SU1160935A3 - Способ получени производных бензазепина или их кислотно-аддитивных солей с неорганическими кислотами - Google Patents
Способ получени производных бензазепина или их кислотно-аддитивных солей с неорганическими кислотами Download PDFInfo
- Publication number
- SU1160935A3 SU1160935A3 SU823435639A SU3435639A SU1160935A3 SU 1160935 A3 SU1160935 A3 SU 1160935A3 SU 823435639 A SU823435639 A SU 823435639A SU 3435639 A SU3435639 A SU 3435639A SU 1160935 A3 SU1160935 A3 SU 1160935A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- benzazepin
- dimethoxy
- amino
- group
- methyl
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 9
- 150000007522 mineralic acids Chemical class 0.000 title claims description 3
- 239000000654 additive Substances 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 4
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- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000002071 phenylalkoxy group Chemical group 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 3
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- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000006250 trifluoro ethyl amino group Chemical group [H]N(*)C([H])([H])C(F)(F)F 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
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- 230000000996 additive effect Effects 0.000 claims 1
- 150000008038 benzoazepines Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
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- 125000003342 alkenyl group Chemical group 0.000 abstract 1
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- 230000001603 reducing effect Effects 0.000 abstract 1
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- 238000002329 infrared spectrum Methods 0.000 description 23
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OCWIGVMXGDBYIY-UHFFFAOYSA-N n-ethyl-n-methyl-1,3-benzodioxol-5-amine Chemical compound CCN(C)C1=CC=C2OCOC2=C1 OCWIGVMXGDBYIY-UHFFFAOYSA-N 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
-
- 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
- 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
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- 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
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/02—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/04—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813119874 DE3119874A1 (de) | 1981-05-19 | 1981-05-19 | "benzazepinderivate, ihre herstellung und ihre verwendung als arzneimittel" |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1160935A3 true SU1160935A3 (ru) | 1985-06-07 |
Family
ID=6132690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU823435639A SU1160935A3 (ru) | 1981-05-19 | 1982-05-13 | Способ получени производных бензазепина или их кислотно-аддитивных солей с неорганическими кислотами |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP0065229B1 (enExample) |
| JP (1) | JPS57193462A (enExample) |
| KR (3) | KR890001545B1 (enExample) |
| AR (1) | AR231130A1 (enExample) |
| AT (1) | ATE14725T1 (enExample) |
| AU (1) | AU551509B2 (enExample) |
| BG (1) | BG60412B2 (enExample) |
| CA (1) | CA1185239A (enExample) |
| CS (2) | CS251760B2 (enExample) |
