SOLUBILIZATION OF THIOPYRIDINONE COMPOUND AND COMPOSITION COMPRISING THE SAME

Abstract

SOLUBILIZATION OF THIOPYRIDINONE COMPOUND AND COMPOSITION COMPRISING THE SAME The present invention relates to a composition comprising: (1) at least one thiopyridinone compound; and (2) at least one compound selected from vitamin B3 and its derivatives. The present invention can provide a composition including thiopyridinone compound(s) (1) with increased solubility of the thiopyridinone compound(s) (1) over time. Figure for abstract: none

Description

Title of the invention: SOLUBILIZATION OF THIOPY-RIDINONE COMPOUND AND COMPOSITION COMPRISING THE LATTER Technical field

[0001] The present invention relates to a stabilized composition comprising a thiopyridinone compound, and the use thereof for the care of keratin materials and, in particular, the skin. CONTEXT OF ART

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

[0003] The use of harmless topical depigmenting substances having good efficacy is particularly desired for the purpose of treating pigmentation spots.

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

[0005] On the other hand, it has been discovered that certain thiopyridinone compounds exhibit good depigmentation activity, even at low concentrations, such as those disclosed for example in WO2012 / 080075 and WO2017 / 102349. The thiopyridinone compound can exhibit strong depigmentation or whitening effects by reducing melanin production. DISCLOSURE OF THE INVENTION

[0006] However, it has been discovered that a thiopyridinone compound may be imperfectly solubilized in the composition, thereby reducing the bioavailability of the thiopyridinone compound. Therefore, there is a need to provide a composition comprising a thiopyridinone compound(s) having improved solubility and stability over time.

[0007] The above objective can be achieved by a composition comprising:

[0008] (1) at least one compound selected 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:

[0009] in which

[0010] Ri denotes a radical chosen from

[0011] a) a hydrogen atom, and

[0012] b) a linear C1-C10 or branched C3-C10 saturated alkyl group optionally substituted by one or more groups, which may be the same or different, chosen from

[0013] i) -O-R3, and

[0014] ii) -S-R3,

[0015] and

[0016] R2 denotes a radical chosen from

[0017] a) a hydrogen atom,

[0018] b) a linear or branched C3-Ci2 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, which may be the same or different, chosen from

[0019] i) -O-R3,

[0020] ii) -S-R3,

[0021] iii) -C(O)-O-R3, and

[0022] iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals and

[0023] c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals

[0024] in which

[0025] R3 denotes a radical chosen from

[0026] a) a hydrogen atom, and

[0027] b) a linear C1-C10 or branched C3-C10 saturated alkyl group;

[0028] and

[0029] (2) at least one compound selected from vitamin B3 and its derivatives.

[0030] It may be preferable that:

[0031] Ri of formula (I) and (!') represents a hydrogen atom;

[0032] or

[0033] Ri of formula (I) and (!') represents a linear alkyl group (Ci-Ci0) or a group branched (C3-C10) alkyl, especially a straight (C1-C6) alkyl group or a branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl, in particular said alkyl group of R1 is unsubstituted.

[0034] It may be preferable that:

[0035] R2 of formula (I) and (I') represents a hydrogen atom;

[0036] or

[0037] R2 of formula (I) and (I') represents a linear alkyl group (C1-C10) or a branched alkyl group (C3-C10), in particular a linear alkyl group (C1-C6) or a branched alkyl group (C3-C6), such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably, a methyl or ethyl group; said alkyl group of R2 not being substituted.

[0038] It may be preferable that:

[0039] R2 of formula (I) and (I') represents a linear alkyl group (C1-C10) or a branched alkyl group (C3-C10), in particular a linear alkyl group (C1-C6) or a branched alkyl group (C3-C6), 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) such as carboxy.

[0040] It may be preferable that:

[0041] R2 of formula (I) and (I') represents a cycloalkyl group (C3-C8), preferably a cycloalkyl group (C5-C7) such as cyclohexyl;

[0042] or

[0043] R2 of formula (I) and (I') represents a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals, preferably a phenyl group in particular unsubstituted.

[0044] It may be preferable that:

[0045] R3 of formula (I) and (I') represents a hydrogen atom;

[0046] or

[0047] R3 of formula (I) and (I') represents a linear C1-C10 or branched C3-C10 saturated alkyl group; in particular a linear (C1-C6) alkyl group or a branched (C3-C6) alkyl group, preferably a (C1-C4) alkyl group such as a methyl group.

[0048] It may be more preferable that:

[0049] Ri of formula (I) and (I') represents a radical chosen from

[0050] a) a hydrogen atom, and

[0051] b) a linear C1-C6 or C3-C6 branched saturated alkyl group optionally substituted by one or more groups, which may be the same or different, chosen from

[0052] i) -O-R3, and

[0053] ii) -S-R3,

[0054] preferably optionally substituted with one or more groups i);

[0055] R2 of formula (I) and (!') represents a radical chosen from

[0056] a) a hydrogen atom, and

[0057] b) a linear C1-C10 or branched C3-C10 or cyclic C3-C8 as in C5-C6 saturated hydrocarbon group, optionally substituted by one or more groups, which may be identical or different, chosen from:

[0058] i) -O-R3,

[0059] ii) -S-R3,

[0060] iii) -C(O)-O-R3, and

[0061] iv) a phenyl group optionally substituted by one or more hydroxyls and / or by one or more C1-C4 alkoxy radicals such as methoxy,

[0062] preferably substituted by one or more groups selected from i) and iii), preferably iii) such as carboxy; and

[0063] R3 of formula (I) and (!') represents a radical chosen from

[0064] a) a hydrogen atom, and

[0065] b) a linear C1-C6 or branched C3-C6 saturated alkyl group,

[0066] preferentially, the compounds of formula (I) and the tautomer (!), their salts, solvates, such as their hydrates, their optical isomers, their racemates, and their mixtures, have the following meanings:

[0067] Ri of formula (I) and (!') represents a radical chosen from:

[0068] a) a hydrogen atom, and

[0069] b) a linear C1-C4 or branched C3-C4 saturated alkyl group optionally substituted by one or more groups, which may be the same or different, selected from i) -OR3>more preferably unsubstituted;

[0070] R2 of formula (I) and (!') represents a radical chosen from

[0071] a) a hydrogen atom, and

[0072] b) a linear C1-C10 or branched C3-C10 or cyclic C3-C8 as in C5-C6 saturated hydrocarbon group, optionally substituted by one or more groups, which may be the same or different, chosen from

[0073] i) -O-R3,

[0074] iii) -C(O)-O-R3, and

[0075] iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more C1-C4 alkoxy radicals; and

[0076] R3 of formula (I) and (!') represents a radical chosen from:

[0077] a) a hydrogen atom;

[0078] b) a linear C1-C4 or branched C3-C4 saturated alkyl group such as methyl or ethyl.

