CN103172566B - 合成伊伐布雷定以及其与可药用酸的加成盐的新方法 - Google Patents

合成伊伐布雷定以及其与可药用酸的加成盐的新方法 Download PDF

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Publication number
CN103172566B
CN103172566B CN201210443036.8A CN201210443036A CN103172566B CN 103172566 B CN103172566 B CN 103172566B CN 201210443036 A CN201210443036 A CN 201210443036A CN 103172566 B CN103172566 B CN 103172566B
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formula
reductive amination
amination reaction
ivabradine
compound
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Chinese (zh)
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CN103172566A (zh
Inventor
J-L·雷诺
N·潘尼提尔
J-P·勒库夫
L·韦斯-吕多
S·穆兰
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Laboratoires Servier SAS
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    • 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
    • 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
    • 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
    • B01J2235/00—Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties
    • B01J2235/05—Nuclear magnetic resonance [NMR]

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Cardiology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Urology & Nephrology (AREA)
  • Epidemiology (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Catalysts (AREA)
  • Saccharide Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CN201210443036.8A 2011-12-20 2012-11-08 合成伊伐布雷定以及其与可药用酸的加成盐的新方法 Expired - Fee Related CN103172566B (zh)

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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
FR11/03933 2011-12-20

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CN103172566A CN103172566A (zh) 2013-06-26
CN103172566B true CN103172566B (zh) 2015-11-18

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US (1) US8513410B2 (enExample)
EP (1) EP2607353B1 (enExample)
JP (1) JP5670406B2 (enExample)
KR (1) KR101470879B1 (enExample)
CN (1) CN103172566B (enExample)
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AU (1) AU2012244188B2 (enExample)
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GE (1) GEP20156350B (enExample)
HR (1) HRP20141023T1 (enExample)
JO (1) JO3031B1 (enExample)
MA (1) MA34276B1 (enExample)
MD (1) MD4336C1 (enExample)
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PE (1) PE20131097A1 (enExample)
PL (1) PL2607353T3 (enExample)
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SG (1) SG191471A1 (enExample)
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UY (1) UY34423A (enExample)
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ZA (1) ZA201208160B (enExample)

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 (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050228177A1 (en) * 2004-04-13 2005-10-13 Jean-Michel Lerestif Process for the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
CN101386594A (zh) * 2007-09-11 2009-03-18 瑟维尔实验室 1,2,4,5-四氢-3h-苯并氮杂䓬化合物、其制备方法与包含它们的药物组合物
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 (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2681862B1 (fr) * 1991-09-27 1993-11-12 Adir Cie Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent.
US6225487B1 (en) * 1998-04-17 2001-05-01 Symyx Technologies, Inc. Ancillary ligands and metal complexes, catalysts and compositions using same and methods of testing
US6521793B1 (en) * 1998-10-08 2003-02-18 Symyx Technologies, Inc. Catalyst ligands, catalytic metal complexes and processes using same
EP1595888A1 (en) * 2004-05-11 2005-11-16 Degussa AG Cycloolefin phosphine ligands and their use in catalysis
ES2381771T3 (es) * 2006-11-30 2012-05-31 Cadila Healthcare Limited Procedimiento para la preparación de hidrocloruro de ivabradina
US8212026B2 (en) * 2007-05-30 2012-07-03 Ind-Swift Laboratories Limited Process for the preparation of ivabradine hydrochloride and polymorph thereof
US7857994B2 (en) 2007-05-30 2010-12-28 GE Lighting Solutions, LLC Green emitting phosphors and blends thereof
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 (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050228177A1 (en) * 2004-04-13 2005-10-13 Jean-Michel Lerestif Process for the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
CN101386594A (zh) * 2007-09-11 2009-03-18 瑟维尔实验室 1,2,4,5-四氢-3h-苯并氮杂䓬化合物、其制备方法与包含它们的药物组合物
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 (5)

* Cited by examiner, † Cited by third party
Title
(Cyclopentadienone)iron Shvo Complexes: Synthesis and Applications to Hydrogen Transfer Reactions;Tarn C. Johnson等;《organometallics》;20110309;第30卷;第1859-1868页 *
An easy and general iron-catalyzed reductive amination of amination of aldehydes and ketones with anilines;Steffen Fleischer等;《Chemistry-An asian journal》;20110905;第6卷(第9期);第2240-2245页 *
Direct reductive amination of carbonyl compounds with primary/secondary amines using recyclable water-soluble FeII/EDTA complex as catalyst;Malhari D. Bhor等;《Tetrahedron Letters》;20071208;第49卷;第965-969页 *
Knolker’s Iron Complex: An Efficient In Situ Generated Catalyst for Reductive Amination of Alkyl Aldehydes and Amines;Anastassiya Pagnoux-ozherelyeva等;《Angew. Chem. Int. Ed.》;20120404;第51卷;第4976-4980页 *
Synthesis of Secondary Amines by Iron-Catalyzed Reductive Amination;Stephan Enthaler;《Chemcatchem》;20101115;第2卷(第11期);第1411-1415页 *

Also Published As

Publication number Publication date
CN103172566A (zh) 2013-06-26
MY170662A (en) 2019-08-26
ZA201208160B (en) 2013-06-26
EP2607353A1 (fr) 2013-06-26
AU2012244188A1 (en) 2013-07-04
SA112330994B1 (ar) 2015-08-03
AU2012244188B2 (en) 2015-07-30
UY34423A (es) 2013-07-31
MA34276B1 (fr) 2013-06-01
EP2607353B1 (fr) 2014-08-27
CA2795741A1 (fr) 2013-06-20
DK2607353T3 (en) 2014-12-08
CL2012003136A1 (es) 2014-08-01
JO3031B1 (ar) 2016-09-05
RS53541B1 (sr) 2015-02-27
TWI440627B (zh) 2014-06-11
SI2607353T1 (sl) 2014-12-31
CA2795741C (fr) 2015-09-08
HRP20141023T1 (hr) 2014-12-05
JP2013129650A (ja) 2013-07-04
EA026510B1 (ru) 2017-04-28
UA111329C2 (uk) 2016-04-25
KR101470879B1 (ko) 2014-12-09
HK1186733A1 (zh) 2014-03-21
MD4336B1 (ro) 2015-03-31
PT2607353E (pt) 2014-10-10
FR2984319B1 (fr) 2013-12-27
PL2607353T3 (pl) 2015-01-30
KR20130071350A (ko) 2013-06-28
BR102012028614A2 (pt) 2014-12-16
CY1115682T1 (el) 2017-01-25
MX2012012938A (es) 2013-06-19
WO2013093220A1 (fr) 2013-06-27
NZ603483A (en) 2014-02-28
US8513410B2 (en) 2013-08-20
PE20131097A1 (es) 2013-10-12
SG191471A1 (en) 2013-07-31
TW201326132A (zh) 2013-07-01
MD4336C1 (ro) 2015-10-31
FR2984319A1 (fr) 2013-06-21
JP5670406B2 (ja) 2015-02-18
EA201201385A1 (ru) 2013-06-28
AR088678A1 (es) 2014-06-25
ES2525032T3 (es) 2014-12-16
GEP20156350B (en) 2015-08-25
US20130158256A1 (en) 2013-06-20

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