Compounds from the quinolone family and their uses in cosmetics

Abstract

Quinolone Compounds 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 keratinous materials, particularly 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, to improve the skin's signs of aging, and in particular as an anti-aging active ingredient. It also relates to a cosmetic composition comprising 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: Quinolone family compounds 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 solvated and / or isomers, for the care of keratinous materials, in particular 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, solvated and / or isomers, to improve the skin signs of aging, and in particular as an anti-aging active ingredient.

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

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

[0004] Alterations associated with skin aging can manifest themselves in various ways, including:

[0005] - a microrelief characterized in particular by the appearance of fine wrinkles or lines, or also by the presence of visible pores in high 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, and tone of the skin, a sagging and / or wilting of the skin;

[0008] - a slowing of epidermal renewal leading to a thinning of the stratum corneum of the skin and a papery appearance of the skin;

[0009] - and skin dryness resulting from a decrease in the barrier function of the stratum corneum of the skin.

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

[0011] However, the use of retinol may be limited by its instability, its sensitivity to oxidation, light, 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 on the signs of skin aging, stable and easier to formulate.

[0013] The present invention addresses 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 compounds of formula (II) or its tautomeric form (II'):

[0015] [Chem.l]

[0016] (II)

[0017] [Chem.l]

[0018] (II')

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

[0020] preferably RI to R4 are identical and represent H; - R5 represents: • a monovalent hydrocarbon radical in Cl-Cl 1 linear or branched, saturated or unsaturated, said radical being optionally substituted by at least one radical selected 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 C3-C4 branched 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 monovalent hydrocarbon radical in Cl-Cl 1 linear or branched, saturated or unsaturated, said radical being optionally substituted by at least one radical selected 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 C3-C4 branched 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, • an alkyl radical in Cl-C4,

[0024] preferably R8 represents H

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

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

[0027] as an anti-aging active ingredient.

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

[0029] The present invention also relates to a cosmetic skin care treatment method comprising the application to skin showing cutaneous signs of 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 solvated, and / or isomers.

[0030] The present invention also relates to a cosmetic composition, in particular for the prevention and / or treatment of 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, whether identical or different, represent: • H, • a linear alkyl radical in the C1-C4 range or branched in the C3-C4 range, possibly substituted by OH or a halogen,

[0036] preferably RI to R4 are identical and represent H; - R5 represents a monovalent hydrocarbon radical in linear Cl-Cl 1 or branched, saturated or unsaturated, said radical being optionally substituted by at least one radical selected 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 C3-C4 branched alkyl radical; 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: OR7, a monovalent Cl-Cl1 hydrocarbon radical, linear or branched, saturated or unsaturated, said radical optionally being substituted by at least one radical selected from OR7, SR7, NR7R8, COOR7, and / or said radical optionally being 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 alkyl radical in the C1-C4 range or a branched alkyl radical in the C3-C4 range,

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

[0039] preferably R8 represents H;

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

[0041] or one of its salts, and / or solvated 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, solvated and / or isomers for the care of keratinous materials, in particular the skin, more particularly to improve 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 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] The term “keratinous 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" we mean the entire skin of the body and the scalp of a human being and preferably the skin of the face, décolletage, neck, arms and forearms, hands or even more preferably the skin of the face (in particular the forehead, nose, cheeks, lips, chin), décolletage and neck.

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

[0047] For the purposes of this invention, "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 p-toluenesulfonate (i.e., 1,1'-methylene-bis-(2-hydroxy-3-naphthoate).

