Process for the preparation of Lubiprostone and intermediates thereof

• US 10,457,623 B1
• Filed: 07/13/2018
• Issued: 10/29/2019
• Est. Priority Date: 07/13/2018
• Status: Active Grant

• Current Assignee: Chirogate International Inc.
• Original Assignee: Chirogate International Inc.
• Inventors: Wei, Shih-Yi, Hsu, Min-Kuan
• Primary Examiner(s): Carcanague, Daniel R
• Application Number:
  US16/034,598
• Time in Patent Office: 473 Days
• Field of Search: 549214
• CPC Class Codes: C07C 2601/08 the ring being saturated
• CPC Class Codes: C07C 31/40 perhalogenated
• CPC Class Codes: C07C 405/00 Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
• CPC Class Codes: C07C 51/373 by introduction of functional groups containing oxygen only in doubly bound form
• CPC Class Codes: C07D 307/06 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
• CPC Class Codes: C07D 307/20 Oxygen atoms
• CPC Class Codes: C07D 311/94 condensed with rings other than six-membered or with ring systems containing such rings
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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.

Claims

1. A process for preparing Lubiprostone, comprising the steps of:

(1) coupling a cyclopentenone of Formula 1;

2. A compound of Formula 2: