Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2002-12-17
2004-05-04
Seaman, D. Margaret (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
06730789
ABSTRACT:
The invention relates to novel compositions for the oxidation dyeing of keratinous fibers, comprising at least one 3-aminopyrazolo[1,5-a]pyridine as oxidation base, to the dyeing method employing this composition, to novel 3-aminopyrazolo[1,5-a]pyridines, and to their use for the oxidation dyeing of keratinous fibers.
It is known to dye keratinous fibers and particularly human hair with dyeing compositions comprising oxidation dye precursors, in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols, and heterocyclic compounds such as diaminopyrazole derivatives, which are referred to generally as oxidation bases. The oxidation dye precursors or oxidation bases are colorless or virtually colorless compounds which, when combined with oxidizing products, are able to give rise to colored compounds and dyes by a process of oxidative condensation. A common feature of these compounds is possession of an amino group and a hydroxyl group or of two amino groups, this giving them their character as oxidation bases.
It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or coloration modifiers, the latter being selected in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols, and certain heterocyclic compounds.
The variety of molecules employed as oxidation bases and couplers makes it possible for a rich palette of colors to be obtained.
The “permanent” coloration obtained by means of these oxidation dyes is required, moreover, to meet a certain number of requirements. Hence it must have no toxicological drawbacks, it must allow shades of the desired intensity to be obtained, and it must exhibit good stability via a vis external agents (light, inclement weather, washing, perming, perspiration, and friction).
The dyes must also allow white hair to be covered and, finally, they must be as unselective as possible; in other words, they must allow the smallest possible differences in coloration to be produced over the entire length of a single keratinous fiber, which may in fact be sensitized (i.e., damaged) differently between its tip and its root.
It has already been proposed, particularly in the patents GB 1 026 978 and GB 1 153 196, to use pyridines such as 2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine, 2,3-diamino-6-methoxypyridine, 2-(&bgr;-methoxyethyl)amino-3-amino-6-methoxypyridine and 3,4-diaminopyridine, as oxidation bases for the oxidation dyeing of keratinous fibers.
The applicant has now just discovered, completely unexpectedly and surprisingly, a new class of 3-aminopyrazolo[1,5-a]pyridines, of formula (I) defined hereinbelow, some of which are novel per se, which may be suitable for use as oxidation bases but which, moreover, make it possible to obtain dyeing compositions which lead to colorations which are strong even at neutral pH and which exhibit good stability vis a vis external agents (light, inclement weather, washing, perming, perspiration, and friction).
It is these discoveries which form the basis for the present invention.
Accordingly, the invention first provides a composition for the oxidation dyeing of keratinous fibers, and especially human keratinous fibers such as hair, characterized in that it comprises, in a medium appropriate for dyeing, at least one 3-aminopyrazolo[1,5-a]pyridine of formula (I) below as oxidation base and/or one of its addition salts with an acid or with a base:
in which:
R
1
, R
2
, R
3
, R
4
and R
5
, which are identical or different, represent a hydrogen or halogen atom; an —NHSO
3
H radical; a hydroxyl radical; a (C
1
-C
4
)alkyl radical; a (C
1
-C
4
)alkoxy radical; a (C
1
-C
4
)alkylthio radical; mono(C
1
-C
4
)alkylamino; a di(C
1
-C
4
)alkylamino radical in which the two alkyl groups, in conjunction with the nitrogen atom to which they are bonded, may form a ring which may be interrupted by one or more nitrogen, oxygen or sulfur atoms; a heterocycle; a nitro radical; a phenyl radical; a carbonyl radical; a ((C
1
-C
4
)alkoxy)carbonyl radical; a carboxamido radical; a cyano radical; an amino radical; a sulfonyl radical; a —CO
2
H radical, an —SO
3
H radical; a —PO
3
H2 radical; a —PO
4
H
2
radical; or a group of formula (II) below:
in which R represents an oxygen or nitrogen atom, X represents an oxygen atom or an NH or NH(C
1
-C
4
)alkyl group, and Y represents a hydroxyl, amino, C
1
-C
4
alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylamino or di(C
1
-C
4
)alkylamino radical.
