HRP20100024T1 - Postupak priprave derivata 1,3,4,5-tetrahidro-2h-3-benzepin-2-ona, njihova primjena u sintezi ivabradina i njihove farmaceutski prihvatljive soli - Google Patents
Postupak priprave derivata 1,3,4,5-tetrahidro-2h-3-benzepin-2-ona, njihova primjena u sintezi ivabradina i njihove farmaceutski prihvatljive soli Download PDFInfo
- Publication number
- HRP20100024T1 HRP20100024T1 HR20100024T HRP20100024T HRP20100024T1 HR P20100024 T1 HRP20100024 T1 HR P20100024T1 HR 20100024 T HR20100024 T HR 20100024T HR P20100024 T HRP20100024 T HR P20100024T HR P20100024 T1 HRP20100024 T1 HR P20100024T1
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- compound
- synthesis
- process according
- synthesis process
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 11
- 230000015572 biosynthetic process Effects 0.000 title claims abstract 10
- 238000003786 synthesis reaction Methods 0.000 title claims abstract 10
- 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 claims 3
- 229960003825 ivabradine Drugs 0.000 title claims 3
- 150000003839 salts Chemical class 0.000 title claims 2
- GYIYVTGAOWHWRI-UHFFFAOYSA-N 1,2,3,5-tetrahydro-3-benzazepin-4-one Chemical class C1CNC(=O)CC2=CC=CC=C21 GYIYVTGAOWHWRI-UHFFFAOYSA-N 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 239000002904 solvent Substances 0.000 claims abstract 4
- CZLMRJZAHXYRIX-UHFFFAOYSA-N 1,3-dioxepane Chemical group C1CCOCOC1 CZLMRJZAHXYRIX-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000002378 acidificating effect Effects 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract 2
- 239000011541 reaction mixture Substances 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 238000005984 hydrogenation reaction Methods 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- VXPGKSAYOBZMSX-UHFFFAOYSA-N 1,3-dioxane;1,3-dioxolane Chemical compound C1COCO1.C1COCOC1 VXPGKSAYOBZMSX-UHFFFAOYSA-N 0.000 claims 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000001308 synthesis method Methods 0.000 claims 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (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)
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 |
|---|---|
| HRP20100024T1 true HRP20100024T1 (hr) | 2010-02-28 |
Family
ID=34941961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100024T HRP20100024T1 (hr) | 2004-04-13 | 2010-01-13 | Postupak priprave derivata 1,3,4,5-tetrahidro-2h-3-benzepin-2-ona, njihova primjena u sintezi ivabradina i njihove farmaceutski prihvatljive soli |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US7064200B2 (da) |
| EP (1) | EP1614687B1 (da) |
| JP (2) | JP4515933B2 (da) |
| KR (1) | KR100636499B1 (da) |
| CN (1) | CN100348585C (da) |
| AR (1) | AR047707A1 (da) |
| AT (1) | ATE448221T1 (da) |
| AU (1) | AU2005200884B2 (da) |
| BR (1) | BRPI0500590B8 (da) |
| CA (1) | CA2496712C (da) |
| CY (1) | CY1109740T1 (da) |
| DE (1) | DE602005017541D1 (da) |
| DK (1) | DK1614687T3 (da) |
| EA (1) | EA007743B1 (da) |
| EG (1) | EG25619A (da) |
| ES (1) | ES2336461T3 (da) |
| FR (1) | FR2868775B1 (da) |
| GE (1) | GEP20074136B (da) |
| HK (1) | HK1079777A1 (da) |
| HR (1) | HRP20100024T1 (da) |
| MA (1) | MA27598A1 (da) |
| MX (1) | MXPA05003696A (da) |
| MY (1) | MY140904A (da) |
| NO (1) | NO329861B1 (da) |
| NZ (1) | NZ538328A (da) |
| PL (1) | PL1614687T3 (da) |
| PT (1) | PT1614687E (da) |
| RS (1) | RS51232B (da) |
| SG (1) | SG116574A1 (da) |
| SI (1) | SI1614687T1 (da) |
| UA (1) | UA81773C2 (da) |
| WO (1) | WO2005111027A1 (da) |
| ZA (1) | ZA200501468B (da) |
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 | |
| WO2008146308A2 (en) | 2007-05-30 | 2008-12-04 | Ind-Swift Laboratories Limited | Process for the preparation of ivabradine hydrochloride and polymorph thereof |
| ES2402765T3 (es) | 2008-12-22 | 2013-05-08 | Krka, D.D., Novo Mesto | Procedimiento de preparación de ivabradina |
| 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. |
| SI23290A (sl) | 2010-02-12 | 2011-08-31 | Krka D.D., Novo Mesto | Nove oblike ivabradin hidroklorida |
| 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 |
| 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 |
| 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 active Active
- 2005-02-15 SG SG200500770A patent/SG116574A1/en unknown
- 2005-02-17 US US11/060,043 patent/US7064200B2/en active Active
