EP4734948A1

EP4734948A1 - Process for treating keratin fibres employing at least one thiopyridinone compound

Info

Publication number: EP4734948A1
Application number: EP24737403.6A
Authority: EP
Inventors: Ozkan SARI; Andrew Greaves; Sylvie Genard
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2023-06-30
Filing date: 2024-06-26
Publication date: 2026-05-06
Also published as: FR3150432A1; WO2025003187A1; CN121398794A

Abstract

The present invention relates to a process for treating keratin fibres, in particular human keratin fibres, such as the hair, comprising bringing into contact with said keratin fibres at least one compound of formula (I) or (I'), as described hereinafter, and the optical isomers and geometrical isomers thereof, and also the organic or mineral acid or base salts thereof, and the solvates thereof such as the hydrates. The invention also relates to one or more compounds of formula (II) or (II'), as described hereinafter, and the optical isomers and geometrical isomers thereof, and also the organic or mineral acid or base salts thereof, and the solvates thereof such as the hydrates. The invention also relates to a process for treating keratin fibres, in particular human keratin fibres, such as the hair, comprising bringing into contact with said keratin fibres at least one compound of formula (III) or (III'), as described hereinafter, and the optical isomers and geometrical isomers thereof, and also the organic or mineral acid or base salts thereof, and the solvates thereof such as the hydrates.

Description

DESCRIPTION

TITLE: Process for treating keratin fibres employing at least one thiopyridinone compound

The present invention relates to a process for shaping keratin fibres, in particular human keratin fibres, such as the hair, comprising at least bringing into contact with said keratin fibres at least one compound of formula (I) or (P), as described hereinafter, and/or the optical isomers and geometrical isomers thereof, and also the organic or mineral acid or base salts thereof, and/or the solvates thereof such as the hydrates, or at least one composition Cl comprising same.

The invention also relates to one or more compounds of formula (II) or (If), as described hereinafter, and/or the optical isomers and geometrical isomers thereof, and also the organic or mineral acid or base salts thereof, and the solvates thereof such as the hydrates.

The invention also relates to a process for shaping keratin fibres, in particular human keratin fibres, such as the hair, comprising at least bringing into contact with said keratin fibres at least one compound of formula (III) or (IIP), as described hereinafter, and/or the optical isomers and geometrical isomers thereof, and also the organic or mineral acid or base salts thereof, and/or the solvates thereof such as the hydrates, or at least one composition comprising same.

Styling products are hair compositions usually used to build and structure the hairstyle and to give it hold. Such compositions generally comprise one or more film-forming polymers or "fixing polymers", enabling the formation of a coating film on the fibres so as to ensure hold of the hairstyle and/or the formation of micro-welds between the fibres, thus resulting in the fixing of the head of hair.

Such compositions are usually in the form of lotions, gels, foams or sprays and are commonly applied to wet hair, which is shaped before blow-drying or drying.

However, the shaping conferred by such styling products has the drawback of fading more or less rapidly over time and/or following one or more washes.

In other words, such styling products generally lead to a shape-retention of the fibres which is still too often unsatisfactory.

Such compositions may also lead to unsatisfactory shaping of the hair, in particular when they are applied to hair which has been sensitized, in particular by one or more chemical treatments, for example at least one relaxing, permanent waving, dyeing and/or bleaching process.

There is thus a real need to implement a process for cosmetic treatment of keratin fibres, in particular human keratin fibres, such as the hair, which does not have the drawbacks mentioned above, that is to say which is capable of shaping keratin fibres, including keratin fibres which have been sensitized by at least one chemical treatment, for example at least one relaxing, permanent waving, dyeing and/or bleaching process, and to do so in a long-lasting manner.

A subject of the present invention is therefore a process for shaping keratin fibres, in particular human keratin fibres, such as the hair, comprising at least the application to said keratin fibres of at least one compound of the following formula (I) and/or (T), and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or of at least one composition Cl comprising same:

(I) (I') in which formulae (I) and (T):

Ri denotes a radical selected from the group consisting of: a) a hydrogen atom, b) a saturated, linear Ci-Cio or branched C3-C10 alkyl group optionally substituted by one or more groups which may be identical or different and are selected from the group consisting of i) -O-R3 and ii) -S-R3;

R2 denotes a cyclic or acyclic radical selected from the group consisting of: a) a hydrogen atom, b) a saturated, linear C1-C12 or branched C3-C12 or cyclic C3-C8 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs 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 Ci-Cs alkoxy radicals;

R3 denotes a radical selected from a) a hydrogen atom, b) a saturated, linear C1-C10 or branched C3-C10 alkyl group;

R4 denotes a radical selected 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, in particular Ci, alkyl group, and preferably represents a hydrogen atom; it being understood that when R4 denotes e) an ammonium group, then the electroneutrality of the compounds of formula (I) or (P) is ensured by one or more cosmetically acceptable anions such as halides preferably selected from chloride or bromide.

The process according to the invention thus makes it possible to achieve the objectives as described above by using, on said fibres, 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 (P) as defined above), and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or a composition Cl comprising said compound(s) of formula (I) or (P) as defined above.

In other words, the process for treating keratin fibres according to the invention uses, on said fibres, at least one compound of formula (I), and/or at least one tautomer of a compound of formula (I), and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, 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 the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof. The process according to the invention makes it possible to improve the shaping of keratin fibres without the risk of damaging them, that is to say while preserving their cosmetic properties, for example in terms of feel, suppleness, softness, disentangling or sheen.

The process according to the invention makes it possible to improve the retention of the shape conferred upon the keratin fibres, in particular by conferring upon them long-lasting shaping that is able to be advantageously resistant, in particular to one or more shampoo washes.

The process according to the invention also has the advantage of modifying the shape of keratin fibres, in particular human keratin fibres such as the hair.

The process according to the invention in addition makes it possible to easily and efficiently shape keratin fibres, including sensitized keratin fibres, i.e. keratin fibres treated with at least one chemical treatment, in particular at least one process for permanent reshaping, for example relaxing or permanent waving, or a dyeing process and/or a bleaching process.

Within the meaning of the present invention, the term "sensitized keratin fibres" is understood to mean keratin fibres which have been chemically sensitized, i.e. treated by one or more chemical treatments, such as those described above.

In other words, said at least one compound responding to formula (I) and/or (T), and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or of at least one composition Cl comprising same, is preferably implemented in a process for shaping sensitized keratin fibres, i.e. keratin fibres that have been at least chemically sensitized by one or more chemical treatments such as permanent-waved, straightened, dyed and/or bleached keratin fibres, in particular bleached keratin fibres.

Hence, according to the present invention “sensitized keratin fibres” are distinctly different from keratin fibres that have been mechanically stressed.

Of course, the said at least one compound of formula (I), and/or (T), as defined above or the said at least one composition Cl, may be used for the cosmetic treatment of sensitized keratin fibres (in other words, chemically sensitized keratin fibres) that have also been mechanically stressed.

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 the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or of at least one composition Cl comprising said compound(s) of formula (I) or (P), for shaping keratin fibres, in particular human keratin fibres, such as the hair.

A subject of the invention is also a compound of formula (II) or (IP) of the following formula, and also one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:

(II) (II') in which formulae (II) and (IP):

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

- M denotes a radical selected 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 formula (I) or (P); preferably, Ri represents a hydrogen atom;

- R3 has the same meaning as in formula (I) or (P); preferably, R3 represents a hydrogen atom;

- X has the same meaning as in formula (I) or (P); preferably X represents an oxygen atom;

- R' has the same meaning as in formula (I) or (P); preferably, R' represents a hydrogen atom. The compound(s) of formula (II) or (If) is or are thiopyridinone compounds having the advantage of cosmetically treating keratin fibres, including sensitized keratin fibres, in particular of shaping them.

The compound(s) of formula (II) or (If) is or are thiopyridinone compounds which result in a better retention of the shape of the keratin fibres, including sensitized keratin fibres.

The compound(s) of formula (II) or (If) confer(s) in particular long-lasting shaping to keratin fibres, in particular human keratin fibres such as the hair.

In addition, a subject of the present invention is also a composition C2 comprising one or more compounds of formula (II) or (If), as defined above, and optionally at least one cosmetic additive.

