IE821194L - Benzazepines and benzoidiazepines - Google Patents
Benzazepines and benzoidiazepinesInfo
- Publication number
- IE821194L IE821194L IE821194A IE119482A IE821194L IE 821194 L IE821194 L IE 821194L IE 821194 A IE821194 A IE 821194A IE 119482 A IE119482 A IE 119482A IE 821194 L IE821194 L IE 821194L
- Authority
- IE
- Ireland
- Prior art keywords
- group
- alkyl
- alkoxy
- represent
- hydroxy
- Prior art date
Links
- 150000008038 benzoazepines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002071 phenylalkoxy group Chemical group 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 230000001603 reducing effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Compounds of general formula I <IMAGE> (wherein A represents a <IMAGE> group, wherein R7 represents a C1-3 alkyl group, and B represents a methylene or carbonyl group or A represents a -CO-CO- group and B represents a methylene group; E represents an optionally substituted ethylene, n-propylene or n-butylene group; G represents an optionally substituted methylene or ethylene group; R1 and R2 represent a hydroxy, alkyl, alkoxy or phenyl-alkoxy group or one of them represents a hydrogen atom or together they represent an alkylenedioxy group; R3 and R4 represent hydrogen atoms, halogen atoms, trifluoromethyl, hydroxy, alkyl, alkoxy or cyano groups or one of them represents a nitro group or together they represent an alkylenedioxy group; R5 represents a hydrogen atom, an alkyl, hydroxy, alkoxy or optionally substituted amino group; and R6 represents a hydrogen atom, an alkyl, alkenyl, phenylalkyl or acyl group) and acid addition salts thereof show heart-rate reducing activity. <IMAGE>
[EP0065229A1]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813119874 DE3119874A1 (en) | 1981-05-19 | 1981-05-19 | "BENZAZEPINE DERIVATIVES, THEIR PRODUCTION AND THEIR USE AS MEDICINAL PRODUCTS" |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE821194L true IE821194L (en) | 1982-11-19 |
| IE53016B1 IE53016B1 (en) | 1988-05-11 |
Family
ID=6132690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1194/82A IE53016B1 (en) | 1981-05-19 | 1982-05-18 | Benzazepines and benzodiazepines |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP0065229B1 (en) |
| JP (1) | JPS57193462A (en) |
| KR (3) | KR890001544B1 (en) |
| AR (1) | AR231130A1 (en) |
| AT (1) | ATE14725T1 (en) |
| AU (1) | AU551509B2 (en) |
| BG (1) | BG60412B2 (en) |
| CA (1) | CA1185239A (en) |
| CS (2) | CS251760B2 (en) |
| DD (1) | DD202872A5 (en) |
| DE (2) | DE3119874A1 (en) |
| DK (1) | DK156720C (en) |
| ES (5) | ES8306726A1 (en) |
| FI (1) | FI77856C (en) |
| GB (1) | GB2099425B (en) |
| GR (1) | GR76458B (en) |
| HK (1) | HK43388A (en) |
| HU (1) | HU186584B (en) |
| IE (1) | IE53016B1 (en) |
| IL (1) | IL65814A (en) |
| MX (1) | MX9202743A (en) |
| NO (1) | NO159166C (en) |
| NZ (1) | NZ200659A (en) |
| PL (1) | PL136914B1 (en) |
| PT (1) | PT74919B (en) |
| SU (1) | SU1160935A3 (en) |
| UA (1) | UA8038A1 (en) |
| YU (1) | YU44674B (en) |
| ZA (1) | ZA823413B (en) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3242599A1 (en) * | 1982-11-18 | 1984-05-24 | Dr. Karl Thomae Gmbh, 7950 Biberach | NEW BENZAZEPINE DERIVATIVES, THEIR PRODUCTION AND THEIR USE AS MEDICINAL PRODUCTS |
