Cosmetic or dermatological composition comprising a Thiopyridinone compound and a scleroglucan gum

Abstract

Title: Cosmetic or dermatological composition comprising a Thiopyridinone compound and a scleroglucan gum. The present invention relates to a composition, in particular cosmetic or dermatological, comprising at least one compound of formula (I) or (I'), as described below, and / or their optical isomers, geometric isomers as well as their acid or base salts, organic or mineral, and / or their solvates such as hydrates, and at least one scleroglucan gum, as well as the use of said composition in the cosmetic and dermatological fields, in particular for the care and treatment of keratinous materials, and in particular for the care, protection and / or makeup of the skin of the body or face, or for hair care.

Description

Title of the invention: Cosmetic or dermatological composition comprising a Thiopyridinone compound and a scleroglucan gum

[0001] The present invention relates to a composition, particularly for cosmetic or dermatological purposes, comprising at least one compound of formula (I) or (!'), as described below, and / or their optical isomers, geometric isomers, as well as their acid or base salts, organic or mineral, and / or their solvates such as hydrates, and at least one scleroglucan gum, and to the use of said composition in the cosmetic and dermatological fields, particularly for the care and treatment of keratinous materials, and especially for the care, protection, and / or makeup of the skin of the body or face, or for hair care. Technical field

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

[0003] The use of harmless topical depigmenting substances with good efficacy is particularly desirable for the purpose of treating pigment spots.

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

[0005] On the other hand, patent applications WO2012 / 080075 and WO2017 / 102349 disclose a new depigmenting agent which is a thiopyridinone compound. The thiopyridinone compound exhibits particularly effective depigmenting properties by reducing melanin production.

[0006] However, it has been discovered that the incorporation of a thiopyridinone compound tends to destabilize compositions over time, particularly when these are in the form of emulsions, leading to phase-shifting problems in the compositions due to its amphiphilic character.

[0007] In addition, it is advantageous to have a composition that exhibits good sensoriality when applied to keratinous materials, preferably the skin.

[0008] The Applicant made a surprising discovery that, by using scleroglucan gum, it was possible to substantially improve the stability of compositions comprising such a thiopyridinone compound. This discovery forms the basis of the present invention.

[0009] Thus, in accordance with one of the objects of the present invention, a composition, in particular cosmetic or dermatological, is now proposed, comprising at least one compound of formula (I) or (I'), as described below, and / or their optical isomers, geometric isomers as well as their acid or base salts, organic or mineral, and / or their solvates such as hydrates, and at least one scleroglucan gum.

[0010] Furthermore, it is known that radiation with wavelengths between 280 nm and 400 nm allows the human epidermis to tan, and that radiation with wavelengths between 280 and 320 nm, known as UV-B rays, interferes with the development of a natural tan. Exposure is also likely to induce an alteration of the biomechanical properties of the epidermis, resulting in the appearance of wrinkles and leading to premature skin aging.

[0011] It is also known that UV-A rays with wavelengths between 320 and 400 nm penetrate the skin more deeply than UV-B rays. UV-A rays cause immediate and persistent tanning of the skin. Daily exposure to UVA rays, even for short periods, under normal conditions can lead to the degradation of collagen and elastin fibers, resulting in changes to the skin's microrelief, the appearance of wrinkles, and uneven pigmentation (brown spots, uneven skin tone).

[0012] Protection against UVA and UVB radiation is therefore necessary. An effective photoprotection product must protect against both UVA and UVB radiation.

[0013] Numerous photoprotective compositions have been proposed to date to counteract the effects induced by UVA and / or UVB radiation. They generally contain mixtures of filters such as organic UV filters.

[0014] Numerous cosmetic compositions designed to limit skin darkening and improve skin tone and evenness have been proposed to date. It is well known in the field of sunscreens that such compositions can be obtained using UV filters, and in particular UVB filters. Some compositions may also contain UVA filters. This filtering system must provide UVB protection in order to limit and control the neosynthesis of melanin that promotes overall pigmentation, but it must also provide UVA protection in order to limit and control the oxidation of existing melanin that leads to skin darkening.

[0015] However, it is extremely difficult to find a composition containing a particular combination of UV filters that would be specially adapted for the photoprotection of the skin and particularly for an improvement in the quality of the skin both in terms of color and its mechanical properties of elasticity.

[0016] Advantageously, this improvement is particularly sought on already pigmented skin in order not to increase either the pigment load in melanin or the structure of the melanin already present in the skin.

[0017] Thus, it may be advantageous to combine a pigment spot prevention agent such as the thiopyridinone compounds mentioned above with UV filters to have a composition that limits the effects of UV, in particular the effects of skin pigmentation.

[0018] The Applicant also made a surprising discovery that, by using scleroglucan gum, it was possible to substantially improve the stability of compositions comprising such a thiopyridinone compound in combination with one or more UV filters. This discovery forms the basis of the present invention.

[0019] Thus, in accordance with one of the objects of the present invention, a composition, in particular cosmetic or dermatological, is now proposed, comprising at least one compound of formula (I) or (!'), as described below, and / or their optical isomers, geometric isomers as well as their acid or base salts, organic or mineral, and / or their solvates such as hydrates, at least one scleroglucan gum, and at least one UV filter. Description of the invention

[0020] Thus, the present invention relates to a composition, in particular a cosmetic or dermatological one, comprising: (a) at least one compound selected from compounds of formula (I), tautomers of formula (!'), their salts, their solvates, such as their hydrates, their optical isomers, their racemates, and mixtures thereof: (D (0 in which: - Ri denotes a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in Ci-CiO or branched in C3-CiO optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, and - R2 designates a radical chosen from a) a hydrogen atom, b) a linear saturated hydrocarbon group in C1-C12 or a branched hydrocarbon group in C3-C12 or a cyclic hydrocarbon group in C3-C8 optionally substituted by one or more groups, which may be identical 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 hydroxyl groups and / or by one or more CrC8 alkoxy radicals and c) a C5-C12 aryl group, optionally substituted by one or more hydroxyl groups and / or by one or more Ci-C8 alkoxy radicals, and - R3 designates a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in C1-C10 or branched in C3-C10; and (b) at least one scleroglucan gum.

[0021] This composition may optionally include at least one UV filter.

[0022] The present invention makes it possible to obtain compositions, in particular cosmetic or dermatological, which are stable over time, having good cosmetic properties, in particular being non-greasy and non-sticky, providing UV filtration, and having an effect on pigmentation induced by radiation in the UV and visible range.

[0023] The present invention also relates to a non-therapeutic cosmetic process for the care and / or makeup of a keratinous material comprising the application on the surface of said keratinous material of at least one composition according to the invention as defined above.

[0024] It also relates to a non-therapeutic cosmetic process for limiting skin darkening and / or improving the color and / or homogeneity of the complexion comprising the application on the surface of the keratinous material of at least one composition as defined above.

[0025] It also relates to a non-therapeutic cosmetic process for preventing and / or treating the signs of aging of a keratinous material comprising the application on the surface of the keratinous material of at least one composition as defined above.

[0026] The composition according to the invention exhibits good stability. This stability can be evaluated macroscopically and / or microscopically after storage for 24 hours, one week, one month, or two months at room temperature (25°C), 4°C, 45°C, or 55°C. A stable composition generally retains its pleasantness and sensory signature upon application over time. More specifically, the stability of a composition can be assessed qualitatively, for example, by the absence of separation or crystal formation at the macroscopic and / or microscopic level, or quantitatively by monitoring the evolution of parameters such as viscosity or pH.

[0027] By "stable over time" according to the present invention, we mean a composition which, after 1 week, preferably 1 month, even more preferably 2 months, of Storage at a temperature ranging from 4 to 55 °C presents few macroscopic changes such as changes in colour, odor, viscosity, pH, as well as slight variations in microscopic appearance (variation in droplet size and polydispersity).

[0028] Other features, aspects and advantages of the invention will become apparent from the detailed description that follows.

[0029] The composition according to the invention is intended for topical application and therefore contains a physiologically acceptable medium. Hereinafter, "physiologically acceptable medium" means a medium compatible with keratinous materials.

[0030] In the context of the present invention, "keratinous material" means in particular the skin, the scalp, keratinous fibers such as eyelashes, eyebrows, hair, and body hair, nails, mucous membranes such as lips, and more particularly the skin and mucous membranes (body, face, eye contour, eyelids, lips, preferably body, face and lips).

[0031] In what follows, and unless otherwise indicated, the bounds of a range of values ​​are included in that range, in particular in the expressions "between" and "ranging from ... to ...".

[0032] Furthermore, the expressions "at least one" and "at least" used in this description are respectively equivalent to the expressions "one or more" and "greater than or equal to".

[0033] By "prevent" or "prevention", according to the invention, means reducing the risk of occurrence or slowing down the occurrence of a given phenomenon, namely, according to the present invention, the signs of aging of a keratinous material. Detailed description of the invention Thiopyridinone compounds

[0034] The composition according to the present invention comprises at least one thiopyridinone compound. Two or more distinct thiopyridinone compounds, of formula (I) or (!'), may be used in combination. Thus, a single thiopyridinone compound of formula (I) or (!') or a combination of different thiopyridinone compounds of formula (I) or (!') may be used.

[0035] The thiopyridinone compound(s) are 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: (0 © in which: Ri denotes a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in Ci-Cio or branched in C3-CiO optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, and R2 denotes a radical chosen from a) a hydrogen atom, b) a linear saturated hydrocarbon group in Ci-Ci2 or branched in C3-Ci2 or cyclic in C3-C8, optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in CrC8, and c) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in CrC8, and R3 designates a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in Ci-Cio or branched in C3-Ci0.

[0036] Hereinafter, within the meaning of the present invention and unless otherwise indicated: - a "saturated, linear in Ci-Ci2 or branched in C3-Ci2" hydrocarbon group is equivalent to a "linear (in C1-C12) or branched (in C3-Ci2) alkyl group" which corresponds to a saturated, linear in CrCi2 or branched in C3-Ci2 hydrocarbon group, preferably a linear in Ci-Cio or branched in C3-Ci0 hydrocarbon group, and more preferably a linear in Ci-C6 or branched in C3-C6 hydrocarbon group; preferably, the linear or branched groups may be chosen from among the methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl groups; More preferably, the saturated alkyl groups, linear or branched, can be chosen from the methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl and octyl groups, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl; - a saturated hydrocarbon group "cyclic in C3-C8" is a mono- or bicyclic cycloalkyl group containing 3 to 8 carbon atoms, and in particular is a monocyclic cycloalkyl group in C5 to C7 such as a cyclohexyl group, - an "alkoxy radical" is an alkyl-oxy radical for which the alkyl radical is a linear or branched hydrocarbon radical in CrCi6, and preferably a hydrocarbon radical in Ci-C8; - when the alkoxy group is optionally substituted, this implies that the alkyl group is optionally substituted as defined above; - an "aryl" group represents a carbon-based group, monocyclic or bicyclic, fused or not, comprising from 5 to 12 carbon atoms, preferably from 6 to 10 carbon atoms, and in which at least one ring is aromatic; preferably, the aryl radical is a phenyl, biphenyl, naphthyl group, more preferably a phenyl group; - the expression "at least one" is equivalent to the expression "one or more"; and - the term "inclusive" for a range of concentrations means that the limits of that range are included in the defined range.

