MD4335C1 - Procedeu de sinteză a 3-(2-bromo-4,5-dimetoxifenil)propannitril şi procedeu de sinteză a ivabradinei şi a sărurilor sale cu utilizarea acestuia - Google Patents

Procedeu de sinteză a 3-(2-bromo-4,5-dimetoxifenil)propannitril şi procedeu de sinteză a ivabradinei şi a sărurilor sale cu utilizarea acestuia

Info

Publication number
MD4335C1
MD4335C1 MDA20130071A MD20130071A MD4335C1 MD 4335 C1 MD4335 C1 MD 4335C1 MD A20130071 A MDA20130071 A MD A20130071A MD 20130071 A MD20130071 A MD 20130071A MD 4335 C1 MD4335 C1 MD 4335C1
Authority
MD
Moldova
Prior art keywords
synthesis
ivabradine
compound
formula
propanenitrile
Prior art date
Application number
MDA20130071A
Other languages
English (en)
Russian (ru)
Other versions
MD4335B1 (ro
MD20130071A2 (ro
Inventor
Мария дель Пилар КАРРАНСА
АРАНДА Мария Изабель ГАРСИЯ
Жозе Лоренсо ГОНСАЛЕС
Фредерик Санчес
Original Assignee
Les Laboratoires Servier
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=47356189&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=MD4335(C1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Les Laboratoires Servier filed Critical Les Laboratoires Servier
Publication of MD20130071A2 publication Critical patent/MD20130071A2/ro
Publication of MD4335B1 publication Critical patent/MD4335B1/ro
Publication of MD4335C1 publication Critical patent/MD4335C1/ro

Links

Classifications

    • 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
    • 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
    • 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

Abstract

Invenţia se referă la un procedeu de sinteză a compusului cu formula (I):care constă în aceea că compusul cu formula (VIII):este supus acţiunii N-bromosuccinimidei în prezenţa unui solvent organic pentru a obţine compusul cu formula (I).Invenţia se referă, de asemenea, la un procedeu de sinteză a ivabradinei, sărurilor sale acceptabile farmaceutic şi hidraţilor acestora, cu utilizarea compusului cu formula (I). Procedeul menţionat asigură un procent înalt al randamentului produsului finit.
MDA20130071A 2012-10-12 2013-10-08 Procedeu de sinteză a 3-(2-bromo-4,5-dimetoxifenil)propannitril şi procedeu de sinteză a ivabradinei şi a sărurilor sale cu utilizarea acestuia MD4335C1 (ro)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1259745A FR2996845A1 (fr) 2012-10-12 2012-10-12 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

Publications (3)

Publication Number Publication Date
MD20130071A2 MD20130071A2 (ro) 2014-04-30
MD4335B1 MD4335B1 (ro) 2015-03-31
MD4335C1 true MD4335C1 (ro) 2015-10-31

Family

ID=47356189

Family Applications (1)

Application Number Title Priority Date Filing Date
MDA20130071A MD4335C1 (ro) 2012-10-12 2013-10-08 Procedeu de sinteză a 3-(2-bromo-4,5-dimetoxifenil)propannitril şi procedeu de sinteză a ivabradinei şi a sărurilor sale cu utilizarea acestuia

Country Status (35)

Country Link
US (1) US8779121B2 (ro)
EP (1) EP2719689B1 (ro)
JP (1) JP5793171B2 (ro)
KR (1) KR101567887B1 (ro)
CN (1) CN103724228B (ro)
AR (1) AR092983A1 (ro)
AU (1) AU2013237671C1 (ro)
BR (1) BR102013026030A2 (ro)
CA (1) CA2829428C (ro)
CY (1) CY1117315T1 (ro)
DK (1) DK2719689T3 (ro)
EA (1) EA024408B1 (ro)
ES (1) ES2564959T3 (ro)
FR (1) FR2996845A1 (ro)
GE (1) GEP20156320B (ro)
HK (2) HK1191318A1 (ro)
HR (1) HRP20160200T1 (ro)
HU (1) HUE027867T2 (ro)
MA (1) MA35597B1 (ro)
MD (1) MD4335C1 (ro)
ME (1) ME02329B (ro)
MX (1) MX2013011705A (ro)
MY (1) MY160147A (ro)
NZ (1) NZ616558A (ro)
PL (1) PL2719689T3 (ro)
PT (1) PT2719689E (ro)
RS (1) RS54536B1 (ro)
SA (1) SA113340924B1 (ro)
SG (1) SG2013074570A (ro)
SI (1) SI2719689T1 (ro)
TW (1) TWI500597B (ro)
UA (1) UA117655C2 (ro)
UY (1) UY35068A (ro)
WO (1) WO2014057228A1 (ro)
ZA (1) ZA201307601B (ro)

