Composition comprising a thiopyridinone compound and an amino-sulfonic compound

Abstract

Composition comprising a thiopyridinone compound and an aminosulfonic compound. The present invention relates to a composition, in particular a cosmetic composition, comprising at least one compound of formula (I), at least one aminosulfonic compound of formula (II), and strictly less than 0.2% by weight of an alkali salt of thiosulfuric acid and / or its solvates such as hydrates, or totally free of an alkali salt of thiosulfuric acid and / or its solvates such as hydrates. Figure for the abstract: none

Description

Title of the invention: Composition comprising a thiopyridinone compound and an amino-sulfonic compound

[0001] The present invention relates to a composition, preferably cosmetic, for the care of keratinous materials, in particular skin care.

[0002] At various times in their lives, some people develop darker and / or more colored spots on their skin, particularly on their face and hands, giving their skin a heterogeneous appearance. These spots are primarily due to a high concentration of melanin in the keratinocytes located on the surface of the skin.

[0003] The use of harmless topical depigmentation substances with good efficacy is particularly desired for the purpose of reducing pigment spots.

[0004] For example, arbutin, niacinamide and kojic acid are known as skin depigmenting agents.

[0005] Furthermore, WO2012 / 080075 and WO2017 / 102349 disclose a new depigmenting or bleaching agent which is a thiopyridinone compound. This thiopyridinone compound exhibits particularly effective depigmenting or bleaching properties by reducing melanin production.

[0006] However, it has been discovered that thiopyridinone compounds tend to become unstable in a composition over time, particularly when the composition including this compound is exposed to UV radiation, i.e. thiopyridinone compounds are not photostable (i.e. photochemically stable).

[0007] Thus, an objective of the present invention is to propose a composition including a thiopyridinone compound with improved UV photostability.

[0008] Another objective is to propose a composition including a stable thiopyridinone compound. By "stable," we mean a composition that does not exhibit crystallization after manufacture at room temperature (20°C).

[0009] Another objective is to propose a composition including a thiopyridinone compound which exhibits odor stability over time and / or an absence of odor and / or an odor acceptable to the consumer.

[0010] The present invention meets these expectations.

[0011] The composition according to the invention is a stable composition containing a thiopyridinone compound. It contains said compound in photostable form, and has no odor or an odor acceptable to the consumer.

[0012] The invention thus relates to a composition, in particular a cosmetic one, comprising: i. at least one compound selected from compounds of formula (I), tautomers of formula (!'), their salts, their solvates, such as their hydrates, their optical isomers, their racemates, and mixtures thereof: w

[0013] in which,

[0014] - Ri denotes a radical chosen from a) a hydrogen atom, and b) an alkyl group linearly saturated in Ci-Cio or branched in C3-Ci0 optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, and

[0015] - R2 denotes a radical chosen from a) a hydrogen atom, b) a group a linear saturated hydrocarbon in CrCi2 or branched in C3-Ci2 or cyclic in C3-C8 optionally substituted by one or more groups, which may be identical or different, selected from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in CrC8, and c) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in CrC8, and

[0016] - R3 designates a radical chosen from a) a hydrogen atom, and b) an alkyl group saturated linearly in Ci-Cio or branched in C3-CiO; i. at least one amino-sulfonic compound chosen from the compounds corresponding to the following formula (II): O PN Vp R OH

[0017] (II)

[0018] in which:

[0019] - R designates a hydrogen atom or a group chosen from -OH and -NH2,

[0020] - X designates:

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030] - a hydrogen atom, - a group - n is equal to 0, 1, 2 or 3, and their physiologically acceptable salts; and i. strictly less than 0.2% by weight of an alkali salt of thiosulfuric acid and / or its solvates such as hydrates, or said composition is totally free of alkali salt of thiosulfuric acid and / or its solvates such as hydrates. The invention also relates to a non-therapeutic cosmetic treatment method for the care of keratinous materials, in particular for depigmentation, lightening and / or bleaching of keratinous materials, comprising a step of applying to the keratinous materials, preferably the skin, a composition according to the invention. The invention also relates to the non-therapeutic cosmetic use of a composition according to the invention for the care of keratinous materials, in particular for whitening, lightening and / or depigmenting keratinous materials. Thiopyridinone compound The composition according to the present invention comprises at least one compound selected from the compounds of formula (I), the tautomers of formula (!'), their salts, their solvates, such as their hydrates, their optical isomers, their racemates, and their mixtures. Two distinct thiopyridinone compounds, of formula (I) or (!'), can be used in combination. Thus, a single thiopyridinone compound of formula (I) or (!') or a combination of different thiopyridinone compounds of formula (I) or (!') can be used. The thiopyridinone compound(s) are chosen from the compounds of formula (I) below, the tautomers of formula (!') below, their salts, their solvates such as their hydrates, their optical isomers, their racemates and their mixtures:

[0031] [Chem.l] (i) (f)

[0032] in which:

[0033] Ri designates a radical chosen from:

[0034] a) a hydrogen atom, and

[0035] b) a linear saturated alkyl group in the form of Ci-Cio or branched in the form of C3-Ci0 optionally substituted by one or more groups, which may be identical or different, selected from

[0036] i) -O-R3, and

[0037] ii) -S-R3, and

[0038] R2 denotes a radical chosen from:

[0039] a) a hydrogen atom,

[0040] b) a linear saturated hydrocarbon group in C1-C12 or branched in C3-C12 or cyclic in C3-C8, optionally substituted by one or more groups, which may be identical or different, selected from

[0041] i) -O-R3,

[0042] ii) -S-R3,

[0043] iii) -C(O)-O-R3, and

[0044] iv) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more CrC8 alkoxy radicals and

[0045] c) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more CrC8 alkoxy radicals, and

[0046] R3 designates a radical chosen from:

[0047] a) a hydrogen atom, and

[0048] b) a linear saturated alkyl group in Ci-Cio or branched in C3-Ci0.

[0049] Hereinafter, within the meaning of the present invention and unless otherwise indicated:

[0050] - a hydrocarbon group "saturated, linear in CrCi2 or branched in C3-Ci2" is equivalent to a "linear (Ci-Ci2) or branched (C3-Ci2) alkyl group" which corresponds to a saturated hydrocarbon group, linear in CrCi2 or branched in C3-Ci2, preferably a linear hydrocarbon group in Ci-Ci0 or branched in C3-Ci0, and more preferably a linear hydrocarbon group in Ci-C6 or branched in C3-C6 Preferably, linear or branched groups may be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl groups; more preferably, saturated alkyl groups, linear or branched, may be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl and octyl groups, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl;

[0051] - a saturated hydrocarbon group "cyclic in C3-C8" is a cycloalkyl group mono- or bicyclic containing 3 to 8 carbon atoms, and in particular is a monocyclic cycloalkyl group in C5 to C7 such as a cyclohexyl group,

[0052] - an "alkoxy radical" is an alkyl-oxy radical for which the alkyl radical is a linear or branched CrCi6 hydrocarbon radical, and preferably a Ci-C8 hydrocarbon radical;

[0053] - when the alkoxy group is optionally substituted, this implies that the group alkyl is optionally substituted as defined above;

[0054] - an "aryl" group represents a carbon-based, monocyclic or bicyclic, fused or not, comprising from 5 to 12 carbon atoms, preferably from 6 to 10 carbon atoms, and in which at least one ring is aromatic; preferably, the aryl radical is a phenyl, biphenyl, naphthyl group, more preferably a phenyl group.

[0055] The salts of compounds of formula (I), (I'), (II) or (II') as defined below include conventional non-toxic salts of said compounds, such as those formed from an organic or inorganic acid or an organic or inorganic base.