[0050] Examples of base 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 hydroxysubstituted mono-, di-, or tri-alkylamines; dicyclohexylamines; tributylamines; pyridine; N-methyl-N-ethylamine; diethylamine; triethylamine; mono-, bis-, or tris-(2-hydroxyalkylamines) 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 compound salt 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, whether identical or different, represent: • H, • a linear C1-C4 or branched C3-C4 alkyl radical possibly substituted by OH or halogen;

[0058] preferably RI to R4 are identical and represent H; - R5 represents: • a monovalent Cl-Cl1 hydrocarbon radical, linear or branched, saturated or unsaturated, said radical optionally being substituted by at least one radical selected from OR7, SR7, NR7R8, COOR7, and / or said radical optionally being interrupted by O, NR7, S, CO or combinations thereof 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 atony or a linear C1-C4 or C3-C4 branched 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 monovalent hydrocarbon radical in Cl-Cl 1 linear or branched, saturated or unsaturated, said radical being optionally substituted by at least one radical selected 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 C3-C4 branched 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, • an alkyl radical in Cl-C4,

[0062] preferably R8 represents H

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

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

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

[0066] preferably RI to R4 are identical and represent H; - R5 represents a monovalent hydrocarbon radical in linear or branched Cl-Cl 1, saturated or unsaturated, said radical possibly being 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 monovalent hydrocarbon radical in Cl-Cl 1 linear or branched, saturated or unsaturated, said radical being possibly 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 together with the nitrogen atom which bears them form a heterocycle of 5 to 8 links, preferably of 5 or 6 links, said heterocycle being optionally substituted by one or more identical or different radicals chosen from a linear C1-C4 alkyl radical or a C3-C4 branched 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, whether identical or different, represent: • H, • a linear alkyl radical in the C1-C4 range or branched in the C3-C4 range, possibly substituted by OH or a halogen,

[0078] preferably RI to R4 are identical and represent H; - R5 represents a monovalent Cl-Cl1 hydrocarbon radical, linear or branched, saturated or unsaturated, said radical being optionally substituted by at least one radical selected 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 in C3-C11, even more preferably in C5-C9 such as C7; - R6 represents: • OR7, • a monovalent Cl-Cl1 hydrocarbon radical, linear or branched, saturated or unsaturated, said radical being optionally substituted by at least one radical selected 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 together with the nitrogen atom which bears them a heterocycle of 5 to 8 links, preferably of 5 or 6 links, said heterocycle being optionally substituted by one or more identical or different radicals chosen from a C1-C4 and OH alkyl radical;

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

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

[0085] preferably RI to R4 are identical and represent H; - R5 represents a monovalent hydrocarbon radical in linear or branched Cl-Cl 1, saturated or unsaturated, said radical possibly being 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 together with the nitrogen atom which bears them form a heterocycle of 5 to 8 links, preferably of 5 or 6 links, said heterocycle being optionally substituted by one or more identical or different radicals chosen from a linear alkyl radical in C1-C4 or branched in C3-C4, 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, compounds of formula (II) or (II') are chosen from the compounds 1, 2, 3, 4, 16, 18, 26, 29, 30, 31, 37, 50, 67, 75 and 76 as mentioned in Table 1 and 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 and their salts and / or isomers and / or solvates.

[0096] More particularly, the compounds of formula (I) or (I') are chosen from the 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 the 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 and 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 and 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 bears 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 hair.

[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 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 signs of aging, comprising at least one compound of formula (I) or (I'), or one of its salts, and / or solvated and / or isomers, in a physiologically acceptable medium.

[0108] By "physiologically acceptable medium" is meant a medium compatible with keratinous materials, in particular skin. The physiologically acceptable medium is generally adapted to the nature of the substrate 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 for 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] Examples of usable organic solvents in the composition of the invention include water-miscible organic solvents.

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

[0115] Examples of organic solvents include (C2-C4) alcohols such as ethanol and isopropanol; polyols, especially those with 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, diethylene glycol monoethyl ether and 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, solvated and / or isomers, may further comprise one or more common cosmetic adjuvants, in particular chosen from hydrophilic or lipophilic gelling agents, preservatives, cosmetic actives such as anti-aging actives different from compounds of formula (I) or (I') or (II) or (II'), fatty substances such as oils, emulsifiers, antioxidants, vitamins, perfumes, fillers, sunscreens, odor absorbers, desquamating actives, moisturizing actives, emollients, and coloring materials, and mixtures thereof.

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

[0120] Within the framework of the present invention, said cosmetic actives are preferably chosen from among the anti-aging cosmetic actives different from the compounds of formula (I) or (I').

