MD4336C1 - Procedeu nou de sinteză a ivabradinei şi a sărurilor de adiţie cu un acid acceptabil farmaceutic - Google Patents

Procedeu nou de sinteză a ivabradinei şi a sărurilor de adiţie cu un acid acceptabil farmaceutic

Info

Publication number
MD4336C1
MD4336C1 MDA20120094A MD20120094A MD4336C1 MD 4336 C1 MD4336 C1 MD 4336C1 MD A20120094 A MDA20120094 A MD A20120094A MD 20120094 A MD20120094 A MD 20120094A MD 4336 C1 MD4336 C1 MD 4336C1
Authority
MD
Moldova
Prior art keywords
ivabradine
synthesis
pharmaceutically acceptable
addition salts
acceptable acid
Prior art date
Application number
MDA20120094A
Other languages
English (en)
Russian (ru)
Other versions
MD4336B1 (ro
Inventor
Жан-Люк Рено
Николас ПАННЕТЬЕ
Жан-Пьер Лекув
Люсиль Весс-Людо
Соленн МУЛЕН
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=47115640&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=MD4336(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 MD4336B1 publication Critical patent/MD4336B1/ro
Publication of MD4336C1 publication Critical patent/MD4336C1/ro

Links

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
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • 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
    • A61P9/10—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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • 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

Prezenta invenţie se referă la sinteza ivabradinei cu formula (I):Ivabradina se obţine în urma aminării reductive catalitice a compusului (V) cu amina (VI) sub presiune de hidrogen într-un solvent organic şi, opţional, în prezenţa N-oxidului de trimetilamină:În calitate de catalizator se utilizează compuşi metaloorganici pe bază de fier, derivaţi de ciclopentadienă şi monoxid de carbon.Procedeul dat permite de a exclude în sinteza ivabradinei utilizarea catalizatorilor pe bază de metale preţioase, aşa ca paladiul.
MDA20120094A 2011-12-20 2012-10-31 Procedeu nou de sinteză a ivabradinei şi a sărurilor de adiţie cu un acid acceptabil farmaceutic MD4336C1 (ro)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1103933A FR2984319B1 (fr) 2011-12-20 2011-12-20 Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable

Publications (2)

Publication Number Publication Date
MD4336B1 MD4336B1 (ro) 2015-03-31
MD4336C1 true MD4336C1 (ro) 2015-10-31

Family

ID=47115640

Family Applications (1)

Application Number Title Priority Date Filing Date
MDA20120094A MD4336C1 (ro) 2011-12-20 2012-10-31 Procedeu nou de sinteză a ivabradinei şi a sărurilor de adiţie cu un acid acceptabil farmaceutic

Country Status (35)

Country Link
US (1) US8513410B2 (ro)
EP (1) EP2607353B1 (ro)
JP (1) JP5670406B2 (ro)
KR (1) KR101470879B1 (ro)
CN (1) CN103172566B (ro)
AR (1) AR088678A1 (ro)
AU (1) AU2012244188B2 (ro)
BR (1) BR102012028614A2 (ro)
CA (1) CA2795741C (ro)
CL (1) CL2012003136A1 (ro)
CY (1) CY1115682T1 (ro)
DK (1) DK2607353T3 (ro)
EA (1) EA026510B1 (ro)
ES (1) ES2525032T3 (ro)
FR (1) FR2984319B1 (ro)
GE (1) GEP20156350B (ro)
HK (1) HK1186733A1 (ro)
HR (1) HRP20141023T1 (ro)
JO (1) JO3031B1 (ro)
MA (1) MA34276B1 (ro)
MD (1) MD4336C1 (ro)
MX (1) MX2012012938A (ro)
MY (1) MY170662A (ro)
PE (1) PE20131097A1 (ro)
PL (1) PL2607353T3 (ro)
PT (1) PT2607353E (ro)
RS (1) RS53541B1 (ro)
SA (1) SA112330994B1 (ro)
SG (1) SG191471A1 (ro)
SI (1) SI2607353T1 (ro)
TW (1) TWI440627B (ro)
UA (1) UA111329C2 (ro)
UY (1) UY34423A (ro)
WO (1) WO2013093220A1 (ro)
ZA (1) ZA201208160B (ro)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN105669554A (zh) * 2016-02-22 2016-06-15 徐建立 一种盐酸伊伐布雷定杂质及其制备方法和应用
FR3071833B1 (fr) * 2017-09-29 2020-01-03 Universite Paris-Sud Nouveau procede de synthese d'amines tertiaires dissymetriques

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO1999054337A1 (en) * 1998-04-17 1999-10-28 Symyx Technologies Ancillary ligands and metal complexes thereof
WO2000020377A1 (en) * 1998-10-08 2000-04-13 Symyx Technologies Catalyst ligands, catalytic metal complexes and processes using same
EP1589005A1 (fr) * 2004-04-13 2005-10-26 Les Laboratoires Servier Procédé de synthèse de l'ivabradine et de ses sels d'addition à un acide pharmaceutiquement acceptable
EP1595888A1 (en) * 2004-05-11 2005-11-16 Degussa AG Cycloolefin phosphine ligands and their use in catalysis
EP2202225A1 (fr) * 2008-12-24 2010-06-30 Les Laboratoires Servier Nouveau procédé de synthèse de l'ivabradine et de ses sels d'addition à un acide pharmaceutiquemenet acceptable

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2381771T3 (es) * 2006-11-30 2012-05-31 Cadila Healthcare Limited Procedimiento para la preparación de hidrocloruro de ivabradina
KR101478855B1 (ko) * 2007-05-30 2015-01-02 인드-스위프트 래버러토리즈 리미티드 이바브라딘 히드로클로라이드 및 그의 다형태의 제조방법
US7857994B2 (en) 2007-05-30 2010-12-28 GE Lighting Solutions, LLC Green emitting phosphors and blends thereof
FR2920773B1 (fr) * 2007-09-11 2009-10-23 Servier Lab Derives de 1,2,4,5-tetrahydro-3h-benzazepines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
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
FR2941695B1 (fr) * 2009-02-04 2011-02-18 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO1999054337A1 (en) * 1998-04-17 1999-10-28 Symyx Technologies Ancillary ligands and metal complexes thereof
WO2000020377A1 (en) * 1998-10-08 2000-04-13 Symyx Technologies Catalyst ligands, catalytic metal complexes and processes using same
EP1589005A1 (fr) * 2004-04-13 2005-10-26 Les Laboratoires Servier Procédé de synthèse de l'ivabradine et de ses sels d'addition à un acide pharmaceutiquement acceptable
EP1595888A1 (en) * 2004-05-11 2005-11-16 Degussa AG Cycloolefin phosphine ligands and their use in catalysis
EP2202225A1 (fr) * 2008-12-24 2010-06-30 Les Laboratoires Servier Nouveau procédé de synthèse de l'ivabradine et de ses sels d'addition à un acide pharmaceutiquemenet acceptable

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Beller M. et al. Chem Asian J., 2011, vol. 6, p.2240-2245 *
Bhanage B.M. et al Tetr. Lett. 2008, vol. 49, p.965-969 *
Hiroshi Nakazawa and Masumi Itazaki. "Fe-H Complexes in Catalysis". In Topp. Organomet. Chem. (2011), 33: 27-81, (Iron Catalysis: Fundamentals and Applications, volume editors B.Plietker and M. Beller. Springer-Verlag, Berlin Heidelberg, 2011). DOI: 10.1007/978-3-642-14670-1_2 regăsit în Internet la 2014.11.21, url ("Download sample page 1"): www.springer.com/.../9783642146695-c1.pdf Vezi pag. 59, referinţa /144/ şi Schema 42 *
Stephen Enthaler. Synthesis of secondary amines by iron-catalyzed reductive amination. ChemCatChem, 2010, vol. 2, pag. 1411-1415, DOI: 10.1002/cctc.201000180, regăsit în Internet la 2014.11.19, url: http://140.123.79.90/~seekwei/thesis-reference/26-1411_ftp.pdf vezi întregul document. *

Also Published As

Publication number Publication date
SG191471A1 (en) 2013-07-31
ZA201208160B (en) 2013-06-26
RS53541B1 (en) 2015-02-27
ES2525032T3 (es) 2014-12-16
CN103172566A (zh) 2013-06-26
MX2012012938A (es) 2013-06-19
JP5670406B2 (ja) 2015-02-18
CA2795741C (fr) 2015-09-08
CA2795741A1 (fr) 2013-06-20
CN103172566B (zh) 2015-11-18
TWI440627B (zh) 2014-06-11
DK2607353T3 (en) 2014-12-08
UY34423A (es) 2013-07-31
MA34276B1 (fr) 2013-06-01
WO2013093220A1 (fr) 2013-06-27
US8513410B2 (en) 2013-08-20
SA112330994B1 (ar) 2015-08-03
PE20131097A1 (es) 2013-10-12
EA026510B1 (ru) 2017-04-28
JP2013129650A (ja) 2013-07-04
AU2012244188A1 (en) 2013-07-04
FR2984319A1 (fr) 2013-06-21
MD4336B1 (ro) 2015-03-31
TW201326132A (zh) 2013-07-01
SI2607353T1 (sl) 2014-12-31
US20130158256A1 (en) 2013-06-20
BR102012028614A2 (pt) 2014-12-16
PT2607353E (pt) 2014-10-10
AU2012244188B2 (en) 2015-07-30
GEP20156350B (en) 2015-08-25
MY170662A (en) 2019-08-26
KR20130071350A (ko) 2013-06-28
UA111329C2 (uk) 2016-04-25
FR2984319B1 (fr) 2013-12-27
EA201201385A1 (ru) 2013-06-28
CY1115682T1 (el) 2017-01-25
JO3031B1 (ar) 2016-09-05
AR088678A1 (es) 2014-06-25
PL2607353T3 (pl) 2015-01-30
EP2607353A1 (fr) 2013-06-26
HRP20141023T1 (hr) 2014-12-05
NZ603483A (en) 2014-02-28
HK1186733A1 (zh) 2014-03-21
CL2012003136A1 (es) 2014-08-01
KR101470879B1 (ko) 2014-12-09
EP2607353B1 (fr) 2014-08-27

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Legal Events

Date Code Title Description
FG4A Patent for invention issued
KA4A Patent for invention lapsed due to non-payment of fees (with right of restoration)
MM4A Patent for invention definitely lapsed due to non-payment of fees