Stabilization of thiopyridinone compounds and compositions comprising same

Abstract

The present invention relates to a composition comprising: (1) at least one thiopyridone compound; and (2) at least one chelating agent. The present invention can provide a composition comprising (1) thiopyridone compound (s), the stability of the (1) thiopyridone compound (s) of the composition being increased over time, particularly even when the composition is maintained for a relatively long period of time at high temperatures.

Description

Technical Field

[0001] The present invention relates to the stabilization of thiopyridone compounds in compositions comprising the thiopyridone compounds. Background Art

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

[0003] For the purpose of treating pigmented spots, it is particularly desirable to use a harmless topical depigmenting substance with good efficacy.

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

[0005] On the other hand, WO2017 / 102349 discloses a new decolorizing agent or whitening agent, namely a thiopyridone compound. The thiopyridone compound can exhibit a strong decolorizing or whitening effect by reducing the production of melanin.

[0006] Invention Disclosure

[0007] However, it has been found that thiopyridone compounds tend to become destabilized in compositions over time, particularly when compositions comprising thiopyridone compounds are maintained at elevated temperatures for relatively long periods of time.

[0008] It is therefore an object of the present invention to provide a composition comprising one or more thiopyridone compounds having an improved stability of the one or more thiopyridone compounds over time, in particular when the composition is kept at elevated temperature for a relatively long period of time.

[0009] The above objects can be achieved by a composition comprising:

[0010] (1) at least one compound selected from the group consisting of a compound of the following formula (I), a tautomer of the following formula (I'), a salt thereof, a solvate thereof such as a hydrate, an optical isomer thereof, a racemate thereof, and a mixture thereof:

[0011]

[0012] in

[0013] R1 is a group selected from the following

[0014] a) hydrogen atoms, and

[0015] b) Saturated straight chain C1-C 10 or branched C3-C10 Alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0016] i)-O-R3, and

[0017] ii) -S-R3,

[0018] and

[0019] R2 is a group selected from the following

[0020] a) Hydrogen atoms,

[0021] b) Saturated straight chain C1-C 12 or branched C3-C 12 or a cyclic C3-C8 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0022] i) -O-R3,

[0023] ii) -S-R3,

[0024] iii) -C(O)-O-R3, and

[0025] iv) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups, and

[0026] c) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups,

[0027] in

[0028] R3 is a group selected from the following

[0029] a) hydrogen atoms, and

[0030] b) Saturated straight chain C1-C 10 or branched C3-C 10 alkyl;

[0031] and

[0032] (2) At least one chelating agent.

[0033] It may be preferred that:

[0034] R1 in formula (I) and (I') represents a hydrogen atom;

[0035] or

[0036] R1 in formula (I) and (I') represents a straight chain (C1-C10 ) alkyl or branched (C3-C 10 )alkyl, especially linear (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl, especially the alkyl of R1 is unsubstituted.

[0037] It may be preferred that:

[0038] R2 in formula (I) and (I') represents a hydrogen atom;

[0039] or

[0040] R2 in formula (I) and (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially straight-chain (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; the alkyl of R2 is unsubstituted.

[0041] It may be preferred that:

[0042] R2 in formula (I) and (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially straight-chain (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; the alkyl is substituted by one or more groups selected from i), ii), iii) and iv) as defined above, preferably the alkyl is substituted by one or two groups selected from i), ii) and iii), more preferably substituted by one or two groups selected from i) and iii), better substituted by a group iii) such as carboxyl.

[0043] It may be preferred that:

[0044] R2 in formula (I) and (I') represents a (C3-C8) cycloalkyl group, preferably a (C5-C7) cycloalkyl group such as a cyclohexyl group;

[0045] or

[0046] R2 in formula (I) and (I') represents a C5-C8 alkoxyl group optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxyl groups. 12 Aryl is preferably, in particular, unsubstituted phenyl.

[0047] It may be preferred that:

[0048] R3 in formula (I) and (I') represents a hydrogen atom;

[0049] or

[0050] R3 in formula (I) and (I') represents a saturated straight chain C1-C 10 or branched C3-C 10 Alkyl, in particular straight chain (C1-C6) alkyl or branched chain (C3-C6) alkyl, preferably (C1-C4) alkyl such as methyl.

[0051] It may be preferred that:

[0052] R1 in formula (I) and (I') represents a group selected from the following

[0053] a) hydrogen atoms, and

[0054] b) saturated straight-chain C1-C6 or branched C3-C6 alkyl groups, which are optionally substituted by one or more groups, which may be the same or different, and are selected from

[0055] i)-O-R3, and

[0056] ii) -S-R3,

[0057] Preferably optionally substituted with one or more groups i);

[0058] R2 in formula (I) and (I') represents a group selected from the following

[0059] a) hydrogen atoms, and

[0060] b) Saturated straight chain C1-C 10 or branched C3-C 10 or a cyclic C3-C8 such as C5-C6 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -O-R3,

[0061] ii) -S-R3,

[0062] iii) -C(O)-O-R3, and

[0063] iv) phenyl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C4 alkoxy groups such as methoxy,

[0064] Preferably substituted with one or more groups selected from i) and iii), preferably iii), such as carboxyl; and

[0065] R3 in formula (I) and (I') represents a group selected from the following

[0066] a) hydrogen atoms, and

[0067] b) saturated straight-chain C1-C6 or branched C3-C6 alkyl groups,

[0068] Preferably, the compounds of formula (I) and tautomers (I'), their salts, their solvates such as hydrates, their optical isomers, their racemates and mixtures thereof have the following meanings:

[0069] R1 in formula (I) and (I') represents a group selected from the following

[0070] a) hydrogen atoms, and

[0071] b) saturated straight-chain C1-C4 or branched C3-C4 alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -OR3, more preferably unsubstituted;

[0072] R2 in formula (I) and (I') represents a group selected from the following

[0073] a) hydrogen atoms, and

[0074] b) Saturated straight chain C1-C 10 or branched C3-C 10 or a cyclic C3-C8 such as C5-C6 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -O-R3,

[0075] iii) -C(O)-O-R3, and

[0076] iv) C5-C 12 Aryl, which is optionally substituted with one or more hydroxyl groups and / or one or more C1-C4 alkoxy groups; and

[0077] R3 in formula (I) and (I') represents a group selected from the following

[0078] a) Hydrogen atom;

[0079] b) Saturated straight-chain C1-C4 or branched C3-C4 alkyl groups, such as methyl or ethyl.

[0080] (1) The compound may be selected from the following compounds 1 to 24, their tautomers, their salts, their solvates such as hydrates, their optical isomers, their racemates and mixtures thereof, in particular compound 1, 2, 4, 6, 7, 9, 11, 12, 14, 15, 16, 17, 18, 19, 20 or 21, more in particular 1, 9, 16, 18, 19, 20 or 21, preferably 18, 19, 20 or 21, and more preferably 20:

[0081]

[0082]

[0083]

[0084]

[0085] The amount of (1) compound(s) in the composition according to the 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.

[0086] (2) The chelating agent may be selected from organic chelating agents, preferably aminocarboxylic acids and salts thereof, hydroxycarboxylic acids and salts thereof, and mixtures thereof, and more preferably aminocarboxylic acids and salts thereof.

[0087] (2) The chelating agent may be selected from EDTA and its salts, citric acid and its salts, N,N-bis(carboxymethyl)-L-glutamic acid and its salts, metaphosphates and mixtures thereof.

[0088] (2) The chelating agent may be selected from succinic acid derivatives, such as ethylenediamine disuccinic acid and its salts.

[0089] (2) The amount of the (one or more) chelating agents in the composition according to the invention may be 0.01% to 3% by weight, preferably 0.05% to 2% by weight, more preferably 0.1% to 1% by weight, relative to the total weight of the composition.

[0090] Another aspect of the present invention is the use of (2) at least one chelating agent in a composition comprising (1) at least one compound selected from the group consisting of a compound of the following formula (I), a tautomer of the following formula (I'), a salt thereof, a solvate thereof such as a hydrate, an optical isomer thereof, a racemate thereof, and a mixture thereof:

[0091]

[0092] in

[0093] R1 is a group selected from the following

[0094] a) hydrogen atoms, and

[0095] b) Saturated straight chain C1-C 10 or branched C3-C 10 Alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0096] i)-O-R3, and

[0097] ii) -S-R3,

[0098] and

[0099] R2 is a group selected from the following

[0100] a) Hydrogen atoms,

[0101] b) Saturated straight chain C1-C 12 or branched C3-C 12 or a cyclic C3-C8 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0102] i) -O-R3,

[0103] ii) -S-R3,

[0104] iii) -C(O)-O-R3, and

[0105] iv) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups, and

[0106] c) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups,

[0107] in

[0108] R3 is a group selected from the following

[0109] a) hydrogen atoms, and

[0110] b) Saturated straight chain C1-C 10 or branched C3-C 10 alkyl

[0111] To stabilize (1) (one or more) compounds.

[0112] In another embodiment of this use, (2) the chelating agent can be selected from succinic acid derivatives, such as ethylenediamine disuccinic acid and its salts

[0113] Best Mode for Carrying Out the Invention

[0114] After diligent research, the present inventors have discovered that it is possible to provide compositions comprising a thiopyridone compound or compounds having improved stability of the thiopyridone compound or compounds over time, particularly when the composition is maintained at elevated temperatures for relatively long periods of time.