[0121] Preferably, the cosmetic composition has a pH 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 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] Examples of oils that can be used in the composition of the invention include:

[0124] - hydrocarbon oils of animal origin;

[0125] - hydrocarbon oils of vegetable origin;

[0126] - synthetic esters and ethers, particularly of fatty acids, such as oils of formulas R1COOR2 and R1OR2 in which RI represents the remainder of a fatty acid containing 8 to 29 carbon atoms, and R2 represents a hydrocarbon chain, branched or unbranched, containing 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.

[0132] The term "oil" refers to any fatty substance in liquid form at ambient temperature (20-25°C) and atmospheric pressure. These oils may be of vegetable, mineral, or synthetic origin.

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

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

[0135] These fats can be chosen in a variety of ways by a person skilled in the art in order to prepare a composition having the desired properties, for example of 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 oil 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 include at least one emulsifier. Emulsions generally contain at least one emulsifier selected from amphoteric, anionic, cationic, or nonionic emulsifiers, used alone or in mixtures, and A co-emulsifier may be used. Emulsifiers are chosen appropriately depending on the emulsion to be obtained (W / O or W / O). The emulsifier and 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 colouring material, we can mention pigments and / or nacres.

[0139] A composition used according to the invention includes in particular at least one compound of formula (I) or (!') described above and can be 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 or hydroalcoholic solution, possibly gelled, a lotion-type dispersion, possibly two-phase, an oil-in-water or water-in-oil or multiple emulsion, an aqueous gel, a dispersion of oils in an aqueous phase, particularly using spherules, these spherules being polymeric particles or, preferably, ionic and / or non-ionic lipid vesicles, or in the form of a powder, a serum, a paste, a flexible rod, or a stick. It may be of solid, pasty, or more or less fluid consistency. It may optionally be applied to the skin in the form of an aerosol. It may also be in solid form, for example, in the form of a stick.

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

[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 an oily phase (W / O) or an oily phase in an aqueous phase (W / O), of liquid or semi-liquid consistency such as milk, or of soft, semi-solid or solid consistency such as cream or gel, or even as a multiple emulsion (W / O / O or W / O / O). These compositions are prepared according to conventional methods.

[0143] Said compound(s) of formula (I) or (!'), or said composition containing them are implemented, in the context of a use or process according to the invention, by topical application.

[0144] The compositions according to the invention may be applied directly to the skin or, alternatively, to occlusive or non-occlusive cosmetic carriers intended for localized application to the skin. Examples of such carriers, which are not limited to a patch, a wipe, a roll-on, and a pen, include but are not limited to patches, wipes, roll-ons, and pens.

[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 compounds of formula (II) or its tautomeric form (II') or one of their salts, and / or solvated and / or isomers, as an anti-aging active ingredient.

[0148] The present invention relates in particular to the cosmetic use of at least one compound chosen from compounds of formula (II) or its tautomeric form (II') or one of their salts, and / or solvated and / or isomers, to improve the skin 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, solvated and / or isomers for the care of keratinous materials, in particular the skin, more particularly to improve the cutaneous signs of aging and / or as an anti-aging active ingredient.

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

[0151] By "cutaneous signs of aging" is meant all changes in the external appearance of the skin due to aging.

[0152] The cutaneous signs of aging referred to in the invention can be chosen from among the appearance of a microrelief of the skin, the formation and / or presence of fine wrinkles or 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, a sagging and / or wilting of the skin, a thinning of the stratum corneum of the skin and a papery appearance of the skin, and dry skin.

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

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

[0155] 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 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 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 skincare treatment method comprising applying to the skin, preferably to skin showing signs of aging, 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. The 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 applying to the skin, preferably to skin showing signs of aging, 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. The 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 evaluated 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. The effects of retinoic acid on hyperplasia (in vitro and in vivo) have been shown to be 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 gene for normalizing the results. Protocol (experimental conditions): Cytotoxicity