| DE3343801A1 (en) * | 1983-12-03 | 1985-06-13 | Dr. Karl Thomae Gmbh, 7950 Biberach | NEW INDOLDER DERIVATIVES, MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF |
| DE3418271A1 (en) * | 1984-05-17 | 1985-11-21 | Dr. Karl Thomae Gmbh, 7950 Biberach | NEW BENZAZEPINE DERIVATIVES, MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF |
| DE3418270A1 (en) * | 1984-05-17 | 1985-11-21 | Dr. Karl Thomae Gmbh, 7950 Biberach | NEW AMINOTETRAL DERIVATIVES, MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF |
| EP0204349A3 (en) * | 1985-06-01 | 1990-01-03 | Dr. Karl Thomae GmbH | Heteroaromatic amine derivatives, medicaments containing them and process for their preparation |
| DE3717561A1 (en) * | 1987-05-25 | 1988-12-08 | Thomae Gmbh Dr K | INDOL, ISOCHINOLINE AND BENZAZEPINE DERIVATIVES, MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF |
| DE3541811A1 (en) * | 1985-11-27 | 1987-06-04 | Thomae Gmbh Dr K | NEW CYCLIC AMINE DERIVATIVES, MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF |
| DE3736866A1 (en) * | 1987-10-30 | 1989-05-11 | Thomae Gmbh Dr K | MEANS FOR THE TREATMENT OF HYPERTENSION AND HEART FAILURE |
| FR2624117B1 (en) * | 1987-12-08 | 1991-02-22 | Synthelabo | HYDROXY-3 (METHOXY-4 PHENYL) -2 (METHYLAMINO-2 ETHYL) -5 DIHYDRO-2,3 5H-BENZOTHIAZEPINE-1,5 ONE-4 DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
| JP2699511B2 (en) * | 1988-01-29 | 1998-01-19 | 武田薬品工業株式会社 | Substituted amines |
| JP2807577B2 (en) * | 1990-06-15 | 1998-10-08 | エーザイ株式会社 | Cyclic amide derivative |
| FR2681862B1 (en) * | 1991-09-27 | 1993-11-12 | Adir Cie | NOVELS (BENZOCYCLOALKYL) ALKYLAMINES, THEIR PREPARATION PROCESS, AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
| AU6971894A (en) * | 1993-05-27 | 1994-12-20 | Smithkline Beecham Laboratoires Pharmaceutiques | Anti-arrhythmic n-substituted 3-benzazepines or isoquinolines |
| FR2705675B1 (en) * | 1993-05-27 | 1996-05-03 | Smithkline Beecham Labo Pharma | New compounds, their preparation process and their use as medicaments. |
| SE9303274D0 (en) * | 1993-10-07 | 1993-10-07 | Astra Ab | Novel phenylethyl and phenylproplamines |
| DE10018401A1 (en) | 2000-04-13 | 2001-10-25 | Boehringer Ingelheim Pharma | Medicament for treating hypertrophy-related myocardial disease, containing bradycardic agent, preferably cilobradine, and optionally another cardiac drug |
| WO2002098865A2 (en) | 2001-06-07 | 2002-12-12 | Neuro3D | Cyclic nucleotide phosphodiesterase inhibitors, preparation and uses thereof |
| CN102976984B (en) * | 2003-08-29 | 2015-04-08 | 三井化学株式会社 | Preparation intermediate of insecticide for agricultural and horticultural uses |
| FR2868777B1 (en) * | 2004-04-13 | 2006-05-26 | Servier Lab | NOVEL PROCESS FOR THE SYNTHESIS OF IVABRADINE AND ITS SALTS OF ADDITION TO A PHARMACEUTICALLY ACCEPTABLE ACID |
| FR2868776B1 (en) * | 2004-04-13 | 2008-04-18 | Servier Lab | NOVEL PROCESS FOR THE SYNTHESIS OF 1,3-DIHYDRO-2H-3-BENZAZEPIN-2-ONE DERIVATIVES AND THE APPLICATION TO THE SYNTHESIS OF IVABRADINE AND ITS SALTS OF ADDITION TO A PHARMACEUTICALLY ACCEPTABLE ACID |