[0115] Therefore, the composition according to the invention comprises:

[0116] (1) at least one compound selected from the group consisting of a compound of the following formula (I), a tautomer of the following formula (I'), a salt thereof, a solvate thereof such as a hydrate, an optical isomer thereof, a racemate thereof, and a mixture thereof (hereinafter, the compound is referred to as a "thiopyridone compound"):

[0117]

[0118] in

[0119] R1 is a group selected from the following

[0120] a) hydrogen atoms, and

[0121] b) Saturated straight chain C1-C 10 or branched C3-C 10 Alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0122] i)-O-R3, and

[0123] ii) -S-R3,

[0124] and

[0125] R2 is a group selected from the following

[0126] a) Hydrogen atoms,

[0127] b) Saturated straight chain C1-C 12 or branched C3-C 12 or a cyclic C3-C8 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0128] i) -O-R3,

[0129] ii) -S-R3,

[0130] iii) -C(O)-O-R3, and

[0131] iv) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups, and

[0132] c) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups,

[0133] in

[0134] R3 is a group selected from the following

[0135] a) hydrogen atoms, and

[0136] b) Saturated straight chain C1-C 10 or branched C3-C 10 alkyl;

[0137] and

[0138] (2) At least one chelating agent.

[0139] The composition according to the present invention may exhibit improved stability of the (1) thiopyridone compound therein.

[0140] In other words, the composition according to the present invention can improve the stability of the (1) thiopyridone compound therein. The term "stability" of the (1) thiopyridone compound can be determined by the change in the amount of the (1) thiopyridone compound in the composition according to the present invention over a certain period of time. Improved "stability" means that the amount of the (1) thiopyridone compound changes more limitedly over time.

[0141] The composition according to the present invention can exhibit improved stability of the (1) thiopyridone compound therein even when the composition is kept at an elevated temperature, such as 55° C., for a relatively long period of time, such as two weeks.

[0142] Thus, the composition according to the invention can be stored for a long time, even under hot conditions.

[0143] Furthermore, the increased stability of the (1) thiopyridone compound may provide improved or enhanced bioavailability of the (1) thiopyridone compound which may act as a depigmenting or whitening agent. Thus, the composition according to the present invention may provide an enhanced or improved depigmenting or whitening effect.

[0144] The composition, use, etc. according to the present invention will be described below in a detailed manner.

[0145] [Composition]

[0146] The composition according to the invention comprises:

[0147] (1) at least one thiopyridone compound; and

[0148] (2) At least one chelating agent.

[0149] The (1) thiopyridone compound and (2) chelating agent, as well as other features of the composition according to the present invention will be explained below.

[0150] (Thiopyridone compounds)

[0151] The composition according to the present invention comprises (1) at least one thiopyridone compound. Two or more (1) thiopyridone compounds may be used in combination. Thus, a single type of (1) thiopyridone compound or a combination of different types of (1) thiopyridone compounds may be used.

[0152] (1) The thiopyridone compound is selected from the group consisting of a compound of the following formula (I), a tautomer of the following formula (I'), a salt thereof, a solvate thereof such as a hydrate, an optical isomer thereof, a racemate thereof, and a mixture thereof:

[0153]

[0154] in

[0155] R1 is a group selected from the following

[0156] a) hydrogen atoms, and

[0157] b) Saturated straight chain C1-C 10 or branched C3-C 10 Alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0158] i)-O-R3, and

[0159] ii) -S-R3,

[0160] and

[0161] R2 is a group selected from the following

[0162] a) Hydrogen atoms,

[0163] b) Saturated straight chain C1-C 12 or branched C3-C 12 or a cyclic C3-C8 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0164] i) -O-R3,

[0165] ii) -S-R3,

[0166] iii) -C(O)-O-R3, and

[0167] iv) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups, and

[0168] c) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups,

[0169] in

[0170] R3 is a group selected from the following

[0171] a) hydrogen atoms, and

[0172] b) Saturated straight chain C1-C 10or branched C3-C 10 alkyl.

[0173] Hereinafter, for the purpose of the present invention and unless otherwise specified:

[0174] - "Saturated straight chain C1-C 12 or branched C3-C 12 "Hydrocarbon is equivalent to "straight chain (C1-C 12 ) alkyl or branched (C3-C 12 ) alkyl", which corresponds to a saturated straight-chain C1-C 12 or branched C3-C 12 Hydrocarbon-based groups, preferably straight-chain C1-C 10 or branched C3-C 10 A hydrocarbon-based group, and more preferably a straight-chain C1-C6 or branched C3-C6 hydrocarbon-based group; preferably, the straight-chain or branched group may be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl. More preferably, a saturated straight-chain or branched alkyl group may be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl and octyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl;

[0175] - saturated "cyclic C3-C8" hydrocarbon radical is a monocyclic or bicyclic cycloalkyl radical containing 3 to 8 carbon atoms, and especially a monocyclic cycloalkyl radical in C5 to C7, such as cyclohexyl,

[0176] - "Alkoxy group" is an alkyl-oxy group in which the alkyl group is a straight or branched C1-C 16 , and preferably a C1-C8 hydrocarbon-based group;

[0177] - when alkoxy is optionally substituted, this means that alkyl is optionally substituted as defined above;

[0178] - "aryl" means a fused or non-fused monocyclic or bicyclic carbon-based group containing 5 to 12 carbon atoms, preferably 6 to 10 carbon atoms, and wherein at least one ring is aromatic; preferably, the aryl group is phenyl, biphenyl, naphthyl, more preferably phenyl;

[0179] - the term "at least one" is equivalent to the term "one or more"; and

[0180] - The term "inclusive" used for a range of concentrations means that the limits of the range are included in the defined range.

[0181] Salts of compounds of formula (I), (I'), (II) or (II') as defined below include conventional non-toxic salts of said compounds, such as salts formed from organic or inorganic acids or from organic or inorganic bases.

[0182] As salts of the compounds of formula (I), (I'), (II) or (II'), mention may be made of:

[0183] A salt obtained by adding a compound of formula (I) or (II) to:

[0184] - salts obtained by addition of inorganic bases, for example sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide and sodium, potassium or calcium carbonates or hydrogencarbonates;

[0185] or

[0186] - an organic base, for example a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine. The primary, secondary or tertiary alkylamine may contain one or more nitrogen and / or oxygen atoms and may therefore contain, 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-propylene glycol and 3-(dimethylamino)propylamine.

[0187] Mention may also be made of the salts of amino acids, for example lysine, arginine, guanidine, glutamic acid and aspartic acid. Advantageously, the salts of the compounds of formula (I) or (II) when they contain a carboxyl group may be chosen from alkali metal salts or alkaline earth metal salts, such as sodium, potassium, calcium or magnesium salts and ammonium salts.

[0188] As "organic or inorganic acid salt" is more particularly selected from the following salts: selected from salts 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 acid: Alk-OS(O)OH, such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acid, such as tolyloxysulfinic acid and phenoxysulfinic acid; xii) phosphoric acid H3PO4; xiii) acetic acid CH3C(O)OH; xiv) trifluoromethanesulfonic acid CF3SO3H; and xv) tetrafluoroborate HBF4.

[0189] Acceptable solvates of the compounds described in the specification include conventional solvates such as those formed during the preparation of the compounds due to the presence of solvents. For example, solvates due to the presence of water or linear or branched alcohols such as ethanol or isopropanol can be mentioned.

[0190] Optical isomers are in particular enantiomers and diastereomers.

[0191] When a tautomeric equilibrium exists according to the following scheme, compound (I') is a tautomeric form of compound (I):

[0192]

[0193] According to one embodiment of the invention, R1 represents a hydrogen atom.

[0194] According to another embodiment of the present invention, R1 represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially straight chain (C1-C6)alkyl or branched chain (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl. In particular, the alkyl of R1 is unsubstituted.

[0195] According to one embodiment of the invention, R2 represents a hydrogen atom.

[0196] According to another embodiment of the present invention, R2 represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially straight-chain (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; the alkyl of R2 is unsubstituted.

[0197] According to another embodiment of the present invention, R2 represents a straight chain (C1-C 10 )alkyl or branched (C3-C10)alkyl, especially straight (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; the alkyl is substituted by one or more groups selected from i), ii), iii) and iv) as defined above. Preferably, the alkyl is substituted by one or two groups selected from i), ii) and iii), more preferably by one or two groups selected from i) and iii), more preferably by a group iii) which is a carboxyl group.

[0198] Another variant of the radical R2 is that the alkyl radical is substituted by a radical iv), in particular by a phenyl radical.

[0199] According to another embodiment of the present invention, R2 represents a (C3-C8)cycloalkyl group, preferably a (C5-C7)cycloalkyl group such as cyclohexyl.

[0200] According to another embodiment of the present invention, R2 represents a C5-C8 alkoxyl group optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups. 12 Aryl, in particular unsubstituted phenyl, is preferred.

[0201] According to one embodiment, R3 represents a hydrogen atom.

