EA200901051A1 - Новый способ разделения энантиомеров (3,4-диметоксибицикло[4.2.0]окта-1,3,5-триен-7-ил)нитрила и применение при синтезе ивабрадина - Google Patents

Новый способ разделения энантиомеров (3,4-диметоксибицикло[4.2.0]окта-1,3,5-триен-7-ил)нитрила и применение при синтезе ивабрадина

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Publication number
EA200901051A1
EA200901051A1 EA200901051A EA200901051A EA200901051A1 EA 200901051 A1 EA200901051 A1 EA 200901051A1 EA 200901051 A EA200901051 A EA 200901051A EA 200901051 A EA200901051 A EA 200901051A EA 200901051 A1 EA200901051 A1 EA 200901051A1
Authority
EA
Eurasian Patent Office
Prior art keywords
dimetoxibiciclo
ivabradin
trien
octa
enantiomers
Prior art date
Application number
EA200901051A
Other languages
English (en)
Other versions
EA015777B1 (ru
Inventor
Жан-Мишель Лерестиф
Жан-Пьерр Лекув
Даньель Дрон
Эрик Гожон
Маризе Фан
Original Assignee
Ле Лаборатуар Сервье
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
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=40431490&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EA200901051(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Ле Лаборатуар Сервье filed Critical Ле Лаборатуар Сервье
Publication of EA200901051A1 publication Critical patent/EA200901051A1/ru
Publication of EA015777B1 publication Critical patent/EA015777B1/ru

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/32—Separation; Purification; Stabilisation; Use of additives
    • C07C253/34—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/47—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of rings being part of condensed ring systems
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Vascular Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Способ разделения оптических изомеров соединения формулы (I)с помощью хиральной хроматографии. Применение при синтезе ивабрадина, его солей присоединения с фармацевтически приемлемой кислотой и его гидратов.
EA200901051A 2008-08-29 2009-08-28 Способ разделения энантиомеров (3,4-диметоксибицикло[4.2.0]окта-1,3,5-триен-7-ил)нитрила и применение при синтезе ивабрадина EA015777B1 (ru)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0804755A FR2935381B1 (fr) 2008-08-29 2008-08-29 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

Publications (2)

Publication Number Publication Date
EA200901051A1 true EA200901051A1 (ru) 2010-04-30
EA015777B1 EA015777B1 (ru) 2011-12-30

Family

ID=40431490

Family Applications (1)

Application Number Title Priority Date Filing Date
EA200901051A EA015777B1 (ru) 2008-08-29 2009-08-28 Способ разделения энантиомеров (3,4-диметоксибицикло[4.2.0]окта-1,3,5-триен-7-ил)нитрила и применение при синтезе ивабрадина

Country Status (39)

Country Link
US (3) US8536365B2 (ru)
EP (1) EP2166004B1 (ru)
JP (2) JP5663154B2 (ru)
KR (1) KR101119309B1 (ru)
CN (1) CN101659631B (ru)
AR (1) AR073147A1 (ru)
AT (1) ATE483688T1 (ru)
AU (1) AU2009208068B2 (ru)
BR (1) BRPI0903051A2 (ru)
CA (1) CA2676712C (ru)
CL (1) CL2009001758A1 (ru)
CY (1) CY1110943T1 (ru)
DE (1) DE602009000256D1 (ru)
DK (1) DK2166004T3 (ru)
EA (1) EA015777B1 (ru)
ES (1) ES2353251T3 (ru)
FR (1) FR2935381B1 (ru)
GE (1) GEP20125409B (ru)
HK (1) HK1141511A1 (ru)
HR (1) HRP20100679T1 (ru)
JO (1) JO2786B1 (ru)
MA (1) MA31228B1 (ru)
ME (1) ME00835B (ru)
MX (1) MX2009008443A (ru)
MY (1) MY145992A (ru)
NZ (1) NZ579270A (ru)
PA (1) PA8840901A1 (ru)
PE (1) PE20100234A1 (ru)
PL (1) PL2166004T3 (ru)
PT (1) PT2166004E (ru)
RS (1) RS51554B (ru)
SA (1) SA109300533B1 (ru)
SG (1) SG159454A1 (ru)
SI (1) SI2166004T1 (ru)
TW (1) TWI404705B (ru)
UA (1) UA105890C2 (ru)
UY (1) UY32034A (ru)
WO (1) WO2010023383A1 (ru)
ZA (1) ZA200905566B (ru)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2162438A4 (en) 2007-05-30 2011-07-06 Ind Swift Lab Ltd PROCESS FOR THE PREPARATION OF IVABRADINE HYDROCHLORIDE AND CORRESPONDING POLYMORPHIDE
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
CN101774969B (zh) * 2009-01-13 2012-07-04 江苏恒瑞医药股份有限公司 硫酸伊伐布雷定及其i型结晶的制备方法
HUP1000245A2 (en) * 2010-05-07 2011-11-28 Richter Gedeon Nyrt Industrial process for the production ivabradin salts
EP2522647B1 (en) * 2011-05-10 2014-04-30 DSM IP Assets B.V. Process of separating chiral isomers of chroman compounds and their derivatives and precursors
FR2984320B1 (fr) * 2011-12-20 2013-11-29 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR2984319B1 (fr) * 2011-12-20 2013-12-27 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
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
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
EP3101010A1 (en) 2015-06-03 2016-12-07 Urquima S.A. New method for the preparation of highly pure ivabradine base and salts thereof
CN106390519A (zh) * 2016-09-12 2017-02-15 华东理工大学 多柱模拟移动床色谱技术连续分离氨鲁米特外消旋体的方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5246948B2 (ru) * 1972-04-26 1977-11-29
IE52768B1 (en) * 1981-04-06 1988-02-17 Boots Co Ltd 1-arylcyclobutylalkylamine compounds useful as therapeutic agents
DE3119874A1 (de) * 1981-05-19 1982-12-09 Dr. Karl Thomae Gmbh, 7950 Biberach "benzazepinderivate, ihre herstellung und ihre verwendung als arzneimittel"
FR2539415B1 (fr) * 1983-01-14 1985-09-13 Adir Derives de la d-2 imidazoline, leur preparation et leur application en therapeutique
FR2681862B1 (fr) * 1991-09-27 1993-11-12 Adir Cie Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent.
US5269482A (en) * 1991-09-30 1993-12-14 Shearing Ernest J Protective enclosure apparatus for magnetic propulsion space vehicle
EP0977031B1 (en) * 1997-04-15 2009-04-29 Hideyuki Nishizawa Solid-liquid countercurrent extraction continuously separating apparatus
GB0325055D0 (en) * 2003-10-27 2003-12-03 Smithkline Beecham Corp New process
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
AU2007301436B2 (en) * 2006-09-29 2013-03-14 Council Of Scientific & Industrial Research Organic-inorganic hybrid chiral sorbent and process for the preparation thereof
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

Also Published As

Publication number Publication date
FR2935381B1 (fr) 2010-12-17
BRPI0903051A2 (pt) 2010-05-25
MY145992A (en) 2012-06-08
AU2009208068A1 (en) 2010-03-18
CN101659631B (zh) 2013-08-28
PA8840901A1 (es) 2010-04-21
TW201010980A (en) 2010-03-16
ZA200905566B (en) 2010-05-26
ES2353251T3 (es) 2011-02-28
PL2166004T3 (pl) 2011-03-31
KR101119309B1 (ko) 2012-03-19
CA2676712C (fr) 2012-09-18
CL2009001758A1 (es) 2010-12-24
SG159454A1 (en) 2010-03-30
DE602009000256D1 (de) 2010-11-18
US20130211070A1 (en) 2013-08-15
AU2009208068B2 (en) 2013-09-05
EP2166004A1 (fr) 2010-03-24
US8536365B2 (en) 2013-09-17
ME00835B (me) 2012-03-20
JP5663154B2 (ja) 2015-02-04
US8778930B2 (en) 2014-07-15
MA31228B1 (fr) 2010-03-01
HRP20100679T1 (hr) 2011-01-31
UY32034A (es) 2010-01-29
JP2013237675A (ja) 2013-11-28
US8927758B2 (en) 2015-01-06
EP2166004B1 (fr) 2010-10-06
GEP20125409B (en) 2012-02-27
TWI404705B (zh) 2013-08-11
ATE483688T1 (de) 2010-10-15
SA109300533B1 (ar) 2013-07-04
DK2166004T3 (da) 2011-01-10
CY1110943T1 (el) 2015-06-10
HK1141511A1 (en) 2010-11-12
CN101659631A (zh) 2010-03-03
JP2010065032A (ja) 2010-03-25
RS51554B (en) 2011-06-30
SI2166004T1 (sl) 2010-12-31
PE20100234A1 (es) 2010-03-27
AR073147A1 (es) 2010-10-13
US20130204032A1 (en) 2013-08-08
US20100056778A1 (en) 2010-03-04
JP5746733B2 (ja) 2015-07-08
UA105890C2 (ru) 2014-07-10
WO2010023383A1 (fr) 2010-03-04
EA015777B1 (ru) 2011-12-30
CA2676712A1 (fr) 2010-02-28
PT2166004E (pt) 2010-10-27
KR20100027025A (ko) 2010-03-10
MX2009008443A (es) 2010-03-23
FR2935381A1 (fr) 2010-03-05
JO2786B1 (en) 2014-03-15
NZ579270A (en) 2010-12-24

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