HRP20060449T3 - Process for the preparation of (1s)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane, acid additon salts thereof and its use for the synthesis of ivabradine and for its pharmaceutically acceptable acid addition salts - Google Patents
Process for the preparation of (1s)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane, acid additon salts thereof and its use for the synthesis of ivabradine and for its pharmaceutically acceptable acid addition saltsInfo
- Publication number
- HRP20060449T3 HRP20060449T3 HR20060449T HRP20060449T HRP20060449T3 HR P20060449 T3 HRP20060449 T3 HR P20060449T3 HR 20060449 T HR20060449 T HR 20060449T HR P20060449 T HRP20060449 T HR P20060449T HR P20060449 T3 HRP20060449 T3 HR P20060449T3
- Authority
- HR
- Croatia
- Prior art keywords
- salts
- ivabradine
- benzocyclobutane
- methylaminomethyl
- dimethoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title 2
- 150000003839 salts Chemical class 0.000 title 2
- SAVVFXUMMFHSJC-SECBINFHSA-N 1-[(7s)-3,4-dimethoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl]-n-methylmethanamine Chemical compound COC1=C(OC)C=C2[C@@H](CNC)CC2=C1 SAVVFXUMMFHSJC-SECBINFHSA-N 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- ACRHBAYQBXXRTO-OAQYLSRUSA-N ivabradine Chemical compound C1CC2=CC(OC)=C(OC)C=C2CC(=O)N1CCCN(C)C[C@H]1CC2=C1C=C(OC)C(OC)=C2 ACRHBAYQBXXRTO-OAQYLSRUSA-N 0.000 title 1
- 229960003825 ivabradine Drugs 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000004220 glutamic acid Substances 0.000 abstract 1
- 238000000967 suction filtration Methods 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- 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
- A61P9/06—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
- A61P9/10—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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0405453A FR2870537A1 (fr) | 2004-05-19 | 2004-05-19 | 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20060449T3 true HRP20060449T3 (en) | 2007-03-31 |
Family
ID=34941962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20060449T HRP20060449T3 (en) | 2004-05-19 | 2006-12-19 | Process for the preparation of (1s)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane, acid additon salts thereof and its use for the synthesis of ivabradine and for its pharmaceutically acceptable acid addition salts |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US6982350B2 (me) |
| EP (1) | EP1598333B1 (me) |
| JP (1) | JP4148952B2 (me) |
| KR (1) | KR100649289B1 (me) |
| CN (1) | CN1332933C (me) |
| AR (1) | AR047746A1 (me) |
| AT (1) | ATE342885T1 (me) |
| AU (1) | AU2005200883B2 (me) |
| BR (1) | BRPI0500480B8 (me) |
| CA (1) | CA2496708C (me) |
| CY (1) | CY1105826T1 (me) |
| DE (1) | DE602005000187T2 (me) |
| DK (1) | DK1598333T3 (me) |
| EA (1) | EA007746B1 (me) |
| EG (1) | EG23719A (me) |
| ES (1) | ES2275258T3 (me) |
| FR (1) | FR2870537A1 (me) |
| GE (1) | GEP20074135B (me) |
| HK (1) | HK1081945A1 (me) |
| HR (1) | HRP20060449T3 (me) |
| MA (1) | MA27640A1 (me) |
| ME (1) | ME01395B (me) |
| MX (1) | MXPA05005139A (me) |
| MY (1) | MY139475A (me) |
| NO (1) | NO330968B1 (me) |
| NZ (1) | NZ538329A (me) |
| PL (1) | PL1598333T3 (me) |
| PT (1) | PT1598333E (me) |
| RS (1) | RS50512B (me) |
| SI (1) | SI1598333T1 (me) |
| UA (1) | UA79482C2 (me) |
