Patent FR-2881427-A1 (FR)
Title: Use of 3-sulfanylpropanamide compound having 15-hydroxyprostaglandin dehydrogenase type 1 inhibitory activity, as agent for inducing and/or stimulating growth of keratin fibres and/or for stopping their loss and/or increasing their density
Inventor: BRETON PHILIPPE
IPC: A61K31/16
Filed: 2005-01-31
Abstract: Use of 3-sulfanylpropanamide compound (I) or its salt and/or solvate as an agent for inducing and/or stimulating the growth of keratin fibres (human), and/or for stopping their loss and/or increasing their density. Use of 3-sulfanylpropanamide compound (I) of formula R 3-S-C(H) 2-C(H) 2-C(=O)-N(R 2)-R 1or its salt and/or solvate as an agent for inducing and/or stimulating the growth of keratin fibres (human), and/or for stopping their loss and/or increasing their density. R 1, R 21-20C alkyl, saturated hydrocarbon-based ring 1C (both optionally substituted by A 1), H or unsaturated hydrocarbon-based ring 2C (optionally substituted by A 2); R 3H, 1-20C alkyl (optionally substituted by A 3) or saturated hydrocarbon-based ring 3C (optionally substituted by A 4); A 1F, CF 3, CN, OR, SR, NRR-a, SO 2NRR-a, NRSO 2R-a, SO 2R, alkyl compound of formula -X-C(=W 1)-Y 1(Ib), saturated hydrocarbon-based ring 4C (optionally substituted by A 4), heterocycle (Hy 1) selected from pyrrole (heterocycle substituted by A 4), furan, di- or tetrahydrofuran, thiophene, thiazole, (is)oxazole, (is)oxazolidine, oxadiazole, pyridine, pyran, di- or tetrahydropyran, pyrimidine, piperazine, pyridazine, pyrazine, morpholine, (iso)quinoline, 2-thiohydantoin, 2-oxo-2,3-dihydro-1,3-thiazole, pyridone, unsaturated hydrocarbon-based ring 3C (optionally substituted by A 4or optionally fused to a hydrocarbon-based or heterocyclic ring 6C); A 2F, CF 3, CN, OR, SR, NRR-a, COR, COOR, CONRR-a, NRCOR-a, NRCONR-aR-b, SO 2NRR-a, NRSO 2R-a, SO 2R or 1-20C alkyl (optionally substituted by A 4); W 1O, NH, S; X : O, NH, 1-6C alkylamino; Y 11-4C alkyl, 1-6C alkoxy, NH 2or (di)1-6C alkylamino; A 3saturated hydrocarbon-based ring 4C, unsaturated hydrocarbon-based ring 5C (both optionally substituted by A 4), F, CF 3, CN, OR, SR, NRR-a, (Ib) or heterocycle Hy 2(optionally substituted by A 4and containing heteroatom(s) of N, O or S); A 4F, CF 3, CN, OR, SR, NRR-a, 1-20C alkyl or 6C (optionally fused to another ring 7C and optionally containing heteroatom(s) of heterocycle Hy 2); and R, R-a, R-b : H, 1-6C alkyl group (optionally substituted by A 4), unsaturated hydrocarbon-based ring 5C (optionally substituted by A 4) or heterocycle Hy 2comprising at least one hetero atom of N, S or O and substituted by A 4. NB. Hy 2is not defined. Independent claims are also included for: (1) cosmetic process for treating human keratin fibres and/or skin, from the fibres emerge, comprising applying a cosmetic composition comprising (I), leaving the composition in contact with the keratin fibres and/or the skin, and optionally rinsing the fibres and/or the skin; (2) cosmetic process for caring for and/or making up human eyelashes, to improve their condition and/or their appearance, comprising applying to the eyelashes and/or the eyelids a mascara composition comprising (I) and leaving the composition in contact with the eyelashes and/or the eyelids; (3) cosmetic process for caring for human hair and/or the scalp, to improve their condition and/or their appearance, comprising applying a cosmetic composition comprising (I) and leaving the composition in contact with the hair and/or the scalp, and optionally rinsing the hair and/or the scalp; (4) cosmetic process for treating human skin, to improve its condition and/or its appearance, comprising applying to the skin a cosmetic composition comprising (I) and leaving the composition in contact with the skin, and optionally rinsing it off; and (5) 3-sulfanylpropanamide compound of formula T-S-C(H) 2-C(H) 2-C(=O)-N(H)-C(H) 2-Q (III), CH 3-S-CH 2-CH 2-C(=O)-NH-CH 2-CH 2-CH 2-CH 2-CH 2-CH 3(IV), and 3-sulfanylpropanamide compounds of formulae (V), (VII) and (VIII). Q : phenyl (optionally substituted with Z) or heteroaromatic selected from pyrimidine, (iso)quinoline, pyrrole, furan or thiophene (all optionally substituted with Z); and Z : F, CF 3, CN, OR, SR, NRR-a, SO 2NRR-a, NRSO 2R-a, SO 2R, SiRR-aR-b or (Ib). [Image] ACTIVITY : Endocrine-Gen.; Keratolytic. MECHANISM OF ACTION : 15-Hydroxyprostaglandin dehydrogenase type 1 inhibitor. The effect of (I) to inhibit 15-hydroxyprostaglandin dehydrogenase type 1 was tested using biological assays. The results showed that N-[(5-methyl-2-furyl)methyl]-3-(methylsulfanyl)propanamide exhibited the median inhibitory concentration value of 0.8 mu M.