Patent ID: 6391062
Filing Date: 2002-05-21
Classification: A61K,A61Q

Abstract:
A method of dyeing keratin substances, comprising applying to said keratin substances a direct dye composition comprising, in an amount effective for dyeing, at least one compound of formula (I) or an acid addition salt thereof: in which:R1 is chosen from a hydrogen atom; a group Z; an amino(C1-C6)alkylcarbonyl (C1-C6)alkyl radical; an Nâ€”Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an Nâ€”(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an amino-sulphonyl(C1-C6)alkyl radical; an Nâ€”Z-aminosulphonyl(C1-C6)alkyl radical; an Nâ€”(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylamino-sulphonyl(C1-C6)alkyl radical; a carbamyl(C1-C6)alkyl radical; an Nâ€”(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; and a C1-C6 trifluoroalkyl radical; R2 and R3, which are identical or different, are chosen from a hydrogen atom; a halogen atom; a group Z; a (C1-C6)alkylcarbonyl radical; an amino (C1-C6) alkylcarbonyl radical; an Nâ€”Z-amino(C1-C6) alkylcarbonyl radical; an Nâ€”(C1-C6)alkylamino(C1-C6)alkyl-carbonyl radical; an N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl radical; an amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an Nâ€”Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an Nâ€”(C1-C6) alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; a carboxyl radical; a (C1-C6)alkylcarboxy radical; a C1-C6 alkylsulphonyl radical; an aminosulphonyl radical; an Nâ€”Z-aminosulphonyl radical; an Nâ€”(C1-C6)alkylaminosulphonyl radical; an N,N-di(C1-C6)alkylaminosulphonyl radical; an aminosulphonyl(C1-C6)alkyl radical; an Nâ€”Z-aminosulphonyl(C1-C6)alkyl radical; an Nâ€”(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; a carbamyl radical; an Nâ€”(C1-C6)alkylcarbamyl radical; an N,N-di(C1-C6)alkylcarbamyl radical; a carbamyl(C1-C6)alkyl radical; an Nâ€”(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; a C1-C6alkyl radical; a hydroxyl radical; a nitro 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; an amino radical; an Nâ€”(C1-C6)alkylamino radical; an N,N-di(C1-C6)alkylamino radical, wherein the two alkyl substituents optionally form a 5- or 6-membered ring; an N-hydroxy(C1-C6) alkylamino radical; an N,N-bis(hydroxy(C1-C6)alkyl)amino radical; an N-polyhydroxy(C2-C6)alkylamino radical; an N,N-bis(polyhydroxy(C2-C6)alkyl)amino radical; an amino(C1-C6)alkylamino radical in which the terminal amino group is unsubstituted or substituted with one or two C1-C6 alkyl radicals, said alkyl radicals optionally forming a saturated or unsaturated 5- or 6-membered ring; an amino group protected with a (C1-C6)alkylcarbonyl, trifluoro(C1-C6)alkylcarbonyl, amino(C1-C6)alkylcarbonyl, Nâ€”Z-amino(C1-C6)alkylcarbonyl, Nâ€”(C1-C6)alkylamino(C1-C6)alkyl-carbonyl, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl or formyl radical; and a group OR4 or SR4; R2 and R3 alternatively may together form an unsaturated ring of formula (II) below: â€ƒin which said radical R1 is chosen from a hydrogen atom; a group Z; an amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an Nâ€”Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an Nâ€”(C1-C6)alkylamino(C1-C6)alkyl carbonyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical; an amino-sulphonyl(C1-C6)alkyl radical; an Nâ€”Z-aminosulphonyl(C1-C6)alkyl radical; an Nâ€”(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical; an N,N-di(C1-C6)alkylamino-sulphonyl(C1-C6)alkyl radical; a carbamyl(C1-C6)alkyl radical; an Nâ€”(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; and a C1-C6 trifluoroalkyl radical; R4 is chosen from a C1-C6 alkyl radical; a C1-C6 monohydroxyalkyl radical; a C2-C6 polyhydroxyalkyl radical; a group Z; a (C1-C6)alkoxy(C1-C6)alkyl; an aryl radical; a benzyl radical; a carboxy(C1-C6)alkyl radical; a (C1-C6)alkylcarboxy(C1-C6)alkyl radical; a cyano(C1-C6)alkyl radical; a carbamyl (C1-C6)alkyl radical; an Nâ€”(C1-C6)alkyl-carbamyl(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 Nâ€”Z-aminosulphonyl-alkyl