Antidiabetic agents

US7169806B2 · kind B2 · utility

Assignee

• Ferring B.V. · NL

Inventor

• David Michael Evans · Royston, GB

Key dates

• Filing date: Apr 15, 2005
• Grant date: Jan 30, 2007
• Expiry date: Apr 15, 2025

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D207/16
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Compounds which are 1-(2′-aminoacyl)-2-cyanopyrrolidine derivatives according to general formula (1) are DP-IV inhibitors for treatment of impaired glucose tolerance or type 2 diabetes; wherein A is selected from groups (2, 3 and 4); X is selected from aminoacyl groups corresponding to the natural amino acids, acyl groups R3CO, groups R4COOC(R5)(R6)OCO, methoxycarbonyl, ethoxycarbonyl and benzyloxycarbonyl; R1 is selected from H, C1–C6alkyl residues, (CH2)aNHW1, (CH2)bCOW2, (CH2)cOW3, CH(Me)OW4, (CH2)d—C6H4—W5 and (CH2)eSW6, where a is 2–5, b is 1–4, c is 1–2, d is 1–2, e is 1–3, W1 is COW6, CO2W6 or SO2W6, W2 is OH, NH2, OW6 or NHW6, W3 is H or W6, W4 is H or W6, W5 is H, OH or OMe, and W6 is C1–C6 alkyl, optionally substituted phenyl, optionally substituted heteroaryl or benzyl and R2 is selected from H and (CH2)n—C5H3N—Y, where n is 2–4 and Y is H, F, Cl, NO2 or CN, or R1 and R2 together are —(CH2)p— where p is 3 or 4; R3 is selected from H, C1–C6 alkyl and phenyl; R4 is selected from H, C1–C6 alkyl, benzyl and optionally substitued phenyl; R5 and R6 are each independently selected from H and C1–C6 alkyl or together are —(CH2)m—, where m is 4–6; R7 is selected from pyridyl and o…