Compounds of the quinolone family and their uses in cosmetics

Abstract

Compounds of the quinolone family and their uses in cosmetics The present invention relates to the cosmetic use of at least one compound of formula (I) or its tautomeric form (I'), or one of their salts, and / or solvates and / or isomers for the care of keratin materials, in particular the skin. It also relates to the use of at least one compound of formula (II) or its tautomeric form (II'), or one of their salts, solvates and / or isomers for improving the skin signs of aging, and in particular as an anti-aging active agent. It also relates to a cosmetic composition which comprises at least one compound of formula (I) or its tautomeric form (I'), or one of their salts, solvates and / or isomers. Figure for the abstract: none

Description

Title of the invention: Compounds of the quinolone family and their uses in cosmetics

[0001] The present invention relates to the cosmetic use of at least one compound of formula (I) or its tautomeric form (I'), or one of their salts, and / or solvates and / or isomers for the care of keratin materials, in particular the skin. It also relates to the use of at least one compound of formula (II) or its tautomeric form (II'), or one of their salts, solvates and / or isomers for improving the cutaneous signs of aging, and in particular as an anti-aging active agent.

[0002] It also relates to a cosmetic composition which comprises at least one compound of formula (I) or its tautomeric form (I'), or one of their salts, solvates and / or isomers.

[0003] The outer layer of the skin, the epidermis, is stratified and composed mainly of three types of cells which are keratinocytes, which are the vast majority, melanocytes and Langerhans cells. Each of these cell types contributes through its own functions to the essential role played in the body by the skin, in particular the role of protecting the body against external aggressions (climate, ultraviolet rays, tobacco, pollution, etc.).

[0004] The alterations associated with skin aging can manifest themselves in different ways, among which we can cite:

[0005] - a microrelief characterized in particular by the appearance of fine wrinkles or fine lines, or also by the presence of visible pores in significant density, by a roughness altering the surface appearance of the skin;

[0006] - loss of radiance, which leads to uneven skin tone;

[0007] - a loss of elasticity, suppleness, firmness, density, tone of the skin, a sagging and / or wilting of the skin;

[0008] - a slowdown in epidermal renewal leading to thinning of the horny layer of the skin and a papery appearance of the skin;

[0009] - and skin dryness resulting from a reduction in the barrier function of the horny layer of the skin.

[0010] Among the anti-aging active ingredients available, retinol is unanimously known to be effective on the signs of skin aging, and thus, used to treat a wide range of skin problems, in particular to treat wrinkles and fine lines, and more generally to improve radiance.

[0011] However, the use of retinol can be limited by its instability, its sensitivity to oxidation, to light, to heat, but also its spontaneous degradation in the time. The instability of retinol therefore requires special precautions for proper formulation and use.

[0012] There is therefore a need to provide new active ingredients that are effective against the signs of skin aging, stable and easier to formulate.

[0013] The present invention meets this need. Indeed, as demonstrated in particular by example, the Applicant has identified compounds belonging to the quinolone family, effective in stimulating cell proliferation and epidermal cell renewal. Summary of the invention

[0014] The present invention thus relates to the cosmetic use of at least one compound chosen from the compounds of formula (II) or its tautomeric form (II'):

[0015] [Chem.l]

[0016] (II)

[0017] [Chem.l]

[0018] (II')

[0019] Where: - RI to R4 identical or different represent: • H, • a linear C1-C4 or branched C3-C4 alkyl radical optionally substituted by OH or halogen;

[0020] preferably RI to R4 are identical and represent H; - R5 represents: • a linear or branched, saturated or monovalent Cl-Cl 1 hydrocarbon radical unsaturated, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7, and / or said radical being optionally interrupted by O, NR7, S, CO or their combinations such as (thio)ester or (thio)amide(s) -C(X)-N(R')- or -N(R')-C(X)- in which X = O or S and R' denotes a hydrogen atom or a linear C1-C4 or branched C3-C4 alkyl radical;

[0021] preferably R5 is unsubstituted and / or uninterrupted and / or saturated; more preferably R5 is saturated in C3-C11, even more preferably in C5-C9 such as C7; - R6 represents: • H, • OR7, • a linear or branched, saturated or monovalent Cl-Cl 1 hydrocarbon radical unsaturated, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7, and / or said radical being optionally interrupted by O, NR7, S, CO or their combinations such as (thio)ester or (thio)amide(s) -C(X)-N(R')- or -N(R')-C(X)- in which X = O or S and R' denotes a hydrogen atom or a linear C1-C4 or branched C3-C4 alkyl radical; preferably unsubstituted and / or uninterrupted and / or saturated; more preferably saturated in C3-C11, even more preferably in C5-C9 such as C7;

[0022] preferably R6 represents H, OR7, more preferably OR7 and even more preferably OH; - R7 represents: • H, • a linear C1-C4 or branched C3-C4 alkyl radical,

[0023] preferably R7 represents H; - R8 represents: • H, • a C1-C4 alkyl radical,

[0024] preferably R8 represents H

[0025] or R7 and R8 can form together with the nitrogen atom which carries them a heterocycle of 5 to 8 members, preferably of 5 or 6 members, said heterocycle being optionally substituted by one or more identical or different radicals chosen from a linear C1-C4 or branched C3-C4 alkyl radical and OH;

[0026] or one of its salts, and / or solvates and / or isomers,

[0027] as an anti-aging active agent.

[0028] The present invention relates in particular to the cosmetic use of at least one compound chosen from the compounds of formula (II) or its tautomeric form (II') or one of their salts, and / or solvates and / or isomers, to improve the cutaneous signs of aging.

[0029] The present invention also relates to a cosmetic skin care treatment method comprising the application to skin showing signs of cutaneous aging, of a cosmetic composition comprising in a physiologically acceptable medium, at least one compound of formula (II) or its tautomeric form (II') or one of their salts, and / or solvates, and / or isomers.

[0030] The present invention also relates to a cosmetic composition, in particular for the prevention and / or treatment of the signs of aging, comprising in a physiologically acceptable medium, at least one compound of formula (I) or its tautomeric form (I'):

[0031] [Chem.2]

[0032] (I)

[0033] [Chem.2]

[0034] (I')

[0035] Where: - RI to R4 identical or different represent: • H, • a linear C1-C4 or branched C3-C4 alkyl radical optionally substituted by OH or halogen,

[0036] preferably R1 to R4 are identical and represent H; - R5 represents a linear monovalent Cl-Cl 1 hydrocarbon radical or branched, saturated or unsaturated, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7, and / or said radical being optionally interrupted by O, NR7, S, CO or their combinations such as (thio)ester or (thio)amide(s) -C(X)-N(R')- or -N(R')-C(X)- in which X = O or S and R' denotes a hydrogen atom or a linear C1-C4 or branched C3-C4 alkyl radical; preferably R5 is unsubstituted and / or uninterrupted and / or saturated; more preferably R5 is saturated at C3-C11, even more preferably at C5-C9 such as C7; R6 represents: OR7, a linear or branched, saturated or unsaturated monovalent C1-C1 alkyl radical, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7, and / or said radical being optionally interrupted by O, NR7, S, CO or their combinations such as (thio)ester or (thio)amide(s) -C(X)-N(R')- or -N(R')-C(X)- in which X = O or S and R' denotes a hydrogen atom or a linear C1-C4 or branched C3-C4 alkyl radical; preferably unsubstituted and / or uninterrupted and / or saturated; more preferably saturated in C3-C11, even more preferably in C5-C9 such as C7;

[0037] preferably R6 represents OR7, more preferably OH; R7 represents: H, a linear C1-C4 or branched C3-C4 alkyl radical,

[0038] preferably R7 represents H; R8 represents: H, a linear C1-C4 or branched C3-C4 alkyl radical,

[0039] preferably R8 represents H;

[0040] or R7 and R8 can form together with the nitrogen atom which carries them a heterocycle of 5 to 8 members, preferably of 5 or 6 members, said heterocycle being optionally substituted by one or more identical or different radicals chosen from a C1-C4 alkyl radical and OH;

[0041] or one of its salts, and / or solvates and / or isomers.

