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US 2008/0177055 A1Published application
Methods for preparing 2-alkynyladenosine deriviatives
AssigneePGx Health, LLC
InventorsIain F. Pickersgill, Edward H. Cheesman
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Abstract
Disclosed are methods for preparing 2-alkynyladenosine derivatives of formula A: or a stereoisomer, pharmaceutically acceptable salt, hydrate, solvate, acid salt hydrate or isomorphic crystalline form thereof, the method comprising the step of: contacting 2-iodoadenosine-5′-N-ethyluronamide with a compound of formula B: wherein Z is —C(═O)OR or —CH2C(═O)R, where R is a C1 to C5 alkyl, preferably The methods are useful for preparing 2-alkynyladenosine derivatives that are, in certain embodiments, adenosine receptor agonists.
Claims11
A method for preparing a compound of formula A:
- or a stereoisomer, pharmaceutically acceptable salt, hydrate, solvate, acid salt hydrate or isomorphic crystalline form thereof, the method comprising the step of:
- (1) providing 2-iodoadenosine;
- (2) protecting the hydroxyl groups of said 2-iodoadenosine with an acetonide group;
- (3) oxidizing, via radical oxidation, the primary alcohol of said acetonide-protected 2-iodoadenosine to an acid derivative of said acetonide-protected 2-iodoadenosine;
- (4) converting said acid derivative to an N-ethylamide derivative of said acetonide-protected 2-iodoadenosine;
- (5) deprotecting said N-ethylamide of said acetonide-protected 2-iodoadenosine to form said 2-iodoadenosine-5′-N-ethyluronamide;
- and
- (6) contacting said 2-iodoadenosine-5′-N-ethyluronamide with a compound of formula B:
- wherein
- Z is —C(═O)OR or —CH2C(═O)R, where R is a C1 to C5 alkyl.
7 more elements
Dependencies are inferred from the claim text.