[0056] Examples of salts of compounds of formula (I), (I'), (II) or (II') include:

[0057] - the salts obtained by adding the compound of formula (I) or (II) to:

[0058] - a mineral base, such as sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, sodium, potassium or calcium carbonate or hydrogen carbonate, for example; or

[0059] - an organic base such as a primary, secondary or tertiary alkylamine, by Examples include triethylamine and butylamine. This primary, secondary, or tertiary alkylamine may contain one or more nitrogen and / or oxygen atoms and may thus include, for example, one or more alcohol groups. Notable examples include 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylaminopropanol, 2-amino-2-(hydroxymethyl)-1,3-propanediol, and 3-(dimethylamino)propylamine.

[0060] Amino acid salts, for example lysine, arginine, guanidine, glutamic acid, and aspartic acid, can also be mentioned. Advantageously, the salts of Compounds of formula (I) or (II) (when they include a carboxy group) may be chosen from alkali or alkaline earth metal salts such as sodium, potassium, calcium or magnesium salts and ammonium salts.

[0061] A "salt of an organic or inorganic acid" is more particularly chosen from among the salts chosen from a salt derived from i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(O)2OH such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S(O)2OH such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid; x) alkoxysulfinic acids: Alk-OS(O)OH such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; xii) phosphoric acid H3PO4; xiii) acetic acid CH3C(O)OH; xiv) triflic acid CF3SO3H; and xv) tetrafluoroboric acid HBF4.

[0062] Acceptable solvates of the described compounds include conventional solvates such as those formed during the preparation of said compounds due to the presence of solvents. Examples include solvates due to the presence of water or linear or branched alcohols, such as ethanol or isopropanol.

[0063] Optical isomers are, in particular, enantiomers and diastereomers.

[0064] Compound (I') is the tautomeric form of compound (I) when a tautomeric equilibrium exists according to the following scheme:

[0065] According to one embodiment of the present invention, Ri represents a hydrogen atom.

[0066] According to one embodiment of the present invention, Ri of formula (I) and (I') represents a linear (Ci-Ci) or branched (C3-Ci) alkyl group, in particular a linear (Ci-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably, ethyl. In particular, said alkyl group of Ri' is unsubstituted.

[0067] According to one embodiment of the present invention, R2 represents a hydrogen atom.

[0068] According to one embodiment of the present invention, R2 represents a linear (Ci-Cio) or branched (C3-C10) alkyl group, in particular a linear (Cr C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group of R2 not being substituted.

[0069] According to one embodiment of the present invention, R2 of formula (I) and (!') represents a linear (C1-C10) or branched (C3-C10) alkyl group, in particular a linear (C1-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group being substituted by one or more groups selected from i), ii), iii) and iv) as defined above. Preferably, said alkyl group being substituted by one or two groups selected from i), ii) and iii), more preferably by one or two groups selected from i) and iii), better substituted by a group iii) as a carboxy.

[0070] Another variant for the radical R2 is that said alkyl group is substituted by a group iv) in particular substituted by a phenyl group.

[0071] According to another embodiment of the present invention, R2 represents a cycloalkyl group (in C3-C8), preferably a cycloalkyl group (in C5-C7) such as cyclohexyl.

[0072] According to another embodiment of the present invention, R2 represents an aryl group in C5-Ci2 optionally substituted by one or more hydroxyls and / or by one or more alkoxy radicals in CrC8, preferably a phenyl group in particular unsubstituted.

[0073] According to one embodiment, R3 represents a hydrogen atom.

[0074] According to another embodiment, R3 represents a saturated alkyl group, linear in C1-C10 or branched in C3-C10; in particular a linear (in Ci-C6) or branched (in C3-C6) alkyl group, preferably an alkyl group (in C1-C4) such as the methyl group.

[0075] Preferably, the compounds of formula (I) and the tautomer (!') or their salts, their optical isomers, racemates, and / or solvates such as their hydrates and their derivatives, alone or in mixture, have the following meanings:

[0076] Ri designates a radical chosen from:

[0077] a) a hydrogen atom, and

[0078] b) a linear saturated alkyl group in C1-C6 or branched in C3-C6 optionally substituted by one or more groups, which may be identical or different, selected from:

[0079] i) -O-R3, and

[0080] ii) -S-R3,

[0081] preferably optionally substituted by one or more groups i);

[0082] R2 denotes a radical chosen from:

[0083] a) a hydrogen atom;

[0084] b) a linear saturated hydrocarbon group in C1-C10 or branched in C3-C10 or cyclic in C3-C8 such as in C5-C6 optionally substituted by one or more groups, which may be identical or different, selected from:

[0085] i) -O-R3,

[0086] ii) -S-R3,

[0087] iii) -C(O)-O-R3, and

[0088] iv) a phenyl group optionally substituted by one or more hydroxyl groups and / or by one or more Ci-C4 alkoxy radicals such as methoxy,

[0089] preferably substituted by one or more groups selected from i) and iii), preferably iii) such as carboxy; and

[0090] R3 designates a radical chosen from:

[0091] a) a hydrogen atom, and

[0092] b) a linear saturated alkyl group in Ci-C6 or branched in C3-C6.

[0093] Preferably, the compounds of formula (I) and the tautomer (!') or their salts, their optical isomers, racemates, and / or their solvates such as their hydrates, alone or in mixture, have the following meanings:

[0094] Ri designates a radical chosen from:

[0095] a) a hydrogen atom, and

[0096] b) a linear saturated Ci-C4 or branched C3-C4 alkyl group optionally substituted by one or more groups, which may be identical or different, chosen from i) -OR3jplus preferably unsubstituted;

[0097] R2 denotes a radical chosen from:

[0098] a) a hydrogen atom; and

[0099] b) a linear saturated hydrocarbon group in C1-C10 or branched in C3-C10 or cyclic in C3-C8 as in C5-C6, optionally substituted by one or more groups, which may be identical or different, chosen from:

[0100] i) -O-R3,

[0101] iii) -C(O)-O-R3,

[0102] iv) an aryl group at C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals at C1-C4; and

[0103] R3 designates a radical chosen from:

[0104] a) a hydrogen atom, and

[0105] b) a linear saturated CrC4 or C3-C4 branched alkyl group such as methyl or ethyl.

[0106] Preferably, the compounds of formula (I) and the tautomer (!') or their salts, their optical isomers, racemates, and / or solvates such as hydrates and their derivatives, alone or in mixture, have the following meanings:

[0107] Ri is a hydrogen atom; and

[0108] R2 denotes a radical chosen from:

[0109] a) a hydrogen atom, and

[0110] b) a saturated hydrocarbon group, linear in C1-C5 or branched in C3-C5 or cyclic in C3-C8 such that C5-C6 may be identical or different, selected from v) -C(O)-O-R3, preferably substituted by a group iii) -C(O)-O-R3; R2 is more preferably a saturated hydrocarbon group, linear in C1-C4 or branched in C3-C4 substituted by a group iii) -C(O)-OR3; and

[0111] R3 denotes a radical chosen from:

[0112] a) a hydrogen atom, and

[0113] b) a linear saturated alkyl group in C1-C4 or branched in C3-C4 such as methyl or ethyl.

[0114] According to another preferred embodiment, the compounds of formula (I) and the tautomer (!') are selected from the compounds of formula (I”) below and also their tautomers of formula (!'”) below, their salts, their solvates and their optical isomers, and their racemates, alone or in mixture:

[0115] [Tables 1] OXX □ „ ry QHO JL .. -XO, (TYY ^3 N SH (I”) (I'”)

[0116] In formula (I”) and (!'”), Ri and R3 have the same meaning as Ri and R3 for the compounds of formula (I) and (!'), and X denotes an alkylene radical -(CH2)n- with n being an integer from 1 to 10 inclusive, preferably from 1 to 6, more preferably from 1 to 4, such that 1; preferably, R3 represents a hydrogen atom.

