Journal of Medicinal Chemistry p. 4205 - 4213 (1992)
Update date:2022-07-30
Topics:
Cesare, P. Di
Bouzard, D.
Essiz, M.
Jacquet, J. P.
Ledoussal, B.
et al.
A series of novel 7-substituted-1-tert-butyl-6-fluoronaphthyridone-3-carboxylic acids has been prepared.These derivatives are characterized by chiral aminopyrrolidine substituents at the 7 position.In this paper we report the full details of the asymmetric synthesis of this series of compounds.Structure-activity relationship studies indicate that the absolute stereochemistry at the asymmetric centers of the pyrrolidine ring is critical for maintaining good activity.Compounds 60 and 61 (3-amino-4-methylpyrrolidine enantiomers) were selected for preclinical evaluation.
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