[0079] Compound (1) may be selected from compounds 1 to 24 below, their tautomers, their salts, their solvates, such as their hydrates, their optical isomers, their racemates, and their mixtures, in particular compounds 1, 2, 4, 6, 7, 9, 11, 12, 14, 15, 16, 17, 18, 19, 20 or 21, more particularly, 1, 9, 16, 18, 19, 20 or 21, preferably, 18, 19, 20 or 21, and more preferably, 20:

[0080] [Tables2] N° Structure Nom chimique 1 U H H N-éthyl-2-thioxo-1,2-dihydropyridin e-3-carboxamide 2 .........c • > N-méthyl-2-thioxo-1,2-dihydropyrid ine- 3 -carboxamide 3 N / "’* Y'"'-' N-octyl-2-thioxo-1,2-dihydropyridin e-3-carboxamide 4 if A A Af J 4. N-benzyl-2-thioxo-1,2-dihydropyrid ine- 3 -carboxamide 5 .—, —f f / A^ A / 2 A N-phényl-2-thioxo-1,2-dihydropyrid ine- 3 -carboxamide 6 a A / ‘‘ H N-cyclohexyl-2-thioxo-1,2-dihydrop yridine-3-carboxamide 7 ii ... . txr " N-[2-(4-méthoxyphényl)éthyl]-2-thi oxo-1,2-dihydropyridine-3-carboxa mide 8 •ks N-(2-méthylpropyl)-2-thioxo-1,2-di hydropyridine-3-carboxamide 9 ÎS ■ ï ' H >4. N-pentyl-2-thioxo-1,2-dihydropyridi ne-3-carboxamide 10 ■Z*Sr N-nonyl-2-thioxo-1,2-dihydropyridi ne-3-carboxamide r ' V 11 / K ‘X H (î XY 'NX || Oi’ s H N-(2-hydroxyéthyl)-2-thioxo-1,2-di hydropyridine-3-carboxamide 12 <XXXZ "Z' * X i ^CHs N,N-diéthyl 2-mercaptonicotinamide 13 0 "■' '^v'''' X'M < 1 / X '-—oh Y" XS Yhi; N-éthy 1-N - (2-hy droxy éthy 1) -2-thiox o-1,2-dihydropyridine-3-carboxami de 14 UY0- N-(2,3-dihydroxypropyl)-2-thioxo-l ,2-dihydropyridine-3-carboxamide 15 .A, 3jN N-(1,3-dihydroxypropan-2-yl)-2-thi oxo-1,2-dihydropyridine-3-carboxa mide i H 16 H / N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl alaninate 17 C- < A'-A xf K<; ' Ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]phenyl alaninate 18 Ethyl N-methyl-N-[(2-thioxo-1,2-dihydro pyridin-3-yl)carbonyl]glycinate 19 Ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate 20 ilv XX ..XT N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine 21 CA v^r -¾ H N-methyl-N-[(2-thioxo-1,2-dihydro pyridin-3-yl)carbonyl]glycine 22 N,N-bis(2-hydroxyethyl)-2-thioxo-l,2-dihydropyridine-3-carboxamide 23 Jk Jk TT * C; A N-(3-methoxypropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 24 S £• N-butyl-2-thioxo-1,2-dihydropyridine-3-carboxamide

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087] The amount of the compound(s) (1) in the composition according to the present invention may be from 0.01% to 10% by weight, preferably from 0.05% to 5% by weight, and more preferably from 0.1% to 3% by weight, relative to the total weight of the composition. At least one compound (2) is preferably vitamin B3. The amount of vitamin B3 or its derivatives in the composition according to the present invention may be from 0.06% to 60% by weight, preferably from 0.3% to 30% by weight, more preferably from 0.6% to 18% by weight, relative to the total weight of the composition. The composition according to the present invention may be intended for the whitening of a keratin material, preferably the skin. The present invention also relates to a cosmetic process, preferably a bleaching process, for a keratin material, preferably the skin, comprising the following step: the application to the keratin material of the composition according to the present invention. Another aspect of the present invention is a use of at least one compound b) selected from vitamin B3 and its derivatives in a composition comprising (1) at least one compound selected from the compounds of formula (I) below, the tautomers of formula (I) below, their salts, their solvates, such as their hydrates, their optical isomers, their racemates, and their mixtures: (î) (H

[0088] in which

[0089] Ri denotes a radical chosen from

[0090] a) a hydrogen atom, and

[0091] b) a linear C1-C10 or branched C3-C10 saturated alkyl group optionally substituted by one or more groups, which may be the same or different, chosen from

[0092] i) -O-R3, and

[0093] ii) -S-R3,

[0094] and

[0095] R2 denotes a radical chosen from

[0096] a) a hydrogen atom,

[0097] b) a linear C1-C12 or branched C3-C12 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, which may be the same or different, chosen from

[0098] i) -O-R3,

[0099] ii) -S-R3,

[0100] iii) -C(O)-O-R3, and

[0101] iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals and

[0102] c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals

[0103] in which

[0104] R3 denotes a radical chosen from

[0105] a) a hydrogen atom, and

[0106] b) a linear C1-C10 or branched C3-C10 saturated alkyl group

[0107] in order to stabilize the compound(s) (1). Best mode for carrying out the invention

[0108] After extensive research, the inventors have discovered that it is possible to provide a composition including a thiopyridinone compound or thiopyridinone compounds exhibiting increased solubility of the thiopyridinone compound(s) over time.

[0109] Thus, the composition according to the present invention comprises:

[0110] (1) at least one compound selected 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 (hereinafter, the compound is called "thiopyridinone compound"): © ©) [YES] in which

[0112] Ri denotes a radical chosen from

[0113] a) a hydrogen atom, and

[0114] b) a linear C1-C10 or branched C3-C10 saturated alkyl group optionally substituted by one or more groups, which may be the same or different, chosen from

[0115] i)-O-R3, and

[0116] ii)-S-R3,

[0117] and

[0118] R2 denotes a radical chosen from

[0119] a) a hydrogen atom,

[0120] b) a linear C1-C12 or branched C3-C12 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, which may be the same or different, chosen from

[0121] i) -O-R3,

[0122] ii) -S-R3,

[0123] iii) -C(O)-O-R3, and

[0124] iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals and

[0125] c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals

[0126] in which

[0127] R3 denotes a radical chosen from

[0128] a) a hydrogen atom, and

[0129] b) a linear C1-C10 or branched C3-C10 saturated alkyl group;

[0130] and

[0131] (2) at least one compound selected from vitamin B3 and its derivatives.

[0132] The composition according to the present invention may exhibit increased solubility of the thiopyridinone compound (1) therein.

[0133] In other words, the composition according to the present invention can increase the solubility of the thiopyridinone compound (1) therein. Increased "solubility" means that the composition according to the present invention comprising the thiopyridinone compound (1) does not exhibit any turbidity, and is rather homogeneous, transparent and stable.

[0134] In addition, the increased stability of the thiopyridinone compound (1) may provide improved or increased bioavailability of the thiopyridinone compound (1) which may function as a depigmenting or bleaching agent. Therefore, the composition according to the present invention may provide increased or improved depigmenting or bleaching effects.

[0135] Hereinafter, the composition, use and others according to the present invention will be described in detail.

[0136] [Composition]

[0137] The composition according to the present invention comprises:

[0138] (1) at least one thiopyridinone compound; and

[0139] (2) at least one compound selected from vitamin B3 and its derivatives.

[0140] The thiopyridinone compound (1) and vitamin B3 and its derivatives (2), as well as other features of the composition according to the present invention will be explained below.

