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US 6,228,882 B1Granted
Pyronin antibacterials, process and novel intermediates thereto
AssigneesAnadys Pharmaceuticals, Inc., Scriptgen Pharmaceuticals, Inc.
InventorsMark A. Wuonola, Gary R. Gustafson, James S. Panek, Tao Hu, Jennifer V. Schaus
Life of this patent
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Abstract
The present invention provides convergent processes for preparing myxopyronins and corallopyronins, compounds useful as antibacterial therapeutics. The present invention also provides novel compositions of matter which are useful for the preparation of pyronin antibiotics.
Claims10
A compound having the structure:
- wherein R is C1-9alkyl, and wherein R1 is H, C1-9alkyl, benzyl, optionally substituted phenyl, OH, NH2, alklamine, dialkylamine, or optionally substituted phenylamine.
A process of preparing a myxopyronin having the structure:
- wherein R is C1-9alkyl, and wherein R1 is NH2, alkylamine, dialkylamine, or optionally substituted phenylamine;
- which comprises:
- (a) saponifying a pyrone ketone having the structure:
- wherein R0 is C1-9alkyl;
- to form a pyrone acid;
- and
- (b) acylating the pyrone acid to form a pyrone anhydride;
- (c) reacting the pvrone anhydride formed in step (b) with an azide salt to form a pyrone acyl azide;
- and
- (d) reacting the pyrone acyl azide formed in step (c) with an ammonia, alkylamine, dialkylamine or optionally substituted phenvlamine to form the myxopyronin.
7 more elements
Dependencies are inferred from the claim text.