The invention also relates to the use of one or more compounds of formula (II) or (If), as described above, or of at least one composition Cl or C2 comprising same, for treating keratin materials, in particular keratin fibres, in particular for shaping keratin fibres, preferably human keratin fibres such as the hair.

The invention additionally relates to a process for shaping keratin fibres, in particular human keratin fibres, such as the hair, comprising at least the application to said keratin fibres of at least one compound of the following formula (III) and/or (Ilf), and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or of at least one composition Cl or C3 containing same: in which formulae (III) and (Ilf):

- Ri has the same meaning as in formulae (I) and (I'),

- R2 denotes a radical selected from the group consisting of a) a hydrogen atom, b) a saturated, linear C1-C12 or branched C3-C12 or cyclic C3-C8 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected from i) -O-R3, ii)

-S-R3, in) -C(0)-0-R4, IV) a C5-C12 aryl group optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals; c) a C5-C12 aryl group optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals;

R4 denotes a radical selected from the group consisting of a) a hydrogen atom, b) a saturated, linear C1-C10 or branched C3-C10 alkyl group.

The compound(s) of formula (II) or (If) is or are thiopyridinone compounds which result in a better retention of the shape of the keratin fibres, including keratin fibres sensitized by at least one chemical treatment as described above.

The compound(s) of formula (II) or (If) result(s) in particular in long-lasting shaping of keratin fibres, in particular human keratin fibres such as the hair.

The invention is likewise directed to the use of one or more compounds of formula (III) or (IIP), as described above, or of at least one composition Cl or C3 containing same, for shaping keratin fibres, in particular human keratin fibres such as the hair.

Other subjects, characteristics, aspects and advantages of the invention will become even more clearly apparent on reading the description and the example that follows.

In the text hereinbelow, unless otherwise indicated, the limits of a range of values are included in that range, notably in the expressions "between" and "ranging from ... to ...".

Moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more".

In addition, the expression "at least" used in the present description is equivalent to the expression "greater than or equal to". Lastly, in a manner known per se, a "Cn" or "Cn" compound or group denotes a compound or a group containing, in its chemical structure, "n" carbon atoms.

Compound of formulae (I) and (P)

As indicated above, the thiopyridinone compound(s) is or are selected from the group consisting of the compounds of the following formula (I) or (P), and also one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:

(I) (I') in which formulae (I) and (I¹):

Ri denotes a radical selected from the group consisting of: a) a hydrogen atom, b) a saturated, linear C1-C10 or branched C3-C10 alkyl group optionally substituted by one or more groups which may be identical or different and are selected from the group consisting of i) -O-R3 and ii) -S-R3;

R2 denotes a cyclic or acyclic radical selected from the group consisting of: a) a hydrogen atom, b) a saturated, linear C1-C12 or branched C3-C12 or cyclic C3-C8 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected from i) -O-R3, ii) -S-R3, iii) -C(0)-0-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs 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 Ci-Cs alkoxy radicals;

X represents an oxygen atom, a sulfur atom, preferably an oxygen atom; R' represents a hydrogen atom or a C1-C4, in particular Ci, alkyl group, and preferably R' represents a hydrogen atom; it being understood that when R4 denotes e) an ammonium group, then the electroneutrality of the compounds of formula (I) or (P) is ensured by one or more cosmetically acceptable anions such as halides, preferably selected from chloride or bromide.

As indicated above, the compound of formula (P) is a tautomer of the compound of formula (I).

In other words, the thiopyridinone compound(s) is or are selected from the group consisting of the compounds of formula (I), as described above, the tautomers of formula (P), as described above, and also one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

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

According to another embodiment of the invention, Ri represents b) a saturated, linear C1-C10 or branched C3-C10 alkyl group optionally substituted by one or more groups which may be identical or different and are selected from the group consisting of i) -O-R3 and ii) -S-R3.

In accordance with this embodiment, Ri represents b) a saturated, linear C1-C10 or branched C3-C10 alkyl group, preferably a linear Ci-Ce alkyl group, such as methyl, ethyl, n-pentyl, n-hexyl, or a branched C3-C6 alkyl group, such as isopropyl, isobutyl, tert-butyl, more preferentially Ri represents an ethyl group.

Preferably, in formulae (I) and (P), Ri represents a) a hydrogen atom or a saturated, linear Ci-Ce or branched C3-C6 alkyl group.

More preferably, in formulae (I) and (P), Ri represents a) a hydrogen atom or a saturated C1-C4, in particular C1-C2, alkyl group.

More preferentially, in formulae (I) and (P), Ri represents a) a hydrogen atom.

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

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

Preferably, in formulae (I) and (P), R3 represents a) a hydrogen atom or b) a saturated, linear Ci-Ce or branched C3-C6 alkyl group.

More preferentially, in formulae (I) and (P), R3 represents a) a hydrogen atom. Preferably, in formulae (I) and (f), Ri represents a hydrogen atom and R3 represents a) a hydrogen atom or a saturated, linear Ci-Ce or branched C3-C6 alkyl group; more preferentially Ri and R3 represent a hydrogen atom.

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

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

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.

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

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

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.

Preferably, R4 represents a) a hydrogen atom, b) a linear Ci-Ce, in particular C1-C4, alkyl group or c) an alkali metal.

According to an advantageous embodiment, in formulae (I) and (P):

- Ri represents a) a hydrogen atom,

- R3 represents a) a hydrogen atom or b) a saturated, linear Ci-Ce or branched C3-C6 alkyl group; preferentially R3 represents a hydrogen atom,

- R4 represents a) a hydrogen atom, b) a linear Ci-Ce, in particular C1-C4, alkyl group or c) an alkali metal such as sodium or potassium, preferably a hydrogen atom or a linear Ci-Ce, in particular C1-C4, alkyl group.

Preferably, in formulae (I) and (!'), Ri and R3 represent a hydrogen atom, and R4 represents a) a hydrogen atom, b) a linear Ci-Ce, in particular C1-C4, alkyl group or c) an alkali metal such as sodium or potassium.

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

According to another embodiment, R2 denotes c) a C5-C12 aryl group optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals. According to another embodiment, R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 or cyclic C3-C8 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs 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)-.

According to another embodiment, R2 denotes b) a cyclic C3-C8 hydrocarbon group, optionally substituted, and preferably substituted, by one or more groups which may be identical or different and are selected 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 Ci-Cs 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)-.

According to another embodiment, R2 denotes b) a cyclic C3-C8 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs 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)-.

According to another embodiment, R2 denotes b) a cyclic C3-C8 hydrocarbon group, substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs alkoxy radicals.

According to another embodiment, R2 denotes b) a cyclic C3-C8 hydrocarbon group, substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs 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)-. According to another embodiment, R2 denotes b) a cyclic C3-C8 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 combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.

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

According to another embodiment, R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs 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)-.

Advantageously, in formulae (I) and (I'):

- Ri represents a) a hydrogen atom,

- R4 represents a) a hydrogen atom, b) a linear Ci-Ce, in particular C1-C4, alkyl group or c) an alkali metal such as sodium or potassium, preferably a hydrogen atom or a linear Ci-Ce, in particular C1-C4, alkyl group,

- R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs 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)-; with X and R' as defined above.

According to another embodiment, R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 hydrocarbon group, substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs 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)-.

According to another embodiment, R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs 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)-.

According to another embodiment, R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 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 combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or - N(R')-C(X)-.

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

According to another embodiment, R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs alkoxy radicals.

According to another embodiment, R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 or cyclic C3-C8 hydrocarbon group, preferably a saturated, linear Ci- C12 or branched C3-C12 hydrocarbon group, said hydrocarbon group being optionally substituted by one or more groups which may be identical or different and are selected from iii) -C(O)-O-R4, said group preferably 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 combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or - N(R')-C(X)-.

According to another embodiment, R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 hydrocarbon group, substituted by one or more groups iii) -C(O)-O- R4; said hydrocarbon group being additionally 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)-.

Advantageously, in formulae (I) and (I'):

- Ri represents a) a hydrogen atom,

- R? represents a) a hydrogen atom or b) a saturated, linear Ci-Ce or branched C3-C6 alkyl group; preferentially 3 represents a hydrogen atom,

- R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 hydrocarbon group, substituted by one or more groups iii) -C(O)-O-R4; said hydrocarbon group being additionally 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)-; with X and R' as defined above.

