Patent EP-1502576-A2 (EP)
Inventor: ROZOT ROGER
IPC: A61K8/00
Filed: 2004-07-12
Abstract: The use of 2-(substituted thio)-acetamide compounds (I) for inducing and/or stimulating the growth of human keratin fibers, retarding their loss and/or increasing their density is new. Also new is the use of (I) as 15-hydroxy-prostaglandin dehydrogenase (15-PGDH) inhibitors. The use of 2-thio-acetamide compounds of formula R3SCH2CONR1R2 (I) or their salts is claimed as agents for inducing and/or stimulating the growth of human keratin fibers, retarding their loss and/or increasing their density. R1, R2H; 1-20C alkyl (optionally substituted (os) by one or more groups A1); a hydrocarbon ring or heterocycle, optionally fused with a second ring (optionally containing heteroatom(s)), where each ring optionally contains CO or CS function(s) and is os by one or more groups A3; or C(=NR)R', C(=NR)NR'R'', COR, CSR, COOR, CONRR', SO2R or SO2NRR'; R31-20C alkyl (optionally substituted (os) by one or more groups A2); a hydrocarbon ring, optionally fused with a second ring (optionally containing heteroatom(s)), where each ring optionally contains CO or CS function(s) and is os by one or more groups A3; a pyrrole, furan, thiophene and pyrazole ring , optionally fused with phenyl, pyridine or pyrimidine ring, where each ring optionally contains CO or CS function(s) and is os by one or more groups A3; a pyridine ring, optionally fused with a second ring (optionally containing heteroatom(s)), where each ring optionally contains CO or CS function(s) and is os by one or more groups A4; a heterocycle (other than pyrrole, furan, thiophene, pyrazole or pyridine), optionally fused with a second ring (optionally containing heteroatom(s)), where each ring optionally contains CO or CS function(s) and is os by one or more groups A3; or C(=NR)R', C(=NR)NR'R'', COR, CSR, COOR or CONRR'; A1halo; CF3, CN, OR, SR, NRR', NRC(=NR')NR''R''', COR, CSR, COOR, CONRR', CSNRR', NRCSR', NRCSNR'R'', NRCOR', NRCONR'R'', SO2NRR', NRSO2R', SO2R or SiRR'R''; or a hydrocarbon ring or heterocycle, optionally fused with a second ring (optionally containing heteroatom(s)), where each ring optionally contains CO or CS function(s) and is os by one or more groups A5; A2halo; CF3, CN, OR, SR, NRR', NRC(=NR')NR''R''', COR, CSR, COOR, CONRR', CSNRR', NRCSR', NRCSNR'R'', NRCOR', NRCONR'R'', SO2NRR', NRSO2R', SO2R or SiRR'R''; or a ring, optionally fused with a second ring, where each ring optionally contains heteroatom(s) and/or CO or CS function(s) and is os by one or more groups A5; A31-20C alkyl (os by one or more groups A5); or as for A2; A4halo; CF3, CN, OR, SR, NRC(=NR')NR''R''', COR, CSR, COOR, CONRR', CSNRR', NRCSR', NRCSNR'R'', NRCOR', NRCONR'R'', SO2NRR', NRSO2R', SO2R or SiRR'R''; 1-20C alkyl (os by one or more groups A5); or a ring, optionally fused with a second ring, where each ring optionally contains heteroatom(s) and/or CO or CS function(s) and is os by one or more groups A5; A5halo; CF3, CN, OR5, SR5, NR5R'5, NR5C(=NR'5)NR''5R'''5, COR5, CSR5, COOR5, CONR5R'5, CSNR5R'5, NR5CSR'5, NR5CSNR'5R''5, NRCOR', NR5CONR'5R''5, SO2NR5R'5, NR5SO2R'5, SO2R5 or SiR5R'5R''5; 1-20C alkyl; or a ring, optionally fused with a second ring, where each ring optionally contains heteroatom(s) and/or CO or CS function(s); R5, R'5, R''5H or 1-20C alkyl; and R, R', R'', R''' : H, 1-20C alkyl (os by one or more groups A5); or a ring, optionally fused with a second ring, where each ring optionally contains heteroatom(s) and/or CO or CS function(s) and is os by one or more groups A5. All heterocycles contain 1-4 heteroatom(s) selected from N, O and S. Independent claims are included for: (1) the use of (I) in cosmetic care and/or make-up compositions for use as above, in the production of care or treatment compositions for use as above, as 15-hydroxy-prostaglandin dehydrogenase (15-PGDH) inhibitors or in the production of care or treatment compositions for treating human keratin fibers for treating disorders associated with 15-PGDH; (2) topically applied care or make-up compositions (A) for keratin fibers, comprising (I) contained in a physiologically acceptable medium; and (3) corresponding cosmetic treatment, make-up or care processes, involving applying (A) to the fibers or skin where hair is to emerge, specifically the hair, scalp, eyelashes or eyelids. ACTIVITY : Endocrine-Gen. MECHANISM OF ACTION : 15-Hydroxy-prostaglandin dehydrogenase (15-PGDH) inhibitor. 2-(Benzothiazol-2-ylthio)-N-cyclopentyl-acetamide (Ia) had IC50 5 mu M for inhibition of 15-PDGH.