected from N, O and S and combinations thereof. Represents a heterocycle of 4 to 7 atoms containing and / or containing a carbonyl function or a thiocarbonyl function;
h) Hy ₉ optionally contains 1 to 5 heteroatoms selected from N, O and S and combinations thereof and / or 4 containing carbonyl or thiocarbonyl functions For inducing and / or stimulating the growth of keratin fibers, in particular human keratin fibers, of at least one 2-oxyacetamide compound of 1 to 15 atoms, which represents a heterocycle of from 1 to 15, or a salt and / or solvate thereof, And / or their use as agents for delaying their loss and / or increasing their density. Formula (I):

Where:
a) R ₁ and R ₂ are
1) Hydrogen, where R ₁ is different from R ₂
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) 3 to 7 hydrocarbon-based ring C ¹ optionally fused to at least one ring C ² of 4 to 7 atoms, wherein ring C ² is a heterocycle Hy ₂ Optionally containing at least one heteroatom to form a ring C ¹ and a ring C ² optionally containing a carbonyl function or a thiocarbonyl function and / or at least one substituent A ₂ Is replaced by,
4) A heterocyclic Hy ₁ fused to any of four of up to 7 atoms in the ring C ^2, the ring C ² is optionally at least one heteroatom to form a heterocyclic Hy ₂ In which these rings Hy ₁ and C ² optionally contain a carbonyl function or a thiocarbonyl function and / or are substituted by at least one substituent A ₁ ,
5) group C (= NR) R ', C (= NR) NR'R'', COR, CSR, COOR, CONRR', SO 2 R or SO ₂ NRR '
One of, independently selected;
b) R ₃ is
1) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
2) 3 to 7 optionally fused to at least one ring C ⁴ of 4 to 7 atoms optionally containing at least 1 heteroatom to form a heterocycle Hy ₄ A hydrocarbon-based ring C ³ of these atoms, wherein ring C ³ and ring C ⁴ optionally comprise a carbonyl function or a thiocarbonyl function and / or are substituted by at least one substituent A ₂ ing,
3) A heterocyclic Hy ₃ selected from a pyrrole ring, a furan ring, a thiophene ring and a pyrazole ring, optionally fused to a ring C ⁵ representing phenyl, pyridine or pyrimidine, wherein the heterocyclic Hy ₃ and the ring C ⁵ are Optionally substituted with at least one substituent A ₁ ,
4) Unlike Hy ₃ , a heterocycle Hy ₅ optionally fused to a ring C ⁶ of 4 to 7 atoms, wherein the ring Hy ₅ and ring C ⁶ are carbonyl functional groups or thio This ring C ⁶ optionally contains at least one heteroatom in order to form a heterocycle Hy ₆ optionally containing a carbonyl function and / or substituted by at least one substituent A ₁ Selected from;
c) R, R 'and R''are:
1) hydrogen,
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) 4 to ₇ optionally containing at least one heteroatom to form heterocycle Hy ₇ and / or optionally containing at least one heteroatom to form heterocycle Hy ₈ a ring C ⁷ atoms from four fused to an optionally ring C ⁸ atoms up pieces up to 7, optionally substituted by rings C ⁷ and ring C ⁸ is at least one substituent a ₁ Is selected independently from;
d) A ₁ is:
1) halogen,
2) C ₁ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
3) optionally contain at least one hetero atom to form a heterocyclic ring Hy _9, and / or 15 in atom ring C ¹⁰ of from four to seven from four fused to optionally Ring C ⁹ of atoms up to, wherein these ring C ⁹ and ring C ¹⁰ are selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C _{1 to} C ₂₀ alkyl groups Optionally containing at least one substituent A ₃
4) R ₄ , R ′ ₄ , R ″ ₄ and R ′ ″ ₄ are independently C ₁ -C ₂₀ alkyl optionally substituted with hydrogen or heterocyclic Hy ₁₀ or CONR ₅ R ′ ₅ group 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 , selected from Si (OR ₄ ) (OR' ₄ ) OR '' ₄ , and one of SO ₃ H;
e) A ₂ is:
1) halogen,
2) R ₄ , R ′ ₄ and R ″ ₄ independently represent a group CF ₃ , CN, OR ₄ , SR ₄ which represents a C ₁ -C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group. , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR ₄ R' ₄ R '' ₄ , one of NO ₂ and OCF ₃ ,
3) C ₁ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
4) 4 to 15 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, wherein these ring C ¹¹ and ring C ¹² are selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C ₁ -C ₂₀ alkyl groups that at least one substituent a ₃ possibly is selected from;
f) R ₅ and R ' ₅ are
1) hydrogen,
2) C ₁ ~C ₂₀ alkyl group, independently selected from;
g) Hy ₁ , Hy ₂ , Hy ₄ to Hy ₈ , Hy ₁₀ and Hy ₁₁ are potentially 1 to 4 heteroatoms independently selected from N, O and S and combinations thereof. Represents a heterocycle of 4 to 7 atoms containing and / or containing a carbonyl function or a thiocarbonyl function;
h) Hy ₉ optionally contains 1 to 5 heteroatoms selected from N, O and S and combinations thereof and / or 4 containing carbonyl or thiocarbonyl functions For the care and / or treatment of keratin fibres, in particular human keratin fibres, of at least one 2-oxyacetamide compound, or a salt and / or solvate thereof, representing a heterocycle of from 1 to 15 atoms, Cosmetic use in cosmetic compositions to delay their loss and / or increase their density. Formula (I):

