Patent ID: 6579326
Filing Date: 2003-06-17
Classification: A61K,A61Q,C07D

Abstract:
A composition for dyeing keratin fibres, wherein the composition comprises, in a medium which is suitable for dyeing:(i) at least one oxidation base; and (ii) at least one coupler chosen from indolizine derivatives of formula (I) and the acid addition salts thereof: in which:n may be an integer from 0 to 4; R1 and R3, which may be identical or different, are each chosen from hydrogen atoms; halogen atoms; Z groups; C1-C4 alkyl radicals; C1-C4 alkoxy radicals; C1-C4 monohydroxyalkyl radicals; C2-C4 polyhydroxyalkyl radicals; C1-C4 aminoalkyl radicals; acetylamino radicals; acetylamino-(C1-C4)alkyl radicals; (C1-C4)alkoxy(C1-C4)alkyl radicals; mono(C1-C4)alkylamino(C1-C4)alkyl radicals; di(C1-C4)alkylamino(C1-C4)alkyl radicals; aminocarboxy(C1-C4)alkyl radicals; acetyl(C1-C4)alkylamino(C1-C4)alkyl radicals; and aromatic rings which are optionally substituted with at least one radical chosen from halogen atoms, C1-C4 alkyl radicals, trifluoro-methyl radicals, C1-C4 alkoxy radicals, amino radicals, mono- and disubstituted amino radicals wherein the substituent is chosen from C1-C4 alkyl radicals, (C1-C4)alkylamino(C1-C4)alkyl radicals, di(C1-C4)alkylamino(C1-C4)alkyl radicals, carboxyl radicals and sulphoxy radicals; R3 may optionally further be chosen from 5- and 6-membered unsaturated heterocycles; R2 and R4, which may be identical or different, are each chosen from hydrogen atoms; halogen atoms, Z groups; C1-C4 alkyl radicals, C1-C4 monohydroxyalkyl radicals, C2-C4 polyhydroxyalkyl radicals, C1-C4 aminoalkyl radicals, mono(C1-C4)-alkylamino(C1-C4)alkyl radicals, di(C1-C4)alkyl-amino(C1-C4)alkyl radicals, carboxyl radicals, cyano radicals, carboxy(C1-C4)alkyl radicals, nitro radicals and 5- and 6-membered aromatic rings which are optionally substituted with at least one radical chosen from halogen atoms, C1-C4 alkyl radicals, trifluoromethyl radicals, C1-C4 alkoxy radicals, amino radicals and mono- and disubstituted amino radicals wherein the substituent is chosen from C1-C4 alkyl radicals, (C1-C4)alkylamino-(C1-C4)alkyl radicals, di(C1-C4)alkylamino-(C1-C4)alkyl radicals, carboxyl radicals and sulphoxy radicals; Z is chosen from the following unsaturated cationic groups of formulae (II) and (III) below, and the saturated cationic groups of formula (IV) below: in which:D is a linker arm which is chosen from linear and branched alkylene chains which may be interrupted by at least one hetero atom, and which may be substituted with at least one substituent chosen from hydroxyl and C1-C6 alkoxy radicals, and which may bear at least one ketone function; the ring members E, G, J, L and M, which may be identical or different, are chosen from carbon, oxygen, sulphur and nitrogen atoms; b is an integer from 0 to 4; m is an integer from 0 to 5; the radicals R, which may be identical or different, are chosen from a second group Z, which may be identical to or different from the first group Z, halogen atoms, hydroxyl radicals, C1-C6 alkyl radicals, C1-C6 monohydroxyalkyl radicals, C2-C6 polyhydroxyalkyl radicals, nitro radicals, cyano radicals, cyano(C1-C6)alkyl radicals, C1-C6 alkoxy radicals, tri(C1-C6)alkylsilane(C1-C6)alkyl radicals, amido radicals, aldehydo radicals, carboxyl radicals, (C1-C6)alkylcarbonyl radicals, thio radicals, C1-C6 thioalkyl radicals, C1-C6 alkylthio radicals, amino radicals, amino radicals protected with at least one group chosen from (C1-C6)alkylcarbonyls, carbamyls and C1-C6 alkylsulphonyl radicals; NHRâ€³ and NRâ€³Râ€²â€³ groups in which Râ€³ and Râ€²â€³, which may be identical or different, are chosen from C1-C6 alkyl radicals, C1-C6 monohydroxyalkyl radicals and C2-C6 polyhydroxyalkyl radicals; R5 is chosen from C1-C6 alkyl radicals, C1-C6 mono-hydroxyalkyl radicals, C2-C6 polyhydroxyalkyl radicals, cyano(C1-C6)alkyl radicals, tri(C1-C6)-alkylsilane(C1-C6)alkyl radicals, (C1-C6)alkoxy-(C1-C6)alkyl radicals, carbamyl(C1-C6)alkyl radicals, (C1-C6)alkylcarboxy(C1-C6)alkyl radicals, benzyl radicals and second Z groups which may be identical to or different from the first Z groups; R6, R7 