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WO2009001374A3 - Preparation of ethyl-3'-[((7-chloro-2-quinolinyl)ethenyl)phenyl]-3-oxopropanoate, a key intermediate for montelukast sodium - Google Patents

Preparation of ethyl-3'-[((7-chloro-2-quinolinyl)ethenyl)phenyl]-3-oxopropanoate, a key intermediate for montelukast sodium Download PDF

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Publication number
WO2009001374A3
WO2009001374A3 PCT/IN2008/000398 IN2008000398W WO2009001374A3 WO 2009001374 A3 WO2009001374 A3 WO 2009001374A3 IN 2008000398 W IN2008000398 W IN 2008000398W WO 2009001374 A3 WO2009001374 A3 WO 2009001374A3
Authority
WO
WIPO (PCT)
Prior art keywords
ethenyl
quinolinyl
chloro
ethyl
phenyl
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/IN2008/000398
Other languages
French (fr)
Other versions
WO2009001374A2 (en
Inventor
Ventaka Subba Raju Gottumukkala
Someswara Rao Casukhela
Satyanarayana Chava
Seeta Ramanjaneyulu Gorantla
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.)
Aptuit Laurus Pvt Ltd
Original Assignee
Aptuit Laurus Pvt 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 Aptuit Laurus Pvt Ltd filed Critical Aptuit Laurus Pvt Ltd
Publication of WO2009001374A2 publication Critical patent/WO2009001374A2/en
Anticipated expiration legal-status Critical
Publication of WO2009001374A3 publication Critical patent/WO2009001374A3/en
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Quinoline Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A process for preparing β- ketoester of formula (III) comprises; (a)condensing alkyl 3- formylbenzoate with 7-Chloroquinaldine to give alkyl 3-[((7-chloro-2-quinolinyl) ethenyl)] benzoate; and (b) reacting alkyl 3-[((7-chloro-2-quinolinyl) ethenyl)] benzoate with an alkyl ester in presence of metal hydride/metal alkoxides to obtain a compound β- ketoester of structural formula (Ill) or (a) condensing isophthalaldehyde with 7-Chloroquinaldine to give Ethyl 3-[((7-chloro-2- quinolinyl) ethenyl)] benzaldehyde (b) reacting Ethyl 3-[((7-chloro-2-quinolinyl) ethenyl)] benzaldehyde with an α-halo ester in presence of a metal catalyst to give Ethyl 3'-[((7-chloro- 2-quinolinyl) ethenyl)phenyl] -3 -hydroxy propanoate; and (c) treating Ethyl 3'-[((7-chloro-2- quinolinyl)ethenyl)phenyl]-3-hydroxy propanoate with Collins reagent in an organic solvent to obtain a compound β- ketoester of structural formula (III).
PCT/IN2008/000398 2007-06-25 2008-06-24 Preparation of ethyl-3'-[((7-chloro-2-quinolinyl)ethenyl)phenyl]-3-oxopropanoate, a key intermediate for montelukast sodium Ceased WO2009001374A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1353/CHE/2007 2007-06-25
IN1353CH2007 2007-06-25

Publications (2)

Publication Number Publication Date
WO2009001374A2 WO2009001374A2 (en) 2008-12-31
WO2009001374A3 true WO2009001374A3 (en) 2011-06-30

Family

ID=40186130

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2008/000398 Ceased WO2009001374A2 (en) 2007-06-25 2008-06-24 Preparation of ethyl-3'-[((7-chloro-2-quinolinyl)ethenyl)phenyl]-3-oxopropanoate, a key intermediate for montelukast sodium

Country Status (1)

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WO (1) WO2009001374A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008035379A2 (en) * 2006-09-19 2008-03-27 Aptuit Laurus Private Limited Process for and intermediates of leukotriene antagonists
HUP1000425A2 (en) 2010-08-11 2012-03-28 Richter Gedeon Nyrt Process for the production of montelukast sodium
WO2014081616A1 (en) * 2012-11-21 2014-05-30 Merck Sharp & Dohme Corp. Preparation of precursors for leukotriene antagonists
CN104109122B (en) * 2013-04-16 2017-03-29 浙江奥翔药业股份有限公司 For synthesizing midbody compound of montelukast and preparation method thereof
CN116375639B (en) * 2023-04-19 2024-05-28 南京欧信医药技术有限公司 Method for preparing montelukast sodium intermediate by micro-channel method

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0375348A1 (en) * 1988-12-23 1990-06-27 Smithkline Beecham Corporation Leukotriene antagonists
EP0480716A1 (en) * 1990-10-12 1992-04-15 Merck Frosst Canada Inc. Saturated hydroxyalkylquinoline acids as leukotriene antagonists
US5869673A (en) * 1997-02-28 1999-02-09 Merck & Co., Inc. Process for 3-(2-(7-chloro-2-quinolinyl)ethenyl) - benzaldehyde
US20030195201A1 (en) * 2001-12-10 2003-10-16 Bo Yunxin Y. Vanilloid receptor ligands and their use in treatments

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0375348A1 (en) * 1988-12-23 1990-06-27 Smithkline Beecham Corporation Leukotriene antagonists
EP0480716A1 (en) * 1990-10-12 1992-04-15 Merck Frosst Canada Inc. Saturated hydroxyalkylquinoline acids as leukotriene antagonists
US5869673A (en) * 1997-02-28 1999-02-09 Merck & Co., Inc. Process for 3-(2-(7-chloro-2-quinolinyl)ethenyl) - benzaldehyde
US20030195201A1 (en) * 2001-12-10 2003-10-16 Bo Yunxin Y. Vanilloid receptor ligands and their use in treatments

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
OKARNOTO ET AL.: "A Novel Dual Antagonist of Thromboxane A2 and Leukotriene D4 Receptors: Synthesis and Structure-Activity Relationships of Chioroquinolylvinyl Derivatives", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 54, no. 5, 2006, pages 603 - 610 *

Also Published As

Publication number Publication date
WO2009001374A2 (en) 2008-12-31

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