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AR093373A1 - Procedimiento de sintesis del (2e)-3-(3,4-dimetoxifenil)prop-2-enonitrilo y aplicacion a la sintesis de la ivabradina y de sus sales de adicion a un acido farmaceuticamente aceptable - Google Patents

Procedimiento de sintesis del (2e)-3-(3,4-dimetoxifenil)prop-2-enonitrilo y aplicacion a la sintesis de la ivabradina y de sus sales de adicion a un acido farmaceuticamente aceptable

Info

Publication number
AR093373A1
AR093373A1 ARP130104055A ARP130104055A AR093373A1 AR 093373 A1 AR093373 A1 AR 093373A1 AR P130104055 A ARP130104055 A AR P130104055A AR P130104055 A ARP130104055 A AR P130104055A AR 093373 A1 AR093373 A1 AR 093373A1
Authority
AR
Argentina
Prior art keywords
synthesis
compound
formula
ivabradine
pharmaceutically acceptable
Prior art date
Application number
ARP130104055A
Other languages
English (en)
Inventor
Sanchez Frederic
Lorenzo Gonzalez Jose
Del Pilar Carranza Maria
Isabel Garcia Aranda Maria
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
Publication of AR093373A1 publication Critical patent/AR093373A1/es

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00Preparation of carboxylic acid nitriles
    • C07C253/32Separation; Purification; Stabilisation; Use of additives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00Preparation of carboxylic acid nitriles
    • C07C253/30Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • 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
    • A61P9/08Vasodilators for multiple indications
    • 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
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44Palladium
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic acid nitriles
    • C07C255/01Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32Carboxylic 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
    • C07C255/34Carboxylic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D223/00Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/16Benzazepines; 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)
  • Cardiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (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)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

Procedimiento de síntesis del compuesto de fórmula (1). Aplicación en la síntesis de la ivabradina, de sus sales de adición a un ácido farmacéuticamente aceptable y de sus hidratos. Reivindicación 1: Procedimiento de síntesis del compuesto de fórmula (1) caracterizado porque el compuesto de fórmula (2) se somete a una reacción de acoplamiento con acrilonitrilo en presencia de un catalizador de paladio, de un ligando, de una base y de un agente de transferencia de fase en un disolvente orgánico para conducir al compuesto de fórmula (1). Reivindicación 13: Procedimiento según la reivindicación 1, caracterizado porque el compuesto de fórmula (1) obtenido se transforma a continuación en compuesto de fórmula (3) por una reacción de reducción, el cual se transforma en compuesto de fórmula (4) por una reacción de bromación.
ARP130104055A 2012-11-08 2013-11-06 Procedimiento de sintesis del (2e)-3-(3,4-dimetoxifenil)prop-2-enonitrilo y aplicacion a la sintesis de la ivabradina y de sus sales de adicion a un acido farmaceuticamente aceptable AR093373A1 (es)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
AR093373A1 true AR093373A1 (es) 2015-06-03

Family

ID=47598957

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP130104055A AR093373A1 (es) 2012-11-08 2013-11-06 Procedimiento de sintesis del (2e)-3-(3,4-dimetoxifenil)prop-2-enonitrilo y aplicacion a la sintesis de la ivabradina y de sus sales de adicion a un acido farmaceuticamente aceptable

Country Status (36)

Country Link
US (1) US8779122B2 (es)
EP (1) EP2730562B1 (es)
JP (2) JP6058519B2 (es)
KR (1) KR20140059731A (es)
CN (1) CN103804225B (es)
AR (1) AR093373A1 (es)
AU (1) AU2013245452C1 (es)
BR (1) BR102013028259A2 (es)
CA (1) CA2831289C (es)
CY (1) CY1116253T1 (es)
DK (1) DK2730562T3 (es)
EA (1) EA027080B1 (es)
ES (1) ES2539618T3 (es)
FR (1) FR2997696B1 (es)
GE (1) GEP20156308B (es)
HK (2) HK1193408A1 (es)
HR (1) HRP20150570T1 (es)
HU (1) HUE026525T2 (es)
JO (1) JO3189B1 (es)
MA (1) MA35147B1 (es)
MD (1) MD4392C1 (es)
ME (1) ME02120B (es)
MX (1) MX355590B (es)
MY (1) MY159701A (es)
NZ (1) NZ616768A (es)
PL (1) PL2730562T3 (es)
PT (1) PT2730562E (es)
RS (1) RS53993B1 (es)
SA (1) SA113350005B1 (es)
SG (1) SG2013077235A (es)
SI (1) SI2730562T1 (es)
TW (1) TWI488833B (es)
UA (1) UA118008C2 (es)
UY (1) UY35108A (es)
WO (1) WO2014072640A1 (es)
ZA (1) ZA201308001B (es)

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
CN117838881A (zh) 2017-08-31 2024-04-09 第一三共株式会社 制备抗体-药物缀合物的新方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5310598B2 (es) * 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
JP5435127B2 (ja) 2010-05-06 2014-03-05 株式会社島津製作所 材料試験機
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
SG2013077235A (en) 2014-06-27
TW201418197A (zh) 2014-05-16
BR102013028259A2 (pt) 2014-10-07
SI2730562T1 (sl) 2015-07-31
AU2013245452B2 (en) 2017-02-16
MD20130082A2 (en) 2014-05-31
ES2539618T3 (es) 2015-07-02
UY35108A (es) 2014-05-30
JO3189B1 (ar) 2018-03-08
AU2013245452A1 (en) 2014-05-22
KR20140059731A (ko) 2014-05-16
JP2016047837A (ja) 2016-04-07
US8779122B2 (en) 2014-07-15
MD4392B1 (ro) 2016-01-31
JP6058519B2 (ja) 2017-01-11
CA2831289C (en) 2016-02-09
PL2730562T3 (pl) 2015-08-31
GEP20156308B (en) 2015-06-25
MD4392C1 (ro) 2016-08-31
MX2013012858A (es) 2014-08-07
ME02120B (me) 2015-10-20
CA2831289A1 (en) 2014-05-08
CY1116253T1 (el) 2017-02-08
HK1193408A1 (en) 2014-09-19
PT2730562E (pt) 2015-05-20
EA201301136A3 (ru) 2014-07-30
CN103804225B (zh) 2016-02-17
US20140128598A1 (en) 2014-05-08
HK1198159A1 (zh) 2015-03-13
RS53993B1 (en) 2015-10-30
FR2997696B1 (fr) 2014-12-05
HRP20150570T1 (en) 2015-07-03
EP2730562B1 (fr) 2015-03-25
AU2013245452C1 (en) 2017-06-22
EP2730562A1 (fr) 2014-05-14
JP2014114275A (ja) 2014-06-26
FR2997696A1 (fr) 2014-05-09
NZ616768A (en) 2015-02-27
EA027080B1 (ru) 2017-06-30
EA201301136A2 (ru) 2014-05-30
SA113350005B1 (ar) 2015-12-06
MY159701A (en) 2017-01-13
TWI488833B (zh) 2015-06-21
WO2014072640A1 (fr) 2014-05-15
MX355590B (es) 2018-04-24
DK2730562T3 (en) 2015-06-29
HUE026525T2 (en) 2016-06-28
MA35147B1 (fr) 2014-06-02
CN103804225A (zh) 2014-05-21
ZA201308001B (en) 2014-07-30
UA118008C2 (uk) 2018-11-12

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