| DD (1) | DD202872A5 (enExample) |
| DE (2) | DE3119874A1 (enExample) |
| DK (1) | DK156720C (enExample) |
| ES (5) | ES512285A0 (enExample) |
| FI (1) | FI77856C (enExample) |
| GB (1) | GB2099425B (enExample) |
| GR (1) | GR76458B (enExample) |
| HK (1) | HK43388A (enExample) |
| HU (1) | HU186584B (enExample) |
| IE (1) | IE53016B1 (enExample) |
| IL (1) | IL65814A (enExample) |
| MX (1) | MX9202743A (enExample) |
| NO (1) | NO159166C (enExample) |
| NZ (1) | NZ200659A (enExample) |
| PL (1) | PL136914B1 (enExample) |
| PT (1) | PT74919B (enExample) |
| SU (1) | SU1160935A3 (enExample) |
| UA (1) | UA8038A1 (enExample) |
| YU (1) | YU44674B (enExample) |
| ZA (1) | ZA823413B (enExample) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA007743B1 (ru) * | 2004-04-13 | 2006-12-29 | Ле Лаборатуар Сервье | Способ получения производных 1,3,4,5-тетрагидро-2н-3-бензазепин-2-она |
| EA007746B1 (ru) * | 2004-05-19 | 2006-12-29 | Ле Лаборатуар Сервье | Способ синтеза (1s)-4,5-диметокси-1-(метиламинометил)бензоциклобутана |
| EA007744B1 (ru) * | 2004-04-13 | 2006-12-29 | Ле Лаборатуар Сервье | Способ получения производных 1,3-дигидро-2н-3-бензазепин-2-она |
| EA007745B1 (ru) * | 2004-04-13 | 2006-12-29 | Ле Лаборатуар Сервье | Способ получения ивабрадина |
| EA008465B1 (ru) * | 2005-02-28 | 2007-06-29 | Ле Лаборатуар Сервье | γ-КРИСТАЛЛИЧЕСКАЯ ФОРМА ГИДРОХЛОРИДА ИВАБРАДИНА, СПОСОБ ЕЁ ПОЛУЧЕНИЯ И ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ, КОТОРЫЕ ЕЁ СОДЕРЖАТ |
| EA008464B1 (ru) * | 2005-02-28 | 2007-06-29 | Ле Лаборатуар Сервье | β-КРИСТАЛЛИЧЕСКАЯ ФОРМА ГИДРОХЛОРИДА ИВАБРАДИНА, СПОСОБ ЕЁ ПОЛУЧЕНИЯ И ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ, КОТОРЫЕ ЕЁ СОДЕРЖАТ |
| EA008532B1 (ru) * | 2005-02-28 | 2007-06-29 | Ле Лаборатуар Сервье | γd-КРИСТАЛЛИЧЕСКАЯ ФОРМА ГИДРОХЛОРИДА ИВАБРАДИНА, СПОСОБ ЕЕ ПОЛУЧЕНИЯ И ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ, КОТОРЫЕ ЕЕ СОДЕРЖАТ |
| EA008466B1 (ru) * | 2005-02-28 | 2007-06-29 | Ле Лаборатуар Сервье | βd-КРИСТАЛЛИЧЕСКАЯ ФОРМА ГИДРОХЛОРИДА ИВАБРАДИНА, СПОСОБ ЕЁ ПОЛУЧЕНИЯ И ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ, КОТОРЫЕ ЕЁ СОДЕРЖАТ |
| EA010296B1 (ru) * | 2005-10-11 | 2008-08-29 | Ле Лаборатуар Сервье | δ-КРИСТАЛЛИЧЕСКАЯ ФОРМА ГИДРОХЛОРИДА ИВАБРАДИНА, СПОСОБ ЕЁ ПОЛУЧЕНИЯ И ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ, КОТОРЫЕ ЕЁ СОДЕРЖАТ |
| EA010286B1 (ru) * | 2005-10-11 | 2008-08-29 | Ле Лаборатуар Сервье | δd-КРИСТАЛЛИЧЕСКАЯ ФОРМА ГИДРОХЛОРИДА ИВАБРАДИНА, СПОСОБ ЕЁ ПОЛУЧЕНИЯ И ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ, КОТОРЫЕ ЕЁ СОДЕРЖАТ |
| EA014756B1 (ru) * | 2007-09-11 | 2011-02-28 | Ле Лаборатуар Сервье | Соединения 1,2,4,5-тетрагидро-3h-бензазепина, способ их получения и фармацевтические композиции, содержащие эти соединения |
| EA015777B1 (ru) * | 2008-08-29 | 2011-12-30 | Ле Лаборатуар Сервье | Способ разделения энантиомеров (3,4-диметоксибицикло[4.2.0]окта-1,3,5-триен-7-ил)нитрила и применение при синтезе ивабрадина |
| EA016353B1 (ru) * | 2009-03-31 | 2012-04-30 | Ле Лаборатуар Сервье | Новый способ синтеза ивабрадина и его солей присоединения с фармацевтически приемлемой кислотой |
| EA016335B1 (ru) * | 2009-03-31 | 2012-04-30 | Ле Лаборатуар Сервье | Новый способ синтеза ивабрадина и его солей присоединения с фармацевтически приемлемой кислотой |