[0117] Among the compounds of formula (I), the following compounds are preferably used, and their tautomer (!') or their salts, their optical isomers, racemates, and / or solvates such as hydrates and their derivatives, alone or in mixture:

[0118] [Tables2] Structure No. Chemical Name CAS No. 1 / Y-. X-ethyl-2-thioxo-1,2-dihydroxypyridine-3-carboxamide 91859-75-5 2 / / ______ HX.....Y. ■•-' \< X-methyl-2-thioxo-1,2-dihydroxypyridine-3-carboxamide 91859-74-4 3 X-octyl-2-thioxo-1,2-dihydroxypyridine-3-carboxamide 91859-77-7 4 Y, Y%,. X La = a '"fY yy n * HYYYS N-cyclohexyl-2-thioxo-1, 2-dihydropyridine-3-carbo xamide 91859-78-8 7 z^Â^XJ h 1 N-[2-(4-methoxyphenyl)ethyl] -2-thioxo-1,2-dihydro pyridine-3-carboxamide 923682-88 -6 8 A .A YY AX< Yj'" Ys. N-(2-methylpropyl)-2-thio xo-1,2-dihydropyridine-3-carboxamide 1100027-7 9-9 9 H N-pentyl-2-thioxo-1,2-dih ydropyridine-3-carboxam ide 330667-57 -7 10 O A y y '■" '" N-nonyl-2-thioxo-1,2-dih ydropyridine-3-carboxam ide 1031149-4 4-6 11 H 0 £ H " "X N-(2-hydroxyéthyl)-2-thio xo-1,2-dihydropyridine-3-carboxamide 12 y s ■'<■•.■■"' y .. L '$ CK< N,N-diéthyl 2-mercaptoni cotinamide 13 H Xxx V’N----- ( X--P« s ï;ii N-éthyl-N-(2-hydroxyéthy l)-2-thioxo-1,2-dihydropyr idine-3-carboxamide 14 ijUmU» N-(2,3-dihydroxypropyl)-2-thioxo-1,2-dihydropyrid ine-3-carboxamide 15 -"■K „MX .A N-( 1,3-dihydroxypropan-2 -yl)-2-thioxo-1,2-dihydropyridin-3 -carboxamide ; 16 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl alaninate 17 !•; X''Y <> "O N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl phenyl alaninate 18 "X'r" N *■>•'“ 1 v 21 N' HH OH N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl] glycine 22 $ ■ b N,N-bis(2-hydroxyethyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 23 CI ï J N-(3-methoxypropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 24 ..CX N-butyl-2-thioxo-1,2-dihydropyridine-3-carboxamide ​Among these compounds, the following are particularly preferred:

[0119]

[0120] [Tables 3] CAS No. 1 Structure Chemical Name HJHU Jx AX' xx. H N-ethyl-2-thioxo-1,2-dihydroxypyridine-3-carboxamide 91859-75-5 2 I '1 1' I / V- N-methyl-2-thioxo-1,2-dihydroxypyridine-3-carboxamide 91859-74-4 4 ff' Y’’" ' X T--'':- N-benzyl-2-thioxo-1,2-dih ydropyridine-3-carboxami de 91859-79-9 6 À X h § H H N-cyclohexyl-2-thioxo-1,2 -dihydropyridine-3-carbox amide 91859-78-8 7 xAA h '1 h N-[2-(4-méthoxyphényl)ét hyl] -2-thioxo-1,2-dihydrop yridine- 3 -carboxamide 923682-88- 6 9 Z <y' -Si ' ^.--- ;;: ? >1 X -Ax N-pentyl-2-thioxo-1,2-dih ydropyridine-3-carboxami de 330667-57- 7 11 / X \ H f' N. X'\ YX ^qh 'N'" Xs H N-(2-hydroxyéthyl)-2-thio xo-1,2-dihydropyridine-3-c arboxamide 12 x YjyX ■■>:•■■■ X>is J t .( x k XX X X N,N-diéthyl 2-mercaptonic otinamide 14 x.v . Jx ■■ X< ■ XH: X” Ax "■•••'■" sX N-(2,3-dihydroxypropyl)-2 -thioxo-1,2-dihydropyridin e-3-carboxamide 15 "'■ ;> K .¾ N-( 1,3-di hydroxypropan-2 -yl)-2-thioxo-1,2-dihydropyridin-3 -carboxamide 16 'n'" ■■■ •2 CH.. f ^5'---; N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl alanine ate 17 .HL,. V- ~ r X,------( / / \ / ™”\ XJ / N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]phenyl 1 ethyl alaninate 18 . ' tJ: N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl ethyl glyeinate 19 < X * 0 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycine nate 20 £ N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine (INCI name: 2-MERCAPT ONICOTINOYL GLYCINE) 21 < ci-r œ H N-methyl-N-[(2-thioxo-1,2 -dihydropyridin-3-yl)carbo nyl] glycine

[0121] More preferably, among these compounds, the following compounds are particularly preferred:

[0122] [Tables4] Structure No. Chemical Name CAS No. 1 .■■■. W XX Am N-ethyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-75-5 ' HH 9 X Xy* X”" XX XX N N-pentyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 330667-57- 7 16 (Yv TX" %. K / N-[(2-thioxo-1,2-dihydropyridine-3-yl)carbonyl]ethyl alanine ate 18 X xiX 'XX U - <x     -x -xs    '     x œ. n-méthyl-n-[(2-thioxo-1,2 -dihydropyridin-3-yl)carbo nyoglycinate d'éthyle 19 • < n-[(2-thioxo-1,2-dihydrop yridin-3-yl)carbonyl]glyci nate 20 T / H. N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine (INCI name: 2-MERCAPT ONICOTINOYL GLYCIN E) 21 H N-methyl-N-[(2-thioxo-1,2 -dihydropyridin-3-yl)carbo nyl] glycine

[0123] Even more preferably, among these compounds, the following compounds are particularly preferred:

[0124] [Tables5] No. Structure Chemical Name 18 H $ N-methyl-N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbonylglycinate of ethyl 19 / \ n ff '•X. / \ a N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate of ethyl 20 O r ï N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine (INCI name: 2-MERCAPT ONICOTINOYL GLYCIN E) In a most preferred embodiment, the compound according to the present invention

[0125]

[0126] is as follows: [Tableauxô] 20 N- [(2-thioxo-1,2-dihydrop yridin-3 - yl) carbony 1] glycone (INCI name: 2-MERCAPT ONICOTINOYL GLYCIN E)

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] All the above compounds can be obtained by a chemical process known to those skilled in the art, using commercially available reagents. The thiopyridinone compound can be prepared in accordance with the process described, for example, in document EP-A-3390363 or WO 2017 / 102349. The compound thiopyridinone can be an active ingredient or active compound in cosmetic or dermatological products. The term "active ingredient" or "active compound" used here refers to an ingredient or compound that has an active cosmetic or dermatological property. Preferably, the amount of the thiopyridinone compound(s) of formula (I) or (!') in the composition according to the present invention is at least 0.01% by weight, preferably at least 0.03% by weight, and more preferably at least 0.05% by weight relative to the total weight of the composition. Preferably, the amount of the thiopyridinone compound(s) of formula (I) or (!') in the composition according to the present invention is less than 5% by weight, preferably less than 3% by weight, and more preferably less than 1% by weight relative to the total weight of the composition. Preferably, the amount of the thiopyridinone compound(s) of formula (I) or (!') in the composition according to the present invention is between 0.01% and 3% by weight, preferably between 0.03% and 2% by weight, and more preferably between 0.05% and 1% by weight relative to the total weight of the composition. Aminosulfonic compound The composition according to the present invention comprises at least one amino-sulfonic compound selected from the compounds corresponding to the following formula (II):