[0141] (Thiopyridinone compound)

[0142] The composition according to the present invention comprises (1) at least one thiopyridinone compound. Two or more thiopyridinone compounds (1) may be used in combination. Thus, a single type of thiopyridinone compound (1) or a combination of different types of thiopyridinone compounds (1) may be used.

[0143] The thiopyridinone compound (1) is selected 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: W (H

[0144] in which

[0145] Ri denotes a radical chosen from

[0146] a) a hydrogen atom, and

[0147] b) a linear C1-C10 or branched C3-C10 saturated alkyl group optionally substituted by one or more groups, which may be the same or different, chosen from

[0148] i) -O-R3, and

[0149] ii) -S-R3,

[0150] and

[0151] R2 denotes a radical chosen from

[0152] a) a hydrogen atom,

[0153] b) a linear or branched C3-Ci2 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, which may be the same or different, chosen from

[0154] i) -O-R3,

[0155] ii) -S-R3,

[0156] iii) -C(O)-O-R3, and

[0157] iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals and

[0158] c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals

[0159] in which

[0160] R3 denotes a radical chosen from

[0161] a) a hydrogen atom, and

[0162] b) a linear C1-C10 or branched C3-C10 saturated alkyl group.

[0163] Hereinafter, within the meaning of the present invention and unless otherwise indicated: - a "saturated, linear CrCi2 or branched C3-Ci2" hydrocarbon group is equivalent to a "linear (CrCi2) or branched (C3-Ci2) alkyl group" which corresponds to a saturated, linear CrCi2 or branched C3-Ci2 hydrocarbon group, preferably a linear C1-Cio or branched C3-Cio hydrocarbon group, and more preferably a linear C1-C6 or branched C3-C6 hydrocarbon group; preferably, the linear or branched groups may be chosen from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl groups; more preferably, the saturated, linear or branched alkyl groups may be chosen 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;

[0164] - a “C3-C8 cyclic” saturated hydrocarbon group is a cycloalkyl group mono or bicyclic containing from 3 to 8 carbon atoms, and in particular is a group monocyclic C5-C7 cycloalkyl such as cyclohexyl,

[0165] - an "alkoxy radical" is an alkyloxy radical for which the alkyl radical is a linear or branched hydrocarbon radical in CrCi6, and preferably a hydrocarbon radical in CrC8;

[0166] - when the alkoxy group is optionally substituted, this implies that the group alkyl is optionally substituted as defined above;

[0167] - an “aryl” group represents a carbon-based, monocyclic or bi- cyclic, fused or not, comprising from 5 to 12 carbon atoms, preferably from 6 to 10 carbon atoms, and in which at least one cycle is aromatic; preferably, the aryl radical is a phenyl, biphenyl, naphthyl group, more preferably a phenyl group;

[0168] - the expression “at least one” is equivalent to the expression “one or more”; and

[0169] - the term "inclusive" for a concentration range means that the limits of this range are included in the defined range.

[0170] 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.

[0171] As salts of the compounds of formula (I), (I'), (II) or (II'), mention may be made of:

[0172] the salts obtained by addition of the compound of formula (I) or (II) to: - a mineral base, such as sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, and sodium, potassium or calcium carbonate or hydrogen carbonate, for example;

[0173] or - an organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine. This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and / or oxygen atoms and may thus comprise, for example, one or more alcohol functions. Mention may be made in particular of 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylaminopropanol, 2-amino-2-(hydroxymethyl)-1,3-propanediol and 3-(dimethylamino)propylamine.

[0174] Mention may also be made of amino acid salts, for example lysine, arginine, guanidine, glutamic acid and aspartic acid. Advantageously, the salts of the compounds of formula (I) or (II) (when they comprise a carboxy group) may be chosen from alkali or alkaline earth metal salts such as sodium, potassium, calcium or magnesium salts and ammonium salts.

[0175] An “organic or inorganic acid salt” is more particularly chosen from salts selected from a salt derived from i) hydrochloric acid HCl, ii) hydrobromide 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.

[0176] Acceptable solvates of the compounds described in the specification 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.

[0177] The optical isomers are in particular the enantiomers and the diastereoisomers.

[0178] The compound (!') is the tautomeric form of the compound (I) when a tautomeric equilibrium exists according to the following scheme: W (H

[0179] According to one embodiment of the present invention, Ri represents a hydrogen atom.

[0180] According to one embodiment of the present invention, Ri 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, ethyl. In particular, said alkyl group of Ri' is not substituted.

[0181] According to one embodiment of the present invention, R2 represents a hydrogen atom.

[0182] According to one embodiment of the present invention, R2 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 of R2 not being substituted.

[0183] 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) such as carboxy.

[0184] Another variant for the radical R2 is that said alkyl group is substituted by a group iv) in particular substituted by a phenyl group.

[0185] According to another embodiment of the present invention, R2 represents a cycloalkyl group (C3-C8), preferably a cycloalkyl group (C5-C7) such as cyclohexyl.

[0186] According to another embodiment of the present invention, R2 represents a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals, preferably a phenyl group in particular unsubstituted.

[0187] According to one embodiment, R3 represents a hydrogen atom.

[0188] According to another embodiment, R3 represents a saturated, linear C1-C10 or branched C3-C10 alkyl group; in particular a linear (C1-C6) or branched (C3-C6) alkyl group, preferably an alkyl group (C1-C4) such as the methyl group.

[0189] 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

[0190] have the following meanings:

[0191] Ri denotes a radical chosen from

[0192] a) a hydrogen atom, and

[0193] b) a linear C1-C6 or branched C3-C6 saturated alkyl group optionally substituted by one or more groups, which may be the same or different, chosen from

[0194] i) -O-R3, and

[0195] ii) -S-R3,

[0196] preferably optionally substituted with one or more groups i);

[0197] R2 denotes a radical chosen from

[0198] a) a hydrogen atom;

[0199] b) a linear C1-C10 or branched C3-C10 or cyclic C3-C8 such as C5-C6 saturated hydrocarbon group optionally substituted by one or more groups, which may be identical or different, chosen from:

[0200] i) -O-R3,

[0201] ii) -S-R3,

[0202] iii) -C(O)-O-R3, and

[0203] iv) a phenyl group optionally substituted by one or more hydroxyls and / or by one or more C1-C4 alkoxy radicals such as methoxy,

[0204] preferably substituted by one or more groups selected from i) and iii), preferably iii) such as carboxy; and

[0205] R3 denotes a radical chosen from

[0206] a) a hydrogen atom, and

[0207] b) a linear C1-C6 or branched C3-C6 saturated alkyl group

[0208] 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 as a mixture

[0209] have the following meanings:

[0210] Ri denotes a radical chosen from

[0211] a) a hydrogen atom, and

[0212] b) a linear C1-C4 or branched C3-C4 saturated alkyl group optionally substituted by one or more groups, which may be the same or different, selected from i) -OR3jplus preferably unsubstituted;

[0213] R2 denotes a radical chosen from

[0214] a) a hydrogen atom; and

[0215] b) a linear C1-C10 or branched C3-C10 or cyclic C3-C8 as in C5-C6 saturated hydrocarbon group, optionally substituted by one or more groups, which may be the same or different, chosen from:

[0216] i) -O-R3,

[0217] iii) -C(O)-O-R3,

[0218] iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more C1-C4 alkoxy radicals; and

[0219] R3 denotes a radical chosen from

[0220] a) a hydrogen atom, and

[0221] b) a linear C1-C4 or branched C3-C4 saturated alkyl group such as methyl or ethyl.

