Patent ID: 6458167
Filing Date: 2002-10-01
Classification: A61K,A61Q

Abstract:
A dyeing composition for keratinous substances, comprising,(a) a medium suitable for dyeing keratinous substances; and (b) at least one compound of formula (I) below or an acid addition salt thereof, said at least one compound of formula (I) being present in said composition in an amount effective for direct dyeing of keratinous substances; â€ƒwherein: R1, R2, R3, Râ€²1, Râ€²2, and Râ€²3, which may be identical or different, are chosen from a hydrogen atom; a halogen atom; a group Z as defined below; a (C1-C6)alkyl-carbonyl radical; an amino(C1-C6)alkylcarbonyl radical; an N-Z-amino(C1-C6)alkylcarbonyl radical; an N-(C1-C6)alkylamino(C1-C6)alkylcarbonyl radical; an N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl radical; an amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an N-Z-amino(C1-C6)alkylcarbonyl(C1-C6)-alkyl radical; an N-(C1-C6)alkylamino(C1-C6)-alkylcarbonyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylamino(C1-C6)alkyl-carbonyl(C1-C6)alkyl radical; a carboxyl radical; a (C1-C6)alkylcarboxyl radical; a C1-C6 alkylsulphonyl radical; an aminosulphonyl radical; an N-Z-amino-sulphonyl radical; a C1-C6 N-alkylaminosulphonyl radical; a C1-C6 N,N-dialkylaminosulphonyl radical; a C1-C6 aminosulphonylalkyl radical; a C1-C6 N-Z-aminosulphonylalkyl radical; an N-(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; a carbamyl radical; an N-(C1-C6)alkylcarbamyl radical; an N,N-di(C1-C6)alkylcarbamyl radical; a carbamyl(C1-C6)alkyl radical; an N-(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; a C1-C6 alkyl radical; a C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; a (C1-C6)alkoxy(C1-C6)alkyl radical; a C1-C6 trifluoroalkyl radical; a cyano radical; a nitro radical; an amino group NR4R5, wherein R4 and R5 are as defined below; a group OR6 or SR6, wherein R6 is as defined below; and a C1-C6 aminoalkyl radical wherein the alkyl may be unsubstituted or substituted with one or more hydroxyl radicals and wherein the amine is substituted with one or two identical or different radicals chosen from C1-C6 alkyl, C1-C6 monohydroxyalkyl, C2-C6 polyhydroxyalkyl, (C1-C6) alkylcarbonyl, carbamyl, N-(C1-C6)alkylcarbamyl or N,N-di(C1-C6)-alkylcarbamyl, C1-C6 alkylsulphonyl, formyl, trifluoro(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl and thiocarbamyl radicals, and from a group Z as defined below; A is chosen from a group NR4R5, wherein R4 and R5 are as defined below, and a group OR6, wherein R6 is as defined below; R4 and R5, which may be identical or different, are chosen from a hydrogen atom; a group Z as defined below; a C1-C6 alkyl radical; a C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; a (C1-C6)alkoxy(C1-C6)alkyl radical; an aryl radical; a benzyl radical; a cyano(C1-C6)alkyl radical; a carbamyl(C1-C6)alkyl radical; an N-(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; a thiocarbamyl (C2-C6)alkyl radical; a C1-C6 trifluoroalkyl radical; a C1-C6 sulphoalkyl radical; a (C1-C6)alkylcarboxyl(C1-C6)alkyl radical; a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical; a C1-C6 aminosulphonylalkyl radical; a C1-C6 N-Z-aminosulphonylalkyl radical; an N-(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; an N, N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; a (C1-C6)alkylcarbonyl(C1-C6)alkyl radical; a C1-C6 aminoalkyl radical; and a C1-C6 aminoalkyl radical wherein the alkyl can be unsubstituted or substituted with one or more hydroxyl radicals and wherein the amine is substituted with one or two identical or different radicals which are chosen from C1-C6 alkyl, C1-C6 monohydroxyalkyl, C2-C6 polyhydroxyalkyl, (C1-C6)alkylcarbonyl, carbamyl, N-(C1-C6)alkylcarbamyl or N,N-di(C1-C6)alkylcarbamyl, C1-C6 alkylsulphonyl, formyl, trifluoro-(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, thiocarbamyl radicals, and a group Z as defined below, or which may together form, with the nitrogen atom to which they are attached, a carbonaceous 5- or 6-membered ring or a 5- or 6-membered ring comprising one or more identical or different hetero atoms; R6 is chosen from a hydrogen atom; a C1-C6 alkyl radical; a C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; a group Z as defined below; a (C1-C6)alkoxy(C1-C6)alkyl radical; an aryl radical; a benzyl radical; a carboxy(C1-C6)alkyl radical; a (C1-C6)alkylcarboxyl(C1-C6)alkyl radical; a cyano(C1-C6)alkyl radical; a carbamyl(C1-C6)alkyl radical; an N-(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; a C1-C6 trifluoroalkyl radical; a C1-C6 aminosulphonylalkyl radical; a C1-C6 N-Z-aminosulphonylalkyl radical; an N-(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6) alkyl radical; a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical; a (C1-C6)alkylsulphonyl(C1-C6)alkyl radical; (C1-C6)alkylcarbonyl(C1-C6)alkyl radical; a C1-C6 aminoalkyl radical, wherein the alkyl is unsubstituted or substituted with one or more hydroxyl radicals; a C1-C6 aminoalkyl radical wherein the alkyl is unsubstituted or substituted with one or more hydroxyl radicals and wherein the amine is substituted with one or two identical or different radicals which are chosen from C1-C6 alkyl, C1-C6 monohydroxyalkyl, C2-C6 polyhydroxyalkyl, (C1-C6)alkylcarbonyl, formyl, trifluoro(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, carbamyl, N-(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, thiocarbamyl, C1-C6 alkylsulphonyl radicals, and a group Z as defined below, or which may