- 2005-02-18 BR BRPI0500590A patent/BRPI0500590B8/pt active IP Right Grant
- 2005-02-18 AR ARP050100586A patent/AR047707A1/es active IP Right Grant
- 2005-02-18 GE GEAP8647A patent/GEP20074136B/en unknown
- 2005-02-18 MY MYPI20050621A patent/MY140904A/en unknown
- 2005-02-18 NO NO20050888A patent/NO329861B1/no unknown
- 2005-02-18 NZ NZ538328A patent/NZ538328A/en unknown
- 2005-02-18 ZA ZA2005/01468A patent/ZA200501468B/en unknown
- 2005-02-18 AU AU2005200884A patent/AU2005200884B2/en active Active
- 2005-02-18 CN CNB2005100542167A patent/CN100348585C/zh active Active
- 2005-02-18 UA UAA200501524A patent/UA81773C2/uk unknown
- 2005-02-18 JP JP2005041810A patent/JP4515933B2/ja active Active
- 2005-02-18 MA MA28112A patent/MA27598A1/fr unknown
- 2005-02-19 EG EG2005020086A patent/EG25619A/xx active
- 2005-02-19 KR KR1020050013860A patent/KR100636499B1/ko active IP Right Grant
- 2005-02-21 PL PL05290383T patent/PL1614687T3/pl unknown
- 2005-02-21 DK DK05290383.8T patent/DK1614687T3/da active
- 2005-02-21 RS RSP-2010/0006A patent/RS51232B/sr unknown
- 2005-02-21 AT AT05290383T patent/ATE448221T1/de active
- 2005-02-21 EA EA200500240A patent/EA007743B1/ru unknown
- 2005-02-21 PT PT05290383T patent/PT1614687E/pt unknown
- 2005-02-21 EP EP05290383A patent/EP1614687B1/fr active Active
- 2005-02-21 SI SI200530864T patent/SI1614687T1/sl unknown
- 2005-02-21 ES ES05290383T patent/ES2336461T3/es active Active
- 2005-02-21 DE DE602005017541T patent/DE602005017541D1/de active Active
- 2005-02-21 WO PCT/FR2005/000396 patent/WO2005111027A1/fr active Application Filing
- 2005-04-07 MX MXPA05003696A patent/MXPA05003696A/es active IP Right Grant
- 2005-12-22 HK HK05111843A patent/HK1079777A1/xx unknown
-
2009
- 2009-09-25 JP JP2009220529A patent/JP5277130B2/ja active Active
-
2010
- 2010-01-13 HR HR20100024T patent/HRP20100024T1/hr unknown
- 2010-01-19 CY CY20101100053T patent/CY1109740T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20100024T1 (hr) | Postupak priprave derivata 1,3,4,5-tetrahidro-2h-3-benzepin-2-ona, njihova primjena u sintezi ivabradina i njihove farmaceutski prihvatljive soli | |
| RS50511B (sr) | Postupak za sintezu ivabradina i njegovih farmaceutski prihvatljivih aditivnih soli kiselina | |
| Reddy et al. | Reductive amination of carbonyl compounds using NaBH4 in a Brønsted acidic ionic liquid | |
| O’Connor et al. | Direct Leuckart-type reductive amination of aldehydes and ketones: a facile one-pot protocol for the preparation of secondary and tertiary amines | |
| EP2683681A1 (de) | Verfahren zur herstellung von di-, tri- und polyaminen durch homogen-katalysierte alkoholaminierung | |
| Alexakis et al. | A practical, solvent free, one-pot synthesis of C2-symmetrical secondary amines | |
| CN103664677A (zh) | 一种(r,r)-福莫特罗酒石酸盐的不对称合成方法 | |
| WO2012119930A1 (de) | Verfahren zur herstellung von primären aminen durch homogen-katalysierte alkoholaminierung | |
| Neupane et al. | Efficient one-pot synthesis of cyclic β-enaminoamides by thermal Wolff rearrangement of cyclic 2-diazo-1, 3-dicarbonyls and conversion to uracil derivatives | |
| CA2409906A1 (en) | Process for producing optically active amino alcohols and intermediates therefor | |
| DE10212301A1 (de) | Verfahren zur Herstellung von Aryl-aminopropanolen | |
| CN105566138A (zh) | 一种合成西他列汀中间体的方法 | |
| CN101468954A (zh) | (r,r)-福莫特罗的不对称氢转移合成方法 | |
| RS50546B (sr) | Postupak sinteze derivata 1,3-dihidro-2h-3-benzazepin-2-on-a i primena u sintezi ivabradina i adicionih soli farmaceutski prihvatljive kiseliine | |
| CN104557583B (zh) | 一种合成γ-氨基丁酸类手性化合物的方法 | |
| CN102093346A (zh) | 一种吡喹酮的制备方法 | |
| DE60102008D1 (de) | Herstellungsverfahren für ein bekanntes terazolderivat | |
| CN100537582C (zh) | 一种双二茂铁膦二亚胺结构及其合成方法 | |
| CN102199098B (zh) | 一种合成(r)-n-苄基-1-(4-甲氧基苯基)-2-丙胺的方法及其应用 | |
| Zhu et al. | One-pot reductive amination of araldehydes by aniline using borohydride with CeCl3· 7H2O as catalyst | |
| EP3578545B1 (en) | Method for producing optically active pyrrolidine compounds | |
| CN103896795A (zh) | 甲酰胺化合物、其中间体的制备方法及其用途 | |
| Guérin et al. | Synthesis of Amines from Alcohols in a Nonepimerizing One‐Pot Sequence–Synthesis of Bioactive Compounds: Cinacalcet and Dexoxadrol | |
| Nakatani et al. | Enantioselective total synthesis of (2R, 3R, 6R)-N-methyl-6-(deca-1′, 3′, 5′-trienyl)-3-methoxy-2-methylpiperidine, an insecticidal alkaloid | |
| CN107235852B (zh) | 一种合成酰胺的方法 |