Patent EP-1775294-A1 (EP)
Inventor: BOULLE CHRISTOPHE
IPC: C07D417/06
Filed: 2006-09-18
Abstract: Phenylfurylmethylthiazolidine-2,4-dione and phenylthienylmethylthiazolidine-2,4-dione compound (I), are new. Phenylfurylmethylthiazolidine-2,4-dione and phenylthienylmethylthiazolidine-2,4-dione compounds of formula (I), their salts and/or solvates, are new. X : O or S; A1H, linear or branched and optionally saturated 1-20C alkyl (optionally substituted by at least one Z1); A2-A5A1, 3-7 membered optionally saturated hydrocarbyl (optionally substituted by at least one Z1) or Z1; p : 0 - 5; Z1F, Cl, Br, CF3, OCF3, CN, NO2, OZ2, OCOZ2, OCONZ2Za2, SZ2, SCOZ2, SCONZ2Za2, SCSOZ2, SCSNZ2Za2, NZ2Za2, NZ2C(=NZa2)NZb2Zc2, NZ2SO2Za2, COZ2, COOZ2, CONZ2Za2, CSZ2, CSNZ2Za2, SO3Z, SO2NZ2Za2, SO2Z2, SiZ2Za2Zb2, Si(OZ2)(OZa2)OZb2, linear or branched and optionally saturated 1-20C alkyl, 4-15 membered optionally saturated ring (optionally containing at least one of O, N or S, optionally fused to another ring, which are optionally substituted by at least one OZ2, CF3, halogen or linear or branched and optionally saturated 1-20C alkyl, and optionally containing a carbonyl or thiocarbonyl functional group); Z2, Za2, Zb2, Zc2H, linear or branched and optionally saturated 1-20C alkyl (optionally substituted by at least one Z3) or 4-15 membered optionally saturated ring (optionally containing at least one of O, N or S, optionally fused to another ring, which are optionally substituted by at least one Z3); Z3Z4, linear or branched and optionally saturated 1-20C alkyl (optionally substituted by at least one Z4), 4 - 15 membered optionally saturated ring (optionally containing at least one of O, N or S, optionally fused to another ring, which are optionally substituted by at least one Z4); Z4F, Cl, Br, CF3, OCF3, CN, NO2, OZ5, OCOZ5, OCONZ5Za5, SZ5, SCOZ5, SCONZ5Za5, SCSOZ5, SCSNZ5Za5, NZ5Za5, NZ5COZa5, NZ5CONZa5Zb5, NZ5C(=NZa5)NZb5Zc5, NZ5SO5Za5, COZ5, COOZ5, CONZ5Za5, CSZ5, CSNZ5Za5, SO3Z, SO2NZ5Za5, SO2Z5, SiZ5Za5Zb5 or Si(OZ5)(OZa5)OZb5; Z5, Za5, Zb5 and Zc5H, linear or branched and optionally saturated 1-20C alkyl, 4 - 15 membered optionally saturated ring (optionally containing at least one of O, N or S, optionally fused to another ring, which are optionally substituted by at least one CF3, halogen or linear or branched and optionally saturated 1-20C alkyl), provided that when A5 is CH2, Z2 and Za2 are not H and Me. Independent claims are also included for: (1) a cosmetic or pharmaceutical composition comprising compound (I), and (2) a regime or regimen for improving the condition and/or the appearance of human keratinous fibers and/or the skin from where the fibers emerge which comprises topically applying compound (I). [Image] ACTIVITY : Endocrine-Gen. MECHANISM OF ACTION : Human type-1 15-hydroxyprostaglandin dehydrogenase (type-1 15-PGDH) inhibitor. In a test used for determining type-1 15-PGDH inhibition, Tris buffer (0.965 ml) was introduced into a cell of a spectrophotometer adjusted to a measuring wavelength of 340 nm. An enzymatic suspension (0.035 ml) of type-1 15-PGDH at 37[deg]C was introduced into the cell. 4-[5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-furyl]benzoic acid (Ia) was added. Results showed that (Ia) exhibited an IC50 value of 3 mu M.