Families Citing this family (1)

* 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

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DE2303919A1 (de) * 1972-01-28 1973-08-02 Nisshin Flour Milling Co Verfahren zur herstellung von benzylpyrimidinderivaten
US4618683A (en) * 1982-06-01 1986-10-21 Abbott Laboratories Tetrahydro-6,7-dimethoxy-1H-benz[e]isoinodolines useful in the treatment of hypertension and as sedatives
EP0534859A1 (fr) * 1991-09-27 1993-03-31 Adir Et Compagnie 3-Benzazépin-zones substituées par un groupe benzocyclobutyl- ou indanyl-alkyl-amino-alkyle, utiles dans le traitement des affections cardiovasculaires
CN101407474A (zh) * 2008-11-18 2009-04-15 东华大学 一种2-溴-4,5-二甲氧基苯丙腈的制备方法
WO2011008597A1 (en) * 2009-07-14 2011-01-20 Schering Corporation Dihydroimidazoisoquinoline derivatives useful as pde10 inhibitors
WO2011138625A1 (en) * 2010-05-07 2011-11-10 Richter Gedeon Nyrt. Industrial process for the synthesis of ivabradine salts

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EP0043194A3 (en) * 1980-06-19 1982-03-31 FISONS plc Bicyclo-octatriene derivatives, pharmaceutical compositions containing them and processes and intermediates for their production
JPS61130253A (ja) * 1984-11-28 1986-06-18 Otsuka Pharmaceut Factory Inc ナフトキノン誘導体
US5112836A (en) * 1989-06-19 1992-05-12 Kyorin Pharmaceutical Co., Ltd. Cyclic anthranililc acid carboxylic acid derivatives and medical therapeutic use thereof
JPH06263688A (ja) * 1991-09-04 1994-09-20 Otsuka Pharmaceut Factory Inc フェナンスレン誘導体
JP3186419B2 (ja) * 1993-03-26 2001-07-11 富士レビオ株式会社 ４−フルオロビフェニル誘導体
CN1228775A (zh) * 1996-05-14 1999-09-15 葛兰素集团有限公司 作为时间生物学药物的苯并呋喃和苯并吡喃
FR2763588B1 (fr) * 1997-05-23 1999-07-09 Cird Galderma Composes triaromatiques, compositions les contenant et utilisations
SK2792004A3 (en) * 2001-12-13 2004-11-03 Egyt Gyogyszervegyeszeti Gyar Process for the preparation of tofisopam and new intermediates
DK1569912T3 (en) * 2002-12-03 2015-06-29 Pharmacyclics Inc 2- (2-hydroxybiphenyl-3-yl) -1h-benzoimidazole-5-carboxamidine derivatives as factor VIIa inhibitors.
KR100613810B1 (ko) * 2004-12-17 2006-08-17 주식회사 두산 전계 발광 소자용 화합물 및 이를 포함하는 유기 전계발광소자

