Use for dyeing keratin fibres of a compound of azomethine type bearing two pyrazolopyridine units

Patent metadata

Field	Value
Publication number	US-10240043-B2
Application number	US-201515536747-A
Country	US
Kind code	B2
Filing date	Dec 17, 2015
Priority date	Dec 19, 2014
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

The invention relates to a compound chosen from the compounds of formulae (I) and (II), the leucoforms thereof, the optical and geometrical isomers thereof and the tautomers thereof, and also the addition salts thereof with an acid or a base, and the solvates thereof. The invention also relates to the use of these particular compounds for dyeing keratin fibres.

First claim

The invention claimed is:

1. A compound chosen from dyes of azomethine type comprising two pyrazolopyridine units, chosen from compounds of formulae (I) or (II) and leuco forms thereof, optical or geometrical isomers thereof, tautomers thereof, addition salts thereof with an acid or a base, and solvates or hydrates thereof:

wherein in formulae (I) and (II):
Z 1 represents an oxygen atom or a group —N(R 6 )—;
Z′ 1 represents an oxygen atom or a group —N(R′ 6 )—;
with the proviso that when Z 1 represents —N(R 6 )— and/or Z′ 1 represents —N(R′ 6 )—, then R 1 and R 6 and/or R′ 1 and R′ 6 , respectively, may form, together with the nitrogen atom to which they are attached, an optionally substituted, 5- to 8-membered, optionally cationic, saturated, unsaturated or aromatic heterocycle;

R 1 , R′ 1 , R 6 , and R′ 6 each independently represent:
a hydrogen atom,
a C 1 -C 10 alkyl radical optionally interrupted with one or more non-adjacent heteroatoms and/or optionally substituted, optionally with one or more groups chosen from i) hydroxyl, ii) optionally substituted, 5- to 8-membered, cationic or non-cationic, saturated, unsaturated or aromatic (hetero)cycle, iii) —N(R′)R″, and iv) —N + R′R″R′″, with R′, R′ and R′″ each independently representing a C 1 -C 6 alkyl group; or
an optionally substituted, 5- to 8-membered, cationic or non-cationic, saturated, unsaturated or aromatic (hetero)cyclic radical;

R 2 , R 3 , R 4 , R 5 , R′ 2 , R′ 3 , R′ 4 and R′ 5 each independently represent:
a hydrogen atom,
an optionally substituted C 1 -C 4 alkyl radical, or
a group chosen from —NH 2 , —N(H)R 10 , —N(R 11 )R 12 , OH or —OR 9 , with R 9 and R 10 representing an optionally substituted, linear or branched C 1 -C 6 alkyl, R 11 and R 12 , which may be identical or different, representing an optionally substituted, linear or branched C 1 -C 6 alkyl, or R 11 and R 12 forming, together with the nitrogen atom to which they are attached, a saturated, unsaturated or aromatic 5- to 8-membered heterocycle optionally containing one or more other heteroatoms or groups chosen from N, O, S, S(O) 2 and C(O), the heterocycle being optionally substituted; or

R 2 , R 3 , R 4 , R 5 , R′ 2 , R′ 3 , R′ 4 and R′ 5 may form, in pairs with adjacent radicals, an optionally substituted, saturated or unsaturated (hetero)cycle;
it being understood that when the compound of formula (I) or (II) is positively charged, then it comprises as many anionic counterions as cationic charges to achieve the electrical neutrality of the molecule.

2. The compound according to claim 1 , wherein R 1 and R′ 1 are chosen from: i) C 1 -C 6 alkyl; ii) C 1 -C 10 alkyl substituted with one or more hydroxyl groups; iii) C 1 -C 6 alkyl substituted with one or more amino or (di)(C 1 -C 4 )alkylamino groups; iv) C 1 -C 6 alkyl substituted with a nitrogenous heterocycle; or v) —[(CH 2 ) m —O] p -L-Y, with p =1, 2 or 3, m =1, 2 or 3, L denoting a linear or branched, saturated C 1 -C 6 divalent hydrocarbon-based group, and Y denoting a hydroxyl group or a hydrogen atom.

3. The compound according to claim 1 , wherein R 2 , R′ 2 , R 3 , R′ 3 , R 4 , R′ 4 , R 5 and R′ 5 independently represent a hydrogen atom or a C 1 -C 4 alkyl radical, or R 4 and R 5 and R′ 4 and R′ 5 together form a 5- to 8-membered ring.

