C-aryl glucoside SGLT2 inhibitors and method

US6414126B1 · kind B1 · utility

Assignee

• Bristol-Myers Squibb Company · US

Inventors

• Bruce A. Ellsworth · Princeton, US
• William N. Washburn · Titusville, US
• Philip M. Sher · Plainsboro, US
• Gang Wu · Zhejiang, CN
• Wei Meng · Pennington, US

Key dates

• Filing date: Oct 4, 2000
• Grant date: Jul 2, 2002
• Expiry date: Oct 4, 2020

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C49/84
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

SGLT2 inhibiting compounds are provided having the formula whereR1, R2, and R2a are independently hydrogen, OH, OR5, lower alkyl, CF3, OCHF2, OCF3, SR5i or halogen, or two of R1, R2 and R2a together with the carbons to which they are attached can form an annelated five, six or seven membered carbocycle or heterocycle;R3 and R4 are independently hydrogen, OH, OR5a, OAryl, OCH2Aryl, lower alkyl, cycloalkyl, CF3, —OCHF2, —OCF3, halogen, —CN, —CO2R5b, —CO2H, —COR6b, —CH(OH)R6c, —CH(OR5h)R6d, —CONR6R6a, —NHCOR5c, —NHSO2R5d, —NHSO2Aryl, Aryl, —SR5e, —SOR5f, —SO2R5g, —SO2Aryl, or a five, six or seven membered heterocycle, or R3 and R4 together with the carbons to which they are attached form an annelated five, six or seven membered carbocycle or heterocycle;R5, R5a, R5b, R5c, R5d, R5e, R5f, R5g, R5h and R5i are independently lower alkyl;R6, R6a, R6b, R6c and R6d are independently hydrogen, alkyl,aryl, alkylaryl or cycloalkyl, or R6 and R6a together with the nitrogen to which they are attached form an annelated five, six or seven membered heterocycle;A is O, S, NH, or (CH2)n where n is 0-3.A met…