and R8, which may be identical or different, are each chosen from C1-C6 alkyl radicals, C1-C6 monohydroxyalkyl radicals, C2-C6 polyhydroxyalkyl radicals, (C1-C6)alkoxy(C1-C6)alkyl radicals, cyano(C1-C6)alkyl radicals, aryl radicals, benzyl radicals, amido(C1-C6)alkyl radicals, tri(C1-C6)alkylsilane(C1-C6)alkyl radicals and C1-C6 aminoalkyl radicals in which the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyls, carbamyls and C1-C6 alkylsulphonyl radicals; two of the radicals R6, R7 and R8, may also form, together with the nitrogen atom to which they are attached, 5- and 6-membered saturated carbon-based rings and rings containing at least one hetero atom, it being possible for the said ring to be optionally substituted with at least one substituent chosen from halogen atoms, hydroxyl radicals, C1-C6 alkyl radicals, C1-C6 monohydroxyalkyl radicals, C2-C6 polyhydroxyalkyl radicals, nitro radicals, cyano radicals, cyano(C1-C6)alkyl radicals, C1-C6 alkoxy radicals, tri(C1-C6)alkylsilane(C1-C6)alkyl radicals, amido radicals, aldehydo radicals, carboxyl radicals, keto(C1-C6)alkyl radicals, thio radicals, C1-C6 thioalkyl radicals, C1-C6 alkylthio radicals, amino radicals and amino radical protected with at least one group chosen from (C1-C6)alkylcarbonyls, carbamyls and C1-C6 alkylsulphonyl radicals; one of the radicals R6, R7 and R8 may optionally be chosen from second Z groups, which may be identical to or different from the first Z groups;R9 is chosen from C1-C6 alkyl radicals; C1-C6 monohydroxyalkyl radicals; C2-C6 polyhydroxyalkyl radicals; aryl radicals; benzyl radicals; C1-C6 aminoalkyl radicals, C1-C6 aminoalkyl radicals wherein the amine is protected by at least one group chosen from (C1-C6)alkylcarbonyls, carbamyls and C1-C6 alkylsulphonyl radicals; carboxy(C1-C6)alkyl radicals; cyano(C1-C6)alkyl radicals; carbamyl(C1-C6)alkyl radicals; C1-C6 trifluoroalkyl radicals; tri(C1-C6)alkylsilane(C1-C6)alkyl radicals; sulphonamido(C1-C6)alkyl radicals; (C1-C6)alkylcarboxy(C1-C6)alkyl radicals; (C1-C6)alkylsulphinyl(C1-C6)alkyl radicals; (C1-C6)alkylsulphonyl(C1-C6)alkyl radicals; (C1-C6)alkylketo(C1-C6)alkyl radicals; N-(C1-C6)alkylcarbamyl(C1-C6)alkyl radicals; and N-(C1-C6)alkylsulphonamido(C1-C6)alkyl radicals; a and y are integers equal to 0 or 1; with the following provisos: in the unsaturated cationic groups of formula (II): when a=0, the linker arm D is attached to the nitrogen atom, when a=1, the linker arm D is attached to one of the ring members E, G, J and L, y cannot take the value 1 except: 1) when the ring members E, G, J and L simultaneously represent a carbon atom, and when the radical R5 is attached to the nitrogen atom of the unsaturated ring; or alternatively 2) when at least one of the ring members E, G, J and L represents a nitrogen atom to which the radical R5 is attached; when b is at least 2, two adjacent radicals R may also form together a ring chosen from unsaturated 5- and 6-membered carbon-based rings and rings containing at least one hetero atom; in the unsaturated cationic groups of formula (III): when a=0, the linker arm D is attached to the nitrogen atom, when a=1, the linker arm D is attached to one of the ring members E, G, J, L and M, y cannot take the value 1 except when at least one of the ring members E, G, J, L and M represents a divalent atom, and when the radical R5 is attached to the nitrogen atom of the unsaturated ring; when m is at least 2, two adjacent radicals R may also form together unsaturated 5- and 6-membered carbon-based rings and rings containing at least one hetero atom; in the cationic groups of formula (IV): when a=0, the linker arm D is attached to the nitrogen atom bearing the radicals R6 to R8, when a=1, two of the radicals R6 to R8 form, together with the nitrogen atom to which they are attached, saturated 5- and 6-membered rings as defined above, and the linker arm D is attached to a carbon atom of the said saturated ring; Xâˆ’ is chosen from monovalent and divalent anions; it being understood that: at least one of the radicals R1 and R3 represents a hydrogen atom; and wherein at least one of R1, R2, R3 or R4 is a Z group.