4. The compound according to claim 1 , chosen from those of formula (I′) or (II′):

wherein in formulae (I′) and (II′):
Z″ 1 is chosen from an oxygen atom and a group —N(R″ 6 )—; and when Z″ 1 represents —N(R″ 6 )—, then R″ 1 and R″ 6 may form, together with the nitrogen atom to which they are attached, an optionally substituted, 5- or 6-membered, saturated, unsaturated or aromatic heterocycle;
R″ 1 represents a C 1 -C 6 alkyl radical, optionally interrupted with one or more non-adjacent oxygen atoms, and/or optionally substituted with:
a hydroxyl radical,
a di(C 1 -C 4 )alkylamino radical, or
a heterocycle optionally substituted with one or more C 1 -C 4 alkyl and/or hydroxyl radicals and chosen from pyrrolidine, piperidine, morpholine, piperazine and imidazole;

R″ 6 represents:
a hydrogen atom; or
a C 1 -C 10 alkyl radical optionally substituted with a hydroxyl radical;

R″ 2 , R″ 3 , R″ 4 and R″ 5 each independently represent:
a hydrogen atom; or
a C 1 -C 4 alkyl radical;

and the leuco forms thereof, isomers or tautomers thereof, and also the addition salts thereof with an acid or a base and the solvates or hydrates thereof.

5. The compound according to claim 4 , wherein Z″ 1 represents an oxygen atom; and R″ 1 denotes a linear or branched C 1 -C 6 alkyl radical, a C 1 -C 6 hydroxyalkyl radical, a di(C 1 -C 4 alkyl)amino(C 1 -C 6 alkyl) radical, a radical —[(CH 2 ) m′ —O] p′ -L′-Y′ with p′=1, 2, or 3, m′=2 or 3, L′ denoting a saturated linear C 1 -C 6 divalent hydrocarbon-based radical, and Y′ denoting a hydroxyl radical or a hydrogen atom, or an alkyl radical substituted with a heterocycle chosen from pyrrolidinyl, piperidyl, morpholinyl, piperazinyl and imidazolyl, said heterocycle being optionally substituted with one or more C 1 -C 4 alkyl radicals.

6. The compound according to claim 4 , wherein Z″ 1 represents NH; R″ 1 denotes a C 1 -C 6 hydroxyalkyl radical, a di(C 1 -C 4 alkyl)amino(C 1 -C 6 alkyl) radical, or an alkyl radical substituted with a heterocycle chosen from pyrrolidinyl, piperidyl, morpholinyl, piperazinyl and imidazolyl, said heterocycle being optionally substituted with one or more C 1 -C 4 alkyl radicals or hydroxyl.

7. The compound according to claim 4 , wherein Z″ 1 represents —N(R″ 6 )—; and R″ 1 and R″ 6 each independently denote a C 1 -C 6 alkyl radical or a C 1 -C 6 hydroxyalkyl radical; or R″ 1 forms with R″ 6 a ring, this ring being chosen from pyrrolidinyl, piperidyl, morpholinyl and piperazinyl rings optionally substituted with one or more C 1 -C 4 alkyl and/or hydroxyl radicals.

8. A composition for dyeing keratin fibers comprising, in a medium that is suitable for dyeing keratin fibers, at least one compound according to claim 1 .

9. The composition according to claim 8 , wherein the compound is present in an amount ranging from 0.01% to 15% by weight, relative to the total weight of the composition.

10. The composition according to claim 8 , further comprising one or more oxidizing agents.

11. A process for dyeing keratin fibers, comprising applying a dye composition according to claim 8 to the fibers.

12. A process for preparing compounds of formulae (I) and according to claim 1 , where formulae (I) and (II) are symmetrical:

comprising:
a) in a first stage, reacting at least two molar equivalents of pyrazolo[1,5-a]pyridine compound A 1 comprising an amino group in position 3 with a pyridine compound A 2 which is free in position 6 and comprising in position 2 either a hydrogen atom or an electrofugal group,
optionally performed i) in a polar protic solvent chosen from water or a mixture of water/C 1 -C 10 alcohol, ii) and/or in the presence of one or more mineral or organic basifying agents, iii) and/or in the presence of a chemical oxidizing agent, iv) and/or at a temperature ranging from 25° C. to the reflux temperature of the solvent; and

b) in a second stage, maintaining the reaction medium under stirring for a time ranging from 5 minutes to 48 hours;
c) wherein the re

Assignees

• Oreal

Inventors

• Fadli Aziz
• Blais Stephane

Classifications

• A61Q5/065

  Preparations for temporary colouring the hair, e.g. direct dyes · CPC title

• C09B55/006 Primary

  containing at least one heteroring · CPC title

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• A61K8/494

  with more than one nitrogen as the only hetero atom · CPC title

• C09B69/107

  containing an azomethine dye · CPC title