[0202] According to another embodiment, R3 represents a saturated linear C1-C 10 or branched C3-C 10 Alkyl; in particular straight-chain (C1-C6) alkyl or branched (C3-C6) alkyl, preferably (C1-C4) alkyl such as methyl.

[0203] Preferably, the compound of formula (I) and the tautomer (I') or a salt thereof, an optical isomer thereof, and a racemate and / or a solvate thereof (such as a hydrate), alone or as a mixture

[0204] Has the following meanings:

[0205] R1 is a group selected from the following

[0206] a) hydrogen atoms, and

[0207] b) saturated straight-chain C1-C6 or branched C3-C6 alkyl groups, which are optionally substituted by one or more groups, which may be the same or different, and are selected from

[0208] i)-O-R3, and

[0209] ii) -S-R3,

[0210] Preferably optionally substituted with one or more groups i);

[0211] R2 is a group selected from the following

[0212] a) Hydrogen atoms,

[0213] b) Saturated straight chain C1-C 10 or branched C3-C 10 or a cyclic C3-C8 such as C5-C6 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -O-R3,

[0214] ii) -S-R3,

[0215] iii) -C(O)-O-R3, and

[0216] iv) phenyl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C4 alkoxy groups such as methoxy,

[0217] Preferably substituted with one or more groups selected from i) and iii), preferably iii), such as carboxyl; and

[0218] R3 is a group selected from the following

[0219] a) hydrogen atoms, and

[0220] b) Saturated straight chain C1-C6 or branched C3-C6 alkyl

[0221] Preferably, the compound of formula (I) and the tautomer (I') or a salt thereof, an optical isomer thereof, and a racemate and / or a solvate thereof (such as a hydrate), alone or as a mixture

[0222] Has the following meanings:

[0223] R1 is a group selected from the following

[0224] a) hydrogen atoms, and

[0225] b) saturated linear C1-C4 or branched C3-C4 alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -O-R3, more preferably unsubstituted;

[0226] R2 is a group selected from the following

[0227] a) hydrogen atoms; and

[0228] b) Saturated straight chain C1-C 10 or branched C3-C 10 or a cyclic C3-C8 such as C5-C6 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -O-R3,

[0229] iii) -C(O)-O-R3,

[0230] iv) C5-C 12 Aryl, which is optionally substituted with one or more hydroxyl groups and / or one or more C1-C4 alkoxy groups; and

[0231] R3 is a group selected from the following

[0232] a) hydrogen atoms, and

[0233] b) Saturated straight-chain C1-C4 or branched C3-C4 alkyl groups, such as methyl or ethyl.

[0234] Preferably, the compound of formula (I) and the tautomer (I') or a salt thereof, an optical isomer thereof, and a racemate and / or a solvate thereof (such as a hydrate), alone or as a mixture

[0235] Has the following meanings:

[0236] R1 is a hydrogen atom; and

[0237] R2 is a group selected from the following

[0238] a) hydrogen atoms, and

[0239] b) a saturated linear C1-C5 or branched C3-C5 or cyclic C3-C8, e.g. C5-C6 hydrocarbon radical, substituted by one or more groups, which may be identical or different, selected from v) -C(O)-O-R3, preferably substituted by a group iii) -C(O)-O-R3; R2 is even more preferably a saturated linear C1-C4 or branched C3-C4 hydrocarbon radical substituted by a group iii) -C(O)-OR3; and

[0240] R3 is a group selected from the following

[0241] a) hydrogen atoms, and

[0242] b) Saturated straight-chain C1-C4 or branched C3-C4 alkyl groups, such as methyl or ethyl.

[0243] According to another preferred embodiment, the compound of formula (I) and the tautomer (I') are selected from the compounds of formula (II) and the tautomers of formula (II') below, their salts, their solvates and their optical isomers, and their racemates, alone or as a mixture:

[0244]

[0245] In formula (II) and (II'), R1 and R3 have the same meanings as R1 and R3 in the compounds of formula (I) and (I'), and X refers to an alkylene group -(CH2) n -, wherein n is an integer from 1 to 10, preferably from 1 to 6, more preferably from 1 to 4, such as 1, preferably R3 represents a hydrogen atom.

[0246] Among the compounds of formula (I), preference is given to using the following compounds and their tautomers or their salts, their optical isomers, and their racemates and / or solvates (such as hydrates), alone or as a mixture:

[0247]

[0248]

[0249]

[0250]

[0251] Among these compounds, the following compounds are more particularly preferred:

[0252]

[0253]

[0254]

[0255] More preferably, among these compounds, the following compounds are more particularly preferred:

[0256]

[0257]

[0258] Even more preferably, among these compounds, the following compounds are more particularly preferred:

[0259]

[0260]

[0261] In the most preferred embodiment, the compounds according to the invention are as follows:

[0262]

[0263] All of the above compounds can be obtained from commercially available reagents by chemical methods known to those skilled in the art.

[0264] (1) Thiopyridone compounds can be prepared according to the methods described in, for example, EP-A-3390363 or WO 2017 / 102349, which are incorporated herein by reference.

[0265] The (1) thiopyridone compound may be an active ingredient or active compound in a cosmetic or dermatological product. The term "active" ingredient or compound as used herein refers to an ingredient or compound having cosmetic or dermatologically active properties such as antioxidant, whitening, UV filtering effect and antibacterial effect. The (1) thiopyridone compound used in the present invention may act as a decolorizing agent, bleaching agent or whitening agent, and thus the composition according to the present invention may be used as a whitening product or a cosmetic composition for whitening keratin substances.

[0266] (1) The thiopyridone compounds are useful as agents for depigmenting, bleaching or whitening the skin, body hair, eyelashes or hair and lips and / or nails, and preferably the skin, in particular for removing pigmented spots or aging spots, and / or as sunscreens.

[0267] (1) The amount of the (one or more) thiopyridone compounds in the composition according to the present invention may be 0.01 wt% or more, preferably 0.05 wt% or more, and more preferably 0.1 wt% or more, relative to the total weight of the composition.

[0268] On the other hand, the amount of (1) (one or more) thiopyridone compounds in the composition according to the present invention may be 10 wt % or less, preferably 5 wt % or less, and more preferably 3 wt % or less, relative to the total weight of the composition.

[0269] (1) The amount of the (one or more) thiopyridone compounds in the composition according to the invention may be 0.01 to 10% by weight, preferably 0.05 to 5% by weight, more preferably 0.1 to 3% by weight, relative to the total weight of the composition.

[0270] According to another embodiment of the present invention, the amount of (1) (one or more) thiopyridone compounds in the composition according to the present invention can be 0.01% to 10% by weight, preferably 0.1% to 5% by weight, in particular 0.5% to 3% by weight, relative to the total weight of the composition.

[0271] (Chelating Agent)

[0272] The composition according to the present invention comprises (2) at least one chelating agent. Two or more chelating agents may be used in combination. Thus, a single type of chelating agent or a combination of different types of chelating agents may be used.

[0273] The (2) chelating agent may be an organic or inorganic chelating agent. It may be preferred that the (2) chelating agent is selected from organic chelating agents.

[0274] (2) Chelating agents can be selected from carboxylic acids, preferably aminocarboxylic acids, hydroxycarboxylic acids (hydroxy acids), phosphonic acids, preferably aminophosphonic acids, polyphosphoric acids, preferably linear polyphosphoric acids and salts thereof. The salts can be, for example, alkali metal salts, alkaline earth metal salts or ammonium salts and substituted ammonium salts.

[0275] As (2) chelating agents, there may be mentioned:

[0276] (i) Aminocarboxylic acids and their salts, such as the compounds with the following INCI names: diethylenetriaminepentaacetic acid (DTPA), ethylenediaminetetraacetic acid (EDTA) and its salts, such as EDTA 2Na and EDTA 4Na, ethylenediamine-N,N'-diglutaric acid (EDDG), glycinamide-N,N'-disuccinic acid (GADS), 2-hydroxypropylenediamine-N,N'-disuccinic acid (HPDDS), ethylenediamine-N,N'-bis(o-hydroxyphenylacetic acid) (EDDHA), N,N'-bis(2-hydroxyphenyl)ethylenediamine-N,N'-diacetic acid (HBED), nitrotriacetic acid (NTA), methylglycinediacetic acid (MGDA), N-2-hydroxyethyl-N,N-diacetic acid and glyceryliminodiacetic acid (e.g., EP-A-3175). 42 and EP-A-399133), iminodiacetic acid-N-2-hydroxypropylsulfonic acid and aspartic acid N-carboxymethyl N-2-hydroxyphenyl-3-sulfonic acid (as described in EP-A-516102), β-alanine-N,N'-diacetic acid, aspartic acid-N,N'-diacetic acid and aspartic acid-N-monoacetic acid (described in EP-A-509382), chelating agents based on iminodisuccinic acid (IDSA) (as described in EP-A-509382), ethanol diglycine, phosphonic acid butanetricarboxylic acid, such as the compound sold by Bayer under the reference Bayhibit AM, sodium glutamate diacetate (GLDA), such as Dissolvine GL38 or 45S from AkzoNobel;

[0277] (ii) hydroxycarboxylic acids and their salts, such as citric acid and its salts, for example sodium citrate, in particular disodium citrate;

[0278] (iii) chelating agents based on mono- or polyphosphonic acids and their salts, such as compounds with the following INCI names: diethylenetriaminepenta(methylenephosphonic acid) (DTPMP), ethane-1-hydroxy-1,1,2-triphosphonic acid (E1HTP), ethane-2-hydroxy-1,1,2-diphosphonic acid (E2HTP), ethane-1-hydroxy-1,1-diphosphonic acid (EHDP), ethane-1,1,2-triphosphonic acid (ETP), ethylenediaminetetramethylenephosphonic acid (EDTMP) and hydroxyethane-1,1-diphosphonic acid (HEDP), their salts and derivatives, and

[0279] (iv) chelating agents based on polyphosphoric acid and its salts, such as compounds with the following INCI names: sodium tripolyphosphate (STP), tetrasodium diphosphate, hexametaphosphoric acid, sodium metaphosphate, phytic acid, its salts and derivatives,

[0280] as well as

[0281] A mixture thereof.