[0042] The present invention also relates to the use of a compound of formula (I) or its tautomeric form (!), or one of their salts, solvates and / or isomers for the care of keratin materials, in particular the skin, more particularly for improving the cutaneous signs of aging and / or as an anti-aging active ingredient.

[0043] The present invention also relates to a cosmetic treatment method skin care comprising the application to the skin, preferably to skin showing signs of cutaneous aging, of a cosmetic composition comprising in a physiologically acceptable medium, at least one compound of formula (I) or its tautomeric form (!) or one of their salts, and / or solvates, and / or isomers. Definitions

[0044] “Keratin materials” means the skin of the body or face, the lips, the mucous membranes, the eyelashes, the nails, and the hair of a human being.

[0045] By "skin" is meant the entire skin of the body and the scalp of a human being and preferably, the skin of the face, the décolleté, the neck, the arms and forearms, the hands or even more preferably, the skin of the face (in particular the forehead, nose, cheeks, lips, chin), the décolleté and the neck.

[0046] For the purposes of the present invention, the term "unsaturated monovalent hydrocarbon radical" means a monovalent hydrocarbon radical comprising at least one ethylenic unsaturation, said unsaturations being conjugated or not, preferably "unsaturated monovalent hydrocarbon radical" denotes a hydrocarbon radical comprising one ethylenic unsaturation.

[0047] For the purposes of the present invention, the term "heterocycle" means a cyclic radical of which at least one of the links is a heteroatom preferably chosen from N, O, S, said cyclic radical being saturated or unsaturated, preferably saturated, said cyclic radical being optionally substituted.

[0048] The term “salt” of a compound of formula (I), (I'), (II) or (II') according to the invention means a salt formed by an inorganic or organic acid or an inorganic or organic base.

[0049] Examples of acid salts include sulfate, citrate, acetate, oxalate, chloride, bromide, iodide, nitrate, bisulfate, phosphate, isonicotinate, lactate, salicylate, citrate, tartrate, oleate, tannate, pantothenate, bitartrate, ascorbate, succinate, maleate, gentisinate, fumarate, gluconate, glucuronate, saccharate, formate, benzoate, glutamate, methanesulfonate, ethanesulfonate, benzenesulfonate, p-toluenesulfonate and pamoate (i.e. 1,1'-methylene-bis-(2-hydroxy-3-naphthoate).

[0050] Examples of basic salts include alkali metal hydroxides such as sodium, potassium and lithium; alkaline earth metal hydroxides such as calcium and magnesium; hydroxides of other metals, such as aluminum and zinc; ammonia and organic amines such as unsubstituted or hydroxy-substituted mono-, di- or tri-alkylamines; dicyclohexylamines; tributylamines; pyridine; N-methyl-N-ethylamine; diethylamine; triethylamine; mono-, bis- or tris-(2-hydroxy-alkylamines) such as mono-, bis- or tris-(2-hydroxyethyl)amine, 2-hydroxy-tert-butylamine, ortris- (hydroxymethyl)methylamine, N,N-di-alkyl-N-(hydroxyalkyl)-amines, such as N,N-dimethyl-N-(2-hydroxyethyl)amine or tri-(2-hydroxyethyl)amine; N-methyl-D-glucamine; and amino acids such as arginine and lysine.

[0051] A salt of a compound of formula (I), (!'), (II) or (II') according to the invention is preferably a base salt, and in particular a sodium or potassium salt. Detailed description Compounds of formula (II) and formula (I)

[0052] The compounds of formula (II) and its tautomeric form (II') are as follows:

[0053] [Chem.l]

[0054] (II)

[0055] [Chem.l]

[0056] (II')

[0057] Where: - RI to R4 identical or different represent: • H, • a linear C1-C4 or branched C3-C4 alkyl radical optionally substituted by OH or halogen;

[0058] preferably RI to R4 are identical and represent H; - R5 represents: • a linear or branched, saturated or unsaturated monovalent Cl-Cl 1 hydrocarbon radical, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7, and / or said radical being optionally interrupted by O, NR7, S, CO or their combinations such that (thio)ester or (thio)amide(s) -C(X)-N(R')- or -N(R')-C(X)- in which X = O or S and R' denotes a hydrogen atom or a linear C1-C4 or branched C3-C4 alkyl radical;

[0059] preferably R5 is unsubstituted and / or uninterrupted and / or saturated; more preferably R5 is saturated in C3-C11, even more preferably in C5-C9 such as C7; - R6 represents: • H, • OR7, • a linear or branched, saturated or monovalent Cl-Cl 1 hydrocarbon radical unsaturated, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7, and / or said radical being optionally interrupted by O, NR7, S, CO or their combinations such as (thio)ester or (thio)amide(s) -C(X)-N(R')- or -N(R')-C(X)- in which X = O or S and R' denotes a hydrogen atom or a linear C1-C4 or branched C3-C4 alkyl radical; preferably unsubstituted and / or uninterrupted and / or saturated; more preferably saturated in C3-C11, even more preferably in C5-C9 such as C7;

[0060] preferably R6 represents H, OR7, more preferably OR7 and even more preferably OH; - R7 represents: • H, • a linear C1-C4 or branched C3-C4 alkyl radical,

[0061] preferably R7 represents H; - R8 represents: • H, • a C1-C4 alkyl radical,

[0062] preferably R8 represents H

[0063] or R7 and R8 can form together with the nitrogen atom which carries them a heterocycle of 5 to 8 members, preferably of 5 or 6 members, said heterocycle being optionally substituted by one or more identical or different radicals chosen from a linear C1-C4 or branched C3-C4 alkyl radical and OH;

[0064] or one of its salts, and / or solvates and / or isomers.

[0065] In particular: - RI to R4 are identical or different and represent: • H, • a linear C1-C4 or branched C3-C4 alkyl radical optionally substituted by OH, halogen,

[0066] preferably RI to R4 are identical and represent H; - R5 represents a linear or branched, saturated or unsaturated monovalent Cl-Cl 1 hydrocarbon radical, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7;

[0067] preferably R5 is unsubstituted and / or saturated, more preferably R5 is saturated in C3-C11, even more preferably in C5-C9 such as C7; - R6 represents: • H, • OR7, • a linear or branched, saturated or monovalent Cl-Cl 1 hydrocarbon radical unsaturated, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7; preferably unsubstituted and / or saturated, more preferably saturated in C3-C11, even more preferably in C5-C9 such as C7;

[0068] preferably R6 represents H, OR7, more preferably OR7, even more preferably OH. - R7 represents: • H, • a linear C1-C4 or branched C3-C4 alkyl radical,

[0069] preferably R7 represents H; - R8 represents: • H, • a linear C1-C4 or branched C3-C4 alkyl radical;

[0070] preferably R8 represents H;

[0071] or R7 and R8 can form together with the nitrogen atom which carries them a heterocycle of 5 to 8 members, preferably of 5 or 6 members, said heterocycle being optionally substituted by one or more identical or different radicals chosen from a linear or branched C1-C4 alkyl radical and OH.