[0166] Normal human keratinocytes were seeded in 96-well plates and cultured for 24 hours in average dosage. The culture medium was then replaced with culture medium containing or not (control) the compounds being tested. After 72 hours of incubation, cell viability was measured using a standard measure of mitochondrial activity with the 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 the culture medium being changed after the first 24 hours. At the end of the incubation period, the culture medium was replaced with assay medium (supplemented with 1.5 mM CaC12) containing or not (control) the raw material or reference (retinoic acid), and 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 CaC12, without MgC12) and the extraction of

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

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

[0172] The results are expressed as a modulation factor (Fc, fold change) relative to the untreated control after normalization of relative expressions with respect to the expression of a housekeeping gene (GAPDH). The Fc value of the GAPDH housekeeping gene is therefore equal to 1. Gene expression is considered 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. The The GAPDH housekeeping gene serves as a normalization gene.

[0174] [Table 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 belonging Gene symbol DMSO DMSO Epidermal renewal HBEGF 2.64 6.52 Housekeeping genes GAPDH 1.01 1.00

[0175] Retinoic acid, tested at 10⁷ M (i.e., 3 x 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 a 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 evaluated at 0.03 pg / mL (i.e., 0.00003 g / L) in DMSO.

[0181] 2-Heptyl-3-hydroxy-4-quinolone is compared to Retinol at 3 pM (i.e., 8.6 x 10⁻⁴ g / L) in the DMSO. Protocols (experimental conditions):

[0182] The epidermal thickness assessment test is performed to evaluate the efficacy of the raw materials, applied systemically, on the reconstruction of the epidermis in the SkinEthic RHE® 3D in vitro model over 4 or 7 days. The effects of the active ingredients are determined by an assessment of the quality of the reconstructed epidermis based on its thickness and morphology. Materials

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

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

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

[0186] Tissues are received on medium at J10 and stored at 37°C (95% humidity and 5% carbon dioxide) until the end of treatments at J14 or J17. RH3E TESTING METHOD Solubilization

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

[0188] For compounds solubilized in water, the 10X solutions are prepared in the same way 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 J10, J12 and harvesting on J14 (Short term protocol).

[0192] Tissues are cultured with 2 ml of treatment solution (raw material (RM) in an 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 the MP 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 to harvest at D17 in a long-term protocol. Viability

[0195] No specific viability study is performed in this test. Cell viability is monitored during the first treatment by histological analysis, which verifies the tissue's ability to generate a 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 on the creation of an interference signal.

[0197] OCT allows visualization of surface features; the 2D structures of the RHE® model are tracked during epidermal reconstruction. This also allows determination, through acquisition and segmentation with Newtone® algorithms, of the epidermal tissue thickness after reconstruction.

[0198] Image acquisition and analysis are performed on J10, J12, and J14 under all tested conditions.

[0199] A thickness variation is performed on the first day of treatment 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 performed on all tested conditions and on all tissues to evaluate the impact of the treatment on the quality of the reconstruction.

[0202] The histological process and Hematoxylin and eosin staining are carried out in accordance with the Episkin histology platform protocol.

[0203] The cytotoxicity analysis of the treatment and histological qualities is carried out and compared to the 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 correct response of the treatments: - The 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 overall and homogeneous quality with an epidermal thickness of up to 80 µm at day 10 (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: a decrease in differentiation from the vehicle with improved stratification and epidermal thickness up to 15% compared to to the DMSO of the variation J10 to J14. 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 day 10 E14 (pm): Epidermal thickness at day 14 Calculations

[0210] VAR (%): Variation in Epidermal Thickness between Day 10 and Day 14

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

[0212] Normalized VAR (%): Variation in epidermal thickness between days 10 and 14, normalized: compared to the solvent (DMSO) for Retinol and Indole and in relation to untreated fabric, for untreated fabrics and solvent

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

[0214] Considering: biological replicates of DMSO for retinol and 2-heptyl-3-hydroxy-4-quinolone, biological replicas of untreated tissue for untreated tissues and for solvent (DMSO).

