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WO2008150000A1 - Method for production of optically active etodolac - Google Patents

Method for production of optically active etodolac Download PDF

Info

Publication number
WO2008150000A1
WO2008150000A1 PCT/JP2008/060500 JP2008060500W WO2008150000A1 WO 2008150000 A1 WO2008150000 A1 WO 2008150000A1 JP 2008060500 W JP2008060500 W JP 2008060500W WO 2008150000 A1 WO2008150000 A1 WO 2008150000A1
Authority
WO
WIPO (PCT)
Prior art keywords
etodolac
optically active
producing
suspension
active form
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2008/060500
Other languages
French (fr)
Japanese (ja)
Inventor
Shinichi Sugimoto
Hidetaka Fujihara
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Shinyaku Co Ltd
Original Assignee
Nippon Shinyaku Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Shinyaku Co Ltd filed Critical Nippon Shinyaku Co Ltd
Priority to JP2009517920A priority Critical patent/JP5287719B2/en
Publication of WO2008150000A1 publication Critical patent/WO2008150000A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Disclosed is a novel method for producing an optically active form of etodolac. Specifically disclosed is a method for producing an optically active form of etodolac at a high productivity rate, at a low cost and in a simple manner. The method for producing an optically active form of etodolac comprises the steps of: mixing etodolac, cinchonine and methanol to produce a suspension; allowing the suspension to stand or agitating the suspension to cause the precipitation of a salt of (+)-etodolac and cinchonine; and producing (+)-etodolac or (-)-etodolac from the precipitated salt or from a filtrate prepared by filtering off the precipitated salt.
PCT/JP2008/060500 2007-06-07 2008-06-06 Method for production of optically active etodolac Ceased WO2008150000A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2009517920A JP5287719B2 (en) 2007-06-07 2008-06-06 Method for producing optically active etodolac

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007-152085 2007-06-07
JP2007152085 2007-06-07

Publications (1)

Publication Number Publication Date
WO2008150000A1 true WO2008150000A1 (en) 2008-12-11

Family

ID=40093804

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/060500 Ceased WO2008150000A1 (en) 2007-06-07 2008-06-06 Method for production of optically active etodolac

Country Status (2)

Country Link
JP (1) JP5287719B2 (en)
WO (1) WO2008150000A1 (en)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4515961A (en) * 1983-08-16 1985-05-07 American Home Products Corporation Resolution of (±)-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4,-b] indole-1-acetic acid using enrichment crystallization
US4520203A (en) * 1983-08-16 1985-05-28 American Home Products Corporation Resolution of (±)-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid using cinchonine
US5578734A (en) * 1993-01-14 1996-11-26 Apr Applied Pharma Research Sa Method for the preparation of S-(+)-ethodolic acid and saline derivatives
TW434243B (en) * 1997-07-29 2001-05-16 Dev Center Biotechnology Method for the optical resolution of etodolac-an antiarthritic drug
US20050014953A1 (en) * 2003-07-18 2005-01-20 Chemi Spa Method for the racemization of etodolic acid

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4515961A (en) * 1983-08-16 1985-05-07 American Home Products Corporation Resolution of (±)-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4,-b] indole-1-acetic acid using enrichment crystallization
US4520203A (en) * 1983-08-16 1985-05-28 American Home Products Corporation Resolution of (±)-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid using cinchonine
US5578734A (en) * 1993-01-14 1996-11-26 Apr Applied Pharma Research Sa Method for the preparation of S-(+)-ethodolic acid and saline derivatives
TW434243B (en) * 1997-07-29 2001-05-16 Dev Center Biotechnology Method for the optical resolution of etodolac-an antiarthritic drug
US20050014953A1 (en) * 2003-07-18 2005-01-20 Chemi Spa Method for the racemization of etodolic acid

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHOU S.-Y. ET AL.: "Exploration of an efficient method for optical resolution of etodolac", JOURNAL OF THE CHINESE CHEMICAL SOCIETY, vol. 48, no. 2, 2001, pages 229 - 234, XP003001766 *

Also Published As

Publication number Publication date
JPWO2008150000A1 (en) 2010-08-26
JP5287719B2 (en) 2013-09-11

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