[0037] The salts of compounds of formula (I), (I'), (II), or (II') as defined below include conventional non-toxic salts of said compounds, such as those formed from an organic or inorganic acid or an organic or inorganic base.

[0038] Examples of salts of compounds of formula (I), (I'), (II) or (II') include: Salts obtained by adding 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; or An organic base such as a primary, secondary, or tertiary alkylamine, for example, triethylamine or butylamine. This primary, secondary, or tertiary alkylamine may contain one or more nitrogen and / or oxygen atoms and may thus include, for example, one or more alcohol groups. Examples include 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylaminopropanol, 2-amino-2-(hydroxymethyl)-1,3-propanediol, and 3-(dimethylamino)propylamine.

[0039] Other examples include amino acid salts, for instance lysine, arginine, guanidine, glutamic acid, and aspartic acid. Advantageously, the salts of compounds of formula (I) or (II) (when they include a carboxy group) can be selected from alkali or alkaline earth metal salts such as sodium, potassium, calcium, or magnesium salts and ammonium salts.

[0040] A "salt of an organic or inorganic acid" is more particularly chosen from salts chosen from a salt derived from i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(O)2OH such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S(O)2OH such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid; x) alkoxysulfinic acids: Alk-OS(O)OH such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; xii) phosphoric acid H3PO4; xiii) acetic acid CH3C(O)OH; xiv) triflic acid CF3SO3H; and xv) tetrafluoroboric acid HBF4.

[0041] 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.

[0042] Optical isomers are, in particular, enantiomers and diastereomers.

[0043] Compound (!') is the tautomeric form of compound (I) when a tautomeric equilibrium exists according to the following scheme: (b (H

[0044] According to one embodiment of the present invention, Ri represents a hydrogen atom.

[0045] According to one embodiment of the present invention, Ri of formula (I) and (!') represents a linear (Ci-CiO) or branched (C3-CiO) alkyl group, in particular a linear (Ci-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably, ethyl. In particular, said alkyl group of Ri' is unsubstituted.

[0046] According to one embodiment of the present invention, R2 represents a hydrogen atom.

[0047] According to one embodiment of the present invention, R2 represents a linear (Ci-Ci0) or branched (C3-Ci0) alkyl group, in particular a linear (Cr C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group of R2 not being substituted.

[0048] According to one embodiment of the present invention, R2 of formula (I) and (!') represents a linear (Ci-Ci) or branched (C3-Ci) alkyl group, in particular a linear (Ci-C6) or branched (C3-Ci) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group being substituted by one or more groups selected from i), ii), iii) and iv) as defined above. Preferably, said alkyl group being substituted by one or two groups selected from i), ii) and iii), more preferably by one or two groups selected from i) and iii), better substituted by a group iii) as a carboxy.

[0049] Another variant for the radical R2 is that said alkyl group is substituted by a group iv) in particular substituted by a phenyl group.

[0050] According to another embodiment of the present invention, R2 represents a cycloalkyl group (in C3-C8), preferably a cycloalkyl group (in C5-C7) such as cyclohexyl.

[0051] According to another embodiment of the present invention, R2 represents an aryl group in C5-Ci2 optionally substituted by one or more hydroxyls and / or by one or more alkoxy radicals in Ci-C8, preferably a phenyl group in particular unsubstituted.

[0052] According to one embodiment, R3 represents a hydrogen atom.

[0053] According to another embodiment, R3 represents a saturated alkyl group, linear in C1-C10 or branched in C3-Ci0; in particular a linear (in Ci-C6) or branched (in C3-C6) alkyl group, preferably an alkyl group (in CrC4) such as the methyl group.

[0054] Preferably, the compounds of formula (I) and the tautomer (!') or their salts, their optical isomers, racemates, and / or solvates such as their hydrates and their derivatives, alone or in mixture, have the following meanings: Ri denotes a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in Ci-C6 or branched in C3-C6 optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, preferably optionally substituted by one or more i) groups; R2 denotes a radical chosen from a) a hydrogen atom; b) a linear saturated hydrocarbon group in C1-C10 or branched in C3-C10 or cyclic in C3-C8 such as in C5-C6 optionally substituted by one or more groups, which may be the same or different, selected from: i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) a phenyl group optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in C1-C4 such as methoxy, preferably substituted by one or more groups selected from i) and iii), preferably iii) such as carboxy; and R3 designates a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in Ci-C6 or branched in C3-C6.

[0055] Preferably, the compounds of formula (I) and the tautomer (!') or their salts, their optical isomers, racemates, and / or their solvates such as their hydrates, alone or in mixture, have the following meanings: Ri denotes a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in C1-C4 or branched in C3-C4 optionally substituted by one or more groups, which may be identical or different, chosen from i) -OR3>plus preferably unsubstituted; R2 denotes a radical chosen from a) a hydrogen atom; and b) a linear saturated hydrocarbon group in C1-C10 or a branched hydrocarbon group in C3-C10 or a cyclic hydrocarbon group in C3-C8 as in C5-C6, optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, iii) -C(O)-O-R3, iv) an aryl group in C5-C12, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in C1-C4; and R3 designates a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in C1-C4 or branched in C3-C4 such as methyl or ethyl.

[0056] Preferably, the compounds of formula (I) and the tautomer (!') or their salts, their optical isomers, racemates, and / or solvates such as hydrates and their derivatives, alone or in mixture, have the following meanings: Ri is a hydrogen atom; and R2 denotes a radical chosen from a) a hydrogen atom, and b) a saturated hydrocarbon group, linear in C1-C5 or branched in C3-C5 or cyclic in C3-C8 such that C5-C6 may be identical or different, chosen from v) -C(O)-O-R3, preferably substituted by a group iii) -C(O)-O-R3; R2 is more preferably a saturated hydrocarbon group, linear in C1-C4 or branched in C3-C4 substituted by a group iii) -C(O)-OR3; and R3 designates a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in C1-C4 or branched in C3-C4 such as methyl or ethyl.

[0057] 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 in mixture: OAM .X § y ) 1 X 'SH OY ô HY c (II) (il')

[0058] In formula (II) and (II'), Ri and R3 have the same meaning as Ri and R3 for the compounds of formula (I) and (I'), and X denotes an alkylene radical -(CH2)n- with n being an integer from 1 to 10 inclusive, preferably from 1 to 6, more preferably from 1 to 4, such that 1, preferably, R3 represents a hydrogen atom.

[0059] 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: No. Structure Chemical Name CAS No. 1 $ N-ethyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-75-5 2 Y ......SX \y N-methyl-2-thioxo-1,2-dihydroxydropyridine-3-carboxamide 91859-74-4 3 N-octyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-77-7 4 X * f'"' N-benzyl-2-thioxo-1,2-dihydroxydropyridine-3-carboxamide 91859-79-9 5 # xx ----k --VY \x. x^ N-phenyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 104857-16-1 6 ï; E H H N-cyclohexyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-78-8 7 h r ji L .-K N- [2- (4-méthoxyphény l)é thy 1] -2-thioxo-1,2-d ihydropyridine-3-carbo xamide 923682-88-6 8 X •m ^>LX .5^ ,.A, k if N-(2-méthylpropyl)-2-t hioxo-1,2-dihydropyrid ine- 3 -carboxamide 1100027-79 -9 9 •••‘ "■•\-y''" XV“"’ X^-'‘ :• H ■■W'’'' ' ■ x 's N-pentyl-2-thioxo-1,2-dihydropyridine-3-carb oxamide 330667-57-7 10 ■ yly N-nonyl-2-thioxo-1,2-d ihydropyridine-3-carbo xamide 1031149-44 -6 11 Y=xx \ / / \ / / ( y N-(2-hydroxyéthyl)-2-t hioxo-1,2-dihydropyrid ine- 3 -carboxamide 12 □ is | X<*S '''CHs N,N-diethyl 2-mercapt onicotinamide 13 YZ Y — ■ : \ x—œ YY N-ethyl-N-(2-hydroxyethyl)-2-thioxo-1,2-dihydroxydropyridine-3-carbamide 14 : ,L\.^ .-^ K .' . -¼ ' ' ■ N-(2,3-dihydroxypropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 15 0 r'' N-(1,3-dihydroxypropan-2-yl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 16 a CHj ''W'" "^s \ H / N- [(2-thioxo-1,2-dihydropyridine-3-yl)carbonyl]ethyl alaninate 17 S-^ 1 :i ' N- [(2-thioxo-1,2-dihydropyridine-3-yl)carbonyl]ethyl phenyl alaninate 18 'N" N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 19 î-i N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl ]ethyl glycinate 20 IL ÜH CI " f N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine 21 «.j! ffYVY CK OH H N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl] glycine 22 .^¾. ^yr* ^yr x N,N-bis(2-hydroxyethyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 23 O. a. Jl '<-'1 N-(3-methoxypropyl)-2 -thioxo-1,2-dihydropyridine- 3 -carboxamide 24 $ H N-butyl-2-thioxo-1,2-d ihydropyridine-3-carbo xamide

[0060] Among these compounds, the following compounds are particularly preferred: Structure No. Chemical Name CAS No. 1 .jX x' pf Y * Ys H N-ethyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-75-5 2 .............. N-methyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-74-4 4 N-benzyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-79-9 6 ,.--s .-YY -XJX sy 'N ■■ h MH N-cyclohexyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-78-8 7 Ç- zX" XH- zx P '1 H N- [2- (4-methoxyphenyl)e thy 1] -2-thioxo-1,2-d ihydropyridine-3-carbo xamide 923682-88-6 9 >x, Y^::- N-pentyl-2-thioxo-1,2-dihydropyridine-3-carb oxamide 330667-57-7 11 Ü 7 À YY 'v5 fi N-(2-hydroxyethyl)-2-t hioxo-1,2-dihydropyrid ine-3-carboxamide 12 ( T T.”" iÀ N,N-diethyl 2-mercapt onicotinamide 14 J*- z'0H N-(2,3-dihydroxypropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 15 _.Zx. M Â .OH N-(1,3-dihydroxypropan-2-yl)-2-thioxo-1,2-dihydropyridine-3-carboxamide 16 \ M î' h3c N- [(2-thioxo-1,2-dihydropyridine-3-yl)carbonyl]ethyl alaninate 17 v- A, N- [(2-thioxo-1,2-dihydropyridine-3-yl)carbonyl]ethyl phenyl alaninate 18 p T zx'5>'' ""'N - ethyl N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate 19 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 20 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine 21 CH. GH H N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine

[0061] More preferably, among these compounds, the following compounds are particularly preferred: Structure No. Chemical Name CAS No. 1 H N-ethyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 91859-75-5 9 C: x-xyy>'' $ H N-pentyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 330667-57-7 16 .XY * jj ? Y"" Y \ H / N- [(2-thioxo-1,2-dihydropyridine-3-yl)carbonyl ]ethyl alaninate 18 N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 19 N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 20 _ 1 [Q r ï AC N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycine 21 / Vo / " \ Y 'O N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl] glycine Even more preferably, among these compounds, the following compounds are more

[0062] particularly preferred: No. Structure Chemical Name CAS No. 18 . I ,o ( Y" YTH OY N-methyl-N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 19 G t J - ''■'N'"' H N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl ]ethyl glycinate

[0063] In a most preferred embodiment, the compound according to the present invention is as follows: 20 THERE s >5 N-[(2-thioxo-1,2-dihyd ropyridin-3-yl)carbony l]glycine

[0064] All the above compounds can be obtained by a chemical process known to those skilled in the art, from commercially available reagents.

[0065] The thiopyridinone compound (1) can be prepared in accordance with the process described, for example, in document EP-A-3390363 or WO 2017 / 102349, which is incorporated by reference.

[0066] The compound thiopyridinone (1) can be an active ingredient or active compound in cosmetic or dermatological products. The term "active ingredient" or "active compound" used here refers to an ingredient or compound that has an active cosmetic or dermatological property, such as antioxidant, bleaching, UV-filtering, and antibacterial effects. The compound thiopyridinone (1) used in the present invention can function as a depigmenting, bleaching, or bleaching agent, and thus the composition according to the present invention can be used as a bleaching product or as a cosmetic composition for bleaching keratinous material.

[0067] The compound thiopyridinone (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 to remove pigmentation spots or age spots, and / or as an anti-tanning agent.

[0068] 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. weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.

[0069] Furthermore, the quantity of the thiopyridinone compound(s) (1) in the composition according to the present invention may be 10% by weight or less, preferably 6% by weight or less, and more preferably 4% by weight or less, relative to the total weight of the composition.

[0070] The quantity 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 6% by weight, more preferably from 0.1% to 4% by weight, relative to the total weight of the composition. Scleroglucan gums

[0071] The composition according to the invention comprises one or more scleroglucan gums.

[0072] Scleroglucan gum(s) are polysaccharides of microbial origin produced by a Sclerotium-type fungus, in particular Sclerotium rolfsii. They are polysaccharides consisting solely of glucose units.

[0073] The scleroglucan gum(s) may or may not be modified. Preferably, the scleroglucan gum(s) used in the present invention are unmodified.

[0074] Examples of scleroglucan gums usable in the present invention are, without limitation, the products sold under the name ACTIGUM CS, in particular ACTIGUM CS 11, by the company SANOFI BIO INDUSTRIES and under the name AMIGUM or AMIGEL by the company ALBAN MULLER INTERNATIONAL.

[0075] Other scleroglucan gums, such as that treated with glyoxal described in French patent application no. 2 633 940, may also be used.

[0076] The scleroglucan gum(s) may be present in the composition according to the invention in a total content ranging from 0.01 to 10% by weight, more preferably from 0.05 to 5% by weight, and even more preferably from 0.1 to 3% by weight relative to the total weight of the composition. Lipophilic acrylic polymer

[0077] According to a particular embodiment of the invention, the composition further comprises at least one suitably selected lipophilic acrylic polymer.

[0078] The lipophilic acrylic polymer(s) that may be present in the composition according to the invention comprises monomeric units of formulas (A) and (B): in which: RI, independently of each other, is chosen from among the alkyl or alkenyl radicals, and at least 60% by weight of the RI groups are radicals selected from stearyl and behenyl radicals, the weight percentage referring to the sum of all RI groups present in the polymer, and the weight ratio of the sum of all hydroxyethyl acrylate units to the sum of all acrylate units bearing the RI group ranges from 1:30 to 1:1, and the sum of the total of units A and B is at least 95% by weight of the total weight of the polymer.

[0079] Preferably, RI consists of alkyl radicals, preferably alkyl radicals in Ci6-C22, and more preferably stearyl radicals (in Ci8) or behenyl radicals (in C22).

[0080] Preferably, at least 70% by weight of the RI groups are stearyl or behenyl radicals, preferably at least 80% by weight, more preferably at least 90% by weight.

[0081] According to a preferred embodiment, all RI groups are behenyl radicals.

[0082] According to another preferred embodiment, all RI groups are stearyl radicals.

[0083] Preferably, the weight ratio of the sum of all hydroxyethyl acrylate units to the sum of all acrylate units bearing the RI group goes from 1:15 to 1:1, preferably goes from 1:10 to 1:4.

[0084] Advantageously, the polymeric units present in the polymer consist of the units (A) and (B) described previously.

[0085] The polymer has a number-average molecular weight (Mn) ranging from 2,000 to 9,000 g / mol, preferably ranging from 5,000 to 9,000 g / mol. The number-average molecular weight can be measured using gel permeation chromatography, for example according to the method described in the example below.

[0086] Preferably, the polymer has a melting temperature ranging from 40 °C to 70 °C, and preferably from 45 °C to 67 °C. The melting temperature is measured by differential scanning calorimetry (DSC), for example according to the method described in the example below.

[0087] According to a first embodiment, when the polymer is such that at least 60% by weight of the RI groups are stearyl radicals, then the polymer preferably has a melting point ranging from 40 to 60 °C, and preferably ranging from 45 to 55 °C.

[0088] According to a second embodiment, when the polymer is such that at least 60% by weight of the RI groups are behenyl radicals, then the polymer has a melting temperature ranging from 60 °C to 70 °C, and preferably from 63 °C to 67 °C.

[0089] The polymer used according to the invention can be prepared by polymerization of a monomer of the following formula: CH2=CH-COO-R1, RI having the meaning described above, and 2-hydroxyethyl acrylate.

[0090] Polymerization can be carried out according to known methods, such as solution polymerization or emulsion polymerization.

[0091] Polymerization is described for example in US document 2007 / 0264204.

[0092] The lipophilic acrylic polymer can be present in the composition according to the invention in an active material content ranging from 0.05 to 10% by weight, relative to the total weight of the composition, preferably ranging from 0.1 to 5% by weight, and better ranging from 0.2 to 2% by weight. UV filters

[0093] According to a particular embodiment of the invention, the composition according to the invention comprises at least one UV filter.

[0094] The UV filter(s) may in particular be chosen from among organic UV filters, and in particular hydrophilic organic UV filters, such as water-soluble organic UV filters and water-dispersible organic UV filters, and lipophilic organic UV filters.

[0095] By "water-soluble organic UV filter" is meant any organic filter capable of being totally dissolved in molecular form in a liquid aqueous phase.

[0096] By "hydrodispersible organic UV filter" is meant any organic UV filter capable of forming in a liquid aqueous phase a homogeneous suspension of particles with a volume average size of less than 100 microns. The volume average size is determined by laser diffraction particle size analysis.

[0097] By "lipophilic organic UV filter" is meant any organic filter capable of being completely dissolved in a molecular state in a liquid oil phase or to be solubilized in colloidal form (for example in micellar form) in a liquid oil phase.

[0098] By "organic UVA filter" is meant any organic chemical molecule capable of absorbing at least UVA radiation in the wavelength range between 320 and 400 nm; said molecule also being able to absorb UVB radiation in the wavelength range between 280 and 320 nm.

[0099] By "organic UVB filter" is meant any organic chemical molecule capable of absorbing mainly UVB radiation in the range of wavelengths between 280 and 320 nm. Water-soluble organic UV filters

[0100] The composition according to the invention may include at least one water-soluble organic UV filter.

[0101] Among the water-soluble organic filters capable of absorbing UVA, the following may be mentioned: - the compound with INCI name Terephthalylidene Dicamphor Sulfonic Acid manufactured under the name "MEXORYL SX" by NOVEAL; - bis-benzoazolyl derivatives as described in EP 669 323, and US 2,463,264, and more particularly the compound with the INCI name Disodium Phenyl Dibenzimidazole Tetrasulfonate sold under the trade name "NEO HELIOPAN AP" by SYMRISE.

[0102] The water-soluble organic filter may also be a mixed water-soluble filter capable of absorbing both UVA and UVB rays. Preferably, such a mixed filter is a benzophenone derivative containing at least one sulfonic acid radical, such as, in particular: Benzophenone-4 sold under the trade name "UVINUL® MS40" by BASF, Benzophenone-5, and Benzophenone-9.

[0103] According to a particular embodiment of the invention, the water-soluble organic filter(s) capable of absorbing UVA are chosen from Terephthalylidene Dicamphor Sulfonic Acid, bis-benzoazolyl derivatives, in particular Disodium Phenyl Dibenzimidazole Tetrasulfonate, Benzophenone-4, Benzophenone-5, Benzophenone-9 and mixtures thereof.

[0104] Preferably, the water-soluble organic filter(s) capable of absorbing UVA are selected from Terephthalylidene Dicamphor Sulfonic Acid, Disodium Phenyl Dibenzimidazole Tetrasulfonate, Benzophenone-4, Benzophenone-5, Benzophenone-9 and mixtures thereof.

[0105] Even more preferably, the water-soluble organic filter(s) capable of absorbing UVA are chosen from Terephthalylidene Dicamphor Sulfonic Acid, bis-benzoazolyl derivatives, in particular Disodium Phenyl Dibenzimidazole Tetrasulfonate, and mixtures thereof.

[0106] Preferably, the water-soluble organic filter(s) capable of absorbing UVA is chosen from Terephthalylidene Dicamphor Sulfonic Acid, Disodium Phenyl Dibenzimidazole Tetrasulfonate, and mixtures thereof.

[0107] According to a first preferred embodiment, the water-soluble organic filter capable of absorbing UVA is Terephthalylidene Dicamphor Sulfonic Acid (also called Ecamsule).

[0108] According to a second preferred embodiment, the water-soluble organic filter capable of absorbing UVA is Disodium Phenyl Dibenzimidazole Tetrasulfonate (also called Bisdisulizole Disodium).

[0109] The water-soluble organic UVB filter(s) usable according to the present invention may be selected from water-soluble cinnamic derivatives such as ferulic acid or 3-methoxy-4-hydroxycinnamic acid; water-soluble benzylidene camphor compounds; water-soluble phenylbenzimidazole compounds; water-soluble p-aminobenzoic compounds (PABA), Glyceryl PABA or PEG-25 PABA sold under the name "UVINUL® P25" by BASF; water-soluble salicylic compounds, Benzylidene Camphor Sulfonic Acid manufactured under the name "MEXORYL SL" by NOVEAL, Camphor Benzalkonium Methosulfate manufactured under the name "MEXORYL SO" by NOVEAL, and mixtures thereof.

[0110] Preferred examples of water-soluble organic UVB filters include phenylbenzimidazole compounds, such as 2-phenyl-1H-benzimidazole-5-sulfonic acid (INCI name: phenylbenzimidazole sulfonic acid) sold in particular under the trade name "EUSOLEX 232®" by MERCK.

[0111] According to a preferred embodiment, the water-soluble organic filter capable of absorbing UVB is Phenylbenzimidazole Sulfonic Acid (also called Ensulizole). Water-dispersible organic UV filters

[0112] The hydrodispersible organic UV filter(s) can be selected from the following compounds.

[0113] Methylene bis-(hydroxyphenyl benzotriazole) compounds:

[0114] Methylene bis-Benzotriazolyl Tetramethylbutylphenol in the form of an aqueous dispersion of micronized particles having a volume average particle size ranging from 0.01 to 5 pm, and more preferably from 0.01 to 2 pm, and more particularly from 0.020 to 2 pm, with at least one alkylpolyglycoside surfactant of structure CnH2n+iO(C6HiO5)xH in which n is an integer from 8 to 16 and x is the average degree of polymerization of the unit (C6HiO5) and ranges from 1.4 to 1.6 such that the aqueous dispersions described in patent GB-A-2 303 549, in particular the product sold under the trade name "TINOSORB® M" by BASF, or in the form of an aqueous dispersion of micronized particles having a volume average particle size ranging from 0.02 to 2 pm, and more preferably from 0.01 to 1.5 pm, and more particularly from 0.02 to 1 pm, in the presence of at least one mono-(C8-C2o)alkyl-ester of polyglycerol having a degree of glycerol polymerization of at least 5 such as the aqueous dispersions described in application WO2009 / 063392, in particular the product marketed under the name Tinosorb WPGL by BASF, Triazine compounds#:

[0115] - 3,3'-(l,4-Phenylene)bis(5,6-diphenyl-l,2,4-triazine), INCI name Phenylene Bis-Diphenyl triazine, notably marketed under the name Triasorb by Pierre Fabre; - Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine in its water-dispersible form, INCI name Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine (and) Acrylates / C12-22 Alkyl Methacrylate Copolymer, under the trade name TINOSORB® S LiteAqua by BASF, - symmetric triazine filters substituted with naphthalenyl groups or polyphenyl groups used in micronized form (average particle size of 0.02 to 3 pm) which can be obtained for example by the micronization process described in applications GB-A-2 303 549 and EP-A-893119, and in particular in aqueous dispersion form, in particular 2,4,6-tris(bi-phenyl)-triazine and 2,4,6-tris(ter-phenyl)-triazine marketed under the name TINOSORB® A2B by BASF and which is covered in patent applications WO06 / 035000, WO06 / 034982, WO06 / 034991, WO06 / 035007, WO2006 / 034992, WO2006 / 034985.

[0116] Among the water-dispersible organic UV filters, the following filters can also be mentioned: Benzophenone compounds#:

[0117] 1,1 '-(1,4-piperazinediyl)bis [1 - [2- [4-(diethylamino)-2-hydroxybenzoyl]phenyl] - Methanone (CAS 919803-06-8) as described in application WO2007 / 071584; this compound being advantageously used in micronized form (average volume size of 0.02 to 2 µm) which can be obtained, for example, by the micronization process described in applications GB-A-2 303 549 and EP-A-893119 and in particular in aqueous dispersion form, Benzoxazole compounds#:

[0118] 2-[4-(l,3-benzoxazol-2-yl)phenyl]-l,3-benzoxazole, of cas number 904-39-2. Lipophilic organic UV filters

[0119] The lipophilic organic filter(s) may be selected from cinnamic compounds; anthranilate compounds; salicylic compounds; dibenzoylmethane compounds; benzylidene camphor compounds; benzophenone compounds; [3,[3-diphenylacrylate] compounds; triazine compounds; benzotriazole compounds; benzalmalonate compounds, in particular those cited in US patent 5624663; benzimidazole derivatives; imidazoline compounds; bis-benzoazolyl compounds as described in patents EP669323 and US 2,463,264; methylene bis-(hydroxyphenyl benzotriazole) compounds as described in applications US 5,237,071, US 5,166,355, GB2303549, DE 197 26 184 and EP893119; benzoxazole compounds as described in patent applications EP0832642, EP1027883, EP1300137 and DE10162844; filter polymers and filter silicones such as those described in particular in application WO-93 / 04665;α-Alkylstyrene-derived dimers such as those described in patent application DE19855649; 4,4-Diarylbutadiene compounds such as those described in applications EP0967200, DE19746654, DE19755649, EP-A-1008586, EPI 133980 and EP133981 and mixtures thereof.

[0120] Preferably, the lipophilic organic filter(s) are chosen from salicylic compounds, dibenzoylmethane compounds, benzylidene camphor compounds; benzophenone compounds; triazine compounds; benzotriazole compounds; and mixtures thereof.

[0121] Examples of lipophilic organic photoprotective agents include those designated below by their INCI name and / or chemical name. Cinnamic compounds:

[0122] Ethylhexyl Methoxycinnamate sold in particular under the trade name PARSOL® MCX by the company DSM Nutritional Products; Isoamyl p-Methoxycinnamate sold under the trade name NEO HELIOPAN E 1000 ® by the company Symrise, Dibenzoylmethane compounds:

[0123] Butyl Methoxydibenzoylmethane (or avobenzone) sold notably under the trade name PARSOL® 1789 by DSM Nutritional Products, Salicylic compounds#:

[0124] Homosalate sold under the name "Parsol® HMS" by DSM Nutritional Products, Ethylhexyl Salicylate sold under the name "NEO HELIOPAN® OS" by Symrise, P,P-diphenylacrylate compounds#:

[0125] Octocrylene sold in particular under the trade name “UVINUL® N 539 T” by BASF, Benzophenone compounds#:

[0126] Benzophenone-3 or Oxybenzone, sold under the trade name "UVINUL® M 40" by BASF, Diethylamino hydroxybenzoyl hexyl benzoate sold under the trade name "UVINUL® A Plus" or in a mixture with ethylhexyl methoxycinnamate under the trade name "UVINUL® A Plus B" by BASF, Benzylidene camphor compounds#:

[0127] 4-Methylbenzylidene camphor sold under the name “EUSOLEX® 6300” by the company MERCK, Phenyl benzotriazole compounds#:

[0128] Drometrizole Trisiloxane manufactured under the name “MEXORYL® XL” by the company NOVEAL,

[0129] Methylene bis-(hydroxyphenyl benzotriazole) compounds:

[0130] Methylene bis-Benzotriazolyl Tetramethylbutylphenol, particularly in solid form as the product sold under the trade name "MIXXIM BB / 100 ®" by FAIRMOUNT CHEMICAL, Triazine compounds#:

[0131] - Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine sold under the trade name “TINOSORB® S” by the company BASF, - Ethylhexyl Triazone, sold notably under the trade name "UVINUL® T 150" by BASF, - Diethylhexyl Butamido Triazone sold under the trade name "UVASORB® HEB" by the company 3V SIGMA, - Symmetrical triazine filters substituted with naphthalenyl groups or polyphenyl groups described in US patent 6,225,467, application WO2004 / 085412 (see compounds 6 and 9) or the document "Symetrical Triazine Derivatives" IP.COM Journal, INC WEST HENRIETTA, NY, US (September 20, 2004), Anthranilic Compounds#:

[0132] Menthyl anthranilate sold under the trade name "NEO HELIOPAN® MA" by Symrise, Benzalmalonate Compounds#:

[0133] Benzalmalonate-function polyorganosiloxane such as Polysilicone-15 sold under the trade name “PARSOL SLX ®” by DSM NUTRITIONAL PRODUCTS.

[0134] According to a particular embodiment of the invention, the UV filter(s) are chosen from among organic UV filters.

[0135] According to a first preferred embodiment of the invention, the organic UV filter(s) are chosen from among hydrophilic organic UV filters such as water-soluble organic UV filters and water-dispersible organic UV filters, preferably water-soluble organic UV filters.

[0136] According to a second preferred embodiment of the invention, the organic UV filter(s) are selected from among lipophilic organic UV filters, preferably selected from Diethylamino hydroxybenzoyl hexyl benzoate (in particular sold under the trade name "UVINUL® A Plus" or in a mixture with ethylhexyl methoxycinnamate under the trade name "UVINUL® A Plus B" by BASF), Drometrizole Trisiloxane (in particular manufactured under the name "MEXORYL® XL" by NOVEAL), Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine (in particular sold under the trade name "TINOSORB® S" by BASF), Ethylhexyl Triazone (sold in particular under the trade name "UVINUL® T 150" by BASF), and BUTYL METHOXYDIBENZOYLME THANE (sold in particular under the trade name "PARSOL"). 1789 ® » by DSM NUTRITIONAL PRODUCTS).

[0137] The UV filter(s) may be present in an amount of between 0.2% and 30% by weight, preferably between 0.5% and 25% by weight, preferably between 1% and 20% by weight, and even more preferably between 1.5% and 18% by weight relative to the total weight of composition.

[0138] According to another embodiment of the invention, the UV filter(s) are present in an amount of less than 15% by weight, preferably less than 10% by weight, even more preferably less than 5% by weight, better less than 3% by weight, and even better less than 1% by weight relative to the total weight of composition. Aqueous phase

[0139] According to a particular embodiment, the composition according to the invention comprises at least one aqueous phase.

[0140] According to a preferred embodiment, the composition according to the invention comprises at least one aqueous phase comprising at least water.

[0141] The aqueous phase may also comprise at least one other organic solvent soluble in water at 25 °C, chosen for example from: - C1-C4 monoalkanols. A "CrC4 monoalkanol" is defined as any saturated, linear or branched alkane compound having 1 to 4 carbon atoms and a single hydroxyl (OH) group. The Ci-C4 monoalkanol(s) present The components of the compositions of the invention may be chosen from methanol, ethanol, propanol, isopropanol, butanol, or mixtures thereof. Ethanol will be chosen more particularly; - polyols having in particular from 2 to 20 carbon atoms, preferably from 2 to 6 carbon atoms, such as glycerol, diglycerol, propylene glycol, isoprene glycol, dipropylene glycol, butylene glycol, hexylene glycol, 1,2-propanediol, 1,3-propanediol, pentylene glycol, caprylyl glycol, simple sugars, water-soluble polyalkylene glycols; and - their mixtures.

[0142] The monoalkanol(s) may be present at concentrations ranging from 0.2 to 90% by weight, more preferably from 0.5 to 50% by weight, and preferably from 1% to 10% by weight relative to the total weight of the composition.

