Patent EP-0989128-A1 (EP)
Inventor: TERRANOVA ERIC
IPC: C07D521/00
Filed: 1999-08-30
Abstract: Cationic 4-hydroxyindole derivatives (I) are new. Compounds of formula (I) and their acid-addition salts are new: R1 = H, Z, A, A'OH, 2-4C polyhydroxyalkyl, A'OA, A'OA'OH, A'Q, A'SA, A'SA'OH, (2-4C)polyhydroxyalkylthio(1-4C)alkyl, A'COOH, A'COOA, A'NHCOMe, A'CN, A, 1-4C haloalkyl, 1-4C phosphoalkyl or 1-4C sulfoalkyl; A = 1-4C alkyl; A' = 1-4C alkylene; A = 1-4C trifluoroalkyl; Q = amino optionally mono- or disubstituted by A, acetyl, A'OH or 2-4C polyhydroxyalkyl; R2, R3 = H, halogen, Z, NHZ, A, COOH, COOA or CHO; R4, R5 = H, halogen, Z, NHZ, A, OA, acetylamino, 1-5C monohydroxyalkyl, 2-4C polyhydroxyalkyl or A'OA; thienyl or furyl; phenyl or aryl(1-4C)alkyl optionally substituted by halogen, A, CF3, OA, NH2, NHA or NA2; A'NHA or A'NA2; 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 = 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, 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 R7-R9 can be Z; R10 = 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; x, y = 0 or 1; 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 R6 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 R6 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 R6 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 R7-R9 when x = 0; and (b) D is attached to a C atom of a saturated ring formed by R7-R9 when x = 1; and (D) at least one Z group is present. 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 dyeing keratinic fibers, comprising applying at least one composition as in (1) to the fibers and developing the color with an oxidizing agent added to the composition just before use or applied separately (simultaneously or sequentially) in an oxidizing composition; (3) a kit comprising a compartment containing a composition as in (1) and a compartment containing an oxidizing composition.