Process for treating keratin fibers using at least one thiopyridinone compound

Abstract

The present invention relates to a method for treating keratin fibers, particularly human keratin fibers such as hair, comprising contacting said keratin fibers with at least one compound of formula (I) or (I'), as described below, and their optical isomers, geometric isomers, as well as their acid or base salts, organic or mineral, and their solvates such as hydrates. The invention also relates to one or more compounds of formula (II) or (II'), as described below, and their optical isomers, geometric isomers, as well as their acid or base salts, organic or mineral, and their solvates such as hydrates.The invention also relates to a process for treating keratin fibers, in particular human keratin fibers, such as hair, comprising bringing into contact with said keratin fibers at least one compound of formula (III) or (III'), as described below, and their optical isomers, geometric isomers as well as their acid or base salts, organic or mineral, and their solvates such as hydrates.

Description

Title of the invention: Process for treating keratin fibers using at least one thiopyridinone compound

[0001] The present invention relates to a process for shaping keratin fibers, in particular human keratin fibers, such as hair, comprising at least bringing into contact with said keratin fibers 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, or at least one composition Cl comprising it or them.

[0002] The invention also relates to one or more compounds of formula (II) or (II'), as described below, and / or their optical isomers, geometric isomers as well as their acid or base salts, organic or mineral, and their solvates such as hydrates.

[0003] The invention also relates to a process for shaping keratin fibers, in particular human keratin fibers, such as hair, comprising at least bringing into contact with said keratin fibers at least one compound of formula (III) or (III'), 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, or at least one composition comprising it or them.

[0004] Hair styling products are hair compositions usually used to build, structure and give hold to the hairstyle. Such compositions generally comprise one or more film-forming polymers, or "fixing polymers", allowing the formation of a coating film on the fibers so as to ensure the maintenance of the hairstyle and / or the formation of micro-welds between the fibers, thus leading to the fixing of the hair.

[0005] Such compositions are most often presented in the form of lotions, gels, mousses, or sprays, and are commonly applied to wet hair, which is shaped before blow-drying or drying.

[0006] However, the shaping provided by such styling products has the disadvantage of fading more or less quickly over time and / or following one or more washes.

[0007] In other words, such styling products generally lead to a hold of the shaping of the fibers which is still too often unsatisfactory.

[0008] Such compositions may further lead to unsatisfactory hair shaping, particularly when applied to sensitized hair, in particular by one or more chemical treatments, for example at least one straightening, perming, coloring and / or bleaching process.

[0009] Thus there is a real need to implement a process for the cosmetic treatment of keratin fibers, in particular human keratin fibers, such as hair, which does not have the drawbacks mentioned above, that is to say capable of shaping the keratin fibers, including keratin fibers sensitized by at least one chemical treatment, for example at least one straightening, perming, coloring and / or bleaching process, and this in a lasting manner.

[0010] The present invention therefore relates in particular to a process for shaping keratin fibers, in particular human keratin fibers, such as hair, comprising at least the application to said keratin fibers of at least one compound of formula (I) and / or (I') below, and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, or of at least one composition Cl comprising: OO (i) (D

[0011] Formula (I) and (!') in which: - Ri denotes a radical chosen from the group consisting of: a. a hydrogen atom, b. a linear C1-C10 or branched C3-C10 saturated alkyl group optionally substituted by one or more groups, identical or different, chosen from the group consisting of i) -O-R3 and ii) -S-R3; - R2 denotes a radical, cyclic or acyclic, chosen from the group consisting of: a. a hydrogen atom, b. a linear C1-C12 or branched C3-C12 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; said hydrocarbon group being optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-, or, c. a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; - R3 denotes a radical chosen from a) a hydrogen atom, b) a linear C1-C10 or branched C3-C10 saturated alkyl group; - R4 denotes a radical chosen from the group consisting of a) a hydrogen atom, b) a saturated linear C1-C10 or branched C3-C10 alkyl group, c) an alkali metal, d) an alkaline earth metal, or e) an ammonium group; - X represents an oxygen atom, a sulfur atom, preferably an oxygen atom, - R' represents a hydrogen atom or a C1-C4 alkyl group, in particular C1, preferably represents a hydrogen atom;

[0012] it being understood that when R4 denotes e) an ammonium group, then the electroneutrality of the compounds of formula (I) or (!') is ensured by one or more cosmetically acceptable anions such as halides preferably chosen from chloride or bromide.

[0013] The method according to the invention thus makes it possible to achieve the objectives as described above, by implementing on said fibers, at least one thiopyridinone compound of formula (I), as defined above, and / or at least one tautomer of a thiopyridinone compound of formula (I) (i.e. a compound of formula (!') as defined above), and / or one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, or a composition Cl comprising said compound(s) of formula (I) or (!') as defined above.

[0014] In other words, the method for treating keratin fibers, according to the invention, uses on said fibers, at least one compound of formula (I), and / or at least one tautomer of a compound of formula (I), and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, or at least one composition Cl comprising a compound of formula (I), and / or at least one tautomer of a compound of formula (I), and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0015] The method according to the invention makes it possible to improve the shaping of keratin fibers without risking damaging them, that is to say while retaining their cos properties metrics, for example in terms of feel, suppleness, softness, detangling or shine.

[0016] The method according to the invention makes it possible to improve the retention of the shape conferred on the keratin fibers, in particular by giving them a lasting shape, capable of being advantageously resistant, in particular to one or more shampoos.

[0017] The method according to the invention also has the advantage of modifying the shape of keratin fibers, in particular human keratin fibers such as hair.

[0018] The method according to the invention also makes it possible to easily and effectively shape keratin fibers, including sensitized keratin fibers, i.e. keratin fibers treated with at least one chemical treatment, in particular at least one permanent deformation process, for example a straightening or a perm, or a coloring process and / or a bleaching process.

[0019] The present invention also relates to the use of at least one compound of formula (I) and / or (I'), as defined above, and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, or of at least one composition Cl comprising said compound(s) of formula (I) or (I'), for shaping keratin fibers, in particular human keratin fibers, such as hair.

[0020] The invention also relates to a compound of formula (II) or (II') of the following formula, as well as one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures: (ii) (ir)

[0021] Formulas (II) and (II') in which:

[0022] - A represents a divalent hydrocarbon chain, saturated or unsaturated, of preferably saturated, cyclic or acyclic, preferably acyclic, linear or branched, comprising from 1 to 10 carbon atoms, interrupted by one or more (thio)amide(s) -C(X)-N(R')- or (NR')-C(X)- groups, and optionally substituted, in particular by one or more identical or different groups chosen from the group constituted by i) -O-R3 and ii) -S-R3;

[0023] - M denotes a radical chosen from the group consisting of a) a hydrogen atom, b) a linear C1-C10 or branched C3-C10 alkyl group, c) an alkali metal, d) an alkaline earth metal, or e) an ammonium group; preferably M represents a) a hydrogen atom or d) an alkali metal;

[0024] - Ri has the same meaning as in formula (I) or (!'); preferably, Ri re has a hydrogen atom;

[0025] - R3 has the same meaning as in formula (I) or (!'); preferably, R3 re has a hydrogen atom;

[0026] - X has the same meaning as in formula (I) or (!'); preferably X re has an oxygen atom;

[0027] - R' has the same meaning as in formula (I) or (!'); preferably, R' re has a hydrogen atom.

[0028] The compound(s) of formula (II) or (II') is or are thiopyridinone compounds having the advantage of cosmetically treating keratin fibers, including sensitized keratin fibers, in particular of shaping them.

[0029] The compound(s) of formula (II) or (II') is or are thiopyridinone compounds leading to better shape retention of keratin fibers, including sensitized keratin fibers.

[0030] The compound(s) of formula (II) or (II') in particular confer(s) lasting shaping to keratin fibers, in particular human keratin fibers such as hair.

[0031] Furthermore, the present invention also relates to a composition C2 comprising one or more compounds of formula (II) or (II'), as defined above, and optionally at least one cosmetic additive.

[0032] The invention also relates to the use of one or more compounds of formula (II) or (II'), as described above, or of at least one composition C1 or C2 comprising it or them, for the treatment of keratin materials, in particular keratin fibers, in particular for shaping keratin fibers, preferably human keratin fibers such as hair.

[0033] The invention further relates to a process for shaping keratin fibers, in particular human keratin fibers, such as hair, comprising at least the application to said keratin fibers of at least one compound of the following formula (III) and / or (III'), and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, or of at least one composition C1 or C3 containing it or them: O H O I H

[0034]

[0035]

[0036] (HD (III') in which:

[0037]

[0038]

[0039]

[0040]

[0041] (III) Formula (III) Ri has the same meaning as in formulae (I) and (I'), R2 denotes a radical chosen from the group consisting of a. a hydrogen atom, b. a linear C1-C12 or branched C3-C12 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; c. a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; - R3 denotes a radical chosen from a) a hydrogen atom, b) a linear C1-C10 or branched C3-C10 saturated alkyl group; - R4 denotes a radical chosen from the group consisting of a) a hydrogen atom, b) a linear C1-C10 or branched C3-C saturated alkyl group 10- The compound(s) of formula (II) or (II') is or are thiopyridinone compounds leading to better shape retention of keratin fibers, including keratin fibers sensitized by at least one chemical treatment as described above. The compound(s) of formula (II) or (II') lead(s) in particular to a lasting shaping of keratin fibers, in particular human keratin fibers such as hair. Likewise, the invention relates to the use of one or more compounds of formula (III) or (III'), as described above, or of at least one composition C1 or C3 containing it or them, for shaping keratin fibers, in particular human keratin fibers such as hair. Other objects, characteristics, aspects and advantages of the invention will appear even more clearly on reading the description and the example which follows. In what follows, and unless otherwise indicated, the limits of a domain of values ​​are included in this domain, in particular in the expressions "included

[0042]

[0043]

[0044] between” and “ranging from ... to ...”. Furthermore, the expression "at least one" used in this description is equivalent to the expression "one or more". Furthermore, the expression "at least" used in the present description is equivalent to the expression "greater than or equal to". Finally, in a manner known per se, the term "Cn" or "Cn" compound or group denotes a compound or group containing "n" carbon atoms in its chemical structure. Compound of formula (I) and (!') As indicated above, the thiopyridinone compound(s) is(are) chosen from the group consisting of the compounds of formula (I) or (!) below, as well as one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures:

[0045] (i) (D Formula (I) and (!') in which: - Ri denotes a radical chosen from the group consisting of: a. a hydrogen atom, b. a linear C1-C10 or branched C3-C10 saturated alkyl group optionally substituted by one or more groups, identical or different, chosen from the group consisting of i) -O-R3 and ii) -S-R3; - R2 denotes a radical, cyclic or acyclic, chosen from the group consisting of: a. a hydrogen atom, b. a linear C1-C12 or branched C3-C12 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; said hydrocarbon group being optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-, or, c. a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; - R3 denotes a radical chosen from a) a hydrogen atom, b) a linear C1-C10 or branched C3-C10 saturated alkyl group; - R4 denotes a radical chosen from the group consisting of a) a hydrogen atom, b) a saturated linear C1-C10 or branched C3-C10 alkyl group, c) an alkali metal, d) an alkaline earth metal, or e) an ammonium group; - X represents an oxygen atom, a sulfur atom, preferably an oxygen atom, - R' represents a hydrogen atom or a C1-C4 alkyl group, in particular C1, preferably R' represents a hydrogen atom;

[0046] it being understood that when R4 denotes e) an ammonium group, then the electroneutrality of the compounds of formula (I) or (!') is ensured by one or more cosmetically acceptable anions such as halides, preferably chosen from chloride or bromide.