[0282] It may be preferred that the (2) chelating agent is selected from aminocarboxylic acids and salts thereof, hydroxycarboxylic acids and salts thereof, and more preferably selected from carbamic acid and salts thereof.

[0283] It may be more preferred that (2) the chelating agent is selected from EDTA and its salts (e.g. EDTA 2Na and EDTA 4Na), citric acid and its salts (e.g. sodium citrate), N,N-bis(carboxymethyl)-L-glutamic acid and its salts (tetrasodium glutamate diacetate), metaphosphates (e.g. sodium metaphosphate) and mixtures thereof.

[0284] According to another embodiment of the invention, (2) the chelating agent may preferably be chosen from succinic acid derivatives, such as ethylenediamine disuccinic acid and its salts. The chelating agent is particularly useful for reducing the electrostatic binding associated with the water present in large quantities in the intermediate cosmetic and / or care composition according to the invention. According to the invention, the chelating agent may be present in the composition at 0.001% to 1% by weight, preferably 0.01% to 0.5% by weight, relative to the total weight of the composition according to the invention.

[0285] However, depending on the specific circumstances, the composition according to the present invention may not include EDTA or its salts (eg, EDTA2Na and EDTA 4Na).

[0286] (2) The amount of the (one or more) chelating agents in the composition according to the present invention may be 0.01 wt % or more, preferably 0.05 wt % or more, and more preferably 0.1 wt % or more, in particular 0.2 wt % or more, relative to the total weight of the composition.

[0287] On the other hand, the amount of (2) (one or more) chelating agents in the composition according to the present invention may be 3 wt % or less, preferably 2 wt % or less, and more preferably 1 wt % or less, in particular 0.4 wt % or less, relative to the total weight of the composition.

[0288] (2) The amount of (one or more) chelating agents in the composition according to the invention may be 0.01% to 3% by weight, preferably 0.05% to 2% by weight, more preferably 0.1% to 1% by weight, in particular 0.2% to 0.4% by weight, relative to the total weight of the composition.

[0289] In the composition according to the present invention, the weight ratio of the amount of (1) (one or more) thiopyridone compounds to the amount of (2) (one or more) chelating agents may be 0.5 or greater, preferably 1.0 or greater, and more preferably 1.5 or greater.

[0290] On the other hand, in the composition according to the present invention, the weight ratio of the amount of (1) (one or more) thiopyridone compounds to the amount of (2) (one or more) chelating agents can be 4 or less, preferably 3 or less, and more preferably 2 or less.

[0291] In the composition according to the present invention, the weight ratio of the amount of (1) (one or more) thiopyridone compounds to the amount of (2) (one or more) chelating agents may be 0.5 to 4, preferably 1.0 to 3, and more preferably 1.5 to 2.

[0292] (pH adjuster)

[0293] The composition according to the present invention may contain (3) at least one pH adjuster (pH regulator). Two or more pH adjusters may be used in combination. Thus, a single type of pH adjuster or a combination of different types of pH adjusters may be used.

[0294] As (3) the pH adjuster, at least one acidifying agent and / or at least one alkalizing agent (alkaline agent) may be used.

[0295] The acidulant may be a monovalent or polyvalent acid, such as a divalent acid.

[0296] The acidulant may be, for example, a mineral (inorganic) acid, such as hydrochloric acid, sulfuric acid, phosphoric acid, or an organic acid, such as a carboxylic acid, for example tartaric acid, citric acid and lactic acid, and a sulfonic acid.

[0297] The alkalizing agent may be a monovalent or polyvalent base, such as a divalent base.

[0298] Alkalizing agents may be mineral (inorganic) or organic, or a mixture.

[0299] The mineral alkalizing agent may be selected from aqueous ammonia; alkali metal carbonates or bicarbonates, such as sodium carbonate or potassium carbonate and sodium bicarbonate or potassium carbonate; alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide; and mixtures thereof.

[0300] The organic alkalizing agent may be chosen from organic amines having a pKb at 25°C of less than 12, preferably less than 10, and even more advantageously less than 6. It should be noted that the pKb corresponds to a function of the maximum basicity. Furthermore, the organic amine does not contain any alkyl or alkenyl fatty chain containing more than 10 carbon atoms.

[0301] The organic alkalizing agent may be selected from, for example, alkanolamines, oxyethylenated and / or oxypropylenated ethylenediamines, amino acids and amine compounds of the following formula (III):

[0302]

[0303] in

[0304] W represents a C1-C6 divalent alkylene group optionally substituted by one or more hydroxyl groups or C1-C6 alkyl groups, and optionally interrupted by one or more heteroatoms such as O and N, and

[0305] R x , R y , R z and R t may be the same or different and represent a hydrogen atom or a C1-C6 alkyl, C1-C6 hydroxyalkyl or C1-C6 aminoalkyl group.

[0306] Examples of amine compounds of formula (III) that may be mentioned include 1,3-diaminopropane, 1,3-diamino-2-propanol, spermine and spermidine.

[0307] The term "alkanolamine" refers to an organic amine comprising a primary, secondary or tertiary amine functional group and one or more linear or branched C1-C8 alkyl groups bearing one or more hydroxyl groups.

[0308] Alkanolamines containing 1 to 3 identical or different C1-C4 hydroxyalkyl groups (such as monoalkanolamines, dialkanolamines or trialkanolamines) may be suitable for the present invention. Among such compounds, mention may be made of monoethanolamine (MEA), diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, N-dimethylaminoethanolamine, 2-amino-2-methyl-1-propanol, triisopropanolamine and 2-amino-2-methyl-1,3-propanediol, 3-amino-1,2-propanediol, 3-dimethylamino-1,2-propanediol and tris(hydroxymethylamino)methane.

[0309] The amino acids that can be used are of natural or synthetic origin, in their L, D or racemic form, and comprise at least one acid function more particularly chosen from carboxylic acid, sulfonic acid, phosphonic acid or phosphoric acid functions. The amino acids can be in neutral or ionic form.

[0310] As amino acids that can be used in the present invention, there can be mentioned especially aspartic acid, glutamic acid, alanine, arginine, ornithine, citrulline, asparagine, carnitine, cysteine, glutamine, glycine, histidine, lysine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine and valine.

[0311] Preferably, the amino acid is a basic amino acid comprising an additional amine function optionally contained in a ring or in a ureido function.

[0312] Such basic amino acids may preferably be selected from those corresponding to the following formula (IV):

[0313]

[0314] in

[0315] R represents a group selected from the following

[0316]

[0317] -(CH2)3-NH2,

[0318] -(CH2)2-NH2,

[0319] -(CH2)2-NH-CO-NH2, and

[0320]

[0321] Compounds corresponding to formula (IV) include histidine, lysine, arginine, ornithine and citrulline.

[0322] The organic alkalizing agent may be selected from heterocyclic organic amines. In addition to histidine, which has already been mentioned among the amino acids, pyridine, piperidine, imidazole, triazole, tetrazole and benzimidazole may also be mentioned.

[0323] The organic alkalizing agent may also be selected from amino acid dipeptides. As amino acid dipeptides that can be used in the present invention, mention may be made especially of carnosine, anserine and baleine.

[0324] The organic alkalizing agent can also be selected from compounds containing a guanidine function. As amines of this type that can be used in the present invention, in addition to the already mentioned arginine as an amino acid, creatine, creatinine, 1,1-dimethylguanidine, 1,2-diethylguanidine, sugar ring amine, metformin, agmatine, N-amidinoalanine, 3-guanidinopropionic acid, 4-guanidinobutyric acid and 2-([amino(imino)methyl]amino)ethane-1-sulfonic acid can also be mentioned.

[0325] In a preferred embodiment of the present invention, the organic alkalizing agent may be selected from amino acids, preferably basic amino acids, and more preferably arginine, lysine, histidine or a mixture thereof. Even more preferably, the organic alkalizing agent may be arginine.

[0326] Miscellaneous compounds that may be mentioned include the salts of the aforementioned amines with acids such as carbonic acid or hydrochloric acid. In particular, guanidine carbonate or monoethanolamine hydrochloride may be used.

[0327] (3) The pH adjuster may be present in an amount of 0.01 wt % or more, preferably 0.05 wt % or more, and more preferably 0.1 wt % or more, relative to the total weight of the composition.