[0072] The compounds of formula (I) and its tautomeric form (!') are as follows:

[0073] [Chem.2]

[0074] (I)

[0075] [Chem.2]

[0076] (I')

[0077] Where: - RI to R4 identical or different represent: • H, • a linear C1-C4 or branched C3-C4 alkyl radical optionally substituted by OH or halogen,

[0078] preferably RI to R4 are identical and represent H; - R5 represents a linear or branched, saturated or unsaturated monovalent C1-C11 hydrocarbon radical, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7, and / or said radical being optionally interrupted by O, NR7, S, CO or their combinations such as (thio)ester or (thio)amide(s) -C(X)-N(R')- or -N(R')-C(X)- in which X = O or S and R' denotes a hydrogen atom or a linear C1-C4 or branched C3-C4 alkyl radical; preferably R5 is unsubstituted and / or uninterrupted and / or saturated; more preferably R5 is saturated at C3-C11, even more preferably at C5-C9 such as C7; - R6 represents: • OR7, • a linear or branched, saturated or unsaturated monovalent C1-C11 hydrocarbon radical, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7, and / or said radical being optionally interrupted by O, NR7, S, CO or their combinations such as (thio)ester or (thio)amide(s) -C(X)-N(R')- or -N(R')-C(X)- in which X = O or S and R' denotes a hydrogen atom or a linear C1-C4 or branched C3-C4 alkyl radical; preferably unsubstituted and / or uninterrupted and / or saturated; more preferably saturated in C3-C11, even more preferably in C5-C9 such as C7;

[0079] preferably R6 represents OR7, more preferably OH; - R7 represents: • H, • a linear C1-C4 or branched C3-C4 alkyl radical,

[0080] preferably R7 represents H; - R8 represents: • H, • a linear C1-C4 or branched C3-C4 alkyl radical,

[0081] preferably R8 represents H;

[0082] or R7 and R8 can form together with the nitrogen atom which carries them a heterocycle of 5 to 8 members, preferably of 5 or 6 members, said heterocycle being optionally substituted by one or more identical or different radicals chosen from a C1-C4 alkyl radical and OH;

[0083] or one of its salts, and / or solvates and / or isomers.

[0084] In particular: - RI to R4 are identical or different and represent: • H, • a linear C1-C4 or branched C3-C4 alkyl radical optionally substituted by OH, halogen,

[0085] preferably RI to R4 are identical and represent H; - R5 represents a linear or branched, saturated or unsaturated monovalent Cl-Cl 1 hydrocarbon radical, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7;

[0086] preferably R5 is unsubstituted and / or saturated, more preferably R5 is saturated in C3-C11, even more preferably in C5-C9 such as C7; - R6 represents: • OR7,

[0087] preferably R6 represents OH; - R7 represents: • H, • a linear C1-C4 or branched C3-C4 alkyl radical,

[0088] preferably R7 represents H; - R8 represents: • H, • a linear C1-C4 or branched C3-C4 alkyl radical,

[0089] preferably R8 represents H;

[0090] or R7 and R8 can form together with the nitrogen atom which carries them a heterocycle of 5 to 8 members, preferably of 5 or 6 members, said heterocycle being optionally substituted by one or more identical or different radicals chosen from a linear C1-C4 or branched C3-C4 alkyl radical, OH.

[0091] More particularly, the compounds of formula (II) or its tautomeric form (II') are chosen from compounds 1 to 83 mentioned in table 1 as well as their salts and / or isomers and / or solvates.

[0092] [Tables 1] Compound 31 ¥-y _ / / / Compound w Y V__, H \ y 32 •1 Z4-- / -X. XX xx' '"Yy'' o Compound 3 3 ;; YH Xx. / Y / x X'x« x XQ Aw Compound 34 Compound 35 Q Compound 36 "x,^ j4 H 4> Compound 37 '^Y 6 Compound 38 Compound 39 Compound 40 f 8......- F Com / V-4 X___ / X \ y^x \ .....y Y.,,,,,. Y posed 41 f AF Compound 4 H 2 xx X xx K 'YG ^xX\Xx, .X Compound 43 Compound 44 Compound 45 r-—--Ηf 6 Compound 46 N y Compound 48 Compound 47 A T Compound 49 / / \ P / ., / C-—-- / / \ / f \ Q OH Compound 50 Compound 51 H 0 Compound 52 CF Compound - -'■-x 53 H Compound 54 My* Compound 55 CHC Compound 56 J'c X--V xk .x 11 T ~ ...... T Compound 57 Compound 58 C 2û '' rc Compound 59 CTT^' Compound 60 Compound y 61 c Compound 62 Compound 63 Compound 64 ■%___ / K; \___ / \ / v. / ....." Oooitiie b <?od gcornetry shown Composé 65 Compound 66 V™ / LJy> Compound 68 / \ \ „„ / %_Y G_ \=J \...... \ \ \_____ Compound 67 O "jT""' YY"-' Compound 69 Compound 70 Compound 71 OH L ■ f Compound 74 Compound 72 Compound 73 / / /  / \ / / \ / \ -:0 OH Compound 75 Compound 76 x'sy ii G j........, î f- : ÿ...... fsf JY c "......O.....Y Compound 77 Compound 78 / / Compound 79 ......r .Às. X01'1 x~- -'X -'xx°x X' QJ— | - Uy 0 GH Compound 80 Compound 81 Compound 82

[0093] More preferably, the compounds of formula (II) or (II') are chosen from compounds 1, 2, 3, 4, 16, 18, 26, 29, 30, 31, 37, 50, 67, 75 and 76 as mentioned in Table 1 as well as their salts and / or isomers and / or solvates.

[0094] Even more preferably, the compounds of formula (II) or (II') are chosen from compounds 3, 4, 16, 18, 29, 30, 67, 75 and 76 as mentioned in Table 1 as well as their salts and / or isomers and / or solvates.

[0095] Even more preferably, the compounds of formula (II) or (II') are chosen from compounds 4, 16, 18, 29, 30, 67, 75 and 76 as mentioned in Table 1 as well as their salts and / or isomers and / or solvates.

[0096] More particularly, the compounds of formula (I) or (I') are chosen from compounds 1, 2, 3, 4, 16, 18, 26, 28, 29, 30, 31, 50, 67, 75, 76 mentioned in table 2 as well as their salts and / or isomers and / or solvates and / or tautomers.

[0097] [Tables2] x^ / .............. / X Cï Ot'i Compound 1 DH OH / y* Compound 2 HJ ' x / \ r X^< \-----z \ / Z / -“X OH Compound 3 ,..... / X / \ / \ / / — - Compound 4 / ■ / / H / <•' :>— M / .....' y / \ O OH Compound 16 X / ....... s ç. \ Compound 18 X \ < / rst-i Composé 26 / / “A H / .y------ / \ / / -~X d OH Composé 28 Composé 29 V. / ' / XX / X / \ xx A—N x X\ / \ X \ X____ Composé 30 Composé 31 / ......yz........ / Composé 50 ;-so oh / X___ / \\__ / \___. X X X..... Composé 67 / f— \ / / / X —f\ / —■ X...... / ...... / \ / \ / HO DH Composé 75 ■ Composé 76

[0098] Preferably, the compounds of formula (I) or (!') are chosen from compounds 3, 4, 16, 18, 26, 28, 29, 30, 67 and 75 mentioned in Table 2 as well as their salts and / or isomers and / or solvates.

[0099] More preferably, the compounds of formula (I) or (!') are chosen from compounds 4, 16, 18, 29, 30, 67 and 75 mentioned in table 2 as well as their salts and / or isomers and / or solvates.

[0100] Preferably, the compounds of formula (I) and formula (II) represent 2-heptyl-3-hydroxy-4-quinolone as well as its tautomeric form.

[0101] 2-heptyl-3-hydroxy-4-quinolone has been described since 1959 (Pseudomonas pigments. VII. Isolation of the substance B from the culture of Pseudomonas aeruginosa T 359 I Hakko Kogaku Zasshi (1959), 37, 59-63).

[0102] It has the CAS number 108985-27-9 and has the following structure:

[0103] [Chem.3] / .__ / \ / X / \m / __ / \ / / / \ C OH

[0104] The salts of the compounds of formula (I) or (I') or (II) or (II') are chosen from all cosmetically acceptable salts. By "cosmetically acceptable salt" is meant a salt compatible with the skin, mucous membranes and / or appendages.