| WO (1) | WO2005123659A1 (me) |
| ZA (1) | ZA200501469B (me) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2097383B1 (en) * | 2006-11-30 | 2012-02-08 | Cadila Healthcare Limited | Process for preparation of ivabradine hydrochloride |
| PT2471780E (pt) | 2007-05-30 | 2015-02-24 | Ind Swift Lab Ltd | Sais oxalato de ivabradina cristalinos e seus polimorfos |
| CN101434552B (zh) * | 2007-11-16 | 2012-05-23 | 江苏恒瑞医药股份有限公司 | 4,5-二甲氧基-1-(甲基氨基甲基)-苯并环丁烷的拆分 |
| FR2927900B1 (fr) * | 2008-02-27 | 2010-09-17 | Clariant Specialty Fine Chem | Procede de preparation d'alpha-aminoacetals optiquement actifs. |
| 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 |
| CN101671265B (zh) * | 2008-09-12 | 2012-08-15 | 中国科学院上海药物研究所 | 一种苯并环丁烷类化合物及其制备方法与用途 |
| CN102264689B (zh) * | 2008-12-22 | 2014-12-31 | 新梅斯托克尔卡公司 | 制备伊伐布雷定的方法 |
| FR2940287B1 (fr) * | 2008-12-24 | 2010-12-24 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable. |
| FR2943667B1 (fr) * | 2009-03-31 | 2011-05-06 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable. |
| ME00986B (me) | 2009-03-31 | 2012-06-20 | Servier Lab | Novi postupak sinteze ivabradina i njegovih adicionih soli sa farmaceutski prihvatljivom kiselinom |
| EP2534135A2 (en) | 2010-02-12 | 2012-12-19 | KRKA, D.D., Novo Mesto | Novel forms of ivabradine hydrochloride |
| HUP1000245A2 (en) | 2010-05-07 | 2011-11-28 | Richter Gedeon Nyrt | Industrial process for the production ivabradin salts |
| CN102249937A (zh) * | 2010-05-18 | 2011-11-23 | 上海京新生物医药有限公司 | 1-(s)-4,5-二甲氧基-1-甲胺基甲基-苯并环丁烷的制备方法 |
| CN102372642B (zh) * | 2011-07-04 | 2014-01-08 | 江苏宇田生物医药科技有限公司 | (1s)-4,5-二甲氧基-1-[(甲基氨基)甲基]苯并环丁烷的制备方法 |
| ITMI20111467A1 (it) * | 2011-08-01 | 2013-02-02 | Laboratorio Chimico Int Spa | Procedimento per la preparazione di ivabradina e di suoi intermedi di sintesi |
| CN102408346B (zh) * | 2011-10-31 | 2014-07-02 | 江苏阿尔法药业有限公司 | 一种4,5-二甲氧基-1-（甲基氨基甲基）-苯并环丁烷的制备方法 |
| FR2984320B1 (fr) * | 2011-12-20 | 2013-11-29 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| FR2986804A1 (fr) * | 2012-02-09 | 2013-08-16 | Servier Lab | Procede de synthese enzymatique de l'acide (7s) 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene 7-carboxylique ou de ses esters, et application a la synthese de l'ivabradine et de ses sels |
| 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 |
| FR2993561B1 (fr) | 2012-07-17 | 2014-10-31 | Servier Lab | Procede de synthese enzymatique de la (7s)-1-(3,4-dimethoxy bicyclo[4.2.0]octa-1,3,5-triene 7-yl) n-methyl methanamine, et application a la synthese de l'ivabradine et de ses sels |
| CN103848789B (zh) * | 2012-11-29 | 2016-05-18 | 江苏恒瑞医药股份有限公司 | 一种伊伐布雷定的制备方法 |
| FR3003859B1 (fr) * | 2013-03-26 | 2015-03-13 | Servier Lab | "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" |
| FR3005658B1 (fr) * | 2013-05-17 | 2015-04-24 | Servier Lab | "procede de synthese du 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable" |
| WO2015022702A2 (en) * | 2013-08-10 | 2015-02-19 | Ind-Swift Laboratories Limited | Process for preparation of 4,5-dimethoxybenzene derivatives and use in the synthesis of ivabradine and salts thereof |
| CN103524360B (zh) * | 2013-10-17 | 2015-09-30 | 安徽安腾药业有限责任公司 | 一种伊伐布雷定关键中间体的合成方法 |
| WO2015119057A1 (ja) * | 2014-02-06 | 2015-08-13 | 宇部興産株式会社 | インドリン化合物の製造方法 |
| EP3101010A1 (en) | 2015-06-03 | 2016-12-07 | Urquima S.A. | New method for the preparation of highly pure ivabradine base and salts thereof |