Where:
a) R ₁ and R ₂ are
1) Hydrogen, where R ₁ is different from R ₂
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) 3 to 7 hydrocarbon-based ring C ¹ optionally fused to at least one ring C ² of 4 to 7 atoms, wherein ring C ² is a heterocycle Hy ₂ Optionally containing at least one heteroatom to form a ring C ¹ and a ring C ² optionally containing a carbonyl function or a thiocarbonyl function and / or at least one substituent A ₂ Is replaced by,
4) A heterocyclic Hy ₁ fused to any of four of up to 7 atoms in the ring C ^2, the ring C ² is optionally at least one heteroatom to form a heterocyclic Hy ₂ In which these rings Hy ₁ and C ² optionally contain a carbonyl function or a thiocarbonyl function and / or are substituted by at least one substituent A ₁ ,
5) group C (= NR) R ', C (= NR) NR'R'', COR, CSR, COOR, CONRR', SO 2 R or SO ₂ NRR '
One of, independently selected;
b) R ₃ is
1) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
2) 3 to 7 optionally fused to at least one ring C ⁴ of 4 to 7 atoms optionally containing at least 1 heteroatom to form a heterocycle Hy ₄ A hydrocarbon-based ring C ³ of these atoms, wherein ring C ³ and ring C ⁴ optionally comprise a carbonyl function or a thiocarbonyl function and / or are substituted by at least one substituent A ₂ ing,
3) A heterocyclic Hy ₃ selected from a pyrrole ring, a furan ring, a thiophene ring and a pyrazole ring, optionally fused to a ring C ⁵ representing phenyl, pyridine or pyrimidine, wherein the heterocyclic Hy ₃ and the ring C ⁵ are Optionally substituted with at least one substituent A ₁ ,
4) Unlike Hy ₃ , a heterocycle Hy ₅ optionally fused to a ring C ⁶ of 4 to 7 atoms, wherein the ring Hy ₅ and ring C ⁶ are carbonyl functional groups or thio This ring C ⁶ optionally contains at least one heteroatom in order to form a heterocycle Hy ₆ optionally containing a carbonyl function and / or substituted by at least one substituent A ₁ Selected from;
c) R, R 'and R''are:
1) hydrogen,
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) 4 to ₇ optionally containing at least one heteroatom to form heterocycle Hy ₇ and / or optionally containing at least one heteroatom to form heterocycle Hy ₈ a ring C ⁷ atoms from four fused to an optionally ring C ⁸ atoms up pieces up to 7, optionally substituted by rings C ⁷ and ring C ⁸ is at least one substituent a ₁ Independently selected from, optionally including a carbonyl function or a thiocarbonyl function;
d) A ₁ is:
1) halogen,
2) C ₁ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
3) optionally contain at least one hetero atom to form a heterocyclic ring Hy _9, and / or 15 in atom ring C ¹⁰ of from four to seven from four fused to optionally Ring C ⁹ of atoms up to, wherein these ring C ⁹ and ring C ¹⁰ are selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C _{1 to} C ₂₀ alkyl groups Optionally containing at least one substituent A ₃
4) R ₄ , R ′ ₄ , R ″ ₄ and R ′ ″ ₄ are independently C ₁ -C ₂₀ alkyl optionally substituted with hydrogen or heterocyclic Hy ₁₀ or CONR ₅ R ′ ₅ group 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 , selected from Si (OR ₄ ) (OR' ₄ ) OR '' ₄ , and one of SO ₃ H;
e) A ₂ is:
1) halogen,
2) R ₄ , R ′ ₄ and R ″ ₄ independently represent a group CF ₃ , CN, OR ₄ , SR ₄ which represents a C ₁ -C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group. , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR ₄ R' ₄ R '' ₄ , one of NO ₂ and OCF ₃ ,
3) C ₁ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
4) 4 to 15 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, wherein these ring C ¹¹ and ring C ¹² are selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C ₁ -C ₂₀ alkyl groups that at least one substituent a ₃ possibly is selected from;
f) R ₅ and R ' ₅ are
1) hydrogen,
2) C ₁ ~C ₂₀ alkyl group, independently selected from;
g) Hy ₁ , Hy ₂ , Hy ₄ to Hy ₈ , Hy ₁₀ and Hy ₁₁ are potentially 1 to 4 heteroatoms independently selected from N, O and S and combinations thereof. Represents a heterocycle of 4 to 7 atoms containing and / or containing a carbonyl function or a thiocarbonyl function;
h) Hy ₉ optionally contains 1 to 5 heteroatoms selected from N, O and S and combinations thereof and / or 4 containing carbonyl or thiocarbonyl functions Represents a heterocycle of from 1 to 15 atoms,
Induces and / or stimulates the growth of said keratin fibers, in particular human keratin fibers, for the care and / or treatment of at least one 2-oxyacetamide compound, or salts and / or solvates thereof And / or use to produce a composition for delaying its loss and / or increasing their density. Formula (I):

Where:
a) R ₁ and R ₂ are
1) Hydrogen, where R ₁ is different from R ₂
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) 3 to 7 hydrocarbon-based ring C ¹ optionally fused to at least one ring C ² of 4 to 7 atoms, wherein ring C ² is a heterocycle Hy ₂ Optionally containing at least one heteroatom to form a ring C ¹ and a ring C ² optionally containing a carbonyl function or a thiocarbonyl function and / or at least one substituent A ₂ Is replaced by,
4) fused to any of four of up to 7 atoms in the ring C ² and has heterocycle Hy _1, in the ring C ² optionally containing at least one hetero atom to form a heterocyclic ring Hy ₂ A ring Hy ₁ and a ring C ² , which possibly contain a carbonyl function or a thiocarbonyl function and / or is substituted by at least one substituent A ₁ ,
5) group C (= NR) R ', C (= NR) NR'R'', COR, CSR, COOR, CONRR', SO 2 R or SO ₂ NRR '
One of, independently selected;
b) R ₃ is
1) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
2) 3 to 7 optionally fused to at least one ring C ⁴ of 4 to 7 atoms optionally containing at least 1 heteroatom to form a heterocycle Hy ₄ A hydrocarbon-based ring C ³ of these atoms, wherein ring C ³ and ring C ⁴ optionally comprise a carbonyl function or a thiocarbonyl function and / or are substituted by at least one substituent A ₂ ing,
3) A heterocyclic Hy ₃ selected from a pyrrole ring, a furan ring, a thiophene ring and a pyrazole ring, optionally fused to a ring C ⁵ representing phenyl, pyridine or pyrimidine, wherein the heterocyclic Hy ₃ and the ring C ⁵ are Optionally substituted with at least one substituent A ₁ ,
4) Unlike Hy ₃ , a heterocycle Hy ₅ optionally fused to a ring C ⁶ of 4 to 7 atoms, which ring Hy ₅ and ring C ⁶ is a heterocycle Hy ₆ In order to form this ring C ⁶ optionally contains at least one heteroatom, possibly contains a carbonyl function or a thiocarbonyl function and / or is substituted by at least one substituent A ₁ Is selected from;
c) R, R ', R''andR''' are:
1) hydrogen,
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) 4 to ₇ optionally containing at least one heteroatom to form heterocycle Hy ₇ and / or optionally containing at least one heteroatom to form heterocycle Hy ₈ a ring C ⁷ atoms from four fused to an optionally ring C ⁸ atoms up pieces up to 7, optionally substituted by rings C ⁷ and ring C ⁸ is at least one substituent a ₁ Independently selected from, optionally including a carbonyl function or a thiocarbonyl function;
d) A ₁ is:
1) halogen,
2) C ₁ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
3) optionally contain at least one hetero atom to form a heterocyclic ring Hy _9, and / or 15 in atom ring C ¹⁰ of from four to seven from four fused to optionally Ring C ⁹ of atoms up to, wherein these ring C ⁹ and ring C ¹⁰ are selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C _{1 to} C ₂₀ alkyl groups Optionally containing at least one substituent A ₃
4) R ₄ , R ′ ₄ , R ″ ₄ and R ′ ″ ₄ are independently C ₁ -C ₂₀ alkyl optionally substituted with hydrogen or heterocyclic Hy ₁₀ or CONR ₅ R ′ ₅ group 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 , selected from Si (OR ₄ ) (OR' ₄ ) OR '' ₄ , and one of SO ₃ H;
e) A ₂ is:
1) halogen,
2) R ₄ , R ′ ₄ and R ″ ₄ independently represent a group CF ₃ , CN, OR ₄ , SR ₄ which represents a C ₁ -C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group. , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR ₄ R' ₄ R '' ₄ , one of NO ₂ and OCF ₃ ,
3) C ₁ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
4) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, wherein these ring C ¹¹ and ring C ¹² are selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C ₁ -C ₂₀ alkyl groups that at least one substituent a ₃ possibly is selected from;
f) R ₅ and R ' ₅ are
1) hydrogen,
2) C ₁ ~C ₂₀ alkyl group, independently selected from;
g) Hy ₁ , Hy ₂ , Hy ₄ to Hy ₈ , Hy ₁₀ and Hy ₁₁ are independently selected from N, O and S and combinations thereof, and / or have a carbonyl or thiocarbonyl function. Represents a heterocycle of 4 to 7 atoms potentially containing 1 to 4 heteroatoms inclusive;
h) Hy ₉ optionally contains 1 to 5 heteroatoms selected from N, O and S and combinations thereof and / or 4 containing carbonyl or thiocarbonyl functions Represents a heterocycle of from 1 to 15 atoms,
Of at least one 2-oxyacetamide compound, or a salt and / or solvate thereof, as an inhibitor of type 1 15-hydroxyprostaglandin dehydrogenase, especially its human skin form. Formula (I):

