WO2008047388A3 - Procédé amélioré de préparation de ranolazine - Google Patents

Procédé amélioré de préparation de ranolazine Download PDF

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Publication number
WO2008047388A3
WO2008047388A3 PCT/IN2007/000494 IN2007000494W WO2008047388A3 WO 2008047388 A3 WO2008047388 A3 WO 2008047388A3 IN 2007000494 W IN2007000494 W IN 2007000494W WO 2008047388 A3 WO2008047388 A3 WO 2008047388A3
Authority
WO
WIPO (PCT)
Prior art keywords
ranolazine
derivative
preparation
improved process
base
Prior art date
Application number
PCT/IN2007/000494
Other languages
English (en)
Other versions
WO2008047388A2 (fr
Inventor
Rahul Saxena
Chidambaram Venkateswaran Srinivasan
Lalit Wadhwa
Original Assignee
Ind-Swift Laboratories Limited
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 Ind-Swift Laboratories Limited filed Critical Ind-Swift Laboratories Limited
Publication of WO2008047388A2 publication Critical patent/WO2008047388A2/fr
Publication of WO2008047388A3 publication Critical patent/WO2008047388A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • C07D303/23—Oxiranylmethyl ethers of compounds having one hydroxy group bound to a six-membered aromatic ring, the oxiranylmethyl radical not being further substituted, i.e.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne un procédé amélioré de préparation d'une ranolazine de formule (I) et de ses sels pharmaceutiquement acceptables. Ce procédé consiste à faire réagir un dérivé de 2,6-diméthylaniline avec du chlorure de chloroacétyle en présence d'une base dans l'eau, à faire réagir le produit intermédiaire d'amide résultant avec une pipérazine et à condenser le dérivé pipérazinique résultant avec un dérivé d'oxirane (préparé par réaction de 2-méthoxyphénol avec de l'épichlorohydrine en présence d'une base au moyen d'un catalyseur de transfert de phase) dans un solvant inerte, puis à isoler une ranolazine de pureté élevée et à la convertir en ses sels acides au moyen d'un acide minéral en excès.
PCT/IN2007/000494 2006-10-20 2007-10-18 Procédé amélioré de préparation de ranolazine WO2008047388A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2306/DEL/2006 2006-10-20
IN2306DE2006 2006-10-20

Publications (2)

Publication Number Publication Date
WO2008047388A2 WO2008047388A2 (fr) 2008-04-24
WO2008047388A3 true WO2008047388A3 (fr) 2009-10-15

Family

ID=39314468

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2007/000494 WO2008047388A2 (fr) 2006-10-20 2007-10-18 Procédé amélioré de préparation de ranolazine

Country Status (1)

Country Link
WO (1) WO2008047388A2 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR072196A1 (es) * 2008-06-19 2010-08-11 Medichem Sa Procedimiento para preparar ranolazina purificada, util en el tratamiento cronico de la angina.
WO2010023687A2 (fr) * 2008-08-28 2010-03-04 Shodhana Laboratories Limited Préparation de la ranolazine, ses sels et des intermédiaires de ceux-ci
WO2010025370A2 (fr) * 2008-08-28 2010-03-04 Dr. Reddy's Laboratories Ltd. Préparation de ranolazine
US20110223213A1 (en) * 2008-10-15 2011-09-15 Actavis Group Ptc Ehf Highly pure ranolazine or a pharmaceutically acceptable salt thereof
WO2010097805A1 (fr) 2009-02-24 2010-09-02 Lupin Limited Procédé pour la préparation de ranolazine
CN101838249B (zh) * 2010-03-19 2015-08-19 浙江华海药业股份有限公司 一种制备高纯度愈创木酚缩水甘油醚的方法
MX355697B (es) 2010-04-12 2018-04-27 Supernus Pharmaceuticals Inc Métodos para producir sales de viloxazina y polimorfos novedosos de las mismas.
CN102295622A (zh) 2010-06-25 2011-12-28 上海冠杰生物医药科技有限公司 一种雷诺嗪的制备方法
CN103664829A (zh) * 2014-01-02 2014-03-26 成都医路康医学技术服务有限公司 一种雷诺嗪的合成工艺
US10266507B2 (en) 2015-03-10 2019-04-23 Unichem Laboratories Limited Process for the preparation of ranolazine
CN111440131B (zh) * 2020-04-27 2021-12-28 江苏惠利生物科技有限公司 一种易分解的愈创木酚缩水甘油醚的精制方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4567264A (en) * 1983-05-18 1986-01-28 Syntex (U.S.A.) Inc. Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry
EP0483932A1 (fr) * 1990-10-31 1992-05-06 Richter Gedeon Vegyeszeti Gyar R.T. Procédé pour la préparation de dérivés de la pipérazine
WO2006008753A1 (fr) * 2004-07-19 2006-01-26 Unichem Laboratories Limited Forme cristalline et amorphe de ranolazine et son processus de fabrication
CN1915982A (zh) * 2006-09-26 2007-02-21 严洁 一种雷诺嗪合成方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4567264A (en) * 1983-05-18 1986-01-28 Syntex (U.S.A.) Inc. Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry
EP0483932A1 (fr) * 1990-10-31 1992-05-06 Richter Gedeon Vegyeszeti Gyar R.T. Procédé pour la préparation de dérivés de la pipérazine
WO2006008753A1 (fr) * 2004-07-19 2006-01-26 Unichem Laboratories Limited Forme cristalline et amorphe de ranolazine et son processus de fabrication
CN1915982A (zh) * 2006-09-26 2007-02-21 严洁 一种雷诺嗪合成方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
LI, SHU-CHUN ET AL.: "Synthesis of a novel antianginal agent Ranolazine", ZHONGGUO YAOWU HUAXUE ZAZHI, vol. 13, no. 5, 2003, pages 283 - 285 *
LU, WENCHAO ET AL.: "Synthesis of Ranozaline", ZHONGGUO YIYAO GONGYE ZAZHI, vol. 35, no. 11, 2004, pages 641,642 - ,283-285 *

Also Published As

Publication number Publication date
WO2008047388A2 (fr) 2008-04-24

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