CA2831289C - New process for the synthesis of (2e)-3(3,4-dimethoxyphenyl)prop-2-enenitrile, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid - Google Patents

New process for the synthesis of (2e)-3(3,4-dimethoxyphenyl)prop-2-enenitrile, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid Download PDF

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Publication number
CA2831289C
CA2831289C CA2831289A CA2831289A CA2831289C CA 2831289 C CA2831289 C CA 2831289C CA 2831289 A CA2831289 A CA 2831289A CA 2831289 A CA2831289 A CA 2831289A CA 2831289 C CA2831289 C CA 2831289C
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compound
formula
acid
conversion
carry out
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Expired - Fee Related
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CA2831289A
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English (en)
French (fr)
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CA2831289A1 (en
Inventor
Maria Del Pilar Carranza
Maria Isabel Garcia Aranda
Jose Lorenzo Gonzalez
Frederic Sanchez
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Les Laboratoires Servier SAS
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Les Laboratoires Servier SAS
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    • 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
    • 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
    • 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
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • 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
    • A61P9/06—Antiarrhythmics
    • 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
    • A61P9/08—Vasodilators for multiple indications
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/34—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
    • 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

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  • 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)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Catalysts (AREA)
CA2831289A 2012-11-08 2013-10-24 New process for the synthesis of (2e)-3(3,4-dimethoxyphenyl)prop-2-enenitrile, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid Expired - Fee Related CA2831289C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1260576A FR2997696B1 (fr) 2012-11-08 2012-11-08 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
FR12/60576 2012-11-08

Publications (2)

Publication Number Publication Date
CA2831289A1 CA2831289A1 (en) 2014-05-08
CA2831289C true CA2831289C (en) 2016-02-09

Family

ID=47598957

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2831289A Expired - Fee Related CA2831289C (en) 2012-11-08 2013-10-24 New process for the synthesis of (2e)-3(3,4-dimethoxyphenyl)prop-2-enenitrile, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid

Country Status (35)

Country Link
US (1) US8779122B2 (enExample)
EP (1) EP2730562B1 (enExample)
JP (2) JP6058519B2 (enExample)
KR (1) KR20140059731A (enExample)
CN (1) CN103804225B (enExample)
AR (1) AR093373A1 (enExample)
AU (1) AU2013245452C1 (enExample)
BR (1) BR102013028259A2 (enExample)
CA (1) CA2831289C (enExample)
CY (1) CY1116253T1 (enExample)
DK (1) DK2730562T3 (enExample)
EA (1) EA027080B1 (enExample)
ES (1) ES2539618T3 (enExample)
FR (1) FR2997696B1 (enExample)
GE (1) GEP20156308B (enExample)
HR (1) HRP20150570T1 (enExample)
HU (1) HUE026525T2 (enExample)
JO (1) JO3189B1 (enExample)
MA (1) MA35147B1 (enExample)
MD (1) MD4392C1 (enExample)
ME (1) ME02120B (enExample)
MX (1) MX355590B (enExample)
MY (1) MY159701A (enExample)
NZ (1) NZ616768A (enExample)
PL (1) PL2730562T3 (enExample)
PT (1) PT2730562E (enExample)
RS (1) RS53993B1 (enExample)
SA (1) SA113350005B1 (enExample)
SG (1) SG2013077235A (enExample)
SI (1) SI2730562T1 (enExample)
TW (1) TWI488833B (enExample)
UA (1) UA118008C2 (enExample)
UY (1) UY35108A (enExample)
WO (1) WO2014072640A1 (enExample)
ZA (1) ZA201308001B (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3101010A1 (en) 2015-06-03 2016-12-07 Urquima S.A. New method for the preparation of highly pure ivabradine base and salts thereof
CN105541605A (zh) * 2016-02-04 2016-05-04 扬州大学 一种轴手性联萘配体前体(s)-2,2’-二羧酸-1,1’-联萘的合成方法
SG11202001514XA (en) 2017-08-31 2020-03-30 Daiichi Sankyo Co Ltd Novel method for producing antibody-drug conjugate

