INTERMEDIATES FOR THE PREPARATION OF LUBIPROSTONE

• US 20150005528A1
• Filed: 08/21/2014
• Published: 01/01/2015
• Est. Priority Date: 10/15/2010
• Status: Active Grant

• Current Assignee: ScinoPharm (Kunshan) Biochemical Technology Co., Ltd. (Scinopharm Taiwan Limited)
• Original Assignee: Cinopharm Biochemical Technology Company Limited
• Inventors: HENSCHKE, Julian Paul, LIU, Yuanlian, CHEN, Yung-Fa, XIA, Lizhen
• Granted Patent: US 9,012,662 B2
• Time in Patent Office: Days
• US Class Current: 560/121
• CPC Class Codes: A61P 1/12 Antidiarrhoeals
• CPC Class Codes: C07C 2601/08 the ring being saturated
• CPC Class Codes: C07C 29/143 of ketones
• CPC Class Codes: C07C 33/42 acyclic
• 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 59/215 containing singly bound oxygen containing groups
• CPC Class Codes: C07C 69/716 Esters of keto-carboxylic acids or aldehydo-carboxylic acids
• CPC Class Codes: C07D 311/74 Benzo[b]pyrans, hydrogenated in the carbocyclic ring
• CPC Class Codes: C07D 311/94 condensed with rings other than six-membered or with ring systems containing such rings
• CPC Class Codes: C12P 31/00 Preparation of compounds containing a five-membered ring having two side-chains in ortho position to each other, and having at least one oxygen atom directly bound to the ring in ortho position to one of the side-chains, one side-chain containing, not directly bound 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 at least one oxygen atom bound in gamma-position to the ring, e.g. prostaglandins
• CPC Class Codes: C12Y 301/01003 Triacylglycerol lipase (3.1.1.3)

Abstract

Intermediates of the following formulae for the preparation of lubiprostone:

Claims

1. A compound of formula (9) (isopropyl 7-((1R,2R,3R)-3-(tert-butyldimethylsilyloxy)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopentyl)heptanoate):

2. A compound of formula (10) (7-((1R,2R,3R)-3-(tert-butyldimethylsilyloxy)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopentyl)heptanoic acid):

3. A compound of formula (7) ((Z)-isopropyl 7-((1R,2R,3R)-2-((1E,5E)-3-(benzyloxy)-4,4-difluoroocta-1,5-dienyl)-3-(tert-butyldimethylsilyloxy)-5-oxocyclopentyl)hept-5-enoate):