Eli Lilly and Company

James M Greene

Gregory Alan Stephenson

Holly M Hankins

Edward C Taylor

Edward R Lavagnino

Charles A Bunnell

David D Wirth

Andrew J Pike

Gary D Zintgraff

Sigmund A Schildcrout

Jane A Goedde

The invention provides Form II dirithromycin, a novel polymorph of dirithromycin. Also disclosed are the acetone, 1-butanol, 1-propanol, and 2-propanol solvates of dirithromycin, which provide an efficient means for preparing and isolating Form II. Processes for preparing and isolating Form II dirithromycin from these solvates or from Form I dirithromycin are provided. A process for obtaining Form II dirithromycin from non-solvated dirithromycin is also provided. Another aspect of the invention is an improved tablet containing Form II dirithromycin as the active ingredient.

Process for preparing crystal forms and solvates of dirithromycin

Form II Dirithromycin

The present invention provides a process for preparing alkylsulfinyl 2-phenylimidazo[4,5-c]pyridines comprising reacting an N-(3-amino-4-pyridinyl)alkylthiobenzamide with an oxidizing agent in a lower alkanoic acid solvent.

Synthesis of alkylsulfinyl substituted 2-phenylimidazo(4,5-c)pyridines

The present invention relates to a process for preparing aminonitropyridines comprising reacting an alkoxynitropyridine with ammonium acetate.

Process for the synthesis of intermediates in the preparation of

Hydroxyphenylacetic acids are formed from the corresponding benzaldehydes or alkyl phenyl ketones by reduction, cyanation and hydrolysis without isolation or purification of intermediate products.

Process for preparing phenylalkanoic acids

A process for preparing certain substituted benzyl esters of phenylacetic acids by esterification in a solvent in which the salt of the acid is insoluble, and in the presence of a phase transfer catalyst.

Synthesis of substituted benzyl esters

An aqueous solution of sodium or potassium 2-ethylhexanoate is spray dried in a spray drier having an inlet temperature ranging from about 100.degree. C. to about 160.degree. C. and an outlet temperature ranging from 60.degree. C. to about 130.degree. C. to provide the corresponding sodium or potassium 2-ethylhexanoate having a moisture content of from about 0.5 to about 5.0 percent by weight and having improved purity and crystalline texture.

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Indianapolis, IN, United States of America

James M Greene