According to another embodiment, R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 hydrocarbon group, substituted by one or more groups iii) -C(O)-O- R4; said hydrocarbon group being additionally optionally substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs alkoxy radicals; said hydrocarbon group being additionally 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)-.

Preferably, in formulae (I) and (!'):

- Ri is as defined above; preferably Ri represents a hydrogen atom;

- R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 or cyclic C3-C8 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected 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.

More preferentially, in formulae (I) and (!'):

- Ri is as defined above; preferably Ri represents a hydrogen atom;

- R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 or cyclic C3-C8 hydrocarbon group, substituted by one or more identical or different iii) - C(0)-0-R4 groups; said hydrocarbon group being additionally optionally substituted by one or more groups which may be identical or different and are selected 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.

Compounds of formulae (II) and (ID

Preferably, the thiopyridinone compound(s) of formulae (I) and (!') is or are selected from the group consisting of the compounds of formula (II) or (If), and also one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:

(II) (If) in which formulae (II) and (If):

- R' has the same meaning as in formula (I) or (P); preferably, R' represents a hydrogen atom.

In other words, the thiopyridinone compound(s) of formulae (I) and (P) is or are selected from the group consisting of the compounds of formula (II), the tautomers of formula (IP), and also one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

According to one embodiment, in formulae (II) and (IP), Ri represents a hydrogen atom.

According to one embodiment, in formulae (II) and (IP), M represents c) an alkali metal or d) an alkaline earth metal; preferably M represents c) an alkali metal such as sodium or potassium.

According to another embodiment, in formulae (II) and (IP), M represents an ammonium group.

According to another embodiment, in formulae (II) and (IP), M represents a linear C1-C10 or branched C3-C10 alkyl group.

In accordance with this embodiment, in formulae (II) and (IP), M represents a saturated, linear C1-C10, in particular Ci-Ce, more particularly C1-C4, alkyl group, such as methyl or ethyl, or a saturated, branched C3-C10, in particular C3-C6, more particularly C3-C4, alkyl group.

In accordance with this embodiment, in formulae (II) and (IP), M represents a saturated, preferably linear, C1-C4 alkyl group, in particular methyl.

Preferably, in formulae (II) and (IP), M represents a hydrogen atom or an alkali metal.

As a variant, preferably, in formulae (II) and (IP), 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. Preferably, M represents a hydrogen atom, a saturated C1-C4 alkyl group, such as methyl or ethyl, or an alkali metal.

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

Preferably, in formulae (II) and (If), A represents a CH2-C(O)-N(R')-CH2- or -CH2-N(R')-C(X)-CH2- group with X and R' as defined above, preferably -CH2-C(O)- N(H)-CH₂-.

Preferentially, the compound(s) of formulae (II) and (If), the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, are such that:

- Ri has the same meaning as in formula (I) or (P); preferably, Ri represents a hydrogen atom,

- A represents a linear or branched, preferably linear, (C2-C6) alkylene group; said chain A being interrupted by a -C(X)-N(R')- group with X and R' as defined above and preferably representing -C(O)-N(H)-;

- M denotes a radical selected 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;

Preferentially, the compound(s) of formulae (II) and (IP), the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, are such that:

- Ri represents a hydrogen atom, - R' represents a hydrogen atom or a C1-C4, in particular Ci, alkyl group, and preferably R' represents a hydrogen atom;

- A represents a divalent, saturated or unsaturated, preferably saturated, hydrocarbon chain comprising from 1 to 8 carbon atoms, particularly A represents a linear or branched, preferably linear, (C2-C6) alkylene group; said chain A being interrupted by a -C(X)-N(R')- group with X and R' as defined above, preferably -C(O)-N(H)-; more particularly A represents a CH₂-C(O)-N(R')-CH₂- or -CH₂-N(R')-C(X)-CH₂- group with X and R' as defined above, preferably -CH₂-C(O)-N(H)-CH₂-;

- M being as defined above preferably represents a hydrogen atom, an alkali metal, or a linear or branched C1-C4 alkyl group such as methyl or ethyl, and more preferentially represents a hydrogen atom or an alkali metal such as sodium or potassium.

More preferentially, the compound(s) of formula (I) or (f) or (II) or (If) is or are selected from the group consisting of the compounds of formula (IIA) or (IIB) below and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:

(IIA) (IIB) in which formulae (IIA) and (IIB):

- R_a and Rb independently denote a hydrogen atom or a C1-C4 alkyl radical optionally substituted by one or more hydroxy (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 the compounds of formula (II) or (If); in particular, M represents a hydrogen atom, an alkali metal, or an alkyl, linear or branched, C1-C4 alkyl group such as methyl or ethyl, preferably a hydrogen atom or an alkali metal such as sodium or potassium. According to one embodiment, in formulae (IIA) and (IIB), the index n is equal to 1.

According to one embodiment, in formulae (IIA) and (IIB), the index m is equal to 1.

According to a particular embodiment, in formulae (IIA) and (IIB), n is equal to m.

According to one embodiment, in formulae (IIA) and (IIB), n and m are different.

According to one embodiment, in formulae (IIA) and (IIB), Ra denotes a hydrogen atom.

According to one embodiment, in formulae (IIA) and (IIB), Rb denotes a hydrogen atom.

According to a particular embodiment, in formulae (IIA) and (IIB), Ra and Rb are identical.

According to one embodiment, in formulae (IIA) and (IIB), R_a and Rb are different.

According to one embodiment, in formulae (IIA) and (IIB), Ra denotes a Ci- C4 alkyl radical substituted by one or more hydroxy (OH) or thiol (SH) radicals, preferably substituted by a radical selected from OH or SH.

According to one embodiment, in formulae (IIA) and (IIB), Ra denotes a C1-C4 alkyl radical which is substituted, more preferentially by an OH radical.

According to one embodiment, Rb denotes a C1-C4 alkyl radical substituted by one or more hydroxy (OH) or thiol (SH) radicals, preferably substituted by a radical selected from OH or SH, more preferentially by an OH radical.

According to one embodiment, in formulae (IIA) and (IIB), Rb denotes an unsubstituted C1-C4 alkyl radical such as methyl.

Preferably, in formulae (IIA) and (IIB):

- n and m are identical and equal to 1,

- Ra and Rb, which may be identical or different, denote a hydrogen atom or a linear or branched C1-C4 alkyl radical, optionally substituted by one or more hydroxy (OH) or thiol (SH) radicals, preferably substituted by a radical selected from OH or SH, more preferentially substituted by an OH radical;

- M represents a hydrogen atom, an alkali metal or a linear or branched C1-C4 alkyl group, preferably methyl or ethyl. According to a particularly preferred embodiment, the compounds of formula (I) or (!') or (II) or (If) or (IIA) or (IIB) are selected from the compounds of formulae (Ila) to (Hi) or (Il'a) to (Il'i) below, and also the tautomers thereof and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:

with M as defined above, in particular M represents a hydrogen atom, an alkali metal, or a linear or branched C1-C4 alkyl group such as methyl or ethyl, more preferentially a hydrogen atom or an alkali metal such as sodium or potassium.

According to a very particularly preferred embodiment, the compounds of formula (I) or (!') or (II) or (If) or (IIA) or (IIB) are selected from the compounds of formulae (Ila) or (Il'a) above and/or one of the organic or mineral acid or base salts 1 thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

Even more preferentially, the compounds of formula (I) or (P) or (II) or (IP) or (IIA) or (IIB) are selected from the compounds of formula (II), and more particularly from the compounds of formula (II- 1) or (IP 1) or (II-2) or (IP2), below and/or one of the organic or mineral acid or base salts thereof, in particular the sodium or potassium salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:

In accordance with the present invention, the compounds of formulae (II' 1) and (11'2) correspond to the tautomers of the compounds of formulae (II- 1 ) and (II-2).

Advantageously, the compound according to the invention is the compound of formula (II-2) or (11'2).