[0047] As previously indicated, the compound of formula (!') is a tautomer of the compound of formula (I).

[0048] In other words, the thiopyridinone compound(s) is(are) chosen from the group consisting of the compounds of formula (I), as described above, the tautomers of formula (!'), as described above, as well as one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0049] According to one embodiment of the invention, Ri represents a) a hydrogen atom.

[0050] According to another embodiment of the invention, Ri represents b) an alkyl group saturated linear C1-C10 or branched C3-C10 optionally substituted by one or more groups, identical or different, chosen from the group consisting of i) -OR 3 and ii) -S-R3.

[0051] According to this embodiment, Ri represents b) a linear C1-C10 or branched C3-C10 saturated alkyl group, preferably a linear C1-C6 alkyl group, such as methyl, ethyl, n-pentyl, n-hexyl, or a branched C3-C6 alkyl group, such as isopropyl, isobutyl, tert-butyl, more preferably Ri represents an ethyl group.

[0052] Preferably, in formulas (I) and (!), Ri represents a) a hydrogen atom or a linear C1-C6 or branched C3-C6 saturated alkyl group.

[0053] More preferably, in formulas (I) and (!), Ri represents a) a hydrogen atom or a saturated C1-C4, in particular C1-C2, alkyl group.

[0054] More preferably, in formulas (I) and (!), Ri represents a) an atom of hydrogen.

[0055] According to one embodiment, R3 represents a) a hydrogen atom.

[0056] According to another embodiment, R3 represents b) a linear saturated alkyl group in C1-C10, in particular in C1-C6, more particularly in C1-C4, or a saturated alkyl group branched in C3-C10, in particular in C3-C6, more particularly in C3-C4, preferably an alkyl group, preferably linear, in C1-C4, more preferably in C1.

[0057] Preferably, in formulas (I) and (!), R3 represents a) a hydrogen atom or b) a linear C1-C6 or branched C3-C6 saturated alkyl group.

[0058] More preferably, in formulas (I) and (!), R3 represents a) a hydrogen atom.

[0059] Preferably, in formulas (I) and (!), Ri represents a hydrogen atom and R3 represents a) a hydrogen atom or a linear saturated C1-C6 or branched C3-C6 alkyl group, more preferably Ri and Represent a hydrogen atom.

[0060] According to one embodiment of the invention, R4 represents a) a hydrogen atom.

[0061] According to another embodiment of the invention, R4 represents b) an alkyl group saturated linear C1-C10, in particular C1-C6, more particularly C1-C4, such as methyl or ethyl, or a saturated branched C3-C10, in particular C3-C6, more particularly C3-C4 alkyl group.

[0062] According to another embodiment of the invention, R4 represents c) an alkali metal or d) an alkaline earth metal, preferably c) an alkali metal such as sodium or potassium.

[0063] According to another embodiment of the invention, R4 represents e) an ammonium group.

[0064] According to one embodiment, R4 represents a) a hydrogen atom or c) an alkali metal.

[0065] According to another embodiment, R4 represents c) an alkali metal, d) an alkaline earth metal or e) an ammonium group, preferably R4 represents c) an alkali metal such as sodium or potassium.

[0066] Preferably, R4 represents a) a hydrogen atom, b) a linear C1-C6, in particular C1-C4, alkyl group, or c) an alkali metal.

[0067] According to an advantageous embodiment, in formulas (I) and (!'): - Ri represents a) a hydrogen atom, - R3 represents a) a hydrogen atom or b) a linear saturated alkyl group in C1-C6 or branched in C3-C6, preferably R3 represents a hydrogen atom, - R4 represents a) a hydrogen atom, b) a linear C1-C6, in particular C1-C4, alkyl group, or c) an alkali metal such as sodium or potassium, preferably a hydrogen atom or a linear C1-C6, in particular C1-C4, alkyl group.

[0068] Preferably, in formulas (I) and (!), R1 and R3 represent a hydrogen atom, and R4 represents a) a hydrogen atom, b) a linear C1-C6, in particular C1-C4, alkyl group, or c) an alkali metal such as sodium or potassium.

[0069] According to one embodiment, R2 denotes a) a hydrogen atom.

[0070] According to another embodiment, R2 denotes c) a C5-C12 aryl group even partially substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals.

[0071] According to another embodiment, R2 denotes b) a linear C1-C12 or branched C3-C12 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; said hydrocarbon group being optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their combinations such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

[0072] According to another embodiment, R2 denotes b) a C3-C8 cyclic hydrocarbon group, optionally substituted, preferably substituted, by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -O(O)-O-1^, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more Cr-C8 alkoxy radicals; said hydrocarbon group being optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their combinations such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

[0073] According to another embodiment, R2 denotes b) a C3-C8 cyclic hydrocarbon group, optionally substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more Cr-C8 alkoxy radicals; said hydrocarbon group being interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their combinations such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

[0074] According to another embodiment, R2 denotes b) a C3-C8 cyclic hydrocarbon group, substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C alkoxy radicals 1-C8.

[0075] According to another embodiment, R2 denotes b) a C3-C8 cyclic hydrocarbon group, substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; said hydrocarbon group being interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their combinations such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

[0076] According to another embodiment, R2 denotes b) a C3-C8 cyclic hydrocarbon group, interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their associations such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

[0077] According to another embodiment, R2 denotes b) a C3-C8 cyclic hydrocarbon group.

[0078] According to another embodiment, R2 denotes b) a linear C1-C12 or branched C3-C12 saturated hydrocarbon group, optionally substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; said hydrocarbon group being optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their combinations such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

[0079] Advantageously, in formulas (I) and (!'): - Ri represents a) a hydrogen atom, - R3 represents a) a hydrogen atom or b) a linear saturated alkyl group in C1-C6 or branched in C3-C6, preferably R3 represents a hydrogen atom, - R4 represents a) a hydrogen atom, b) a linear C1-C6, in particular C1-C4, alkyl group, or c) an alkali metal such as sodium or potassium, preferably a hydrogen atom or a linear C1-C6, in particular C1-C4, alkyl group, - R2 denotes b) a linear C1-C12 or branched C3-C12 saturated hydrocarbon group, optionally substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; said hydrocarbon group being optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their combinations such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-; with X and R' as defined above.

[0080] According to another embodiment, R2 denotes b) a linear C1-C12 or branched C3-C12 saturated hydrocarbon group, substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; said hydrocarbon group being optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their combinations such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

[0081] According to another embodiment, R2 denotes b) a linear C1-C12 or branched C3-C12 saturated hydrocarbon group, optionally substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; said hydrocarbon group being interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their combinations such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

[0082] According to another embodiment, R2 denotes b) a linear C1-C12 or branched C3-C12 saturated hydrocarbon group, optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their associations such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

[0083] Preferably, in formula (I) or (!), R2 denotes b) a linear C1-C12 or branched C3-C12, or cyclic C3-C8 saturated hydrocarbon group.

[0084] According to another embodiment, R2 denotes b) a linear C1-C12 or branched C3-C12 saturated hydrocarbon group, optionally substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals.

[0085] According to another embodiment, R2 denotes b) a linear C1-C12 or branched C3-C12 or cyclic C3-C8 saturated hydrocarbon group, preferably a linear C1-C12 or branched C3-C12 saturated hydrocarbon group, said hydrocarbon group being optionally substituted by one or more groups, identical or different, chosen from iii) -C(O)-O-R4, preferably said group being substituted by one or more groups iii) -C(O)-O-R4; said hydrocarbon group being optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their combinations such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

[0086] According to another embodiment, R2 denotes b) a linear C1-C12 or branched C3-C12 saturated hydrocarbon group, substituted by one or more groups iii) -C(O)-O-R4; said hydrocarbon group being further optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their associations such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

[0087] Advantageously, in formulas (I) and (!'): - Ri represents a) a hydrogen atom, - R3 represents a) a hydrogen atom or b) a linear saturated alkyl group in C1-C6 or branched in C3-C6, preferably R3 represents a hydrogen atom, - R4 represents a) a hydrogen atom, b) a linear C1-C6, in particular C1-C4, alkyl group, or c) an alkali metal such as sodium or potassium, preferably a hydrogen atom or a linear C1-C6, in particular C1-C4, alkyl group, - R2 denotes b) a linear C1-C12 or branched C3-C12 saturated hydrocarbon group, substituted by one or more groups iii) -C(O)-O-R4; said hydrocarbon group being further optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their combinations such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-; with X and R' as defined above.

[0088] According to another embodiment, R2 denotes b) a linear C1-C12 or branched C3-C12 saturated hydrocarbon group, substituted by one or more groups iii) -C(O)-O-R4; said hydrocarbon group being further optionally substituted by one or more groups, identical or different, chosen from the group consisting of i) -O-R3, ii) -S-R3, and iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; said hydrocarbon group being further optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

[0089] Preferably, in formulas (I) and (!'): - Ri is as defined previously, preferably Ri represents a hydrogen atom; - R2 denotes b) a linear C1-C12 or branched C1-C12 saturated hydrocarbon group C3-C12 or C3-C8 cyclic, optionally substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4; said hydrocarbon group being optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-; - R', R3, R4 and X having the same meanings as those described above cededly.

