Intermediates for the preparation of lubiprostone

• US 9,012,662 B2
• Filed: 08/21/2014
• Issued: 04/21/2015
• Est. Priority Date: 10/15/2010
• Status: Expired due to Fees

• Current Assignee: ScinoPharm (Kunshan) Biochemical Technology Co., Ltd. (Scinopharm Taiwan Limited)
• Original Assignee: ScinoPharm (Kunshan) Biochemical Technology Co., Ltd. (Scinopharm Taiwan Limited)
• Inventors: Henschke, Julian Paul, Liu, Yuanlian, Xia, Lizhen, Chen, Yung-Fa
• Primary Examiner(s): Jarrell, Noble
• Assistant Examiner(s): MAURO, JOHN MATTHEW
• Application Number:
  US14/464,922
• Publication Number:
  US 20150005528A1
• Time in Patent Office: 243 Days
• Field of Search: 549/396
• US Class Current: 549/396
• 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 (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):