MD4461C1 - Procedeu de sinteză a compuşilor 7,8-dimetoxi-1,3-dihidro-2H-3-benzazepin-2-onei şi aplicarea în sinteza ivabradinei - Google Patents

Procedeu de sinteză a compuşilor 7,8-dimetoxi-1,3-dihidro-2H-3-benzazepin-2-onei şi aplicarea în sinteza ivabradinei

Info

Publication number
MD4461C1
MD4461C1 MDA20140028A MD20140028A MD4461C1 MD 4461 C1 MD4461 C1 MD 4461C1 MD A20140028 A MDA20140028 A MD A20140028A MD 20140028 A MD20140028 A MD 20140028A MD 4461 C1 MD4461 C1 MD 4461C1
Authority
MD
Moldova
Prior art keywords
synthesis
ivabradine
benzazepin
dimethoxy
dihydro
Prior art date
Application number
MDA20140028A
Other languages
English (en)
Russian (ru)
Other versions
MD4461B1 (ro
MD20140028A2 (ro
Inventor
Флоик Александр Ле
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
Application filed by Les Laboratoires Servier filed Critical Les Laboratoires Servier
Publication of MD20140028A2 publication Critical patent/MD20140028A2/ro
Publication of MD4461B1 publication Critical patent/MD4461B1/ro
Publication of MD4461C1 publication Critical patent/MD4461C1/ro

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/06—One of the condensed rings being a six-membered aromatic ring the other ring being four-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Invenţia se referă la un procedeu de sinteză a compusului cu formula (I):unde R reprezintă o grupă para-metoxibenzil (PMB) sau următoarea grupă:,conform căruia compusul cu formula (VII):unde R este definit mai sus, este supus unei reacţii de reducere, în prezenţa LiBH(Et)3, într-un solvent organic, pentru a obţine compusul cu formula (I).Se aplică în sinteza ivabradinei şi a sărurilor sale de adiţie cu un acid farmaceutic acceptabil.
MDA20140028A 2013-03-26 2014-03-20 Procedeu de sinteză a compuşilor 7,8-dimetoxi-1,3-dihidro-2H-3-benzazepin-2-onei şi aplicarea în sinteza ivabradinei MD4461C1 (ro)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1352741A FR3003859B1 (fr) 2013-03-26 2013-03-26 "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"

Publications (3)

Publication Number Publication Date
MD20140028A2 MD20140028A2 (ro) 2014-09-30
MD4461B1 MD4461B1 (ro) 2017-01-31
MD4461C1 true MD4461C1 (ro) 2017-08-31

Family

ID=48613923

Family Applications (1)

Application Number Title Priority Date Filing Date
MDA20140028A MD4461C1 (ro) 2013-03-26 2014-03-20 Procedeu de sinteză a compuşilor 7,8-dimetoxi-1,3-dihidro-2H-3-benzazepin-2-onei şi aplicarea în sinteza ivabradinei

Country Status (37)

Country Link
US (1) US8927708B2 (ro)
EP (1) EP2784066B1 (ro)
JP (1) JP5732159B2 (ro)
KR (1) KR101616434B1 (ro)
CN (1) CN104072420B (ro)
AR (1) AR095722A1 (ro)
AU (1) AU2014201355B2 (ro)
BR (1) BR102014007079A2 (ro)
CA (1) CA2846917C (ro)
CY (1) CY1116535T1 (ro)
DK (1) DK2784066T3 (ro)
EA (1) EA025516B1 (ro)
ES (1) ES2548713T3 (ro)
FR (1) FR3003859B1 (ro)
GE (1) GEP201706731B (ro)
HK (2) HK1198366A1 (ro)
HR (1) HRP20150924T1 (ro)
HU (1) HUE025550T2 (ro)
IN (1) IN2014DE00793A (ro)
JO (1) JO3132B1 (ro)
MA (1) MA35509B1 (ro)
MD (1) MD4461C1 (ro)
ME (1) ME02213B (ro)
MX (1) MX346640B (ro)
MY (1) MY189537A (ro)
NZ (1) NZ622915A (ro)
PL (1) PL2784066T3 (ro)
PT (1) PT2784066E (ro)
RS (1) RS54186B1 (ro)
SA (1) SA114350383B1 (ro)
SG (1) SG10201400610SA (ro)
SI (1) SI2784066T1 (ro)
TW (1) TWI511957B (ro)
UA (1) UA116527C2 (ro)
UY (1) UY35503A (ro)
WO (1) WO2014154994A1 (ro)
ZA (1) ZA201402072B (ro)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104610146A (zh) * 2015-01-23 2015-05-13 常州大学 一种3-氮杂二环[5,1,0]-7-醛及合成方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0534859B1 (fr) * 1991-09-27 1994-11-17 Adir Et Compagnie 3-Benzazépin-zones substituées par un groupe benzocyclobutyl- ou indanyl-alkyl-amino-alkyle, utiles dans le traitement des affections cardiovasculaires
WO2008065681A2 (en) * 2006-11-30 2008-06-05 Cadila Healthcare Limited Process for preparation of ivabradine hydrochloride
EP2135861A1 (fr) * 2008-06-20 2009-12-23 Les Laboratoires Servier Procédé de synthèse de la 7,8-diméthoxy-1,3-dihydro-2H-3-benzazépin-2-one, et son application à la synthèse de l'ivabradine et de ses sels d'addition avec un acide pharmaceutiquement acceptable