[0143] According to a particular embodiment, the composition according to the invention comprises at least one polyol, in particular as described above. The presence of at least one polyol notably improves cosmetic properties, such as smoothness upon application, and reduces stickiness. Preferably, it comprises at least 0.5% by weight of polyols relative to the total weight of the composition, preferably at least 1% by weight of polyols relative to the total weight of the composition, preferably at least 3% by weight of polyols relative to the total weight of the composition, preferably at least 5% by weight of polyols relative to the total weight of the composition, preferably from 10% to 50% by weight, preferably from 15% to 40% by weight, preferably from 18% to 35% by weight, and even more preferably from 20% to 30% by weight.

[0144] Preferably, the composition according to the invention comprises a polyol, preferably glycerin, butylene glycol, propylene glycol, 1,2-propanediol, caprylyl glycol, pentylene glycol or dipropylene glycol and mixtures thereof.

[0145] According to a particular embodiment, the cosmetic composition according to the invention may comprise an acid and / or a base.

[0146] Examples of acidifying agents include mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, and sulfonic acids.

[0147] Examples of alkalizing agents include ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, sodium or potassium hydroxides.

[0148] Preferably, the cosmetic composition comprises one or more alkalizing agents selected from alkanolamines, in particular triethanolamine, and sodium hydroxide.

[0149] According to a particular embodiment, the composition according to the invention has a pH between 4 and 10, preferably between 5 and 8.5, and preferably between 5.5 and 8.

[0150] The pH measurement of the composition according to the invention can be carried out using a Mettler Toledo MPC227, SevenEasy pH or SevenGo SG2 pH meter, at room temperature (25 °C) and atmospheric pressure.

[0151] According to a particular embodiment of the invention, the overall aqueous phase, including all hydrophilic substances of the composition capable of being solubilized in this same phase, including hydrophilic filters and the thiopyridinone compound(s) as defined above, represents from 5% to 100% by weight, and preferably from 30% to 80% by weight relative to the total weight of the composition.

[0152] The composition preferably comprises at least 5% by weight of water relative to the total weight of the composition, preferably from 10% to 99% by weight, even more preferably from 20% to 90% by weight, better from 30% to 80% by weight, and even better from 40% to 70% by weight relative to the total weight of the composition. Fat phase

[0153] According to a particular embodiment, the composition according to the invention comprises at least one fatty phase.

[0154] The oil phase may consist of any oily substances commonly used in cosmetics or dermatology. It may include at least one oil. The oil phase also includes the lipophilic filter(s) present in the composition.

[0155] The term "oil" refers to any fatty substance in liquid form at ambient temperature (20-25 °C) and atmospheric pressure (760 mm Hg). These oils may be volatile or non-volatile.

[0156] For the purposes of this invention, "volatile oil" means an oil capable of evaporating upon contact with the skin or keratin fiber in less than one hour, at ambient temperature and atmospheric pressure. The volatile oil(s) of the invention are volatile cosmetic oils, liquid at ambient temperature, having a non-zero vapor pressure, at ambient temperature and atmospheric pressure, ranging in particular from 0.13 Pa to 40,000 Pa (103 to 300 mm Hg), in particular ranging from 1.3 Pa to 13,000 Pa (0.01 to 100 mm Hg), and more particularly ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mm Hg).

[0157] By "non-volatile oil" is meant an oil that remains on the skin or keratin fiber at room temperature and atmospheric pressure for at least several hours and having in particular a vapor pressure of less than 103 mm of Hg (0.13 Pa).

[0158] For the purposes of this invention, "hydrocarbon oil" means any oil consisting mainly of carbon and hydrogen atoms, and optionally one or more heteroatoms, in particular nitrogen and oxygen. Thus, these oils may notably contain one or more ester, ether, fluorine, carboxylic acid and / or alcohol groups.

[0159] The term “siliconized oil” means an oil comprising at least one silicon atom, and in particular at least one Si-O group.

[0160] Examples of non-volatile hydrocarbon oils that can be used according to the invention include: (i) vegetable hydrocarbon oils such as glyceride triesters, which are generally triesters of fatty acids and glycerol, the fatty acids of which may have chain lengths ranging from C4 to C24, the latter being linear or branched, saturated or unsaturated; these oils include wheat germ, sunflower, grape seed, sesame, maize, apricot, castor, shea, avocado, olive, soybean, sweet almond, palm, rapeseed, cottonseed, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, sesame, squash, rapeseed, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower, candlenut, passionflower, and rosehip oils; or even the triglycerides of caprylic / capric acids such as those sold by the company Stéarineries Dubois or those sold under the names Miglyol 810®, 812® and 818® by the company Dynamit Nobel; (ii) synthetic ethers having 10 to 40 carbon atoms; (iii) linear or branched hydrocarbons, of mineral or synthetic origin such as petroleum jelly, polydecenes, hydrogenated polyisobutene such as paream, squalane, and mixtures thereof; (iv) synthetic esters such as oils of the formula RCOOR' in which R represents the remainder of a linear or branched fatty acid comprising from 1 to 40 carbon atoms and R' represents a hydrocarbon chain, particularly a branched one, containing from 1 to 40 carbon atoms, provided that R + R' is >10, such as, for example, Purcellin oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, C12-C15 alcohol benzoates such as the product sold under the trade name "Finsolv TN®" or "Witconol TN®" by WITCO or "TEGOSOFT TN®" by EVONIK GOLDSCHMIDT, 2-ethylphenyl benzoate such as the commercial product sold under the name "X-TEND 226®" by ISP, isopropyl lanolate, hexyl laurate, diisopropyl adipate, isononyl isononanoate, oleyl erucate, 2-ethyl palmitate hexyl, isostearyl isostearate, diisopropyl sebacate such as the product sold under the name "Dub Dis" by the company Stearinerie Dubois, octanoates, decanoates or ricinoleates of alcohols or polyalcohols such as propylene glycol dioctanoate; hydroxylated esters such as isostearyl lactate, di-isostearyl malate; and esters of pentaerythritol; citrates or tartrates such as linear C12-C13 dialkyl tartrates such as those sold under the name COSMACOL ETI® by the company ENICHEM AUGUSTA INDUSTRIALE as well as linear C14-C15 dialkyl tartrates such as those sold under the name COSMACOL ETL® by the same company; acetates; (v) fatty alcohols that are liquid at room temperature with a branched and / or unsaturated carbon chain having 12 to 26 carbon atoms such as octyl dodecanol, isostearyl alcohol, oleic alcohol, 2-hexyldecanol, 2-butyloctanol, 2-undecylpentadecanol; (vi) higher C12-C22 fatty acids, such as oleic acid, linoleic acid, linolenic acid; (vii) carbonates such as dicaprylyl carbonate such as the product sold under the name “Cetiol CC®” by the company Cognis; and their mixtures.

[0161] Among the non-volatile hydrocarbon oils usable according to the invention, glyceride triesters, and in particular caprylic / capric acid triglycerides, synthetic esters, and in particular diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate, dicaprylyl carbonate, isononyl isononanoate, oleyl erucate, C12-C15 alcohol benzoate, 2-ethylphenyl benzoate, and fatty alcohols, in particular octyldodecanol, are preferred. Preferably, the non-volatile hydrocarbon oils are chosen from diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate, and dicaprylyl carbonate.

[0162] Examples of usable volatile hydrocarbon oils according to the invention include hydrocarbon oils having 8 to 16 carbon atoms, and in particular C8-C16 branched alkanes such as C8-C16 petroleum-derived isoalkanes (also called isoparaffins) such as isododecane (also called 2,2,4,4,6-pentamethylheptane), isodecane, isohexadecane, oils sold under the trade names Isopars or Permetyls, C8-C16 branched esters, isohexyl neopentanoate, and mixtures thereof.

[0163] We can also mention the alkanes described in Cognis patent applications WO 2007 / 068371 and WO 2008 / 155059 (mixtures of distinct alkanes differing by at least one carbon atom). These alkanes are obtained from fatty alcohols, themselves obtained from coconut or palm oil. Examples include the mixtures of n-undecane (Cl 1) and n-tridecane (Cl 3) obtained in Examples 1 and 2 of the application. WO2008 / 155059 from Cognis Company. We can also mention n-dodecane (C12) and n-tetradecane (C14) sold by Sasol respectively under the references PARAFOL 12-97 and PARAFOL 14-97®, as well as their mixtures.

[0164] Other volatile hydrocarbon oils, such as petroleum distillates, particularly those sold under the name Shell Soit® by the Shell company, can also be used. In one embodiment, the volatile solvent is selected from volatile hydrocarbon oils having 8 to 16 carbon atoms and mixtures thereof.

[0165] Non-volatile silicone oils may be selected in particular from non-volatile polydimethylsiloxanes (PDMS), polydimethylsiloxanes having alkyl or alkoxy groups, during and / or at the end of the silicone chain, each group having from 2 to 24 carbon atoms, phenyl silicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, 2-phenylethyl trimethylsiloxysilicates.

[0166] Examples of volatile silicone oils include, for instance, volatile linear or cyclic silicone oils, particularly those with a viscosity < 8 centistokes (8 x 10⁶ m² / s), and having, in particular, 2 to 7 silicon atoms, these silicones possibly comprising alkyl or alkoxy groups having 1 to 10 carbon atoms. Examples of volatile silicone oils usable in the invention include, in particular, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, and mixtures thereof.

[0167] We can also mention volatile linear alkyltrisiloxane oils such as: 3-butyl 1,1,1,3,5,5,5-heptamethyl trisiloxane, 3-propyl 1,1,1,3,5,5,5-heptamethyl trisiloxane, and 3-ethyl 1,1,1,3,5,5,5-heptamethyl trisiloxane.

[0168] Fluorinated volatile oils, such as nonafluoromethoxybutane, decafluoropentane, tetradecafluorohexane, dodecafluoropentane and mixtures thereof, may also be used.

[0169] The oily phase according to the invention may further comprise, mixed with or solubilized in the oil, other fatty substances.

[0170] Another fatty substance that may be present in the oily phase may be, for example: - a fatty acid chosen from among fatty acids having 8 to 30 carbon atoms different from fatty chain amino acids as defined above, such as stearic acid, lauric acid, palmitic acid and oleic acid; - a gum chosen from among the silicone gums (dimethiconol), - a pasty compound, such as polymeric or non-polymer silicone compounds, esters of an oligomeric glycerol, arachidyl propionate, fatty acid triglycerides and their derivatives, - and mixtures thereof.

[0171] According to a particular embodiment of the invention, the overall oily phase, including all the lipophilic substances of the composition capable of being solubilized in this same phase, including the lipophilic filters, represents from 0% to 90% by weight, and preferably from 20% to 70% by weight relative to the total weight of the composition. Active cosmetic ingredients

[0172] The composition of the present invention may include at least one cosmetic active ingredient.

[0173] Examples of cosmetic actives include moisturizing agents; natural extracts; vitamins and their derivatives; alpha-hydroxy acids; retinoids; extracts of algae, fungi, plants, yeasts and bacteria; enzymes; tightening agents; agents acting on microcirculation, and mixtures thereof.

