Preparation of substituted pyrrolo[2,3-c]pyridine-2-carboxamides and thieno[2,3-c]pyridine-2-carboxamides as AMPK inhibitors.

The 5'-AMP-activated protein kinase AMPK functions as a master switch to maintain cellular and whole-body energy homeostasis and abnormal activity profiles of AMPK may cause pathol. disorders. The present invention relates to a series of compds. I [R1 = H, halo or 5-, 6-, 9- or 10-membered aryl or heteroaryl, wherein the heteroatom of said heteroaryl nos. 1, 2 or 3 and is independently selected from N, S or O; R2 = H or alkyl; R3 = alkyl, cycloalkyl or a 5-6 membered aryl or heteroaryl, wherein the heteroatom of said heteroaryl nos. 1, 2 or 3 and is independently selected from N, S or O; X = NMe, NEt or S; Z = H, (CH2)nU or (CH2)NH(CH2)nU (wherein n = 1-3 and U = H, NH2, NHMe, etc.); W = CH2, NH, O, S or a bond; with the provisos], useful as AMPK inhibitors. E.g., a multi-step synthesis of II, starting from 3-amino-4-chloropyridine and Et pyruvate, was described. Exemplified compds. I were evaluated in AMPK assays (data given). [on SciFinder(R)]