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

US5962697A · kind A · utility

Assignee

• Pharmacia & Upjohn Company LLC · US

Inventors

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

Key dates

• Filing date: Jul 24, 1997
• Grant date: Oct 5, 1999
• Expiry date: Jul 24, 2017

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D207/16
• 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 figure BG.sub.4-1, below. ##STR1## 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; PA1 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, …