DERIVATIVES OF ARYL-5-THIO-β-D-GLYCOPYRANOSIDE AND THERAPEUTIC AGENT COMPRISING THEREOF USED IN DIABETES MELLITUS Russian patent published in 2008 - IPC C07H15/203 A61K31/7034 A61P3/10 

FIELD: organic chemistry, medicine, endocrinology, pharmacy.

SUBSTANCE: invention relates to a derivative of 5-thio-β-D-glucopyranoside of the formula (i): wherein Y represents -O- or -NH-; R², R² or R³ represents hydrogen atom, acyl or phenyl-(C₁-C₄)-alkyl; R⁴ represents hydrogen atom, acyl, alkoxycarbonyl or phenyl-(C₁-C₄)-alkyl; Ar represents phenyl or naphthyl substituted with -X-A¹, and phenyl can be substituted additionally with 1-3 similar or different substitutes chosen from halogen atom, hydroxyl and others; X represents -(CH₂)_n-, -CO(CH₂)_n-, -CH(OH)(CH₂)_n-, -O-(CH₂)_n-, -CONH(CH₂)_n- wherein n means a whole number from 0 to 3, -COCH=CH-, -S- or -NH-; A¹ represents phenyl, naphthyl or heteroaryl chosen from benzofuranyl group, pyridyl group, pyrazolyl group and thiazolyl group wherein three latter groups can be substituted additionally with alkyl, and phenyl group can be substituted with 1-4 similar or different substitutes chosen from halogen atom, hydroxyl and others; or its pharmaceutically acceptable salt or its hydrate. Derivatives of the formula (i) possess inhibitory effect with respect to SGLT2 activity. Also, invention relates to a pharmaceutical composition representing prophylactic or therapeutic agent used in diabetes mellitus, diseases or complications associated with diabetes mellitus. Also, invention relates to a derivative of 5-thio-β-D-glucopyranoside of the formula (III): wherein R²¹, R²², R²³ and R²⁴ means hydrogen atom or acyl; R²⁵ means amino group, alkanoyl, carboxyl or alkoxycarbonyl; R²⁶ means hydrogen atom or hydroxy group; R²⁷ means hydrogen atom or alkyl; or to its pharmaceutically acceptable salt or hydrate. Derivatives of the formula (III) are intermediate compound used in synthesis of compounds of the formula (I): wherein Y means -O-; each among R¹, R² or R³ represents hydrogen atom, acyl or phenyl-(C₁-C₄)-alkyl; R⁴ represents hydrogen atom, acyl, alkoxycarbonyl or phenyl-(C₁-C₄)-alkyl; one radical among R⁵, R⁶, R⁷, R⁸ and R⁹ represents -X-A¹ (wherein X and A¹ have values given above), and others represent hydrogen atom, halogen atom and others.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

17 cl, 4 sch, 1 tbl, 30 ex