EG23719A - New process for the synthesis of (I S)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane and addition salts thereof, and application in the synthesis of I V abradine and addition salts thereof witha pharmaceutically acceptable acid - Google Patents

New process for the synthesis of (I S)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane and addition salts thereof, and application in the synthesis of I V abradine and addition salts thereof witha pharmaceutically acceptable acid

Info

Publication number
EG23719A
EG23719A EG2005020088A EG2005020088A EG23719A EG 23719 A EG23719 A EG 23719A EG 2005020088 A EG2005020088 A EG 2005020088A EG 2005020088 A EG2005020088 A EG 2005020088A EG 23719 A EG23719 A EG 23719A
Authority
EG
Egypt
Prior art keywords
synthesis
addition salts
abradine
benzocyclobutane
methylaminomethyl
Prior art date
Application number
EG2005020088A
Other languages
English (en)
Inventor
Jean M Lerestif
Original Assignee
Servier Lab
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 Servier Lab filed Critical Servier Lab
Application granted granted Critical
Publication of EG23719A publication Critical patent/EG23719A/xx

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54Compounds 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
    • C07C217/56Compounds 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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/58Compounds 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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/10Separation; Purification; Stabilisation; Use of additives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/04Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/06Antiarrhythmics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EG2005020088A 2004-05-19 2005-02-19 New process for the synthesis of (I S)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane and addition salts thereof, and application in the synthesis of I V abradine and addition salts thereof witha pharmaceutically acceptable acid EG23719A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0405453A FR2870537A1 (fr) 2004-05-19 2004-05-19 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

Publications (1)

Publication Number Publication Date
EG23719A true EG23719A (en) 2007-06-17

Family

ID=34941962

Family Applications (1)

Application Number Title Priority Date Filing Date
EG2005020088A EG23719A (en) 2004-05-19 2005-02-19 New process for the synthesis of (I S)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane and addition salts thereof, and application in the synthesis of I V abradine and addition salts thereof witha pharmaceutically acceptable acid

Country Status (33)

Country Link
US (1) US6982350B2 (de)
EP (1) EP1598333B1 (de)
JP (1) JP4148952B2 (de)
KR (1) KR100649289B1 (de)
CN (1) CN1332933C (de)
AR (1) AR047746A1 (de)
AT (1) ATE342885T1 (de)
AU (1) AU2005200883B2 (de)
BR (1) BRPI0500480B8 (de)
CA (1) CA2496708C (de)
CY (1) CY1105826T1 (de)
DE (1) DE602005000187T2 (de)
DK (1) DK1598333T3 (de)
EA (1) EA007746B1 (de)
EG (1) EG23719A (de)
ES (1) ES2275258T3 (de)
FR (1) FR2870537A1 (de)
GE (1) GEP20074135B (de)
HK (1) HK1081945A1 (de)
HR (1) HRP20060449T3 (de)
MA (1) MA27640A1 (de)
ME (1) ME01395B (de)
MX (1) MXPA05005139A (de)
MY (1) MY139475A (de)
NO (1) NO330968B1 (de)
NZ (1) NZ538329A (de)
PL (1) PL1598333T3 (de)
PT (1) PT1598333E (de)
RS (1) RS50512B (de)
SI (1) SI1598333T1 (de)
UA (1) UA79482C2 (de)
WO (1) WO2005123659A1 (de)
ZA (1) ZA200501469B (de)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2097383B1 (de) * 2006-11-30 2012-02-08 Cadila Healthcare Limited Verfahren zur Herstellung von Ivabradinhydrochlorid
PT2471780E (pt) 2007-05-30 2015-02-24 Ind Swift Lab Ltd Sais oxalato de ivabradina cristalinos e seus polimorfos
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
FR2927900B1 (fr) * 2008-02-27 2010-09-17 Clariant Specialty Fine Chem Procede de preparation d'alpha-aminoacetals optiquement actifs.
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
CN102264689B (zh) * 2008-12-22 2014-12-31 新梅斯托克尔卡公司 制备伊伐布雷定的方法
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.
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
EP2534135A2 (de) 2010-02-12 2012-12-19 KRKA, D.D., Novo Mesto Neuartige ivabradinhydrochloridformen
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
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
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
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
FR2988720B1 (fr) * 2012-03-27 2014-03-14 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
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
CN103848789B (zh) * 2012-11-29 2016-05-18 江苏恒瑞医药股份有限公司 一种伊伐布雷定的制备方法
FR3003859B1 (fr) * 2013-03-26 2015-03-13 Servier Lab "procede de synthese de derives de la 7,8-dimethoxy-1,3-dihydro-2h-3-benzazepin-2-one et application a la synthese de l'ivabradine"
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"
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
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
WO2015119057A1 (ja) * 2014-02-06 2015-08-13 宇部興産株式会社 インドリン化合物の製造方法
EP3101010A1 (de) 2015-06-03 2016-12-07 Urquima S.A. Neues verfahren zur herstellung von hochreinem ivabradine und dessen salzen
CN110483312A (zh) * 2019-08-27 2019-11-22 北京阳光诺和药物研究有限公司 一种高纯度盐酸伊伐布雷定及其中间体的制备方法
CN115286577B (zh) * 2022-08-25 2023-10-20 江苏永安制药有限公司 一种盐酸伊伐布雷定及其中间体的制备方法