[0105] By "solvated" is meant the mixture of a compound of formula (I) or (I') or (II) or (II') with one or more molecules of water or organic solvent.

[0106] By "isomer" is meant in particular the optical isomers or any positional isomer, or any geometric isomer of a compound of formula (I) or (I') or (II) or (ir). Cosmetic composition

[0107] The present invention also relates to a cosmetic composition, in particular for the prevention and / or treatment of the signs of aging, comprising at least one compound of formula (I) or (I'), or one of its salts, and / or solvates and / or isomers, in a physiologically acceptable medium.

[0108] By "physiologically acceptable medium" is meant a medium compatible with keratin materials, in particular the skin. The physiologically acceptable medium is generally adapted to the nature of the support on which the composition is to be applied, as well as to the form in which the composition is to be packaged.

[0109] The physiologically acceptable medium of the composition used is advantageously an aqueous medium.

[0110] It may for example consist of water or a mixture of water and at least one physiologically acceptable organic solvent.

[0111] According to a preferred embodiment, the compositions of the invention comprise at least 20% by weight of water, in particular at least 40% by weight of water relative to to the total weight of said composition.

[0112] Preferably, the composition according to the invention has a water content ranging from 20% to 95% by weight, even better from 40% to 90% by weight relative to the total weight of the composition.

[0113] As organic solvents which can be used in the composition of the invention, mention may be made of organic solvents miscible in water.

[0114] By "water-miscible solvent" according to the present invention is meant a compound which is liquid at room temperature and miscible with water, in particular having a miscibility in water greater than 50% by weight at 25°C and atmospheric pressure.

[0115] As organic solvent, mention may be made, for example, of (C2-C4) alcohols such as ethanol and isopropanol; polyols, in particular those having from 2 to 6 carbon atoms such as glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol; polyol ethers such as 2-butoxyethanol, propylene glycol monomethyl ether, monoethyl ether and diethylene glycol monomethyl ether; and mixtures thereof.

[0116] The water-miscible organic solvent(s) may be present in a concentration of 0.01% to 30% by weight, preferably 0.1% to 20% by weight and more preferably 1% to 10% by weight, relative to the total weight of the composition.

[0117] In particular, the cosmetic composition according to the invention further comprises at least one cosmetic adjuvant.

[0118] Thus, preferably, the composition according to the invention comprising, in a physiologically acceptable medium, at least one compound of formula (I) or (I'), or one of its salts, solvates and / or isomers, may further comprise one or more usual cosmetic adjuvants, in particular chosen from hydrophilic or lipophilic gelling agents, preservatives, cosmetic active agents such as anti-aging active agents other than the compounds of formula (I) or (I') or (II) or (II'), fatty substances such as oils, emulsifiers, antioxidants, vitamins, perfumes, fillers, sunscreens, odor absorbers, desquamating active agents, moisturizing active agents, emollients, and coloring matters, and mixtures thereof.

[0119] The quantities of these different adjuvants are those conventionally used in the fields considered, and for example from 0.01 to 20% of the total weight of the composition. These adjuvants, depending on their nature, can be introduced into the fatty phase or into the aqueous phase. These adjuvants, as well as their concentrations, must be such that they do not harm the advantageous properties of the compound of formula (I) or (I').

[0120] In the context of the present invention, said cosmetic active agents are preferentially chosen from anti-aging cosmetic active agents other than the compounds of formula (I) or (I').

[0121] Preferably, the cosmetic composition has a pH of between 6 and 8, preferably between 6.5 and 7.5, even more preferably around 7.

[0122] Preferably, the composition according to the invention comprises the compound of formula (I), in an amount of between 0.000001% and 10%, preferably between 0.00001% and 5%, and even more preferably between 0.0001% and 1% by weight relative to the total weight of the composition.

[0123] As oils which can be used in the composition of the invention, we can cite for example:

[0124] - hydrocarbon oils of animal origin;

[0125] - hydrocarbon oils of vegetable origin;

[0126] - synthetic esters and ethers, in particular of fatty acids, such as oils of formulas R1COOR2 and R1OR2 in which RI represents the residue of a fatty acid containing from 8 to 29 carbon atoms, and R2 represents a hydrocarbon chain, branched or not, containing from 3 to 30 carbon atoms;

[0127] - linear or branched hydrocarbons, of mineral or synthetic origin;

[0128] - fatty alcohols having from 8 to 26 carbon atoms;

[0129] - partially hydrocarbon and / or silicone fluorinated oils;

[0130] - silicone oils;

[0131] - their mixture s.

[0132] Oil is understood to mean any fatty substance in liquid form at room temperature (20-25°C) and atmospheric pressure. These oils can be of vegetable, mineral or synthetic origin.

[0133] In the list of oils cited above, the term hydrocarbon oil means any oil comprising mainly carbon and hydrogen atoms, and possibly ester, ether, fluorine, carboxylic acid and / or alcohol groups.

[0134] Other fatty substances that may be present in the oily phase are, for example, fatty acids containing 8 to 30 carbon atoms; waxes; silicone resins; and silicone elastomers.

[0135] These fatty substances can be chosen in a variety of ways by those skilled in the art in order to prepare a composition having the desired properties, for example consistency or texture.

[0136] According to a particular embodiment of the invention, the composition used in the context of the invention is a water-in-oil (W / O) or oil-in-water (O / W) emulsion. The proportion of the oily phase of the emulsion can range from 5 to 90% by weight, and preferably from 5 to 60% by weight relative to the total weight of the composition.

[0137] The composition may comprise at least one emulsifier. The emulsions generally contain at least one emulsifier chosen from amphoteric, anionic, cationic or non-ionic emulsifiers, used alone or as a mixture, and optionally a co-emulsifier. The emulsifiers are chosen appropriately according to the emulsion to be obtained (W / O or O / W). The emulsifier and the co-emulsifier are generally present in the composition, in a proportion ranging from 0.3 to 30% by weight, and preferably from 0.5 to 20% by weight relative to the total weight of the composition.

[0138] As coloring matter, we can cite pigments and / or nacres.

[0139] A composition used according to the invention comprises in particular at least one compound of formula (I) or (!') described above and can be presented in all the galenic forms normally used in the cosmetic field.

[0140] It may be in particular in the form of an anhydrous composition, an aqueous, hydroalcoholic, optionally gelled solution, a dispersion of the lotion type, optionally two-phase, an oil-in-water or water-in-oil or multiple emulsion, an aqueous gel, a dispersion of oils in an aqueous phase, in particular using spherules, these spherules being able to be polymeric particles or better, lipid vesicles of ionic and / or non-ionic type, or even in the form of a powder, a serum, a paste or a flexible stick or even a stick. It may be of solid, pasty, or more or less fluid liquid consistency. It may be optionally applied to the skin in the form of an aerosol. It may also be in solid form, and for example in the form of a stick.

[0141] Thus, the composition may comprise all the constituents usually employed in the topical application and administration envisaged.

[0142] A composition according to the invention may advantageously be in the form of an emulsion, in particular obtained by dispersing an aqueous phase in a fatty phase (W / O) or a fatty phase in an aqueous phase (O / W), of liquid or semi-liquid consistency of the milk type, or of soft, semi-solid or solid consistency of the cream or gel type, or even of multiple emulsion (W / O / W or O / W / O). These compositions are prepared according to the usual methods.

[0143] Said compound(s) of formula (I) or (!), or said composition containing them are implemented, within the framework of a use or a method according to the invention, by topical route.

[0144] The compositions according to the invention may be applied directly to the skin or, alternatively, to cosmetic supports of the occlusive or non-occlusive type, intended to be applied locally to the skin. As non-limiting examples of cosmetic supports, mention may in particular be made of a patch, a wipe, a roll-on and a pen.

