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US 10,457,623 B1Granted
Process for the preparation of Lubiprostone and intermediates thereof
AssigneeChirogate International Inc.
InventorsShih-Yi Wei, Min-Kuan Hsu
Life of this patent
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Abstract
The present invention relates to a novel process for preparing Lubiprostone and novel intermediates prepared from the process. The process of the present invention does not generate hydrogenated by-products that are difficult to be removed, and thus enables the production of Lubiprostone in an efficient and economical way.
Claims2
A process for preparing Lubiprostone, comprising the steps of:
- (1) coupling a cyclopentenone of Formula 1:
- wherein R1 is C1-7-alkyl, aryl or aralkyl, each of which is unsubstituted or substituted by C1-4-alkyl, nitro, halogen or alkoxy;
- and P1 is a protective group for hydroxyl group, with a cuprate derived from a compound of Formula 2a:
- wherein P2 is a protective group for hydroxyl group;
- and X is Cl, Br or I, to form a compound of Formula 3:
- wherein R1, P1 and P2 are as defined above;
- (2) removing the P2 group and oxidizing the hydroxyl group in ω-side chain to form a compound of Formula 5:
- wherein R1 and P1 are as defined above;
- and
- (3) removing the P1 and R1 groups.
7 more elements
A compound of Formula 2:
- wherein P2 is a protecting group for hydroxyl group or H;
- and X is Cl, Br or I.
Dependencies are inferred from the claim text.