Abbott Laboratories Corporation

Mediver Ab

David A Riley

Jih-Hua Liu

Yi-Yin Ku

Jien-Heh J Tien

Ashok V Bhatia

Rodger F Henry

Howard E Morton

Paul A Lartey

Steven A Chamberlin

Michael Rasmussen

William Rosenbrook, Jr

Elaine C Lee

Stephen G Spanton

Anthony Ralph Haight

James J Napier

Steven J Wittenberger

Kirill A Lukin

Lawrence Kolaczkowski

Steven A King

M Robert Leanna

Russell Drew Cink

Sou-Jen Chang

David R Hill

Steven M Hannick

Daniel J Plata

Marvin Robert Leanna

Bikshandarkoil A Narayanan

Albert V Thomas

Arthur J Cooper

Margaret Chi-Ping Hsu

Eric J Stoner

John J Hufnagel

Bradley D Gates

Bhadra Shelat

Lakshmi Bhagavatula

Maureen Ann McLaughlin

Stephen H Montgomery

Pulla Reddy Singam

Shyamal I Parekh

Zhenping Tian

Tim Grieme

Prasad S Raje

Weijiang Zhang

Ramesh R Patel

Alexandra E Graham

Cynthia B Curty

Mahendra N Deshpande

John Bellettini

Tiffany Spitz

Gregg E Robinson

Matthew John Peterson

Greg Lannoye

Greg Wayne

Daniel Plata

Cheng-Xi Yang

Michael John Dipierro

H Eugene Gracey

Greg E Robinson

Steven G Spanton

The present invention relates to a novel 6-O-methylerythromycin A crystal form, a process for preparing the crystal form, and methods for using the crystal form to prepare a 6-O-methylerythromycin A crystal form II.

6-O-methylerythromycin A crystal form III

In one aspect, the invention relates to a process for preparing 6-O-substituted erythromycin derivatives comprising reacting 2&prime;-substituted and optionally 4&Prime;-substituted 9-oxime erythromycin derivatives with an alkylating agent in the presence of a palladium catalyst and phosphine. In another aspect, the invention relates to processes for preparing 6-O-substituted erythromycin ketolides using the palladium-catalyzed alkylation reaction.

Process for preparing 6-o-substituted erythromycin derivatives

Methods and novel intermediates of the formula:

Synthesis of acyclic nucleoside derivatives

The present invention concerns the novel antiobiotic 6-O-methylerythromycin A form O solvate, a process for its preparation, pharmaceutical compositions comprising this compound and a method of use as a therapeutic agent.

Crystal form O of clarithromycin

A method for the preparation of D-chiro-inositol from kasugamycin, comprising the steps of: (a) reacting kasugamycin with an acetylating agent to form a crude hexa-acetate intermediate; (b) purifying the crude intermediate to form purified hexa-acetate intermediate; (c) deacetylating the purified intermediate to form D-chiro-inositol; and (d) isolating the D-chiro-inositol. The method permits efficient, large-scale preparation of D-chiro-inositol without the need for extensive chromatographic purification of the final D-chiro-inositol product.

Processes for the preparation of D-chiro-inositol

Novel 6-O-alkyl derivatives of erythronolide B are provided. A process for the preparation of 6-O-alkyl derivatives of erythronolide B using erythromycin B is also provided. A process for preparing 6-O-alkyl derivatives of erythromycin C using novel 6-O-alkyl derivatives of erythronolide B is further provided.

6-O-alkyl derivatives of erythronolide B

Polymers can be prepared in solution by continuously distilling solvent from a solution of diacid prepolymers.

Process for the preparation of polyanhydrides

The claimed invention provides a novel method of preparing 6-O-methyl erythromycin A. The process comprises the steps of reducing the 9-keto group of erythromycin A to form a 9-hydroxy erythromycin A, protecting the 9-, 2'-, and/or 4'-hydroxyl groups of erythromycin A, selectively methylating the 6-position of the 9-hydroxy erythromycin A derivative, deprotecting the hydroxyl groups and oxidizing the 9-hydroxyl to afford 6-O-methyl erythromycin A.

Process for the preparation of 6-O-methyl erythromycin a using 9-hydroxy

The disclosed invention relates to novel 3'-N-O, 9-O-oxime protected, 6-O-alkyl erthyromycin derivatives, a process of preparing the same. The invention also relates to a process of preparing 6-O-alkyl erythromycin A by eliminating the 3'-N-oxide group and 9-O-oxime protecting groups and optionally deprotecting the hydroxy groups at the 2'- and 4'- positions under suitable reaction conditions.

3'-N'oxide, 3'-n-dimethylamine, 9-oxime erythromycin a derivatives

The present invention concerns the novel antiobiotic 6-O-methylerythromycin A crystal form I, a process for its preparation, pharmaceutical compositions comprising this compound and a method of use as a therapeutic agent.

Crystal form I of clarithromycin

The present invention provides a process for the preparation of 6-O-methylerythromycin A Form II comprising converting erythromycin A to 6-O-methylerythromycin A and treating the 6-O-methylerythromycin A with a number of common organic solvents or mixtures of common organic solvents.

Preparation of crystal form II of clarithromycin

A process for the preparation of 4'-deoxyerythromycins, having the formula: ##STR1## wherein R is H or OH, and R.sup.1 is H or loweralkyl by treatment of the 2'-O-acetyl-4'-imidazolylthionocarbonyl-erythromycin starting material with the radical initiator 4,4'-azobis-(4-cyanovaleric acid), H.sub.3 PO.sub.2 and an organic base in a water-miscible solvent and optionally eliminating the 2'-O-acetyl group. In a preferred embodiment, the water-miscible solvent is an alcohol and the deoxygenation and deacetylation is carried out in one step.

Process for preparation of 4'-deoxyerythromycins A and B

A method for the preparation of D-chiro-inositol from kasugamycin, comprising the steps of:

Method for the preparation of D-chiro-inositol

Aminodeoxy derivatives of 3-deoxy-D-manno-2-octulosonic acid (KDO) are potent inhibitors of bacterial enzymes and a novel class of antibacterial agents.

Amino D-manno-2-octulopyranosidonate containing compounds,

Derivatives of 3-deoxy-D-manno-2-octulosonic acid (KDO) are potent inhibitors of bacterial enzymes and a novel class of antibacterial agents.

D-manno-2-octulosonic acid derivatives, pharmaceutical compositions and

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Kenosha, WI, United States of America

David A Riley