Compounds of formulae (III) and (III¹)

Preferably, the thiopyridinone compound(s) of formulae (I) and (I') is or are selected from the group consisting of the compounds of formula (III) or (IIP), and also one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:

(in) (nr) in which formulae (III) and (II ):

Ri is as defined above for the compounds of formula (I) or (P), R2 denotes a radical selected from the group consisting of: a) a hydrogen atom, b) a saturated, linear C1-C12 or branched C3-C12 or cyclic C3-C8 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs alkoxy radicals, and c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals, and

R3 denotes a radical selected from the group consisting of: a) a hydrogen atom, and b) a saturated, linear C1-C10 or branched C3-C10 alkyl group; and

R4 denotes a radical selected from a) a hydrogen atom, b) a saturated, linear C1-C10 or branched C3-C10 alkyl group.

According to one embodiment, in formulae (I) and (P) or (III) and (IIP), Ri represents:

- a hydrogen atom, or

- a linear C1-C10 alkyl group or a branched C3-C10 alkyl group, in particular a linear Ci-Ce alkyl group or a branched C3-C6 alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl; in particular said alkyl group of Ri is not substituted.

Preferably, in formulae (I) and (P) or (III) and (IIP), Ri represents a hydrogen atom. According to one embodiment, in formulae (I) and (P) or (III) and (IIP), R2 represents:

- a hydrogen atom;

- a linear C1-C10 alkyl group or a branched C3-C10 alkyl group, in particular a linear Ci-Ce alkyl group or a branched C3-C6 alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably a methyl or ethyl group; said alkyl group of R2 not being substituted.

In formulae (I) and (P) or (III) and (IIP), R2 can represent a linear C1-C10 alkyl group or a branched C3-C10 alkyl group, in particularly a linear Ci-Ce 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), even better substituted by a group iii) such as carboxy.

In formulae (I) and (P) or (III) and (IIP), 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 Ci-Cs alkoxy radicals, preferably a phenyl group that is in particular unsubstituted.

According to one embodiment, in formulae (I) and (P) or (III) and (IIP), R3 represents:

- a hydrogen atom,

- a saturated, linear C1-C10 or branched C3-C10 alkyl group; in particular a linear Ci-Ce alkyl group or a branched C3-C6 alkyl group, preferably a C1-C4 alkyl group such as a methyl group.

Preferably, in formulae (I) and (P) or (III) and (IIP), R3 represents a hydrogen atom.

According to one embodiment, in formulae (I) and (P) or (III) and (IIP), R4 represents:

- a hydrogen atom,

- a saturated, linear C1-C10 or branched C3-C10 alkyl group; in particular a linear Ci-Ce alkyl group or a branched C3-C6 alkyl group, preferably a Ci- C4 alkyl group such as a methyl or ethyl group. Preferably, in formulae (I) and (!') or (III) and (IIP), R4 represents a saturated, linear C1-C10 or branched C3-C10 alkyl group; in particular a linear Ci-Ce alkyl group or a branched C3-C6 alkyl group, preferably a C1-C4 alkyl group such as a methyl or ethyl group.

Preferably, in formulae (I) and (P) or (III) and (IIP),

- Ri represents a radical selected from: a) a hydrogen atom, and b) a saturated, linear Ci-Ce or branched C3-C6 alkyl group optionally substituted by one or more groups which may be identical or different and are selected from the group consisting of: i) -O-R3, and ii) -S-R3,

• preferably optionally substituted by one or more groups i);

- R2 represents a radical selected from: a) a hydrogen atom, and b) a saturated, linear C1-C10 or branched C3-C10 or cyclic C3-C8, such as Cs-Ce, hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected from the group consisting of: i) -O-R3, ii) -S-R3, iii) -C(O)-O-R3, and iv) a phenyl group optionally substituted by one or more hydroxyls and/or by one or more C1-C4 alkoxy radicals such as methoxy,

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

- R3 represents a radical selected from the group consisting of: a) a hydrogen atom, and b) a saturated, linear Ci-Ce or branched C3-C6 alkyl group,

- R4 represents a radical selected from the group consisting of: a) a hydrogen atom, and b) a saturated, linear Ci-Ce or branched C3-C6 alkyl group,

• preferably, R4 represents a saturated, linear Ci-Ce, in particular C1-C4, alkyl group. Preferentially, the compounds of formula (I) or (III), the tautomers of formula (P) or (IIP), the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, are such that:

- Ri represents a radical selected from: a) a hydrogen atom, and b) a saturated, linear C1-C4 or branched C3-C4 alkyl group optionally substituted by one or more groups which may be identical or different and are selected from i) -O-R3 and more preferably unsubstituted;

- R2 represents a radical selected from: a) a hydrogen atom, and b) a saturated, linear C1-C10 or branched C3-C10 or cyclic C3-C8, such as Cs-Ce, hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected from i) -O-R3, iii) -C(O)-O-R3, and iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and/or by one or more C1-C4 alkoxy radicals; and

- R3 represents a radical selected from: a) a hydrogen atom; b) a saturated, linear C1-C4 or branched C3-C4 alkyl group such as methyl or ethyl; and

- R4 represents a radical selected from: a) a hydrogen atom, and b) a saturated, linear Ci-Ce or branched C3-C6 alkyl group;

• preferably, R4 represents a saturated, linear Ci-Ce, in particular C1-C4, alkyl group.

Preferably, the thiopyridinone compound of formulae (I) and (P) or (III) and (IIP) is selected from the group consisting of the compounds III-l to III-24 below, the tautomers thereof, the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, in particular the compounds III-l, III-2, III-4, III-6, III-7, III-9, III-l 1, HI-12, III-14, HI-15, HI-16, III-17, III-18, HI-19, III-20 or HI-21, more particularly III-l, HI-9, III- 16, III- 18, III- 19, III-20 or HI-21, preferably III- 18, III- 19, III-20 or III-21, and more preferably III- 19 or III-20, even more preferably III-20:

Preferably, the thiopyridinone compound(s) of formula (I) or (P) is or are selected from the group consisting of the compounds of formula (II) or (If), the compounds of formula (III) or (IIP), and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

Preferably, the thiopyridinone compound(s) of formula (I) or (P) is or are selected from the group consisting of the compounds of formula (IIA) or (IIB), the compounds of formula (III) or (IIP), and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

Preferably, the thiopyridinone compound(s) of formula (I) or (P) is or are selected from the group consisting of the compounds of formulae (Ila) to (Hi) or (IPa) or (Il'i), the compounds of formula (III) or (IIP), and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

Preferably, the thiopyridinone compound(s) of formula (I) or (P) is or are selected from the group consisting of the compounds of formulae (Ila) to (Hi) or (Il'a) to (Il'i), in particular the compound of formula (Ila) or (Il'a), the compounds of formulae III-l to III-24, and/or one of the tautomers thereof, one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

More preferentially, the thiopyridinone compound(s) of formula (I) or (P) is or are selected from the group consisting of the compounds of formulae (Ila) to (Hi) or (Il'a) to (Il'i), in particular the compound of formula (Ila) or (Il'a), the compounds III- 1 , III-2, III-4, III-6, III-7, III-9, III-l l, HI-12, III-14, III-15, III-16, III-17, III-18, III-19, III-20 or III-21, and/or one of the tautomers thereof, one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

Even more preferentially, the thiopyridinone compound(s) of formula (I) or (P) is or are selected from the group consisting of the compounds of formulae II- 1, 112, the compounds III-l, III-2, III-4, III-6, III-7, III-9, III-l l, III-12, HI-14, HI-15, III-16, III- 17, III- 18, III- 19, III-20 or III-21, and/or one of the tautomers thereof, one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

Advantageously, the thiopyridinone compound(s) of formula (I) or (P) is or are selected from the group consisting of the compounds of formulae II- 1, 112, II' 1 or IP2 or compound III- 19 or compound III-20, and/or one of the tautomers thereof, one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

Even more advantageously, the thiopyridinone compound(s) of formula (I) or (P) is or are selected from the group consisting of the compounds of formula 112 or IP2 or compound III-20, and/or one of the tautomers thereof, one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

The acceptable solvates of the compounds of formula (I) or (P), of the compounds of formula (II) or (IP), of the compounds of formula (III) or (IIP) comprise conventional solvates such as those formed during the preparation of said compounds as a result of the presence of solvents.

Mention may be made, by way of example, of the solvates due to the presence of water or of linear or branched alcohols, such as ethanol or isopropanol.

