Substituted oxazine and thiazine oxazolidinone antimicrobials

US5688792A · kind A · utility

Assignee

• Pharmacia & Upjohn Company LLC · US

Inventors

• Michael R. Barbachyn · Kalamazoo, US
• Steven J. Brickner · Ledyard, US
• Douglas K. Hutchinson · Antioch, US

Key dates

• Filing date: Mar 5, 1996
• Grant date: Nov 18, 1997
• Expiry date: Mar 5, 2016

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D417/10
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A compound of structural Formula I: ##STR1## or pharmaceutically acceptable salts thereof wherein: X is O, S, SO, SO.sub.2, SNR.sup.10 or S(O)NR.sup.10 ; PA1 R is (a) hydrogen, PA2 (b) C.sub.1 -C.sub.8 alkyl optionally substituted with one or more of the following: F, Cl, hydroxy, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 acyloxy or --O--CH.sub.2 --Ph, PA2 (c) C.sub.3 -C.sub.6 cycloalkyl, PA2 (d) amino, PA2 (e) C.sub.1 -C.sub.8 alkylamino, PA2 (f) C.sub.1 -C.sub.8 dialkylamino or PA2 (g) C.sub.1 -C.sub.8 alkoxy; PA1 R.sup.1 is H, except when X is O then R.sup.1 can be H, CH.sub.3, CN, CO.sub.2 H, CO.sub.2 R or (CH.sub.2).sub.m R.sup.11 (m is 1 or 2); PA1 R.sup.2 is independently H, F or Cl; PA1 R.sup.3 is H except when X is O and R.sup.1 is CH.sub.3 then R.sup.3 can be H or CH.sub.3 ; PA1 R.sup.10 is independently H, C.sub.1 -C.sub.4 alkyl (optionally substituted with chloro, fluoro, hydroxy, C.sub.1 -C.sub.8 alkoxy, amino, C.sub.1 -C.sub.8 alkylamino, or C.sub.1 -C.sub.8 dialkylamino) or p-toluenesulfonyl; PA1 R.sup.11 is hydrogen, OH, OR, OCOR, NH.sub.2, NHCOR or N(R.sup.10).sub.2 ; and n is 0, 1 or 2. The oxazine and thiazine oxazolidinone derivatives are useful antimicrobial ag…