[0145] The composition may or may not be rinsed off after being applied to the skin.

[0146] Use of compounds of formula (II) or (ID and (I) or (D

[0147] The present invention thus relates to the cosmetic use of at least one compound chosen from the compounds of formula (II) or its tautomeric form (II') or one of their salts, and / or solvates and / or isomers, as an anti-aging active agent.

[0148] The present invention relates in particular to the cosmetic use of at least one compound chosen from the compounds of formula (II) or its tautomeric form (II') or one of their salts, and / or solvates and / or isomers, to improve the cutaneous signs of aging.

[0149] The present invention also relates to the use of a compound of formula (I) or its tautomeric form (I'), or one of their salts, solvates and / or isomers for the care of keratin materials, in particular the skin, more particularly for improving the cutaneous signs of aging and / or as an anti-aging active agent.

[0150] All uses according to the invention are cosmetic, i.e. non-therapeutic.

[0151] By "skin signs of aging" we mean all changes in the external appearance of the skin due to aging.

[0152] The cutaneous signs of aging targeted by the invention may be chosen from an appearance of a microrelief of the skin, a formation and / or a presence of fine wrinkles or fine lines, an appearance of roughness, an alteration of the surface appearance of the skin, an alteration of the radiance of the complexion of the skin, a heterogeneity of the complexion, a loss of elasticity, a loss of suppleness, a loss of firmness, a loss of density, or a loss of tone of the skin, sagging and / or wilting of the skin, a thinning of the horny layer of the skin and a papery appearance of the skin, skin dryness.

[0153] Preferably, the cutaneous signs of aging targeted by the invention are chosen from the appearance of a microrelief of the skin, the formation and / or the presence of fine wrinkles or fine lines, the appearance of roughness, the alteration of the surface appearance of the skin, the thinning of the horny layer of the skin and the papery appearance of the skin, and skin dryness.

[0154] More preferably, the cutaneous signs of aging targeted by the invention are chosen from the appearance of a microrelief of the skin, the formation and / or the presence of fine wrinkles, fine lines, the appearance of roughness, the alteration of the surface appearance of the skin, the thinning of the horny layer of the skin, and skin dryness.

[0155] The skin is in particular the skin of a mammal, preferably human. Preferably, the skin is aged. By "aged skin" is meant a general aesthetic condition of the skin resulting from aging.

[0156] Preferably, the compound(s) of formula (II) or (II') according to the invention is (are) used in an amount of between 0.000001% and 10%, preferably between 0.00001% and 5% and even more preferably between 0.0001% and 1% by weight relative to the total weight of the composition.

[0157] Preferably, the compound(s) of formula (I) or (F) according to the invention is (are) used in an amount of between 0.000001% and 10%, preferably between 0.00001% and 5% and even more preferably between 0.0001% and 1% by weight relative to the total weight of the composition.

[0158] The present invention also relates to a cosmetic skin care treatment method comprising the application to the skin, preferably to skin showing signs of cutaneous aging, of a cosmetic composition comprising, in a physiologically acceptable medium, at least one compound of formula (I) or its tautomeric form (F) or one of their salts, and / or solvates, and / or isomers. Said method therefore comprises at least one step of topical application to the skin of said compound.

[0159] The present invention also relates to a cosmetic skin care treatment method comprising the application to the skin, preferably to skin showing signs of cutaneous aging, of a cosmetic composition comprising, in a physiologically acceptable medium, at least one compound of formula (II) or its tautomeric form (II') or one of their salts, and / or solvates, and / or isomers. Said method therefore comprises at least one step of topical application to the skin of said compound.

[0160] The invention is now illustrated by the following examples. Examples

[0161] The 2-heptyl-3-hydroxy-4-quinolone used is supplied by Sigma-Aldrich, ref 94398, CAS 108985-27-9, purity >96%. Example 1: Epidermal proliferation test Principle:

[0162] The aim of this study is to evaluate the potential of 2-heptyl-3-hydroxy-4-quinolone to modulate the expression of a gene involved in the physiology of normal human epidermal keratinocytes, in particular epidermal renewal such as epidermal proliferation, by quantitative RT-PCR.

[0163] 2-heptyl-3-hydroxy-4-quinolone is estimated at 0.001 g / L in DMSO.

[0164] 2-heptyl-3-hydroxy-4-quinolone is compared to retinoic acid at 10-7 M (i.e. 3.10-5 g / L) in DMSO.

[0165] The most significant marker studied is the epidermal renewal gene HBEGF (Heparin-binding EGF-like growth factor, Gene ID No. 1839). HBEGF is a growth factor that binds to the EGF receptor and stimulates the growth of epithelial cells. It has been shown that the effects of retinoic acid on hyperplasia (in vitro and in vivo) are mediated by an increase in the expression of this factor (Retinoid-Induced Epidermal Hyperplasia Is Mediated by Epidermal Growth Factor Receptor Activation Via Specifies Induction of its Ligands Heparin-Binding EGF and Amphiregulin in Human Skin In Vivo. Rittié L. et al. 2006. Journal of Investigative Dermatology, Vol 126, Issue 4, 732-739). The housekeeping gene GAPDH serves as a normalizing gene for the results. Protocol (experimental conditions): Cytotoxicity

[0166] Normal human keratinocytes were seeded into 96-well plates and cultured for 24 hours in medium dosage. The culture medium was then replaced with culture medium containing or not (control) the test compounds. After 72 hours of incubation, cell viability was measured according to a standard measure of mitochondrial activity using MTT.

[0167] Expression of transcripts in human keratinocytes

[0168] Human epidermal keratinocytes were seeded in a 24-well culture plate and cultured for 72 hours at 37°C and 5% CO2 in culture medium with renewal of the culture medium after the first 24 hours. At the end of the incubation, the culture medium was replaced with assay medium (supplemented with 1.5 mM CaCl2) containing or not (control) the starting material or reference (retinoic acid) and the cells were incubated for another 24 hours.

[0169] All experimental conditions were carried out in n=2. At the end of the treatment, the cells were washed twice in PBS (without CaCl2, without MgCl2) and the extraction of

[0170] RNA was performed using TriPure Isolation Reagent® according to the manufacturer's recommendations. The relative expression of the selected markers was measured by two-step RT-qPCR.

[0171] First, reverse transcription was performed using Transcriptor Reverse Transcriptase (ROCHE) according to the manufacturer's recommendation. Then, PCR experiments were performed using a LightCycler® 480 real-time PCR system by a SYBR®Green incorporation measurement system (Roche). Results and conclusions:

[0172] The results are expressed as modulation factor (Fc, fold change) compared to the untreated control after normalization of the relative expressions compared to the expression of a housekeeping gene (GAPDH). The Fc value of the housekeeping gene GAPDH is therefore equal to 1. The expression of a gene is considered to be stimulated when it is multiplied by at least 1.5.

[0173] Effects of 2-heptyl-3-hydroxy-4-quinolone on the expression of the HBEGE gene involved in the physiology of normal human epidermal keratinocytes. housekeeping gene GAPDH serves as a normalizing gene.

[0174] [Tables 3] Retinoic acid (ref R2625, Sigma, CAS 302-79-4 2-heptyl-3-hydroxy-4-quinolone (ref 94398, Sigma, CAS 108985-27-9) GENE l.00E-07 0.001 M g / L Gene membership gene symbol DMSO DMSO Epidermal renewal HBEGF 2.64 6.52 Housekeeping genes GAPDH 1.01 1.00

[0175] Retinoic acid, tested at 10 7 M (i.e. 3.10-5 g / L), significantly increases (Fc = 2.64) the expression of the HBEGF marker involved in epidermal renewal (Rittié et al. 2006). This result was expected and validates the assay.

[0176] 2-heptyl-3-hydroxy-4-quinolone, tested at 0.001 g / L, also significantly increases (Fc = 6.52) the expression of the HBEGF marker involved in epidermal renewal.

[0177] This result shows that 2-heptvl-3-hvdroxv-4-quinolone is effective in improving epidermal renewal.

[0178] Example 2: Functional test of epidermal renewal in reconstructed model Principle:

[0179] The aim of this study is to evaluate the efficacy of 2-heptyl-3-hydroxy-4-quinolone, under systemic conditions, in stimulating epidermal renewal by modulating the thickness and / or histological quality of a reconstructed 3D model of epidermal tissue between 10 and 14, or 10 and 17 days of maturation.

[0180] 2-heptyl-3-hydroxy-4-quinolone is estimated at 0.03 pg / mL (i.e. 0.00003g / L) in DMSO.

[0181] 2-heptyl-3-hydroxy-4-quinolone is compared to Retinol at 3 pM (i.e. 8.6.10-4 g / L) in DMSO. Protocols (experimental conditions):

[0182] The epidermal thickness evaluation test is carried out to evaluate the effectiveness of the raw materials, in systemic application, on the reconstruction of the epidermis in the 3D in vitro SkinEthic RHE® model for 4 or 7 days. The effects of the active ingredients are determined by an evaluation of the quality of the reconstructed epidermis based on its thickness and morphology. Materials

[0183] - Classic material for biological tests (pipettes, tubes, etc.) - 6-well plates - Optical coherence tomography equipment with Newtone® software (EPISKIN acquisition and EpiSkin RHEV2 processing) - Classic material for histological study (fixing samples, etc.) - 96-well 2 ml Depp plates (if analytical biochemistry tests) Reagents

[0184] - RHE culture medium (SGM) - Retinol DMSO - Formaldehyde - Staining reagent for HE (hematoxylin and eosin) Biological model

[0185] The experiments are carried out on the reconstructed epidermal model SkinEthic RHE®.

[0186] The tissues are received on medium at D10 and stored at 37°C (95% humidity and 5% carbon dioxide) until the end of the treatments at D14 or D17. RH3E TEST METHOD Solubilization

[0187] For compounds solubilized in DMSO, 1000X solutions are first vortexed for 1 minute and stored at room temperature.

[0188] For compounds solubilized in water, 10X solutions are prepared in the same manner in the media.

[0189] The solubility aspect is assessed visually.

[0190] The solutions are then diluted in a medium to obtain the final solution IX and stored at 4°C. Treatment

[0191] Systemic treatments are carried out on D10, D12 and harvest on D14 (Short-term Protocol).

[0192] Tissues are cultured with 2 ml of treatment solution (raw material (RM) in SGM medium) in a 6-well plate and stored at 37°C (95% humidity and 5% carbon dioxide) between treatments.

[0193] For all conditions, the MP (Raw Materials) are tested in triplicate (n = 3).

[0194] For MPs of interest, if no toxicity and good histological quality are observed at D14, it is possible to treat the tissues at D14 with 3mL of treatment solution and harvest at D17 in a long-term protocol. Viability

[0195] No specific viability studies are carried out in this test. Cell viability is monitored during the first treatment by histological analysis which makes it possible to verify the capacity of the tissue to generate good quality epidermis. OCT acquisition and analysis

[0196] OCT (Optical Coherence Tomography) is a non-invasive imaging technique, based on the analysis of infrared light reflected by tissues and the creation of an interference signal.

[0197] OCT allows visualization of surface aspects, the 2D structures of the RHE® model are followed during epidermal reconstruction. This also makes it possible to determine, by acquisition and segmentation with Newtone® algorithms, the epidermal thickness of the tissue after reconstruction.

[0198] Image acquisition and analysis are performed on D10, D12, and D14 under all tested conditions.

[0199] A variation in thickness on the first day of treatment is carried out to observe the evolution of thickness for all tissues.

[0200] In a second step, the thickness variations are rationalized with the vehicle (untreated control or DMSO). Histology

[0201] A histological analysis is carried out on all the conditions tested and on all the tissues to evaluate the impact of the treatment on the quality of the reconstruction.

[0202] The histological process and Hematoxylin and Eosin staining are performed according to the Episkin histology platform protocol.

[0203] Analysis of treatment cytotoxicity and histological qualities is performed and compared to untreated or vehicle conditions.

[0204] INTERPRETATION CRITERIA References

[0205] The test has 3 references to guarantee the good quality of the tissue batch and the good response of the treatments: - Untreated control, as a negative reference, DMSO, as a vehicle without effect, Retinol, a positive reference for tissue quality with an increase in cell proliferation (epidermal thickness) and a reduction in differentiation (histological quality).

[0206] The expected results for these references are: Untreated Control (= Untreated Tissue): good and homogeneous overall quality with an epidermal thickness of up to 80 pm on D10 (or on the first day of treatment), DMSO: good overall quality close to the untreated control without negative impact on the thickness of the epidermis on the day of harvest. Retinol: decreased differentiation compared to the vehicle with improved stratification and epidermal thickness up to 15% compared to to DMSO from variation D10 to D14. Molecules tested

[0207] For each molecule tested, the interpretation criteria are based on: Epidermal thickness, Histological quality at the end of treatment.

[0208] Each condition is compared to the vehicle (untreated control or DMSO control). Raw data (OCT measurements)

[0209] E10 (pm): Epidermal thickness at D10 E14 (pm): Epidermal thickness at D14 Calculations

[0210] VAR (%): Variation in epidermal thickness between D10 and D14

[0211] With VAR (in %) = [(E14 / E10) x 100] - 100

[0212] VAR_normalized (%): Variation in epidermal thickness between D10 and D14, normalized: compared to solvent (DMSO) for Retinol and Indole and compared to Untreated Fabric for Untreated Fabrics and Solvent

[0213] With normalized VAR (%) = VAR (%) - (average of the VARs of the 3 biological replicates (%))

[0214] Considering: biological replicates of DMSO for retinol and 2-heptyl-3-hydroxy-4-quinolone, biological replicates of Untreated Tissue for Untreated Tissue and for Solvent (DMSO).

[0215] Average_VAR_normalized (%): Average of the Variations in the Thickness of the epidermis between D10 and D14, normalized for the 3 biological replicates

[0216] With Average_normalized_VAR (%) = (normalized_VAR replicate 1 + normalized_VAR replicate 2 + normalized_VAR replicate 3) / 3

[0217] EC_ VAR_normalized (%): Standard deviation of the Variations in the Thickness of the epidermis between D10 and D14, normalized for the 3 biological replicates,

[0218] With EC_ VAR_normalized (%) = [(VAR_normalized (%) - Average_VAR_normalized (%)2 / 3] Results and conclusions:

[0219] The results of the untreated tissues and DMSO are expressed as the average variation in the thickness of the epidermis of the reconstructed model tissue, between D10 and D14, normalized compared to the untreated tissues.

[0220] The results for retinol and 2-heptyl-3-hydroxy-4-quinolone are expressed as the mean variation in epidermal thickness of the reconstructed model tissue, between D10 and D14, normalized to the solvent (DMSO).

[0221] These standardized average variations are expressed as a percentage and are considered significant when they are greater than or equal to 10%.