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Publication number Priority date Publication date Assignee Title
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"
EP0072061B1 (de) * 1981-08-05 1985-05-15 FISONS plc Aminderivate, Verfahren zu deren Produktion und diese enthaltende pharmazeutische Zusammensetzungen
JP2823679B2 (ja) * 1990-05-08 1998-11-11 東レ株式会社 光学活性2―メチルピペラジンの製造方法
FR2681862B1 (fr) * 1991-09-27 1993-11-12 Adir Cie Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent.
JPH083120A (ja) 1994-06-21 1996-01-09 Ajinomoto Co Inc アシル−アミノ酸とα−アリールアミンとの付加塩及びα−アリールアミンの光学分割法
JPH09208546A (ja) * 1995-11-29 1997-08-12 Ajinomoto Co Inc 新規置換ベンジルアミンの付加塩及びその光学分割法

Also Published As

Publication number Publication date
NZ538329A (en) 2005-10-28
WO2005123659A1 (fr) 2005-12-29
BRPI0500480A (pt) 2006-06-06
JP4148952B2 (ja) 2008-09-10
AU2005200883B2 (en) 2010-07-15
HK1081945A1 (en) 2006-05-26
EA007746B1 (ru) 2006-12-29
ES2275258T3 (es) 2007-06-01
PT1598333E (pt) 2007-01-31
BRPI0500480B1 (pt) 2020-08-11
US6982350B2 (en) 2006-01-03
CY1105826T1 (el) 2011-02-02
GEP20074135B (en) 2007-06-25
FR2870537A1 (fr) 2005-11-25
NO20050883D0 (no) 2005-02-18
MXPA05005139A (es) 2005-11-24
MA27640A1 (fr) 2005-12-01
MY139475A (en) 2009-10-30
NO330968B1 (no) 2011-08-29
CA2496708A1 (fr) 2005-11-19
AU2005200883A1 (en) 2005-12-08
ZA200501469B (en) 2005-11-30
NO20050883L (no) 2005-11-21
CN1332933C (zh) 2007-08-22
HRP20060449T3 (en) 2007-03-31
CA2496708C (fr) 2011-03-15
RS50512B (sr) 2010-03-02
ME01395B (de) 2010-03-02
CN1699331A (zh) 2005-11-23
SI1598333T1 (sl) 2007-02-28
EP1598333B1 (de) 2006-10-18
DE602005000187D1 (de) 2006-11-30
KR20060042118A (ko) 2006-05-12
EA200500239A1 (ru) 2005-12-29
DK1598333T3 (da) 2007-02-12
DE602005000187T2 (de) 2007-09-06
US20050261376A1 (en) 2005-11-24
ATE342885T1 (de) 2006-11-15
KR100649289B1 (ko) 2006-11-24
BRPI0500480B8 (pt) 2021-05-25
AR047746A1 (es) 2006-02-15
PL1598333T3 (pl) 2006-12-29
JP2005330263A (ja) 2005-12-02
EP1598333A1 (de) 2005-11-23
UA79482C2 (en) 2007-06-25

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