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5310598B2 (enExample) * 1972-01-28 1978-04-14
JPH0753692B2 (ja) * 1990-10-30 1995-06-07 工業技術院長 芳香族カルボン酸エステル類の製造方法
FR2681862B1 (fr) * 1991-09-27 1993-11-12 Adir Cie Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent.
DE4333711A1 (de) * 1993-10-02 1995-04-06 Hoechst Ag 2,4,5-Trihalogenzimtsäurenitrile und Verfahren zu ihrer Herstellung
DE10159270A1 (de) * 2001-12-03 2003-06-12 Bayer Ag Verfahren zur Arylierung von Olefinen
WO2005123662A1 (en) * 2004-06-18 2005-12-29 Janssen Pharmaceutica N.V. Modified heck reaction
CN101407474B (zh) * 2008-11-18 2011-12-14 东华大学 一种2-溴-4,5-二甲氧基苯丙腈的制备方法
CN102884410B (zh) 2010-05-06 2015-05-27 株式会社岛津制作所 材料试验机
HUP1000245A2 (en) * 2010-05-07 2011-11-28 Richter Gedeon Nyrt Industrial process for the production ivabradin salts
CN102464595B (zh) * 2010-11-17 2015-02-25 山东新时代药业有限公司 一种伊伐布雷定中间体的合成方法

Also Published As

Publication number Publication date
MY159701A (en) 2017-01-13
US20140128598A1 (en) 2014-05-08
EA201301136A3 (ru) 2014-07-30
JP2016047837A (ja) 2016-04-07
PT2730562E (pt) 2015-05-20
FR2997696A1 (fr) 2014-05-09
NZ616768A (en) 2015-02-27
EA027080B1 (ru) 2017-06-30
EA201301136A2 (ru) 2014-05-30
CN103804225A (zh) 2014-05-21
ZA201308001B (en) 2014-07-30
KR20140059731A (ko) 2014-05-16
WO2014072640A1 (fr) 2014-05-15
AU2013245452C1 (en) 2017-06-22
DK2730562T3 (en) 2015-06-29
RS53993B1 (sr) 2015-10-30
AU2013245452B2 (en) 2017-02-16
ME02120B (me) 2015-10-20
HK1193408A1 (en) 2014-09-19
EP2730562B1 (fr) 2015-03-25
UA118008C2 (uk) 2018-11-12
AR093373A1 (es) 2015-06-03
BR102013028259A2 (pt) 2014-10-07
MD20130082A2 (en) 2014-05-31
TW201418197A (zh) 2014-05-16
ES2539618T3 (es) 2015-07-02
HRP20150570T1 (en) 2015-07-03
MX2013012858A (es) 2014-08-07
CY1116253T1 (el) 2017-02-08
JP2014114275A (ja) 2014-06-26
AU2013245452A1 (en) 2014-05-22
PL2730562T3 (pl) 2015-08-31
JP6058519B2 (ja) 2017-01-11
MX355590B (es) 2018-04-24
MD4392B1 (ro) 2016-01-31
SG2013077235A (en) 2014-06-27
HUE026525T2 (en) 2016-06-28
MD4392C1 (ro) 2016-08-31
SI2730562T1 (sl) 2015-07-31
GEP20156308B (en) 2015-06-25
CA2831289A1 (en) 2014-05-08
SA113350005B1 (ar) 2015-12-06
JO3189B1 (ar) 2018-03-08
MA35147B1 (fr) 2014-06-02
FR2997696B1 (fr) 2014-12-05
UY35108A (es) 2014-05-30
US8779122B2 (en) 2014-07-15
TWI488833B (zh) 2015-06-21
CN103804225B (zh) 2016-02-17
HK1198159A1 (zh) 2015-03-13
EP2730562A1 (fr) 2014-05-14

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