together form, with the nitrogen atom to which they are attached, a carbonaceous 5- or 6-membered ring or a 5- or 6-membered ring comprising one or more identical or different hetero atoms; Z is chosen from the unsaturated cationic groups of formulae (II) and (III) below, and the saturated cationic groups of formula (IV) below: â€ƒwherein: D is a linker arm which is a linear or branched alkyl chain, which can be interrupted by one or more identical or different hetero atoms, can be substituted with one or more hydroxyl radicals or identical or different C1-C6 alkoxy radicals, and can bear one or more ketone functions; the ring members E, G, J, L, and M, which may be identical or different, are chosen from carbon, oxygen, sulphur and nitrogen atoms; n is an integer ranging from 0 to 4; m is an integer ranging from 0 to 5; the radicals R, which may be identical or different, are chosen from a second group Z which is identical to or different from the first group Z; a halogen atom; a hydroxyl radical; a C1-C6 alkyl radical; C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; a nitro radical; a cyano radical; a cyano(C1-C6)alkyl radical; a C1-C6 alkoxyl radical; a tri(C1-C6)alkylsilane(C1-C6)alkyl radical; an amido radical; an aldehydo radical; a carboxyl radical; a (C1-C6)alkylcarbonyl radical; a thio radical; a C1-C6 thioalkyl radical; a C1-C6 alkylthio radical; an amino radical; an amino radical protected with a (C1-C6) alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical; and a group NHRâ€³ or NRâ€³R, wherein Râ€³ and R, which may be identical or different, are chosen from a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical and a C2-C6 polyhydroxyalkyl radical; R7 is chosen from a C1-C6 alkyl radical; a C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; a cyano(C1-C6)alkyl radical; a tri(C1-C6)alkylsilane(C1-C6)alkyl radical; a (C1-C6)alkoxy(C1-C6)alkyl radical; a carbamyl-(C1-C6)alkyl radical; a (C1-C6)alkylcarboxy(C1-C6)-alkyl radical; a benzyl radical; and a second group Z which is identical to or different from the first group Z; R8, R9, and R10, which may be identical or different, are chosen from a C1-C6 alkyl radical; a C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; a (C1-C6)alkoxy(C1-C6)alkyl radical; a cyano(C1-C6)alkyl radical; an aryl radical; a benzyl radical; a C1-C6 amidoalkyl radial; a tri(C1-C6)alkylsilane(C1-C6)alkyl radical; and a C1-C6 aminoalkyl radical wherein the amine is protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical; or wherein two of the radicals R8, R9, and R10 form, together with the nitrogen atom to which they are attached, a saturated carbonaceous 5- or 6-membered ring or a 5- or 6-membered ring comprising one or more identical or different hetero atoms; or further wherein one of the radicals R8, R9, and R10 is a second group Z which is identical to or different from the first group Z; R11 is chosen from a C1-C6 alkyl radical; a C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; an aryl radical; a benzyl radical; a C1-C6 aminoalkyl radical; a C1-C6 aminoalkyl radical wherein the amine is protected with (C1-C6) alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical; a carboxy(C1-C6)alkyl radical; a cyano(C1-C6)alkyl radical; a carbamyl(C1-C6)alkyl radical; a C1-C6 trifluoroalkyl radical; a tri(C1-C6)alkylsilane(C1-C6)alkyl radical; a C1-C6 sulphonamidoalkyl radical; a (C1-C6)alkylcarboxyl(C1-C6)alkyl radical; a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical; a (C1-C6)alkylsulphonyl(C1-C6)alkyl radical; a (C1-C6)alkylketo(C1-C6)alkyl radical; an N-(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; and an N-(C1-C6)alkylsulphonamido(C1-C6)alkyl radical; x and y are integers equal to 0 or 1, with the provisos that: in the unsaturated cationic groups of formula (II): when x=0, the linker arm D is attached to the nitrogen atom, when x=1, the linker arm D is attached to one of the ring members E, G, J or L, y can take the value 1 only when: 1) the ring members E, G, J, and L are all carbon atoms, and the radical R7 is borne by the nitrogen atom of the unsaturated ring; or 2) at least one of the ring members E, G, J, and L is a nitrogen atom to which the radical R7 is attached; in the unsaturated cationic groups of formula (III): when x=0, the linker arm D is attached to the nitrogen atom, when x=1, the linker arm D is attached to one of the ring members E, G, J, L, or M, y can take the value 1 only when at least one of the ring members E, G, J, L, and M is a divalent atom and when the radical R7 is borne by the nitrogen atom of the unsaturated ring; in the cationic groups of formula (IV): when x=0, the linker arm is attached to the nitrogen atom bearing the radicals R8, R9, and R10, when x=1, two of the radicals R8, R9, and R10 form, together with the nitrogen atom to which they are attached, a saturated carbonaceous 5- or 6-membered ring or a 5- or 6-membered ring comprising one or more identical or different hetero atoms, and the linker arm D is borne by a carbon atom of said saturated ring; Xâˆ’is a monovalent or divalent anion; with the provisos that: in the compound of the formula (I), at least one of R1, R2, R3, Râ€²1, Râ€²2, Râ€²3 and A comprise a cationic group Z of formula (II) or (III); and when one and only one of the radicals R4, R5, or R6 is a group Z wherein the linker arm D is an alkyl chain comprising a ketone function, then said ketone function is not directly attached to the nitrogen atom of the group NR4R5 or to the oxygen atom of the OR6 group.