Where:
a) R ₁ and R ₂ are
1) Hydrogen, where R ₁ is different from R ₂
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) 3 to 7 hydrocarbon-based ring C ¹ optionally fused to at least one ring C ² of 4 to 7 atoms, wherein ring C ² is a heterocycle Hy ₂ These ring C ¹ and ring C ² optionally contain at least one heteroatom to form a carbonyl function or a thiocarbonyl function and / or at least one substituent A ₂ Is replaced by,
4) A heterocyclic Hy ₁ fused to any of four of up to 7 atoms in the ring C ^2, the ring C ² is optionally at least one heteroatom to form a heterocyclic Hy ₂ In which these rings Hy ₁ and C ² optionally contain a carbonyl function or a thiocarbonyl function and / or are substituted by at least one substituent A ₁ ,
5) group C (= NR) R ', C (= NR) NR'R'', COR, CSR, COOR, CONRR', SO 2 R or SO ₂ NRR '
One of, independently selected;
b) R ₃ is
1) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
2) 3 to 7 optionally fused to at least one ring C ⁴ of 4 to 7 atoms optionally containing at least 1 heteroatom to form a heterocycle Hy ₄ A hydrocarbon-based ring C ³ of these atoms, wherein ring C ³ and ring C ⁴ optionally comprise a carbonyl function or a thiocarbonyl function and / or are substituted by at least one substituent A ₂ ing,
3) A heterocyclic Hy ₃ selected from a pyrrole ring, a furan ring, a thiophene ring and a pyrazole ring, optionally fused to a ring C ⁵ representing phenyl, pyridine or pyrimidine, wherein the heterocyclic Hy ₃ and the ring C ⁵ are Optionally substituted with at least one substituent A ₁ ,
4) Unlike Hy ₃ , a heterocycle Hy ₅ optionally fused to a ring C ⁶ of 4 to 7 atoms, wherein the ring Hy ₅ and ring C ⁶ are carbonyl functional groups or thio This ring C ⁶ optionally contains at least one heteroatom in order to form a heterocycle Hy ₆ optionally containing a carbonyl function and / or substituted by at least one substituent A ₁ Selected from;
c) R, R 'and R''are:
1) hydrogen,
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) 4 to ₇ optionally containing at least one heteroatom to form heterocycle Hy ₇ and / or optionally containing at least one heteroatom to form heterocycle Hy ₈ a ring C ⁷ atoms from four fused to an optionally ring C ⁸ atoms up pieces up to 7, optionally substituted by rings C ⁷ and ring C ⁸ is at least one substituent a ₁ Independently selected from, optionally including a carbonyl function or a thiocarbonyl function;
d) A ₁ is:
1) halogen,
2) C ₁ ~C ₂₀ alkyl group,
3) optionally contain at least one hetero atom to form a heterocyclic ring Hy _9, and / or 15 in atom ring C ¹⁰ of from four to seven from four fused to optionally Ring C ⁹ of atoms up to, wherein these ring C ⁹ and ring C ¹⁰ are selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C _{1 to} C ₂₀ alkyl groups Optionally containing at least one substituent A ₃
4) R ₄ , R ′ ₄ , R ″ ₄ and R ′ ″ ₄ are independently C ₁ -C ₂₀ alkyl optionally substituted with hydrogen or heterocyclic Hy ₁₀ or CONR ₅ R ′ ₅ group 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 , selected from Si (OR ₄ ) (OR' ₄ ) OR '' ₄ , and one of SO ₃ H;
e) A ₂ is:
1) halogen,
2) R ₄ , R ′ ₄ and R ″ ₄ independently represent a group CF ₃ , CN, OR ₄ , SR ₄ which represents a C ₁ -C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group. , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR ₄ R' ₄ R '' ₄ , one of NO ₂ and OCF ₃ ,
3) C ₁ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
4) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, wherein these ring C ¹¹ and ring C ¹² are selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C ₁ -C ₂₀ alkyl groups that at least one substituent a ₃ possibly is selected from;
f) R ₅ and R ' ₅ are
1) hydrogen,
2) C ₁ ~C ₂₀ alkyl group, independently selected from;
g) Hy ₁ , Hy ₂ , Hy ₄ to Hy ₈ , Hy ₁₀ and Hy ₁₁ are potentially 1 to 4 heteroatoms independently selected from N, O and S and combinations thereof. Represents a heterocycle of 4 to 7 atoms containing and / or containing a carbonyl function or a thiocarbonyl function;
h) Hy ₉ optionally contains 1 to 5 heteroatoms selected from N, O and S and combinations thereof and / or 4 containing carbonyl or thiocarbonyl functions Represents a heterocycle of from 1 to 15 atoms,
1 type 15-hydroxyprostaglandin dehydrogenase of at least one 2-oxyacetamide compound, or salts and / or solvates thereof, in particular for the treatment of disorders related to the form of the human skin, or keratin fibers Use especially for the production of a composition for the care and / or treatment of human keratin fibres.   6. Use according to any one of claims 1 to 5, characterized in that the human keratin fibers are head hair, eyebrows, eyelashes, beard, mustache and pubic hair.   At least one of the formula (I) as defined in claim 1 in a hair care composition for human cosmetics for the treatment of delayed hair loss and / or increased density and / or andrho-chrono-genetic alopecia Cosmetic use of 2-oxyacetamide compounds, or salts and / or solvates thereof.   To prepare human cosmetic hair care compositions for inducing and / or stimulating hair growth, delaying loss and / or increasing density, and / or treating spontaneous alopecia and / or androgenic alopecia Use of at least one 2-oxyacetamide compound of formula (I) as defined in claim 1 or a salt and / or solvate thereof.   At least one of the formula (I) as defined in claim 1 in a cosmetic composition for the purpose of caring for and / or making up human eyelashes, to increase their growth induction and / or irritation and / or density. Cosmetic use of certain 2-oxyacetamide compounds, or salts and / or solvates thereof.   At least of formula (I) as defined in claim 1 for preparing compositions for inducing their growth and / or stimulating and / or increasing their density for the care and / or treatment of human eyelashes Use of one 2-oxyacetamide compound, or a salt and / or solvate thereof. R ₁ represents hydrogen and R ₂ represents the following group:
- one or two optionally substituted by substituents A ₁ saturated C ₁ -C ₁₀ alkyl group,
-Saturated hydrocarbon-based rings of 3 to 6 carbon atoms,
- wherein O, containing from one to two heteroatoms selected from N and S, optionally carbonyl function, and / or from one to four substituents A _'2, 5, 6 or 7 Saturated or unsaturated heterocycle Hy ₁ of atoms,
- _{halogen, NO 2, OCF 3, CF} 3, OR 4, OCH 2 R 4, COOR 4, C 1 ~C 10 alkyl group, and one selected from a hydrocarbon-based ring or a heterocyclic aromatic ring or 2 Phenyl ring specifically substituted by _two substituents A '' ₂ ,
-A phenyl ring fused to one or two hydrocarbon-based or heterocyclic rings of 5 to 6 atoms, thus representing one of those forming a condensed ring Use according to any one of claims 1 to 10. Hy ₁ is azetidine, pyrrole, dihydropyrrole, pyrrolidine, furan, dihydrofuran, tetrahydrofuran, thiophene, dihydrothiophene, tetrahydrothiophene, imidazole, dihydroimidazole, imidazolidine, dihydrothiazole, thiazolidine, dihydropyrazole, pyrazolidine, oxazole, dihydrooxazole , Oxazolidine, isoxazole, dihydroisoxazole, isoxazolidine, isothiazole, dihydroisothiazole, isothiazolidine, triazole, dihydrotriazole, triazolidine, oxadiazole, dihydrooxadiazole, oxadiazolidine, thiadiazole, dihydrothiadiazole, thiadiazolidine , Tetrazole, pyridine, dihydropyridine, teto Characterized in that it represents a heterocycle selected from lahydropyridine, piperidine, pyran, dihydropyran, tetrahydropyran, pyrimidine, dihydropyrimidine, tetrahydropyrimidine, piperazine, pyridazine, pyrazine, triazine, morpholine, azepine, diazepine Item 12. The use according to any one of Items 1 to 11. R ₃ is the following group:
-Phenyl group, COOR ₄ , OR ₄ , COR ₄ , CN, heterocycle containing 5 or 6 atoms and containing 1 or 2 heteroatoms selected from O, S and N, halogen A hydrocarbon base optionally substituted by one or more substituents A ′ '' ₂ selected from a linear or branched C ₁ -C ₁₀ alkyl group, a phenyl group optionally substituted by CN Wherein R ₄ represents hydrogen or a C _{1 to} C ₁₀ alkyl group,
A phenyl ring fused to one or two 5 to 6 atom hydrocarbon-based or heterocyclic ring C ⁴ , wherein ring C ⁴ optionally contains a carbonyl group and / or is saturated is optionally substituted by C ₁ -C ₁₀ alkyl group, the phenyl, is condensed in this or these ring C ^4, a phenyl ring to form a fused ring;
- characterized in that represents one of a saturated C ₁ -C ₁₀ alkyl group optionally substituted by one or two substituents A _1, according to any one of claims 1 to 12 Use of. Heterocycle _{Hy 2, Hy 4, Hy 6} , Hy 7, Hy 8, Hy 9, Hy 10 and Hy ₁₁ are independently azetidine ring, a pyrrole ring, dihydropyrrole ring, pyrrolidine ring, furan ring, dihydrofuran ring, Tetrahydrofuran ring, thiophene ring, dihydrothiophene ring, tetrahydrothiophene ring, imidazole ring, dihydroimidazole ring, imidazolidine ring, thiazole ring, dihydrothiazole ring, thiazolidine ring, pyrazole ring, dihydropyrazole ring, pyrazolidine ring, oxazole ring, dihydrooxazole Ring, oxazolidine ring, isoxazole ring, dihydroisoxazole ring, isoxazolidine ring, isothiazole ring, dihydroisothiazole ring, isothiazolidine ring, triazole ring, dihydrotriazole ring, triazolidine ring, oxadiazole ring, dihydr Droxadiazole ring, oxadiazolidine ring, thiadiazole ring, dihydrothiadiazole ring, thiadiazolidine ring, tetrazole ring, pyridine ring, dihydropyridine ring, tetrahydropyridine ring, piperidine ring, pyran ring, dihydropyran ring, tetrahydropyran ring, Indicate a pyrimidine ring, dihydropyrimidine ring, tetrahydropyrimidine ring, piperazine ring, pyridazine ring, pyrazine ring, triazine ring, morpholine ring, azepine ring, and diazepine ring, or a 15-C-5 crown ether for Hy ₉ 14. Use according to any one of claims 1 to 13, characterized by. Heterocycle Hy ₂ , Hy ₄ , Hy ₆ , Hy ₇ , Hy ₈ , Hy ₉ , Hy ₁₀ and Hy ₁₁ are independently pyrrole ring, pyrrolidine ring, imidazole ring, furan ring, thiophene ring, oxazole ring, thiazole ring , Isoxazole ring, isothiazole ring, oxadiazole ring, pyrazole ring, tetrazole ring, pyridine ring, pyrimidine ring, triazole ring, pyrazine ring, pyridazine ring, piperidine ring, piperazine ring or morpholine ring, or 15 for Hy ₉ 15. Use according to any one of claims 1 to 14, characterized by -C-5 crown ether. A ₁ represents a heterocycle or hydrocarbon-based ring containing 1 or 2 heteroatoms selected from O and N, wherein the hydrocarbon-based ring or heterocycle contains 5 to 6 atoms and any A carbonyl functional group and / or a substituent A ₃ ; or a group selected from including SiR ₄ R ′ ₄ R ″ ₄ , COOR ₄ , NR ₄ R ′ ₄ , OR ₄ , SR ₄ and CONR ₄ R ′ ₄ 16. Use according to any one of claims 1 to 15, characterized in that A ₃ is, C ₁ -C ₁₀ alkyl group, CF _3, characterized in that a halogen atom, OH or OCH _3, Use according to any one of claims 1 to 16. Hy ₁ represents γ-butyrolactone, piperidine or 1,3-benzodioxazole, optionally substituted with a C ₁ -C ₄ alkyl group, according to any one of claims 1 to 17, Use of description. Salts of compounds of formula (I) are sodium or potassium, ammonium, zinc (Zn ²⁺ ), calcium (Ca ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ and Fe ³⁺ ), strontium (Sr ²⁺ ), magnesium (Mg ²⁺ ) and manganese (Mn ²⁺ ), triethanolamine, monoethanolamine, diethanolamine, hexadecylamine and N, N , N ', N'-tetrakis (2-hydroxypropyl) ethylenediamine salt, hydroxide, hydrohalide, carbonate, bicarbonate, citrate, lactate, glycolate, gluconate, acetate, The salt according to any one of claims 1 to 18, characterized in that it is a salt selected from propionate, fumarate, oxalate, tartrate, sulfate, phosphate, and hydrogen phosphate. Use of description.   20. Use according to any one of claims 1 to 19, characterized in that the 2-oxyacetamide compound is in hydrate form. The 2-oxyacetamide compound has the following formula (1a):