[0222] 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 as a mixture

[0223] have the following meanings:

[0224] Ri is a hydrogen atom; and

[0225] R2 denotes a radical chosen from

[0226] a) a hydrogen atom, and

[0227] b) a saturated hydrocarbon group, linear C1-C5 or branched C3-C5 or cyclic C3-C8 such that C5-C6 may be the same or different, chosen from v) -C(O)-O-R3, preferably substituted by a group iii) -C(O)-O-R3; R2 is more preferably still a saturated hydrocarbon group, linear C1-C4 or branched C3-C4 substituted by a group iii) -C(O)-OR3; and

[0228] R3 denotes a radical chosen from

[0229] a) a hydrogen atom, and

[0230] b) a linear C1-C4 or branched C3-C4 saturated alkyl group such as methyl or ethyl.

[0231] According to another preferred embodiment, the compounds of formula (I) and the tautomer (!) are selected from the compounds of formula (II) below and also their tautomers of formula (II') below, their salts, their solvates and their optical isomers, and their racemates, alone or as a mixture:

[0232] [Tables3] OO Il X to, 0 ■ NS 1 HO .1 .XO -y Y Jl 0 (II) (il')

[0233] In formula (II) and (II'), R1 and R3 have the same meaning as R1 and R3 for the compounds of formula (I) and (I'), and X denotes an alkylene radical -(CH2)n- with n being an integer ranging inclusively from 1 to 10, preferably from 1 to 6, more preferably from 1 to 4, such that 1, preferably, R3 represents a hydrogen atom.

[0234] Among the compounds of formula (I), the following compounds are preferably used, and their tautomer (I') or their salts, their optical isomers, racemates, and / or solvates such as hydrates and their derivatives, alone or in mixture:

[0235] [Tables4] No. Structure Chemical Name CAS No. 1 -, _ Xk; ""x- ■•-•.y. N-Ethyl-2-thioxo-1,2-dihydropyridine-3-carb oxamide 91859-75-5 2 / / \\ / ■ A N-methyl-2-thioxo-1,2 -dihydropyridine-3-car boxamide 91859-74-4 3 y'y--- N-octyl-2-thioxo-1,2-dihydropyridine-3-carb oxamide 91859-77-7 4 i-, Xx N-benzyl-2-thioxo-1,2 -dihydropyridine-3-car boxamide 91859-79-9 5 / / \\ r-—¢- —V 7 \ 7 w \\ N-phenyl-2-thioxo-1,2 -dihydropyridine-3-car boxamide 104857-16- 1 6 o YY' \zox H N-cyclohexyl-2-thioxo -1,2-dihydropyridine-3 -carboxamide 91859-78-8 7 ^,1 8 .-'Vv N-(2-methylpropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 1100027-79 -9 il H i ​​YYSG 9 Y y-'^y N-pentyl-2-thioxo-1,2-dihydropyridine-3-car boxamide 330667-57- 7 10 O . YY^ ■'^X. --■Y-^. -•'■^x N-nonyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 1031149-44 -6 11 0 . / Y* XGH H N-(2-hydroxyethyl)-2-thioxo-1,2-dihydropyri dine-3-carboxamide 12 / \ / / \ '.K 7 ZN,N-diethyl 2-mercaptonicotinami de 13 © ■K < v— V N-ethyl-N-(2-hydroxy ethyl)-2-thioxo-1,2-di hydropyridine-3-carbo xamide 14 $ ! j K ! N-(2,3-dihydroxyprop yl)-2-thioxo-1,2-dihyd ropyridine-3-carboxa mide 15 ' ,À, N-( 1,3-dihydroxyprop an-2-yl)-2-thioxo-1,2-dihydropyridine-3-car boxamide 16 Ç CH5 'AA \ h / N-[(2-thioxo-l,2-dihy dropyridin-3-yl)carbon yl]alaninate d'éthyle 17 y Y ,.X 'ï. Ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]phenyl alaninate 18 Y YY ""■•>•;•■■""" '-y? U Jx YY ->r" "■"'•■ \ S't, Ethyl N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate 19 xUC^xA Ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate 20 il OH A “ y N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine 21 K .0 --yrr NH N-methyl-N-[(2-thiox o-1,2-dihydropyridin-3-yl)carbonyl]glycine 22 Œ: N,N-bis(2-hydroxyethyl)-2-thioxo-1,2-dihyd ropyridine-3-carboxa mide 23 ri H ~ - N-(3-methoxypropyl)-2-thioxo-1,2-dihydropyridine-3-c arboxamide 24.-lx,.xX N-butyl-2-thioxo-1,2-dihydropyridine-3-car boxamide

[0236] Among these compounds, the following compounds are more particularly preferred:

[0237] [Tables5] No. Structure Chemical Name CAS No. 1 .X / X / 'X. t 'k " ZZ "ZH N-ethyl-2-thioxo-1,2-dihydropyridine-3-car boxamide 91859-75-5 2 ........%. 6 N-methyl-2-thioxo-1, 2-dihy dropyridine- 3 -c arboxamide 91859-74-4 4 3 £ '■ ' . ( Z N-benzyl-2-thioxo-1, 2-dihy dropyridine- 3 -c arboxamide 91859-79-9 6 Z "N " " / . / ' N ; h .••'"X •''■"x'' ZV %- / •■■" N- [2- (4-methoxyphen yl)ethy 1] -2-thioxo-1,2 -dihy dropyridine- 3 -ca rboxamide 923682-88-6 9 Z' N^X \-z ^Z" ]!: ZN N-pentyl-2-thioxo-1,2 -dihy dropyridine- 3 -ca rboxamide 330667-57-7 11 .■■■■■'z Zx / n '"' T fZx ; CH ^'SH N-(2-hydroxyethyl)-2 -thioxo-1,2-dihydropy ridine- 3 -carboxamide 12 ç l A. k 'TH.. -,_A ..JN,N-diethyl 2-mercaptonicotinamide 14 ;ki kk .Y- A.. N-(2,3-dihydroxyprop yl)-2-thioxo-1,2-dihydropyridine-3-carboxa mide 15 a Y Yk Yk HH: S N-( 1,3-dihydroxyprop an-2-yl)-2-thioxo-1,2-dihydropyridine-3-car boxamide 16 ''ï / '•S \ H / N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl alaninate 17 [(YUYJY y «J N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]phenyl ethyl alaninate 18 C' v'Y'" A"" Yz KA <k *- ''n-' n                                        ! cm ;, n-méthyl-n-[(2-thiox o-1,2-dihydropyridin-3-yl)carbonyl]glycinat e d'éthyle 19 , .-Â*- x ® N-[(2-thioxo-1,2-dihy dropyridin-3-yl)carbo nyljglycinate ethyl 20 0 N-methyl-N-[(2-thiox o-1,2-dihydropyridin-3-yl)carbonyl]glycine

[0238] More preferably, among these compounds, the following compounds are more particularly preferred:

[0239] [Tableauxô] No. Structure Chemical Name CAS No. 1 £ - A / ] H *<§ H N-ethyl-2-thioxo-1,2-dihydropyridine-3-car boxamide 91859-75-5 9 XNA N-;-'" 'V' ît N N-pentyl-2-thioxo-1,2 -dihy dropyridine- 3 -ca rboxamide 330667-57-7 16 "X ' Ethyl N-[(2-thioxo-1,2-dihy dropyridin-3-yl)carbo nyl]alaninate 18 T* Xy' Ethyl N-methyl-N-[(2-thiox o-1,2-dihydropyridin-3-yl)carbonyl]glycinat e 19 Ethyl N-[(2-thioxo-1,2-dihy dropyridin-3-yl)carbo nyljglycinate ethyl 20 1 (XTT N-[(2-thioxo-1,2-dihy dropyridin-3-yl)carbo nyljglycine 21 H N-methyl-N-[(2-thiox o-1,2-dihydropyridin-3-yl)carbonyl]glycine

[0240]

[0241]

[0242] Even more preferably, among these compounds, the following compounds are more particularly preferred: [Paintings?] No. Structure Chemical name CAS No. 18 AA A0 N-methyl-N-[(2-thiox o-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 19 # \ .. Y < jLaaaaaajv. -'•X / "m \ XU \ n N-methyl-N-[(2-thiox o-1,2-dihydropyridin-3-yl)carbonyl]glycine In a most preferred embodiment, the compound according to the present invention is as follows:

[0243] [Tables8] 20 jti ÇV T N-[(2-thioxo-1,2-dihy dropyridin-3-yl)carbo nyl]glycine

[0244] All of the above compounds can be obtained by a chemical process known to those skilled in the art, from commercially available reagents.

[0245] The thiopyridinone compound (1) may be prepared according to the process described, for example, in EP-A-3390363 or WO 2017 / 102349, which is incorporated herein by reference.

[0246] The thiopyridinone compound (1) may be an active ingredient or an active compound in cosmetic or dermatological products. The term "active" ingredient or compound used herein means an ingredient or compound that has an active cosmetic or dermatological property, such as antioxidant, whitening, UV filtering, and antibacterial effects. The thiopyridinone compound (1) used in the present invention may function as a depigmenting, bleaching, or bleaching agent, and thus the composition according to the present invention may be used as a bleaching product or as a cosmetic composition for bleaching a keratin material.

[0247] The thiopyridinone compound (1) can be used as an agent for depigmenting, bleaching or whitening the skin, body hair, eyelashes or hair, and also the lips and / or nails, and preferably the skin, in particular for removing pigmentation spots or aging spots, and / or as an anti-tanning agent.

[0248] The amount of the thiopyridinone compound(s) (1) in the composition according to the present invention may be 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.

[0249] Furthermore, the amount of the thiopyridinone compound(s) (1) in the composition according to the present invention may be 10% by weight or less, preferably 5% by weight or less, and more preferably 3% by weight or less, relative to the total weight of the composition.

[0250] The amount of the thiopyridinone compound(s) (1) in the composition according to the present invention may range from 0.01% to 10% by weight, preferably from 0.05% to 5% by weight, more preferably from 0.1% to 3% by weight, relative to the total weight of the composition.

[0251] (Vitamin B 3 )

[0252] Vitamin B3, also called vitamin PP, is a compound with the following formula:

[0253] where R may be -CONH2 (niacinamide), -COOH (nicotinic acid or niacin), or CH2OH (nicotinic alcohol), -CO-NH-CH2-COOH (nicotinuric acid), or -CO-NH-OH (niconityl hydroxamic acid). Niacinamide is preferred.

[0254] Vitamin B3 derivatives that may be cited include, for example, nicotinic acid esters such as tocopherol nicotinate, amides derived from niacinamide by substitution of the hydrogen groups of -CONH2, products resulting from a reaction with carboxylic acids and amino acids, esters of nicotinyl alcohol and carboxylic acids such as acetic acid, salicyclic acid, glycolic acid or palmitic acid.

[0255] The following derivatives may also be mentioned: 2-chloronicotinamide, 6-methylnicotinamide, 6-aminonicotinamide, N-methylnicotinamide, N,N-dimethylnicotinamide, N-(hydroxymethyl)nicotinamide, quinolinic acid imide, nicotinanilide, N-benzylnicotinamide, N-ethylnicotinamide, nifenazone, ni-cotinaldehyde, isonicotinic acid, methylisonicotinic acid, thionicotinamide, nialamide, 2-mercaptonicotinic acid, nicomol and niaprazine, methyl nicotinate and sodium nicotinate.

[0256] Other derivatives of vitamin B3 which may also be cited include its inorganic salts, such as chlorides, bromides, iodides or carbonates, and its organic salts, such as salts obtained by reaction with carboxylic acids, such as acetate, salicylate, glycolate, lactate, malate, citrate, mandelate, tartrate, etc.

[0257] In a preferred embodiment, the at least one compound selected from vitamin B3 and its derivatives (2) in the composition of the invention is a niacinamide.

[0258] The amount of the at least one compound selected from vitamin B3 and its derivatives (2) in the composition according to the present invention may be 0.06% by weight or more, preferably 0.3% by weight or more, and more preferably 0.6% by weight or more, relative to the total weight of the composition.

[0259] Furthermore, the amount of the at least one compound selected from vitamin B3 and its derivatives (2) in the composition according to the present invention may be 60% by weight or less, preferably 30% by weight or less, and more preferably 18% by weight or less, relative to the total weight of the composition.

[0260] The amount of at least one compound selected from vitamin B3 and its derivatives (2) in the composition according to the present invention can range from 0.06% to 60% in weight, preferably from 0.3% to 30% by weight, more preferably from 0.6% to 18% by weight, relative to the total weight of the composition.

[0261] The weight ratio of the amount of at least one compound selected from vitamin B3 and its derivatives (2) to the amount of the thiopyridinone compound(s) (1), in the composition according to the present invention, may be 6 or more, preferably 8 or more, and more preferably 10 or more.

[0262] The weight ratio of the quantity of at least one compound selected from vitamin B3 and its derivatives (2) to the quantity of the thiopyrolidone compound(s) (1), in the composition according to the present invention, may be less than or equal to 20, preferably less than or equal to 15, and more preferably less than or equal to 12.

[0263] The weight ratio of the quantity of at least one compound selected from vitamin B3 and its derivatives (2) to the quantity of the thiopyridinone compound(s) (1), in the composition according to the present invention, may range from 6 to 20, preferably from 8 to 15, and more preferably from 10 to 12.

[0264] (pH correction agent)

[0265] The composition according to the present invention may comprise (3) at least one pH correcting agent (pH corrector). Two or more pH correcting agents may be used in combination. Thus, a single type of pH correcting agent or a combination of different types of pH correcting agents may be used.

[0266] As pH correction agent (3), at least one agent may be used acidifying agent and / or at least one basifying agent (alkaline agent).

[0267] The acidifying agent may be a monovalent or polyvalent acid, such as divalent.

[0268] The 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.

[0269] The basifying agent may be a monovalent or polyvalent base, such as divalent.

[0270] Basifying agents can be mineral (inorganic) or organic, or hybrid.

[0271] The mineral basifying agents may be chosen 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.

