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    • 1. 发明专利
    • NOVEL THIOPHENYLGLYCOSIDE DERIVATIVES, METHODS FOR PRODUCTION THEREOF, MEDICAMENTS COMPRISING SAID COMPOUNDS AND USE THEREOF
    • MEP60708A
    • 2011-05-10
    • MEP60708
    • 2003-06-27
    • SANOFI AVENTIS DEUTSCHLAND
    • GLOMBIK HEINERFRICK WENDELINHEUER HUBERTKRAMER WERNERBRUMMERHOP HARMPLETTENBURG OLIVER
    • C07H7/00A61K31/7042A61K31/7048A61P3/04A61P3/10A61P7/00A61P7/02A61P9/08A61P9/10A61P11/06A61P13/12A61P17/06A61P19/10A61P25/00A61P25/18A61P25/28A61P27/02A61P29/00A61P31/00A61P31/18A61P35/00A61P37/02C07H17/00
    • Thienyl-glycoside compounds (I) are new. Thienyl-glycoside compounds of formula (I) and their salts are new. [Image] R 1, R 2H, halo, OH, NO 2, CN, COOH, COT', COOT', CONH 2, CONHT', CONT' 2, T', 2-6C alkenyl, 2-6C alkynyl, OT', -T'-OH, -T'-OT', Ph,CH 2Ph, (1-4C) alkylcarbonyl (optionally substituted (os) by one or more F), SO 2NH 2, SO 2NHT, SO 2NT 2, ST, S(CH 2) pPh', SOT, SO(CH 2) pPh', SO 2T, SO 2(CH 2) pPh', NH 2, NHT, NT 2, 1-7C acylamino, Ph'' or -O(CH 2) pPh''; T : 1-6C alkyl; T' : 1-6C alkyl (os by one or more F); p : 0-6; Ph' : phenyl (os by 1 or 2 of F, Cl, Br, OH, CF 3, NO 2, CN, OCF 3, OT, T or NH 2); Ph'' : phenyl (os by 1-3 of halo, OH, CF 3, NO 2, CN, OCF 3, OT, T, NH 2, NHT, NT 2, SO 2Me, COOH, COOT or CONH 2); A : direct bond or 1-15C alkanediyl (optionally having one or more C-atom(s) replaced by O, CO, CH=CH, CC, S, CH(OH), CHF, SO, SO 2, N(T), N(-T-Ph) or NH); n : 0-4; Cyc 1>3-7 membered saturated, partially unsaturated or unsaturated ring, optionally having one C-atom replaced by O or S; R 3 - R 5H, halo, OH, NO 2, CN, COOH, COOT', (1-4C) alkylcarbonyl (os by one or more F), CONH 2, CONHT', CONT' 2, T', 2-6C alkenyl, 2-6C alkynyl, 1-12C alkoxy (os by one or more F), -T'-OH, -T'-OT', Ph,CH 2Ph, SO 2NH 2, SO 2NHT, SO 2NT 2, ST, S(CH 2) pPh', SOT, SO(CH 2) pPh', SO 2T, SO 2(CH 2) pPh', NH 2, NHT, NT 2, 1-7C acylamino, Ph'', -(CH 2) pPh'' or -O(CH 2) pPh''; or R 3 + R 4group completing a 5-7 membered saturated, partially unsaturated or unsaturated ring (Cyc 2>), optionally having 1 or 2 C-atom(s) replaced by N, O or S and os by T, 2-5C alkenyl or 2-5C (all optionally having one CH 2 replaced by O) or by F, Cl, OH, CF 3, NO 2, CN, (1-4C) alkoxycarbonyl, CONH 2, (1-4C) alkylaminocarbonyl or OCF 3; and provided that when R 3 and R 4 form a ring, R 5 is H. ACTIVITY : Antidiabetic; nephrotropic; ophthalmological; neuroprotective; anorectic; cardiant; vasotropic; thrombolytic; anticoagulant; antiarteriosclerotic; antiinflammatory; immunosuppressive; anti-HIV; antiasthmatic; osteopathic; cytostatic; antipsoriatic; nootropic; neuroleptic; antibacterial. MECHANISM OF ACTION : Glucose transport regulator. In a glucose transport assay in rabbit renal cortex 'Burstensaum' membrane vesicles, 2-hydroxymethyl-6-(2-(2-(4-chlorophenyl)-ethyl)-thien-3-yloxy)-tetrahydropyran-3,4,5-triol (Ia) (in beta -D-gluco form) had IC 2 5 0.9 MicroM.