[0090] More preferably, in formulas (I) and (!'): - Ri is as defined previously, preferably Ri represents a hydrogen atom; - R2 denotes b) a linear C1-C12 or branched C3-C[2 or cyclic C3-C8 saturated hydrocarbon group, substituted by one or more groups, identical or different, iii) -C(O)-O-R4; said hydrocarbon group being further optionally substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3; said hydrocarbon group being optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-; - R', R3, R4 and X having the same meanings as those described above cededly. Compounds of formula (II) and (II')

[0091] Preferably, the thiopyridinone compound(s) of formula (I) and (!') is or are chosen from the group consisting of the compounds of formula (II) or (II'), as well as one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures: (ii) (ir)

[0092] Formulas (II) and (II') in which:

[0093] - A represents a divalent hydrocarbon chain, saturated or unsaturated, of preferably saturated, cyclic or acyclic, preferably acyclic, linear or branched, comprising from 1 to 10 carbon atoms, interrupted by one or more (thio)amide(s) -C(X)-N(R')- or (NR')-C(X)- groups, and optionally substituted, in particular by one or more identical or different groups chosen from the group consisting of i) -O-R3 and ii) -S-R3;

[0094] - M denotes a radical chosen from the group consisting of a) a hydrogen atom, b) a linear C1-C10 or branched C3-C10 alkyl group, c) an alkali metal, d) an alkaline earth metal, or e) an ammonium group; preferably M represents a) a hydrogen atom or d) an alkali metal;

[0095] - Ri has the same meaning as in formula (I) or (!'); preferably, Ri re has a hydrogen atom;

[0096] - R3 has the same meaning as in formula (I) or (!'); preferably, R3 re has a hydrogen atom;

[0097] - X has the same meaning as in formula (I) or (!'); preferably X re has an oxygen atom;

[0098] - R' has the same meaning as in formula (I) or (!'); preferably, R' re has a hydrogen atom.

[0099] In other words, the thiopyridinone compound(s) of formula (I) and (!') is or are chosen from the group consisting of the compounds of formula (II), the tautomers of formula (II'), as well as one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0100] According to one embodiment, in formulas (II) and (II'), Ri represents a hydrogen atom.

[0101] According to one embodiment, in formulas (II) and (II'), M represents c) an alkali metal or d) an alkaline earth metal, preferably M represents c) an alkali metal such as sodium or potassium.

[0102] According to another embodiment, in formulas (II) and (II'), M represents an ammonium group.

[0103] According to another embodiment, in formulas (II) and (II'), M represents a linear C1-C10 or branched C3-C10 alkyl group.

[0104] According to this embodiment, in formulas (II) and (II'), M represents a linear saturated C1-C10, in particular C1-C6, more particularly C1-C4 alkyl group, such as methyl or ethyl, or a branched saturated C3-C10, in particular C3-C6, more particularly C3-C4 alkyl group.

[0105] According to this embodiment, in formulas (II) and (II'), M represents a saturated, preferably linear, C1-C4 alkyl group, in particular methyl.

[0106] Preferably, in formulas (II) and (II'), M represents a hydrogen atom or an alkali metal.

[0107] Alternatively, preferably, in formulas (II) and (II'), M represents c) an alkali metal, d) an alkaline earth metal or e) an ammonium, preferably M represents an alkali metal such as sodium or potassium.

[0108] Preferably, M represents a hydrogen atom, a saturated C1-C4 alkyl group, such as methyl or ethyl, or an alkali metal.

[0109] Preferably, in formulas (II) and (II'), A represents a divalent hydrocarbon chain, saturated or unsaturated, preferably saturated, comprising from 1 to 8 carbon atoms, particularly A represents a (C2-C6)alkylene group, linear or branched, preferably linear; said chain A being interrupted by a group -C(X)-N(R')- with X and R' as defined previously, more particularly -C(O)-N(H)-.

[0110] Preferably, in formulas (II) and (II'), A represents a group CH2 -C(O)-N(R')-CH2- or -CH2-N(R')-C(X)-CH2- with X and R' as defined previously, preferably -CH2-C(O)-N(H)-CH2-.

[0111] Preferably, the compound(s) of formula (II) and (II'), their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, are such that: - Ri has the same meaning as in formula (I) or (I'); preferably, Ri represents a hydrogen atom, - A represents a (C2-C6)alkylene group, linear or branched, preferably linear; said chain A being interrupted by a group -C(X)-N(R')- with X and R' as defined previously and preferably representing -C(O)-N(H)-;

[0112] - M denotes a radical chosen from the group consisting of a) a hydrogen atom, b) a linear C1-C10 or branched C3-C10 alkyl group, in particular a C1-C4 alkyl group, c) an alkali metal, d) an alkaline earth metal, or e) an ammonium group; preferably M represents a) a hydrogen atom, b) a C1-C4 alkyl group, d) an alkali metal;

[0113] - R3 has the same meaning as in formula (I) or (I'); preferably, R3 re has a hydrogen atom;

[0114] - X has the same meaning as in formula (I) or (I'); preferably X re has an oxygen atom;

[0115] - R' has the same meaning as in formula (I) or (I'); preferably, R' re has a hydrogen atom.

[0116] Preferably, the compound(s) of formula (II) and (II'), their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, are such that: - Ri represents a hydrogen atom, - R' represents a hydrogen atom or a C1-C4 alkyl group, in particular particular in Ci, preferably R' represents a hydrogen atom; - A represents a divalent hydrocarbon chain, saturated or unsaturated, preferably saturated, comprising from 1 to 8 carbon atoms, particularly A represents a (C2-C6)alkylene group, linear or branched, preferably linear; said chain A being interrupted by a group -C(X)-N(R')- with X and R' as defined previously, preferably -C(O)-N(H)-; more particularly A represents a group CH2-C(O)-N(R')-CH2- or -CH2 -N(R')-C(X)-CH2- with X and R' as defined previously, preferably -CH2-C(O)-N(H)-CH2-; - M being as defined above, preferably represents a hydrogen atom, an alkali metal, or an alkyl group, linear or branched in C1-C4, such as methyl or ethyl, more preferably represents a hydrogen atom or an alkali metal such as sodium or potassium.

[0117] More preferably, the compound(s) of formula (I) or (!') or (II) or (II') is or are chosen from the group consisting of the compounds of formula (IIA) or (IIB) below and / or one of their acid or base salts, organic or mineral, their solvates, such as hydrates, their optical isomers, their geometric isomers and their mixtures:

[0118] Formulas (IIA) and (IIB) in which: - Ra and Rb independently denote a hydrogen atom or a C1-C4 alkyl radical optionally substituted by one or more hydroxyl (OH) or thiol (SH) radicals; and - n and m independently denote an integer equal to 1 or 2 or 3: - M has the same meaning as for compounds of formula (II) or (II'); particularly M represents a hydrogen atom, an alkali metal, or an alkyl group, linear or branched, CrC4 alkyl such as methyl or ethyl, preferably a hydrogen atom or an alkali metal such as sodium or potassium.

[0119] According to one embodiment, in formulas (IIA) and (IIB), the index n is equal to 1.

[0120] According to one embodiment, in formulas (IIA) and (IIB), the index m is equal to 1.

[0121] According to a particular embodiment, in formulas (IIA) and (IIB), n is equal to m.

[0122] According to one embodiment, in formulas (IIA) and (IIB), n and m are different.

[0123] According to one embodiment, in formulas (IIA) and (IIB), Ra denotes an atom of hydrogen.

[0124] According to one embodiment, in formulas (IIA) and (IIB), Rb denotes a hydrogen atom.

[0125] According to a particular embodiment, in formulas (IIA) and (IIB), Ra and Rb are identical.

[0126] According to one embodiment, in formulas (IIA) and (IIB), Ra and Rb are different.

[0127] According to one embodiment, in formulas (IIA) and (IIB), Ra denotes a CrC4 alkyl radical substituted by one or more hydroxyl (OH) or thiol (SH) radicals, preferably substituted by a radical chosen from OH or SH.

[0128] According to one embodiment, in formulas (IIA) and (IIB), Ra denotes a CrC4 alkyl radical substituted, more preferably by an OH radical.

[0129] According to one embodiment, Rb denotes a C1-C4 alkyl radical substituted by one or more hydroxyl (OH) or thiol (SH) radicals, preferably substituted by a radical chosen from OH or SH, more preferably by an OH radical.

[0130] According to one embodiment, in formulas (IIA) and (IIB), Rb denotes an unsubstituted Cr-C4 alkyl radical such as methyl.

[0131] Preferably, in formulas (IIA) and (IIB): - n and m are identical and are equal to 1, - Ra and Rb, identical or different, denote a hydrogen atom or a linear or branched CrC4 alkyl radical, optionally substituted by one or more hydroxyl (OH) or thiol (SH) radicals, preferably substituted by a radical chosen from OH or SH, more preferably substituted by an OH radical; - M represents a hydrogen atom, an alkali metal or a linear or branched CrC4 alkyl group, preferably methyl or ethyl.

[0132] According to a particularly preferred embodiment, the compounds of formula (I) or (I') or (II) or (II') or (IIA) or (IIB) are chosen from the compounds of formulas (IIa) to (IIi) or (II'a) to (II'i) below as well as their tautomers and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures:

[0133] with M as defined above, particularly M represents a hydrogen atom, an alkali metal, or a linear or branched C1-C4 alkyl group such as methyl or ethyl, more preferably a hydrogen atom or an alkali metal such as sodium or potassium.

[0134] According to a very particularly preferred embodiment, the compounds of formula (I) or (!') or (II) or (II') or (IIA) or (IIB) are chosen from the compounds of formulas (IIa) or (II'a) above and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures:

[0135] Even more preferably, the compounds of formula (I) or (I') or (II) or (II') or (IIA) or (IIB) are chosen from the compounds of formula (II), and more particularly among the compounds of formulae (II-1) or (II' 1) or (II-2) or (II'2), below and / or one of their acid or base salts, organic or mineral, in particular their sodium or potassium salts, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures: ai-1) O (IF1) (IF 2)

[0136] According to the present invention, the compounds of formula (II' 1) and (II' 2) correspond to the tautomers of the compounds of formula (II-1) and (II-2).

[0137] Advantageously, the compound according to the invention is the compound of formula (II-2) or (II-2). Compounds of formula (III) and (III')

[0138] Preferably, the thiopyridinone compound(s) of formula (I) and (I') is or are chosen from the group consisting of the compounds of formula (III) or (III'), as well as one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures: O O I H (HD (III)

[0139] Formulas (III) and (III') in which: - Ri is as defined previously for compounds of formula (I) or (I'), - R2 denotes a radical chosen from the group consisting of:

[0140] a) a hydrogen atom,

[0141] b) a linear C1-C12 or branched C3-C[2 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, identical or different, chosen from:

[0142] i) -O-R3,

[0143] ii) -S-R3,

[0144] iii) -C(0)-0-R4, and

[0145] iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals, and

[0146] c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals, and

[0147]

[0148] R3 denotes a radical chosen from the group consisting of: a) a hydrogen atom, and (b) a linear or branched C1-C10 saturated alkyl group; and R4 denotes a radical chosen from a) a hydrogen atom, b) a linear C1-C10 or branched C3-C10 saturated alkyl group.

[0149] According to one embodiment, in formulas (I) and (!') or (III) and (III'), Ri represents: a hydrogen atom, or a linear C1-C10 alkyl group or a branched C3-C10 alkyl group, especially a linear C1-C6 alkyl group or a branched C3-C6 alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl, in particular said alkyl group of R1 is unsubstituted.