[0272] The organic basifying agents may be chosen from organic amines whose pKb at 25°C is less than 12, preferably less than 10, and even more advantageously less than 6. It should be noted that this is the pKb corresponding to the function of greater basicity. Furthermore, organic amines do not include any alkyl or alkenyl fatty chains comprising more than ten carbon atoms.

[0273] The organic basifying agent may be chosen, for example, from alkanolamines, oxyethylenated and / or oxypropylenated ethylenediamines, amino acids and amine compounds of formula (III) below:

[0274] in which

[0275] W represents a divalent C1-C6 alkylene radical optionally substituted by one or more hydroxyl groups or a C1-C6 alkyl radical, and optionally interrupted by one or more heteroatoms such as O and N, and

[0276] Rx, Ry, Rz and Rt, which may be the same or different, represent a hydrogen atom or a C1-C6 alkyl, C1-C6 hydroxyalkyl, or C1-C6 aminoalkyl radical.

[0277] Examples of amine compounds of formula (III) which may be cited include 1,3-diaminopropane, 1,3-diamino-2-propanol, spermine and spermidine.

[0278] The term “alkanolamine” designates an organic amine comprising a primary, secondary or tertiary amine function, and one or more linear or branched CrC8 alkyl groups carrying one or more hydroxyl radicals.

[0279] Alkanolamines such as monoalkanolamines, dialkanolamines or trialkanolamines comprising one to three identical or different C1-C4 hydroxyalkyl radicals may be suitable for the present invention. Among the compounds of this type, mention may be made of monoethanolamine (MEA), diethanolamine, triethanolamine, monoisopropa-nolamine, diisopropanolamine, N-dimethylaminoethanolamine, 2-amino-2-methyl-1-propanol, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, 3-amino-1,2-propanediol, 3-dimethylamino-1,2-propanediol and tris(hydroxymethylamino)methane.

[0280] The amino acids which can be used are of natural or synthetic origin, in their L, D or racemic form, and comprise at least one acid function chosen more particularly from the carboxylic acid, sulfonic acid, phosphonic acid or phosphoric acid functions. The amino acids can be in neutral or ionic form.

[0281] As amino acids which may be used in the present invention, mention may in particular be made of aspartic acid, glutamic acid, alanine, arginine, omithine, ci-trulline, asparagine, carnitine, cysteine, glutamine, glycine, histidine, lysine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine and valine.

[0282] It may be preferable that the amino acids are basic amino acids comprising an additional amine function optionally included in a ring or in a ureido function.

[0283] Such basic amino acids may preferably be chosen from those corresponding to formula (IV) below:

[0284] in which

[0285] R represents a group chosen from:

[0286] -(CH2)3-NH2,

[0287] -(CH2)2-NH2,

[0288] -(CH2)2-NH-CO-NH2, and

[0289] Compounds corresponding to formula (IV) include histidine, lysine, arginine, ornithine and citrulline.

[0290] The organic basifying agent may be chosen from organic amines of heterocyclic type. In addition to histidine, which has already been mentioned in the amino acids, mention may in particular be made of pyridine, piperidine, imidazole, triazole, tetrazole and benzimidazole.

[0291] The organic basifying agent may also be chosen from amino acid dipeptides. As amino acid dipeptides which may be used in the present invention, mention may in particular be made of carnosine, anserine and balein.

[0292] The organic basifying agent may also be chosen from compounds comprising a guanidine function. As amines of this type which may be used in the present invention, in addition to arginine, which has already been mentioned as an amino acid, mention may in particular be made of creatine, creatinine, 1,1-dimethylguanidine, 1,1-diethylguanidine, glycocyamine, metformin, agmatine, N-amidinoalanine, 3-guanidinopropionic acid, 4-guanidinobutyric acid and 2-([amino(imino)methyl]amino)ethane-l-sulfonic acid.

[0293] In a preferred embodiment of the present invention, the organic basifying agent may be selected from amino acids, preferably basic amino acids, and more preferably arginine, lysine, histidine or mixtures thereof. Even more preferably, the organic basifying agent may be arginine.

[0294] Hybrid compounds that may be cited include salts of the aforementioned amines with acids such as carbonic acid or hydrochloric acid. Guanidine carbonate or monoethanolamine hydrochloride may in particular be used.

[0295] The pH correcting agent (3) 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, based on the total weight of the composition.

[0296] The pH correcting agent (3) 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.

[0297] The pH correcting agent (3) may be present in an amount ranging 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.

[0298] It is preferable that the composition according to the present invention has a pH of 4.5 or higher, and more preferably 5 or higher.

[0299] It is preferable that the composition according to the present invention has a pH of 6.5 or less, and more preferably 6 or less.

[0300] 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 to 6.

[0301] The pH of the composition means the pH of the aqueous phase of the composition according to the present invention.

[0302] It may be preferable that at least one buffer or buffering agent is also used, such as the pH correcting agent (3), in combination with the acidifying agent and / or the basifying agent, in order to stabilize the pH of the composition according to the present invention.

[0303] As the buffer, any of the commonly known buffers 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 the buffer, if citric acid or lactic acid is used as the acidifying agent.

[0304] (Water)

[0305] The composition according to the present invention may comprise (4) water.

[0306] The amount of water (4) in the composition according to the present invention may be 50% by weight or more, preferably 55% by weight or more, and more preferably 60% by weight or more, relative to the total weight of the composition.

[0307] Furthermore, the amount of water (4) in the composition according to the present invention may be 99% by weight or less, preferably 95% by weight or less, and more preferably 90% by weight or less, relative to the total weight of the composition.

[0308] The amount of water (4) in the composition according to the present invention may be from 50% to 99% by weight, preferably from 55% to 95% by weight, and more preferably from 60% to 90% by weight, relative to the total weight of the composition.

[0309] (Caffeine)

[0310] In a particular embodiment of the invention, the composition according to the present invention may further comprise (5) caffeine.

[0311] Caffeine (5) may be present in an amount of 0.01% by weight or more, preferably 0.5% by weight or more, and more preferably 1% by weight or more, based on the total weight of the composition.

[0312] Caffeine (5) 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, based on the total weight of the composition.

[0313] Caffeine (5) may be present in an amount ranging from 0.01% to 15% by weight, preferably from 0.5% to 10% by weight, and more preferably from 1% to 5% by weight or less, relative to the total weight of the composition.

[0314] In a particular embodiment of the invention, the composition of the invention comprises (1) a thiopyridinone compound as disclosed above, (2) at least one compound selected from vitamin B3 and its derivatives and (3) caffeine.

[0315] (Other optional additives)

[0316] The composition according to the present invention may also comprise any other optional additive(s) usually used in the field of cosmetics, chosen, for example, from solvents, chelating agents, cosmetic active agents other than ingredient (1), such as oils, preservatives, and mixtures thereof.

[0317] It is part of the ordinary operations for those skilled in the art to adjust the nature and quantity of the above optional additives which may be present in the composition according to the present invention in such a way that the desired cosmetic properties are not affected thereby.

