Bicyclic 1-oxa-beta-lactam compounds, their preparation and pharmaceutical formulations containing them.

摘要

Bicyclic 1-oxa-β-lactam diacid antibiotics are described. They are represented by the formula
<Chemistry id="chema01" num="0001"><Image id="ia01" he="25" wi="75" file="IMGA0001.TIF" imgContent="chem" imgFormat="TIFF" inline="no" /></Chemistry>wherein R is an a-carboxysubstituted arylmethyl group of the formula
<Chemistry id="chema02" num="0002"><Image id="ia02" he="15" wi="41" file="IMGA0002.TIF" imgContent="chem" imgFormat="TIFF" inline="no" /></Chemistry>wherein R' is hydrogen, hydroxy, protected hydroxy, acetoxy, C<Sub>1</Sub>-C<Sub>3</Sub> alkyl, or halogen;
<Chemistry id="chema03" num="0003"><Image id="ia03" he="16" wi="85" file="IMGA0003.TIF" imgContent="chem" imgFormat="TIFF" inline="no" /></Chemistry><UnorderedLists id="ula01" listStyle="none"><ListItem>R° is hydrogen or methoxy;</ListItem><ListItem>R<Sub>1</Sub> and R,' are hydrogen or a carboxy protecting group; and when R<Sub>1</Sub> and R<Sub>1</Sub>' are hydrogen, the pharmaceutically acceptable salts thereof.</ListItem></UnorderedLists>

The compounds are prepared by reacting the corresponding 3-halomethyl diester with 1-cyanomethyl-1H-tetrazole-5-thiol followed by deesterification.