| CN110483312A (zh) * | 2019-08-27 | 2019-11-22 | 北京阳光诺和药物研究有限公司 | 一种高纯度盐酸伊伐布雷定及其中间体的制备方法 |
| CN115286577B (zh) * | 2022-08-25 | 2023-10-20 | 江苏永安制药有限公司 | 一种盐酸伊伐布雷定及其中间体的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE52768B1 (en) * | 1981-04-06 | 1988-02-17 | Boots Co Ltd | 1-arylcyclobutylalkylamine compounds useful as therapeutic agents |
| DE3119874A1 (de) * | 1981-05-19 | 1982-12-09 | Dr. Karl Thomae Gmbh, 7950 Biberach | "benzazepinderivate, ihre herstellung und ihre verwendung als arzneimittel" |
| EP0072061B1 (en) * | 1981-08-05 | 1985-05-15 | FISONS plc | Amine derivatives, processes for their production and pharmaceutical compositions containing them |
| JP2823679B2 (ja) * | 1990-05-08 | 1998-11-11 | 東レ株式会社 | 光学活性２―メチルピペラジンの製造方法 |
| FR2681862B1 (fr) * | 1991-09-27 | 1993-11-12 | Adir Cie | Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent. |
| JPH083120A (ja) | 1994-06-21 | 1996-01-09 | Ajinomoto Co Inc | アシル−アミノ酸とα−アリールアミンとの付加塩及びα−アリールアミンの光学分割法 |
| JPH09208546A (ja) * | 1995-11-29 | 1997-08-12 | Ajinomoto Co Inc | 新規置換ベンジルアミンの付加塩及びその光学分割法 |
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2004
- 2004-05-19 FR FR0405453A patent/FR2870537A1/fr active Pending
-
2005
- 2005-02-07 CA CA2496708A patent/CA2496708C/fr active Active
- 2005-02-17 BR BRPI0500480A patent/BRPI0500480B8/pt active IP Right Grant
- 2005-02-17 US US11/060,011 patent/US6982350B2/en active Active
- 2005-02-18 ZA ZA2005/01469A patent/ZA200501469B/en unknown
- 2005-02-18 NZ NZ538329A patent/NZ538329A/en unknown
- 2005-02-18 MA MA28115A patent/MA27640A1/fr unknown
- 2005-02-18 MY MYPI20050618A patent/MY139475A/en unknown
- 2005-02-18 CN CNB2005100517682A patent/CN1332933C/zh active Active
- 2005-02-18 UA UAA200501519A patent/UA79482C2/uk unknown
- 2005-02-18 AR ARP050100589A patent/AR047746A1/es not_active Application Discontinuation
- 2005-02-18 NO NO20050883A patent/NO330968B1/no unknown
- 2005-02-18 JP JP2005041813A patent/JP4148952B2/ja active Active
- 2005-02-18 GE GEAP8646A patent/GEP20074135B/en unknown
- 2005-02-18 AU AU2005200883A patent/AU2005200883B2/en active Active
- 2005-02-19 EG EG2005020088A patent/EG23719A/xx active
- 2005-02-19 KR KR1020050013861A patent/KR100649289B1/ko active IP Right Grant
- 2005-02-21 EA EA200500239A patent/EA007746B1/ru unknown
- 2005-02-21 EP EP05290384A patent/EP1598333B1/fr active Active
- 2005-02-21 RS YUP-2006/0654A patent/RS50512B/sr unknown
- 2005-02-21 DE DE602005000187T patent/DE602005000187T2/de active Active
- 2005-02-21 SI SI200530004T patent/SI1598333T1/sl unknown
- 2005-02-21 DK DK05290384T patent/DK1598333T3/da active
- 2005-02-21 PL PL05290384T patent/PL1598333T3/pl unknown
- 2005-02-21 AT AT05290384T patent/ATE342885T1/de active
- 2005-02-21 WO PCT/FR2005/000397 patent/WO2005123659A1/fr active Application Filing
- 2005-02-21 ES ES05290384T patent/ES2275258T3/es active Active
- 2005-02-21 PT PT05290384T patent/PT1598333E/pt unknown
- 2005-02-21 ME MEP-2006-654A patent/ME01395B/me unknown
- 2005-05-13 MX MXPA05005139A patent/MXPA05005139A/es active IP Right Grant
-
2006
- 2006-02-22 HK HK06102329A patent/HK1081945A1/xx unknown
- 2006-12-05 CY CY20061101742T patent/CY1105826T1/el unknown
- 2006-12-19 HR HR20060449T patent/HRP20060449T3/xx unknown
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