Or a salt and / or solvate thereof,
Where:
α) R ₁₁ is:
1) at least one optionally substituted by substituents A ₄ C ₁ -C ₁₀ alkyl group,
2) selected from 5 to 6 atom hydrocarbon-based rings C ¹⁵ , optionally substituted by at least one substituent A ₅ ;
β) R ₁₂ is:
1) at least one optionally substituted by substituents A ₄ C ₁ -C ₁₀ alkyl group,
2) 5 to 6 atoms optionally fused to at least one ring C ¹⁷ of 5 to 6 atoms optionally containing at least one heteroatom to form heterocycle Hy ₁₇ The hydrocarbon-based ring C ¹⁶ is selected from: ring C ¹⁶ and ring C ¹⁷ optionally comprising a carbonyl functional group and / or substituted with at least one substituent A ₅ ;
γ) A ₄ is:
1) a 5 to 6 atom ring C ¹⁸ optionally containing at least one heteroatom to form a heterocycle Hy ₁₈ , wherein the ring or this heterocycle is OR ₁₄ , CF ₃ A ring C ¹⁸ optionally substituted with at least one substituent A ₆ selected from, halogen, and C ₁ -C ₁₀ alkyl groups,
2) R ₁₃ , R ′ ₁₃ , R ″ ₁₃ and R ′ ″ ₁₃ independently represent hydrogen or a C ₁ -C ₁₀ alkyl group, 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 COR' 13 R '' 13 , SO ₂ NR ₁₃ R ′ ₁₃ , NR ₁₃ SO ₂ R ′ ₁₃ , SO ₂ R ₁₃ , SiR ₁₃ R ′ ₁₃ R ″ ₁₃ and one of SO ₃ H;
δ) A ₅ is:
1) halogen,
2) R ₁₅ , R ′ ₁₅ and R ″ ₁₅ independently represent a group CF ₃ , CN, OR ₁₅ , SR ₁₅ representing a C ₁ -C ₁₀ alkyl group optionally substituted with hydrogen or a phenyl group. , one of _{NR 15 R '15, OCOR 15} , COR 15, COOR 15, SO 2 R 15, SiR 15 R' 15 R '' 15, NO 2 and OCF _3,
3) C ₁ ~C ₁₀ alkyl group which is optionally substituted by OR ₁₄ group,
4) selected from a 5 to 6 atom ring C ¹⁹ , optionally containing at least one heteroatom and / or possibly including a carbonyl function to form a heterocycle Hy ₁₉ ;
ε) R ₁₄ is:
1) hydrogen,
2) C ₁ ~C ₁₀ alkyl group is selected from;
η) Hy ₁₇ , Hy ₁₈ and Hy ₁₉ potentially contain 1 to 4 heterocycles independently selected from N, O and S and combinations thereof and / or contain carbonyl functional groups 21. Use according to any one of claims 1 to 20, characterized in that it represents a 5 to 6 atom heterocycle containing. 2-Oxyacetamide compounds are represented by the following formulas (II) to (V):
Formula (II):

