SYNTHESIS AND ANTICHOLINERGIC ACTIVITY OF THE 4 STEREOISOMERS OF -(DIMETHYLAMINO)-2-PHENYL-2-(2-PYRIDYL)PENTANAMIDE

The four stereoisomers of 4-(dimethylamino)-2-phenyl-(2-pyridyl)pentan amide were synthesized, and the absolute configurations were determine d by X-ray crystallography. Pharmacological testing for anticholinergi c activity revealed great differences in potency among 10 (2R,4R, IC50 = 0.40 mu M), 11 (2S,4S, 31 mu M), 12 (2R,4S, 170 mu M), and 13 (2S,4 R, 0.13 mu M). A new drug application for the racemate 8 (FK176, vamic amide) has been filed in Japan for the treatment of overactive detruso r syndrome.