Patent FR-2886844-A1 (FR)
Title: Use of 2-oxyacetamide compounds for promoting, inducing and/or stimulating the pigmentation of human keratin materials, preventing and/or limiting the depigmentation, and/or bleaching of keratin materials
Inventor: ROZOT ROGER
IPC: A61K8/42
Filed: 2005-06-09
Abstract: Use of 2-oxyacetamide compounds (I) and their salts or solvates as an agent for promoting, inducing and/or stimulating the pigmentation of human keratin materials, as an agent for preventing and/or limiting the depigmentation, and/or bleaching of keratin materials. Use of 2-oxyacetamide compounds (I) of formula (R 3-O-CH 2-CO-N(R 1R 2) and their salts or solvates as an agent for promoting, inducing and/or stimulating the pigmentation of human keratin materials, as an agent for preventing and/or limiting the depigmentation, and/or bleaching of keratin materials. R 1, R 2H (with R 1different from R 2), 1-20C alkyl radical (optionally substituted by A 1), hydrocarbon-based ring C 1>of 3-7 atoms (optionally fused to at least one ring C 2>of 4-7 atoms) (the ring C 2>optionally containing at least one heteroatom to form a heterocycle Hy 2) (the rings C 1>and C 2>optionally comprising a carbonyl or thiocarbonyl function and/or substituted by A 2), heterocycle Hy 1(optionally fused to a ring C 2>of 4-7 atoms, the ring C2 optionally containing at least one heteroatom to form a heterocycle Hy 2) (the rings Hy 1and C 2>possibly comprising (thio)carbonyl function and/or substituted by at least one substituent A 1), C(=NR)R-a, C(=NR)NR-aR-b, COR, CSR, COOR, CONRR-a, SO 2R or SO 2NRR-a; R3 : 1-20C alkyl radical (optionally substituted by A 1), hydrocarbon-based ring C 3>of 3-7 atoms (optionally fused to at least one ring C 4>of 5-7 atoms optionally containing at least one heteroatom to form a heterocycle Hy 4) (the rings C 3>and C 4>optionally comprising a carbonyl or thiocarbonyl function and/or substituted by A 2), heterocycle Hy 3of pyrrole, furan, thiophene or pyrazole rings (optionally fused to a ring C 5>representing a phenyl, pyridine or pyrimidine) (the heterocycle Hy 3and the ring C 5>optionally substituted by A 1) or heterocycle Hy 5different from Hy 3and optionally fused to a ring C 6>of 4-7 atoms (the rings Hy 5and C 6>possibly comprising (thio)carbonyl function and/or substituted by at least one substituent A 1)) (the ring C 6>optionally containing at least one heteroatom to form a heterocycle Hy 6); R, R-a, R-b : H, 1-20C alkyl radical (optionally substituted by A 1), a ring C 7>of 4-7 atoms (optionally containing at least one heteroatom to form a heterocycle Hy 7and/or optionally fused to a ring C 8>of 4-7 atoms optionally containing at least one heteroatom to form a heterocycle Hy 8) (the rings C 7>and C 8>optionally substituted by A 1and possibly comprising a (thio)carbonyl function); A 1halo, 1-20C alkyl radical (optionally substituted by group OR 5), a ring C 9>of 4-15 atoms (optionally containing at least one heteroatom to form a heterocycle Hy 9and/or optionally fused to a ring C 10>of 4-7 atoms) (the rings C 9>and C 10>optionally comprising a (thio)carbonyl function and/or at least one substituent A 3of OR 5, CF 3, halo or 1-20C alkyl radical), CF 3, CN, OR 4, SR 4, NR 4R a4, NR 4C(=NR a4)NR b4R c4, COR 4, CSR 4, COOR 4, CONR 4R a4, NR 4COR a4, NR 4CONR a4R b4, SO 2NR 4R a4, NR 4SO 2R a4, SO 2R 4, SiR 4R a4R b4, Si(OR 4)(OR a4)OR b4or SO 3H; R 4, R a4-R c4H or 1-20C alkyl radical (optionally substituted by heterocycle Hy 10or CONR 5R a5); A 2halo, CF 3, CN, OR 4, SR 4, NR 4R a4, OCOR 4, COR 4, CSR 4, COOR 4, SO 2R 4, SiR 4R-a 4R b4, NO 2, OCF 3(where R 4, R a4-R c4is H or 1-20C alkyl radical (optionally substituted by phenyl radical)), 1-20C alkyl radical (optionally substituted by OR 5), a ring C 11>of 4-7 atoms optionally containing at least one heteroatom to form a heterocycle Hy 11and/or optionally fused to a ring C 12>of 4-7 atoms (the rings C 11>and C 12>possibly comprising a (thio)carbonyl function and/or at least one substitutet A 3of OR 5, CF 3, halo or 1-20C alkyl radical); R 5, R a5H or 1-20C alkyl radical; Hy 1, Hy 2, Hy 4-Hy 8, Hy 10, Hy 11heterocycle of 4-7 atoms possibly containing from 1-4 heteroatoms of N, O or S and/or comprising (thio)carbonyl function; and Hy 9heterocycle of 4-15 atoms possibly containing from 1-5 heteroatoms of N, O or S and/or comprising (thio)carbonyl function. An independent claim is included for cosmetic process for promoting, inducing and/or stimulating the pigmentation of human keratin materials, preventing and/or limiting the depigmentation, and bleaching of keratin materials comprising applying (I). ACTIVITY : None given. MECHANISM OF ACTION : 15-Hydroxy-prostaglandin dehydrogenase (15-PGDH) inhibitor. (I) were tested for 15-PGDH inhibitory activity using a biological assay. The percentage inhibition of 15-PGDH by 3-(2-(quinolin-8-yloxy)-N-(2-trifluoromethylphenyl)acetamide) was 128%.