Abbott Laboratories Corporation

Stephen H Montgomery

Jih-Hua Liu

George A Foster, Jr

David A Riley

H Eugene Gracey

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

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

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.

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Vernon Hills, IL, United States of America

Stephen H Montgomery