[0150] Preferably, in formulas (I) and (I') or (III) and (III'), Ri represents a hydrogen atom.

[0151] According to one embodiment, in formulas (I) and (I') or (III) and (III'), R2 represents: a hydrogen atom; a C1-C10 linear alkyl group or a C3-C10 branched alkyl group, especially a C1-C6 linear alkyl group or a C3-C6 branched alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably, a methyl or ethyl group; said alkyl group of R2 being unsubstituted.

[0152] In formulas (I) and (I') or (III) and (III'), R2 may represent a linear C1-C10 alkyl group or a branched C3-C10 alkyl group, in particular a linear C1-C6 alkyl group or a branched C3-C6 alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group being substituted by one or more groups selected from i), ii), iii) and iv) as defined above, preferably said alkyl group being substituted by one or two groups selected from i), ii) and iii), more preferably by one or two groups selected from i) and iii), better substituted by a group iii) such as carboxy.

[0153] In formulas (I) and (!') or (III) and (III'), R2 can represent: a C3-C8 cycloalkyl group, preferably a C5-C7 cycloalkyl group such as cyclohexyl; a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals, preferably a phenyl group in particular unsubstituted.

[0154] According to one embodiment, in formulas (I) and (I') or (III) and (III'), R3 represents: a hydrogen atom, a saturated linear C1-C10 or branched C3-C10 alkyl group; in particular a linear C1-C6 alkyl group or a branched C3-C6 alkyl group, preferably a C1-C4 alkyl group such as a methyl group.

[0155] Preferably, in formulas (I) and (I') or (III) and (III'), R3 represents a hydrogen atom.

[0156] According to one embodiment, in formulas (I) and (I') or (III) and (III'), R4 represents: a hydrogen atom, a saturated linear C1-C10 or branched C3-C10 alkyl group; in particular a linear C1-C6 alkyl group or a branched C3-C6 alkyl group, preferably a C1-C4 alkyl group such as a methyl or ethyl group.

[0157] Preferably, in formulas (I) and (I') or (III) and (III'), R4 represents a linear C1-C10 or branched C3-C10 saturated alkyl group; in particular a linear C1-C6 alkyl group or a branched C3-C6 alkyl group, preferably a C1-C4 alkyl group such as a methyl or ethyl group.

[0158] Preferably, in formulas (I) and (I') or (III) and (III'),

[0159] - Ri represents a radical chosen from:

[0160] a) a hydrogen atom, and

[0161] b) a linear saturated C1-C6 or C3-C6 branched alkyl group optionally substituted by one or more groups, which may be identical or different, chosen from the group consisting of:

[0162]

[0163] i) -O-R3, and ü) -S-R3, preferably optionally substituted by one or more groups i);

[0164] - R2 represents a radical chosen from:

[0165] a) a hydrogen atom, and

[0166] b) a linear C1-C10 or branched C3-C10 or cyclic C3-C8 or C5-C6 saturated hydrocarbon group, optionally substituted by one or more groups, which may be the same or different, chosen from the group consisting of:

[0167] i) -O-R3,

[0168] ii) -S-R3,

[0169] iii) -C(O)-O-R3, and

[0170] iv) a phenyl group optionally substituted by one or more hydroxyls and / or by one or more C1-C4 alkoxy radicals such as methoxy, • preferably substituted by one or more groups selected from i) and iii), preferably iii) such as carboxy; and

[0171] - R3 represents a radical chosen from the group consisting of:

[0172] a) a hydrogen atom, and

[0173] b) a linear C1-C6 or branched C3-C6 saturated alkyl group,

[0174] - R4 represents a radical chosen from the group consisting of:

[0175] a) a hydrogen atom, and

[0176] b) a linear C1-C6 or branched C3-C6 saturated alkyl group • preferably, R4 represents a linear saturated C1-C6, in particular C1-C4, alkyl group.

[0177] Preferably, the compounds of formula (I) or (III), the tautomers of formula (I') or (III'), their acid or base salts, organic or mineral, their solvates, such as hydrates, their optical isomers, their geometric isomers and their mixtures, are such that:

[0178] - Ri represents a radical chosen from:

[0179] a) a hydrogen atom, and

[0180] b) a linear C1-C4 or branched C3-C4 saturated alkyl group optionally substituted by one or more groups, identical or different, chosen from i) -OR3 more preferably unsubstituted;

[0181] - R2 represents a radical chosen from:

[0182] a) a hydrogen atom, and

[0183] b) a linear C1-C10 or branched C3-C10 or cyclic C3-C8 or C5-C6 saturated hydrocarbon group, optionally substituted by one or more groups, which may be the same or different, chosen from

[0184] i) -O-R3,

[0185] iii) -C(O)-O-R3, and

[0186] iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more C1-C4 alkoxy radicals; and

[0187] - R3 represents a radical chosen from:

[0188] a) a hydrogen atom;

[0189] b) a saturated linear C1-C4 or branched C3-C4 alkyl group such as methyl or ethyl; and

[0190] - R4 represents a radical chosen from

[0191] a) a hydrogen atom, and

[0192] b) a linear C1-C6 or branched C3-C6 saturated alkyl group; • preferably, R4 represents a linear saturated C1-C6, in particular C1-C4, alkyl group.

[0193] Preferably, the thiopyridinone compound of formula (I) and (!') or (III) and (III') is selected from the group consisting of compounds III-1 to III-24 below, their tautomers, their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, in particular compounds III-1, III-2, III-4, III-6, III-7, III-9, III-11, III-12, III-14, III-15, III-16, III-17, III-18, III-19, III-20 or III-21, more particularly, III-1, III-9, III-16, III-18, III-19, III-20 or III-21, preferably, III-18, III-19, III-20 or III-21, and more preferably, III-19 or III-20, even more preferably III-20: N° Structure Nom chimique III-1 [f 'Y H N-éthyl-2-thioxo-1,2-dihydropyri dine- 3 -carboxamide III-2 / % / ' N-méthyl-2-thioxo-1,2-dihydropy ridine-3-carboxamide III-3 N-octyl-2-thioxo-1,2-dihydropyri dine- 3 -carboxamide III-4 4 ..¼ N-benzyl-2-thioxo-1,2-dihydropyr idine- 3 -carboxamide III-6 y ' [ h N-cyclohexyl-2-thioxo-1,2-dihydr opyridine-3-carboxamide III-7 N- [2-(4-méthoxyphényl)éthyl] -2-t hioxo-1,2-dihydropyridine-3-carb oxamide III-8 xVf" x'"'' <X -J1 N-(2-méthylpropyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide III-9 £: y $ H l? "X-'" X'v$ N-pentyl-2-thioxo-1,2-dihydropyr idine- 3 -carboxamide III-10 N-nonyl-2-thioxo-1,2-dihydropyri dîne- 3 -carboxamide III-11 O / \ 7 / 7' / / \ ( / \=J N-(2-hydroxyéthyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide III-12 -W. 'S\.v h i ! ■ k l H N,N-diéthyl 2-mercaptonicotinamide III-13 G r XT T.....\ V Jix \ 0H V's €H.S N-éthyl-N-(2-hydroxyéthyl)-2-thi oxo-1,2-dihydropyridine-3-carbox amide III-14 .--¼ XX ..“H N- (2,3 -dihy droxypropy 1) -2-thioxo -1,2-dihydropyridine-3-carboxami of III-15 To Jk N-(l,3-dihydroxypropan-2-yl)-2-t hioxo-1,2-dihydropyridine-3-carb oxamide III-16 x' H x'X'x x / r\ ' x) N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl alaninate III-17 ^Xi X N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]phenyl ethyl alaninate III-18 <“5 : '-y-" i ŒL N-methyl-N- [(2-thioxo-1,2-dihydr opyridin-3-yl)carbonyl]ethyl glycinate III-19 O ■ xx x N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]ethyl glycinate III-20 a m-2i H N-methyl-N-[(2-thioxo-1,2-dihydr opyridin-3-yl)carbonyl]glycine III-22 YYN,N-bis(2-hydroxyethyl)-2-thioxo -1,2-dihydropyridine-3-carboxami of III-23 N-(3-methoxypropyl)-2-thioxo-1, 2-dihydropyridine-3-carboxamide III-24 X Ja A N-butyl-2-thioxo-1,2-dihydropyri dine-3-carboxamide

[0194] Preferably, the thiopyridinone compound(s) of formula (I) or (!') is or are chosen from the group consisting of the compounds of formula (II) or (II'), the compounds of formula (III) or (III'), and / or one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0195] Preferably, the thiopyridinone compound(s) of formula (I) or (I') is or are chosen from the group consisting of the compounds of formula (IIA) or (IIB), the compounds of formula (III) or (III'), and / or one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0196] Preferably, the thiopyridinone compound(s) of formula (I) or (I') is or are chosen from the group consisting of the compounds of formulas (IIa) to (III) or (II'a) or (II'i), the compounds of formula (III) or (III'), and / or one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0197] Preferably, the thiopyridinone compound(s) of formula (I) or (I') is(are) chosen from the group consisting of compounds of formulae (IIa) to (IIi) or (II'a) to (II'i), in particular the compound of formula (IIa) or (II'a), compounds of formula III-1 to III-24, and / or one of their tautomers, one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0198] More preferably, the thiopyridinone compound(s) of formula (I) or (I') is or are chosen from the group consisting of the compounds of formulas (IIa) to (III) or (II'a) to (II'i), in particular the compound of formula (IIa) or (II'a), the compounds III-1, III-2, III-4, III-6, III-7, III-9, III-11, III-12, III-14, III-15, III-16, III-17, III-18, III-19, III-20 or III-21, and / or one of their tautomers, one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0199] Even more preferably, the thiopyridinone compound(s) of formula (I) or (I') is or are chosen from the group consisting of the compounds of formulas II-1, II-2, III-4, III-6, III-7, III-9, III-11, III-12, III-14, III-15, III-16, III-17, III-18, III-19, III-20 or III-21, and / or one of their tautomers, one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0200] Advantageously, the thiopyridinone compound(s) of formula (I) or (I') is or are chosen from the group consisting of the compounds of formulas II-1, II-2, II'-1 or II-2 or compound III-19 or compound III-20, and / or one of their tautomers, one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0201] Even more advantageously, the thiopyridinone compound(s) of formula (I) or (I') is or are chosen from the group consisting of the compounds of formulas 112 or 11'2 or the compound III-20, and / or one of their tautomers, one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0202] Acceptable solvates of compounds of formula (I) or (I'), compounds of formula (II) or (II'), compounds of formula (III) or (III') include conventional solvates such as those formed during the preparation of said compounds due to the presence of solvents.

[0203] For example, solvates due to the presence of water or linear or branched alcohols such as ethanol or isopropanol may be cited.

[0204] Optical isomers include enantiomers and diastereoisomers.