The optical isomers are in particular enantiomers and diastereoisomers.

The geometrical isomers are in particular isomers having a Z/Z, Z/E, E/Z and EZE geometrical configuration.

Composition

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

The composition C2 according to the invention comprises at least one compound of formula (II) or (If), as described above, and/or one of the organic or mineral acid or base salts thereof, one of the solvates thereof, such as the hydrates, one of the optical isomers thereof, one of the geometrical isomers thereof, and mixtures thereof.

The composition C3 according to the invention comprises at least one compound of formula (III) or (IIP), as described above, and/or one of the organic or mineral acid or base salts thereof, one of the solvates thereof, such as the hydrates, one of the optical isomers thereof, one of the geometrical isomers thereof, and mixtures thereof.

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

The compound(s) of formula (I) or (P) is or are as described above.

The composition Cl according to the invention may comprise at least two distinct thiopyridinone compounds of formula (I) or (P) as described above.

Thus, the composition Cl according to the invention may comprise a single thiopyridinone compound of formula (I) or (P) or a combination of different thiopyridinone compounds of formula (I) or (P). According to a particular embodiment, the composition Cl according to the invention comprises at least two compounds of formula (I) or (!'), preferably two compounds of formula (I) or (P).

Preferably, the composition Cl according to the invention comprises at least one compound of formula (I) or (P) selected from the group consisting of the compounds of formula (II) or (IP), as described above, the compounds of formula (III) or (IIP), as described above, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

The compound(s) of formula (II) or (IP) and of formula (III) or (IIP) are as described above.

More preferably, the composition Cl according to the invention comprises at least one compound of formula (I) or (P) selected from the group consisting of the compounds of formula (IIA) or (IIB), in particular selected from the compounds (Ila) to (Hi) or (IPa) to (IPi) as defined above, the compounds of formula (III) or (IIP), and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

Preferentially, the composition Cl according to the invention comprises at least one compound of formula (I) or (P) selected from the group consisting of the compounds of formulae (Ila) to (Hi) or (IPa) to (IPi), in particular the compound of formula (Ila) or (IPa), the compounds of formulae III-l to III-24, and/or one of the tautomers thereof, one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

More preferentially, the composition Cl according to the invention comprises at least one compound of formula (I) or (P) selected from the group consisting of the compounds of formulae (Ila) to (Hi) or (IPa) to (IPi), in particular the compound of formula (Ila) or (IPa), 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 the tautomers thereof, one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

Even more preferentially, the composition Cl according to the invention comprises at least one compound of formula (I) or (P) selected from the group consisting of the compounds of formulae II-l, 112, II'l or 11'2, the compounds III- 1 , III- 2, III-4, HI-6, HI-7, III-9, III-l l, III-12, HI-14, HI-15, III-16, III-17, HI-18, HI-19, HI- 20 or III-21 , and/or one of the tautomers thereof, one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

Advantageously, the composition Cl according to the invention comprises at least one compound of formula (I) or (!) selected from the group consisting of the compounds of formulae II-l, 112, II'l, 11'2, compound III- 19, compound III-20, and/or one of the tautomers thereof, one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

As indicated above, a subject of the present invention in particular is a composition C2 comprising at least one compound of formula (II) or (If), as described above, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

Preferably, composition C2 comprises at least one compound of formula (II) or (If) selected from the group consisting of the compounds of formula (IIA) or (IIB), in particular selected from the group consisting of the compounds of formulae (Ila) to (Hi) or (Il'a) to (Il'i), as defined above, more particularly the compound of formula (Ila) or (Il'a), even more preferentially from the compounds of formulae II-l, 112, the tautomers thereof, and the salts, isomers and/or solvates thereof.

According to one embodiment, the composition Cl denotes a composition C2.

According to another embodiment, the composition Cl according to the invention comprises at least one compound of formula (III) or (IIP), as described above, preferably selected from the group consisting of the compounds of formulae III- 1 to III-24, more preferentially selected from the group consisting of the compounds of formulae HI-1, III-2, III-4, III-6, III-7, III-9, III-l l, III-12, HI-14, HI-15, HI-16, III- 17, III- 18, III- 19, HI-20 or HI-21, even more preferentially III-l, HI-9, III- 16, HI- 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 the tautomers thereof, one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof. In other words, according to one embodiment, the composition Cl denotes a composition C3.

In accordance with a preferred embodiment, the composition Cl or C2 according to the invention comprises at least one compound of formula (I) or (P) selected from the group consisting of the compounds of formula (II) or (If), as described above, the salts, isomers and/or solvates thereof, and optionally at least one compound of formula (I) or (P) selected from the group consisting of the compounds of formula (III) or (IIP), as described above, and the salts, isomers and/or solvates thereof.

In accordance with this preferred embodiment, the composition Cl or C2 according to the invention comprises several compounds of formula (I) or (P), at least one being selected from the compounds of formula (II) or (IP) and at least one being selected from the compounds of formula (III) or (IIP), and also the salts, isomers and/or solvates thereof.

In other words, in accordance with this preferred embodiment, the composition Cl or C2 according to the invention comprises:

- at least one compound of formula (I) or (P) selected from the group consisting of the compounds of formula (II) or (IP), in particular selected from the group consisting of compounds of formulae (Ila) to (Hi) or (IPa) to (IPi), in particular the compound of formula (Ila) or (IPa), the salts, isomers and/or solvates thereof, and

- at least one compound of formula (I) or (P) selected from the group consisting of the compounds of formula (III) or (IIP), in particular selected from the group consisting of compounds of formulae III- 1 to III-24, more preferentially selected from the group consisting of the compounds of formulae III-l, III-2, III-4, III-6, III-7, III-9, III-l l, HI-12, HI-14, HI-15, III- 16, III- 17, III- 18, III- 19, III-20 or HI-21, more preferentially selected from the group consisting of the compounds of formulae III- 19 and III-20 and also the tautomers thereof, and the salts, isomers and/or solvates thereof.

In other words, in accordance with this particular embodiment, the composition Cl or C2 according to the invention comprises at least one compound of formula (II) or (IP), and also the salts, isomers and/or solvates thereof, and at least one compound of formula (III) or (IIP), and also the salts, isomers and/or solvates thereof. Preferably, in accordance with this embodiment, the composition Cl or C2 according to the invention comprises at least one compound of formula (II) or (If), selected from the group consisting of the compounds of formulae (Ila) to (Hi) or (Il'a) to (Il'i), in particular the compound of formula (Ila) or (Il'a), and at least one compound of formula (III) or (IIP) selected from the group consisting of the compounds of formulae III- 1 to III-24, more preferentially selected from the group consisting of the compounds of formulae III-l, III-2, III-4, III-6, III-7, III-9, HI-11, HI-12, III-14, HI- 15, III-16, III-17, III-18, III-19, III-20 or III-21, even more preferentially selected from the group consisting of the compounds III- 19 and III-20 and also the tautomers thereof, and the salts, isomers and solvates thereof.

More preferentially, the composition Cl or C2 according to the invention comprises at least one compound of formula (II) or (IP), selected from the group consisting of the compounds of formulae (II-l) and (II-2) and also the tautomers thereof, the salts, isomers and/or solvates thereof, and at least one compound of formula (III) or (IIP) selected from the group consisting of the compounds of formulae HI-1, III-9, HI-16, III-18, III-19, HI-20 or III-21, preferably HI-18, III-19, HI-20 or HI- 21, and more preferably III- 19 or III-20, and also the salts, isomers and/or solvates thereof.

Advantageously, the composition Cl or C2 according to the invention comprises at least one compound of formula (II) or (IP) selected from the group consisting of the compounds of formulae (II- 1), (II-2), the organic or mineral acid or base salts thereof, the geometrical isomers thereof, the optical isomers thereof, the solvates thereof such as the hydrates, and mixtures thereof, and at least one compound of formula (III-20), the tautomer thereof, one of the organic or mineral acid or base salts thereof, the solvates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

The composition Cl or C2 or C3 according to the invention, as described above, may be aqueous, and preferably is aqueous.

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

The composition Cl or C2 or C3 may also comprise at least one organic solvent, preferably selected from the group consisting of C1-C4 alcohols, in particular ethanol. In other words, the composition Cl 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.