Formula (III):

Formula (IV):

Formula (V):

Satisfy one or the corresponding salts and / or solvates thereof,
Where:
(i) R7 and R8 are independently:
1) hydrogen,
2) F or Cl halogen,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent a C _{1 to} C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group, and R ₆ and R ′ ₆ represent a phenyl group The groups CF ₃ , CN, OR ₄ , SR ₄ , NHR ₆ , NR ₆ R ′ ₆ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO represent an optionally substituted C ₁ -C ₂₀ alkyl group _{1 of 2} R ₄ , SiR ₄ R ' ₄ R'' ₄ , and OCF ₃ ,
4) R ₅ is, C ₁ -C ₂₀ alkyl group optionally substituted by OR ₅ groups represent hydrogen or C ₁ -C ₂₀ alkyl group,
5) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, wherein these ring C ¹¹ and ring C ¹² optionally contain a carbonyl function or a thiocarbonyl function:
(ii) z is the following ring and heterocycle:

Represents one of
(iii) X and Y independently represent hydrogen or A ₂ , or optionally contain at least one heteroatom and are optionally substituted with at least one substituent A ₂ to form another ring C ¹⁴ Can form a condensed ring C ¹³ of 4 to 7 atoms, optionally fused to
(iv) A is the following three groups:

Represents one of
(v) R ₃ has the same meaning as described above for formula (I),
However,
-When Z represents a dibenzofuran heterocycle, X and Y are independently:
1) hydrogen,
2) Halogen,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent a C _{1 to} C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group, and R ₉ is optionally substituted with hydrogen or a phenyl group. It represents a C ₂ -C ₂₀ alkyl group substituted, group _{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 , one of NO ₂ and OCF ₃ ,
4) C ₂ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
5) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, provided that these rings C ¹¹ and C ¹² represent optionally containing a carbonyl function or a thiocarbonyl function; or
-Z, ring:

Represents
X and Y are independently:
1) Hydrogen, in this case X is different from Y
2) Fluorine,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent a C _{1 to} C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group, and R ₆ is optionally substituted with a phenyl group. R ₁₀ represents a C ₁ -C ₂₀ alkyl group, and a group OR ₁₀ , SR ₄ , NR ₄ represents a C ₃ -C ₂₀ alkyl group optionally substituted by a hydrogen atom or a benzyl group or phenyl group one of _{R '4, OCOR 4, COR} 4, CSR 4, COOR 6, SiR 4 R' 4 R '' 4 and OCF _3,
4) C ₂ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
5) X and Y also can form a 5-atom ring C ^13, 1 one or two oxygen atoms and optionally containing, as representative of the rings C ¹³ fused to optionally another ring C ¹⁴ Condition,
Use according to any one of claims 1 to 21, characterized in that A compound of formula (I) has the following formula:
Compound 2

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

Use according to any one of claims 1 to 21, characterized in that one of them or a corresponding salt and / or solvate thereof is satisfied. The compound of formula (I) or a mixture of compounds of formula (I) is from 10 ⁻³ to 10% by weight of the total weight of the composition, preferably from 10 ⁻² to 2% by weight of the total weight of the composition 24. Use according to any one of claims 1 to 23, characterized in that it is used in a concentration of up to%.     Use according to any one of claims 1 to 24, characterized in that the composition is a composition for topical application. Physiologically acceptable medium and effective amount of formula (I):