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140] (II) in which: - R denotes a hydrogen atom or a group chosen from -OH and -NH2, - X designates: - a hydrogen atom, - a group - a group

[0141]

[0142]

[0143]

[0144] - n is equal to 0, 1, 2 or 3, and their physiologically acceptable salts. The invention extends its scope to optical and / or geometric isomers of compounds of formula (II), alone or in mixtures in all proportions. Among the compounds of formula (II) preferably used according to the invention, the following may be mentioned: - 4-(2-hydroxyethyl)piperazine-l-ethanesulfonic acid, which corresponds to the following formula: 4-(2-hydroxyethyl)piperazine-l-(2-hydroxypropanesulfonic acid) which corresponds to the following formula: 4-(2-hydroxyethyl)piperazine-l-propanesulfonic acid, which corresponds to the following formula: 3-Morpholinopropanesulfonic acid, which corresponds to the following formula: 2-Morpholinoethanesulfonic acid, which corresponds to the following formula: piperazine-1,4-bis-(2-ethanesulfonic acid) which corresponds to the following formula: piperazine-1,4-bis(2-hydroxypropane sulfonic acid) which corresponds to the following formula: O

[0145] Among these compounds, 4-(2-hydroxyethyl)pipe razine-l-ethanesulfonic acid or HEPES, marketed in particular under the name HEPES-LUV by the company TAIWAN HOPAX, is particularly preferred.

[0146] The quantity of amino-sulfonic compound of formula (II) usable according to the invention can represent from 0.01 to 20%, preferably from 0.1 to 15% and better from 1 to 10% of the total weight of the composition. Alkaline salt of thiosulfuric acid

[0147] The composition according to the present invention (i) either comprises strictly less than 0.2% by weight of an alkali salt of thiosulfuric acid and / or its solvates such as hydrates, (ü) is totally free of alkali salt of thiosulfuric acid and / or its solvates such as hydrates.

[0148] By "totally free of alkali salt of thiosulfuric acid and / or its solvates such as hydrates", it is meant that the composition comprises 0% by weight of alkali salt of thiosulfuric acid and / or its solvates such as hydrates. In other words, it contains none.

[0149] By "alkaline salt of thiosulfuric acid" is meant a salt of thiosulfuric acid with an alkali metal such as sodium or potassium, preferably sodium. Preferably, the alkali salt of thiosulfuric acid is sodium thiosulfate.

[0150] When an alkali salt of thiosulfuric acid and / or its solvates such as hydrates, preferably sodium thiosulfate, is present in the composition, it is preferably present in a content of less than 0.1% by weight relative to the total weight of the composition, preferably less than 0.01% by weight, preferably less than 0.0001% by weight. Antioxidant agent

[0151] Preferably, the composition according to the invention also includes at least one antioxidant agent.

[0152] Preferably, the antioxidant agent is chosen from carnosine compounds, vitamin E and its derivatives, vitamin C and its derivatives such as vitamin CG (ascorbyl glucoside), arginine, glycyrrhizic acid and its salts such as dipotassium glycyrrhizate, and mixtures thereof.

[0153] Preferably, the composition according to the invention comprises at least one antioxidant agent selected from carnosine compounds, vitamin E and its derivatives, vitamin C and its derivatives such as vitamin CG, arginine, glycyrrhizic acid and its salts such as dipotassium glycyrrhizate, and mixtures thereof. Preferably, the composition according to the invention comprises at least one antioxidant agent selected from carnosine, vitamin E and its derivatives, vitamin C and its derivatives such as vitamin CG, arginine, glycyrrhizic acid and its salts such as dipotassium glycyrrhizate, and mixtures thereof.

[0154] Preferably, the composition according to the invention comprises at least two antioxidant agents chosen from those mentioned above, preferably at least three, more preferably at least four, even better at least five antioxidant agents chosen from those mentioned above.

[0155] C compounds of camosine

[0156] Preferably, the carnosine compound is chosen from compounds of formula (III): (HD

[0157] in which RI represents H or CH3 and R2 represents H or COOH,

[0158] and their salts.

[0159] The salts of compounds of formula (III) are preferably salts of compounds of formula (III) with mineral acids, in particular salts of formula (IV):

[0160] where n represents 1, 2 or 3 and A represents HCl or HNO3 and RI represents H or CH3 and R2 represents H or COOH.

[0161] The camosine compounds useful for the composition according to the present invention are known and accessible by conventional organic chemistry processes.

[0162] Preferably, the camosine compound is selected from camosine, L-carnosine, D-camosine, D / L-camosine, carnicine, carnicine HCl salt, anserine, D-anserine, L-anserine, L-anserine HNO3 salt, and combinations thereof.

[0163] As a commercial product for camosine, mention can be made of that available under the brand Dragosine® PN 844033 from Symrise.

[0164] Advantageously, the camosin compound, preferably camosin, is present in an amount ranging from 0.01% by weight to 5% by weight, preferably from 0.1% by weight to 3% by weight, more preferably from 0.3% by weight to 1% by weight relative to the total weight of the composition.

[0165] Vitamin E and its derivatives

[0166] Vitamin E includes tocopherols and tocotrienols: s, tocopherols tocotrienols.

[0167] In particular, vitamin E includes

[0168] α-tocopherol

[0169] [3-tocopherol

[0170] y-tocopherol

[0171] β-tocopherol

[0172] a-tocotrienol

[0173]

[0174] [3-tocotrienol y-tocotrienol

[0175]

[0176]

[0177] Examples of vitamin E derivatives include pharmaceutically acceptable compounds such as acetate, sulfate, succinate, benzoate, propionate, sorbate, oleate, orotate, linoleate, nicotinate, palmitate, allophanate, and phosphate. Preferably, vitamin E and / or the vitamin E derivative is selected from α-tocopherol, γ-tocopherol, β-tocopherol, β-tocopherol, tocopheryl acetate, tocopheryl succinate, tocopheryl benzoate, tocopheryl propionate, tocopheryl sorbate, tocopheryl oleate, tocopheryl orotate, tocopheryl linoleate, tocopheryl nicotinate, and mixtures thereof. Preferably, the composition according to the present invention comprises vitamin E.

[0179] More preferably, the composition according to the present invention comprises a-tocopherol, such as that marketed under the name DL ALPHA TOCOPHEROL® by the company ZHEJIANG NHU COMPANY.

[0180] Advantageously, the total content of vitamin E and / or its derivative is 0.01% by weight to 1% by weight, preferably 0.05% by weight to 0.8% by weight, more preferably 0.1% by weight to 0.5% by weight, relative to the total weight of the composition.

[0181] Vitamin C and its derivatives

[0182] Vitamin C corresponds to L-ascorbic acid.

[0183] Ascorbic acid has the following formula (V) structure:

[0184] By "ascorbic acid derivative", preferably means a compound selected from 5,6-di-O-dimethylsilylascorbate (notably sold by Exsymol under the reference PRO-AA®), potassium salt of DL-alpha-tocopheryl-DL-ascorbyl-phosphate also called Potassium Ascorbyl Tocopheryl Phosphate (sold by SEPPIC under the reference SEPIVITAL EPC®), magnesium ascorbyl phosphate, sodium ascorbyl phosphate (sold by DSM under the reference Stay-C 50®), disodium ascorbyl sulfate, sulfinyl-L-ascorbic acid, glucopyranosyl-L-ascorbic acid and ascorbyl glucoside.