[0318] As solvents, mention may be made of one or more cosmetically acceptable organic solvents, which may be alcohols: in particular monovalent alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol; diols such as ethylene glycol, propylene glycol and butylene glycol; other polyols such as glycerol, sugar and sugar alcohols; and ethers such as ethylene glycol monomethyl, monoethyl and monobutyl ethers, propylene glycol monomethyl, monoethyl and monobutyl ethers, and butylene glycol monomethyl, monoethyl and monobutyl ethers.

[0319] The 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.

[0320] [Preparation]

[0321] The composition according to the present invention can be prepared by mixing the essential and optional ingredients described above in a conventional manner.

[0322] For example, the composition according to the present invention can be prepared by a process comprising the steps of

[0323] mixture

[0324] (1) at least one thiopyridinone compound; and

[0325] (2) of at least one compound selected from vitamin B3 and its derivatives.

[0326] It is possible to further mix any of the optional ingredients.

[0327] The mixing can be carried out at any temperature such as room temperature (e.g., 20-25°C, preferably 25°C), preferably at a temperature of 30°C or higher, preferably 40°C or higher, and more preferably 50°C or higher.

[0328] The form of the composition according to the present invention is not particularly limited, and may take various forms such as a W / O emulsion, an O / W emulsion, a gel, a solution, or the like. It is preferable that the composition according to the present invention is in the form of an emulsion, preferably an O / W emulsion, and more preferably, an O / W gel emulsion or a gel.

[0329] [Cosmetic process]

[0330] The composition according to the present invention can be used as a cosmetic or dermatological composition, preferably as a cosmetic composition and more preferably, as a cosmetic composition for a keratin material. As keratin material, mention may be made of the skin, the scalp, the hairs, the mucous membranes such as the lips, and the nails.

[0331] The composition according to the present invention can be used as a depigmentation, bleaching or bleaching product for a keratin material such as the skin. In particular, the composition according to the present invention can be used as a bleaching product.

[0332] The composition according to the present invention may preferably be intended for application to a keratin material such as the skin, the scalp and / or the lips, preferably the skin.

[0333] Thus, the composition according to the present invention can be used for a cosmetic process for a keratin material, preferably the skin. In one embodiment, the present invention relates to a cosmetic process, preferably a bleaching process, for a keratin material, preferably the skin, comprising the step of applying to the keratin material the composition according to the present invention.

[0334] The composition according to the present invention can be used as a topical cosmetic composition in the form of a lotion, a milky lotion, a cream, a gel, a paste, a serum, a mousse or a spray.

[0335] [Use]

[0336] The present invention also relates to a use of at least one compound selected from vitamin B3 and its derivatives (2) in a composition comprising at least one compound (1) chosen from the compounds of formula (I) below, the tautomers of formula (!') below, their salts, solvates, such as their hydrates, their optical isomers, their racemates, and their mixtures:

[0337] in which

[0338] Ri denotes a radical chosen from

[0339] a) a hydrogen atom, and

[0340] b) a linear C1-C10 or branched C3-C10 saturated alkyl group optionally substituted by one or more groups, which may be the same or different, chosen from

[0341] i) -O-R3, and

[0342] ii) -S-R3,

[0343] and

[0344] R2 denotes a radical chosen from

[0345] a) a hydrogen atom,

[0346] b) a linear or branched C3-Ci2 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, which may be the same or different, chosen from

[0347] i) -O-R3,

[0348] ii) -S-R3,

[0349] iii) -C(O)-O-R3, and

[0350] iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals and

[0351] c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals

[0352] in which

[0353] R3 denotes a radical chosen from

[0354] a) a hydrogen atom, and

[0355] b) a linear C1-C10 or branched C3-C10 saturated alkyl group

[0356] in order to solubilize the compound(s) (1).

[0357] The term “solubilize” has the same meaning as enhance solubility.

[0358] The use according to the present invention can increase the solubility of the thiopyridinone compound (1) in the composition comprising it. The resulting composition is therefore not cloudy. The increased solubility of the thiopyridinone compound (1) in the composition of the invention therefore makes this composition stable and transparent.

[0359] The above explanations concerning the thiopyridinone compound (1) and the at least one compound selected from vitamin B3 and its derivatives (2) for the compositions according to the present invention can also be applied to those used in the use according to the present invention.

[0360] The composition in the use according to the present invention may include any of the optional ingredients as explained above for the compositions according to the present invention. EXAMPLES

[0361] The present invention will be described in more detail with the aid of examples. However, these examples should not be construed as limiting the scope of the present invention. [Examples 1 to 3 and comparative examples 1 and 2]

[0362] [Preparation]

[0363] Each of the compositions according to Examples 1 to 3 and Comparative Examples 1 and 2 was prepared by mixing the ingredients listed in Table 1. The numerical values ​​for the amounts of the ingredients are all based on "% by weight" as active ingredients.

[0364] A screening test was carried out with niacinamide, or with niacinamide and caffeine in order to evaluate the solubilization of the thiopyridinone compound 20 according to the invention. In this test, the thiopyridinone compound 20 was mixed with niacinamide, in association with the raw materials disclosed in Examples 1 to 3 or Comparative Examples 1 and 2, at room temperature using a stirrer. magnetic and observed for the next 90 minutes.

[0365] The appearance of the mixtures was analyzed, looking for suspended or settled particles and a comparison with the pure thiopyridinone compound 20 was made.

[0366] [Tables 1] Ingredients Ex. comp. 1 Ex. 1 Ex. comp. 2 Ex 2 Ex. 3 Water qsplOO qsplOO qsplOO qsplOO qsplOO N-[(2-thioxo-l,2-dihyd ropyridin-3-yl)carbony l]glycine 0.5 0.5 1 1 1 Niacinamide 3 5 5 10 Caffeine 1 cloudy Transparent cloudy Transparent Transparent

[0367] Comparative examples 1 and 2 did not present a homogeneous appearance (turbidity) after the solubilization protocol.

[0368] As regards examples 1 to 3, the composition had a homogeneous and transparent appearance.< / k>

Claims

1. Claims Composition, preferably cosmetic composition, comprising (1) at least one compound selected 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: in which Ri denotes a radical chosen from a) a hydrogen atom, and (b) a linear C1-C10 or branched C3-C10 saturated alkyl group 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 C1-C12 or branched C3-C12 or cyclic C3-C8 saturated hydrocarbon group 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-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals and (c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals in which R3 denotes a radical chosen from a) a hydrogen atom, and (b) a linear or branched C1-C10 saturated alkyl group; and (2) at least one compound selected from vitamin B3, the weight ratio of the amount of the at least one compound selected from vitamin B3 (2) to the amount of the thiopyridinone compound(s) (1) being 6 or more.

2. A composition according to claim 1, wherein: Ri of formula (I) and (!') represents a hydrogen atom; Or Ri of formula (I) and (!') represents a linear (C1-C10) alkyl group or a branched (C3-C10) alkyl group, in particular a linear (C1-C6) alkyl group or a 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 not substituted; R2 of formula (I) and (!') represents a hydrogen atom; or 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 of R2 being unsubstituted; and R3 of formula (I) and (!') represents a hydrogen atom; or R3 of formula (I) and (!') represents a linear C1-C10 or branched C3-C10 saturated alkyl group; in particular a linear (C1-C6) alkyl group or a branched (C3-C6) alkyl group, preferably a (C1-C4) alkyl group such as the methyl group.