| EA019373B1 (ru) * | 2010-02-17 | 2014-03-31 | Ле Лаборатуар Сервье | Новый способ синтеза ивабрадина и его аддитивных солей с фармацевтически приемлемой кислотой |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3242599A1 (de) * | 1982-11-18 | 1984-05-24 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue benzazepinderivate, ihre herstellung und ihre verwendung als arzneimittel |
| 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 |
| DE3418271A1 (de) * | 1984-05-17 | 1985-11-21 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue benzazepinderivate, 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 |
| DE3541811A1 (de) * | 1985-11-27 | 1987-06-04 | Thomae Gmbh Dr K | Neue cyclische aminderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE3717561A1 (de) * | 1987-05-25 | 1988-12-08 | Thomae Gmbh Dr K | Indol-, isochinolin- und benzazepinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE3736866A1 (de) * | 1987-10-30 | 1989-05-11 | Thomae Gmbh Dr K | Mittel zur behandlung des bluthochdrucks und der herzinsuffizienz |
| FR2624117B1 (fr) * | 1987-12-08 | 1991-02-22 | Synthelabo | Derives de hydroxy-3 (methoxy-4 phenyl)-2 (methylamino-2 ethyl)-5 dihydro-2,3 5h-benzothiazepine-1,5 one-4, leur preparation et leur application en therapeutique |
| JP2699511B2 (ja) * | 1988-01-29 | 1998-01-19 | 武田薬品工業株式会社 | 置換アミン類 |
| JP2807577B2 (ja) * | 1990-06-15 | 1998-10-08 | エーザイ株式会社 | 環状アミド誘導体 |
| FR2681862B1 (fr) * | 1991-09-27 | 1993-11-12 | Adir Cie | Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent. |
| FR2705675B1 (fr) * | 1993-05-27 | 1996-05-03 | Smithkline Beecham Labo Pharma | Nouveaux composés, leur procédé de préparation et leur utilisation en tant que médicaments. |
| WO1994027971A1 (en) * | 1993-05-27 | 1994-12-08 | Smithkline Beecham Laboratoires Pharmaceutiques | Anti-arrhythmic n-substituted 3-benzazepines or isoquinolines |
| SE9303274D0 (sv) * | 1993-10-07 | 1993-10-07 | Astra Ab | Novel phenylethyl and phenylproplamines |
| DE10018401A1 (de) | 2000-04-13 | 2001-10-25 | Boehringer Ingelheim Pharma | Verwendung von Bradycardica bei der Behandlung von mit Hypertrophie einhergehenden Myocarderkrankungen und neue Arzneimittelkombinationen |
| US7250410B2 (en) | 2001-06-07 | 2007-07-31 | Via Pharmaceuticals, Inc. | Cyclic nucleotide phosphodiesterase inhibitors, preparation and uses thereof |
| CA2772017C (en) * | 2003-08-29 | 2016-05-31 | Mitsui Chemicals, Inc. | Agricultural/horticultural insecticide and method for using the same |
| EP1762179A1 (en) | 2005-09-07 | 2007-03-14 | Boehringer Ingelheim Vetmedica Gmbh | Method for improving diagnostic quality in echocardiography |
| 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 |
| MX2014001557A (es) | 2011-08-12 | 2014-03-31 | Boehringer Ingelheim Vetmed | Inhibidores de corrientes funny (if) para utilizar en un metodo de tratamiento y prevencion de la insuficiencia cardiaca en felinos. |
| EP2953612A1 (en) | 2013-02-11 | 2015-12-16 | Boehringer Ingelheim Vetmedica GmbH | Kit-of-parts |
| 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" |
| HU230826B1 (hu) * | 2014-11-19 | 2018-07-30 | Richter Gedeon Nyrt. | Eljárás benzazepin származékok előállítására |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3474090A (en) * | 1966-12-22 | 1969-10-21 | American Cyanamid Co | 3-aminoalkyl-1,3-benzodiazepin-2-ones |
| US3780023A (en) * | 1972-06-30 | 1973-12-18 | J Suh | 2-aralkylamino-4,5-dihydro-3h-1,3-benzodiazepines |
| US4210749A (en) * | 1974-11-12 | 1980-07-01 | Pennwalt Corporation | Substituted 1,2,4,5-tetrahydro-3H,3 benzazepines |
| DE2639718C2 (de) | 1976-09-03 | 1987-03-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | 1-[6,7-Dimethoxy-3,4-dihydro-2H-isochinolin-1-on-2-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-äthyl)-amino]-propan, dessen physiologisch verträgliche Säureadditionssalze und diese Verbindungen enthaltende Arzneimittel |
| ZA786230B (en) * | 1977-12-21 | 1979-10-31 | Smithkline Corp | 8 and/or 9 substituted 2-benzazepine compounds |
| ZA792785B (en) | 1978-07-07 | 1980-08-27 | Smithkline Corp | Mercapto substituted-2,3,4,5-tetrahydro-1h-3-benzazepines |
| ES484553A1 (es) * | 1978-10-05 | 1980-05-16 | Hoechst Ag | Un metodo para preparar 4-fenil-1,3-benzodiazepinas |
| DE2850078A1 (de) * | 1978-11-18 | 1980-05-29 | Basf Ag | Aminopropanolderivate des 6-hydroxy-2,3,4,5-tetrahydro-1h-1- benzazepin-2-ons |
-
1981
- 1981-05-19 DE DE19813119874 patent/DE3119874A1/de not_active Withdrawn
-
1982
- 1982-05-06 DE DE8282103931T patent/DE3265206D1/de not_active Expired
- 1982-05-06 EP EP82103931A patent/EP0065229B1/de not_active Expired
- 1982-05-06 AT AT82103931T patent/ATE14725T1/de not_active IP Right Cessation
- 1982-05-12 CS CS823456A patent/CS251760B2/cs unknown
- 1982-05-13 UA UA3435639A patent/UA8038A1/uk unknown
- 1982-05-13 SU SU823435639A patent/SU1160935A3/ru active
- 1982-05-17 FI FI821724A patent/FI77856C/fi not_active IP Right Cessation
- 1982-05-17 DD DD82239912A patent/DD202872A5/de not_active IP Right Cessation
- 1982-05-17 DK DK222382A patent/DK156720C/da not_active IP Right Cessation
- 1982-05-17 PL PL1982236474A patent/PL136914B1/pl unknown
- 1982-05-18 CA CA000403172A patent/CA1185239A/en not_active Expired
- 1982-05-18 AR AR289434A patent/AR231130A1/es active
- 1982-05-18 IL IL65814A patent/IL65814A/xx not_active IP Right Cessation
- 1982-05-18 GB GB8214503A patent/GB2099425B/en not_active Expired
- 1982-05-18 NZ NZ200659A patent/NZ200659A/en unknown
- 1982-05-18 AU AU83794/82A patent/AU551509B2/en not_active Expired
- 1982-05-18 PT PT74919A patent/PT74919B/pt unknown
- 1982-05-18 JP JP57083915A patent/JPS57193462A/ja active Granted
- 1982-05-18 YU YU1051/82A patent/YU44674B/xx unknown
- 1982-05-18 HU HU821581A patent/HU186584B/hu unknown
- 1982-05-18 IE IE1194/82A patent/IE53016B1/en not_active IP Right Cessation
- 1982-05-18 NO NO821645A patent/NO159166C/no not_active IP Right Cessation
- 1982-05-18 ES ES512285A patent/ES512285A0/es active Granted
- 1982-05-18 ZA ZA823413A patent/ZA823413B/xx unknown
- 1982-05-19 KR KR1019890001999A patent/KR890001545B1/ko not_active Expired
- 1982-05-19 GR GR68197A patent/GR76458B/el unknown
- 1982-05-19 KR KR8202240A patent/KR890001544B1/ko not_active Expired
- 1982-11-29 ES ES517756A patent/ES517756A0/es active Granted
- 1982-11-29 ES ES517757A patent/ES517757A0/es active Granted
- 1982-11-29 ES ES517753A patent/ES517753A0/es active Granted
