Beta-lactam antibiotics

US4200576A · kind A · utility

Assignee

• BAYER HEALTHCARE LLC · DE

Inventors

• Peter Feyen · Mettmann, DE
• Michael Preiss · Leinfelden, DE
• Karl G. Metzger · Wuppertal, DE

Key dates

• Filing date: Dec 20, 1977
• Grant date: Apr 29, 1980
• Expiry date: Dec 20, 1997

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Antibacterially active and animal feedstuff supplement .beta.-lactam antibiotics of the formula ##STR1## in which R is H or --UR', PA1 U is O or S, PA1 R' is optionally substituted alkyl, alkenyl, alkinyl, aralkyl, aryl or cycloalkyl, PA1 Z is ##STR2## R.sup.1 and R.sup.2 individually are hydrogen or, individually or together with the carbon atom to which they are bonded, are any of various radicals, PA1 A is --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 -- or ##STR3## B is optionally substituted phenyl or is cyclohexenyl or cyclohexadienyl; X is S, O, SO, SO.sub.2 or --CH.sub.2 --; and PA1 Y is a group of the formula ##STR4## T is hydrogen, alkyl--CO--O--, pyridinium, aminopyridinium, carbamoyloxy, azido, cyano, hydroxyl or optionally substituted --S--phenyl, or is --S--Het, PA1 in which PA2 Het is an optionally substituted heterocyclic 5-membered or 6-membered ring; PA1 and wherein PA2 E is hydrogen, a radical forming, with the carboxyl group to which it is attached, a carboxy ester group, a cation of a salt, or a protective group, or a hydrate thereof. A process is also given for converting R directly from H to UR' employing a base, a halogenating agent and R'UH .