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Fluoropyrrolidine amides as dipeptidyl peptidase IV inhibitors.

Bioorganic & medicinal chemistry letters (2004-02-26)
Charles G Caldwell, Ping Chen, Jiafang He, Emma R Parmee, Barbara Leiting, Frank Marsilio, Reshma A Patel, Joseph K Wu, George J Eiermann, Aleksandr Petrov, Huaibing He, Kathryn A Lyons, Nancy A Thornberry, Ann E Weber
ABSTRACT

Amides derived from fluorinated pyrrolidines and 4-substituted cyclohexylglycine analogues have been prepared and evaluated as inhibitors of dipeptidyl dipeptidase IV (DP-IV). Analogues which incorporated (S)-3-fluoropyrrolidine showed good selectivity for DP-IV over quiescent cell proline dipeptidase (QPP). Compound 48 had good pharmacokinetic properties and was orally active in an oral glucose tolerance test in lean mice.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(S)-(+)-3-Fluoropyrrolidine hydrochloride, 97%
Sigma-Aldrich
(R)-(−)-3-Fluoropyrrolidine hydrochloride, 97%