Where:
a) R ₁ and R ₂ are
1) Hydrogen, where R ₁ is different from R ₂
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) 3 to 7 hydrocarbon-based ring C ¹ optionally fused to at least one ring C ² of 4 to 7 atoms, wherein ring C ² is a heterocycle Hy ₂ These ring C ¹ and ring C ² optionally contain at least one heteroatom to form a carbonyl function or a thiocarbonyl function and / or at least one substituent A ₂ Is replaced by,
4) A heterocyclic Hy ₁ fused to any of four of up to 7 atoms in the ring C ^2, the ring C ² is optionally at least one heteroatom to form a heterocyclic Hy ₂ In which these rings Hy ₁ and C ² optionally contain a carbonyl function or a thiocarbonyl function and / or are substituted by at least one substituent A ₁ ,
5) group C (= NR) R ', C (= NR) NR'R'', COR, CSR, COOR, CONRR', SO 2 R or SO ₂ NRR '
One of, independently selected;
b) R ₃ is
1) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
2) 3 to 7 optionally fused to at least one ring C ⁴ of 4 to 7 atoms optionally containing at least 1 heteroatom to form a heterocycle Hy ₄ A hydrocarbon-based ring C ³ of these atoms, wherein ring C ³ and ring C ⁴ optionally comprise a carbonyl function or a thiocarbonyl function and / or are substituted by at least one substituent A ₂ ing,
3) A heterocyclic Hy ₃ selected from a pyrrole ring, a furan ring, a thiophene ring and a pyrazole ring, optionally fused to a ring C ⁵ representing phenyl, pyridine or pyrimidine, wherein the heterocyclic Hy ₃ and the ring C ⁵ are Optionally substituted with at least one substituent A ₁ ,
4) Unlike Hy ₃ , a heterocycle Hy ₅ optionally fused to a ring C ⁶ of 4 to 7 atoms, which ring Hy ₅ and ring C ⁶ is a heterocycle Hy ₆ In order to form this ring C ⁶ optionally contains at least one heteroatom, possibly contains a carbonyl function or a thiocarbonyl function and / or is substituted by at least one substituent A ₁ Is selected from;
c) R, R 'and R''are:
1) hydrogen,
2) at least one optionally substituted by substituents A ₁ C ₁ -C ₂₀ alkyl group,
3) 4 to ₇ optionally containing at least one heteroatom to form heterocycle Hy ₇ and / or optionally containing at least one heteroatom to form heterocycle Hy ₈ a ring C ⁷ atoms from four fused to an optionally ring C ⁸ atoms up pieces up to 7, optionally substituted by rings C ⁷ and ring C ⁸ is at least one substituent a ₁ Independently selected from, optionally including a carbonyl function or a thiocarbonyl function;
d) A ₁ is:
1) halogen,
2) C ₁ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
3) optionally contain at least one hetero atom to form a heterocyclic ring Hy _9, and / or 15 in atom ring C ¹⁰ of from four to seven from four fused to optionally Ring C ⁹ of atoms up to, wherein these ring C ⁹ and ring C ¹⁰ are selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C _{1 to} C ₂₀ alkyl groups Optionally containing at least one substituent A ₃
4) R ₄ , R ′ ₄ , R ″ ₄ and R ′ ″ ₄ are independently C ₁ -C ₂₀ alkyl optionally substituted with hydrogen or heterocyclic Hy ₁₀ or CONR ₅ R ′ ₅ group 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 , selected from Si (OR ₄ ) (OR' ₄ ) OR '' ₄ , and one of SO ₃ H;
e) A ₂ is:
1) halogen,
2) R ₄ , R ′ ₄ and R ″ ₄ independently represent a group CF ₃ , CN, OR ₄ , SR ₄ which represents a C ₁ -C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group. , NR ₄ R ' ₄ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO ₂ R ₄ , SiR ₄ R' ₄ R '' ₄ , one of NO ₂ and OCF ₃ ,
3) C ₁ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
4) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, wherein these ring C ¹¹ and ring C ¹² are selected from carbonyl or thiocarbonyl functions and / or OR ₅ , CF ₃ , halogen and C ₁ -C ₂₀ alkyl groups that at least one substituent a ₃ possibly is selected from;
f) R ₅ and R ' ₅ are
1) hydrogen,
2) C ₁ ~C ₂₀ alkyl group, independently selected from;
g) Hy ₁ , Hy ₂ , Hy ₄ to Hy ₈ , Hy ₁₀ and Hy ₁₁ are independently selected from N, O and S and combinations thereof, and / or have a carbonyl or thiocarbonyl function. Represents a heterocycle of 4 to 7 atoms potentially containing 1 to 4 heteroatoms inclusive;
h) Hy ₉ optionally contains 1 to 5 heteroatoms selected from N, O and S and combinations thereof and / or 4 containing carbonyl or thiocarbonyl functions A composition for the care and / or make-up of keratin fibers, comprising at least one compound or a salt and / or solvate thereof representing a heterocycle of from 1 to 15 atoms. R ₁ represents hydrogen and R ₂ represents the following group:
- one or two optionally substituted by substituents A ₁ saturated C ₁ -C ₁₀ alkyl group,
-Saturated hydrocarbon-based rings of 3 to 6 carbon atoms,
-5, 6 or 7 containing 1 to 2 heteroatoms selected from O, N and S, optionally containing a carbonyl function and / or 1 to 4 substituents A ′ ₂ Saturated or unsaturated heterocycle Hy _{1 of} a number of atoms,
- _{halogen, NO 2, OCF 3, CF} 3, OR 4, OCH 2 R 4, COOR 4, C 1 ~C 10 alkyl group, and one selected from a hydrocarbon-based ring or a heterocyclic aromatic ring or 2 Phenyl ring specifically substituted by _two substituents A '' ₂ ,
-A phenyl ring fused to one or two hydrocarbon-based or heterocyclic rings of 5 to 6 atoms, thus representing one of those forming a condensed ring 27. The composition of claim 26. Hy ₁ is azetidine, pyrrole, dihydropyrrole, pyrrolidine, furan, dihydrofuran, tetrahydrofuran, thiophene, dihydrothiophene, tetrahydrothiophene, imidazole, dihydroimidazole, imidazolidine, dihydrothiazole, thiazolidine, dihydropyrazole, pyrazolidine, oxazole, dihydrooxazole , Oxazolidine, isoxazole, dihydroisoxazole, isoxazolidine, isothiazole, dihydroisothiazole, isothiazolidine, triazole, dihydrotriazole, triazolidine, oxadiazole, dihydrooxadiazole, oxadiazolidine, thiadiazole, dihydrothiadiazole, thiadiazolidine , Tetrazole, pyridine, dihydropyridine, teto Characterized in that it represents a heterocycle selected from lahydropyridine, piperidine, pyran, dihydropyran, tetrahydropyran, pyrimidine, dihydropyrimidine, tetrahydropyrimidine, piperazine, pyridazine, pyrazine, triazine, morpholine, azepine, diazepine Item 26. The composition according to item 26 or 27. R ₃ is the following group:
-Phenyl group, COOR ₄ , OR ₄ , COR ₄ , CN, heterocycle containing 5 or 6 atoms and containing 1 or 2 heteroatoms selected from O, S and N, halogen , a phenyl group optionally substituted by CN, a C ₁ -C ₁₀ alkyl by groups one selected from or more substituents a ''_'2 hydrocarbon-based substituted optionally ring, R ₄ represents hydrogen or a C _{1 to} C ₁₀ alkyl group,
A phenyl ring fused to one or two 5 to 6 atom hydrocarbon-based or heterocyclic ring C ⁴ , wherein ring C ⁴ optionally contains a carbonyl group and / or is saturated is optionally substituted by C ₁ -C ₁₀ alkyl group, the phenyl, is condensed in this or these ring C ^4, a phenyl ring to form a fused ring;
- characterized in that represents one of a saturated C ₁ -C ₁₀ alkyl group optionally substituted by one or two substituents A _1, according to any one of claims 26 to 28 Composition. Heterocycle _{Hy 2, Hy 4, Hy 6} , Hy 7, Hy 8, Hy 9, Hy 10 and Hy ₁₁ are independently azetidine ring, a pyrrole ring, dihydropyrrole ring, pyrrolidine ring, furan ring, dihydrofuran ring, Tetrahydrofuran ring, thiophene ring, dihydrothiophene ring, tetrahydrothiophene ring, imidazole ring, dihydroimidazole ring, imidazolidine ring, thiazole ring, dihydrothiazole ring, thiazolidine ring, pyrazole ring, dihydropyrazole ring, pyrazolidine ring, oxazole ring, dihydrooxazole Ring, oxazolidine ring, isoxazole ring, dihydroisoxazole ring, isoxazolidine ring, isothiazole ring, dihydroisothiazole ring, isothiazolidine ring, triazole ring, dihydrotriazole ring, triazolidine ring, oxadiazole ring, dihydr Droxadiazole ring, oxadiazolidine ring, thiadiazole ring, dihydrothiadiazole ring, thiadiazolidine ring, tetrazole ring, pyridine ring, dihydropyridine ring, tetrahydropyridine ring, piperidine ring, pyran ring, dihydropyran ring, tetrahydropyran ring, Indicate a pyrimidine ring, dihydropyrimidine ring, tetrahydropyrimidine ring, piperazine ring, pyridazine ring, pyrazine ring, triazine ring, morpholine ring, azepine ring, and diazepine ring, or a 15-C-5 crown ether for Hy ₉ 30. Composition according to any one of claims 26 to 29, characterized in that Heterocycle Hy ₂ , Hy ₄ , Hy ₆ , Hy ₇ , Hy ₈ , Hy ₉ , Hy ₁₀ and Hy ₁₁ are independently pyrrole ring, pyrrolidine ring, imidazole ring, furan ring, thiophene ring, oxazole ring, thiazole ring , Isoxazole ring, isothiazole ring, oxadiazole ring, pyrazole ring, tetrazole ring, pyridine ring, pyrimidine ring, triazole ring, pyrazine ring, pyridazine ring, piperidine ring, piperazine ring or morpholine ring, or 15 for Hy ₉ 31. Composition according to any one of claims 26 to 30, characterized in that it represents -C-5 crown ether. A ₁ represents a hydrocarbon-based ring or heterocycle containing 1 or 2 heteroatoms selected from O and N, wherein the hydrocarbon-based ring or heterocycle contains 5 to 6 atoms and any Includes a group selected from a carbonyl functional group and / or a substituent A ₃ ; or SiR ₄ R ′ ₄ R ″ ₄ , COOR ₄ , NR ₄ R ′ ₄ , OR ₄ , SR ₄ and CONR ₄ R ′ ₄ 32. A composition according to any one of claims 26 to 31, characterized in that A ₃ is, C ₁ -C ₁₀ alkyl group, CF _3, characterized in that a halogen atom, OH or OCH _3, A composition according to any one of claims 26 to 32. R ₄ , R ′ ₄ , R ″ ₄ , and ₄ R ′ ″ ₄ represent hydrogen, a phenyl group, or a C ₁ -C ₁₀ alkyl group, according to claim 26. 2. The composition according to item 1. Hy ₁ is, C ₁ -C ₄ optionally substituted by alkyl 1,3 benzodioxazole, .gamma.-butyrolactone or, characterized in that represent a piperidine, any one of claims 26 to 34, A composition according to 1. Salts of compounds of formula (I) are sodium or potassium, ammonium, zinc (Zn ²⁺ ), calcium (Ca ²⁺ ), copper (Cu ²⁺ ), iron (Fe ²⁺ and Fe ³⁺ ), strontium (Sr ²⁺ ), magnesium (Mg ²⁺ ) and manganese (Mn ²⁺ ), triethanolamine, monoethanolamine, diethanolamine, hexadecylamine and N, N , N ', N'-tetrakis (2-hydroxypropyl) ethylenediamine salt, hydroxide, hydrohalide, carbonate, bicarbonate, citrate, lactate, glycolate, gluconate, acetate, 36. A salt according to any one of claims 26 to 35, characterized in that it is a salt selected from propionate, fumarate, oxalate, tartrate, sulfate, phosphate and hydrogen phosphate. The composition as described.   37. Composition according to any one of claims 26 to 36, characterized in that the 2-oxyacetamide compound is in hydrate form. The 2-oxyacetamide compound has the following formula (1a):