[0174] It is easy for a person skilled in the art to adjust the quantity of cosmetic active ingredient according to the end use of the composition according to the present invention. Additional adjuvants or additives

[0175] The composition of the present invention may also include conventional cosmetic adjuvants or additives, for example perfumes, chelating agents, preservatives and bactericides, additional thickeners, pH regulators, additional fillers, and mixtures thereof.

[0176] A person skilled in the art can select the quantity of additional adjuvants or additives so as not to impair the final use of the composition according to the present invention. Pharmaceutical forms

[0177] According to a particular embodiment, the compositions according to the invention have a viscosity of at least 0.10 Pa.s, measured at 25 °C and under atmospheric pressure with a Lamy Rheology Rhéomat RM 100® viscometer after 10 minutes of measurement. Preferably, it is between 0.10 and 20 Pa.s, more preferably between 0.10 and 10 Pa.s, and better still between 0.10 and 5 Pa.s.

[0178] Such viscosity typically allows compositions to have a gel-like texture.

[0179] The compositions according to the invention can be prepared according to techniques well known to those skilled in the art.

[0180] The compositions according to the invention may be in aqueous form, for example in the form of an aqueous gel or hydroalcoholic composition, but also in the form of an emulsion, in particular an oil-in-water or water-in-oil emulsion, or a biphasic.

[0181] According to a particular embodiment, the composition of the invention does not comprise an oily phase. Preferably, the compositions according to the invention are oil-free. For the purposes of the invention, the term "oil-free" refers to a composition comprising a single liquid phase that is an aqueous phase (a liquid phase comprising water). The term "oil" does not cover, for example, water-soluble active ingredients, water-soluble or water-dispersible UV filters, and water-soluble glycols.

[0182] According to another particular embodiment, the composition according to the invention is in the form of an emulsion. When the composition according to the invention is in the form of an oil-in-water emulsion, it comprises an oily phase dispersed in an aqueous phase. When the composition according to the invention is in the form of a water-in-oil emulsion, it comprises an aqueous phase dispersed in an oily phase.

[0183] In the case of compositions in the form of oil-in-water or water-in-oil emulsions, the emulsification processes that can be used are of the blade or propeller type, rotor-stator and HHP.

[0184] It is also possible, by HHP (between 50 and 800 bars), to obtain stable dispersions with droplet sizes down to 100 nm.

[0185] Emulsions may generally contain at least one emulsifier selected from amphoteric, anionic, cationic, or nonionic emulsifiers, used alone or in mixtures. The emulsifiers are chosen appropriately according to the emulsion to be obtained (W / O or W / O).

[0186] Examples of non-ionic W / O emulsifying surfactants include alkyl esters or ethers of sorbitan, glycerol, polyol, glycerol or sugars; silicone surfactants such as dimethicone copolyols like the mixture of cyclomethicone and dimethicone copolyol sold under the name "DC 5225 C®" by Dow Corning, and alkyl-dimethicone copolyols such as Laurylmethicone copolyol sold under the name "Dow Corning 5200 Formulation Aid" by Dow Corning; Cetyl dimethicone copolyol, such as the product sold under the name Abil EM 90R® by Goldschmidt, and the mixture of cetyl dimethicone copolyol, polyglycerol isostearate (4 moles), and hexyl laurate sold under the name ABIL WE 09® by Goldschmidt. One or more co-emulsifiers may also be added, which, in turn, advantageously, can be chosen from the group comprising alkylated polyol esters.

[0187] We can also mention non-siliconized emulsifying surfactants, in particular alkyl esters or ethers of sorbitan, glycerol, polyol or sugars.

[0188] Examples of alkylated polyol esters include polyethylene glycol esters such as PEG-30 Dipolyhydroxystearate, such as the product marketed under the name Arlacel P135® by the company CRODA.

[0189] Examples of glycerol and / or sorbitan esters include polyglycerol isostearate, such as the product marketed under the name Isolan GI 34® by Goldschmidt; sorbitan isostearate, such as the product marketed under the name Arlacel 987® by CRODA; sorbitan isostearate and glycerol, such as the product marketed under the name Arlacel 986® by CRODA, and mixtures thereof.

[0190] For O / W emulsions, examples of non-ionic emulsifying surfactants include polyoxyalkylated fatty acid and glycerol esters (more particularly polyoxyethylated and / or polyoxypropylated) such as polyethylene glycol and stearic acid ester with INCI name PEG-100 STEARATE marketed under the name Myrj SIOO-PA-(SG) by CRODA; oxyalkylated fatty acid and sorbitan esters; polyoxyalkylated fatty acid esters (in particular polyoxyethylated and / or polyoxypropylated) possibly in combination with a fatty acid and glycerol ester such as the PEG-100 Stearate / Glyceryl Stearate mixture marketed for example by CRODA under the name Arlacel 165; oxyalkylated fatty alcohol ethers (oxyethylenated and / or oxypropylenated); sugar esters such as sucrose stearate; fatty alcohol and sugar ethers,including alkyl polyglucosides (APGs) such as decyl glucoside and lauryl glucoside marketed for example by Henkel under the respective names Plantaren 2000® and Plantaren 1200®, cetostearyl glucoside possibly in mixture with cetostearyl alcohol, marketed for example under the name Montanov 68® by Seppic, under the name Tegocare CG90® by Goldschmidt and under the name Emulgade KE3302® by Henkel, as well as arachidyl glucoside, for example in the form of the mixture of arachidic and behenic alcohols and arachidyl glucoside marketed under the name Montanov 202® by Seppic. According to a particular embodiment of the invention, the mixture of the alkylpolyglucoside as defined above with the corresponding fatty alcohol can be in the form of a self-emulsifying composition, as described for example in document WO-A-92 / 06778.

[0191] As examples of anionic surfactants for making O / W emulsions, we can mention surfactants chosen from amino acids modified by at least one hydrocarbon chain in C8-C30, preferably in C8-C24, and their salts, in particular acyl glutamic acids (INCI name: acyl glutamic acid) or one of their salts (acyl glutamates), such as stearoyl glutamic acid or one of its salts, in particular sodium stearoyl glutamate (INCI name).

[0192] Such compounds are marketed under the name AMISOFT by the company AJINOMOTO and in particular under the references Amisoft CA, Amisoft LA, Amisoft HS 11 PF, Amisoft MK-11, Amisoft LK-11, Amisoft CK-11, or under the name EUMULGIN SG by the company COGNIS.

[0193] As anionic surfactants for making H / W emulsions, we can also mention hydrophobic modified polysaccharides, in particular inulins modified by hydrophobic chains such as alkylcarbamate groups, in particular alkyl C8-C18 carbamate, and more particularly laurylcarbamate.

[0194] As an example of these compounds, we can notably cite the product sold under the name INUTEC SL1 by the company CREACHEM.

[0195] The compositions according to the invention find their application in a large number of treatments, in particular cosmetic, of the skin, lips and hair, including the scalp, in particular for the protection and / or care of the skin, lips and / or hair, and / or for the makeup of the skin and / or lips.

[0196] Another object of the present invention is the use of the compositions according to the invention as defined above for the manufacture of products for the cosmetic treatment of the skin, lips, nails, hair, eyelashes, eyebrows and / or scalp, in particular skincare products, sun protection products and makeup products. EXAMPLES

[0197] The present invention will now be described more specifically by means of examples, which are in no way limiting of the scope of the invention. However, the examples allow for the support of specific features, variants, and preferred embodiments of the invention.

[0198] A- Example of synthesis of thiopyridinone compounds of formula (I) or (I')

[0199] Step 1: Synthesis of compound 3 - N-[(2-thioxo-l,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate

[0200] Route 1: via 2-mercaptonicotinic acid

[0201] Thionicotinic acid is introduced into a flask in acetonitrile followed by carbonyldiimidazole (CDI). The resulting mixture is heated under reflux for one hour and then left at room temperature. After returning to room temperature, ethyl glycinate hydrochloride is added, and the resulting mixture is reheated at 60°C for 3 hours. The mixture is then left at room temperature overnight. After the night, the reaction mixture is evaporated. The residue is resuspended in dichloromethane and washed twice with 2 N HCl. The organic phase is dried over anhydrous sodium sulfate then evaporated and purified over silica Dichloromethane 97 / methanol 3. The fractions are evaporated. A light yellow powder is obtained.

[0202] Route 2: via 2-chlorotonic acid

[0203] In a three-necked bottle, 2-chloronicotinic acid (250.0 g, 1.587 mol) is introduced into ethyl acetate (500 ml) and then SOC12 (210.0 g, 1.761 mol) is added dropwise into the mixture. The mixture is heated under reflux until complete conversion. Once the reaction is finished, the mixture is cooled to room temperature and diluted with ethyl acetate (375 ml). A solution of ethyl glycinate hydrochloride (265.8 g, 1.904 mol) diluted in water (400 ml) and triethylamine (393.5 g, 3.88 mol) is then added to the mixture. The mixture is stirred for 3 to 4 hours, and then the ethyl acetate is removed under vacuum. The aqueous solution thus obtained is then diluted with water (1250 ml) and then acidified with 3N HCl (25 ml). Sodium thiosulfate (1379g, 5.555mol) is then added and the mixture is heated under reflux for 6 hours. After cooling to 10°C, the yellow solid is filtered and washed with water (3 times 750ml). The raw product is then treated with carbon black in a 75 / 25 ethanol / water mixture. The carbon black is then hot-filtered and the ethanol is evaporated. The mixture is cooled to room temperature, then the product is filtered and vacuum-dried. A light yellow powder is thus obtained. The 1H NMR and mass spectra are consistent with the structure. Melting point: 151 °C (capillary tube).

[0204] Step 2: Synthesis of the compound N-[(2-thioxo-l,2-dihydropyridin-3-yl)carbonyl]glycine from the compound obtained in step 1

[0205] In a three-necked bottle, ethyl N-[(2-thioxo-l,2-dihydropyridin-3-yl)carbonyl]glycine nate (48 g, 0.317 mol) and a 95% EtOH solution (48 mL) are introduced. The resulting mixture is cooled to 10°C. A solution of NaOH (16 g) in 144 mL of water is added dropwise into the mixture. The organic solvent is evaporated and then the pH of the mixture is adjusted to a value of 3-4. The mixture is then cooled to a temperature between 0 and 10 °C and then filtered. The resulting product is washed with water and dried under vacuum. A light yellow powder is obtained. The 1H NMR and mass spectra are consistent with the structure. Melting point: 241.0-241.8 °C (capillary tube)

[0206] Example 2: Synthesis of compounds 1-1 and 1-2 Composed 1-1

[0207] In a 250 mL flask are introduced the (2-mercaptonicotinoyl)glycine obtained in example 1 (20.000 g, 1 Eq, 94.242 mmol) and DMF (100 mL). The mixture is stirred until a clear solution is obtained, then carbonyldiimidazole (16.809 g, 1.1 Eq, 103.67 mmol) is added per portion. The resulting suspension is stirred at a temperature of 20°C until no bubbling occurs (typically for one hour). Ethyl glycinate hydrochloride (14.470 g, 1.1 Eq, 103.67 mmol) is then added, and the mixture is stirred for one hour at a temperature of 20 °C. The reaction mixture is then slowly added to a 10% aqueous NaHCO3 solution while stirring. The resulting suspension is filtered through a sintered glass slurry to obtain a solid, which is then rinsed with distilled water. The solid is dried at 50 °C under vacuum to obtain ethyl (2-mercaptonicotinoyl)glycylglycinate (compound 1-1) in the form of a yellow powder.

