Patent EP-1584615-B1 (EP)
Inventor: PHILIPPE MICHEL
IPC: A61K8/891
Filed: 2005-04-01
Granted: 2008-05-28
Abstract: Use of a dimercaptomide (I) or their organic and mineral salts as a reducing agent for the permanent deformation of the keratin fibers, particularly human keratin fibers such as hair. Use of a dimercaptomide (I) of formula HS-A-CO-NH-B1-SH as a reducing agent for the permanent deformation of the keratin fibers, particularly human keratin fibers such as hair. A : (CH 2) n(optionally substituted by (i) 1-5C alkyl; phenyl; benzyl; amino; acetylamino; NH-CO-CH 2-NH 2; NH-CO-CH 2-CH 2-CH(NH 2)COOH; NH-CO-CH 2-CH 2-CH(COOH)COOH; CH 2-COOH; CH 2-COOCH 3; or CH 2-COOCH 2-CH 3or (ii) two methyl or ethyl); B1 : (CH 2) p(optionally substituted by (i) 1-5C alkyl; carboxyl; COOCH 3; COOEt; CONH 2; CONH-CH 3; CON(CH 3) 2; CONHCH 2-CH 3; CON(CH 2-CH 3) 2; CONH-CH 2-CHOH-CH 3; CO-NH-CH(COOH)-(CH 2) 4-NH 2; CO-NH-CH(COOH)-(CH 2) 4-N(CH 3) 2; CO-NH-CH 2-CH 2-COOEt; CO-NH-CH(COOH)-isopropyl; CO-NH-CH 2-R or (ii) 2 methyl); either n, p : 1-5; or n+p : 2-6; and R : CO-NH 2, (CH 2) 3-NH 2, (CH 2) 4-NH 2, (CH 2) 5-NH 2or (CH 2) 4-OH. Independent claims are also included for: (1) for the preparation of (I); (2) a process for permanent deformation of the keratin fibers, particularly human keratin fibers such as hair, comprising application of a reducer composition comprising (I) as a reducing agent and oxidizing composition on the fibers; (3) a reducing composition comprising (I) as a reducing agent; (4) kit for the permanent deformation of the hair, comprising reducing composition in a first compartment and oxidizing composition in a second compartment; and (5) (I) (provided that: (a) A is CH 2and B1 is (CH 2) x(where x is 2-5), C(CH 3) 2-CH 2; CH(Et)-CH 2; CH(CO-NR 1R 2)-CH 2or CH(CONR 1R 2)-CH 2-CH 2(where R 1and R 2is H or methyl, ethyl or 2-hydroxypropyl); (b) A is CH(CH 3) and B1 is (CH 2) x(where x is 1-5), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2-CH 2, CH(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2; (c) A is CH-R 3(where R 3is 2-5C alkyl and B1 is (CH 2) x(where x is 1-5), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2, CH(COOH)-CH 2-CH 2, CH(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2; (d) A is CH 2-CH 2or C(CH 3) 2-CH 2and B1 is (CH 2) x(where x is 1, 3 or 4); C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2-CH 2, CH(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2; (e) A is CH 2-CH(CH 3) and B1 is (CH 2) x(where x is 1-4), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2, CH(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2; (f) A is CH 2-CH-R 4(where R 4is phenyl or COO-CH 3or COO-CH 2-CH 3and B1 is (CH 2) x(x is 1-4), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2-CH 2, H(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2; (g) A is CH 2-CH(CH 2-COOH) or CH 2-CH(NH-CH 2-COOH) and B1 is (CH 2) x(where x is 1-4), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2, CH(COOH)-CH 2-CH 2, CH(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2; (h) A is C(CH 3) 2and B1 is (CH 2) x(where x is 1, 3, 4 or 5), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(CO-NHCH 3)-CH 2, CH(CO-NHEt)-CH 2, CH(CO-NH-CH 2-CHOHCH 3)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2; (i) A is C(Et) 2and B1 is (CH 2) x(where x is 1-5), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2-CH 2, CH(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2; and (j) CH 2-C(CH 3) 2or CH(CH 2-Ph) and B1 is (CH 2) x(x is 1-4), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2); (k) A is CH 2-C(Et) 2and B1 is (CH 2) x(where x is 1-4), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2-CH 2, CH(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2; (l) A is CH 2-CH(NH 2) and B1 is (CH 2) x(where x is 1, 3 or 4), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2-CH 2, CH(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2; (m) A is CH 2-CH(NHAc) and B1 is (CH 2) x(where x is 1, 3 or 4), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2-CH 2, CH(CO-NH-CH 3)-CH 2, CH(CO-NH-Et)-CH 2, CH(CO-N(CH 3) 2)-CH 2, CH(CO-NR 1R 2)-CH 2-CH 2; (n) A is CH 2-CH(NH-CO-CH 2-CH 2-CH(NH 2)COOH) or CH 2-CH(NH-CO-CH 2-NH 2) or CH 2-CH(NH-CO-CH(NH 2)-CH 2-CH(COOH) 2or CH 2-CH(NH-CO-CH 2-CH 2-CH 2-CH(NH 2)COOH) and B1 is (CH 2) x(where x is 1-4), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2-CH 2, CH(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2; (o) A is (CH 2) 3and B1 is (CH 2) x(where x is 1-3), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2, CH(COOH)-CH 2-CH 2, CH(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2; (p) A is (CH 2) 4and B1 is (CH 2) x(x is 1 or 2), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2, CH(COOH)-CH 2-CH 2, CH(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2; (q) A is (CH 2) 5and B1 is CH 2; and (r) A is CH-Ph and B1 is (CH 2)x (where x is 1-5), C(CH 3) 2-CH 2, CH(Et)-CH 2, CH(COOH)-CH 2, CH(COOH)-CH 2-CH 2, CH(CO-NR 1R 2)-CH 2or CH(CO-NR 1R 2)-CH 2-CH 2).