Schering Corporation

John K Jenkins

Mahesh G Patel

John S Chiu

Paul E McNamara

Min Chu

Charles G Eckhart

Stanley Rosenhouse

Ronald A Mierzwa

Richard E Youngstrom

Alan J Miller

Process for preparing a lipophilic oligosaccharide antibiotic containing a nitro group using oxidizing agents and catalysts such as cobalt, manganese and copper having an oxidation state of +2 are disclosed.

Process for preparing lipophilic oligosaccharide antibiotics

Orthosomycins have been isolated from the fermentation broth of the microorganism Micromonospora Carbonacea var Africana designated SCC 2146. These compounds are antibacterial agents. Compositions and methods for treating bacterial infections are also described.

Orthosomycins from micromonospora carbonacae

A novel, stable, crystalline sodium (5R,6S,8R)-6-(1-hydroxyethyl)-2-(2-carbamoyloxyethylthio)-penem-3-carboxyl ate (designated as Form II) is prepared by forming a homogenous solution of sodium (5R,6S,8R)-6-(1-hydroxyethyl)-2-(2-carbamoyloxyethylthio)-penem-3-carboxyl ate combined with stirring the homogenous solution for a time and at a temperature sufficient to produce Form II and recovering Form II. Form II may also be prepared by contacting a first solution obtained by dissolving (5R,6S,8R)-6-(1-hydroxyethyl)-2-(2-carbamoyloxyethylthio)-penem-3-carboxyl ic acid in dimethylacetamide with a second solution obtained by dissolving a sodium salt of an organic acid having a pKa of up to about 5, e.g., sodium 2-ethylhexanoate in acetone, in the presence of at least 5 volume percent water while stirring the reaction mixture so formed at a temperature and for a time sufficient to produce Form II followed by recovering Form II. Form II exhibits a greater physical stability and increased solid state chemical stability and reduced hygroscopicity over that of the amorphous form (e.g., Form I) which renders Form II greatly superior to Form I as a clinically suitable antibacterial agent.

Crystalline sodium (5R, 6S,

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Chatham, NJ, United States of America

John K Jenkins