[0205] Geometric isomers include isomers having a geometric configuration Z / Z, Z / E, E / Z and E / E. Composition

[0206] The composition Cl according to the invention comprises at least one compound of formula (I) or (!), as described previously, and / or one of its acid or base salts, organic or mineral, one of its solvates, such as hydrates, one of its optical isomers, one of its geometric isomers, and mixtures thereof.

[0207] Composition C2 according to the invention comprises at least one compound of formula (II) or (II'), as described previously, and / or one of its acid or base salts, organic or mineral, one of its solvates, such as hydrates, one of its optical isomers, one of its geometric isomers, and mixtures thereof.

[0208] Composition C3 according to the invention comprises at least one compound of formula (III) or (III'), as described previously, and / or one of its acid or base salts, organic or mineral, one of its solvates, such as hydrates, one of its optical isomers, one of its geometric isomers, and mixtures thereof.

[0209] In other words, the composition Cl according to the invention comprises at least one thiopyridinone compound of formula (I) or (I'), and / or one of its acid or base salts, organic or mineral, one of its solvates, such as hydrates, one of its optical isomers, one of its geometric isomers, and mixtures thereof.

[0210] The compound(s) of formula (I) or (I') is or are as described above.

[0211] The composition Cl according to the invention may comprise at least two thio compounds distinct pyridinone, and of formula (I) or (I') as described above.

[0212] Thus, the composition Cl according to the invention can comprise a single thiopyridinone compound of formula (I) or (I') or a combination of different thiopyridinone compounds of formula (I) or (I').

[0213] According to a particular embodiment, the composition Cl according to the invention comprises at least two compounds of formula (I) or (I'), preferably two compounds of formula (I) or (I').

[0214] Preferably, the composition C1 according to the invention comprises at least one compound of formula (I) or (I') chosen from the group consisting of the compounds of formula (II) or (II'), as described above, the compounds of formula (III) or (III'), as described above, and / or one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0215] The compound(s) of formula (II) or (II') and of formula (III) or (III') are as described above.

[0216] More preferably, the composition C1 according to the invention comprises at least one compound of formula (I) or (I') chosen from the group consisting of the compounds of formula (IIA) or (IIB), in particular chosen from compounds (IIa) to (IIi) or (II'a) to (II'i) as defined above, the compounds of formula (III) or (III'), and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0217] Preferably, the composition C1 according to the invention comprises at least one compound of formula (I) or (I') chosen from the group consisting of the compounds of formula (IIa) to (IIi) or (II'a) to (II'i), in particular the compound of formula (IIa) or (II'a), the compounds of formula III-1 to III-24, and / or one of their tautomers, one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0218] More preferably, the composition C1 according to the invention comprises at least one compound of formula (I) or (I') chosen from the group consisting of the compounds of formulas (IIa) to (IIi) or (II'a) to (II'i), in particular the compound of formula (IIa) or (II'a), the compounds III-1, III-2, III-4, III-6, III-7, III-9, III-11, III-12, III-14, III-15, III-16, III-17, III-18, III-19, III-20 or III-21, and / or one of their tautomers, one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0219] Even more preferably, the composition C1 according to the invention comprises at least one compound of formula (I) or (I') chosen from the group consisting of the compounds of formulas II-1, II-2, II'-1 or II-2, the compounds III-1, III-2, III-4, III-6, III-7, III-9, III-11, III-12, III-14, III-15, III-16, III-17, III-18, III-19, III-20 or III-21, and / or one of their tautomers, one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0220] Advantageously, the composition C1 according to the invention comprises at least one compound of formula (I) or (I') chosen from the group consisting of the compounds of formulas II-1, II-2, II'-1, II-2, compound III-19, compound III-20, and / or one of their tautomers, one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0221] As indicated above, the present invention relates in particular to a composition C2 comprising at least one compound of formula (II) or (II'), as described previously, and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0222] Preferably, composition C2 comprises at least one compound of formula (II) or (II') chosen from the group consisting of compounds of formula (IIA) or (IIB), in particular chosen from the group consisting of compounds of formulas (IIa) to (IIi) or (II'a) to (II'i), as defined above, more particularly the compound of formula (IIa) or (II'a), even more preferentially from compounds of formulas II-I, II-II, their tautomers, their salts, isomers and / or solvates.

[0223] According to one embodiment, composition C1 denotes a composition C2.

[0224] According to another embodiment, the composition C1 according to the invention comprises at least one compound of formula (III) or (III'), as described above, preferably chosen from the group consisting of the compounds of formula III-1 to III-24, more preferably chosen from the group consisting of the compounds of formula III-1, III-2, III-4, III-6, III-7, III-9, III-11, III-12, III-14, III-15, III-16, III-17, III-18, III-19, III-20 or III-21, even more preferably III-1, III-9, III-16, III-18, III-19, III-20 or III-21, preferably III-18, III-19, III-20 or III-21, and more preferably III-19 or III-20, even more preferably III-20 and / or one of their tautomers, one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

[0225] In other words, according to one embodiment, composition C1 designates a composition C3.

[0226] According to a preferred embodiment, the composition C1 or C2 according to the invention comprises at least one compound of formula (I) or (I') chosen from the group consisting of the compounds of formula (II) or (II'), as described above, their salts, isomers and / or solvates, and optionally at least one compound of formula (I) or (I') chosen from the group consisting of the compounds of formula (III) or (III'), as described above, their salts, isomers and / or solvates.

[0227] In accordance with this preferred embodiment, the composition C1 or C2 according to the invention comprises several compounds of formula (I) or (I'), at least one being chosen from the compounds of formula (II) or (II') and at least one being chosen from the compounds of formula (III) or (III'), as well as their salts, isomers and / or solvates.

[0228] In other words, in accordance with this preferred embodiment, the composition C1 or C2 according to the invention comprises: - at least one compound of formula (I) or (I') selected from the group consisting of compounds of formula (II) or (II'), in particular selected from the group consisting of compounds of formulas (IIa) to (IIi) or (II'a) to (II'i), in particular the compound of formula (IIa) or (II'a), their salts, isomers and / or solvates, and - at least one compound of formula (I) or (I') selected from the group consisting of compounds of formula (III) or (III'), in particular selected from the group consisting of compounds of formulas III-1 to III-24, more preferably selected from the group consisting of compounds of formulas III-1, III-2, III-4, III-6, III-7, III-9, III-ll, III-12, III-14, III-15, III-16, III-17, III-18, III-19, III-20 or III-21, more preferably selected from the group consisting of the compounds of formulas III-19 and III-20 as well as their tautomers, their salts, isomers and / or solvates.

[0229] In other words, in accordance with this particular embodiment, the com- position Cl or C2 according to the invention comprises at least one compound of formula (II) or (II'), as well as their salts, isomers and / or solvates, and at least one compound of formula (III) or (III'), as well as their salts, isomers and / or solvates.

[0230] Preferably, in accordance with this embodiment, the composition C1 or C2 according to the invention comprises at least one compound of formula (II) or (II'), chosen from the group consisting of the compounds of formulas (IIa) to (III) or (II'a) to (II'i), in particular the compound of formula (IIa) or (II'a), and at least one compound of formula (III) or (III') chosen from the group consisting of the compounds of formulas III-1 to III-24, more preferably chosen from the group consisting of the compounds of formulas III-1, III-2, III-4, III-6, III-7, III-9, III-11, III-12, III-14, III-15, III-16, III-17, III-18, III-19, III-20 or III-21, even more preferably chosen from the group consisting of compounds III-19 and III-20 as well as their tautomers, their salts, isomers and / or solvates.

[0231] More preferably, the composition C1 or C2 according to the invention comprises at least one compound of formula (II) or (II'), chosen from the group consisting of the compounds of formulas (II-1) and (II-2) as well as their tautomers, their salts, isomers and / or solvates, and at least one compound of formula (III) or (III') chosen from the group consisting of the compounds of formulas III-1, III-9, III-16, III-18, III-19, III-20 or III-21, preferably III-18, III-19, III-20 or III-21, and more preferably III-19 or III-20, as well as their salts, isomers and / or solvates.

[0232] Advantageously, the composition C1 or C2 according to the invention comprises at least one compound of formula (II) or (II') chosen from the group consisting of the compounds of formula (II-1), (II-2), their acid or base salts, organic or mineral, their geometric isomers, their optical isomers, their solvates such as hydrates, and their mixtures, and at least one compound of formula (III-20), its tautomer, one of its acid or base salts, organic or mineral, its solvates, its optical isomers, its geometric isomers, and their mixtures.

[0233] The composition C1 or C2 or C3 according to the invention, as described above, may be aqueous, preferably is aqueous.

[0234] The pH of the composition Cl or C2 or C3 is preferably acidic, i.e. the pH value is preferably strictly less than 7.

[0235] Composition C1 or C2 or C3 may further comprise at least one organic solvent, preferably chosen from the group consisting of C1-C4 alcohols, in particular ethanol.

[0236] In other words, the composition C1 or C2 or C3 according to the invention may comprise water and optionally at least one organic solvent, as defined above, preferably water and at least one organic solvent as defined above.

[0237] Composition Cl can be found in all the forms conventionally used in hair care, in particular in the form of lotions or thickened lotions.

[0238] Composition C2 can be found in all forms conventionally intended for application to keratin materials such as skin or keratin fibers. Thus, composition C2 can be in the form of lotions, thickened lotions, sprays, more or less fluid creams, gels, roll-ons. Compositions C2 can be direct or inverse emulsions.

[0239] In particular, composition C2 can be found in all forms conventionally intended for the care of keratin materials, for example for the care of the skin and / or hair.

[0240] The composition C1 or C2 or C3 according to the invention preferably contains at least 0.001% by weight of thiopyridinone compounds of formula (I) or (I'), preferably at least 0.003% by weight, relative to the total weight of the composition.

[0241] Thus, the quantity of the thiopyridinone compound(s) of formula (I) or (!') in the composition C1 or C2 or C3 according to the invention is preferably between 0.001% and 70% by weight, more preferably between 0.003% and 60% by weight, even more preferably between 0.005% and 50% by weight, even more preferably between 0.01 and 40% by weight, relative to the total weight of the composition.

[0242] Preferably, the composition C1 or C2 according to the invention comprises at least 0.001% by weight of thiopyridinone compounds of formula (II) or (II'), as described above, relative to the total weight of the composition.

[0243] Preferably, the composition C1 or C3 according to the invention comprises at least 0.001% by weight of thiopyridinone compounds of formula (III) or (III'), as described above, preferably at least 0.05% by weight, more preferably at least 0.1% by weight, relative to the total weight of the composition. Use

[0244] As indicated above, the present invention relates to the use of at least one compound of formula (I) or (I'), as described above, and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, or of at least one composition Cl comprising the or them, as defined above, for shaping keratin fibers, in particular human keratin fibers such as hair.