[0328] (3) The pH adjuster may be present in an amount of 15 wt % or less, preferably 10 wt % or less, and more preferably 5 wt % or less, relative to the total weight of the composition.

[0329] (3) The pH adjuster may be present in an amount of 0.01 to 15 wt %, preferably 0.05 to 10 wt %, and more preferably 0.1 to 5 wt % or less relative to the total weight of the composition.

[0330] It is preferred that the pH of the composition according to the present invention is 4.5 or greater, and more preferably 5 or greater.

[0331] It is preferred that the pH of the composition according to the present invention is 6.5 or less, and more preferably 6 or less.

[0332] It is preferred that the pH of the composition according to the invention is from 4.5 to 6.5, and more preferably from 5 to 6.

[0333] The pH of the composition refers to the pH of the aqueous phase of the composition according to the present invention. The pH can be measured according to JIS Z 8802 (2011).

[0334] It may be preferred to also use at least one buffer or buffering agent as (3) a pH adjuster in combination with an acidifying agent and / or an alkalizing agent to stabilize the pH of the composition according to the invention.

[0335] As a buffer, any known buffer can be used. For example, a salt of an acid or a base, preferably a salt of a weak acid or a weak base, can be used. For example, if citric acid or lactic acid is used as an acidulant, sodium citrate or sodium lactate can be used as a buffer.

[0336] (water)

[0337] The composition according to the present invention may contain (4) water.

[0338] (4) The amount of water in the composition according to the present invention may be 30% by weight or more, preferably 35% by weight or more, and more preferably 40% by weight or more, relative to the total weight of the composition.

[0339] On the other hand, the amount of (4) water in the composition according to the present invention may be 99 wt% or less, preferably 95 wt% or less, and more preferably 90 wt% or less, relative to the total weight of the composition.

[0340] (4) The amount of water in the composition according to the present invention may be 30% to 99% by weight, preferably 35% to 95% by weight, and more preferably 40% to 90% by weight, relative to the total weight of the composition.

[0341] (Other optional additives)

[0342] The composition according to the invention may also contain any other optional additive(s) commonly used in the cosmetic field, for example selected from solvents, surfactants, antioxidants, cosmetic active agents other than ingredient (1) such as oils, preservatives, and mixtures thereof.

[0343] It is a matter of routine operation for a person skilled in the art to adjust the nature and amount of the above optional additives that may be present in the compositions according to the invention so that the desired cosmetic properties are not affected thereby.

[0344] As solvents, mention may be made of one or more cosmetically acceptable organic solvents, which may be alcohols: in particular monohydric alcohols, such as ethanol, isopropanol, benzyl alcohol and phenylethyl alcohol; diols, such as ethylene glycol, propylene glycol and butylene glycol; other polyols, such as glycerol, sugars and sugar alcohols; and ethers, such as ethylene glycol monomethyl ether, monoethyl ether and monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether and propylene glycol monobutyl ether, and butylene glycol monomethyl ether, butylene glycol monoethyl ether and butylene glycol monobutyl ether.

[0345] The organic solvent(s) may be present in a concentration of 0.01 to 30 wt %, preferably 0.1 to 20 wt %, and more preferably 1 to 10 wt %, relative to the total weight of the composition.

[0346] As the surfactant, nonionic surfactants or mixtures thereof may be mentioned. Examples of usable nonionic surfactants may include esters of polyols and fatty acids having saturated chains or containing unsaturated chains, and oxyalkylene derivatives thereof, i.e. derivatives containing oxyethylenated and / or oxypropylenated units, such as glycerol esters and oxyalkylene derivatives thereof; polyethylene glycol esters and oxyalkylene derivatives thereof; sorbitol esters and oxyalkylene derivatives thereof; sugar (sucrose, glucose or alkyl glucose) esters and oxyalkylene derivatives thereof; fatty alcohol ethers; sugar ethers and mixtures thereof.

[0347] Glycerol esters of fatty acids that may especially be mentioned include glyceryl stearate (glyceryl monostearate, glyceryl distearate and / or glyceryl tristearate).

[0348] Polyethylene glycol esters of fatty acids that may especially be mentioned include polyethylene glycol 40 OE monostearate.

[0349] Mixtures of these surfactants may also be used.

[0350] The nonionic surfactant may be present in the composition according to the invention in an amount ranging from 0.1% to 15% by weight, such as from 0.15% to 10% by weight, relative to the total weight of the composition.

[0351] [preparation]

[0352] The compositions according to the present invention may be prepared by mixing the essential and optional ingredients described above in conventional manner.

[0353] For example, the composition according to the present invention can be prepared by a method comprising the following steps

[0354] mix

[0355] (1) at least one thiopyridone compound; and

[0356] (2) At least one chelating agent.

[0357] Any optional ingredients may be further mixed.

[0358] The mixing can be carried out at any temperature, such as room temperature (e.g. 20-25°C, preferably at 25°C), preferably at a temperature of 30°C or higher, preferably 40°C or higher, and more preferably 50°C or higher. It is preferably further mixed with any of the above optional ingredients such as a pH adjuster.

[0359] The form of the composition according to the present invention is not particularly limited, and may take various forms, such as W / O emulsion, O / W emulsion, gel, solution, etc. It is preferred 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. In a preferred embodiment according to the present invention, the composition comprises a hydrophilic gelling agent.

[0360] [Beauty Methods]

[0361] The composition according to the invention can be used as a cosmetic or dermatological composition, preferably a cosmetic composition, and more preferably a cosmetic composition for keratinous substances. As keratinous substances, mention may be made of the skin, scalp, hair, mucous membranes such as lips, and nails.

[0362] The composition according to the invention can be used as a depigmenting, bleaching or whitening product for keratinous substances such as the skin. In particular, the composition according to the invention can be used as a whitening product.

[0363] The composition according to the invention may preferably be intended for application to keratin substances such as the skin, the scalp and / or the lips, preferably the skin.

[0364] Thus, the composition according to the invention can be used in a cosmetic method for keratinous materials, preferably the skin. In one embodiment, the invention relates to a cosmetic method for keratinous materials, preferably the skin, preferably a whitening method, comprising the step of applying a composition according to the invention to a keratinous material.

[0365] The composition according to the invention can be used as a topical cosmetic composition in the form of a lotion, milky lotion, cream, gel, paste, serum, foam or spray.

[0366] The composition according to the invention may also be used in a non-therapeutic cosmetic method for caring for or making up keratin materials, which comprises applying the composition according to the invention to the keratin materials.

[0367] [use]

[0368] The present invention also relates to the use of (2) at least one chelating agent in a composition comprising (1) at least one compound selected from the group consisting of a compound of the following formula (I), a tautomer of the following formula (I'), a salt thereof, a solvate thereof such as a hydrate, an optical isomer thereof, a racemate thereof, and a mixture thereof:

[0369]

[0370] in

[0371] R1 is a group selected from the following

[0372] a) hydrogen atoms, and

[0373] b) Saturated straight chain C1-C 10 or branched C3-C 10 Alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0374] i)-O-R3, and

[0375] ii) -S-R3,

[0376] and

[0377] R2 is a group selected from the following

[0378] a) Hydrogen atoms,

[0379] b) Saturated straight chain C1-C 12 or branched C3-C 12 or a cyclic C3-C8 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0380] i) -O-R3,

[0381] ii) -S-R3,

[0382] iii) -C(O)-O-R3, and

[0383] iv) C5-C 12aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups, and

[0384] c) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups,

[0385] in

[0386] R3 is a group selected from the following

[0387] a) hydrogen atoms, and

[0388] b) Saturated straight chain C1-C 10 or branched C3-C 10 alkyl

[0389] To stabilize (1) (one or more) compounds.

[0390] The term "stabilizing" has the same meaning as enhancing stability.

[0391] The use according to the present invention can improve (1) the stability of the thiopyridone compound in the composition containing the thiopyridone compound.

[0392] The use according to the invention thus makes it possible to store the composition comprising the (1) thiopyridone compound for a long period of time, in particular even under hot conditions.

[0393] The above explanations concerning (1) the thiopyridone compound and (2) the chelating agent for the composition according to the invention also apply to those used in the use according to the invention.

[0394] The composition in the use according to the invention may comprise any optional ingredients as explained above for the composition according to the invention.

[0395] More particularly, a subject of the invention is the cosmetic use of a composition as defined above for caring for the skin, preferably for lightening the skin, and / or for reducing or lightening darker and / or more pigmented spots on the skin.

[0396] In a particular embodiment, the composition is suitable for treating darker and / or more pigmented spots on the skin.

[0397] [Specific Embodiment]

[0398] The present invention can be described by the following non-limiting embodiments:

[0399] 1. A composition, preferably a cosmetic composition, comprising

[0400] (1) at least one compound selected from the group consisting of a compound of the following formula (I), a tautomer of the following formula (I'), a salt thereof, a solvate thereof such as a hydrate, an optical isomer thereof, a racemate thereof, and a mixture thereof:

[0401]

[0402] in

[0403] R1 is a group selected from the following

[0404] a) hydrogen atoms, and

[0405] b) Saturated straight chain C1-C 10 or branched C3-C 10 Alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0406] i)-O-R3, and

[0407] ii) -S-R3,

[0408] and

[0409] R2 is a group selected from the following

[0410] a) Hydrogen atoms,

[0411] b) Saturated straight chain C1-C 12 or branched C3-C 12 or a cyclic C3-C8 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0412] i) -O-R3,

[0413] ii) -S-R3,

[0414] iii) -C(O)-O-R3, and

[0415] iv) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups, and

[0416] c) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups,

[0417] in

[0418] R3 is a group selected from the following

[0419] a) hydrogen atoms, and

[0420] b) Saturated straight chain C1-C 10or branched C3-C 10 alkyl;

[0421] and

[0422] (2) At least one chelating agent.