[0215] Normalized_VAR_mean (%): Mean of the Variations in Epidermal Thickness between Day 10 and Day 14, normalized from the 3 biological replicates

[0216] With Average_Normalized_VAR (%) = (Normalized_VAR replica 1 + Normalized_VAR replica 2 + Normalized_VAR replica 3) / 3

[0217] EC_ VAR_normalized (%): Standard deviation of the variations in epidermal thickness between days 10 and 14, 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 untreated tissues and DMSO are expressed as the mean variation in the thickness of the epidermis of the reconstructed model tissue, between J10 and J14, normalized with respect to untreated tissues.

[0220] The results of retinol and 2-heptyl-3-hydroxy-4-quinolone are expressed as the mean change in the thickness of the epidermis of the reconstructed model tissue, between J10 and J14, normalized with respect to the solvent (DMSO).

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

[0222] Variation in thickness (in µm) of the reconstructed epidermal model between days 10 and 14. Calculations of percentage variation relative to the vehicle. TNT: Untreated tissues

[0223] [Tables4] MP Concentration MP Biological Replica E10 (pm) (1) E14 (pm) (2) VAR (%) (3) Normalized VAR (%) (4) Mean Normalized VAR (%) (5) EC Normalized VAR (%) (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-heptyl-3-hydroxy-4-quinolone 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 x 10⁴ g / L), significantly increases epidermal thickness with a variation greater than 30%. This result was expected and validates the assay.

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

Claims

Demands

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, whether identical or different, represent: • H, • a linear Cl-C4 or C3-C4 branched alkyl radical possibly substituted by OH or halogen; preferably RI to R4 are identical and represent H; - R5 represents: a monovalent hydrocarbon radical in Cl-Cl 1 linear or branched, saturated or unsaturated, said radical being optionally substituted by at least one radical chosen from OR7, SR7, NR7R8, C00R7, and / or said radical possibly being 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 C3-C4 branched 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 monovalent hydrocarbon radical in linear Cl-Cl 1 or branched, saturated or unsaturated, said radical being optionally substituted by at least one radical selected 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 C3-C4 branched 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 alkyl radical in the C1-C4 range or a branched alkyl radical in the C3-C4 range, preferably R7 represents H; - R8 represents: • H, • an alkyl radical in Cl-C4, preferably R8 represents H or R7 and R8 can together with the nitrogen atom which bears them form a heterocycle of 5 to 8 links, preferably of 5 or 6 links, said heterocycle being possibly substituted by one or more identical or different radicals chosen from a linear alkyl radical in C1-C4 or branched in C3-C4 and OH; or one of its salts, and / or solvated and / or isomers, as an anti-aging active ingredient.

2. Use according to claim 1, wherein 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 Cl-C4 or C3-C4 branched alkyl radical possibly substituted by OH, halogen, preferably RI to R4 are identical and represent H; - R5 represents a monovalent hydrocarbon radical in linear or branched Cl-Cl 1, saturated or unsaturated, said radical possibly being 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 monovalent Cl-Cl1 hydrocarbon radical linear or branched, saturated or 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; preferably R6 represents H, OR7, more preferably OR7, even more preferably OH; - R7 represents: • H, • a linear alkyl radical in the C1-C4 range or a branched alkyl radical in the C3-C4 range, preferably R7 represents H; - R8 represents: H, a linear alkyl radical in C1-C4 or branched in C3-C4;

