Optically active 3-(1-(alkylamino))alkyl pyrrolidines

US5773610A · kind A · utility

Assignee

• Pharmacia & Upjohn Company LLC · US

Inventors

• William McWhorter · Parchment, US
• Thomas J. Fleck · Scotts, US
• Bruce Allen Pearlman · Kalamazoo, US

Key dates

• Filing date: Nov 1, 1995
• Grant date: Jun 30, 1998
• Expiry date: Nov 1, 2015

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D207/09
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

This invention relates to processes for the synthesis of various optically active amino pyrrolidinyl stereoisomers, or enantiomers, that may be attached to quinolonecarboxylic acids or naphthyridones. Processes and essential intermediates are disclosed and claimed for the synthesis of compounds represented by the structure shown in FIG. BG.sub.4-1, where R.sup.50, R.sup.6 and R.sup.9 are defined independently and are H, -(C.sub.1 -C.sub.8)alkyl, -(C.sub.3 -C.sub.8)cycloalkyl, -(C.sub.1 -C.sub.8)alkyl-(C.sub.3 -C.sub.8)cycloalkyl, -(C.sub.6 -C.sub.12 aryl), -(C.sub.1 -C.sub.8)alkyl-(C.sub.6 -C.sub.12 aryl), or the aryl or alkyl is substituted with one to three of the following groups, (C.sub.6 -C.sub.12 aryl), (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)alkoxy, halogen, trifluoromethyl; where R.sup.2 is -(C.sub.1 -C.sub.8)alkyl, -(C.sub.3 -C.sub.8)cycloalkyl, -(C.sub.1 -C.sub.8)alkyl-(C.sub.3 -C.sub.8)cycloalkyl, -(C.sub.6 -C.sub.12 aryl), -(C.sub.1 -C.sub.8)alkyl-(C.sub.6 -C.sub.12 aryl), or the aryl or alkyl is substituted with one to three of the following groups, -(C.sub.6 -C.sub.12 aryl), -(C.sub.1 -C.sub.3)alkyl,-(C.sub.1 -C.sub.3)alkoxy, halogen, trifluoromethyl; depending upo…