[0423] 2. A composition according to embodiment 1, wherein:

[0424] R1 in formula (I) and (I') represents a hydrogen atom;

[0425] or

[0426] R1 in formula (I) and (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially linear (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl, especially the alkyl of R1 is unsubstituted.

[0427] 3. A composition according to embodiment 1 or 2, wherein:

[0428] R2 in formula (I) and (I') represents a hydrogen atom;

[0429] or

[0430] R2 in formula (I) and (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially straight-chain (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl, and the alkyl of R2 is unsubstituted.

[0431] 4. A composition according to embodiment 1 or 2, wherein:

[0432] R2 in formula (I) and (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially straight-chain (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; the alkyl is substituted by one or more groups selected from i), ii), iii) and iv) as defined above, preferably the alkyl is substituted by one or two groups selected from i), ii) and iii), more preferably substituted by one or two groups selected from i) and iii), better substituted by a group iii) such as carboxyl.

[0433] 5. A composition according to embodiment 1 or 2, wherein:

[0434] R2 in formula (I) and (I') represents a (C3-C8) cycloalkyl group, preferably a (C5-C7) cycloalkyl group such as a cyclohexyl group;

[0435] or

[0436] R2 in formula (I) and (I') represents a C5-C8 alkoxyl group optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxyl groups. 12 Aryl is preferably, in particular, unsubstituted phenyl.

[0437] 6. The composition according to any one of embodiments 1 to 5, wherein:

[0438] R3 in formula (I) and (I') represents a hydrogen atom;

[0439] or

[0440] R3 in formula (I) and (I') represents a saturated straight chain C1-C 10 or branched C3-C 10 Alkyl, in particular straight chain (C1-C6) alkyl or branched chain (C3-C6) alkyl, preferably (C1-C4) alkyl such as methyl.

[0441] 7. A composition according to any one of embodiments 1 to 6, wherein:

[0442] R1 in formula (I) and (I') represents a group selected from the following

[0443] a) hydrogen atoms, and

[0444] b) saturated straight-chain C1-C6 or branched C3-C6 alkyl groups, which are optionally substituted by one or more groups, which may be the same or different, and are selected from

[0445] i)-O-R3, and

[0446] ii) -S-R3,

[0447] Preferably optionally substituted with one or more groups i);

[0448] R2 in formula (I) and (I') represents a group selected from the following

[0449] a) hydrogen atoms, and

[0450] b) Saturated straight chain C1-C 10 or branched C3-C 10 or a cyclic C3-C8 such as C5-C6 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -O-R3,

[0451] ii) -S-R3,

[0452] iii) -C(O)-O-R3, and

[0453] iv) phenyl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C4 alkoxy groups such as methoxy,

[0454] Preferably substituted with one or more groups selected from i) and iii), preferably iii), such as carboxyl; and

[0455] R3 in formula (I) and (I') represents a group selected from the following

[0456] a) hydrogen atoms, and

[0457] b) saturated straight-chain C1-C6 or branched C3-C6 alkyl groups,

[0458] Preferably, the compounds of formula (I) and tautomers (I'), their salts, their solvates such as hydrates, their optical isomers, their racemates and mixtures thereof have the following meanings:

[0459] R1 in formula (I) and (I') represents a group selected from the following

[0460] a) hydrogen atoms, and

[0461] b) saturated straight-chain C1-C4 or branched C3-C4 alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -OR3, more preferably unsubstituted;

[0462] R2 in formula (I) and (I') represents a group selected from the following

[0463] a) hydrogen atoms, and

[0464] b) Saturated straight chain C1-C 10 or branched C3-C 10 or a cyclic C3-C8 such as C5-C6 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -O-R3,

[0465] iii) -C(O)-O-R3, and

[0466] iv) C5-C 12 Aryl, which is optionally substituted with one or more hydroxyl groups and / or one or more C1-C4 alkoxy groups; and

[0467] R3 in formula (I) and (I') represents a group selected from the following

[0468] a) Hydrogen atom;

[0469] b) Saturated straight-chain C1-C4 or branched C3-C4 alkyl groups, such as methyl or ethyl.

[0470] 8. The composition according to any one of embodiments 1 to 7, wherein:

[0471] (1) The compound may be selected from the following compounds 1 to 24, their tautomers, their salts, their solvates such as hydrates, their optical isomers, their racemates and mixtures thereof, in particular compound 1, 2, 4, 6, 7, 9, 11, 12, 14, 15, 16, 17, 18, 19, 20 or 21, more in particular 1, 9, 16, 18, 19, 20 or 21, preferably 18, 19, 20 or 21, and more preferably 20:

[0472]

[0473]

[0474]

[0475]

[0476]

[0477] 9. A composition according to any one of embodiments 1 to 8, wherein the amount of (1) (one or more) compounds in the composition is 0.01% to 10% by weight, preferably 0.05% to 5% by weight, and more preferably 0.1% to 3% by weight, relative to the total weight of the composition.

[0478] 10. The composition according to any one of embodiments 1 to 9, wherein (2) the chelating agent is selected from organic chelating agents, preferably aminocarboxylic acids and salts thereof, hydroxycarboxylic acids and salts thereof, and mixtures thereof, and more preferably aminocarboxylic acids and salts thereof.

[0479] 11. A composition according to any one of embodiments 1 to 10, wherein (2) the chelating agent is selected from EDTA and its salts, citric acid and its salts, N,N-bis(carboxymethyl)-L-glutamic acid and its salts, metaphosphates and mixtures thereof.

[0480] 12. A composition according to any one of embodiments 1 to 11, wherein the amount of (2) (one or more) chelating agents in the composition is 0.01 wt % to 3 wt %, preferably 0.05 wt % to 2 wt %, more preferably 0.1 wt % to 1 wt %, relative to the total weight of the composition.

[0481] 13. A composition according to any one of embodiments 1 to 12, wherein the composition is for whitening keratinous materials, preferably the skin.

[0482] 14. A cosmetic method for keratinous materials, preferably skin, preferably a whitening method, comprising the following steps:

[0483] A composition according to any one of embodiments 1 to 13 is applied to a keratinous material.

[0484] 15. (2) Use of at least one chelating agent in a composition comprising (1) at least one compound selected from the group consisting of a compound of the following formula (I), a tautomer of the following formula (I'), a salt thereof, a solvate thereof such as a hydrate, an optical isomer thereof, a racemate thereof, and a mixture thereof:

[0485]

[0486] in

[0487] R1 is a group selected from the following

[0488] a) hydrogen atoms, and

[0489] b) Saturated straight chain C1-C 10 or branched C3-C 10 Alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0490] i)-O-R3, and

[0491] ii) -S-R3,

[0492] and

[0493] R2 is a group selected from the following

[0494] a) Hydrogen atoms,

[0495] b) Saturated straight chain C1-C 12 or branched C3-C 12 or a cyclic C3-C8 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0496] i) -O-R3,

[0497] ii) -S-R3,

[0498] iii) -C(O)-O-R3, and

[0499] iv) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups, and

[0500] c) C5-C 12aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups,

[0501] in

[0502] R3 is a group selected from the following

[0503] a) hydrogen atoms, and

[0504] b) Saturated straight chain C1-C 10 or branched C3-C 10 alkyl

[0505] To stabilize (1) (one or more) compounds.

[0506] The present invention can be further described by the following non-limiting embodiments:

[0507] 1. A composition comprising the following components:

[0508] A) at least one compound selected from the group consisting of the following compounds of formula (I) and tautomers of formula (I'); and salts, optical isomers, racemates and / or solvates such as hydrates thereof, either alone or as a mixture:

[0509]

[0510] Wherein formula (I) and (I'):

[0511] -R1 is a group selected from the following

[0512] a) Hydrogen atom;

[0513] b) Saturated straight chain C1-C 10 or branched alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0514] i)-O-R3

[0515] ii) -S-R3;

[0516] -R2 is a group selected from the following

[0517] a) Hydrogen atoms,

[0518] b) Saturated straight chain C1-C 12 or branched C3-C 12 or a cyclic C3-C8 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from

[0519] i)-O-R3

[0520] ii)-S-R3

[0521] iii) -C(O)-O-R3;

[0522] iv) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups,

[0523] c) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups,

[0524] -R3 refers to a group selected from the following:

[0525] a) Hydrogen atom;

[0526] b) Saturated straight chain C1-C 10 or branched C3-C 10 alkyl.

[0527] B) Chelating agents selected from succinic acid derivatives, such as ethylenediamine disuccinic acid, and salts thereof.

[0528] 2. A composition according to embodiment 1, wherein:

[0529] - R1 in formula (I) and (I') represents a hydrogen atom;

[0530] or

[0531] - R1 in formula (I) and (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially linear (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl, especially the alkyl of R1 is unsubstituted.

