Method for preparing prostaglandin derivative

• US 7,812,182 B2
• Filed: 02/07/2007
• Issued: 10/12/2010
• Est. Priority Date: 02/07/2006
• Status: Active Grant

• Current Assignee: Sucampo AG (Mallinckrodt plc)
• Original Assignee: R-Tech UENO Limited (Mallinckrodt plc), Sucampo AG (Mallinckrodt plc)
• Inventors: Hirata, Ryu, Masuzaki, Kazuhiro, Ueno, Ryuji, Matsukawa, Tatsuya
• Primary Examiner(s): DENTZ, BERNARD I
• Application Number:
  US11/703,138
• Publication Number:
  US 20070244333A1
• Time in Patent Office: 1,343 Days
• Field of Search: 549/396, 560/121
• US Class Current: 549/396
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07C 405/0025 containing keto groups
• CPC Class Codes: C07D 307/93 condensed with a ring other than six-membered
• CPC Class Codes: C07D 307/935 Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
• CPC Class Codes: C07D 309/12 only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
• CPC Class Codes: C07D 311/94 condensed with rings other than six-membered or with ring systems containing such rings

Abstract

Disclosed is a method for preparing a prostaglandin derivative of formula (A):

which comprises reacting an aldehyde represented by formula (1):

with a 2-oxoalkyl phosphonate in a reaction solvent under the presence of alkali hydroxide as sole base. By carrying out the reaction using an alkali hydroxide as sole base in the reaction system, the desired prostaglandin derivative can be obtained by simple procedures and with high yield.

Claims

1. Benzyl 7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxooctahydro cyclopenta[b]pyran-5-yl]heptanate.