ES2653709R1 - Nuevo método para la preparación de ivabradina base altamente pura y sales de la misma - Google Patents

Nuevo método para la preparación de ivabradina base altamente pura y sales de la misma Download PDF

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Publication number
ES2653709R1
ES2653709R1 ES201700315A ES201700315A ES2653709R1 ES 2653709 R1 ES2653709 R1 ES 2653709R1 ES 201700315 A ES201700315 A ES 201700315A ES 201700315 A ES201700315 A ES 201700315A ES 2653709 R1 ES2653709 R1 ES 2653709R1
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Spain
Prior art keywords
salts
preparation
highly pure
new method
ivabradine base
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.)
Granted
Application number
ES201700315A
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English (en)
Other versions
ES2653709A2 (es
ES2653709B1 (es
Inventor
José Luís DEL RÍO PERICACHO
Yolanda ARREDONDO MARTÍNEZ
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.)
Urquima SA
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Urquima SA
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Publication of ES2653709A2 publication Critical patent/ES2653709A2/es
Publication of ES2653709R1 publication Critical patent/ES2653709R1/es
Application granted granted Critical
Publication of ES2653709B1 publication Critical patent/ES2653709B1/es
Expired - Fee Related legal-status Critical Current
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/16—Benzazepines; Hydrogenated benzazepines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/25—Sulfonic acids having sulfo groups bound to carbon atoms of rings other than six-membered aromatic rings of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
    • C07D223/08—Oxygen atoms
    • C07D223/10—Oxygen atoms attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/06—One of the condensed rings being a six-membered aromatic ring the other ring being four-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

Nuevo método para la preparación de ivabradina base altamente pura y sales de la misma.#Método para la preparación de ivabradina purificada y sales de la misma, método para la purificación de ivabradina y sales de la misma, nuevo reactivo usado en dichos métodos y uso de dicho reactivo para la preparación de ivabradina.
ES201700315A 2015-06-03 2016-06-02 Nuevo Método para la preparación de Ivabradina base altamente pura y sales de la misma Expired - Fee Related ES2653709B1 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP15382293.7A EP3101010A1 (en) 2015-06-03 2015-06-03 New method for the preparation of highly pure ivabradine base and salts thereof
EP15382293 2015-06-03
PCT/EP2016/062533 WO2016193386A2 (en) 2015-06-03 2016-06-02 New method for the preparation of highly pure ivabradine base and salts thereof

Publications (3)

Publication Number Publication Date
ES2653709A2 ES2653709A2 (es) 2018-02-08
ES2653709R1 true ES2653709R1 (es) 2018-02-13
ES2653709B1 ES2653709B1 (es) 2018-11-21

Family

ID=53398017

Family Applications (2)

Application Number Title Priority Date Filing Date
ES16728882T Active ES2854284T3 (es) 2015-06-03 2016-06-02 Nuevo método para la preparación de Ivabradina base altamente pura y sales de la misma
ES201700315A Expired - Fee Related ES2653709B1 (es) 2015-06-03 2016-06-02 Nuevo Método para la preparación de Ivabradina base altamente pura y sales de la misma

Family Applications Before (1)

Application Number Title Priority Date Filing Date
ES16728882T Active ES2854284T3 (es) 2015-06-03 2016-06-02 Nuevo método para la preparación de Ivabradina base altamente pura y sales de la misma

Country Status (8)

Country Link
US (1) US10221141B2 (es)
EP (2) EP3101010A1 (es)
DK (1) DK3303297T3 (es)
ES (2) ES2854284T3 (es)
LT (1) LT3303297T (es)
PL (1) PL3303297T3 (es)
PT (1) PT3303297T (es)
WO (1) WO2016193386A2 (es)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008065681A2 (en) * 2006-11-30 2008-06-05 Cadila Healthcare Limited Process for preparation of ivabradine hydrochloride
WO2010072409A1 (en) * 2008-12-22 2010-07-01 Krka, D. D., Novo Mesto Process for preparation of ivabradine
EP2740725A1 (fr) * 2012-12-06 2014-06-11 Les Laboratoires Servier Nouveau procédé de synthèse du 3-(2-bromo-4,5-diméthoxyphényl)propanenitrile, et application à la synthèse de l'ivabradine et de ses sels d'addition à un acide pharmaceutiquement acceptable
WO2015022702A2 (en) * 2013-08-10 2015-02-19 Ind-Swift Laboratories Limited Process for preparation of 4,5-dimethoxybenzene derivatives and use in the synthesis of ivabradine and salts thereof

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2681862B1 (fr) 1991-09-27 1993-11-12 Adir Cie Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent.
FR2868777B1 (fr) 2004-04-13 2006-05-26 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR2870537A1 (fr) 2004-05-19 2005-11-25 Servier Lab Nouveau procede de synthese du (1s)-4,5-dimethoxy-1-(methyl aminomethyl-)-benzocyclobutane et de ses sels d'addition, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
CN101434552B (zh) 2007-11-16 2012-05-23 江苏恒瑞医药股份有限公司 4,5-二甲氧基-1-(甲基氨基甲基)-苯并环丁烷的拆分
FR2932800B1 (fr) 2008-06-20 2015-02-20 Servier Lab Nouveau procede de synthese de la 7,8-dimethoxy-1,3-dihydro- 2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR2933975B1 (fr) 2008-07-17 2011-02-18 Servier Lab Nouveau procede de preparation de benzocyclobutenes fonctionnalises,et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable.
FR2935381B1 (fr) 2008-08-29 2010-12-17 Servier Lab Nouveau procede de resolution des enantiomerees du (3,4-dimethoxy-bicyclo°4.2.0!octa-1,3,5-trien-7-yl)nitrile et application a la synthese de l'ivabradine
CN101671265B (zh) 2008-09-12 2012-08-15 中国科学院上海药物研究所 一种苯并环丁烷类化合物及其制备方法与用途
FR2940287B1 (fr) 2008-12-24 2010-12-24 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable.
FR2941695B1 (fr) 2009-02-04 2011-02-18 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR2943667B1 (fr) 2009-03-31 2011-05-06 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable.
ME00986B (me) 2009-03-31 2012-06-20 Servier Lab Novi postupak sinteze ivabradina i njegovih adicionih soli sa farmaceutski prihvatljivom kiselinom
HUP1000245A2 (en) 2010-05-07 2011-11-28 Richter Gedeon Nyrt Industrial process for the production ivabradin salts
CN102249937A (zh) 2010-05-18 2011-11-23 上海京新生物医药有限公司 1-(s)-4,5-二甲氧基-1-甲胺基甲基-苯并环丁烷的制备方法
CN101857549B (zh) 2010-06-22 2013-04-10 浙江美诺华药物化学有限公司 (1s)-4,5-二甲氧基-1-(甲基氨基甲基)-苯并环丁烷的合成方法
EP2495237A1 (en) 2011-03-04 2012-09-05 Alembic Pharmaceuticals Limited An improved process for the preparation of highly pure ivabradine hydrochloride
CN102372642B (zh) 2011-07-04 2014-01-08 江苏宇田生物医药科技有限公司 (1s)-4,5-二甲氧基-1-[(甲基氨基)甲基]苯并环丁烷的制备方法
ITMI20111467A1 (it) 2011-08-01 2013-02-02 Laboratorio Chimico Int Spa Procedimento per la preparazione di ivabradina e di suoi intermedi di sintesi
CN102408346B (zh) 2011-10-31 2014-07-02 江苏阿尔法药业有限公司 一种4,5-二甲氧基-1-（甲基氨基甲基）-苯并环丁烷的制备方法
FR2986804A1 (fr) 2012-02-09 2013-08-16 Servier Lab Procede de synthese enzymatique de l'acide (7s) 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene 7-carboxylique ou de ses esters, et application a la synthese de l'ivabradine et de ses sels
FR2993561B1 (fr) 2012-07-17 2014-10-31 Servier Lab Procede de synthese enzymatique de la (7s)-1-(3,4-dimethoxy bicyclo[4.2.0]octa-1,3,5-triene 7-yl) n-methyl methanamine, et application a la synthese de l'ivabradine et de ses sels
FR2996845A1 (fr) 2012-10-12 2014-04-18 Servier Lab Nouveau procede de synthese du 3-(2-bromo-4,5-dimethoxyphenyl)propanenitrile, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR2997696B1 (fr) 2012-11-08 2014-12-05 Servier Lab Nouveau procede de synthese du (2e)-3-(3,4-dimethoxyphenyl)prop-2-enenitrile, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR3002542B1 (fr) 2013-02-28 2016-01-22 Servier Lab Procede de synthese enzymatique de l'acide (7s) 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene 7-carboxylique et application a la synthese de l'ivabradine et de ses sels
FR3005658B1 (fr) 2013-05-17 2015-04-24 Servier Lab "procede de synthese du 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable"
CN103524360B (zh) 2013-10-17 2015-09-30 安徽安腾药业有限责任公司 一种伊伐布雷定关键中间体的合成方法
CN104557573B (zh) 2013-10-24 2018-02-27 上海天慈生物谷生物工程有限公司 (1s)‑4,5‑二甲氧基‑1‑[(甲基氨基)甲基]苯并环丁烷盐酸盐的制备方法
CN104262179A (zh) 2014-09-10 2015-01-07 王晓伟 一种伊伐布雷定的关键中间体制备方法
HU230826B1 (hu) 2014-11-19 2018-07-30 Richter Gedeon Nyrt. Eljárás benzazepin származékok előállítására
CN104829470B (zh) 2015-04-20 2017-08-25 江苏宇田医药有限公司 一组合成伊伐布雷定的中间体化合物及其应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008065681A2 (en) * 2006-11-30 2008-06-05 Cadila Healthcare Limited Process for preparation of ivabradine hydrochloride
WO2010072409A1 (en) * 2008-12-22 2010-07-01 Krka, D. D., Novo Mesto Process for preparation of ivabradine
EP2740725A1 (fr) * 2012-12-06 2014-06-11 Les Laboratoires Servier Nouveau procédé de synthèse du 3-(2-bromo-4,5-diméthoxyphényl)propanenitrile, et application à la synthèse de l'ivabradine et de ses sels d'addition à un acide pharmaceutiquement acceptable
WO2015022702A2 (en) * 2013-08-10 2015-02-19 Ind-Swift Laboratories Limited Process for preparation of 4,5-dimethoxybenzene derivatives and use in the synthesis of ivabradine and salts thereof

Also Published As

Publication number Publication date
EP3303297B1 (en) 2020-12-02
DK3303297T3 (da) 2021-02-01
LT3303297T (lt) 2021-03-10
ES2653709A2 (es) 2018-02-08
PL3303297T3 (pl) 2021-06-28
EP3303297A2 (en) 2018-04-11
ES2653709B1 (es) 2018-11-21
EP3101010A1 (en) 2016-12-07
WO2016193386A3 (en) 2017-01-12
PT3303297T (pt) 2021-03-01
ES2854284T3 (es) 2021-09-21
US10221141B2 (en) 2019-03-05
US20180162820A1 (en) 2018-06-14
WO2016193386A2 (en) 2016-12-08

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