[0185] By "ascorbyl glucoside" or vitamin CG, we mean the condensation product of glucose, in D form, i.e. in the form of glucopyrannose a or [3 or furannose a or [3, or in L form, with ascorbic acid, preferably in L form. Preferably, the ascorbyl glucoside is L-ascorbic acid 2-OaD-glucopyranoside, notably available under the trade name AA2G® from the company HAYASHIBARA.

[0186] Examples include RECKON ORGANICS' Ascorbic acid L® (pure synthetic ascorbic acid) or DSM nutritional product's Ascorbic acid Ultrafine powder® (natural extract).

[0187] Preferably, ascorbyl glucoside is used.

[0188] Advantageously, the total content of vitamin C and / or its derivative is 0.1% by weight to 1% by weight, preferably 0.2% by weight to 0.8% by weight, more preferably 0.3% by weight to 0.7% by weight relative to the total weight of the composition.

[0189] A rginine

[0190] The composition according to the invention may include arginine as an antioxidant agent. The arginine (2-amino-5-carbamimidamidopentanoic acid) may be L- or S-arginine.

[0191] Advantageously, arginine is present in an amount ranging from 0.1% by weight to 5% by weight, preferably from 0.3% by weight to 4% by weight, more preferably from 0.5% by weight to 3% by weight relative to the total weight of the composition.

[0192] Glycyrrhizic acid and / or its salts

[0193] The composition according to the invention may include glycyrrhizic acid and / or one of its salts such as dipotassium glycyrrhizate.

[0194] The term "salt" means a salt formed by an inorganic or organic base. Examples of salts include the ammonium salt of glycyrrhizic acid and dipotassium glycyrrhizate. Preferably, the salt of glycyrrhizic acid according to the invention is dipotassium glycyrrhizate.

[0195] Glycyrrhizic acid or (3[3,20[3]-20-carboxy-l l-oxo-30-norolean-12-en-3-yl 2-O-[3-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid is a heteroside, the aglycone part of which (an acidic terpene) is linked to an acidic sugar dimer of glucuronic acid.

[0196] It corresponds to formula (VI) below: y €(W(VI) • r

[0197] Dipotassium glycyrrhizate corresponds to the formula (VII) below: (VII) HQ

[0198] Preferably, glycyrrhizic acid and / or its salts such as dipotassium glycyrrhizate according to the invention is used at a concentration of 0.01% to 2%, preferably 0.05% to 1.5% and even more preferably 0.1% to 1% relative to the total weight of the composition.

[0199] Preferably, the composition according to the invention comprises the three antioxidant agents which are vitamin CG, arginine and dipotassium glycyrrhizate.

[0200] Preferably, the composition according to the invention comprises the four antioxidant agents which are vitamin CG, arginine, dipotassium glycyrrhizate and camosine.

[0201] Preferably, the composition according to the invention comprises the five antioxidant agents which are vitamin E, vitamin CG, arginine, dipotassium glycyrrhizate and camosine.

[0202] Preferably, the composition comprises from 0.05% to 5% by weight of antioxidant agent(s) relative to the total weight of the composition, preferably from 0.1% to 4% by weight, preferably from 0.2% to 3% by weight.

[0203] Preferably, the composition of the present invention is transparent or translucent. According to some preferred embodiments, the composition according to the invention is a transparent composition.

[0204] For the purposes of this invention, a transparent or translucent composition is defined as a composition having a turbidity value of less than 800 NTU, preferably less than 500 NTU, preferably less than 200 NTU, preferably less than 150 NTU, preferably less than 100 NTU, preferably less than 50 NTU, and preferably less than 30 NTU. Preferably, the turbidity of the compositions is at least 0.1 NTU, and preferably at least 1 NTU.

[0205] NTUs (nephelometric turbidity units) are the units of measurement for the turbidity of a composition. Turbidity measurement is carried out, for example, with a Hach Company model 2100Q Portable Turbidimeter, the tubes used for measurement being referenced AR0413A cat 24347-06. Measurements are performed at room temperature (from 20°C to 25°C).

[0206] Preferably, the composition is transparent and has a turbidity value between 0.1 and 200 NTU, preferably between 1 and 150 NTU, preferably between 1.5 and 50 NTU, preferably between 2 and 30 NTU.

[0207] Preferably, the composition according to the invention is substantially free of surfactant. By "substantially free" is meant that the composition comprises less than 3% by weight, preferably less than 1% by weight, preferably less than 0.5% by weight, preferably less than 0.3% by weight of the total composition by weight of surfactant. Preferably, the composition according to the invention is completely free of surfactant.

[0208] Preferably, the composition according to the invention is substantially free of fats. By "substantially free" is meant that the composition comprises less than 1% by weight, preferably less than 0.2% by weight, preferably less than 0.1% by weight relative to the total weight of the composition, of fats. Preferably, the composition according to the invention is completely free of fats. By "fats" is meant any solid, pasty, or liquid lipophilic compound, in particular waxes and oils. Physiologically acceptable environment

[0209] In addition to the compounds indicated above, the composition according to the invention comprises a physiologically acceptable medium.

[0210] By "physiologically acceptable medium" is meant a medium particularly suitable for the application of a composition of the invention on keratinous materials, in particular the skin.

[0211] By "skin" we mean the entire skin of the body, and the scalp and preferably the skin of the face, décolletage, neck, arms and forearms, hands and even more preferably the skin of the face (in particular the forehead, nose, cheeks, lips, chin), décolletage and neck.

[0212] 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 appearance in which the composition is to be packaged.

[0213] The cosmetic compositions of the invention are preferably in the form of an O / W emulsion.

[0214] The physiologically acceptable medium may include water, preferably demineralized water, and optionally one or more solvent(s) miscible with water.

[0215] 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 the total weight of said composition.

[0216] 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.

[0217] A suitable water for the invention may be a floral water such as cornflower water and / or a mineral and / or thermal water such as VITTEL water, VICHY water or LA ROCHE POSAY water.

[0218] Among water-miscible organic solvents (at room temperature - 25°C), one or more cosmetically acceptable water-miscible organic solvents may be mentioned, which may be alcohols: in particular monovalent alcohols such as ethyl alcohol, propanediol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol; diols such as ethylene glycol, propylene glycol, butylene glycol and pentylene glycol; and ethers such as monomethyl, monoethyl and monobutyl ethers of ethylene glycol, monomethyl, monoethyl and monobutyl ethers of propylene glycol, and monomethyl, monoethyl and monobutyl ethers of butylene glycol, and glycerin.

[0219] The water-miscible organic solvent(s) may be present in a concentration of 0.01% to 30% by weight, preferably 0.1% to 25% by weight and more preferably 1% to 20% by weight, relative to the total weight of the composition.

[0220] The composition according to the invention may also include any water-soluble or water-dispersible compound such as gelling agents, film-forming polymers, thickeners and mixtures thereof.

[0221] The composition according to the invention may comprise niacinamide or one of its derivatives. For the purposes of the invention, niacinamide has the following structure:

[0222] By "niacinamide derivative" is preferably understood to mean a compound in which the amide group of niacinamide is secondary or tertiary, preferably substituted by one or two alkyl groups independently selected from C1-C4 alkyl groups and / or in which at least one hydrogen atom of the pyridine group is replaced by a C1-C4 alkyl group.

[0223] Preferably, the compound chosen from among niacinamide and its derivatives is niacinamide. For example, the product Niacinamide PC® marketed by DSM NUTRITIONAL PRODUCTS may be cited.

