7-phenyl-substituted tetracycline compounds
AssigneeTrustees of Tufts College
InventorsMark L. Nelson, Mohamed Y. Ismail
Life of this patent
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Abstract
7-phenyl-substituted tetracycline compounds which are substantially free of positional isomers, methods of treating tetracycline responsive states, and pharmaceutical compositions containing the 7-phenyl-substituted tetracycline compounds are described. 7-substituted tetracycline compounds which are substantially free of positional isomers, methods of treating tetracycline responsive states, and pharmaceutical compositions containing the 7-substituted tetracycline compounds are described.
Claims15
A method for preparing a 7-substituted tetracycline compound substantially free of positional isomers, comprising:
- (a) reacting an unsubstituted tetracycline compound with at least one equivalent of N-iodosuccinimide in trifluoroacetic acid to result in a 7-iodo tetracycline compound substantially free of positional isomers;
- (b) reacting the 7-iodo tetracycline compound substantially free of positional isomers with a boronic acid, a palladium catalyst and aqueous sodium carbonate in a solvent;
- and
- (c) purifying the resultant solution from step (b).
A method for preparing a 7-substituted tetracycline compound substantially free of positional isomers, comprising:
- (a) reacting an unsubstituted tetracycline compound with at least one equivalent of N-iodosuccinimide in trifluoroacetic acid to result in a 7-iodo tetracycline compound substantially free of positional isomers;
- (b) reacting the 7-iodo tetracycline compound substantially free of positional isomers with a tin reagent, a palladium catalyst and, optionally, copper iodide;
- and
- (c) purifying the resultant solution from step (b).
Dependencies are inferred from the claim text.