3. A composition according to claim 1 or 2, wherein: R2 of formula (I) and (!') represents a linear (C1-C10) alkyl group or a branched (C3-C10) alkyl group, in particular a linear (C1-C6) alkyl group or a 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) such as carboxy.

4. Composition according to any one of claims 1 to 3, in which: R 1 of formula (I) and (!') represents a radical chosen from a) a hydrogen atom, and b) a linear saturated C 1 -C 6 or C 3 -C 6 branched alkyl group optionally substituted by one or more groups, which may be the same or different, chosen from i) -O-R 3, and ii) -S-R 3, preferably optionally substituted by one or more groups i);R2 of formula (I) and (!') represents a radical chosen from a) a hydrogen atom, and b) a linear C1-C10 or branched C3-C10 or cyclic C3-C8 as well as C5-C6 saturated hydrocarbon group, 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 phenyl group optionally substituted by one or more hydroxyls and / or by one or more C1-C4 alkoxy radicals such as methoxy, preferably substituted by one or more groups selected from i) and iii), preferably iii) such as carboxy;and R3 of formula (I) and (!') represents a radical chosen from a) a hydrogen atom, and b) a linear C1-C6 or branched C3-C6 saturated alkyl group, preferably, the compounds of formula (I) and the tautomer (!'), their salts, solvates, such as their hydrates, their optical isomers, their racemates, and their mixtures, have the following meanings: R1 of formula (I) and (!') represents a radical chosen from: a) a hydrogen atom, and b) a linear C1-C4 or branched C3-C4 saturated alkyl group optionally substituted by one or more groups, which may be the same or different, chosen from i) -OR3jmore preferably unsubstituted; R2 of formula (I) and (!') represents a radical chosen from; a) a hydrogen atom, and b) a linear C1-C10 or branched C3-C10 or cyclic C3-C8 or C5-C6 saturated hydrocarbon group, optionally substituted by one or more groups, which may be the same or different, chosen from i) -O-R3, iii) -C(O)-O-R3, and iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more C1-C4 alkoxy radicals; and R3 of formula (I) and (!') represents a radical chosen from: a) a hydrogen atom; b) a saturated linear C1-C4 or branched C3-C4 alkyl group such as methyl or ethyl.

5. A composition according to any one of claims 1 to 4, wherein: compound (1) is selected from compounds 1 to 24 below, their tautomers, their salts, their solvates, such as their hydrates, their optical isomers, their racemates, and their mixtures, in particular compounds 1, 2, 4, 6, 7, 9, 11, 12, 14, 15, 16, 17, 18, 19, 20 or 21, more particularly 1, 9, 16, 18, 19, 20 or 21, preferably 18, 19, 20 or 21, and more preferably 20: [Tables 9] No. Structure Chemical name 1 A 'CM. H - H N-ethyl-2-thioxo-1,2-dihydro pyridine-3-carboxamide 2 / / / x \ yx\ x'_ N-methyl-2-thioxo-1,2-dihydro opyridine-3-carboxamide 3 N-octyl-2-thioxo-1,2-dihydro pyridine-3-carboxamide 4 h N-benzyl-2-thioxo-1,2-dihydr opyridine-3-carboxamide 5 / ;—w-—y ' N-phényl-2-thioxo-1,2-dihydr opyridine-3-carboxamide 6 Il [ H N-cyclohexyl-2-thioxo-1,2-di hy dropyridine- 3 -c arboxamide 7 _ i £jr Q?......" N- [2- (4-méthoxyphény l)éthy 1 ] -2-thioxo-1,2-dihydropyridin e-3-carboxamide 8 i H h .>x. :3 Ç? N-(2-méthylpropyl)-2-thioxo-1,2-dihydropyridine-3-carbox amide 9 H: $ H N-pentyl-2-thioxo-1,2-dihydr opyridine-3-carboxamide 10 O K ï f N-nonyl-2-thioxo-1,2-dihydro pyridine-3-carboxamide 11 G h "oh 'V' x’s H N-(2-hydroxyéthyl)-2-thioxo-1,2-dihydropyridine-3-carbox amide 12 K i \ 4> k ""CHs H N,N-diéthyl 2-mercaptonicotinamide 13 —K k .4-- 4 '"'-"-ÇJH Hf" :- xœ. N-éthyl-N-(2-hydroxyéthyl)-2 -thioxo-1,2-dihydropyridine-3 -carboxamide 14 î i[ * N-(2,3-dihydroxypropyl)-2-th ioxo-1,2-dihydropyridine-3-c arboxamide 15 ..CM Û P ^-x ,P A N- ( 1,3 -dihy droxypropan-2- y 1) -2-thioxo-1,2-dihydropyridine -3-carboxamide 16 H “ / N- [(2-thioxo-1,2-dihydropyri din-3-yl)carbonyl]alaninate d'éthyle 17 î J -.....T N- [(2-thioxo-1,2-dihydropyri din-3-yl)carbonyl]phenyl ethyl alaninate 18 OM : N-methyl-N- [(2-thioxo-1,2-di hydropyridin-3-yl)carbonyl]gl ycinate ethyl 19 H N- [(2-thioxo-1,2-dihydropyri din-3-yl)carbonyl]glycinate ethyl 20 JK î* N- [(2-thioxo-1,2-dihydropyri din-3-yl)carbonyl]glycine 21 U 1 ...... / / / k \= / N-methyl-N- [(2-thioxo-1,2-di hydropyridin-3-yl)carbonyl]gl ycine 22 > x X % ..^-. ..-'K .---^ v>f"" xpf-' N,N-bis(2-hydroxyethyl)-2-th ioxo-1,2-dihydropyridine-3-c arboxamide 23 ■-y N-(3-methoxypropyl)-2-thiox o-1,2-dihydropyridine-3-carb oxamide

6.

7.

8.

9.

10. 24 y N-butyl-2-thioxo-1,2-dihydro pyridine-3-carboxamide A composition according to any one of claims 1 to 5, wherein the amount of compound(s) (1) in the composition is from 0.01% to 10% by weight, preferably from 0.05% to 5% by weight, and more preferably from 0.1% to 3% by weight, relative to the total weight of the composition. A composition according to any one of claims 1 to 6, wherein the amount of the at least one compound selected from vitamin B3 (2) in the composition is from 0.06% to 60% by weight, preferably from 0.3% to 30% by weight, and more preferably from 0.6% to 18% by weight, relative to the total weight of the composition. A composition according to any one of claims 1 to 7, wherein the composition is used for bleaching a keratinous substance, preferably the skin. Cosmetic process, preferably a bleaching process, for a keratin material, preferably the skin, comprising the following step: application to the keratin material of the composition according to any one of claims 1 to 8. Use of at least one compound selected from vitamin B3 (2) in a composition comprising at least one compound (1) 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: in which Ri denotes a radical chosen from a) a hydrogen atom, and b) a saturated linear C1-C10 or branched C3-C10 alkyl group optionally tively 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 C1-C12 or branched C3-C12 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, which may be the same or different, chosen from i) -O-R3, ü) -S-R3, iii) -C(O)-O-R3, and iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals and (c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals in which R3 denotes a radical chosen from a) a hydrogen atom, and b) a linear C1-C10 or branched C3-C10 saturated alkyl group in order to solubilize the compound(s) (1).