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.
Claims8
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;
- further protecting by converting said protected glycoside to a acetonide using a ketal or ketone;
- converting said acetonide to an alkoxide and reacting with an alkylating agent to form an ether;
- converting said ether to a diol having protecting two protecting groups;
- further protecting said dial using selective etherification to form a triprotected arabinose derivative;
- converting said arabinose derivative to a triprotected xylose derivative using an activated system;
- converting said xylose derivative to a triprotected nitrile using an activated system;
- converting said nitrile using catalytic hydrogenation.
A method for preparing isofagomine, its derivatives, or acid salts thereof, comprising contacting L-(−)-xylose with an alcohol, an activating agent and optionally a solvent to form a protected glycoside;
- converting said glycoside to a triprotected xylose derivative;
- converting said xylose derivative to a triprotected nitrile;
- converting said nitrile to a protected dial and deprotecting said dial.
A compound of the formula
A compound selected from the group consisting of
Dependencies are inferred from the claim text.