| FR2868775B1 (en) * | 2004-04-13 | 2008-04-11 | Servier Lab | NOVEL PROCESS FOR THE SYNTHESIS OF 1,3,4,5-TETRAHYDRO-2H-3-BENZAZEPIN-2-ONE DERIVATIVES AND THE APPLICATION TO THE SYNTHESIS OF IVABRADINE AND ITS SALTS OF ADDITION TO A PHARMACEUTICALLY ACCEPTABLE ACID |
| FR2870537A1 (en) * | 2004-05-19 | 2005-11-25 | Servier Lab | NOVEL PROCESS FOR SYNTHESIZING (1S) -4,5-DIMETHOXY-1- (METHYL AMINOMETHYL) BENZOCYCLOBUTANE AND ITS ADDITION SALTS AND APPLICATION TO THE SYNTHESIS OF IVABRADINE AND ITS ADDITION SALTS PHARMACEUTICALLY ACCEPTABLE ACID |
| FR2882553B1 (en) * | 2005-02-28 | 2007-05-04 | Servier Lab | CRYSTALLINE BETA FORM OF IVABRADINE HYDROCHLORIDE, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| FR2882555B1 (en) * | 2005-02-28 | 2007-05-04 | Servier Lab | CRYSTALLINE GAMMA FORM OF IVABRADINE HYDROCHLORIDE, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| FR2882554B1 (en) * | 2005-02-28 | 2007-05-04 | Servier Lab | IVABRADINE HYDROCHLORIDE BETA D-CRYSTALLINE FORM, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| FR2882556B1 (en) * | 2005-02-28 | 2007-05-04 | Servier Lab | CRYSTALLINE GAMMA D FORM OF IVABRADINE HYDROCHLORIDE, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| EP1762179A1 (en) | 2005-09-07 | 2007-03-14 | Boehringer Ingelheim Vetmedica Gmbh | Method for improving diagnostic quality in echocardiography |
| FR2891826B1 (en) * | 2005-10-11 | 2007-12-28 | Servier Lab | CRYSTALLINE FORM 6 OF IVABRADINE HYDROCHLORIDE, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| FR2891827B1 (en) * | 2005-10-11 | 2007-12-28 | Servier Lab | CRYSTALLINE DELTAD FORM OF IVABRADINE HYDROCHLORIDE, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| FR2920773B1 (en) * | 2007-09-11 | 2009-10-23 | Servier Lab | 1,2,4,5-TETRAHYDRO-3H-BENZAZEPINES DERIVATIVES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| FR2935381B1 (en) * | 2008-08-29 | 2010-12-17 | Servier Lab | NOVEL METHOD FOR THE RESOLUTION OF ENANTIOMERES OF (3,4-DIMETHOXY-BICYCLOO-4.2.0-OCTA-1,3,5-TRIEN-7-YL) NITRILE AND APPLICATION TO THE SYNTHESIS OF IVABRADINE |
| FR2941695B1 (en) * | 2009-02-04 | 2011-02-18 | Servier Lab | NOVEL PROCESS FOR THE SYNTHESIS OF IVABRADINE AND ITS SALTS OF ADDITION TO A PHARMACEUTICALLY ACCEPTABLE ACID |
| ME00986B (en) * | 2009-03-31 | 2012-06-20 | Servier Lab | New process for synthesiis of ivabradine and addition salts thereof with a pharmaceutically accept able acid |
| FR2943667B1 (en) * | 2009-03-31 | 2011-05-06 | Servier Lab | NEW PROCESS FOR THE SYNTHESIS OF IVABRADINE AND ITS SALTS OF ADDITION TO A PHARMACEUTICALLY ACCEPTABLE ACID |
| FR2956401B1 (en) * | 2010-02-17 | 2012-02-03 | Servier Lab | NOVEL PROCESS FOR THE SYNTHESIS OF IVABRADINE AND ITS SALTS OF ADDITION TO A PHARMACEUTICALLY ACCEPTABLE ACID |
| EP2741735A1 (en) | 2011-08-12 | 2014-06-18 | Boehringer Ingelheim Vetmedica GmbH | Funny current (if) inhibitors for use in a method of treating and preventing heart failure in feline |
| WO2014122248A1 (en) | 2013-02-11 | 2014-08-14 | Boehringer Ingelheim Vetmedica Gmbh | Kit-of-parts |
| FR3003859B1 (en) * | 2013-03-26 | 2015-03-13 | Servier Lab | "PROCESS FOR THE SYNTHESIS OF 7,8-DIMETHOXY-1,3-DIHYDRO-2H-3-BENZAZEPIN-2-ONE DERIVATIVES AND APPLICATION TO THE SYNTHESIS OF IVABRADINE" |
