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WO2012041263A3 - A method of manufacturing 2-({(5s)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]- l,3-oxazolidin-5-yl}methyl)-lh-isoindol-l,3(2h)-dione with a high optical purity - Google Patents

A method of manufacturing 2-({(5s)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]- l,3-oxazolidin-5-yl}methyl)-lh-isoindol-l,3(2h)-dione with a high optical purity Download PDF

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Publication number
WO2012041263A3
WO2012041263A3 PCT/CZ2011/000095 CZ2011000095W WO2012041263A3 WO 2012041263 A3 WO2012041263 A3 WO 2012041263A3 CZ 2011000095 W CZ2011000095 W CZ 2011000095W WO 2012041263 A3 WO2012041263 A3 WO 2012041263A3
Authority
WO
WIPO (PCT)
Prior art keywords
oxo
isoindol
dione
phenyl
oxazolidin
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/CZ2011/000095
Other languages
French (fr)
Other versions
WO2012041263A2 (en
Inventor
Miroslav Urbasek
Pavel Hradil
Martin Grepl
Petra Fialova
Vladimir Oremus
Petr Slezar
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.)
Farmak AS
Original Assignee
Farmak AS
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 Farmak AS filed Critical Farmak AS
Publication of WO2012041263A2 publication Critical patent/WO2012041263A2/en
Publication of WO2012041263A3 publication Critical patent/WO2012041263A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Highly optically pure 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-l,3-oxazolidin- 5-yl} methyl)- lH-isoindol- l,3(2H)-dione (I) is obtained by reaction of 2-((2R)-2-hydroxy-3-[4-(3- oxo-4-moφholinyl)phenyl]amino-propyl)- lH-isoindol- l,3(2H)-dione (III), containing the (2S)- isomer (Illb), with N,N-carbonyldiimidazole in tetrahydrofuran, preferably without the presence of the catalyst 4-dimethylaminopyridine, said reaction being carried out in such a manner that it is terminated at a moment when the reaction mixture still contains the unreacted compound of formula III in an amount which is in the range of a 3 to 5 fold the initial amount of the (2S)- isomer in the starting substance of formula III.
PCT/CZ2011/000095 2010-09-30 2011-09-27 A method of manufacturing 2-({(5s)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]- l,3-oxazolidin-5-yl}methyl)-lh-isoindol-l,3(2h)-dione with a high optical purity Ceased WO2012041263A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CZPV2010-714 2010-09-30
CZ20100714A CZ2010714A3 (en) 2010-09-30 2010-09-30 Process for preparing extreme optically pure 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione

Publications (2)

Publication Number Publication Date
WO2012041263A2 WO2012041263A2 (en) 2012-04-05
WO2012041263A3 true WO2012041263A3 (en) 2012-06-21

Family

ID=45418269

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CZ2011/000095 Ceased WO2012041263A2 (en) 2010-09-30 2011-09-27 A method of manufacturing 2-({(5s)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]- l,3-oxazolidin-5-yl}methyl)-lh-isoindol-l,3(2h)-dione with a high optical purity

Country Status (2)

Country Link
CZ (1) CZ2010714A3 (en)
WO (1) WO2012041263A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014096214A1 (en) 2012-12-21 2014-06-26 Farma Grs, D.O.O. A process for preparation of rivaroxaban
US20170267669A1 (en) * 2014-08-25 2017-09-21 Cipla Limited Process for the Preparation of Rivaroxaban
CN110054623A (en) * 2019-05-29 2019-07-26 浙江燎原药业股份有限公司 A kind of preparation method of Rivaroxaban intermediate
CN111675705A (en) * 2020-08-11 2020-09-18 北京鑫开元医药科技有限公司 Preparation method of 4- (4-aminophenyl) morpholine-3-one derivative

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001047919A1 (en) * 1999-12-24 2001-07-05 Bayer Aktiengesellschaft Substituted oxazolidinones and their use in the field of blood coagulation
DE102004002044A1 (en) * 2004-01-15 2005-08-04 Bayer Healthcare Ag manufacturing

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2425183T3 (en) 2007-08-14 2013-10-11 Concert Pharmaceuticals Inc. Substituted oxazolidinone derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001047919A1 (en) * 1999-12-24 2001-07-05 Bayer Aktiengesellschaft Substituted oxazolidinones and their use in the field of blood coagulation
DE102004002044A1 (en) * 2004-01-15 2005-08-04 Bayer Healthcare Ag manufacturing

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DISCLOSED ANONYMOUSLY: "Crystalline form of 2-({2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H-dione", IP.COM JOURNAL, vol. 10(6A), no. 17 (ipcom000195959D), 24 May 2010 (2010-05-24), XP002674230, ISSN: 1533-0001 *

Also Published As

Publication number Publication date
CZ2010714A3 (en) 2012-04-11
WO2012041263A2 (en) 2012-04-05

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