EP2094665A2 - Préparation de montélukast et de ses sels - Google Patents

Préparation de montélukast et de ses sels

Info

Publication number
EP2094665A2
EP2094665A2 EP07844907A EP07844907A EP2094665A2 EP 2094665 A2 EP2094665 A2 EP 2094665A2 EP 07844907 A EP07844907 A EP 07844907A EP 07844907 A EP07844907 A EP 07844907A EP 2094665 A2 EP2094665 A2 EP 2094665A2
Authority
EP
European Patent Office
Prior art keywords
formula
afford
compound
montelukast
liters
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.)
Withdrawn
Application number
EP07844907A
Other languages
German (de)
English (en)
Other versions
EP2094665A4 (fr
Inventor
Pratap Reddy Padi
Satyanarayana Bollikonda
Narsimha Naidu
Debasish Ghosh
Kiran Kumar VENKATA KANDIRELLI
Rajender Reddy Jinna
Ravi Kumar Kasturi
Saravanan Mohanarangam
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.)
Dr Reddys Laboratories Ltd
Dr Reddys Laboratories Inc
Original Assignee
Dr Reddys Laboratories Ltd
Dr Reddys Laboratories Inc
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 Dr Reddys Laboratories Ltd, Dr Reddys Laboratories Inc filed Critical Dr Reddys Laboratories Ltd
Publication of EP2094665A2 publication Critical patent/EP2094665A2/fr
Publication of EP2094665A4 publication Critical patent/EP2094665A4/fr
Withdrawn legal-status Critical Current

Links

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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

  • a process for the purification of dicyclohexylamine salt of montelukast including: a) providing a solution of dicyclohexylamine salt of montelukast in a combination of an alcoholic solvent and a nitrile solvent; b) cooling the solution thereby causing a solid dicyclohexylamine salt of montelukast to separate therefrom; c) isolating the separated solid.
  • the moisture present in the starting diol intermediate of Formula (II) may be removed by performing azeotropic distillation of its solution in a hydrocarbon solvent such as toluene.
  • the moisture content of the individual reactants such as the methanesulfonyl chloride, diisopropyl ethylamine and the solvents is preferably below about 0.2% w/w to ensure that the moisture content of the total reaction medium is minimized, preferably to below about 0.2% w/w.
  • Suitable alcoholic solvents which can be used for suspending montelukast dicyclohexylamine salt include, but are not limited to alcohols such as methanol, ethanol, isopropyl alcohol, n-propanol, and the like; and suitable nitrile solvents which can be used for the purpose include, but are not limited to acetonitrile, propionitrile and the like.
  • the ratio of the alcoholic solvent to the nitrile solvent which can be used for purification ranges from about 1 :3 to about 1 :5.
  • EXAMPLE 12 PREPRATION OF 2-(3-(3-[2-(7-CHLORO-QUINOLIN ⁇ -YL)-VINYL]- PHENYL ⁇ -3-HYDROXY-PROPYL)-BENZOIC ACID METHYL ESTER (FORMULA XIII):
  • reaction mass was then cooled to -10 0 C and triethylamine (47 liters) was added to the reaction mass at about -10 0 C followed by the addition of thioacetic acid (18 liters) at about O 0 C.
  • the reaction mass was maintained at about 0 0 C for about 2 hours and then the temperature was raised to 30 0 C and maintained for 20 hours.
  • water 250 liters was added and the organic layer was separated. The aqueous layer was extracted with toluene (3x150 liters). The combined organic layer was washed with water (3*125 liters). To the obtained organic layer carbon (1.25 kg) was added and maintained for about 30 minutes.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)

Abstract

Cette invention concerne un procédé de préparation du montélukast de formule (I).
EP07844907A 2006-11-06 2007-11-06 Préparation de montélukast et de ses sels Withdrawn EP2094665A4 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
IN2042CH2006 2006-11-06
IN142CH2007 2007-01-22
US89021507P 2007-02-16 2007-02-16
US91486207P 2007-04-30 2007-04-30
PCT/US2007/083756 WO2008058118A2 (fr) 2006-11-06 2007-11-06 Préparation de montélukast et de ses sels

Publications (2)

Publication Number Publication Date
EP2094665A2 true EP2094665A2 (fr) 2009-09-02
EP2094665A4 EP2094665A4 (fr) 2010-11-24