Or a salt and / or solvate thereof,
Where:
α) R ₁₁ is:
1) at least one optionally substituted by substituents A ₄ C ₁ -C ₁₀ alkyl group,
2) selected from 5 to 6 atom hydrocarbon-based rings C ¹⁵ , optionally substituted by at least one substituent A ₅ ;
β) R ₁₂ is:
1) at least one optionally substituted by substituents A ₄ C ₁ -C ₁₀ alkyl group,
2) 5 to 6 atoms optionally fused to at least one ring C ¹⁷ of 5 to 6 atoms optionally containing at least one heteroatom to form heterocycle Hy ₁₇ A hydrocarbon-based ring C ¹⁶ of which is selected from ring C ¹⁶ and ring C ¹⁷ optionally comprising a carbonyl functional group and / or substituted with at least one substituent A ₅ ;
γ) A ₄ is:
1) a 5 to 6 atom ring C ¹⁸ optionally containing at least one heteroatom to form a heterocycle Hy ₁₈ , wherein the ring or heterocycle is OR ₁₄ , CF ₃ , halogen, and C ₁ by at least one substituent a ₆ is selected from -C ₁₀ alkyl group, optionally substituted,
2) R ₁₃ , R ′ ₁₃ , R ″ ₁₃ and R ′ ″ ₁₃ independently represent hydrogen or a C ₁ -C ₁₀ alkyl group, 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 COR' 13 R '' 13 , SO ₂ NR ₁₃ R ′ ₁₃ , NR ₁₃ SO ₂ R ′ ₁₃ , SO ₂ R ₁₃ , SiR ₁₃ R ′ ₁₃ R ″ ₁₃ and one of SO ₃ H;
δ) A ₅ is:
1) halogen,
2) R ₁₅ , R ′ ₁₅ and R ″ ₁₅ independently represent a group CF ₃ , CN, OR ₁₅ , SR ₁₅ representing a C ₁ -C ₁₀ alkyl group optionally substituted with hydrogen or a phenyl group. , one of _{NR 15 R '15, OCOR 15} , COR 15, COOR 15, SO 2 R 15, SiR 15 R' 15 R '' 15, NO 2 and OCF _3,
3) C ₁ ~C ₁₀ alkyl group which is optionally substituted by OR ₁₄ group,
4) selected from a 5 to 6 atom ring C ¹⁹ , optionally containing at least one heteroatom and / or possibly including a carbonyl function to form a heterocycle Hy ₁₉ ;
ε) R ₁₄ is:
1) hydrogen,
2) C ₁ ~C ₁₀ alkyl group is selected from;
η) Hy ₁₇ , Hy ₁₈ and Hy ₁₉ potentially contain 1 to 4 heterocycles independently selected from N, O and S and combinations thereof and / or contain carbonyl functionality. 38. A composition according to any one of claims 26 to 37, characterized in that it represents a 5 to 6 atom heterocycle containing. 2-Oxyacetamide compounds are represented by the following formulas (II) to (V):
Formula (II):

Formula (III):

Formula (IV):

Formula (V):

Satisfy one or the corresponding salts and / or solvates thereof,
Where:
(i) R7 and R8 are independently:
1) hydrogen,
2) F or Cl halogen,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent a C _{1 to} C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group, and R ₆ and R ′ ₆ represent a phenyl group The groups CF ₃ , CN, OR ₄ , SR ₄ , NHR ₆ , NR ₆ R ′ ₆ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO represent an optionally substituted C ₁ -C ₂₀ alkyl group _{1 of 2} R ₄ , SiR ₄ R ' ₄ R'' ₄ , and OCF ₃ ,
4) R ₅ is, C ₁ -C ₂₀ alkyl group optionally substituted by OR ₅ groups represent hydrogen or C ₁ -C ₂₀ alkyl group,
5) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, wherein these ring C ¹¹ and ring C ¹² optionally contain a carbonyl function or a thiocarbonyl function:
(ii) z is the following ring and heterocycle:

Represents one of
(iii) X and Y are either independently hydrogen or A _2, or, optionally contain at least one N, O, heteroatoms selected from S, and combinations thereof, at least one substituent optionally substituted with a _2, is optionally fused to a another ring C ^14, from 4 to 7, can be better still form a fused ring C ¹³ atoms from 5 to 6;
(iv) A is the following three groups:

Represents one of
(v) R ₃ has the same meaning as described above for formula (I),
However,
-When Z represents a dibenzofuran heterocycle, X and Y are independently:
1) hydrogen,
2) Halogen,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent a C _{1 to} C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group, and R ₉ is optionally substituted with hydrogen or a phenyl group. It represents a C ₂ -C ₂₀ alkyl group substituted, group _{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 , one of NO ₂ and OCF ₃ ,
4) C ₂ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
5) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, provided that they represent ring C ¹¹ possibly containing a carbonyl function or a thiocarbonyl function; or
-Z, ring:

Represents
X and Y are independently:
1) Hydrogen, in this case X is different from Y
2) Fluorine,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent a C _{1 to} C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group, and R ₆ is optionally substituted with a phenyl group. R ₁₀ represents a C ₁ -C ₂₀ alkyl group, and a group OR ₁₀ , SR ₄ , NR ₄ represents a C ₃ -C ₂₀ alkyl group optionally substituted by a hydrogen atom or a benzyl group or phenyl group one of _{R '4, OCOR 4, COR} 4, CSR 4, COOR 6, SiR 4 R' 4 R '' 4 and OCF _3,
4) C ₂ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
5) X and Y also can form a 5-atom ring C ^13, 1 one or two oxygen atoms and optionally containing, as representative of the rings C ¹³ fused to optionally another ring C ¹⁴ Condition,
A composition according to any one of claims 26 to 38, characterized in that A compound of formula (I) has the following formula:
Compound 2

