Patent EP-0984006-A1 (EP)
Inventor: GENET ALAIN
IPC: A61K8/49
Filed: 1999-07-28
Abstract: Cationic bis-o-phenylenediamine derivatives (I) are new. Compounds of formula (I) and their acid-addition salts are new. B = alkylene optionally interrupted by one or more Z groups and/or heteroatoms and optionally substituted by OH, 1-6C alkoxy and/or oxo;   R1-R3, R'1-R'3 = bonds to B, H, halogen, Z, COA, COA'NH2, COA'NHZ, COA'NHA, COA'NA2, A'COA'NH2, A'COA'NHZ, A'COA'NHA, A'COA'NA2, COOH, COOA, SO2A, SO2NH2, SO2NHZ, SO2NHA, SO2NA2, A'SO2NH2, A'SO2NHZ, A'SO2NHA, A'SO2NA2, CONH2, CONHA, CONA2, A'CONH2, A'CONHA, A'CONA2, A, A'OH, 2-6C polyhydroxyalkyl, A'OA, A'', CN, OR6 or SR6; or an amino group protected by COA, COOA, COA'', COA'NH2, COA'NHZ, COA'NHA, COA'NA2, CONH2, CONHA, CONA2, SO2A, SO2NH2, SO2NHZ, SO2NHA, SO2NA2, CSNH2, CHO or Z'; A = 1-6C alkyl; A' = 1-6C alkylene; A'' = 1-6C trifluoroalkyl; R6 = a bond to B, A, A'OH, 2-6C polyhydroxyalkyl, Z, A'OA, aryl, benzyl, A'COOH, A'COOA, A'CN, A'CONH2, A'CONHA, A'CONA2, A'', A'SO2NH2, A'SO2NHZ,, A'SO2NHA, A'SO2NA2, A'SOA, A'SO2A, A'COA or A'NH2; or 1-6C aminoalkyl N-substituted by 1 or 2 of A, A'OH, 2-6C polyhydroxyalkyl, COA, CHO, COA'', COOA, CONH2, CONHA, CONA2, CSNH2, SO2A and Z; R4-R8, R'4-R'8 = bonds to B, H, Z, A, A'OH, 2-6C polyhydroxyalkyl, Z, A'OA, aryl, benzyl, A'COOH, A'COOA, A'CN, A'CONH2, A'CONHA, A'CONA2, A'', A'SO2NH2, A'SO2NHZ,, A'SO2NHA, A'SO2NA2, A'SOA, A'SO2A, A'COA or A'NH2; or 1-6C aminoalkyl N-substituted by 1 or 2 of A, A'OH, 2-6C polyhydroxyalkyl, COA, CHO, COA'', COOA, CONH2, CONHA, CONA2, CSNH2, SO2A and Z; Z = a group of formula (i)-(iii): D = alkylene optionally interrupted by one or more heteroatoms and optionally substituted by OH, 1-6C alkoxy and/or oxo; E, G, J, L, M = C, O, S or N; n = 0-4; m = 0-5; R = bonds to B, Z, halogen, OH, A, A'OH, 2-6C polyhydroxyalkyl, NO2, CN, A'CN, OA, A'SiA3, CONH2, CHO, COOH, COA, SH, A'SH, SA, NH2, NHCOA, NHCONH2, NHSO2A, NHR or NRR'; R, R' = A, A'OH or 2-6C polyhydroxyalkyl; R9 = a bond to B, A, A'OH, 2-6C polyhydroxyalkyl, A'CN, A'SiA3, A'OA, A'CONH2, A'COOA, benzyl or Z; R10-R12 = bonds to B, A, A'OH, 2-6C polyhydroxyalkyl, A'OA, A'CN, aryl, benzyl, A'CONH2, A'SiA3, A'NHCOA, A'NHCONH2 or A'NHSO2A; or two of R7-R9 form a 5- or 6-membered ring optionally substituted by halogen, OH, A, A'OH, 2-6C polyhydroxyalkyl, NO2, CN, A'CN, OA, A'SiA3, CONH2, CHO, COOH, COA, SH, A'SH, SA, NH2, NHCOA, NHCONH2 or NHSO2A; or one of R10-R12 can be Z; R13 = a bond to B, A, A'OH, 2-6C polyhydroxyalkyl, aryl, benzyl, A'NH2, A'NHCOA, A'NHCONH2, A'NHSO2A, A'COOH, A'CN, A'CONH2, A'', A'SiA3, A'SO2NH2, A'COOA, A'SOA, A'SO2A, A'COA, A'CONHA or A'SO2NHA; Z' = Z in which B has an oxo group directly attached to the N atom; x, y = 0 or 1; and X<-> = a mono- or divalent anion; provided that: (A) when Z is of formula (i), then: (a) D is attached to the nitrogen atom when x = 0; (b) D is attached to E, G, J or L when x = 1; and (c) y can be 1 only if R9 is bonded to the ring N atom when E, G, J and L are all C or if at least one of E, G, J and L is a N atom to which R9 is bonded; (B) when Z is of formula (ii), then: (a) D is attached to the nitrogen atom when x = 0; (b) D is attached to E, G, J or L when x = 1; and (c) y can be 1 only if at least one of E, G, J, L and M is a divalent atom and R9 is bonded to the ring N atom; (C) when Z is a group of formula (iii), then: (a) D is attached to the N atom bearing R10 and R11 when x = 0; and (b) D is attached to a C atom of a saturated ring formed by R10 and R11 when x = 1; (D) at least one Z group is present; (E) when R4, R5, R'4, R'5, R7, R8, R'7 and/or R'8 is a Z group in which D has an oxo group, this oxo group is not directly attached to the N atom of NR4R5, NR'4R'5, NR7R8 or NR'7R'8; and (F) when R4, R5, R'4, R'5, R7, R8, R'7 and/or R'8 is a bond to a B group having an oxo group, this oxo group is not directly attached to the N atom of NR4R5, NR'4R'5, NR7R8 or NR'7R'8. Independent claims are also included for the following: (1) a composition for oxidation dyeing of keratinic fibers, containing at least one compound (I); (2) a method for oxidation dyeing of keratinic fibers, comprising applying at least one composition as in (1) to the fibers for a time sufficient for the desired color to develop, either in air or with the aid of an oxidizing agent; and (3) a kit comprising a compartment containing the composition of (1) and a compartment containing an oxidizing composition.