[0224] Preferably, the composition comprises from 0.1% to 20% by weight of the compound selected from niacinamide and its derivatives relative to the total weight of the composition, preferably from 0.5% to 15% by weight, preferably from 0.8% to 10% by weight.

[0225] The composition according to the invention may comprise at least one sequestrant. Preferred sequestrants include salts of ethylenediaminedisuccinic acid, EDTA and its salts, and mixtures thereof.

[0226] Ethylenediaminedisuccinic acid is a compound with the formula: HCL H -K G HO "O

[0227] Preferably, the salt of ethylenediaminedisuccinic acid is chosen from alkali metal salts, such as potassium and sodium salts, ammonium salts, and amine salts. Alkali metal salts of ethylenediaminedisuccinic acid are particularly preferred.

[0228] Preferably, the salt of ethylenediaminedisuccinic acid used according to the invention is trisodium ethylenediaminedisuccinate.

[0229] Such a compound is for example that marketed under the name Natrlquest® E30 by the company Innospec Active Chemicals at 37% by weight in water.

[0230] Preferably, the composition comprises from 0.001% to 1% by weight of the salt of ethylenediaminedisuccinic acid, preferably from 0.005% to 0.5% by weight, more preferably from 0.01% to 0.05% by weight of the salt of ethylenediaminedisuccinic acid relative to the total weight of the composition.

[0231] In a particular embodiment of the invention, the composition according to the present invention may also include at least one pH correcting agent (pH corrector).

[0232] Two or more pH adjusting agents may be used in combination. Thus, a single type of pH adjusting agent or a combination of different types of pH adjusting agents may be used.

[0233] As a pH correcting agent, at least one acidifying agent and / or at least a basifying agent (alkaline agent).

[0234] The acidifying agent may be a monovalent or polyvalent acid, such as divalent.

[0235] Acidifying agents may be, for example, mineral (inorganic) acids such as hydrochloric acid, sulfuric acid, phosphoric acid, or organic acids such as carboxylic acids, for example tartaric acid, citric acid and lactic acid, as well as sulfonic acids.

[0236] The alkalizing agent may be a monovalent or polyvalent base, such as divalent.

[0237] Alkalizing agents can be mineral (inorganic) or organic, or hybrid.

[0238] Mineral alkalizing agents may be selected from aqueous ammonia; alkali metal carbonates or bicarbonates such as sodium or potassium carbonates and sodium or potassium bicarbonates; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and mixtures thereof.

[0239] Organic alkalizing agents can be selected from organic amines such as alkanolamines, amino acids and mixtures thereof.

[0240] The pH correcting agent may be present in an amount of 0.01% by weight or more, preferably 0.05% by weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.

[0241] The pH correcting agent may be present in an amount of 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.

[0242] The pH correcting agent may be present in an amount from 0.01% to 15% by weight, preferably from 0.05% to 10% by weight, and more preferably from 0.1% to 5% by weight or less, relative to the total weight of the composition.

[0243] It is preferable that the composition according to the present invention has a pH of 4.5 or more, and more preferably of 5 or more.

[0244] It is preferable that the composition according to the present invention has a pH of 7.0 or less, and more preferably of 6.5 or less.

[0245] It is preferable that the composition according to the present invention has a pH of 4.5 to 6.5, and more preferably of 5.5 to 6.5.

[0246] The pH of the composition means the pH of the aqueous phase of the composition according to the present invention.

[0247] It may be preferable that at least one buffer or buffering agent also be used, such as the pH correcting agent, in combination with the acidifying agent and / or the alkalizing agent, in order to stabilize the pH of the composition according to the present invention.

[0248] Any commonly known buffer may be used. For example, salts of acids or bases, preferably salts of weak acids or weak bases, may be used. For example, sodium citrate or sodium lactate may be used as a buffer if citric acid or lactic acid is used as the acidifying agent. Additives

[0249] A cosmetic composition according to the invention may also further include any additive commonly used in the field concerned, for example selected from gums, resins, dispersing agents, polymers, essential oils, preservatives, perfumes, neutralizers, antiseptics, UV protectants, cosmetic actives and mixtures thereof.

[0250] It is part of the routine operations of a person skilled in the art to adjust the nature and quantity of additives present in compositions according to the invention, so that the cosmetic properties and the desired stability properties of the latter are not affected.

[0251] The composition used according to the invention comprising in particular at least one thiopyridinone compound of formula (I) or (I') described above can be presented in all the galenic forms normally used in the cosmetic field.

[0252] It may be in particular in the form of an aqueous solution, hydroalcoholic solution, possibly gelled, a lotion-type dispersion possibly biphasic, an oil-in-water or water-in-oil or multiple emulsion, an aqueous gel, It consists of a dispersion of oils in an aqueous phase, notably using spherules. These spherules can be polymeric particles or, better yet, ionic and / or non-ionic lipid vesicles, or they can be in the form of a powder, serum, paste, flexible stick, or other liquid. It can have a solid, pasty, or more or less fluid consistency. It can be applied to the skin as an aerosol. It can also be presented in solid form, for example, as a stick.

[0253] Thus, the composition may include all the constituents usually employed in the envisaged topical application and administration.

[0254] 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.

[0255] Said or said thiopyridinone compounds 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 route.

[0256] By "administered topically", we mean an application to the surface of the skin concerned.

[0257] 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.

[0258] The composition may or may not be rinsed off after being applied to the skin. Applications

[0259] The cosmetic compositions covered by the invention may be facial or body care products.

[0260] The compositions according to the invention are cosmetic compositions intended for skin care.

[0261] These compositions are therefore intended to be applied to the skin.

[0262] According to another of its objects, the present invention also relates to a process non-therapeutic cosmetic treatment for the care of keratinous materials, in particular for depigmentation, lightening and / or bleaching of keratinous materials, comprising a step of application on the keratinous materials, preferably the skin, of a composition, preferably cosmetic, as described above.

[0263] The present invention also relates to the non-therapeutic cosmetic use of a composition, preferably cosmetic, as described above for the care of keratinous materials, in particular for whitening, lightening and / or depigmenting keratinous materials.

[0264] A cosmetic implementation of the invention is therefore only intended for aesthetic defects of the skin, and therefore does not have a therapeutic effect.

[0265] By “treatment” we mean a non-therapeutic treatment capable of producing an aesthetic effect without preventing or correcting a pathological dysfunction of the skin.

[0266] The invention will be illustrated in the following non-limiting examples. Unless otherwise stated, percentages are expressed as a percentage of the total weight of the composition (% w / w).

[0267] The compositions are prepared according to the usual methods of formulating cosmetic compositions.

[0268] Example: Evaluation of compositions according to the invention and comparative

[0269] The compositions according to the invention Cl to C7 and comparative CCI* have been prepared.

[0270] Their stability at 45°C and their photostability were then evaluated.

[0271] Stability was evaluated at T0 and after 2 months (T2M) at 45°C. The results show that the compositions according to the invention Cl to C7 exhibit consistent chemical stability of the compound 2-MERCAPTONICOTINOYL GLYCINE at T0 and at T2M at 45°C. Photostability evaluation protocol

[0272] The photostability of the examples according to the invention Cl to C7 and of the comparative example CCI* was tested. The photostability of the examples according to the invention and the comparative example was evaluated following the procedure described below.