[0222] Variation in the thickness (in pm) of the reconstructed epidermal model between D 10 and D 14. Calculations of the percentages of variation compared to the vehicle. TNT: Untreated tissues

[0223] [Tables4] MP MP Concentration Biological replicate E10 (pm) (1) E14 (pm) (2) VAR (%) (3) VAR_normalized (%) (4) Mean _VAR_normalized (%) (5) EC_ VAR_normalized (%) (6) TNT na 1 84 115 36 4 0 3 2 91 118 30 -3 3 90 118 31 -1 DMSO 0.1% 1 90 117 30 -3 -4 1 2 90 116 28 -4 3 88 113 29 -4 Retino 1 in DMSO 3 pM 1 77 127 66 37 37 3 2 76 129 69 40 3 77 126 64 35 2-hept yl-3-hydroxy-4-quinoline in DMSO 0.03 pg / mL 1 80 112 39 10 10 0 2 83 116 39 10 3 79 109 39 10 3 89.14 121.48 36.27 7.27

[0224] (1) Thickness OCT J10

[0225] (2) Thickness OCT J14

[0226] (3) Thickness variation between J10_J14

[0227] (4) Thickness variation between J10_J14, normalized

[0228] (5) Average for the 3 biological replicates of the thickness variations between J10_J14, normalized

[0229] (6) Standard deviation for the 3 biological replicates of the thickness variations between J10_J14, normalized

[0230] Retinol, tested at 3 pM (i.e. 8.6.10 4 g / L), significantly increases epidermal thickness with a variation greater than 30%. This result was expected and validates the dosage.

[0231] 2-heptvl-3-hvdroxv-4-quinolone, tested at 0.03 ue / mL (i.e. 0.00003 g / L), shows a significant positive effect on epidermal renewal compared to retinol (with 10% more variation compared to the solvent) under the conditions used to carry out this test.

Claims

Claims

1. Cosmetic use of at least one compound of formula (II) or its tautomeric form (II'): [Chem.l] (II) [Chem.l] (he') Or : - RI to R4 identical or different represent: • H, • a linear C1-C4 or branched C3-C4 alkyl radical optionally substituted by OH or halogen; preferably R1 to R4 are identical and represent H; - R5 represents: a linear or branched, saturated or unsaturated monovalent Cl-Cl 1 hydrocarbon radical, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, C00R7, and / or said radical being optionally interrupted by O, NR7, S, CO or their combinations such as (thio)ester or (thio)amide(s) -C(X)-N(R')- or -N(R')-C(X)-in which X = O or S and R' denotes a hydrogen atom or a linear C1-C4 or branched C3-C4 alkyl radical; preferably R5 is unsubstituted and / or uninterrupted and / or saturated; more preferably R5 is saturated at C3-C11, even more preferably at C5-C9 such as C7; - R6 represents: • H, • OR7, • a linear Cl-Cl 1 monovalent hydrocarbon radical or branched, saturated or unsaturated, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7, and / or said radical being optionally interrupted by O, NR7, S, CO or their combinations such as (thio)ester or (thio)amide(s) -C(X)-N(R')- or -N(R')-C(X)-in which X = O or S and R' denotes a hydrogen atom or a linear C1-C4 or branched C3-C4 alkyl radical; preferably unsubstituted and / or uninterrupted and / or saturated; more preferably saturated in C3-C11, even more preferably in C5-C9 such as C7; preferably R6 represents H, OR7, more preferably OR7 and even more preferably OH; - R7 represents: • H, • a linear C1-C4 or branched C3-C4 alkyl radical, preferably R7 represents H; - R8 represents: • H, • a C1-C4 alkyl radical, preferably R8 represents H or R7 and R8 can form together with the nitrogen atom which carries them a heterocycle of 5 to 8 members, preferably of 5 or 6 members, said heterocycle being optionally substituted by one or more identical or different radicals chosen from a linear C1-C4 or branched C3-C4 alkyl radical and OH; or one of its salts, and / or solvates and / or isomers, as an anti-aging active ingredient.

2. Use according to claim 1, in which the compound(s) of formula (II) or its tautomeric form (II') are characterized in that: - RI to R4 are identical or different and represent: • H, • a linear C1-C4 or branched C3-C4 alkyl radical optionally substituted by OH, halogen, preferably R1 to R4 are identical and represent H; - R5 represents a linear or branched, saturated or unsaturated monovalent Cl-Cl 1 hydrocarbon radical, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, C00R7; preferably R5 is unsubstituted and / or saturated, more preferably R5 is saturated in C3-C11, even more preferably in C5-C9 such as C7; - R6 represents: • H, • OR7, • a linear or branched, saturated or unsaturated monovalent C1-C11 hydrocarbon radical, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7; preferably unsubstituted and / or saturated, more preferably saturated in C3-C11, even more preferably in C5-C9 such as C7; preferably R6 represents H, OR7, more preferably OR7, even more preferably OH; - R7 represents: • H, • a linear C1-C4 or branched C3-C4 alkyl radical, preferably R7 represents H; - R8 represents: H, a linear C1-C4 or branched C3-C4 alkyl radical;

3. preferably R8 represents H or R7 and R8 can form together with the nitrogen atom which carries them a heterocycle of 5 to 8 members, preferably of 5 or 6 members, said heterocycle being optionally substituted by one or more identical or different radicals chosen from a linear or branched C1-C4 alkyl radical in C3-C4 and OH. Use according to any one of the preceding claims, in which the compound(s) of formula (II) or its tautomeric form (II') are chosen from compounds 1 to 83 mentioned in [Table 1]: Compound 1 Compound 2 Compound 3 t----- r" X|T " ''Yx --\ / ' —\ t~-\ OH Compound 6 Compound 4 Compound 5 / \ ......

4. >--4 ..N x / X. .....« \ / \ / [ f F OH Compound 7 OH Compound 9 Compound 8 'yyv ' --x' F i I! j ' ÔH ÔH Compound 12 Compound 10 Compound 11 1 JXZ^h 'Y JlX kJU OH Compound 14 OH Compound 13 Compound 15 y yy \ y HO" "y / \ -X / ZA / / Compound 16 Compound 17 Compound 18 Compound 19 f Compound 20 \ / .....4......'7 7 \ / \__ Compound \\ ___£ X____ \ fl \ fl / - yv / / 0' 21 T ' T Compound 22 Compound 23 Compound 24 VX" Compound 25 __— / 7 î-l 7 <7 -----K / -----' \ / 'x / \ / / . / \ . D GH Compound 26 Compound 27 J ......z \ / 7 Oz OH Compound 28 Gu Compound 29 U / —< / X . 7 \ \X \ Compound 30 x>-k ,.NH Compound 31 X / "\ ( X / / C lom] K )osé 33 Compound 32 Compound 34 C *4 <x Gçr ....... omposé 35 C loin] k ! )osé 36 CCT........' ! Compound 37 ..CT''""''........ Compound 39 î II T Compound 38 Compound 40 C .....J...... / V-.g ; V / X \,,,,,,X' X....... <7 Compound 41 vCÛ......... X § Compound 42 \ Te T " , x TT Compound 43 C X'^T Compound 44 F CC X.. xX X---X -X x- ' IA J ô Compound 45 ClT^ >5 CnîTinnsé 46 | P Compound 48 C ü Compound 47 var^ Compound 49 XA ., / ZA—,— / '\___Z \ \ / / g' oh Compound 50 X. A xx XX G x [ ir XXX f Compound 51 HH OQt^ II Compound 52 Compound 53 Compound 54 Comp 0 3sé 55 CM -M-, CÇ Compound 56 Comp 57 6 Compound 58 C 0 comp )sé 59 OX™ Compound 60 Compound 61 C ........ Compound 62 "T Compound 63 Comp )sé 64 % r— / \ x\ / ""h Doûtîl» bond geometry 5ha Compound 65 \ CÇ Comp 3sé 66 HÛ GH \ / / \ / y_ / \_, \...... Compound 67 C •Xr....."....... Compound 68 Compound 69 Comp )sé 70 Compound 71 OH Compound 7 2 C omposc i 73 ( Zon iposé 74 ( À » 4--< '>--s Compound 75 c .omposc 76 C "" y omposc 77 c .....“.....~ .omposc 78 f— Con ------ / 4------N w / / w \ / \ iposé 79 C omposc 8 0 c û .omposc -•X .-OH I ' T 5 81 ( Compound 82

4.

5.