radical; an Nâ€”(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; a (C1-C6)alkylcarbonyl(C1-C6)alkyl radical; a C1-C6 aminoalkyl radical; and a C1-C6 aminoalkyl radical in which 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, formyl, trifluoro (C1-C6)alkylcarbonyl, (C1-C6) alkylcarboxyl, and C1-C6 alkylsulphonyl radicals; Z is chosen from an unsaturated cationic group of formulae (III) or (IV), and a saturated cationic group of formula (V): â€ƒin which: D is a linker arm chosen from linear and branched alkyl chains, said chains being optionally interrupted by one or more hetero atoms, optionally substituted with one or more hydroxyl or C1-C6 alkoxy radicals, and optionally having one or more ketone functions; Xâˆ’ is chosen from monovalent and divalent anions; said ring members E, G, J, L and M, which are identical or different, are chosen from a carbon, oxygen, sulphur or nitrogen atom; n is an integer ranging from 0 to 4; m is an integer ranging from 0 to 5; said radicals R, which are identical or different, are chosen from a covalent bond, a group Z, a halogen atom, a hydroxyl radical, a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical, a C2-C6 polyhydroxyalkyl radical, a nitro radical, a cyano radical, a cyano(C1-C6)alkyl radical, a C1-C6 alkoxy 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€³Râ€²â€³ in which Râ€³ and Râ€²â€³, which are identical or different, and are chosen from a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical and a C2-C6 polyhydroxyalkyl radical; when, in formula (III) or (IV), n or m is greater than 2, two adjacent radicals R together optionally form an unsaturated 5- or 6-membered ring which is carbon-based or which contains one or more hetero atoms; R5 is chosen from a covalent bond, 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 group Z; R6, R7 and R8, which are identical or different, are chosen from a covalent bond, 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 radical, a tri(C1-C6)alkylsilane(C1-C6)alkyl radical and a C1-C6 aminoalkyl radical in which the amine is protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical; two of the radicals R6, R7 and R8 together optionally form, with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring which is carbon-based or contains one or more hetero atoms, one of the radicals R6, R7 and R8 optionally is chosen from a second group Z which is identical to or different from the first group Z; R9 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 in which the amine is protected with a (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)alkylcarboxy(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 Nâ€”(C1-C6)alkylcarbamyl(C1-C6)alkyl radical; and an Nâ€”(C1-C6)alkylsulphonamido(C1-C6)alkyl radical; a and y are integers equal to 0 or 1; with the following provisos: (A) in the unsaturated cationic groups of formula (III): â€ƒwhen a=0, the linker arm D is attached to the nitrogen atom, â€ƒwhen a=1, the linker arm D is attached to one of the ring members E, G, J or L, â€ƒy can take the value 1 only when: (1) the ring-members E, G, J and L simultaneously are a carbon atom and when the radical R5 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 R5 is attached; (B) in the unsaturated cationic groups of formula (IV): â€ƒwhen a=0, the linker arm D is attached to the nitrogen atom, â€ƒwhen a=1, the linker arm D is attached to one of the ring members E, G, J, L or M, â€ƒy 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 R5 is borne by the nitrogen atom of the unsaturated ring; (C) in the cationic groups of formula (V): â€ƒwhen a=0, then the linker arm D is attached to the nitrogen atom bearing the radicals R7 and R8, when a=1, then two of the radicals R7 and R8 form, together with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring as defined above, and the linker arm D is borne by a carbon atom of the saturated ring; and with the overall proviso that: the number of cationic groups Z of formula (III), (IV) or (V) is at least equal to 1.