Patent EP-1006153-B1 (EP)
Inventor: GENET ALAIN
IPC: A61K8/34
Filed: 1999-10-22
Granted: 2003-02-12
Abstract: Bis-aminoanthraquinones (I) are new. Bis-aminoanthraquinones of formula (I) and their acid-addition salts are new, except for compounds of formula (VI). B = 1-14C alkylene optionally interrupted by heteroatom(s) and optionally substituted by OH, OA and/or oxo; A = 1-6C alkyl; R1-R4, R'1-R'4 = bonds to B, H, halogen, Z, A, A'OH, 2-6C polyhydroxyalkyl, CN, NO2, COOH, CONH2, SO3H, NHR5, OR6 or SR6; A' = 1-6C alkylene; R5 = a bond to B, H, Z, A, A'OH, 2-6C polyhydroxyalkyl, A'OA, aryl, benzyl, A'CN, A'CONH2, A'CONHA, A'CONA2, A'CSNH2, 1-6C trifluoroalkyl, A'SO3H, A'COOA, A'SOA, A'SO2NH2, A'SO2NHZ, A'SO2NHA, A'SO2NA2, A'COA, A''NH2 or A''NQQ'; A'' = 1-6C alkylene optionally mono- or polysubstituted by OH; Q, Q' = A, A'OH, 2-6C polyhydroxyalkyl, COA, CONH2, CONHA, CONA2, SO2A, CHO, 2-7C trifluoroalkanoyl, COOA, CSNH2 or Z, or are linked to form a 5- or 6-membered ring optionally containing other heteroatoms;   R6 = a bond to B, H, A, A'OH, 2-6C polyhydroxyalkyl, Z, A'OA, aryl, benzyl, A'COOH, A'COOA, A'CN. A'CONH2, A'CONHA, A'CONA2, 1-6C trifluoroalkyl, A'SO2NH2, A'SO2NHZ, A'SO2NHA, A'SO2NA2, A'SOA, A'SO2A, A'COA, A''NH2 or A'NQQ'; Z = a group of formula (II)-(IV): D = 1-14C alkylene optionally interrupted by heteroatom(s) and optionally substituted by OH, OA and/or oxo; E, G, J, L, M = C, O, S or N; n = 0-4; m = 0-4; R = Z (sic), 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 NR'R''; R', R'' = A, A'OH or 2-6C polyhydroxyalkyl; R7 = A, A'OH, 2-6C polyhydroxyalkyl, A'CN, A'SiA3, A'OA, A'CONH2, A'COOA, benzyl or Z; R8-R10 = 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 R8-R10 can form a 5- or 6-membered saturated ring optionally containing other heteroatoms and optionally substituted by halogen, OH, A, A'OH, 2-6C polyhydroxyalkyl, NO2, CN, A'CN, OA, A'SiA3, CONH2, CHO, COOH, 1-6C oxoalkyl, SH, A'SH, SA, NH2, NHCOA, NHCONH2 or NHSO2A, or one of R8-R10 can be Z; R11 = A, A'OH, 2-6C polyhydroxyalkyl, aryl, benzyl, A'NH2, A'NHCOA, A'NHCONH2, A'NHSO2A, A'COOH, A'CN, A'CONH2, 1-6C trifluoroalkyl, A'SiA3, A'SO2NH2, A'COOA, A'SOA, A'SO2A, A'COA, A'CONHA or A'SO2NHA; x, y = 0 or 1; and X<-> = a mono- or divalent anion; provided that: (a) when Z is of formula (II), then (i) D is attached to the N atom when x = 0, (ii) D is attached to E, G, J or L when x = 1, (iii) y = 0 when E, G, J and L are all C and R7 is attached to the ring N atom, and (iv) y = 0 when at least one of E, G, J and L is a N atom to which R7 is attached; (b) when Z is of formula (III), then (i) D is attached to the N atom when x = 0, (ii) D is attached to E, G, J, L or M when x = 1, (iii) y can be 1 only when at least one of E, G, J, L or M is a divalent atom and R7 is attached to the ring N atom; (c) when Z is of formula (IV), then (i) D is attached to the N atom when x = 0 and (ii) when x = 1, then two of R8-R10 form a ring and D is attached to a C atom of this ring; and (d) the number of Z groups is at least 1. alk = 1-5C alkylene; R1-R4 = H, halogen, alkyl or OH; R5 = H or alkyl; R8, R9 = alkyl, mono- or polyhydroxyalkyl or aryl; D = a group as defined above; and X<-> = an anion. Independent claims are also included for the following: (1) a composition for dyeing keratinic fibers, especially for direct dyeing of human keratinic fibers, containing at least one compound (I); (2) a process for dyeing keratinic fibers, comprising applying the composition of (1) to the dry or wet fibers and either: (a) drying the fibers without rinsing or (b) allowing the composition to act for 3-60 minutes and then rinsing them, optionally washing them, rinsing them and drying them.