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

40. Composition according to any one of claims 26 to 39, characterized in that one of them or a corresponding salt and / or solvate thereof is satisfied. The compound of formula (I) or a mixture of compounds of formula (I) is 10 ⁻³ to 10% by weight of the total weight of the composition, preferably 10 ⁻² to 2% by weight of the total weight of the composition 41. Composition according to any one of claims 26 to 40, characterized in that it is used in a concentration of up to%.   42. Composition according to any one of claims 26 to 41, characterized in that the composition is in the form of a hair cream or hair lotion, a shampoo, a conditioner or a hair or eyelash mascara.   43. Composition according to any one of claims 26 to 42, characterized in that the composition is in the form of an aqueous, alcoholic or aqueous-alcoholic liquid solution or suspension.   Compositions include solvents, aqueous or oil phase thickeners or gelling agents, dyes that can be dissolved in the composition medium, fillers, pigments, antioxidants, preservatives, fragrances, electrolytes, neutralizing agents, films 45. Other additional ingredients selected from forming polymers, UV blockers, cosmetic and pharmaceutical actives other than compounds of formula (I), and mixtures thereof, characterized in that The composition of any one of these.   The composition also includes proteins or protein hydrolysates, amino acids, polyols, urea, allantoin, sugars and sugar derivatives, water-soluble vitamins, plant extracts, hydroxy acids; retinol and derivatives thereof, tocophenols and derivatives thereof, essential fatty acids, 45. Any one of claims 26 to 44, characterized in that it contains at least one active agent selected from ceramides, essential oils, salicylic acid derivatives, hydroxy acid esters, and phospholipids, and mixtures thereof. A composition according to 1.   46. Composition according to any one of claims 26 to 45, characterized in that the composition comprises at least one further active compound that promotes the regeneration and / or limits the loss of keratin fibres.   Further active compounds are aminexil, 6-0-[(9Z, 12Z) octadeca-9,12-dienoyl] hexapyranose, lipoxygenase inhibitors, bradykinin inhibitors, prostaglandins and their derivatives, prostaglandin receptor agonists Or antagonists, non-prostanoic acid prostaglandin analogs, vasodilators, antiandrogens, cyclosporine and their analogs, antifungal agents, anti-inflammatory agents, retinoids, benzalkonium chloride, benzethonium chloride, phenol, estradiol, malein Acid chlorpheniramine, chlorophyllin derivative, cholesterol, cysteine, methionine, menthol, peppermint oil, calcium pantothenate, panthenol, resorcinol, protein kinase C activator, glycosidase inhibitor, glyco Minoglycanase inhibitors, pyroglutamate esters, hexosaccharides or acylhexosaccharide acids, substituted arylethylenes, N-acylamino acids, flavonoids, ascomycin derivatives and analogs, histamine antagonists, saponins, proteoglycanase inhibitors, estrogen agonists and antagonists, Pseudoterin, cytokine, growth factor promoter, IL-1 or IL-6 inhibitor, IL-10 promoter, TNF inhibitor, vitamins, benzophenone, hydantoin, retinoic acid, anti-eclamptic agent, antiparasitic agent, antifungal agent, Calcium antagonists, hormones, triterpenes, antiandrogens, steroidal or non-steroidal 5α-reductase inhibitors, potassium channel agonists, and FP receptor antagonists, and Wherein the mixtures thereof The composition of claim 46.   In a physiologically acceptable medium, in particular a cosmetic medium, at least one compound of formula (I) or a salt and / or solvate thereof and aminexyl, FP receptor agonist, prostaglandins and their derivatives, blood vessels A composition for the care and / or makeup of keratin fibers comprising at least one further active agent selected from dilators that promotes the regeneration of keratin fibers and / or delays the loss of keratin fibers.   Further active agents are aminexyl, minoxidil, latanoprost, (5E) -7-{(1R, 2R, 3R, 5S) -3,5-dihydroxy-2-[(3R) -3-hydroxy-5-phenylpentyl] 49. Composition according to any one of claims 46 to 48, characterized in that it is selected from cyclopentyl} hept-5-enoic acid, butaprost and travoprost.   A cosmetic method for treating human keratin fibers and / or skin in which the fibers appear in order to improve human keratin fibers and / or the appearance and / or appearance of the skin in which the fibers appear, comprising the keratin fibers And / or applying a cosmetic composition to the skin, the cosmetic composition comprising at least one compound of formula (I) or a salt and / or solvate thereof, said composition comprising keratin A cosmetic method comprising contacting fibers and / or the skin where the fibers appear, and optionally rinsing the fibers and / or the skin.   A cosmetic method for treating hair and / or scalp comprising applying a cosmetic composition to the hair and / or scalp, the composition comprising at least one compound of formula (I) or A cosmetic method comprising the salt and / or solvate, wherein the composition is contacted with hair and / or scalp, and optionally the hair and / or scalp is rinsed.   A cosmetic method for caring for and / or making up human eyelashes to improve the condition and / or appearance of human eyelashes, comprising applying a mascara composition to eyelashes and / or eyelids. A cosmetic method characterized by comprising at least one compound of formula (I) or a salt and / or solvate thereof, wherein the composition is contacted with eyelashes and / or eyelids. From the following formula (II) to (V):
Formula (II):

Formula (III):

Formula (IV):

Formula (V):

Or one of its corresponding salts and / or solvates,
Where:
(i) R7 and R8 are independently:
1) hydrogen,
2) F or Cl halogen,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent a C _{1 to} C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group, and R ₆ and R ′ ₆ represent a phenyl group The groups CF ₃ , CN, OR ₄ , SR ₄ , NHR ₆ , NR ₆ R ′ ₆ , OCOR ₄ , COR ₄ , CSR ₄ , COOR ₄ , SO represent an optionally substituted C ₁ -C ₂₀ alkyl group _{1 of 2} R ₄ , SiR ₄ R ' ₄ R'' ₄ , and OCF ₃ ,
4) R ₅ is, C ₁ -C ₂₀ alkyl group optionally substituted by OR ₅ groups represent hydrogen or C ₁ -C ₂₀ alkyl group,
5) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, wherein these ring C ¹¹ and ring C ¹² optionally contain a carbonyl function or a thiocarbonyl function:
(ii) z is the following ring and heterocycle:

Represents one of
(iii) X and Y are either independently hydrogen or A _2, or, optionally containing at least one N, O, S, and heteroatoms selected from combinations thereof, at least one substituent optionally substituted by a group a _2, and optionally fused to a another ring C ^14, from 4 to 7, better still form a fused ring C ¹³ five person of up to 6 atoms Can;
(iv) A is the following three groups:

Represents one of
(v) R ₃ has the same meaning as described above for formula (I),
However,
-When Z represents a dibenzofuran heterocycle, X and Y are independently:
1) hydrogen,
2) Halogen,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent a C _{1 to} C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group, and R ₉ is optionally substituted with hydrogen or a phenyl group. It represents a C ₂ -C ₂₀ alkyl group substituted, group _{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 , one of NO ₂ and OCF ₃ ,
4) C ₂ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
5) 4 to 7 optionally containing at least one heteroatom and / or optionally fused to a ring C ¹² of 4 to 7 atoms to form a heterocycle Hy ₁₁ Ring C ¹¹ of atoms up to, provided that they represent ring C ¹¹ possibly containing a carbonyl function or a thiocarbonyl function; or
-Z, ring:

Represents
X and Y are independently:
1) Hydrogen, in this case X is different from Y
2) Fluorine,
3) R ₄ , R ′ ₄ and R ″ ₄ independently represent a C _{1 to} C ₂₀ alkyl group optionally substituted with hydrogen or a phenyl group, and R ₆ is optionally substituted with a phenyl group. R ₁₀ represents a C ₁ -C ₂₀ alkyl group, and a group OR ₁₀ , SR ₄ , NR ₄ represents a C ₃ -C ₂₀ alkyl group optionally substituted by a hydrogen atom or a benzyl group or phenyl group one of _{R '4, OCOR 4, COR} 4, CSR 4, COOR 6, SiR 4 R' 4 R '' 4 and OCF _3,
4) C ₂ ~C ₂₀ alkyl group optionally substituted by OR ₅ group,
5) X and Y also can form a 5-atom ring C ^13, 1 one or two oxygen atoms and optionally containing, as representative of the rings C ¹³ fused to optionally another ring C ¹⁴ Condition,
2-oxyacetamide compound characterized by the above-mentioned. The following formula:
Compound 2:

Compound 3:

Compound 12:

Compound 13:

Compound 21:

54. The compound of claim 53, satisfying one of: