AR047707A1 - Un procedimiento de sintesis de compuestos de la 1,3,4,5-tetrahidro-2h-3-benzazepin-2-ona, y su aplicacion a la sintesis de la ivabradina y sus sales de adicion con un acido farmaceuticamente aceptable - Google Patents
Un procedimiento de sintesis de compuestos de la 1,3,4,5-tetrahidro-2h-3-benzazepin-2-ona, y su aplicacion a la sintesis de la ivabradina y sus sales de adicion con un acido farmaceuticamente aceptableInfo
- Publication number
- AR047707A1 AR047707A1 ARP050100586A ARP050100586A AR047707A1 AR 047707 A1 AR047707 A1 AR 047707A1 AR P050100586 A ARP050100586 A AR P050100586A AR P050100586 A ARP050100586 A AR P050100586A AR 047707 A1 AR047707 A1 AR 047707A1
- Authority
- AR
- Argentina
- Prior art keywords
- synthesis
- formula
- ivabradine
- compounds
- procedure
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 8
- 230000015572 biosynthetic process Effects 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 4
- 238000003786 synthesis reaction Methods 0.000 title abstract 4
- 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 abstract 3
- 229960003825 ivabradine Drugs 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical group C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 abstract 2
- CZLMRJZAHXYRIX-UHFFFAOYSA-N 1,3-dioxepane Chemical compound C1CCOCOC1 CZLMRJZAHXYRIX-UHFFFAOYSA-N 0.000 abstract 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
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
-
- 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
- A61P9/04—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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Compuestos de formula (2), donde R1 y R2, idénticos o diferentes, representan cada uno un grupo alcoxi C1-8 lineal o ramificado, o forman conjuntamente con el átomo de carbono que los lleva un anillo 1,3-dioxano, 1,3-dioxolano o 1,3- dioxepano. Reivindicacion 1: Procedimiento de síntesis de compuestos formula (1), donde R1 y R2, idénticos o diferentes, representan cada uno un grupo alcoxi C1-8 lineal o ramificado, o bien forman conjuntamente con el átomo de carbono que los lleva un anillo 1,3-dioxano, 1,3-dioxolano o 1,3-dioxepano, caracterizado porque se somete el compuesto de formula (2), donde R1 y R2 son tales como se definiera precedentemente, a una reaccion de hidrogenacion catalítica, en un solvente no acídico, luego se filtra la mezcla de reaccion, para obtener el compuesto de formula (1). Reivindicacion 11: Procedimiento de síntesis de la ivabradina y de sus sales farmacéuticamente aceptables e hidratos, caracterizado porque el compuesto de formula (2) se convierte en el compuesto intermediario de formula (1) de acuerdo con el procedimiento de la reivindicacion 1, y luego el compuesto intermediario de formula (1) se convierte en ivabradina.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0403828A FR2868775B1 (fr) | 2004-04-13 | 2004-04-13 | 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR047707A1 true AR047707A1 (es) | 2006-02-08 |
Family
ID=34941961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP050100586A AR047707A1 (es) | 2004-04-13 | 2005-02-18 | Un procedimiento de sintesis de compuestos de la 1,3,4,5-tetrahidro-2h-3-benzazepin-2-ona, y su aplicacion a la sintesis de la ivabradina y sus sales de adicion con un acido farmaceuticamente aceptable |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US7064200B2 (es) |
| EP (1) | EP1614687B1 (es) |
| JP (2) | JP4515933B2 (es) |
| KR (1) | KR100636499B1 (es) |
| CN (1) | CN100348585C (es) |
| AR (1) | AR047707A1 (es) |
| AT (1) | ATE448221T1 (es) |
| AU (1) | AU2005200884B2 (es) |
| BR (1) | BRPI0500590B8 (es) |
| CA (1) | CA2496712C (es) |
| CY (1) | CY1109740T1 (es) |
| DE (1) | DE602005017541D1 (es) |
| DK (1) | DK1614687T3 (es) |
| EA (1) | EA007743B1 (es) |
| EG (1) | EG25619A (es) |
| ES (1) | ES2336461T3 (es) |
| FR (1) | FR2868775B1 (es) |
| GE (1) | GEP20074136B (es) |
| HR (1) | HRP20100024T1 (es) |
| MA (1) | MA27598A1 (es) |
| MX (1) | MXPA05003696A (es) |
| MY (1) | MY140904A (es) |
| NO (1) | NO329861B1 (es) |
| NZ (1) | NZ538328A (es) |
| PL (1) | PL1614687T3 (es) |
| PT (1) | PT1614687E (es) |
| RS (1) | RS51232B (es) |
| SG (1) | SG116574A1 (es) |
| SI (1) | SI1614687T1 (es) |
| UA (1) | UA81773C2 (es) |
| WO (1) | WO2005111027A1 (es) |
| ZA (1) | ZA200501468B (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2868777B1 (fr) * | 2004-04-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| 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 |
| GT200500185A (es) * | 2004-08-09 | 2006-04-10 | Moduladores del receptor de progesterona que comprenden derivados de pirrol-oxindol y sus usos | |
| RU2473544C2 (ru) | 2007-05-30 | 2013-01-27 | Инд-Свифт Лабораториз Лимитед | Способ получения ивабрадина гидрохлорида и его полиморфных модификаций |
| 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. |
| SI2902384T1 (en) | 2010-02-12 | 2018-03-30 | Krka, D.D., Novo Mesto | The form of ivabradine hydrochloride |
| FR2956401B1 (fr) * | 2010-02-17 | 2012-02-03 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| FR2971507B1 (fr) * | 2011-02-14 | 2013-01-18 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| 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 |
| 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 |
| 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" |
Family Cites Families (7)
| 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" |
| 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 |
| EP0204349A3 (de) * | 1985-06-01 | 1990-01-03 | Dr. Karl Thomae GmbH | Neue heteroaromatische Aminderivate, 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 |
| FR2681862B1 (fr) * | 1991-09-27 | 1993-11-12 | Adir Cie | Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent. |
| FR2868777B1 (fr) * | 2004-04-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| 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 |
-
2004
- 2004-04-13 FR FR0403828A patent/FR2868775B1/fr not_active Expired - Fee Related
-
2005
- 2005-02-07 CA CA2496712A patent/CA2496712C/fr not_active Expired - Lifetime
- 2005-02-15 SG SG200500770A patent/SG116574A1/en unknown
- 2005-02-17 US US11/060,043 patent/US7064200B2/en not_active Expired - Lifetime
- 2005-02-18 MY MYPI20050621A patent/MY140904A/en unknown
- 2005-02-18 NO NO20050888A patent/NO329861B1/no unknown
- 2005-02-18 ZA ZA2005/01468A patent/ZA200501468B/en unknown
- 2005-02-18 AR ARP050100586A patent/AR047707A1/es active IP Right Grant
- 2005-02-18 JP JP2005041810A patent/JP4515933B2/ja not_active Expired - Lifetime
- 2005-02-18 NZ NZ538328A patent/NZ538328A/en not_active IP Right Cessation
- 2005-02-18 MA MA28112A patent/MA27598A1/fr unknown
- 2005-02-18 UA UAA200501524A patent/UA81773C2/uk unknown
- 2005-02-18 BR BRPI0500590A patent/BRPI0500590B8/pt not_active IP Right Cessation
- 2005-02-18 CN CNB2005100542167A patent/CN100348585C/zh not_active Expired - Lifetime
- 2005-02-18 AU AU2005200884A patent/AU2005200884B2/en not_active Expired
- 2005-02-18 GE GEAP8647A patent/GEP20074136B/en unknown
- 2005-02-19 EG EG2005020086A patent/EG25619A/xx active
- 2005-02-19 KR KR1020050013860A patent/KR100636499B1/ko not_active Expired - Lifetime
- 2005-02-21 SI SI200530864T patent/SI1614687T1/sl unknown
- 2005-02-21 ES ES05290383T patent/ES2336461T3/es not_active Expired - Lifetime
- 2005-02-21 WO PCT/FR2005/000396 patent/WO2005111027A1/fr not_active Ceased
- 2005-02-21 AT AT05290383T patent/ATE448221T1/de active
- 2005-02-21 RS RSP-2010/0006A patent/RS51232B/sr unknown
- 2005-02-21 DE DE602005017541T patent/DE602005017541D1/de not_active Expired - Lifetime
- 2005-02-21 DK DK05290383.8T patent/DK1614687T3/da active
- 2005-02-21 EP EP05290383A patent/EP1614687B1/fr not_active Expired - Lifetime
- 2005-02-21 PT PT05290383T patent/PT1614687E/pt unknown
- 2005-02-21 EA EA200500240A patent/EA007743B1/ru unknown
- 2005-02-21 PL PL05290383T patent/PL1614687T3/pl unknown
- 2005-04-07 MX MXPA05003696A patent/MXPA05003696A/es active IP Right Grant
-
2009
- 2009-09-25 JP JP2009220529A patent/JP5277130B2/ja not_active Expired - Lifetime
-
2010
- 2010-01-13 HR HR20100024T patent/HRP20100024T1/hr unknown
- 2010-01-19 CY CY20101100053T patent/CY1109740T1/el unknown
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| FG | Grant, registration |