[0532] 3. A composition according to any one of the preceding embodiments, wherein:

[0533] - R2 in formula (I) and (I') represents a hydrogen atom;

[0534] or

[0535] - R2 in formula (I) and (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially straight-chain (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl, and the alkyl of R2 is unsubstituted.

[0536] 4. A composition according to embodiment 1 or 2, wherein:

[0537] - R2 in formula (I) and (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially straight-chain (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; the alkyl is substituted by one or more groups selected from i), ii), iii) and iv) as defined in Embodiment 1, preferably the alkyl is substituted by one or two groups selected from i), ii) and iii), more preferably substituted by one or two groups selected from i) and iii), better substituted by a group iii) such as carboxyl.

[0538] 5. A composition according to embodiment 1 or 2, wherein

[0539] - R2 in formula (I) and (I') represents a (C3-C8) cycloalkyl group, preferably a (C5-C7) cycloalkyl group such as cyclohexyl;

[0540] or

[0541] - R2 in formula (I) and (I') represents a C5-C8 alkoxyl group optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxyl groups; 12 Aryl is preferably, in particular, unsubstituted phenyl.

[0542] 6. A composition according to any one of the preceding embodiments, wherein

[0543] - R3 in formula (I) and (I') represents a hydrogen atom;

[0544] or

[0545] - R3 in formula (I) and (I') represents a saturated straight chain C1-C 10 or branched C3-C 10 Alkyl, in particular straight chain (C1-C6) alkyl or branched chain (C3-C6) alkyl, preferably (C1-C4) alkyl such as methyl.

[0546] 7. A composition according to any one of the preceding embodiments, wherein:

[0547] - R1 in formula (I) and (I') represents a group selected from the following

[0548] a) hydrogen atoms, and

[0549] b) saturated straight-chain C1-C6 or branched C3-C6 alkyl groups, which are optionally substituted by one or more groups, which may be the same or different, and are selected from

[0550] i)-O-R3, and

[0551] ii) -S-R3,

[0552] Preferably optionally substituted by one or more groups i)

[0553] - R2 in formula (I) and (I') represents a group selected from the following:

[0554] a) Hydrogen atom;

[0555] b) Straight chain C1-C 10 or branched C3-C 10 or a cyclic C3-C8 such as C5-C6 saturated hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from:

[0556] i)-O-R3

[0557] ii)-S-R3

[0558] iii) -C(O)-O-R3;

[0559] iv) phenyl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C4 alkoxy groups such as methoxy;

[0560] Preferably substituted with one or more groups selected from i) and iii), preferably iii) such as carboxyl

[0561] - R3 in formula (I) and (I') represents a group selected from the following:

[0562] a) Hydrogen atom;

[0563] b) saturated straight chain C1-C6 or branched C3-C6 alkyl;

[0564] Preferably, the compounds of formula (I) and tautomers (I'), or salts thereof, optical isomers thereof, racemates thereof, and / or solvates thereof such as hydrates, alone or as a mixture, have the following meanings:

[0565] - R1 in formula (I) and (I') represents a group selected from the following:

[0566] a) Hydrogen atom;

[0567] b) saturated straight-chain C1-C4 or branched C3-C4 alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -OR, more preferably unsubstituted;

[0568] - R2 in formula (I) and (I') represents a group selected from the following:

[0569] a) Hydrogen atom;

[0570] b) Straight chain C1-C10 or branched C3-C 10 or a cyclic C3-C8 such as C5-C6 saturated hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from:

[0571] i)-O-R3

[0572] iii) -C(O)-O-R3;

[0573] iv) C5-C 12 Aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C4 alkoxy groups;

[0574] - R3 in formula (I) and (I') represents a group selected from the following:

[0575] a) Hydrogen atom;

[0576] b) Saturated straight-chain C1-C4 or branched C3-C4 alkyl groups, such as methyl or ethyl.

[0577] 8. A composition according to any one of the preceding embodiments, wherein

[0578] The compound of formula (I) is selected from the following compounds 1 to 24, and their tautomers or salts thereof, their optical isomers, racemates, and / or solvates such as hydrates, alone or as a mixture, in particular compounds 1, 2, 4, 6, 7, 9, 11, 12, 14, 15, 16, 17, 18, 19, 20 or 21, more in particular 1, 9, 16, 18, 19, 20 or 21, preferably 18, 19, 20 or 21, more preferably 20:

[0579]

[0580]

[0581]

[0582]

[0583] 9. The composition according to any of the preceding embodiments, wherein the composition of formula (I) or (I') is present in an amount of 0.01 to 10 wt. %, preferably 0.5 to 3 wt. %, relative to the total weight of the composition.

[0584] 10. The composition according to any of the preceding embodiments, wherein the at least one water-soluble chelating agent for polyvalent metal ions is present in the second composition in an amount of 0.001 to 1 wt. %, preferably 0.01 to 0.5 wt. %, relative to the total weight of the composition.

[0585] 11. Use of a chelating agent selected from succinic acid derivatives such as ethylenediamine disuccinic acid (EDDS) and its salts for stabilizing compounds of formula (I) and tautomers of formula (I′) as defined in any one of embodiments 1 to 8, for example for stabilizing compound 20.

[0586] 12. A non-therapeutic cosmetic method for depigmenting, lightening and / or bleaching keratinous material, preferably the skin, comprising the steps of:

[0587] A composition according to any one of embodiments 1 to 10 is applied to a keratinous material. Example

[0588] The present invention will be described in more detail by way of examples. However, these examples should not be construed as limiting the scope of the present invention.

[0589] [Examples 1A-5A and Comparative Example 1A]

[0590] [preparation]

[0591] Each composition according to Examples 1A to 5A and Comparative Example 1A was prepared by mixing the ingredients shown in Table 1. The numerical values ​​for the amounts of the ingredients are all based on "weight %" as active materials.

[0592]

[0593] N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine (2-mercaptonicotinoylglycine): Compound 20

[0594] [Evaluate]

[0595] (pH)

[0596] The pH at 25° C. of each composition according to Examples 1A-5A and Comparative Example 1A was measured as follows.

[0597] equipment:

[0598] 1. pH meter; Laqua F-71 (Horiba)

[0599] 2. pH electrode; 9615S-10D (Horiba)

[0600] 3. pH standard solution (Horiba)

[0601] 4. pH probe internal solution (Horiba)

[0602] program:

[0603] 1. Open the internal solution filling port of the pH meter and supply the internal solution around the electrode.

[0604] 2. Calibrate at pH 9, 7 and 4 using standard solutions.

[0605] 3. Wash the electrode with deionized water.

[0606] 4. Remove the protective cap of one of the electrodes (glass electrode) and immerse the electrode in each of the compositions according to Examples 1A-5A and Comparative Example 1A.

[0607] 5. Record the pH after it stabilizes.

[0608] The results are shown in the "pH" row in Table 2 below.

[0609] (Thiopyridone compound retention rate)

[0610] The amount of the thiopyridone compound in each composition according to Examples 1A to 5A and Comparative Example 1A was measured by HPLC-UV assay at the following times.

[0611] Time (1) Immediately after preparation of the composition (T0)

[0612] Time (2) 2 weeks after preparation, wherein the composition is stored in a sealed and light-proof container at 55°C

[0613] Details of HPLC-UV detection are as follows.

[0614] Apparatus / reagents

[0615] HPLC System Ultra Performance LC (UPLC) HPLC columns RP18, 1.7μm, 2.1mm x 100mm Eluent A 0.1% phosphoric acid in water Eluent B Methanol

[0616] HPLC conditions

[0617]

[0618] The retention rate of thiopyridone compounds was determined by the following equation:

[0619] Thiopyridone compound retention rate (%) =

[0620] The amount of the thiopyridone compound at time (2) / the amount of the thiopyridone compound at time (1)

[0621] The results are shown in the row "Thiopyridone compound retention rate (%)" in Table 2 below.

[0622] Thiopyridone compound retention was also classified according to the following criteria:

[0623] Very good: 90% or more

[0624] Good: greater than 85% to less than 90%

[0625] Poor: 85% or less

[0626] The results are shown in the "Stability" row in Table 2 below.

[0627] Table 2

[0628]

[0629] (result)

[0630] The compositions according to Examples 1A to 5A, each of which contained a thiopyridone compound and various chelating agents, were more stable than the composition according to Comparative Example 1A not containing any chelating agent even at high temperatures, so that a larger amount of thiopyridone was retained.

[0631] [Examples 1B-2B and Comparative Examples 1B-2B]

[0632] These compounds are indicated by chemical name or INCI name. Unless otherwise indicated, the amounts / concentrations of the ingredients in the compositions / formulations described below are expressed in % by weight relative to the total weight of each composition / formulation.

[0633]

[0634] Compound 20 was synthesized as disclosed in Example 2 of patent EP3390363.

[0635] [preparation]

[0636] The inventive compositions of Example 1B and Example 2B and the comparative compositions of Comparative Example 1B and Comparative Example 2B were prepared from the ingredients shown in Table 3 below (wherein the contents are expressed as % by weight of the material relative to the total weight of the composition):

[0637] Table 3

[0638]

[0639]

[0640] Taking Example 1B as an example, the composition was prepared by the following steps:

[0641] 1). Heat the surfactant and fatty compound (if used) to 75°C and mix thoroughly until all solids are melted.