Composition Cl may be in any of the forms conventionally used in hair care, in particular in the form of lotions or thickened lotions.

Composition C2 may be in any of the forms conventionally intended for application to keratin materials such as the skin or keratin fibres. Thus, composition C2 may be in the form of lotions, thickened lotions, sprays, more or less fluid creams, gels or roll-ons. The compositions C2 may be direct or inverse emulsions.

In particular, composition C2 may be in any of the forms conventionally intended for caring for keratin materials, for example for caring for the skin and/or the hair.

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

Thus, the amount of the thiopyridinone compound(s) of formula (I) or (T) in the composition Cl or C2 or C3 according to the invention is preferably between 0.001% and 70% by weight, more preferentially between 0.003% and 60% by weight, even more preferentially between 0.005% and 50% by weight, even more preferentially between 0.01% and 40% by weight, relative to the total weight of the composition.

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

Preferably, the composition Cl or C3 according to the invention comprises at least 0.001% by weight of thiopyridinone compounds of formula (III) or (Ilf), as described above, preferably at least 0.05% by weight, more preferentially at least 0.1% by weight, relative to the total weight of the composition.

Use

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 the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or of at least one composition Cl comprising same, as defined above, for shaping keratin fibres, in particular human keratin fibres, such as the hair.

The compound(s) of formula (I) or (P), the compound(s) of formula (II), (If) and also the compound(s) of formula (III) and (IIP) used are as defined above.

The composition Cl or C2 or C3 used in accordance with the present invention is as defined above.

Preferably, the invention relates to the use of at least one compound of formula (I) or (P) selected from the group consisting of the compounds of formula (II) or (IP) as described above, preferably selected from the compounds of formula (IIA) or (IIB), the compounds of formula (III) or (IIP), as described above, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or of at least one composition comprising same, as defined above, for shaping keratin fibres, in particular human keratin fibres, such as the hair.

Preferably, the invention relates to the use of at least one compound of formula (II) or (IP) as described above, one of the organic or mineral acid or base salts thereof, one of the optical isomers or geometrical isomers thereof, the solvates thereof, such as the hydrates and/or mixtures thereof, or of at least one composition C2 comprising same, as defined above for treating keratin materials such as the skin or keratin fibres, preferably keratin fibres, in particular human keratin fibres such as the hair.

Preferably, the invention relates to the use of at least one compound of formula (II) or (IP) selected from the compounds of formula (IIA) or (IIB), in particular selected from the group consisting of the compounds of formulae (Ila) to (Hi) or (IPa) to (IPi), in particular the compounds of formula (Ila) or (IPa), more preferentially selected from the group consisting of the compounds of formulae (II-l), (II-2), the tautomers thereof, and the salts, isomers and/or solvates thereof, or of at least one composition comprising same, as defined above, for treating keratin materials such as the skin or keratin fibres, preferably keratin fibres, in particular human keratin fibres such as the hair.

More preferentially, the use of at least one compound of formula (II) or (IP) as described above or of at least one composition C2 comprising at least one compound of formula (II) or (IP) is a use for treating keratin fibres, in particular human keratin fibres such as the hair, and more particularly for shaping keratin fibres, in particular human keratin fibres such as the hair. Preferably, the invention relates to the use of at least one compound of formula (III) or (IIP) as described above, preferably selected from the group consisting of the compounds of formulae III-l to III-24, more preferentially selected from the group consisting of the compounds of formulae III- 1 , III-2, III-4, III-6, III-7, III-9, Hil l, HI-12, HI-14, III-15, HI-16, III-17, III-18, HI-19, III-20 or III-21, in particular selected from the group consisting of the compounds III-19 and III-20, even more particularly the compound III-20, and also the tautomers thereof, and the salts, isomers and/or solvates thereof, or of at least one composition comprising same, as defined above, for shaping keratin fibres, in particular human keratin fibres such as the hair.

Advantageously, the use according to the invention is a use for retention of the shaping of keratin fibres, in particular human keratin fibres such as the hair.

More advantageously, the use according to the invention is a use for modifying the shape of keratin fibres, in particular human keratin fibres such as the hair.

More preferentially, the keratin fibres are keratin fibres which have been sensitized, in particular by at least one chemical treatment such as a process for permanent reshaping, for example a relaxing or permanent waving, dyeing and/or bleaching process.

Even more preferentially, the keratin fibres are dyed and/or bleached, in particular bleached, keratin fibres.

Process for treating keratin fibres

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

The compound(s) of formula (I) or (I'), the compound(s) of formula (II), (If) and also the compound(s) of formulae (III) and (IIP), used in the process according to the invention, are as defined above.

The composition used in the process according to the invention is as defined above. The composition thus comprises at least one compound of formula (I) or (I'), as defined above. Preferably, the process according to the invention comprises at least the application to said fibres of at least one compound of formula (I) or (P) selected from the group consisting of the compounds of formula (II) or (If), as defined above, the compounds of formula (III) or (IIP), as defined above, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or of at least one composition comprising same.

A subject of the invention is in particular a process for treating keratin fibres, in particular for shaping keratin fibres, in particular human keratin fibres such as the hair, comprising at least the application to said fibres of at least one compound of formula (II) or (IP), as defined above, preferably selected from the compounds of formula (IIA) or (IIB), in particular selected from the group consisting of the compounds of formulae (Ila) to (Hi) or (IPa) to (IPi), in particular the compounds of formula (Ila) or (Il'a), more preferentially selected from the group consisting of the compounds of formulae (II-l), (II-2), the tautomers thereof, and the salts, isomers and/or solvates thereof, or of at least one composition comprising same, as defined above.

A subject of the invention is likewise a process for shaping keratin fibres, in particular human keratin fibres such as the hair, comprising at least the application to said fibres of at least one compound of formula (III) or (IIP), as defined above, preferably selected from the compounds of formulae III- 1 to III-24, more preferentially selected from the group consisting of the compounds of formulae III- 1 , III-2, III-4, III- 6, III-7, III-9, III-l l, HI-12, HI-14, III-15, III-16, HI-17, HI-18, III-19, III-20 or III-21, in particular selected from the group consisting of the compounds III- 19 or III-20, even more particularly the compound III-20, and also the tautomers thereof, and the salts, isomers and/or solvates thereof, or of at least one composition comprising same, as defined above.

Preferably, the process according to the invention is a process for shaping keratin fibres, in particular human keratin fibres such as the hair.

Advantageously, the process according to the invention is a process for modifying the shape of keratin fibres, in particular human keratin fibres such as the hair.

Preferably, the application or bringing into contact of at least one compound of formula (I) or (P), as described above, or of at least one composition as defined above, is carried out on dry or wet keratin fibres. More preferentially, the application or bringing into contact of at least one compound of formula (I) or (!'), as described above, or of at least one composition as defined above, is carried out on dry or wet hair.

Preferably, the step of bringing into contact or applying the compound(s) of formula (I) or (!') or the composition comprising same includes a leave-on time of between 10 seconds and 30 minutes, preferably between 30 seconds and 15 minutes.

Preferably, the step of bringing into contact or application is repeated.

Preferably, the keratin fibres are sensitized, i.e. keratin fibres that are treated by one or more chemical treatments as previously defined.

Preferably, the keratin fibres are sensitized, more preferentially by at least one process for permanent reshaping, for example a relaxing or permanent waving process, or at least one dyeing and/or bleaching, in particular bleaching, process.

More preferentially, the hair is sensitized hair.

Preferably, the process according to the instant invention comprises: a) at least the application to keratin fibres of at least one compound responding to formula (I) or (I’), as previously described, or of at least one composition Cl comprising same, b) at least shaping said keratin fibres.

According to the present invention, the at least shaping of the keratin fibres consists of modifying the shape of the keratin fibres.

The at least shaping of the keratin fibres may be a temporary shaping of the keratin fibres, carried out for example by using mechanical means such as curlers or by treating said keratin fibres with an iron.

The at least shaping of the keratin fibres may be a long-lasting shaping of the keratin fibres, for example a relaxing or permanent waving process.

The application of said compound of formula (I) and/or (T) or said composition Cl may be implemented sequentially, successively or at the same time as the at least shaping of said keratin fibres.