[0245] The compound(s) of formula (I) or (I'), the compound(s) of formula (II), (II') as well as the compound(s) of formula (III) and (III') used are as defined above.

[0246] The composition C1 or C2 or C3 used in accordance with the present invention is as defined above.

[0247] Preferably, the invention relates to the use of at least one compound of formula (I) or (!') chosen from the group consisting of the compounds of formula (II) or (II') as described above, preferably chosen from the compounds of formula (IIA) or (IIB), the compounds of formula (III) or (III'), as described above, and / or one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, or at least one composition comprising it or them, as defined above, for shaping keratin fibers, in particular human keratin fibers such as hair.

[0248] Preferably, the invention relates to the use of at least one compound of formula (II) or (II') as described above, one of their acid or base salts, organic or mineral, one of their optical isomers, geometric isomers, their solvates such as hydrates and / or their mixtures, or at least one composition C2 comprising it or them, as defined above for the treatment of keratin materials such as skin or keratin fibers, preferably keratin fibers, in particular human keratin fibers such as hair.

[0249] Preferably, the invention relates to the use of at least one compound of formula (II) or (II') chosen from the compounds of formulas (IIA) or (IIB), in particular chosen from the group consisting of the compounds of formulas (IIa) to (IIi) or (II'a) to (II'i), in particular the compounds of formula (IIa) or (II'a), more preferably chosen from the group consisting of the compounds of formulas (II-1), (II-2), their tautomers, their salts, isomers and / or solvates, or at least one composition comprising it or them, as defined above, for the treatment of keratin materials such as skin or keratin fibers, preferably keratin fibers, in particular human keratin fibers such as hair.

[0250] More preferably, the use of at least one compound of formula (II) or (II') as described above or of at least one composition C2 comprising at least one compound of formula (II) or (II') is a use for the treatment of keratin fibers, in particular human keratin fibers such as hair, and more particularly for the shaping of keratin fibers, in particular human keratin fibers such as hair.

[0251] Preferably, the invention relates to the use of at least one compound of formula (III) or (III') as described above, preferably chosen from the group consisting of the compounds of formulas III-1 to III-24, more preferably chosen from the group consisting of the compounds of formulas III-1, III-2, III-4, III-6, III-7, III-9, III-11, III-12, III-14, III-15, III-16, III-17, III-18, III-19, III-20 or III-21, in particular chosen from the group consisting of compounds III-19 and III-20, even more particularly compound III-20, as well as their tautomers, their salts, isomers and / or solvated, or at least one composition comprising it or them, as defined above, for shaping keratin fibers, in particular human keratin fibers such as hair.

[0252] Advantageously, the use according to the invention is a use for maintaining the shaping of keratin fibers, in particular human keratin fibers such as hair.

[0253] Still advantageously, the use according to the invention is a use for modifying the shape of keratin fibers, in particular human keratin fibers such as hair.

[0254] More preferably, the keratin fibers are sensitized keratin fibers, in particular by at least one chemical treatment such as a permanent deformation process, for example a straightening or perming, coloring and / or bleaching process.

[0255] Even more preferably, the keratin fibers are colored and / or bleached keratin fibers, in particular bleached. Process for treating keratin fibers

[0256] As indicated above, the subject of the invention is in particular a process for shaping keratin fibers, in particular human keratin fibers such as hair, comprising at least the application to said fibers of at least one compound of formula (I) or (I'), as described above, and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, or of at least one composition, as defined above, comprising it or them.

[0257] The compound(s) of formula (I) or (I'), the compound(s) of formula (II), (II') as well as the compound(s) of formula (III) and (III'), used in the process according to the invention, are as defined above.

[0258] The composition used in the method according to the invention is as defined above. The composition thus comprises at least one compound of formula (I) or (I'), as defined above.

[0259] Preferably, the method according to the invention comprises at least the application to said fibers of at least one compound of formula (I) or (I') chosen from the group consisting of the compounds of formula (II) or (II'), as defined above, the compounds of formula (III) or (III'), as defined above, and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, or of at least one composition comprising it or them.

[0260] The invention relates in particular to a method for treating keratin fibers, in particular for shaping keratin fibers, in particular keratin fibers. Human fibers such as hair, comprising at least the application to said fibers of at least one compound of formula (II) or (II'), as defined above, preferably chosen from the compounds of formulas (IIA) or (IIB), in particular chosen from the group consisting of the compounds of formulas (IIa) to (IIi) or (II'a) to (II'i), in particular the compounds of formula (IIa) or (II'a), more preferably chosen from the group consisting of the compounds of formulas (II-1), (II-2), their tautomers, their salts, isomers and / or solvates, or at least one composition comprising it or them, as defined above.

[0261] The invention also relates to a process for shaping keratin fibers, in particular human keratin fibers such as hair, comprising at least the application to said fibers of at least one compound of formula (III) or (III'), as defined above, preferably chosen from the compounds of formulas III-1 to III-24, more preferably chosen from the group consisting of the compounds of formulas III-1, III-2, III-4, III-6, III-7, III-9, III-11, III-12, III-14, III-15, III-16, III-17, III-18, III-19, III-20 or III-21, in particular chosen from the group consisting of compounds III-19 or III-20, even more particularly compound III-20, as well as their tautomers, their salts, isomers and / or solvates, or at least one composition including it or them, as defined above.

[0262] Preferably, the method according to the invention is a method for shaping keratin fibers, in particular human keratin fibers such as hair.

[0263] Advantageously, the method according to the invention is a method for modifying the shape of keratin fibers, in particular human keratin fibers such as hair.

[0264] Preferably, the application or contacting of at least one compound of formula (I) or (I'), as described above, or of at least one composition as defined above, is carried out on dry or wet keratin fibers.

[0265] More preferably, the application or contacting of at least one compound of formula (I) or (I'), as described above, or of at least one composition as defined above, is carried out on dry or damp hair.

[0266] Preferably, the step of bringing into contact or applying the compound(s) of formula (I) or (I') or the composition comprising it or them, includes a exposure time of between 10 seconds and 30 minutes, preferably between 30 seconds and 15 minutes.

[0267] Preferably the contacting or application step is repeated.

[0268] Preferably, the keratin fibers are sensitized, more preferably by at least one permanent deformation process, for example a straightening process or permanent, or at least one coloring and / or bleaching process, in particular bleaching.

[0269] More preferably, the hair is sensitized hair.

[0270] Preferably, the method according to the invention comprises at least one step of heating the keratin fibers.

[0271] Preferably, the method according to the invention comprises at least one step of heating the keratin fibres carried out after the application of at least one compound of formula (I) or (I') or of at least one composition comprising at least one compound of formula (I) or (I').

[0272] The method consists in particular of: i. bringing the keratin fibers into contact with at least one compound of formula (I) or (I'), as defined above, or a composition containing it or them, ii. possibly leave to stand, preferably leave to stand for a setting time of between 10 seconds and 30 minutes iii. possibly rinse, preferably rinse, iv. optionally carry out a heating step, preferably carry out a heating step for a duration ranging from 2 minutes to 1 hour, preferably ranging from 5 minutes to 30 minutes, more preferably ranging from 8 minutes to 20 minutes.

[0273] Steps i) to iii) may be repeated.

[0274] General process for the synthesis of compounds of formula (II) or (ID

[0275] The compounds of formula (II) or (II') according to the invention can be obtained for example from the corresponding compounds of formula (III) and having a terminal carboxylic acid function via a coupling step between the carboxylic acid function of the compound of formula (III) and the amine function of a compound of formula (IV).

[0276] The compounds of formula (III) or (III') used to obtain the compounds of formula (II) are thus the compounds of formula (III) or (III') as defined previously and such that:

[0277] - Ri is as defined for compounds of formula (III) or (III') and

[0278] - R2 denotes a radical b) a linear C1-C12 or branched saturated hydrocarbon group in C3-Ci2 or cyclic in C3-C8, preferably acyclic and said hydrocarbon group being substituted by a radical iii) -C(O)-OH, and optionally substituted by one or more groups, identical or different, chosen from:

[0279] i) -O-R3,

[0280] ii) -S-R3,

[0281] iv) a C5-C12 aryl group, optionally substituted by one or more hy- droxyls and / or by one or more CrC8 alkoxy radicals and

[0282] - R3 denotes a radical chosen from the group consisting of:

[0283] a) a hydrogen atom, and

[0284] b) a linear C1-C10 or branched C3-C10 saturated alkyl group; and

[0285] c) a thiol function or alcohol function protecting group.

[0286] The thiol function or alcohol function protecting groups are for example those mentioned in the document entitled "Protective Groups in Organic Synthesis", second edition, Theodora W. Greene & Peter GM Wuts, Wiley Interscience Publication, John Wiley & sons INC, 1991, Chapter 2 = Protection of the hydroxyl group including 1,2 and 1,3 diols and chapter 6 = Protection of the Thiol group.

[0287] The compounds of formula (IV) denote in particular amino acids H2N- B-COOR5 in which: - B denotes a divalent cyclic or acyclic radical, preferably acyclic, linear or branched, comprising from 1 to 10 carbon atoms, optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or their associations such as (thio)ester or (thio)amide(s) -C(X)-N(R')- or -N(R')-C(X)- and / or said group B being optionally substituted, in particular by one or more hydroxyl or thiol groups optionally protected by protective groups; and - R5 denotes a protecting group for a carboxylic acid function such as an ester function, in particular a C1-C4 alkyl ester such as an ethyl ester, and - X represents an oxygen atom, sulfur atom, preferably an oxygen atom; and - R' represents a hydrogen atom or a C1-C4 alkyl group such as methyl, preferably a hydrogen atom.

[0288] As examples of compounds of formula (IV), mention may be made, for example, of glycine, alanine, beta-alanine, leucine, isoleucine, serine, valine, cysteine, the carboxylic acid function of which is protected, for example, by the protective groups mentioned in the document entitled "Protective Groups in Organic Synthesis", second edition, Theodora W. Greene & Peter GM Wuts, Wiley Interscience Publication, John Wiley & sons INC, 1991, Chapter 5 = Protection of the carboxyl group, in particular by an ester function, more precisely by a C1-C4 alkyl function such as an ethyl ester.

[0289] When the compounds of formula (IV) contain one or more asymmetric carbons, each of them may be of R or S configuration or in racemic form.

[0290] When the compounds of formula (IV) denote amino acids, these are L configuration preference.

