Abbott Laboratories Corporation

Jih-Hua Liu

David A Riley

Stephen H Montgomery

Hing L Sham

Dale J Kempf

Daniel W Norbeck

Xiaoqi Chen

David A Betebenner

Daniel A Dickman

Lawrence Kolaczkowski

Daniel J Plata

Steven M Hannick

Thomas R Herrin

Ketan M Patel

Eric J Stoner

Stephen L Condon

Arthur J Cooper

Patricia A Oliver

Jieh-Heh J Tien

Gondi N Kumar

Peter J Stengel

Rodger F Henry

Stephen G Spanton

George A Foster, Jr

Yi-Yin Ku

Joseph E Celebuski

Hemantkumar H Patel

Chengxi Yang

H Eugene Gracey

Steven G Spanton

A compound of the formula: is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.

Retroviral protease inhibiting compounds

A procedure for preparing 6-O-alkyl erythromycin compounds having the formula:wherein Ris a loweralkyl group, Rand Ran independently hydrogen or a hydroxy-protecting group, except that Rand Rmay not both be hydrogen simultaneously; Y is oxygen or a specifically substituted oxime; and Z is hydrogen, hydroxy or protected-hydroxy; by reaction of the compound wherein Ris hydrogen with an alkylating reagent, is the presence of a strong alkali metal base and also in the presence of a weak organic amino base, in a suitable stirred or agitated polar aprotic solvent, or a mixture of such polar aprotic solvents maintained at a reaction temperature and for a period of time sufficient to effect alkyation.

Process for 6-O-alkylation of erythromycin derivatives

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

A process of preparing a 6-O-alkyl derivative of 9-oxime erythromycin B is provided. Intermediates used in the preparation of a 6-O-alkyl 9-oxime erythromycin B are also provided. Pharmaceutical compositions containing a 6-O-alkyl derivative of 9-oxime erythromycin B and the use of those compositions to treat bacterial infections are also provided.

6-O-aklyl erythromycin B oxime

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

Process for preparing 6-O-alkyl-9-oxime erythromycin B

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

A procedure for preparing 6-O-alkyl erythromycin compounds having the formula: ##STR1## wherein R.sup.1 is a loweralkyl group, R.sup.2 and R.sup.3 are independently hydrogen or a hydroxy-protecting group, except that R.sup.2 and R.sup.3 may not both be hydrogen simultaneously; Y is oxygen or a specifically substituted oxime; and Z is hydrogen, hydroxy or protected-hydroxy; by reaction of the compound wherein R.sup.1 is hydrogen with an alkylating reagent, in the presence of a strong alkali metal base and also in the presence of a weak organic amine base, in a suitable stirred or agitated polar aprotic solvent, or a mixture of such polar aprotic solvents maintained at a reaction temperature and for a period of time sufficient to effect alkyation.

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

An antibacterial compound is disclosed having the formula: ##STR1## wherein R.sub.1 is loweralkyl or a pharmaceutically acceptable salt, ester or prodrug thereof, processes and intermediates useful in the preparation of the above compounds, as well as compositions containing the same and methods for their use.

6-O-methyl erythromycin D and process for making

A process of preparing a 6-O-methyl erythromycin A derivative using a 2'-protected, 9-etheroxime erythromycin A intermediate is provided. A preferred protecting group for the 2'-position is acetyl. 2'-protected, 9-etheroxime erythromycin A derivatives are also provided. Also disclosed is a method for inhibiting quaternary salt formation at the 3' amine without the need for 3'N-protecting groups.

Growing community of inventors

Green Oaks, IL, United States of America

Jih-Hua Liu