- 1982-11-29 ES ES517758A patent/ES8308312A1/es not_active Expired
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1988
- 1988-06-09 HK HK433/88A patent/HK43388A/xx not_active IP Right Cessation
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1989
- 1989-02-20 KR KR1019890001998A patent/KR890001550B1/ko not_active Expired
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1991
- 1991-12-27 CS CS914102A patent/CS410291A3/cs unknown
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1992
- 1992-06-09 MX MX9202743A patent/MX9202743A/es unknown
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1994
- 1994-01-25 BG BG098418A patent/BG60412B2/bg unknown
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| Патент СССР № 659081, кл. С 07 С 93/06, 1979. * |
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| EA007744B1 (ru) * | 2004-04-13 | 2006-12-29 | Ле Лаборатуар Сервье | Способ получения производных 1,3-дигидро-2н-3-бензазепин-2-она |
| EA007745B1 (ru) * | 2004-04-13 | 2006-12-29 | Ле Лаборатуар Сервье | Способ получения ивабрадина |
| US7176197B2 (en) | 2004-04-13 | 2007-02-13 | Les Laboratoires Servier | Process for the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid |
| US7867994B2 (en) | 2004-04-13 | 2011-01-11 | Les Laboratoires Servier | Process for the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid |
| EA007746B1 (ru) * | 2004-05-19 | 2006-12-29 | Ле Лаборатуар Сервье | Способ синтеза (1s)-4,5-диметокси-1-(метиламинометил)бензоциклобутана |
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| EA008532B1 (ru) * | 2005-02-28 | 2007-06-29 | Ле Лаборатуар Сервье | γd-КРИСТАЛЛИЧЕСКАЯ ФОРМА ГИДРОХЛОРИДА ИВАБРАДИНА, СПОСОБ ЕЕ ПОЛУЧЕНИЯ И ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ, КОТОРЫЕ ЕЕ СОДЕРЖАТ |
| EA008464B1 (ru) * | 2005-02-28 | 2007-06-29 | Ле Лаборатуар Сервье | β-КРИСТАЛЛИЧЕСКАЯ ФОРМА ГИДРОХЛОРИДА ИВАБРАДИНА, СПОСОБ ЕЁ ПОЛУЧЕНИЯ И ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ, КОТОРЫЕ ЕЁ СОДЕРЖАТ |
| EA008465B1 (ru) * | 2005-02-28 | 2007-06-29 | Ле Лаборатуар Сервье | γ-КРИСТАЛЛИЧЕСКАЯ ФОРМА ГИДРОХЛОРИДА ИВАБРАДИНА, СПОСОБ ЕЁ ПОЛУЧЕНИЯ И ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ, КОТОРЫЕ ЕЁ СОДЕРЖАТ |
| EA010296B1 (ru) * | 2005-10-11 | 2008-08-29 | Ле Лаборатуар Сервье | δ-КРИСТАЛЛИЧЕСКАЯ ФОРМА ГИДРОХЛОРИДА ИВАБРАДИНА, СПОСОБ ЕЁ ПОЛУЧЕНИЯ И ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ, КОТОРЫЕ ЕЁ СОДЕРЖАТ |
| EA010286B1 (ru) * | 2005-10-11 | 2008-08-29 | Ле Лаборатуар Сервье | δd-КРИСТАЛЛИЧЕСКАЯ ФОРМА ГИДРОХЛОРИДА ИВАБРАДИНА, СПОСОБ ЕЁ ПОЛУЧЕНИЯ И ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ, КОТОРЫЕ ЕЁ СОДЕРЖАТ |
| EA014756B1 (ru) * | 2007-09-11 | 2011-02-28 | Ле Лаборатуар Сервье | Соединения 1,2,4,5-тетрагидро-3h-бензазепина, способ их получения и фармацевтические композиции, содержащие эти соединения |
| EA015777B1 (ru) * | 2008-08-29 | 2011-12-30 | Ле Лаборатуар Сервье | Способ разделения энантиомеров (3,4-диметоксибицикло[4.2.0]окта-1,3,5-триен-7-ил)нитрила и применение при синтезе ивабрадина |
| EA016353B1 (ru) * | 2009-03-31 | 2012-04-30 | Ле Лаборатуар Сервье | Новый способ синтеза ивабрадина и его солей присоединения с фармацевтически приемлемой кислотой |
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