New method for preparing isofagomine and its derivatives
AssigneeAmicus Therapeutics, Inc.
InventorsPhilip Rybczynski, Alexander Tretyakov, Dan Fuerst, Kamlesh Sheth
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Abstract
A method for preparing isofagomine, its derivatives, intermediates and salts thereof using novel processes to make isofagomine from D-(−)-arabinose and L-(−)-xylose.
Claims11
A method for preparing isofagomine, its derivatives, or acid salts thereof, comprising protecting the anomeric hydroxyl group of D-(−)-arabinose with a protecting group to form a glycoside;
- protecting the 2- and 3-hydroxyl groups of said glycoside using a 1,2-dione to form a triprotected arabinose derivative;
- converting said arabinose derivative to a triprotected xylose derivative;
- converting said xylose derivative to a triprotected nitrile;
- converting said nitrile to a protected diol and deprotecting said diol.
A method for preparing isofagomine, its derivatives, or acid salts thereof, comprising protecting the anomeric hydroxyl group of D-(−)-arabinose with a protecting group to form a glycoside;
- protecting the 2- and 3-hydroxyl groups of said glycoside using a 1,2-dione to form a triprotected arabinose derivative;
- converting said arabinose derivative to a triprotected xylose derivative;
- converting said xylose derivative to a triprotected nitrile;
- converting said nitrile to a protected isofagomine salt and deprotecting said isofagomine salt.
A method for preparing isofagomine, its derivatives, or acid salts thereof, comprising protecting the anomeric hydroxyl group of D-(−)-arabinose with a protecting group to form a glycoside;
- protecting the 2- and 3-hydroxyl groups of said glycoside using a 1,2-dione to form a triprotected arabinose derivative;
- converting said arabinose derivative to a triprotected xylose derivative;
- converting said xylose derivative to a triprotected nitrile;
- reducing said nitrile to a triprotected primary amine;
- deprotecting said primary amine to a diol and using catalytic hydrogenation.
9-15. (canceled)
Dependencies are inferred from the claim text.