| HU230826B1 (en) * | 2014-11-19 | 2018-07-30 | Richter Gedeon Nyrt. | Process for preparation of benzazepine derivatives |
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 (en) | 1976-09-03 | 1987-03-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | 1-[6,7-Dimethoxy-3,4-dihydro-2H-isoquinolin-1-on-2-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane, its physiologically acceptable acid addition salts and medicaments containing these compounds |
| 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 (en) * | 1978-10-05 | 1980-05-16 | Hoechst Ag | A METHOD FOR PREPARING 4-PHENYL-1,3-BENZODIAZEPINES |
| DE2850078A1 (en) * | 1978-11-18 | 1980-05-29 | Basf Ag | AMINOPROPANOL DERIVATIVES OF 6-HYDROXY-2,3,4,5-TETRAHYDRO-1H-1-BENZAZEPIN-2-ONS |
-
1981
- 1981-05-19 DE DE19813119874 patent/DE3119874A1/en not_active Withdrawn
-
1982
- 1982-05-06 EP EP82103931A patent/EP0065229B1/en not_active Expired
- 1982-05-06 AT AT82103931T patent/ATE14725T1/en not_active IP Right Cessation
- 1982-05-06 DE DE8282103931T patent/DE3265206D1/en not_active Expired
- 1982-05-12 CS CS823456A patent/CS251760B2/en unknown
- 1982-05-13 UA UA3435639A patent/UA8038A1/en unknown
- 1982-05-13 SU SU823435639A patent/SU1160935A3/en active
- 1982-05-17 FI FI821724A patent/FI77856C/en not_active IP Right Cessation
- 1982-05-17 PL PL1982236474A patent/PL136914B1/en unknown
- 1982-05-17 DK DK222382A patent/DK156720C/en not_active IP Right Cessation
- 1982-05-17 DD DD82239912A patent/DD202872A5/en not_active IP Right Cessation
- 1982-05-18 IL IL65814A patent/IL65814A/en 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 JP JP57083915A patent/JPS57193462A/en active Granted
- 1982-05-18 ES ES512285A patent/ES8306726A1/en not_active Expired
- 1982-05-18 PT PT74919A patent/PT74919B/en unknown
- 1982-05-18 IE IE1194/82A patent/IE53016B1/en not_active IP Right Cessation
- 1982-05-18 YU YU1051/82A patent/YU44674B/en unknown
- 1982-05-18 NO NO821645A patent/NO159166C/en not_active IP Right Cessation
- 1982-05-18 ZA ZA823413A patent/ZA823413B/en unknown
- 1982-05-18 CA CA000403172A patent/CA1185239A/en not_active Expired
- 1982-05-18 HU HU821581A patent/HU186584B/en unknown
- 1982-05-18 AR AR289434A patent/AR231130A1/en active
- 1982-05-18 AU AU83794/82A patent/AU551509B2/en not_active Expired
- 1982-05-19 KR KR8202240A patent/KR890001544B1/en not_active Expired
- 1982-05-19 KR KR1019890001999A patent/KR890001545B1/en not_active Expired
- 1982-05-19 GR GR68197A patent/GR76458B/el unknown
- 1982-11-29 ES ES517753A patent/ES517753A0/en active Granted
- 1982-11-29 ES ES517756A patent/ES517756A0/en active Granted
- 1982-11-29 ES ES517758A patent/ES8308312A1/en not_active Expired
- 1982-11-29 ES ES517757A patent/ES517757A0/en active Granted
-
1988
- 1988-06-09 HK HK433/88A patent/HK43388A/en not_active IP Right Cessation
-
1989
- 1989-02-20 KR KR1019890001998A patent/KR890001550B1/en not_active Expired
-
1991
- 1991-12-27 CS CS914102A patent/CS410291A3/en unknown
-
1992
- 1992-06-09 MX MX9202743A patent/MX9202743A/en unknown
-
1994
- 1994-01-25 BG BG098418A patent/BG60412B2/en unknown
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| MK9A | Patent expired |