[0291] The coupling between the carboxylic acid function of a compound of formula (III) and the amine function of a compound of formula (IV) is carried out using conventional activating or coupling reagents such as carbodiimides such as DCC (= di-cyclohexylcarbodiimide) or water-soluble forms of carbodiimides such as EDC (= N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride), phosphonium salts such as BOP (= benzotriazol-l-yloxy) tris(dimethylamino)phosphonium hexafluorophosphate), PyBOP (=(benzotriazol-l-yloxy)tripyrrolidinophosphonium hexafluorophosphate), PyBROP (= bromotripyrrolidinophosphonium hexafluorophosphate), PyCloP (= chlorotripyr-rolidinophosphonium hexafluorophosphate), or using reagents such as PyClU (= chloro-N,N,N',N'-bis(tetramethylene) formamidinium hexafluorophosphate), N-hydroxysuccinimide, EEDQ (= l-ethoxycarbonyl-2-ethoxy-l,2-dihydroquinoline), CDI (= carbonyldiimidazole),or chloroformates such as ethyl chloroformate or isobutyl chloroformate. When coupling is carried out using coupling reagents such as carbodiimides, additives such as HOBt (= 1-hydroxybenzotriazole) or N-hydroxysuccinimide may be added during the reaction to limit racemization.

[0292] Preferably, the coupling is carried out with carbodiimides with or without the addition of 1-hydroxybenzotriazole.

[0293] The coupling reaction between a compound of formula (III) or (III') and a compound of formula (IV) is carried out in a solvent or a mixture of solvents which are preferably aprotic dipolar, preferably dimethylformamide (DMF), N-methylpyrrolidone (NMP), or aprotic solvents such as 1,2-dimethoxyethane (DME), tetrahydrofuran (THF), dioxane, pure or as a mixture.

[0294] When the compound (IV) carries a carboxylic acid function protected by a protective group R5, the coupling reaction can be followed by a step of deprotection of the carboxylic acid function. The deprotection reaction is described in particular in the document entitled "Protective Groups in Organic Synthesis", second edition, Theodora W. Greene & Peter GM Wuts, Wiley Interscience Publication, John Wiley & sons INC, 1991. The conditions of this possible deprotection step are determined by the nature of the protective group R5.

[0295] For example, if the carboxylic acid function of (IV) is in ester form (i.e. R5 is for example a C1-C4 alkyl such as ethyl), after coupling, the ester function can be saponified by a preferably mineral base such as sodium hydroxide.

[0296] The invention is illustrated in more detail in the following non-limiting examples. Example :

[0297] Example 1: Synthesis of the compound of formula (111-20)

[0298] Step 1: Synthesis of compound 3 - N- [(2-thioxo-l.2-dihydropyridin-3-yDcarbonyl1glycinate ethyl (II1-19) Route 1: via 2-mercaptonicotinic acid

[0300] Thionicotinic acid is introduced into acetonitrile and then carbonyldiimidazole (CDI) into a flask. The resulting mixture is heated to reflux for one hour and then left at room temperature.

[0301] After returning to room temperature, ethyl glycinate hydrochloride is added and then the resulting mixture is heated again at a temperature of 60°C for 3 hours. The mixture is then left at room temperature overnight.

[0302] After the night, the reaction medium is evaporated. The residue is taken up in dichloromethane and washed twice with 2 N HCl.

[0303] The organic phase is dried over anhydrous sodium sulfate then evaporated and purified on silica Dichloromethane 97 / methanol 3.

[0304] The fractions are evaporated.

[0305] A light yellow powder is obtained. Route 2: via 2-chloronicotinic acid

[0307] In a three-necked flask, 2-chloronicotinic acid (250.0 g, 1.587 mol) is introduced into ethyl acetate (500 ml) then SOC12 (210.0 g, 1.761 mol) is added dropwise into the mixture.

[0308] The whole is heated to reflux until complete conversion. Once the reaction is complete, the mixture is cooled to room temperature and diluted with ethyl acetate (375ml).

[0309] A solution of ethyl glycinate hydrochloride (265.8g, 1.904mol) diluted in water (400ml) and triethylamine (393.5g, 3.88mol) is then added to the mixture.

[0310] The whole is stirred for a period of 3 to 4 hours and then the ethyl acetate is removed under vacuum.

[0311] The aqueous solution thus obtained is then diluted with water (1250 ml) and then acidified with 3N HCl (25 ml).

[0312] Sodium thiosulfate (1379g, 5.555mol) is then added and the whole is then heated to reflux for 6 hours. After cooling to 10°C, the yellow solid is filtered and washed with water (3 times 750ml).

[0313] The crude product is then treated with carbon black in a 75 / 25 ethanol / water mixture.

[0314] The carbon black is then filtered while hot and the ethanol is evaporated. The whole is cooled to room temperature, then the product is filtered and dried under vacuum.

[0315] A light yellow powder is thus obtained.

[0316] The 1H NMR and mass spectra are consistent with the structure.

[0317] Melting point: 151°C (capillary tube)

[0318] Step 2: Synthesis of the N- compound [(2-thioxo-l.2-dihydropyridin-3-yl)carbonyl1glycine from the compound obtained in step 1 NaOH EtOH

[0319] (III-20)

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337] In a three-necked flask are introduced ethyl N-[(2-thioxo-1,2-dihydropyridin-3-yl)carbonyl]glycinate (48 g, 0.317 mol) and a 95% EtOH solution (48 mL). The resulting mixture is cooled to 10°C. A solution of NaOH (16g) in 144 mL of water is added dropwise into the mixture. The organic solvent is evaporated and 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 product thus obtained 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) Example 2: Synthesis of compounds 1 and 2 Compound 1 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 whole is stirred until a clear solution is obtained then carbonyldii-midazole (16.809 g, 1.1 Eq, 103.67 mmol) is added portionwise. 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 whole is stirred for one hour at a temperature of 20°C. The reaction medium is then slowly added to a 10% aqueous NaHCO3 solution with stirring. The suspension obtained is filtered through a sintered filter to yield a solid which is rinsed with distilled water. The solid is dried at a temperature of 50°C under vacuum to obtain ethyl (2-mercaptonicotinoyl)glycylglycinate (compound 1) in the form of a yellow powder. Spectroscopic analyses are consistent with the indicated structure. Compound 2

[0338] In a 250 mL flask are introduced compound 1, as obtained previously, (ethyl (2-mercaptonicotinoyl)glycylglycinate) (13.440 g, 1 Eq, 45.202 mmol) and distilled water (70 mL).

[0339] While stirring, a 50% sodium hydroxide solution is added until a pH value of around 12-13 is reached, keeping the temperature below 25°C. The resulting mixture is stirred for one hour at a temperature of 25°C and then the pH is adjusted to a value of 2 with 37% hydrochloric acid.

[0340] The suspension obtained is filtered through a sintered filter and then the resulting solid is rinsed with distilled water.

[0341] The solid is dried at 50°C under vacuum to obtain the compound 2 (2-mercaptonicotinoyl)glycylglycine in the form of a yellow powder. Example 3: Evaluation in shaping Preparation of the compositions

[0342] Compositions A (outside the invention), B and C (according to the invention) were prepared from the ingredients indicated in the table below: Compositions Compound Mass Ethanol Water PH A (not invention) - 50mL 50mL 4.0 (adjusted with HCl) B (invention) Compound (III-20) obtained example 1 0.25g 12.5mL 12.5mL 4.0 (adjusted with NaOH) C (invention) Compound 2 obtained example 2 0.20g 12.5mL 12.5mL 3.9 (not adjusted) Preparing the wicks

[0343] Locks of Caucasian hair, damaged by two successive bleachings, of 2.7g and 20cm long (alkaline solubility of 19, type II) are washed with DOP shampoo, then wrung out between the fingers (2 passes). The locks are then placed on a flat surface and compositions A (comparative), B (invention) and C (invention) are applied to said locks with a bath ratio of 1 (namely 1g of composition per 1g of hair).

[0344] The hair is then kneaded with the fingers using circular movements throughout each strand (5 times), then the strands are left for 5 minutes. The strands are then rinsed with tap water for 30 seconds and then wrung out.

[0345] These different steps are repeated to have 10 applications in total. After the tenth application the strands are dried at 60°C (10 min / g of hair).

[0346] Method for evaluating shape retention - test method

[0347] The strands are shampooed (DOP), wrung out, pre-dried with a paper towel.

[0348] The strands are then rolled using a curler (0 = 2cm) and then dried at a temperature of 60°C for 10 minutes. The curler is then removed and the strands are hung vertically.

[0349] The length of the wicks for each of compositions A, B and C is measured initially (t=0) then after a period of 4 hours (t=4 hours). Initial length (cm) tO Final length (cm) t4h Increase in Length (cm) t4h - tO Wick A (untreated) 11.2 18.6 7.4 Wick treated 10 times with composition B 11.8 15.8 4.0 Wick treated 10 times with composition C 11.5 15.7 4.2

[0350] The increase in the length of the strands treated with composition B and composition C is much less significant than the strand treated with comparative composition A. This indicates better shape retention for the strands treated with composition B and composition C.

Claims

Claims

1. Process for shaping keratin fibers, in particular human keratin fibers, such as hair, comprising at least the application to said keratin fibers of at least one compound of formula (I) or (!) below, and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, or of at least one composition Cl comprising: OO (i) (D Formula (I) and (!') in which: - Ri denotes a radical chosen from the group consisting of: a. a hydrogen atom, b. a linear C1-C10 or branched C3-C10 saturated alkyl group optionally substituted by one or more groups, identical or different, chosen from the group consisting of i) -O-R3 and ii) -S-R3; - R2 denotes a cyclic or acyclic radical chosen from the group consisting of: a. a hydrogen atom, b. a linear C1-C12 or branched C3-C[2 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; said hydrocarbon group being optionally interrupted by one or more heteroatoms or groups, such as an atom oxygen, a sulfur atom, an NR' or (thio)carbonyl group, or combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-, or, c. a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; - R3 denotes a radical chosen from a) a hydrogen atom, b) a linear C1-C10 or branched C3-C10 saturated alkyl group - R4 denotes a radical chosen from the group consisting of a) a hydrogen atom, b) a linear C1-C10 or branched C3-C10 saturated alkyl group, c) an alkali metal, d) an alkaline earth metal, or e) an ammonium group; - X represents an oxygen atom, a sulfur atom, preferably an oxygen atom, - R' represents a hydrogen atom or a C1-C4 alkyl group, in particular C1, preferably represents a hydrogen atom;- it being understood that when R4 denotes e) an ammonium group, the electroneutrality of the compounds of formula (I) or (!') is ensured by one or more cosmetically acceptable anions such as halides preferably chosen from chloride or bromide.;

2. Method according to claim 1, characterized in that Ri represents a) a hydrogen atom.

3. Process according to claim 1 or 2, characterized in that R3 represents a) a hydrogen atom or a linear C1-C6 or branched C3-C6 saturated alkyl group, preferably R3 represents a) a hydrogen atom

4. Process according to any one of the preceding claims, characterized in that R4 represents a) a hydrogen atom, b) a linear saturated C1-C6, in particular C1-C4, alkyl group, or c) an alkali metal.