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3119874A1 (de) * 1981-05-19 1982-12-09 Dr. Karl Thomae Gmbh, 7950 Biberach "benzazepinderivate, ihre herstellung und ihre verwendung als arzneimittel"
US4490369A (en) * 1981-05-19 1984-12-25 Dr. Karl Thomae Gesellschaft Mit Beschrankter Haftung Benzazepine derivatives, their pharmaceutical compositions and method of use
DE3343801A1 (de) * 1983-12-03 1985-06-13 Dr. Karl Thomae Gmbh, 7950 Biberach Neue indolderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE3418270A1 (de) * 1984-05-17 1985-11-21 Dr. Karl Thomae Gmbh, 7950 Biberach Neue aminotetralinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE3519735A1 (de) * 1985-06-01 1986-12-04 Dr. Karl Thomae Gmbh, 7950 Biberach Neue heteroaromatische aminderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
EP0204349A3 (de) * 1985-06-01 1990-01-03 Dr. Karl Thomae GmbH Neue heteroaromatische Aminderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
FR2868775B1 (fr) * 2004-04-13 2008-04-11 Servier Lab Nouveau procede de synthese de derives de la 1,3,4,5- tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR2870537A1 (fr) * 2004-05-19 2005-11-25 Servier Lab 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
GB0412314D0 (en) * 2004-06-02 2004-07-07 Glaxo Group Ltd Compounds
US8312771B2 (en) 2006-11-10 2012-11-20 Siemens Medical Solutions Usa, Inc. Transducer array imaging system
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
CN101343249A (zh) * 2008-06-10 2009-01-14 上海医药工业研究院 3－(3－氯丙基)－7,8－二甲氧基－1,3－二氢－2h－3－苯并氮杂－2－酮的制备方法
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 (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0534859B1 (fr) * 1991-09-27 1994-11-17 Adir Et Compagnie 3-Benzazépin-zones substituées par un groupe benzocyclobutyl- ou indanyl-alkyl-amino-alkyle, utiles dans le traitement des affections cardiovasculaires
WO2008065681A2 (en) * 2006-11-30 2008-06-05 Cadila Healthcare Limited Process for preparation of ivabradine hydrochloride
EP2135861A1 (fr) * 2008-06-20 2009-12-23 Les Laboratoires Servier Procédé de synthèse de la 7,8-diméthoxy-1,3-dihydro-2H-3-benzazépin-2-one, et son application à la synthèse de l'ivabradine et de ses sels d'addition avec un acide pharmaceutiquement acceptable

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Reiffen M., Eberlein W., Mueller P., Psiorz M., Noll K., Heider J., Lillie C., Kobinger W., Luger P. Specific bradycardic agents. Chemistry, pharmacology, and structure-activity relationships of substituted benzazepinones, a new class of compounds exerting antiischemic properties. Journal of Medicinal Chemistry, 1990, vol. 33, nr. 5, p. 1496-1504 *

Also Published As

Publication number Publication date
TWI511957B (zh) 2015-12-11
EP2784066B1 (fr) 2015-07-01
SI2784066T1 (sl) 2015-10-30
AR095722A1 (es) 2015-11-04
GEP201706731B (en) 2017-09-11
MD4461B1 (ro) 2017-01-31
EP2784066A1 (fr) 2014-10-01
EA025516B1 (ru) 2016-12-30
FR3003859A1 (fr) 2014-10-03
ZA201402072B (en) 2015-03-25
WO2014154994A1 (fr) 2014-10-02
SA114350383B1 (ar) 2015-10-08
RS54186B1 (en) 2015-12-31
CN104072420B (zh) 2016-09-28
MA35509B1 (fr) 2014-10-02
MD20140028A2 (ro) 2014-09-30
MY189537A (en) 2022-02-16
CN104072420A (zh) 2014-10-01
AU2014201355B2 (en) 2017-08-24
ME02213B (me) 2016-02-20
HRP20150924T1 (hr) 2015-10-09
UY35503A (es) 2014-10-31
ES2548713T3 (es) 2015-10-20
FR3003859B1 (fr) 2015-03-13
KR20140117298A (ko) 2014-10-07
PT2784066E (pt) 2015-08-31
JO3132B1 (ar) 2017-09-20
DK2784066T3 (en) 2015-10-05
US8927708B2 (en) 2015-01-06
NZ622915A (en) 2015-05-29
HUE025550T2 (en) 2016-02-29
SG10201400610SA (en) 2014-10-30
AU2014201355A1 (en) 2014-10-16
BR102014007079A2 (pt) 2015-10-20
KR101616434B1 (ko) 2016-04-28
MX346640B (es) 2017-03-27
HK1202532A1 (en) 2015-10-02
EA201400269A1 (ru) 2014-09-30
MX2014003347A (es) 2014-09-25
IN2014DE00793A (ro) 2015-06-12
CY1116535T1 (el) 2017-03-15
CA2846917C (fr) 2016-02-09
PL2784066T3 (pl) 2015-11-30
US20140296512A1 (en) 2014-10-02
HK1198366A1 (en) 2015-04-10
UA116527C2 (uk) 2018-04-10
JP5732159B2 (ja) 2015-06-10
JP2014196299A (ja) 2014-10-16
CA2846917A1 (fr) 2014-09-26
TW201522313A (zh) 2015-06-16

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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