3. preferably R8 represents H or R7 and R8 can together with the nitrogen atom which bears them form a heterocycle of 5 to 8 links, preferably of 5 or 6 links, said heterocycle being possibly substituted by one or more identical or different radicals chosen from a linear C1-C4 alkyl radical or a C3-C4 branched alkyl radical and OH. Use according to any one of the preceding claims, wherein the compound(s) of formula (II) or its tautomeric form (II') are selected 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 Compound 0 3se 55 CM -M-, CÇ Compound 56 C lompse 57 6 Compound 58 C 0 lompc )se 59 OX™ Compound 60 Compound 61 C ........ Compound 62 "T Compound 63 C lompc )se 64 % r— / \ x\ / ""h Doûtîl» bond geometry 5ha Compound 65 \ CÇ Compound 3se 66 HÛ GH \ / / \ / y_ / \_, \...... Compound 67 C •Xr....."....... Compound 68 Compound 69 C lompc )se 70 Compound 71 OH Compound 7 2 C composc i 73 ( Zon iposé 74 ( À » 4--< '>--s Compound 75 c .compound 76 C "" y composc 77 c .....“.....~ .compound 78 f— Con ------ / 4------N w / / w \ / \ iposé 79 C composc 8 0 c û .composc -•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, preferably 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 preferably 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 of the preceding claims, to improve the skin signs of aging. Use according to any one of the preceding claims, to prevent and / or reduce at least one skin sign of aging chosen among the appearance of microrelief of the skin, the formation and / or presence of fine wrinkles or lines, the appearance of roughness, an alteration in the surface appearance of the skin, an alteration in the radiance of the skin tone, an unevenness 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 stratum corneum 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, solvated and / or isomers, are used in an amount 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, particularly 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, whether identical or different, represent: • H, • a linear Cl-C4 or branched C3-C4 alkyl radical, possibly substituted by OH or a halogen, preferably RI to R4 are identical and represent H; - R5 represents a monovalent Cl-Cl1 hydrocarbon radical, linear or branched, saturated or unsaturated, said radical being optionally substituted by at least one radical selected 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 in C3-C11, even more preferably in C5-C9 such as C7; - R6 represents: • OR7, • a monovalent hydrocarbon radical in linear Cl-Cl 1 or branched, saturated or unsaturated, said radical being optionally substituted by at least one radical selected 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 C3-C4 branched 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 alkyl radical in the C1-C4 range or a branched alkyl radical in the C3-C4 range, preferably R7 represents H; - R8 represents: • H, • a linear alkyl radical in the C1-C4 range or a branched alkyl radical in the C3-C4 range, preferably R8 represents H; or R7 and R8 can together with the nitrogen atom which bears them form a heterocycle of 5 to 8 links, preferably of 5 or 6 links, said heterocycle being possibly substituted by one or more identical or different radicals chosen from an alkyl radical in C1-C4 and OH; or one of its salts, and / or solvated and / or isomers.

9. Cosmetic composition according to claim 8, wherein 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 Cl-C4 or C3-C4 branched alkyl radical possibly substituted by OH, halogen, preferably RI to R4 are identical and represent H; - R5 represents a monovalent hydrocarbon radical in linear or branched Cl-Cl 1, saturated or unsaturated, said radical possibly being 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 alkyl radical in the C1-C4 range or a branched alkyl radical in the C3-C4 range, preferably R7 represents H; - R8 represents: H, a linear alkyl radical in the C1-C4 range or a branched alkyl radical in the C3-C4 range, preferably R8 represents H; or R7 and R8 can together with the nitrogen atom which bears them form a heterocycle of 5 to 8 links, preferably of 5 or 6 links, said heterocycle being possibly substituted by one or more identical or different radicals chosen from a linear alkyl radical in C1-C4 or branched in C3-C4, OH.

10. Cosmetic composition according to any one of claims 8 to 9, wherein the compound(s) of formula (I) or its tautomeric form (!') are, selected 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 AT \ 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 from compounds 3, 4, 16, 18, 26, 28, 29, 30, 67 and 75 and their salts and / or isomers and / or solvates, more preferably from compounds 4, 16, 18, 29, 30, 67 and 75 and their salts and / or isomers and / or solvates. Cosmetic composition according to any one of claims 8 to 10, wherein 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, wherein said at least one cosmetic adjuvant is selected from hy- gelling agents drophiles or lipophiles, preservatives, cosmetic actives such as anti-aging actives other than compounds of formula (I) or (!') or (II) or (II'), fatty substances such as oils, emulsifiers, antioxidants, vitamins, perfumes, fillers, sunscreens, odor absorbers, desquamating actives, moisturizing actives, emollients, and coloring materials, and mixtures thereof.

14. Composition according to any one of claims 8 to 13, having a pH 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, solvated and / or isomers, as defined in any one of claims 8 to 11, for the care of keratinous materials, in particular the skin.

16. A cosmetic skin care treatment method comprising applying to skin showing signs of aging, 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 method comprising applying to the skin, preferably to skin showing signs of aging, 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.