[0642] 2). Mix water, ethylene glycol and chelating agent, heat to 75°C, and mix thoroughly until there are no lumps.

[0643] 3). Transfer the oil phase to the water phase at 75°C and mix well for 15 minutes.

[0644] 4). Cool to 30℃.

[0645] 5). Finally, compound 20 and sodium hydroxide were added to adjust the pH to 5.7±0.3.

[0646] [Evaluate]

[0647] The degradation of Compound 20 by Example 1B and Comparative Example 1B of the inventive composition prepared in the "Preparation" section above was evaluated by the following steps:

[0648] - Accurately weigh 100 mg of the composition of the present invention and the comparative composition into 10 mL volumetric flasks respectively;

[0649] - Add 2.5 mL of ultrapure water and tighten the lid, then oscillate on a vortex to fully disperse it without obvious lumps;

[0650] -Fill the volumetric flask with methanol to the mark and securely close the lid;

[0651] - Sonicate the solution for 5 minutes and then cool to room temperature;

[0652] - Stir the solution on a magnetic stir plate for 1.5 hours; and

[0653] - Filter the solution using a 0.45μ GHP filter to obtain an injection solution;

[0654] And then:

[0655] -First, the test components were subjected to UPLC (ultra-high performance liquid chromatography) analysis to obtain T0 degradation data of compound 20; each composition had two parallel samples to be analyzed; wherein T0 refers to the time when the degradation test was started;

[0656] - The composition is then placed in an oven at 55°C for 2 weeks for accelerated aging test, and in an oven at 45°C for 1 month, or in an oven at 45°C for 2 months;

[0657] - Finally the aged compositions were analyzed; each composition had two parallel samples to be analyzed.

[0658] The results are given in Table 4 below.

[0659] Table 4

[0660]

Claims

1. A composition, preferably a cosmetic composition, comprising (1) at least one compound selected from the group consisting of a compound of the following formula (I), a tautomer of the following formula (I'), a salt thereof, a solvate thereof such as a hydrate, an optical isomer thereof, a racemate thereof, and a mixture thereof: in R1 is a group selected from the following a) hydrogen atoms, and b) Saturated straight chain C1-C 10 or branched C3-C 10 Alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from i)-O-R3, and ii) -S-R3, and R2 is a group selected from the following a) Hydrogen atoms, b) Saturated straight chain C1-C 12 or branched C3-C 12 or a cyclic C3-C8 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups, and c) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups, in R3 is a group selected from the following a) hydrogen atoms, and b) Saturated straight chain C1-C 10 or branched C3-C 10 alkyl; and (2) At least one chelating agent.

2. The composition according to claim 1, wherein: R1 in formula (I) and (I') represents a hydrogen atom; or R1 in formula (I) and (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially linear (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl, especially the alkyl of R1 is unsubstituted.

3. The composition according to claim 1 or 2, wherein: R2 in formula (I) and (I') represents a hydrogen atom; or R2 in formula (I) and (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially straight-chain (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl, and the alkyl of R2 is unsubstituted.

4. The composition according to claim 1 or 2, wherein: R2 in formula (I) and (I') represents a straight chain (C1-C 10 ) alkyl or branched (C3-C 10 )alkyl, especially straight-chain (C1-C6)alkyl or branched (C3-C6)alkyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; the alkyl is substituted by one or more groups selected from i), ii), iii) and iv) as defined above, preferably the alkyl is substituted by one or two groups selected from i), ii) and iii), more preferably substituted by one or two groups selected from i) and iii), better substituted by a group iii) such as carboxyl.

5. The composition according to claim 1 or 2, wherein: R2 in formula (I) and (I') represents a (C3-C8) cycloalkyl group, preferably a (C5-C7) cycloalkyl group such as a cyclohexyl group; or R2 in formula (I) and (I') represents a C5-C8 alkoxyl group optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxyl groups. 12 Aryl is preferably, in particular, unsubstituted phenyl.

6. A composition according to any one of claims 1 to 5, wherein: R3 in formula (I) and (I') represents a hydrogen atom; or R3 in formula (I) and (I') represents a saturated straight chain C1-C 10 or branched C3-C 10 Alkyl, in particular straight chain (C1-C6) alkyl or branched chain (C3-C6) alkyl, preferably (C1-C4) alkyl such as methyl.

7. A composition according to any one of claims 1 to 6, wherein: R1 in formula (I) and (I') represents a group selected from the following a) hydrogen atoms, and b) saturated straight-chain C1-C6 or branched C3-C6 alkyl groups, which are optionally substituted by one or more groups, which may be the same or different, and are selected from i)-O-R3, and ii) -S-R3, Preferably optionally substituted with one or more groups i); R2 in formula (I) and (I') represents a group selected from the following a) hydrogen atoms, and b) Saturated straight chain C1-C 10 or branched C3-C 10 or a cyclic C3-C8 such as C5-C6 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) phenyl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C4 alkoxy groups such as methoxy, Preferably substituted with one or more groups selected from i) and iii), preferably iii), such as carboxyl; and R3 in formula (I) and (I') represents a group selected from the following a) hydrogen atoms, and b) saturated straight-chain C1-C6 or branched C3-C6 alkyl groups, Preferably, the compounds of formula (I) and tautomers (I'), their salts, their solvates such as hydrates, their optical isomers, their racemates and mixtures thereof have the following meanings: R1 in formula (I) and (I') represents a group selected from the following a) hydrogen atoms, and b) saturated straight-chain C1-C4 or branched C3-C4 alkyl, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -OR3, more preferably unsubstituted; R2 in formula (I) and (I') represents a group selected from the following a) hydrogen atoms, and b) Saturated straight chain C1-C 10 or branched C3-C 10 or a cyclic C3-C8 such as C5-C6 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -O-R3, iii) -C(O)-O-R3, and iv) C5-C 12 Aryl, which is optionally substituted with one or more hydroxyl groups and / or one or more C1-C4 alkoxy groups; and R3 in formula (I) and (I') represents a group selected from the following a) Hydrogen atom; b) Saturated straight-chain C1-C4 or branched C3-C4 alkyl groups, such as methyl or ethyl.

8. A composition according to any one of claims 1 to 7, wherein: (1) The compound may be selected from the following compounds 1 to 24, their tautomers, their salts, their solvates such as hydrates, their optical isomers, their racemates and mixtures thereof, in particular compound 1, 2, 4, 6, 7, 9, 11, 12, 14, 15, 16, 17, 18, 19, 20 or 21, more in particular 1, 9, 16, 18, 19, 20 or 21, preferably 18, 19, 20 or 21, and more preferably 20:

9. The composition according to any one of claims 1 to 8, wherein the amount of (1) (one or more) compounds in the composition is 0.01% to 10% by weight, preferably 0.05% to 5% by weight, and more preferably 0.1% to 3% by weight, relative to the total weight of the composition.

10. The composition according to any one of claims 1 to 9, wherein (2) the chelating agent is selected from organic chelating agents, preferably aminocarboxylic acids and salts thereof, hydroxycarboxylic acids and salts thereof, and mixtures thereof, and more preferably aminocarboxylic acids and salts thereof.

11. The composition according to any one of claims 1 to 10, wherein (2) the chelating agent is selected from EDTA and its salts, citric acid and its salts, N,N-bis(carboxymethyl)-L-glutamic acid and its salts, metaphosphates and mixtures thereof.

12. The composition according to any one of claims 1 to 9, wherein (2) the chelating agent is selected from succinic acid derivatives, such as ethylenediamine disuccinic acid and salts thereof.

13. A composition according to any one of claims 1 to 12, wherein the amount of (2) (one or more) chelating agents in the composition is 0.01 wt % to 3 wt %, preferably 0.05 wt % to 2 wt %, more preferably 0.1 wt % to 1 wt %, relative to the total weight of the composition.

14. (2) Use of at least one chelating agent in a composition comprising (1) at least one compound selected from the group consisting of a compound of the following formula (I), a tautomer of the following formula (I'), a salt thereof, a solvate thereof such as a hydrate, an optical isomer thereof, a racemate thereof, and a mixture thereof: in R1 is a group selected from the following a) hydrogen atoms, and b) a saturated straight-chain C1-C 10 or branched C3-C 10 Alkyl groups, which may be the same or different, are selected from i)-O-R3, and ii) -S-R3, and R2 is a group selected from the following a) Hydrogen atoms, b) Saturated straight chain C1-C 12 or branched C3-C 12 or a cyclic C3-C8 hydrocarbon group, which is optionally substituted by one or more groups, which may be the same or different, selected from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups, and c) C5-C 12 aryl, which is optionally substituted by one or more hydroxyl groups and / or one or more C1-C8 alkoxy groups, in R3 is a group selected from the following a) hydrogen atoms, and b) Saturated straight chain C1-C 10 or branched C3-C 10 alkyl To stabilize (1) (one or more) compounds.

15. The use according to claim 14, wherein (2) the chelating agent is selected from succinic acid derivatives, such as ethylenediamine disuccinic acid and its salts.

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