Family

ID=39365306

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07844907A Withdrawn EP2094665A4 (fr) 2006-11-06 2007-11-06 Préparation de montélukast et de ses sels

Country Status (2)

Country Link
EP (1) EP2094665A4 (fr)
WO (1) WO2008058118A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9717684B2 (en) 2014-04-25 2017-08-01 R.P. Scherer Technologies, Llc Stable montelukast solution

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2608369A1 (fr) 2005-07-05 2007-01-11 Teva Pharmaceutical Industries Ltd. Purification du montelukast
WO2008035379A2 (fr) * 2006-09-19 2008-03-27 Aptuit Laurus Private Limited Procédé de production d'antagonistes de leucotriène et produits intermédiaires correspondants
EP2552892A1 (fr) 2010-03-31 2013-02-06 KRKA, D.D., Novo Mesto Synthèse efficace pour la préparation de montélukast et nouvelle forme cristalline d'intermédiaires dans celle-ci
CN102702097A (zh) * 2012-05-16 2012-10-03 浙江大学 一种孟鲁司特钠中间体的制备方法
CN104109122B (zh) * 2013-04-16 2017-03-29 浙江奥翔药业股份有限公司 用于合成孟鲁司特的中间体化合物及其制备方法
CN103288695B (zh) * 2013-06-18 2016-01-13 成都迈斯克医药科技有限公司 1-巯甲基环丙基乙酸的制备方法
CN103554016B (zh) * 2013-08-23 2015-09-23 南通正达农化有限公司 一种非激素抗炎药中间体的加工工艺
CN103554017B (zh) * 2013-10-25 2014-12-17 河北序能生物技术有限公司 一种孟鲁司特钠手性中间体的制备方法
CN104592110A (zh) * 2015-01-26 2015-05-06 中山奕安泰医药科技有限公司 一种合成2-[3-(s)-[3-[2-(7-氯-2-喹啉基)乙烯基]苯基]-3-羟基丙基]苯甲酸甲酯的工艺
CN109020830A (zh) * 2018-08-29 2018-12-18 广州康瑞泰药业有限公司 一种羟甲基环丙基乙腈衍生物及其制备和应用方法
CN114702416A (zh) * 2022-03-30 2022-07-05 法姆瑞斯医药科技(北京)有限公司 一种高效制备孟鲁司特钠侧链中间体的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995018107A1 (fr) * 1993-12-28 1995-07-06 Merck & Co., Inc. Procede de preparation d'antagonistes des leukotrienes
US20050234241A1 (en) * 2004-04-15 2005-10-20 Venkataraman Sundaram Process for the preparation of [R-(E)-1-[[[1-[3-[2-[7-chloro-2-quinolinyl]ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid (montelukast) and its pharmaceutically acceptable salts
WO2006021974A1 (fr) * 2004-08-23 2006-03-02 Morepen Laboratories Limited Procede pour synthetiser un diol (viii), intermediaire du sodium de montelukast

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5565473A (en) * 1990-10-12 1996-10-15 Merck Frosst Canada, Inc. Unsaturated 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
DE19963115B4 (de) * 1999-12-24 2009-04-09 Evonik Degussa Gmbh Verfahren zur Herstellung von Cyclopropan-1,1-dicarbonsäurediestern

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995018107A1 (fr) * 1993-12-28 1995-07-06 Merck & Co., Inc. Procede de preparation d'antagonistes des leukotrienes
US20050234241A1 (en) * 2004-04-15 2005-10-20 Venkataraman Sundaram Process for the preparation of [R-(E)-1-[[[1-[3-[2-[7-chloro-2-quinolinyl]ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid (montelukast) and its pharmaceutically acceptable salts
WO2006021974A1 (fr) * 2004-08-23 2006-03-02 Morepen Laboratories Limited Procede pour synthetiser un diol (viii), intermediaire du sodium de montelukast

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
SASSIAN ET AL: "Solvation Effects in the Grignard Reacion with Carbonyl Compounds" HELVETICA CHIMICA ACTA,, vol. 86, 1 January 2003 (2003-01-01), pages 82-90, XP008109226 *
See also references of WO2008058118A2 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9717684B2 (en) 2014-04-25 2017-08-01 R.P. Scherer Technologies, Llc Stable montelukast solution

Also Published As

Publication number Publication date
EP2094665A4 (fr) 2010-11-24
WO2008058118A2 (fr) 2008-05-15
WO2008058118A3 (fr) 2008-07-10

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