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2303919A1 (de) * 1972-01-28 1973-08-02 Nisshin Flour Milling Co Verfahren zur herstellung von benzylpyrimidinderivaten
US4618683A (en) * 1982-06-01 1986-10-21 Abbott Laboratories Tetrahydro-6,7-dimethoxy-1H-benz[e]isoinodolines useful in the treatment of hypertension and as sedatives
EP0534859A1 (fr) * 1991-09-27 1993-03-31 Adir Et Compagnie 3-Benzazépin-zones substituées par un groupe benzocyclobutyl- ou indanyl-alkyl-amino-alkyle, utiles dans le traitement des affections cardiovasculaires
CN101407474A (zh) * 2008-11-18 2009-04-15 东华大学 一种2-溴-4,5-二甲氧基苯丙腈的制备方法
WO2011008597A1 (en) * 2009-07-14 2011-01-20 Schering Corporation Dihydroimidazoisoquinoline derivatives useful as pde10 inhibitors
WO2011138625A1 (en) * 2010-05-07 2011-11-10 Richter Gedeon Nyrt. Industrial process for the synthesis of ivabradine salts

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Kametani T., Ogasawara K., Takasashi T. Studies of the syntheses of heterocyclic compounds - CDXCIV: A total synthesis of (±)-xylopinine by thermolysis. Tetrahedron 1973, v. 29, p. 73-76 *
Kenneth D. Paull, Cheng C. C. Facile synthesis of 4-substituted 3a,4,5,9b-tetrahydrobenz[e]isoindoline. The Journal of Organic Chemistry, 1972, vol. 37 (21), p. 3374-3376 *
Reginald H. Mitchell, Yee-Hing Lai, Richard V. Williams. N-bromosuccinimide-Dimethylformamide: A mild selective nuclear monobromination reagent for reactive aromatic compounds. The Journal of Organic Chemistry, 1979, v. 44, 25, p. 4733-4735 (regăsit în Internet la 2014.09.03 URL:< <http://pubs.acs.org/doi/abs/10.1021/jo00393a066>>) *
Zhao Sheng Yin, Liang Hong Yu, Shao Zhi Yu, Chen Rui. A practical synthesis of 1-cyano-4,5-dimethoxybenzocyclobutene. Journal of Chemical Research, 2009, 7, p. 420-422 *

Also Published As

Publication number Publication date
EP2719689A1 (fr) 2014-04-16
MY160147A (en) 2017-02-28
SG2013074570A (en) 2014-05-29
KR101567887B1 (ko) 2015-11-10
US20140107334A1 (en) 2014-04-17
US8779121B2 (en) 2014-07-15
AU2013237671B2 (en) 2017-03-02
CA2829428A1 (fr) 2014-04-12
GEP20156320B (en) 2015-07-10
AU2013237671C1 (en) 2017-06-15
HK1193409A1 (zh) 2014-09-19
UY35068A (es) 2014-05-30
EA201301020A1 (ru) 2014-06-30
WO2014057228A1 (fr) 2014-04-17
MX2013011705A (es) 2014-04-25
KR20140047538A (ko) 2014-04-22
SA113340924B1 (ar) 2015-07-09
FR2996845A1 (fr) 2014-04-18
NZ616558A (en) 2014-10-31
HUE027867T2 (en) 2016-11-28
AU2013237671A1 (en) 2014-05-01
HRP20160200T1 (hr) 2016-03-25
PT2719689E (pt) 2016-02-04
UA117655C2 (uk) 2018-09-10
TW201414705A (zh) 2014-04-16
MD4335B1 (ro) 2015-03-31
MD20130071A2 (ro) 2014-04-30
HK1191318A1 (zh) 2014-07-25
RS54536B1 (en) 2016-06-30
JP2014080421A (ja) 2014-05-08
ZA201307601B (en) 2014-07-30
MA35597B1 (fr) 2014-11-01
AR092983A1 (es) 2015-05-13
PL2719689T3 (pl) 2016-08-31
CY1117315T1 (el) 2017-04-26
DK2719689T3 (en) 2016-03-29
SI2719689T1 (sl) 2016-04-29
ME02329B (me) 2016-06-20
ES2564959T3 (es) 2016-03-30
TWI500597B (zh) 2015-09-21
CN103724228B (zh) 2016-04-20
EP2719689B1 (fr) 2015-12-23
JP5793171B2 (ja) 2015-10-14
CA2829428C (fr) 2016-04-19
BR102013026030A2 (pt) 2014-10-29
EA024408B1 (ru) 2016-09-30
CN103724228A (zh) 2014-04-16

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