[0208] Spectroscopic analyses conform to the indicated structure. Compound 1-2

[0209] In a 250 mL flask, the compound 1-1, as previously obtained, (ethyl (2-mercaptonicotinoyl)glycylglycinate) (13.440 g, 1 Eq, 45.202 mmol) and distilled water (70 mL) are introduced. With stirring, a 50% sodium hydroxide solution is added until a pH value of around 12-13 is reached, maintaining the temperature below 25°C. The resulting mixture is stirred for one hour at a temperature of 25°C, then the pH is adjusted to a value of 2 with 37% hydrochloric acid. The resulting suspension is filtered through a sintered glass sinter and then the resulting solid is rinsed with distilled water. The solid is dried at 50 °C under vacuum to obtain the compound 1-2 (2-mercaptonicotinoyl)glycylglycine in the form of a yellow powder).

[0210] B- Examples of preparation of lipophilic acrylic polymers according to the invention

[0211] Determination of molecular weight by gel permeation chromatography (GPC):

[0212] The sample is prepared by dissolving the polymer at 10 mg / ml in tetrahydrofuran. The sample is placed in an oven at 54 °C for 10 minutes and then in an oscillating shaker for 60 minutes to aid dissolution. Upon visual inspection, the sample appears to be completely dissolved in the solvent.

[0213] The prepared sample was analyzed using two 300 x polypore columns 7.5 mm (manufactured by Agilent Technologies), a Waters 2695 chromatographic system, a tetrahydrofuran mobile phase, and refractive index detection. The sample was filtered through a 0.45 µm nylon filter before being injected into the liquid chromatograph. The standards used for calibration were the Easi Vial narrow polystyrene (PS) standards from Agilent Technologies.

[0214] Polystyrene standards ranging from 2,520,000 to 162 Daltons were used for calibration.

[0215] The system is equipped with a PSS SECcurity 1260 RL detector. The polystyrene calibration curve was used to determine the average molecular weight. The recording of the diagrams and the determination of the different molecular weights was done using the Win GPC Unichrom 81 program.

[0216] Determination of the melting point by differential scanning calorimetry (or DSC):

[0217] This method describes the general procedure for determining the melting point of polymers by differential scanning calorimetry. This method is based on ASTM E791 and ASTM D 34182, and the DSC calibration is performed according to ASTM E 9672. Example of polymer preparation 1:

[0218] Behenyl acrylate / 2-hydroxyethyl acrylate copolymer (Polymer 1):

[0219] In a 4-necked flask equipped with a side-blade stirrer, an internal thermometer, two funnels, a reflux condenser, and an extension for two additional necks, 175 g of behenyl acrylate, 25 g of 2-hydroxyethyl acrylate, and 0.4 g of 2,2'-azobis(2-methylbutyronitrile) (Akzo Nobel) were added for 60 minutes at 80 °C to 40 g of isopropanol with stirring after removing oxygen from the system by means of a nitrogen purge for 20 minutes. The mixture was stirred at 80 °C for 3 hours. Then the solvent was removed by vacuum distillation, and 1 g of dilauryl peroxide was added, and the reaction was The process continued for 60 minutes at 110 °C. The step was repeated. The mixture was then cooled to 90 °C, a jet of demineralized water was added, and the mixture was stirred. The water was removed by vacuum distillation.

[0220] Molecular weight: Mn = 7300 g / mol, Mw = 21000 , Mw / Mn = 2.8;

[0221] Melting point: 65 °C. Example of polymer preparation 2:

[0222] Stearyl acrylate / 2-hydroxyethyl acrylate copolymer (Polymer 2):

[0223] In a 4-necked bottle equipped with a side-blade stirrer, a thermometer Internally, two funnels, a reflux condenser, and an extension for two additional necks, 155 g behenyl acrylate, 45 g 2-hydroxyethyl acrylate, and 0.4 g 2,2'-azobis(2-methylbutyronitrile) (Akzo Nobel) were added to 50 g isopropanol for 90 minutes at 80 °C under stirring after removing oxygen from the system using nitrogen purging for 20 minutes. The mixture was stirred at 80 °C for 3 hours. The solvent was then removed by vacuum distillation, and 1 g dilauryl peroxide was added, and the reaction was continued for 60 minutes at 125 °C. This step was repeated. The mixture was then cooled to 90 °C, and a stream of demineralized water was added and stirred. The water was removed by distillation under empty.

[0224] Molecular weight: Mn = 7500 g / mol, Mw = 19000 , Mw / Mn = 2.6;

[0225] Melting point: 49 °C. C- Examples of formulations

[0226] The following examples serve to illustrate the invention without being limiting. In these examples, the quantities of ingredients present in the compositions are given as a percentage by weight of raw materials relative to the total weight of the composition. Manufacturing process

[0227] The compositions described below were prepared according to the following protocol. Preparation of aqueous phase A: Water was heated to 70 °C under constant stirring. The hydrophilic polymers were then added gradually, followed by a 10-minute turbine stirring period to ensure their proper dispersion and deployment. Sodium Stearoyl Glutamate was then added to the aqueous phase, and turbine stirring was maintained until complete melting. The thiopyridinone compound (2-Mercaptonicotinoyl Glycine) was then incorporated, and the resulting solution was again kept under turbine stirring for 10 minutes. Preparation of the oil phase B: Diisopropyl sebacate was heated separately to 72 °C, as was the lipophilic polymer if present. Agitation was then maintained until complete dissolution. Emulsion preparation: The two phases obtained previously (aqueous phase A and oily phase B) were then emulsified for 15 minutes at 70°C using a Rayneri emulsion press, a tool designed to produce a fine and homogeneous emulsion. The emulsion was then slowly cooled to room temperature with gentle stirring. Composition stability protocol

[0228] A series of tests was carried out on all the compositions thus obtained in order to characterize their physico-chemical properties and their stability over time. Sensory analysis: The visual appearance (smooth texture, homogeneity, color) and the odor were evaluated after a time T at different temperatures, in particular at T = 24 hours at room temperature, T = 1 week at 55 °C, T = 2 months at room temperature, and T = 2 months at 45 °C. Physico-chemical measurements: The pH and viscosity of the compositions were measured at different times T, including T = 24 hours and T = 2 months, at room temperature and at 45°C. Stability assessment: Various tests were put in place to assess the stability of the compositions. - Microscopic observations: Allowing observation of the emulsion structure, droplet size and the possible presence of aggregates after 24 hours, 1 week and 2 months. - Centrifugation test: The compositions were centrifuged for 1 hour to accelerate phase separation and detect any instability. - Lumisizer: This device allows for the prediction of the long-term stability of compositions. Samples were prepared and placed in the device and subjected to a rotation protocol for 2 hours at varying temperatures from 4°C to 60°C. This allows for the prediction of centrifugation stability at T = 24 hours at room temperature and at T = 2 months at 45°C. This device provides valuable information on long-term stability. Comparative examples 1 to 3

[0229] The following compositions were prepared. Phase Composition 1 (comparative) Composition 2 (invention) Composition 3 (comparative) 2-MERCAPTONICOTINOYL GLYCINE (compound 1-2) A 4 4 4 POLYACRYL OYLDIMETHYL TAURATE (HOSTACERIN AMPS from CL ARIANT) A - - 0.5 SODIUM STEAROYL GLUT AMATE A 0.5 0.5 0.5 WATER A 70 70 70 DIISOPROPYL SEBACATE B 25 25 25 Results

[0230] Microscopic observation after T = 24 hours at room temperature reveals that composition 2 according to the invention is in the form of a finer and more homogeneous emulsion than comparative compositions 1 and 3. Birefringent crystals of thiopyridinone compound, a sign of incomplete solubilization of the active ingredient due to saturation of the composition, are observed in the three compositions 1 to 3. However, their distribution is more homogeneous in composition 2 according to the invention, suggesting better dispersion of the thiopyridinone compound in the presence of scleroglucan. At all temperatures from T = 24 hours, and even more so at 1 week at 55 °C and 2 months at 45 °C, microscopic observation reveals that comparative compositions 1 and 3, which do not contain scleroglucan, exhibit significant destabilization. The emulsions are coarser and more inhomogeneous. Composition 1 shows droplets larger than 100 µm, and comparative composition 3, which contains the polymer AMPS (AMMONIUM POLYACRYLOYLDIMETHYL TAURATE), is particularly destabilized, with two immiscible phases forming large domains. In contrast, composition 2 according to the invention, which contains scleroglucan, has the same appearance as after 24 hours at room temperature. Thus, the results obtained highlight a positive impact of scleroglucan compared to xanthan gum and AMPS polymer on the stability of a composition including a thiopyridinone compound. Furthermore, composition 2 according to the invention comprising scleroglucan exhibits a much more stable viscosity than comparative compositions 1 and 3 comprising respectively xanthan gum and the AMPS polymer, for which an increase in viscosity of a factor of 2 is observed after 2 months at 45 °C. Examples 4 and 5

[0231] The following compositions were prepared. Phase Composition 4 (invention) Composition 5 (comparative) 2-MERCAPTONICOTINOYL GLYCINE (compound 1-2) A 4 4 SCLEROTIUM GUM (AMIGUM from ALBAN MULLER) A 0.5 - AMMONIUM POLYACRYLOYLDIMET HYL TAURATE (HOSTACERIN AMPS from CLARIANT) A - 0.5 SODIUM STEAROYL GLUTAMATE A 0.5 0.5 WATER A 68.5 68.5 DIISOPROPYL SEBACATE B 25 25 C12-22 ALKYLACRYLATE / HYDROXY ETHYL ACRYLATE COPOLYMER (Polymer 1) B 1.5 1.5 Results

[0232] Microscopic observation after T = 24 hours at room temperature reveals that composition 4 according to the invention is in the form of a finer and more homogeneous emulsion than comparative composition 5, which shows droplets greater than 100 pm. Birefringent crystals of thiopyridinone compound, a sign of incomplete solubilization of the active ingredient due to saturation of the composition, are observed in both compositions 4 and 5. However, their distribution is more homogeneous in composition 4 according to the invention, suggesting better dispersion of the thiopyridinone compound in the presence of scleroglucan. After one week at 55°C and two months at 45°C, microscopic observation reveals that the comparative composition 5, which does not contain scleroglucan, exhibits significant destabilization. The emulsion is particularly destabilized, with two immiscible phases forming large domains. In contrast, composition 4 according to the invention, which contains scleroglucan, retains the same appearance as after 24 hours at room temperature. Thus, the results obtained highlight a positive impact of scleroglucan compared to the AMPS polymer on the stability of a composition including a thiopyridinone compound. Furthermore, composition 4 according to the invention comprising scleroglucan exhibits a much more stable viscosity than comparative composition 5 comprising the AMPS polymer, for which an increase in viscosity of 40% is observed after 2 months at room temperature. The pH of the invention with scleroglucan is also very stable at 45 °C for T = 2 months unlike that of the comparative composition 5 comprising the AMPS polymer which increased by 0.6 points.