In the compounds of formula (I) above, the alkyl term used for the alkyl radicals and for the groups containing an alkyl moiety signifies a linear or branched carbon chain containing 1 to 4 carbon atoms which is unsubstituted or substituted by one or more heterocycles or by one or more phenyl groups or by one or more groups selected from halogen atoms such as chlorine, bromine, iodine and fluorine; hydroxyl, alkoxy, amino, carbonyl, carboxamido, sulfonyl, —CO
2
H, —SO
3
H, —PO
3
H
2
, —PO
4
H
2
, —NHSO
3
H, sulfonamide, monoalkyl (C
1
-C
4
)amino or trialkyl(C
1
-C
4
)ammonium radicals or else by a dialkyl(C
1
-C
4
)amino radical in which the two alkyl groups, in conjunction with the nitrogen atom of said dialkyl(C
1
-C
4
)amino group to which they are bonded, may form a ring which may be interrupted by one or more nitrogen, oxygen or sulfur atoms.
Similarly, as claimed in the invention, the alkoxy term used for the alkoxy radicals and for the groups containing an alkoxy moiety signifies a linear or branched O-carbon chain containing 1 to 4 of carbon, which is unsubstituted or substituted by one or more groups selected from heterocycles; halogen atoms such as chlorine, bromine, iodine and fluorine; hydroxyl, amino, carbonyl, carboxamido, sulfonyl, —CO
2
H, —SO
3
H, —PO
3
H
2
, —PO
4
H
2
, —NHSO
3
H, sulfonamide, monoalkyl(C
1
-C
4
)amino or trialkyl(C
1
-C
4
)ammonium radicals or else by a dialkyl(C
1
-C
4
)amino radical in which the two alkyl groups, in conjunction with the nitrogen atom of said dialkyl(C
1
-C
4
)amino group to which they are bonded, may form a ring which may be interrupted by one or more nitrogen, oxygen or sulfur atoms.
As claimed in the invention, a heterocycle is an aromatic or nonaromatic ring containing 5, 6 or 7 members and from 1 to 3 heteroatoms selected from nitrogen, sulfur and oxygen atoms. These heterocycles can be condensed with other heterocycles or with a phenyl group. They can be substituted by a halogen atom; a (C
1
-C
4
)alkyl radical; a (C
1
-C
4
)alkoxy radical; a hydroxyl radical; an amino radical; a (C
1
-C
4
)alkylamino radical; di(C
1
-C
4
)alkylamino in which the two alkyl groups, in conjunction with the nitrogen atom to which they are bonded, may form a ring which may be interrupted by one or more nitrogen, oxygen or sulfur atoms. These heterocycles may additionally be quaternized by a (C
1
-C
4
)alkyl radical.
Among these heterocycles, mention may be made in particular, by way of example, of the following rings: thiadiazole, triazole, isoxazole, oxazole, azaphosphole, thiazole, isothiazole, imidazole, pyrazole, triazine, thiazine, pyrazine, pyridazine, pyrimidine, pyridine, diazepin, oxazepin, benzotriazole, benzoxazole, benzimidazole, benzothiazole, morpholine, piperidine, piperazine, azetidine, pyrrolidine, aziridine, 3-(2-hydroxyethyl)benzothiazol-3-ium and 1-(2-hydroxyethyl)pyridinium.
As claimed in the invention, phenyl means a phenyl radical which is unsubstituted or substituted by one or more cyano, carbonyl, carboxamido, sulfonyl, —CO
2
H, —SO
3
H, —PO
3
H
2
, —PO
4
H
2
, hydroxyl, amino, monoalkyl(C
1
-C
4
)amino or dialkyl(C
1
-C
4
)amino radicals in which the two alkyl groups, in conjunction with the nitrogen atom of said dialkyl(C
1
-C
4
)amino group to which they are bonded, may form a ring which may be interrupted by one or more nitrogen, oxygen or sulfur atoms.
Among the groups of formula (II) above, mention may be made in particular of the groups acetamide, dimethylurea, O-methylcarbamate, methylcarbonate, N-dimethylcarbamate and the esters.
Amon
Birault Veronique
Leduc Madeleine
Terranova Eric
L'Oreal (S.A.)
Seaman D. Margaret
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