[0273] First, the amount of 2-MERCAPTONICOTINOYL GLYCINE in the formula is measured by HPLC / UV. A specific amount of the formula is spread evenly onto a PMMA plate to obtain a layer of approximately 2 mg / cm² (n=4 plates). All plates are exposed to UV light for 11 minutes until a dose of 5 J / cm² (UVA flux 0.00789 W / cm² and UVB flux 0.000488 W / cm²), corresponding to the average daily UV dose, is reached using a solar simulator. The plates are removed, and the solvent is used to remove the formula film, and the 2-MERCAPTONICOTINOYL GLYCINE is then extracted. This extract is then quantified to determine the concentration of the 2-MERCAPTONICOTINOYL GLYCINE compound using HPLC / UV.

[0274] The percentage of photostability is given as follows:

[0275] % of compound 2-MERCAPTONICOTINOYL GLYCINE after UV exposure / % of initial compound 2-MERCAPTONICOTINOYL GLYCINE x 100.

[0276] The results are as follows:

[0277] [Tables 7] Ingrédient (% p / p) CCI* Cl C2 C3 C4 C5 C6 C7 ACTIFS 8,60 8,60 8,60 8,60 9,60 9,60 AGENT BASIFIANT Qs Qs Qs Qs Qs Qs Qs Qs NIACINAMIDE 8,00 8,00 8,00 8,00 8,00 8,00 TOCOPHEROL 0,20 PARFUM Qs Eau Qsp 1 00 Qsp 1 00 Qsp 1 00 Qsp 1 00 Qsp 1 00 Qsp 1 00 Qsp 1 00 Qsp 1 00 ARGININE 1,00 1,00 SOLVANTS ORGANIQUE S 15,00 15,00 15,00 15,00 15,00 15,00 15,00 15,00 GELIFIANT 0,15 0,15 0,15 0,15 0,15 0,15 0,15 0,15 PPG-26-BUTETH-26 (and) PEG-40 HYDROGENATED CASTOR OIL 1,00 0,50 DIPOTASSIUM GLYCYRR HIZATE 0,30 0,30 0,30 ASCORBYL GLUCOSIDE 0,50 0,50 0,50 0,50 ACIDE HYDROXYETHY LPIPERAZINE ETHANE SULFONIQUE (HEPES) 5,00 5,00 5,00 5,00 5,00 5,00 5,00 CARNOSINE 0,50 0,50 0,50 TRISODIUM ETHYLENED IAMINE DISUCCINATE 0,10 0,10 0,10 0,10 0,10 0,10 0,10 0,10 Conservateur Qs Qs Qs Qs Qs Qs Qs Qs 2-MERCAPTONICOTINO YL GLYCINE 0,50 0,50 0,50 0,50 0,50 0,50 0,50 0,50 ACIDE CITRIQUE Qs Qs Qs QS QS Qs PHOTOSTABILITE (%) ( quantité résiduelle en % de 86 94 95 95 93 92 94 93 2-mercaptonicotinoyl glyci born)

[0278] They show that the compound 2-MERCAPTONICOTINOYL GLYCINE is significantly more photostable in the compositions according to the invention Cl to C7 than in the comparative composition CCI*.< / x>

Claims

1. Demands Composition, particularly cosmetic, including: i. at least one compound selected from compounds of formula (I), tautomers of formula (!'), their salts, their solvates, such as their hydrates, their optical isomers, their racemates, and mixtures thereof: in which, - Ri denotes a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in the Ci-CiO configuration or a branched C3-CiO configuration optionally substituted by one or more groups, which may be the same or different, chosen from i) -O-R3, and ii) -S-R3, and - R2 denotes a radical chosen from a) a hydrogen atom, b) a linear saturated hydrocarbon group in the CrCi2 configuration or a branched C3-Ci2 configuration or a cyclic C3-C8 configuration optionally substituted by one or more groups, which may be the same or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) a C5-Ci2 aryl group, optionally substituted by one or more hydroxyl groups and / or by one or more Ci-C8 alkoxy radicals, and c) an aryl group in C5-C12, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in CrC8 and - R3 designates a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in Ci-Cio or branched in C3-Ci0; i. at least one amino-sulfonic compound selected from the compounds corresponding to the following formula (II): (II) in which: - R denotes a hydrogen atom or a group chosen from -OH and -NH2, - X denotes: - a hydrogen atom, - a group - a group 0 , -N i pn R OH - n is equal to 0, 1, 2 or 3, and their physiologically acceptable salts; and i. strictly less than 0.2% by weight of an alkali salt of thiosulfuric acid and / or its solvates such as hydrates, or said composition is totally free of an alkali salt of thiosulfuric acid and / or its solvates such as hydrates.

2. Composition according to claim 1, wherein the compounds of formula (I) and the tautomer (!') or their salts, their optical isomers, racemates, and / or solvates such as hydrates and their derivatives, alone or in mixture, have the following meanings: Ri is a hydrogen atom; and R2 denotes a radical selected from: a) a hydrogen atom, and b) a saturated hydrocarbon group, linear in C1-C5 or branched in C3-C5 or cyclic in C3-C8 such that C5-C6 may be identical or different, selected from v) -C(O)-O-R3, preferably substituted by a iii) -C(O)-O-R3 group; R2 is more preferably a saturated hydrocarbon group, linear in C1-C4 or branched in C3-C4 substituted by a iii) -C(O)-OR3 group; and R3 designates a radical chosen from: a) a hydrogen atom, and b) a linear saturated CrC4 or C3-C4 branched alkyl group such as methyl or ethyl.

3. Composition according to claim 1 or 2, wherein the thiopyridinone compound is selected from: [Tables 2] jt Structure Jtom -ciism^ue CAS W. 1 N-ethyl-2-thfcx3-1 2-dtàytopÿrtfee-S-cafboKatWe 51859-75- 5 2 -- -x£ 2 N-mé:1hyl-2-tt3soxs-^ dfeyîÈFcqjyjKfee-S-carboxsnsid® 51859-74- 4 3 ,2-i®ytlr®p / ïkfee-3-cæboxamkïa 91859-77- 4 t44>Kizÿt-2'&Haxo-1,2-rfihy^repyjicfise-S-satbexansKie 91859-79- s 5 .....\\ v ..2-dih^FDpÿncljRe-3-C3fbaK3RSKfe 1.C4857-16-1 S A: > ...-^ «-{2-Ç4-ffiétt®xyp^éay(>éthy^^ 24hîàxà-l .2-.tftày^rspyTEfce-3-cafboxansidê 923682- 88-6 8 ..-¾ ..--¾ N*(2-mé8hÿ8p5©pÿj>2- Biioxo-1.2-cH&ÿdrcpy?i!fiRe-3-cafboxsraide 11ÛB027- 75-3 § ,2- dihydropyfkfiRe-3-cafboxaRSRte 33C6S7- 57-7 w 'Sx*'' XS«-'' X^' Xx>x' V- / hl-«1W^2-t!(SX0-1,2-dfàyrfropÿTkfee-S-©arbexamidë 1031149- 44-8 11 <> N-424iydfSKÿ®a^-2-«ticaco-1.2-®y^repyfi>dsRe-3-ca&Gxawie 12 X '■X""' XV' '■-:■ N,N4Ba&2- mercapÎOTBCc^BawBde 13 :: < X N4smyl-?H2- hydr0Kyéthyt)-24h^ 1,2-Æhyrirspyf kfee-3-cafbexaiRidë 14 1H2Jt d^draxyprfipÿH-2-tftiææ-1.2-diihydrspyfidsne-S-carbœœreScfe r ? !5 « $ to 15 ..<> •\. ...y S-{13-tffcydrcx'ÿ'propafi-S-ytî-2-StoB-î .2-dtày{£repyrkiîrsè-3-eafbcKamide 18 * ' £$ K .--'Y ,.A\ ••''■x . AY \XX X << / M-fïS-thïsxo-IS- d:Lby^rop>'TKfe-3- 17 & H4(24hK«0-t2a d:iby <fepÿïKfe-3- 15 I $ Xï'f XX N <Mh«>^t24hit»æ-1 2^ib\âMpyîitfiix-3-sï)cai$œw§o^ 19 ...... i a. .to. .a " 1..... V. .•XX-. X--• ■•-•>< <• S-KS-tttaco-l^- ®y <SrepyrKfe-3-yS^arPwWxW^. 2Q ,i ,» f '1 v T X'xÿr'* H-p-tmoxo-i,â-£@hÿrêropyréi!R<J-yljcar&w^Iÿcsre 21 CO-'r 1,2-tShÿîtopyf KiàR-3- 22 J * rf' X.-'' ■■ hydro:<yé^4^24îBæ:G> -1 S2-Æhyarspyf kgne-3-, castoexaRside 23 Y y - & Ç thioxo-l .2-dfeÿdrcpyddsRe-3-cas'boxanlide 24 ri » ■'X ,V. y- 4 if cfihÿéKîpyfidsRe-3-cas'boxamide

