6-(Nitrogen-containing heterocyclic)hydroxymethylpenicillanic acids, compounds related thereto and processes for their preparation
AssigneeSchering Corporation
InventorsPatricia L. Cavender, Ashit K. Ganguly, Viyyoor M. Girijavallabhan
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Abstract
6-(Heterocyclic)hydroxymethylpenicillanic acids and compounds related thereto are prepared by reaction of a 6,6-dihalopenicillanic acid with a Grignard reagent and a heterocyclic aldehyde in an anhydrous aprotic solvent. The compounds possess useful antibacterial activity.
Claims18
A compound of the formula ##STR10## wherein R.sub.1 is a nitrogen-containing heterocyclic group selected from the group consisting of pyridyl, quinolinyl, pyrrolyl, indolyl, lower alkyl derivatives thereof;
- X is hydrogen, bromo, chloro or iodo;
- and
- the wavy lines denote the alternate .alpha. and .beta. sterechemical configurations.
A process for preparing compounds of the formula ##STR11## wherein R.sub.3 is a heterocyclic group containing one or more nitrogen, sulfur or oxygen atoms selected from the group consisting of pyridyl, quinolinyl, pyrrolyl, indolyl, thienyl, furanyl, and lower alkyl derivatives thereof;
- X is hydrogen, bromo, chloro or iodo;
- and
- the wavy lines denote the alternate .alpha. and .beta. stereochemical configurations;
- which comprises reacting a 6,6-dihalopenam of the formula ##STR12## wherein X' and X" are independently chloro, bromo or iodo, with a Grignard reagent and a heterocyclic aldehyde of the formula ##STR13## wherein R.sub.3 is as hereinabove defined in an anhydrous aprotic solvent at temperatures of -78.degree. to 0.degree. C.
Dependencies are inferred from the claim text.