6. as well as their salts and / or isomers and / or solvates, in particular among compounds 1, 2, 3, 4, 16, 18, 26, 29, 30, 31, 37, 50, 67, 75 and 76 as well as their salts and / or isomers and / or solvates, preferentially among compounds 3, 4, 16, 18, 29, 30, 67, 75 and 76 as well as their salts and / or isomers and / or solvates, even more preferentially among compounds 4, 16, 18, 29, 30, 67, 75 and 76 as well as their salts and / or isomers and / or solvates. Use according to any one of the preceding claims, wherein the compound of formula (II) is 2-heptyl-3-hydroxy-4-quinolone or its tautomeric form. Use according to any one of the preceding claims, for improving the cutaneous signs of aging. Use according to any one of the preceding claims, for preventing and / or reducing at least one chosen cutaneous sign of aging. among the appearance of a microrelief of the skin, the formation and / or presence of fine wrinkles or fine lines, the appearance of roughness, an alteration of the surface appearance of the skin, an alteration of the radiance of the skin tone, a heterogeneity of the complexion, a loss of elasticity, a loss of suppleness, a loss of firmness, a loss of density, or a loss of skin tone, sagging and / or wilting of the skin, a thinning of the horny layer of the skin and a papery appearance of the skin, skin dryness.

7. Use according to any one of the preceding claims, in in which the compound(s) of formula (II) or its tautomeric form (II') or one of its salts, solvates and / or isomers, are used in an amount of between 0.000001% and 10%, preferably between 0.00001% and 5% and even more preferably between 0.0001% and 1% by weight relative to the total weight of the composition.

8. Cosmetic composition, in particular for the prevention and / or treatment of the signs of aging, comprising in a physiologically acceptable medium, at least one compound of formula (I) or its tautomeric form (I'): [Chem. 2] (I) [Chem. 2] (D Or : - RI to R4 identical or different represent: • H, • a linear C1-C4 or branched C3-C4 alkyl radical optionally substituted by OH or halogen, preferably R1 to R4 are identical and represent H; - R5 represents a linear or branched, saturated or unsaturated monovalent C1-C11 hydrocarbon radical, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7, and / or said radical being optionally interrupted by O, NR7, S, CO or their combinations such as (thio)ester or (thio)amide(s) -C(X)-N(R')- or -N(R')-C(X)- in which X = O or S and R' denotes a hydrogen atom or a linear C1-C4 or branched C3-C4 alkyl radical; preferably R5 is unsubstituted and / or uninterrupted and / or saturated; more preferably R5 is saturated at C3-C11, even more preferably at C5-C9 such as C7; - R6 represents: • OR7, • a linear Cl-Cl 1 monovalent hydrocarbon radical or branched, saturated or unsaturated, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7, and / or said radical being optionally interrupted by O, NR7, S, CO or their combinations such as (thio)ester or (thio)amide(s) -C(X)-N(R')- or -N(R')-C(X)-in which X = O or S and R' denotes a hydrogen atom or a linear C1-C4 or branched C3-C4 alkyl radical; preferably unsubstituted and / or uninterrupted and / or saturated; more preferably saturated in C3-C11, even more preferably in C5-C9 such as C7; preferably R6 represents OR7, more preferably OH; - R7 represents: • H, • a linear C1-C4 or branched C3-C4 alkyl radical, preferably R7 represents H; - R8 represents: • H, • a linear C1-C4 or branched C3-C4 alkyl radical, preferably R8 represents H; or R7 and R8 can form together with the nitrogen atom which carries them a heterocycle of 5 to 8 members, preferably of 5 or 6 members, said heterocycle being optionally substituted by one or more identical or different radicals chosen from a C1-C4 alkyl radical and OH; or one of its salts, and / or solvates and / or isomers.

9. Cosmetic composition according to claim 8, in which the compound(s) of formula (I) or its tautomeric form (!') are characterized in that: - RI to R4 are identical or different and represent: • H, • a linear C1-C4 or branched C3-C4 alkyl radical optionally substituted by OH, halogen, preferably R1 to R4 are identical and represent H; - R5 represents a linear or branched, saturated or unsaturated monovalent Cl-Cl 1 hydrocarbon radical, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, COOR7; preferably R5 is unsubstituted and / or saturated, more preferably R5 is saturated in C3-C11, even more preferably in C5-C9 such as C7; - R6 represents: • OR7, preferably R6 represents OH; - R7 represents: • H, • a linear C1-C4 or branched C3-C4 alkyl radical, preferably R7 represents H; - R8 represents: H, a linear C1-C4 or branched C3-C4 alkyl radical, preferably R8 represents H; or R7 and R8 can form together with the nitrogen atom which carries them a heterocycle of 5 to 8 members, preferably of 5 or 6 members, said heterocycle being optionally substituted by one or more identical or different radicals chosen from a linear C1-C4 or branched C3-C4 alkyl radical, OH.

10. Cosmetic composition according to any one of claims 8 to 9, in which the compound(s) of formula (I) or its tautomeric form (!') are chosen from compounds 1, 2, 3, 4, 16, 18, 26, 28, 29, 30, 31, 50, 67, 75, 76 mentioned in [Table 2]: / / \ yy—H ,— VV _ / \_ 0 'b'H '''Y Compound 2 / / . / ___f W £ . / __ / G'' OH Compound 3 Compound 1 À \ U / / / \ / ■ V--. y.....J ..... / VA \_J \...... / \..... / Compound 4 / / \ Ô CH Compound 16 Compound 18 / I TT - y r-1 / \.....a ....... / X / / OH lr Compound 26 Compound 28 Compound 29 H. Xa ,................ \ \ / V„ / ” \ J- .NA \ ■—AC ï y \___ X \ Compound 30 Compound 31 Compound 50 / OH A ............. .... r: i (}..... / / X..... <a        ...... w         a      ff     \     \____ \ v — u composé 67 75 76

11.

12.

13. as well as their salts and / or isomers and / or solvates and / or tautomers, preferably among compounds 3, 4, 16, 18, 26, 28, 29, 30, 67 and 75 as well as their salts and / or isomers and / or solvates, more preferably among compounds 4, 16, 18, 29, 30, 67 and 75 as well as their salts and / or isomers and / or solvates. Cosmetic composition according to any one of claims 8 to 10, in which the compound of formula (I) is 2-heptyl-3-hydroxy-4-quinolone or its tautomeric form. Cosmetic composition according to any one of claims 8 to 11, further comprising at least one cosmetic adjuvant. Cosmetic composition according to claim 12, in which said at least one cosmetic adjuvant is chosen from hy- gelling agents drophiles or lipophilic, preservatives, cosmetic active ingredients such as anti-aging active ingredients other than the compounds of formula (I) or (!') or (II) or (II'), fatty substances such as oils, emulsifiers, antioxidants, vitamins, perfumes, fillers, sunscreens, odor absorbers, desquamating active ingredients, moisturizing active ingredients, emollients, and coloring matters, and mixtures thereof.

14. Composition according to any one of claims 8 to 13, which has a pH of between 6 and 8, preferably between 6.5 and 7.5, more preferably around 7.

15. Use of at least one compound of formula (I) or its tautomeric form (I'), or one of its salts, solvates and / or isomers, as defined in any one of claims 8 to 11, for the care of keratin materials, in particular the skin.

16. Cosmetic skin care treatment process comprising the application to skin showing signs of cutaneous aging of a cosmetic composition comprising, in a physiologically acceptable medium, at least one compound of formula (II) or its tautomeric form (II') or one of their salts, and / or solvates, and / or isomers, as defined in any one of claims 1 to 4.

17. A cosmetic skin care treatment process comprising the application to the skin, preferably to skin showing signs of cutaneous aging, of a cosmetic composition comprising, in a physiologically acceptable medium, at least one compound of formula (I) or its tautomeric form (I') or one of their salts, and / or solvates, and / or isomers, as defined in any one of claims 8 to 11.