Claims

1. Demands Composition, particularly cosmetic or dermatological, including: (a) at least one compound selected from compounds of formula (I), tautomers of formula (!'), their salts, their solvates, such as their hydrates, their optical isomers, their racemates, and mixtures thereof:

2. in which: - Ri denotes a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in the Ci-CiO configuration or a branched C3-CiO configuration optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, and ii) -S-R3, and - R2 denotes a radical chosen from a) a hydrogen atom, b) a linear saturated hydrocarbon group in the CrCi2 configuration or a branched C3-Ci2 configuration or a cyclic C3-C8 configuration optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) a C5-Ci2 aryl group, optionally substituted by one or more hydroxyl groups and / or by one or more CrC8 alkoxy radicals and c) an aryl group in C5-C12, optionally substituted by one or more hydroxyl groups and / or by one or more alkoxy radicals in CrC8 and - R3 designates a radical chosen from a) a hydrogen atom, and b) a linear saturated alkyl group in Ci-CiO or branched in C3-CiO; and (b) at least one scleroglucan gum. Composition according to claim 1 wherein Ri of formulas (I) and (!') represents a hydrogen atom; a linear alkyl group (Ci-CiO) or a branched alkyl group (C3-CiO), in particular a linear alkyl group (Ci-C6) or a branched alkyl group (C3-C6), such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, plus preferably ethyl, in particular said alkyl group of Rin is not substituted.

3. Composition according to any one of claims 1 and 2 wherein R2 of formulas (I) and (!') represents a hydrogen atom; a linear (Ci-Ci0) or branched (C3-Ci0) alkyl group, in particular a linear (Ci-C6) or branched (C3-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group of R2 not being substituted.

4. Composition according to any one of claims 1 to 3 wherein R3 of formulas (I) and (!') represents a hydrogen atom; a linear Ci-Cio or branched C3-CiO saturated alkyl group; in particular a linear (Ci-C6) alkyl group or a branched (C3-C6) alkyl group, preferably an (CrC4) alkyl group such as the methyl group.

5. Composition according to any one of claims 1 to 4 wherein R2 of formula (I) and (!') represents a linear alkyl group (in C1-C10) or a branched alkyl group (in C3-C10), in particular a linear alkyl group (in C1-C6) or a branched alkyl group (in 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 in claim 1, 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 the carboxy.

6. Composition according to any one of claims 1 to 5 wherein R2 of formulas (I) and (!') represents a cycloalkyl (C3-C8) group, preferably a cycloalkyl (C5-C7) group such as cyclohexyl; a C5-Ci2 aryl group optionally substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals, preferably a phenyl group, in particular unsubstituted.

7. Composition according to any one of claims 1 to 6 wherein R3 of formulas (I) and (!') represents a hydrogen atom; a linear saturated alkyl group in C1-C10 or branched in C3-C10; in in particular a linear alkyl group (in C1-C6) or a branched alkyl group (in C3-C6), preferably an alkyl group (in C1-C4) such as a methyl group.

8. Composition according to any one of claims 1 to 7 wherein: - Ri of formulas (I) and (!') represents a radical selected from a) a hydrogen atom, and b) a linear saturated CrC6 or C3-C6 branched alkyl group optionally substituted by one or more groups, which may be identical or different, selected from i) -O-R3, and ii) -S-R3, preferably optionally substituted by one or more i) groups;- R2 of formula (I) and (!') represents a radical chosen from a) a hydrogen atom, and b) a linear saturated hydrocarbon group in C1-C10 or branched in C3-C10 or cyclic in C3-C8 as in C5-C6, optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) a phenyl group optionally substituted by one or more hydroxyl groups 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 saturated alkyl group in C1-C6 or branched in C3-C6.;

9. Composition according to any one of claims 1 to 8 wherein: - Ri of formula (I) and (!') represents a radical selected from a) a hydrogen atom, and b) a linear saturated C1-C4 or branched C3-C4 alkyl group optionally substituted by one or more groups, which may be identical or different, selected from i) -OR3>plus preferably unsubstituted; - R2 of formula (I) and (!') represents a radical chosen from a) a hydrogen atom, and b) a linear saturated hydrocarbon group in C1-C10 or branched in C3-C10 or cyclic in C3-C8 as in C5-C6, optionally substituted by one or more groups, which may be identical or different, chosen from i) -O-R3, iii) -C(O)-O-R3, and iv) an aryl group in C5-C12, optionally substituted by one or

10. several hydroxyl groups and / or by one or more alkoxy radicals in the Ci-C4 group; and - R3 of formula (I) and (!') represents a radical chosen from a) a hydrogen atom; b) a linear saturated alkyl group in C1-C4 or branched in C3-C4 such as methyl or ethyl. Composition according to any one of claims 1 to 9 wherein the compound of formula (I) is selected from the compounds 1 to 24 below, their tautomers, their salts, their solvates, such as their hydrates, their optical isomers, their racemates, and mixtures thereof, preferably compounds 1, 2, 4, 6, 7, 9, 11, 12, 14, 15, 16, 17, 18, 19, 20 or 21, more preferably 1, 9, 16, 18, 19, 20 or 21, even more preferably 18, 19, 20 or 21, and even better 20: No. Structure Chemical Name 1 "'CK H N-ethyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 2 >-------- o N-methyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 3 N-octyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 4 !1 i " k J N-benzyl-2-thioxo-1,2-dihydropyridine-3-carboxamide 5 —, Y—( / ( >.......{ G= / N-phényl-2-thio xo-l,2-dihydrop yridine-3-carbox amide 6 G A A G ? .11 A J A A A AA AA H H N-cyclohexyl-2-t hioxo-l,2-dihydr opyridine-3-carb oxamide : A 7 P : N- [2- (4-méthoxy phényl)éthyl]-2-t hioxo-l,2-dihydr opyridine-3-carb oxamide 8 A^A. N-(2-méthylprop yl)-2-thioxo-l,2-dihydropyridine-3-carboxamide 9 / X jls AA z\. A-- <* xA-“' "N ”' A- vx N-pentyl-2-thiox o-l,2-dihydropy ridine-3-carboxa mide 10 •■ y y N-nonyl-2-thiox o-l,2-dihydropy ridine-3-carboxa mide 11 0 / A z\ H II 1 ^A Aj si N-(2-hydroxyéth yl)-2-thioxo-l,2-dihydropyridine-3-carboxamide 12 N,N-diethyl 2-mercaptonicotinamide 13 > $ h 'Y Ta A"' Xs Vh N-ethyl-N-(2-hydroxyethyl)-2-thioxo-l,2-dihydropyridine-3-carboxamide 14 N-(2,3-dihydroxypropyl)-2-thioxol,2-dihydropyridine-3-carboxamide 15 0 A ...... x _JT .Av AH N-(l,3-dihydroxypropan-2-yl)-2-thioxo-l,2-dihydropyridine-3-carboxamide 16 H / N-[(2-thioxo-l,2-dihydropyridin-3-yl)carbonyl]ethyl alaninate 17 Xx' ■ .. . N-[(2-thioxo-l,2 -dihydropyridin-3-yl)carbonyl]ethyl phenyl alaninate 18 N-methyl-N-[(2-thioxo-l,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate 19 Zy À>k. xx .Xx •vx !4 N-[(2-thioxo-l,2 -dihydropyridin-3-yl)carbonyl]gl ycinate ethyl 20 TO \ / / \ / \ y N-methyl-N-[(2-thioxo-l,2-dihyd ropyridin-3-yl)ca rbonyl]glycine 22 .]¾ ,^NX. opyl)-2-thioxo-l, 2-dihydropyridin e-3-carboxamide A •"■ yy vï'".^ 24 :: ; J j-': X's. .'•■'S-, N-butyl-2-thioxo -1,2-dihydropyridine-3-carboxam ide

11. Composition according to any one of claims 1 to 10 comprising at least one lipophilic polymer comprising monomeric units of formula (A) and (B): (B) OH | (A) *' y" ] | O^O' | | LJW | (B) OH | wherein: RIs, independently of each other, are selected from alkyl or alkenyl radicals; with at least 60% by weight of the RI groups being radicals selected from stearyl and behenyl radicals, the percentage by weight referring to the sum of all RI groups present in the polymer; the weight ratio of the sum of all hydroxyethyl acrylate units to the sum of all acrylate units bearing the RI group is from 1:30 to 1:1; and the sum of the total of units A and B is at least 95% by weight of the total weight of the polymer.

12. Composition according to claim 11 wherein in the lipophilic acrylic polymer RI consists of an alkyl radical, preferably a Ci6-C22 alkyl radical, and more preferably a behenyl or stearyl radical.

13. Composition according to any one of claims 11 and 12 wherein in the lipophilic acrylic polymer at least 70% by weight of the RI groups are behenyl or stearyl radicals, preferably at least 80% by weight, more preferably at least 90% by weight.

14. Composition according to any one of claims 11 to 13 wherein in the lipophilic acrylic polymer the weight ratio of the sum of all hydroxyethyl acrylate units to the sum of all acrylate units bearing the RI group ranges from 1:15 to 1:1, preferably from 1:10 to 1:

4.

15. Composition according to any one of claims 11 to 14 wherein the lipophilic acrylic polymer has a number-average molecular weight Mn ranging from 5,000 to 9,000 g / mol.

16. Composition according to any one of claims 11 to 15 wherein the lipophilic acrylic polymer has a melting temperature of 40 °C to 70 °C, and preferably of 45 °C to 67 °C.

17. Composition according to any one of claims 11 to 16 wherein in the lipophilic acrylic polymer at least 60% by weight of the RI groups are stearyl radicals, and said polymer has a melting point of 40 to 60 °C, and preferably of 45 to 55 °C.

18. Composition according to any one of claims 11 to 17 wherein in the lipophilic acrylic polymer at least 60% by weight of the RI groups are behenyl radicals, and said polymer has a melting point of 60 °C to 70 °C, and preferably of 63 °C to 67 °C.

19. Composition according to any one of claims 1 to 18 further comprising one or more UV filters.

20. Composition according to any one of claims 1 to 19 in the form of an emulsion, preferably in the form of an oil-in-water emulsion.