4. Composition according to any one of the preceding claims, wherein the thiopyridinone compound is as follows: [Tables] 20 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]gl ycin H

5.

6. A composition according to any one of the preceding claims, wherein the compound thiopyridinone is present in an amount of at least 0.01% by weight, preferably at least 0.03% by weight, and more preferably at least 0.05% by weight relative to the total weight of the composition; and / or in an amount of less than 5% by weight, preferably less than 3% by weight, and more preferably less than 1% by weight relative to the total weight of the composition; and / or in an amount of between 0.01% and 3% by weight, preferably between 0.03% and 2% by weight, more preferably between 0.05% and 1% by weight relative to the total weight of the composition. A composition according to any one of the preceding claims, wherein the aminosulfonic compound of formula (II) is selected from: 4-(2-hydroxyethyl)piperazine-l-ethanesulfonic acid, which corresponds to the following formula: 4-(2-hydroxyethyl)piperazine-l-(2-hydroxypropanesulfonic acid) which corresponds to the following formula: 4-(2-hydroxyethyl)piperazine-1-propanesulfonic acid, which corresponds to the following formula: 3-Morpholinopropanesulfonic acid, which corresponds to the following formula: 2-Morpholinoethanesulfonic acid, which corresponds to the following formula: piperazine-1,4-bis-(2-ethanesulfonic acid) which corresponds to the following formula: - piperazine-l,4-bis(2-hydroxypropane sulfonic acid) which corresponds to the following formula: 0 OH OH p tT y S 0 7 I 1 I 1 / J XS. A. J OH OH d" preferably the amino-sulfonic compound of formula (II) is 4-(2-hydroxyethyl)piperazine-l-ethanesulfonic acid or HEPES.

7. Composition according to any one of the preceding claims, wherein the amino-sulfonic compound of formula (II) is present from 0.01 to 20%, preferably from 0.1 to 15% and, better still, from 1 to 10% of the total weight of the composition.

8. Composition according to any one of the preceding claims, wherein the alkali salt of thiosulfuric acid is sodium thiosulfate, preferably it is present in a content of less than 0.1% by weight relative to the total weight of composition, preferably less than 0.01% by weight, preferably less than 0.0001% by weight.

9. Composition according to any one of the preceding claims, which also includes at least one antioxidant agent.

10. Composition according to claim 9, wherein the antioxidant agent is selected from carnosine compounds, vitamin E and its derivatives, vitamin C and its derivatives such as vitamin CG (ascorbyl glucoside), arginine, glycyrrhizic acid and its salts such as dipotassium glycyrrhizate, and mixtures thereof; preferably the antioxidant agent is selected from carnosine, vitamin E and its derivatives, vitamin C and its derivatives such as vitamin CG, arginine, glycyrrhizic acid and its salts such as dipotassium glycyrrhizate, and mixtures thereof.

11. Composition according to claim 9 or 10, comprising at least two antioxidants, preferably at least three, plus preferably at least four, even better at least five antioxidant agents; preferably the composition includes vitamin CG, arginine and dipotassium glycyrrhizate; preferably the composition includes vitamin CG, arginine, dipotassium glycyrrhizate and camosin; preferably the composition includes vitamin E, vitamin CG, arginine, dipotassium glycyrrhizate and camosin.

12. Composition according to any one of claims 9 to 11, wherein the antioxidant agent is a camosin compound selected from compounds of formula (III): in which RI represents H or CH3 and R2 represents H or COOH, and their salts, preferably the camosine compound is selected from camosine, L-carnosine, D-camosine, D / L-camosine, carnicine, camicine HCl salt, anserine, D-anserine, L-anserine, L-anserine HNO3 salt, and combinations thereof, preferably camosine; preferably present in an amount from 0.01% by weight to 5% by weight, preferably from 0.1% by weight to 3% by weight, more preferably from 0.3% by weight to 1% by weight relative to the total weight of the composition.

13. Composition according to any one of claims 9 to 11, wherein the antioxidant agent is vitamin E or one of its derivatives, preferably selected from α-tocopherol, γ-tocopherol, γ-tocopherol, β-tocopherol, tocopheryl acetate, tocopheryl succinate, tocopheryl benzoate, tocopheryl propionate, tocopheryl sorbate, tocopheryl oleate, tocopheryl orotate, tocopheryl linoleate, tocopheryl nicotinate, and mixtures thereof, preferably vitamin E; preferably present in a content of 0.01% by weight to 1% by weight, preferably 0.05% by weight to 0.8% by weight, more preferably 0.1% by weight to 0.5% by weight, relative to the total weight of the composition.

14. Composition according to any one of claims 9 to 11, wherein the antioxidant agent is vitamin C or one of its derivatives, preferably selected from 5,6-di-O-dimethylsilylascorbate, potassium salt of DL-alpha-tocopheryl-DL-ascorbyl-phosphate, magnesium ascorbyl phosphate, sodium ascorbyl phosphate, disodium ascorbyl sulfate, sulfinyl-L-ascorbic acid, glucopyranosyl-L-ascorbic acid and ascorbyl glucoside, preferably ascorbyl glucoside; preferably present in a content of 0.1% by weight to 1% by weight, preferably 0.2% by weight to 0.8% by weight, more preferably 0.3% by weight to 0.7% by weight relative to the total weight of the composition.

15. Composition according to any one of claims 9 to 11, wherein the antioxidant agent is arginine, preferably present in an amount from 0.1% by weight to 5% by weight, preferably from 0.3% by weight to 4% by weight, more preferably from 0.5% by weight to 3% by weight relative to the total weight of the composition.

16. Composition according to any one of claims 9 to 11, wherein the antioxidant agent is glycyrrhizic acid and / or one of its salts, preferably dipotassium glycyrrhizate; preferably present at a concentration of 0.01% to 2%, preferably 0.05% to 1.5% and even more preferably 0.1% to 1% relative to the total weight of the composition.

17. Composition according to any one of the preceding claims, which is transparent, and / or which is substantially free of surfactant, and / or which is substantially free of fat.

18. Composition according to any one of the preceding claims, comprising a physiologically acceptable medium which may comprise water and optionally one or more water-miscible solvent(s).

19. A non-therapeutic cosmetic treatment method for the care of keratinous materials, in particular for depigmentation, lightening and / or bleaching of keratinous materials, comprising a step of applying to the keratinous materials, preferably the skin, a composition according to one of the preceding claims.

20. Non-therapeutic cosmetic use of a composition according to any one of claims 1 to 18 for the care of materials keratinous, in particular for bleaching, lightening and / or depigmenting keratinous materials.