5. A method according to any preceding claim, ca- characterized in that R2 denotes b) a linear C1-C12 or branched C3-C12 saturated hydrocarbon group, optionally substituted by one or more groups, identical or different, chosen from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; said hydrocarbon group being interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

6. Process according to any one of claims 1 to 4, characterized in that R2 denotes b) a linear C1-C12 or branched C3-C12 saturated hydrocarbon group, substituted by one or more groups iii) -C(O)-O-R4; said hydrocarbon group being further optionally substituted by one or more groups, identical or different, chosen from the group consisting of i) -O-R3, ii) -S-R3, and iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals; said hydrocarbon group being further optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

7. Process according to any one of the preceding claims, characterized in that the compound(s) of formula (I) and (!') is or are chosen from the group consisting of the compounds of formula (II) or (II'), as well as one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures: 0 0 , II A 0 . 0 A 0 Ü X 1b Oh? CV (II) (II') Formulae (II) and (II') in which: - A represents a divalent hydrocarbon chain, saturated or unsaturated, preferably saturated, cyclic or acyclic, preferably acyclic, linear or branched, comprising from 1 to 10 carbon atoms, interrupted by one or more (thio)amide(s) -C(X)-N(R')- or (NR')-C(X)- groups, and optionally substituted by one or more groups, identical or different, chosen from the group consisting of i) -O-R3 and ii) -S-R3; - M denotes a radical chosen from the group consisting of a) a hydrogen atom, b) a linear C1-C10 or branched C3-C10 alkyl group, c) an alkali metal, d) an alkaline earth metal, or e) an ammonium group; preferably M represents a) a hydrogen atom or d) an alkali metal; - Ri has the same meaning as in claim 1 or 2; preferably, Ri represents a hydrogen atom; - R3 has the same meaning as in claim 1 or 3; preferably, R3 represents a hydrogen atom; - X has the same meaning as in claim 1; preferably X represents an oxygen atom; - R' has the same meaning as in claim 1; preferably, R' represents a hydrogen atom.

8. Process according to claim 7, characterized in that A represents a (C2-C6)alkylene group, linear or branched, preferably linear; said chain A being interrupted by a group -C(X)-N(R')- with X and R' as defined in claim 7, more particularly interrupted by a group -C(O)-N(H)-; in particular A represents a group CH2-C(O)-N(R')-CH2- or -CH2-N(R')-C(X)-CH2- with X and R' as defined in claim 7, preferably A represents a group -CH2-C(O)-N(H)-CH2-,

9. Process according to any one of the preceding claims, characterized in that the compound(s) of formula (I) or (I'), the compounds of formula (II) or (II') is or are chosen from the group consisting of the compounds of formula (IIA) or (IIB) below, their acid or base salts, organic or inorganic, their solvates, such as hydrates, their optical isomers, their geometric isomers and their mixtures: (IIA) (IIB) Formulas (IIA) and (IIB) in which: - Ra and Rb denote, independently of each other, a hydrogen atom or a C1-C4 alkyl radical optionally substituted by one or more hydroxyl (OH) or thiol (SH) radicals; and - n and m independently denote an integer equal to 1 or 2 or 3; preferably n and m are identical and are equal to 1; - M has the same meaning as for the compounds of formula (II) or (II'); particularly M represents a hydrogen atom, an alkali metal, or an alkyl group, linear or branched, C1-C4 alkyl such as methyl or ethyl, preferably a hydrogen atom or an alkali metal such as sodium or potassium.

10. Process according to any one of the preceding claims, characterized in that the compound(s) of formula (I) or (I'), the compounds of formula (II) or (II'), the compounds of formula (IIA) or (IIB) is or are chosen from the compounds of formula (IIa) to (Ili) or (II'a) to (II'i) below as well as their tautomers, their organic or mineral acid or base salts, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures:

11. with M as defined above, particularly M represents a hydrogen atom, an alkali metal, or a linear or branched C1-C4 alkyl group such as methyl or ethyl, more preferably a hydrogen atom or an alkali metal such as sodium or potassium. Process according to any one of the preceding claims, characterized in that the compounds of formula (I) or (I'), the compounds of formula (II) or (II'), the compounds of formula (IIA) or (IIB) are chosen from the compounds of formula (II-1) or (II-2) or (II-2), below as well as their acid or base salts, organic or mineral, in particular their sodium or potassium salts, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures:

12. Process according to any one of claims 1 to 4, characterized in that the thiopyridinone compound(s) of formula (I) and (!') is or are chosen from the group consisting of the compounds of formula (III) or (III'), as well as one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures: O O H (III) (IID Formulas (III) and (III') in which: - Ri is as defined in formula (I) or (I'), - R2 denotes a radical chosen from the group consisting of: a) a hydrogen atom, b) a linear C1-C12 or branched C3-C12 or cyclic C3-C8 saturated hydrocarbon group, optionally substituted by one or more groups, identical or different, chosen from: i) -O-R3, ii) -S-R3, iii) -C(0)-0-R4, and iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals, and (c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and / or by one or more C1-C8 alkoxy radicals, and - R3 denotes a radical chosen from the group consisting of: a) a hydrogen atom, and (b) a linear C1-C10 or branched C3-C10 saturated alkyl group; and - R4 denotes a radical chosen from a) a hydrogen atom, b) a linear saturated C1-C10 or branched C3-C10 alkyl group.

13. A method according to any one of claims 1 to 4 or 12, ca- characterized in that the compound(s) of formula (I) or (!') or the compounds of formula (III) or (III') are selected from the group consisting of compounds III-1 to III-24 below, their tautomers, their organic or mineral acid or base salts, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures: III-1 h HY* H N-ethyl-2-thioxo-1,2-dihydr opyridine-3-carboxamide III-2 \ / XX N-methyl-2-thioxo-1,2-dihy dropyridine- 3 -c arboxamide III-3 N-octyl-2-thioxo-1,2-dihydr opyridine-3-carboxamide III-4 rf"'yv yy Y'''' N-benzyl-2-thioxo-1,2-dihy dropyridine- 3 -c arboxamide III-6 x^---^ H 1 M %xy 3-carboxamide III-8 H .A_ <■> N-(2-méthylpropyl)-2-thiox o-1,2-dihydropyridine-3-car boxamide III-9 z\ X** Qj' N-pentyl-2-thioxo-1,2-dihy dropyridine- 3 -c arboxamide III-10 N-nonyl-2-thioxo-1,2-dihyd ropyridine- 3 -c arboxamide III-11 XN”"' H 0 / X OH N - (2-hy droxy éthy 1) -2-thiox o-1,2-dihydropyridine-3-car boxamide III-12 o ’ K l XZ Xi N,N-diéthyl 2-mercaptonicotinamide III-13 C ■•'* ' X‘X H Q / \ < '-....xjH \h. N-éthyl-N-(2-hydroxyéthyl) -2-thioxo-1,2-dihydropyridi ne-3-carboxamide III-14 X 1L iX. N-(2,3-dihydroxypropyl)-2-t hioxo-1,2-dihydropyridine-3-carboxamide III-15 û <* M À. ..qh H N- (1,3 -dihy droxypropan-2-yl)-2-thioxo-1,2-dihydropyr idine- 3 -carboxamide III-16 a S r . f \r * V / N-methyl-N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbon yl]ethyl glycinate III-19 III-21 Ü Jk CH.. ûH H N-methyl-N- [(2-thioxo-1,2-dihydropyridin-3-yl)carbon yl] glycine III-22 Jk* .,-iK N,N-bis(2-hydroxyethyl)-2-t hioxo-1,2-dihydropyridine-3-carboxamide III-23 N-(3-methoxypropyl)-2-thio xo-1,2-dihydropyridine-3-ca rboxamide III-24 N-butyl-2-thioxo-1,2-dihydr opyridine-3-carboxamide

14.

15.

16. in particular compounds III-1, III-2, III-4, III-6, III-7, III-9, III-11, III-12, ni-14, III-15, III-16, ni-17, m-18, III-19, III-20 or m-21, more particularly, III-1, III-9, III-16, III-18, III-19, III-20 or III-21, preferably, III-18, III-19, III-20 or III-21, and more preferably, the compound of formula III-20. Process according to any one of the preceding claims, characterized in that the keratin fibers are sensitized, preferably colored and / or bleached, in particular bleached. Use of at least one compound of formula (I) or (I'), as defined according to any one of claims 1 to 13, and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, or of at least one composition Cl containing it or them, for shaping keratin fibers, in particular human keratin fibers, such as hair. Use according to claim 15, characterized in that the compound(s) of formula (I) or (I') is or are chosen from the group consisting of the compounds of formula (II) or (II'), as defined according to any one of claims 7 to 11, the compounds of formula (III) or (III'), as defined according to claim 12 or 13, and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geo- isomers metrics and their mixtures.

17. Use according to claim 15 or 16, characterized in that the compound(s) of formula (I) or (!') is or are chosen from the group consisting of the compounds of formula (III) or (III') as defined according to claim 12 or 13, and / or one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

18. Compound of formula (II) or (II'), as defined according to any one of claims 7 to 11, and / or one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

19. Composition C2 comprising at least one compound of formula (II) or (II'), as defined according to claim 18, and / or one of their acid or base salts, organic or inorganic, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

20. Composition according to claim 19, characterized in that it further comprises at least one compound of formula (I) or (I') chosen from the group consisting of compounds of formula (III) or (III'), as defined according to claim 12 or 13, as well as their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

21. Composition according to claim 20, characterized in that it comprises at least one compound of formula (I) or (I') chosen from the compounds of formulae (II-1), (II-2), (II' 1), (II' 2), as defined in claim 11, their acid or base salts, organic or inorganic, their geometric isomers, their optical isomers, their solvates such as hydrates, and their mixtures, and at least one compound of formula (III) or (III') chosen from the compounds of formulae III-1, III-2, III-4, III-6, III-7, III-9, III-ll, III-12, III-14, III-15, III-16, III-17, III-18, III-19, III-20 or III-21, as defined according to claim 13, as well as their tautomers, one of their acid salts or basic, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures.

22. Composition according to the preceding claim, characterized in that it comprises at least one compound of formula (II) or (II') chosen from the group consisting of compounds of formula (II-1), (II-2), as defined in claim 11, their tautomers, their salts of acid or base, organic or mineral, their geometric isomers, their optical isomers, their solvates such as hydrates, and their mixtures, at least one compound of formula (III-20), its tautomer, one of its salts of acid or base, organic or mineral, its solvates, its optical isomers, its geometric isomers, and their mixtures.

23. Use of at least one compound of formula (II) or (II'), as defined according to claim 18, and / or one of their acid or base salts, organic or mineral, their solvates, such as their hydrates, their optical isomers, their geometric isomers and their mixtures, or of at least one composition C2 containing it or them, for the treatment of keratin materials, preferably keratin fibers, in particular human keratin fibers, such as hair.