Preferably, the process comprises at least the application to keratin fibres of said at least one compound responding to formula (I) or (T), as previously described, or of at least one composition C 1 comprising same, and then at least shaping the keratin fibres.

According to this preferred embodiment, the keratin fibres are preferably sensitized. Preferably, the process according to the invention comprises at least one step of heating the keratin fibres.

Preferably, the process according to the invention comprises at least one step of heating the keratin fibres implemented after the application of at least one compound of formula (I) or (P) or of at least one composition comprising at least one compound of formula (I) or (!').

The process consists in particular of: i) bringing the keratin fibres into contact with at least one compound of formula (I) or (!'), as defined above, or a composition comprising same, ii) optionally leaving it on, preferably leaving it on for a leave-on time ranging from 10 seconds to 30 minutes, iii) optionally rinsing, preferably rinsing, iv) optionally performing a heating step, preferably performing a heating step for a duration possibly ranging from 2 minutes to 1 hour, preferably ranging from 5 minutes to 30 minutes, more preferentially ranging from 8 minutes to 20 minutes.

Steps i) to iii) can be repeated.

General synthetic process for the compounds of formula (II) or (If)

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

The compounds of formula (III) or (IIP) used to obtain the compounds of formula (II) are thus the compounds of formula (III) or (IIP) as defined above and such that:

- Ri is as defined for the compounds of formula (III) or (IIP) and

- R.2 denotes a radical b) a saturated, linear C1-C12 or branched C3-C12 or cyclic C3-C8, preferably acyclic, hydrocarbon group and said hydrocarbon group being substituted by a radical iii) -C(O)-O-H, and optionally substituted by one or more groups which may be identical or different and are selected from: i) -O-R3, ii) -S-R3, iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals and

- R3 denotes a radical selected from the group consisting of: a) a hydrogen atom, and b) a saturated, linear C1-C10 or branched C3-C10 alkyl group; and c) a thiol function- or alcohol function-protecting group.

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 G. M. 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.

The compounds of formula (IV) denote in particular amino acids H2N- B- COORs in which:

- B denotes a divalent cyclic or acyclic, preferably acyclic, linear or branched radical 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 combinations thereof 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 hydroxy or thiol groups optionally protected by protecting groups; and

- Rs denotes a carboxylic acid function-protecting group such as an ester function and in particular a C1-C4 alkyl ester such as an ethyl ester, and

- X represents an oxygen or 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.

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

When the compounds of formula (IV) contain one or more asymmetric carbons, each of them may be of the R or S configuration or in racemic form. When the compounds of formula (IV) denote amino acids, these are preferably of the L configuration.

The coupling between the carboxylic acid function of a compound of formula (III) and the amine function of a compound of formula (IV) is achieved with the aid of conventional activation or coupling reagents such as carbodiimides such as DCC (= dicyclohexylcarbodiimide) or water-soluble forms of carbodiimides such as EDC (= N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride), phosphonium salts such as BOP (= (benzotriazol- 1-yloxy) tris(dimethylamino)phosphonium hexafluorophosphate), PyBOP (=(benzotriazol- 1-yloxy )tripyrrolidinophosphonium hexafluorophosphate), PyBROP (= bromotripyrrolidinophosphonium hexafluorophosphate), PyCloP (= chlorotripyrrolidinophosphonium hexafluorophosphate), or else with the aid of reagents such as PyClU (= chloro- N,N,N',N'-bis(tetramethylene) formamidinium hexafluorophosphate), N- hydroxy succinimide, EEDQ (= l-ethoxycarbonyl-2-ethoxy-l,2-dihydroquinoline), CDI (= carbonyldiimidazole), or else choroformates such as ethyl chloroformate or isobutyl chloroformate. When the coupling is achieved using coupling reagents such as carbodiimides, additives such as HOBt (= 1 -hydroxybenzotriazole) or N- hydroxysuccinimide may be added during the reaction to limit the racemization.

Preferentially, the coupling is achieved with carbodiimides optionally supplemented with 1 -hydroxybenzotriazole.

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

When the compound (IV) bears a carboxylic acid function protected by a protecting group Rs, 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 G. M. Wuts, Wiley Interscience Publication, John Wiley & Sons Inc., 1991. The conditions for this optional deprotection step are determined by the nature of the protecting group Rs.

For example, if the carboxylic acid function of (IV) is in ester form (that is to say Rs 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. The invention is illustrated in more detail in the following non-limiting examples.

Example:

Example 1: Synthesis of the compound of formula (III-20)

Step 1: Synthesis of the compound ethyl 3-N-[(2-thioxo-l.,2-

Route 1 : via 2-mercaptonicotinic acid

In a round-bottomed flask, thionicotinic acid is introduced into acetonitrile, followed by carbonyldiimidazole (CDI). The resulting mixture is refluxed for one hour and is then left at ambient temperature.

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

After the overnight period, the reaction medium is evaporated. The residue is taken up in di chloromethane and washed twice with 2N HC1.

The organic phase is dried over anhydrous sodium sulfate and then evaporated and purified over silica, di chloromethane 97/methanol 3.

The fractions are evaporated. A light yellow powder is obtained.

Route 2: via 2-chloronicotinic acid

In a three-necked flask, 2-chloronicotinic acid (250.0 g, 1.587 mol) is introduced into ethyl acetate (500 ml) and then SOCI2 (210.0 g, 1.761 mol) is added dropwise to the mixture.

The combined mixture is refluxed until complete conversion. Once the reaction is complete, the mixture is cooled to ambient temperature and diluted with ethyl acetate (375 ml).

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

The combined mixture is stirred for a period ranging from 3 to 4 hours and then the ethyl acetate is removed under vacuum.

The aqueous solution thus obtained is then diluted with water (1250 ml) and then acidified with 3N HC1 (25 ml).

Sodium thiosulfate (1379 g, 5.555 mol) is then added and the combined mixture is then refluxed for 6 hours. After cooling to 10°C, the yellow solid is filtered off and washed with water (3 times 750 ml).

The crude product is then treated with carbon black in a 75/25 ethanol/water mixture. The carbon black is then filtered off hot and the ethanol is evaporated off. The combined mixture is cooled to ambient temperature, then the product is filtered off and dried under vacuum.

A light yellow powder is thus obtained.

The 1H NMR and mass spectra are in accordance with the structure.

Melting point: 151°C (capillary tube)

Step 2: Synthesis of the compound N-[(2-thioxo-l.,2-dihvdropyridin-3- obtained in step 1

(III-20)

Ethyl N-[(2-thioxo-l,2-dihydropyridin-3-yl)carbonyl]glycinate (48 g, 0.317 mol) and a 95% EtOH solution (48 ml) are introduced into a three-necked flask.

The resulting mixture is cooled to 10°C.

A solution of NaOH (16 g) in 144 ml of water is added dropwise to the mixture.

The organic solvent is evaporated off and the pH of the mixture is then adjusted to a value of 3-4. The mixture is then cooled to a temperature of between 0 and 10°C and is 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 in accordance with the structure.

Melting point: 241.0-241.8°C (capillary tube) Example 2: Synthesis of compounds 1 and 2

Compound 1

The (2-mercaptonicotinoyl)glycine obtained in example 1 (20.000 g, 1 eq, 94.242 mmol) and DMF (100 ml) are introduced into a 250 ml round-bottomed flask.

The mixture is stirred until a clear solution is obtained and carbonyldiimidazole (16.809 g, 1.1 eq, 103.67 mmol) is then added in portions.

The resulting suspension is stirred at a temperature of 20°C until there is no bubbling (typically for one hour).

Ethyl glycinate hydrochloride (14.470 g, 1.1 eq, 103.67 mmol) is then added and the combined mixture is then stirred for one hour at a temperature of 20°C.

The reaction medium is then added slowly to a 10% aqueous NaHCCh solution with stirring.

The suspension obtained is filtered through a frit to afford 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.

The spectroscopic analyses are in accordance with the structure shown.

Compound 2

Compound 1, as obtained above, (ethyl (2-mercaptonicotinoyl)glycylglycinate) (13.440 g, 1 eq, 45.202 mmol) and distilled water (70 ml) are introduced into a 250 ml round-bottomed flask.

With stirring, a 50% sodium hydroxide solution is added until a pH of around 12-13 is reached while maintaining 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. The suspension obtained is filtered through a frit and then the resulting solid is rinsed with distilled water.

The solid is dried at 50°C under vacuum to obtain compound 2 (2-mercaptonicotinoyl)glycylglycine in the form of a yellow powder.

Example 3: Shaping evaluation

Preparation of the compositions

Compositions A (outside the invention), B and C (according to the invention) were prepared from the ingredients indicated in the table below:

Preparation of the locks

Locks of Caucasian hair, damaged by two successive bleaching operations, weighing 2.7 g and 20 cm long (alkaline solubility of 19, type II), are washed with DOP shampoo, and then squeezed out between the fingers (two 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 1 g of composition per 1 g of hair). The hair is then massaged with the fingers using circular movements throughout each lock (five times), and the locks are then left for 5 minutes. The locks are then rinsed with tap water for 30 seconds and then wrung out.

These various steps are repeated for a total of 10 applications. After the tenth application, the locks are dried at 60°C (10 min/g of hair).

Shape retention evaluation method - test method

The locks are shampooed (DOP), wrung out, and pre-dried with a paper towel. The locks are then rolled up using a curler (0 = 2 cm) and then dried at a temperature of 60°C for 10 minutes. The curler is then removed and the locks are suspended vertically.

The length of the locks for each of the compositions A, B and C is measured initially (t = 0) and then after a period of 4 hours (t = 4 hours).

The increase in the length of the locks treated with composition B and composition C is much less significant than for the lock treated with comparative composition A. This indicates better shape retention for the locks treated with composition B and composition C.

Claims

1. Process for shaping keratin fibres, in particular human keratin fibres, such as the hair, comprising at least the application to said keratin fibres of at least one compound of the following formula (I) or (!'), and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or of at least one composition Cl comprising same:

(I) (I') in which formulae (I) and (!'):

R3 denotes a radical selected from a) a hydrogen atom, b) a saturated, linear C1-C10 or branched C3-C10 alkyl group; R4 denotes a radical selected from the group consisting of a) a hydrogen atom, b) a saturated, linear Ci-Cio 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, in particular Ci, alkyl group, and 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 selected from chloride or bromide.

2. Process 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 saturated, linear Ci-Ce or branched C3-C6 alkyl group, and 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 saturated linear Ci-Ce, in particular C1-C4, alkyl group, or c) an alkali metal.

5. Process according to any one of the preceding claims, characterized in that R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs 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 saturated, linear C1-C12 or branched C3-C12 hydrocarbon group, substituted by one or more groups iii) -C(O)-O-R4; said hydrocarbon group being additionally optionally substituted by one or more groups which may be identical or different and are selected 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 Ci-Cs alkoxy radicals; said hydrocarbon group being additionally 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 formulae (I) and (f) is or are selected from the group consisting of the compounds of formula (II) or (If), and also one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:

(II) (If) in which formulae (II) and (If):

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

- 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 linear or branched, preferably linear, (C2-Ce)alkylene group; said chain A being interrupted by a -C(X)-N(R')- group with X and R' as defined in Claim 7, more particularly interrupted by a -C(O)-N(H)- group; 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 -CH₂-C(O)-N(H)-CH₂- group.

9. Process according to any one of the preceding claims, characterized in that the compound(s) of formula (I) or (P), the compounds of formula (II) or (IP) is or are selected from the group consisting of the compounds of formula (IIA) or (IIB) below, the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:

(IIA) (IIB) in which formulae (IIA) and (IIB):

- Ra and Rb independently of one another denote a hydrogen atom or a C1-C4 alkyl radical optionally substituted by one or more hydroxy (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 (If); in particular, M represents a hydrogen atom, an alkali metal, or an alkyl, linear or branched, C1-C4 alkyl group 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 (!'), the compounds of formula (II) or (If), the compounds of formula (IIA) or (IIB) is or are selected from the compounds of formulae (Ila) to (Hi) or (IPa) to (IPi) below, and also the tautomers thereof, the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:

11. Process according to any one of the preceding claims, characterized in that the compounds of formula (I) or (!'), the compounds of formula (II) or (If), the compounds of formula (IIA) or (IIB) are selected from the compounds of formula (II- 1) or (II'l) or (II-2) or (11'2) below, and also the organic or mineral acid or base salts thereof, in particular the sodium or potassium salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:

12. Process according to any one of Claims 1 to 4, characterized in that the thiopyridinone compound(s) of formulae (I) and (P) is or are selected from the group consisting of the compounds of formula (III) or (IIP), and also one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:

(III) (IIP) in which formulae (III) and (IIP): - Ri is as defined in formula (I) or (P),

R2 denotes a radical selected from the group consisting of: a) a hydrogen atom, b) a saturated, linear C1-C12 or branched C3-C12 or cyclic C3-C8 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected from: i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, and iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals, and c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals, and - R3 denotes a radical selected from the group consisting of: a) a hydrogen atom, and b) a saturated, linear C1-C10 or branched C3-C10 alkyl group; and

13. Process according to any one of Claims 1 to 4 or 12, characterized in that the compound(s) of formula (I) or (P) or the compounds of formula (III) or (IIP) are selected from the group consisting of the compounds III-l to III-24 below, the tautomers thereof, the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:

in particular the compounds III-l, III-2, III-4, III-6, III-7, III-9, III-l 1, III-12, ni-14, III-l 5, III-16, HI-17, HI-18, III-19, III-20 or III-21, more particularly III-l, III-9, III- 16, III-l 8, 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.

14. Process according to any one of the preceding claims, characterized in that the keratin fibres are sensitized, preferably dyed and/or bleached, in particular bleached.

15. Process according to any one of the preceding claims, characterized in that it comprises at least shaping keratin fibres, preferably a temporary shaping of the keratin fibres, carried out by using mechanical means such as curlers or by treating said keratin fibres with an iron, or a long-lasting shaping of the keratin fibres.

16. Use of at least one compound of formula (I) or (!'), as defined according to any one of Claims 1 to 13, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or of at least one composition Cl containing same, for shaping keratin fibres, in particular human keratin fibres, such as the hair.

17. Use according to Claim 16, characterized in that the compound(s) of formula (I) or (P) is or are selected from the group consisting of the compounds of formula (II) or (If), as defined according to any one of Claims 7 to 11, the compounds of formula (III) or (IIP), as defined according to Claim 12 or 13, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

18. Use according to Claim 16 or 17, characterized in that the compound(s) of formula (I) or (P) is or are selected from the group consisting of the compounds of formula (III) or (IIP), as defined according to Claim 12 or 13, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

19. Compound of formula (II) or (IP), as defined according to any one of Claims 7 to 11, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

20. Composition C2 comprising at least one compound of formula (II) or (IP), as defined according to Claim 19, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

21. Composition according to Claim 20, characterized in that it additionally comprises at least one compound of formula (I) or (!') selected from the group consisting of the compounds of formula (III) or (Ilf), as defined according to Claim 12 or 13, and also the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

22. Composition according to Claim 21, characterized in that it comprises at least one compound of formula (I) or (f) selected from the compounds of formulae (II-l), (II-2), (II' 1), (11'2), as defined in Claim 11, the organic or mineral acid or base salts thereof, the geometrical isomers thereof, the optical isomers thereof, the solvates thereof such as the hydrates, and mixtures thereof, and at least one compound of formula (III) or (Ilf) selected from the compounds of formulae III-l, 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, ID-20 or III-21, as defined according to Claim 13, and also the tautomers thereof, one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

23. Composition according to the preceding claim, characterized in that it comprises at least one compound of formula (II) or (If) selected from the group consisting of the compounds of formulae (II-l), (II-2), as defined in Claim 11, the tautomers thereof, the organic or mineral acid or base salts thereof, the geometrical isomers thereof, the optical isomers thereof, the solvates thereof such as the hydrates, and mixtures thereof, at least one compound of formula (III-20), the tautomer thereof, one of the organic or mineral acid or base salts thereof, the solvates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

24. Use of at least one compound of formula (II) or (If), as defined according to Claim 19, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or of at least one composition C2 containing same, for treating keratin materials and preferably keratin fibres, in particular human keratin fibres, such as the hair.