DD274215A5 - Verfahren zur herstellung von neuen benzimidazol-derivaten - Google Patents
Verfahren zur herstellung von neuen benzimidazol-derivaten Download PDFInfo
- Publication number
- DD274215A5 DD274215A5 DD88319141A DD31914188A DD274215A5 DD 274215 A5 DD274215 A5 DD 274215A5 DD 88319141 A DD88319141 A DD 88319141A DD 31914188 A DD31914188 A DD 31914188A DD 274215 A5 DD274215 A5 DD 274215A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- ethyl
- dihydro
- acid
- concentrated
- benzimidazole derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title claims abstract description 7
- 150000001556 benzimidazoles Chemical class 0.000 title description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052717 sulfur Chemical group 0.000 claims abstract description 5
- 239000011593 sulfur Chemical group 0.000 claims abstract description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 4
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 4
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 20
- -1 2- (N, N-dipropylamino) ethyl Chemical group 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
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- 238000001816 cooling Methods 0.000 description 9
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- 235000011152 sodium sulphate Nutrition 0.000 description 8
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- 239000000203 mixture Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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- 230000003291 dopaminomimetic effect Effects 0.000 description 5
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- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 description 2
- PLOMFWYHXDTNRJ-UHFFFAOYSA-N 3-[2-(dipropylamino)ethyl]benzene-1,2-diamine Chemical compound CCCN(CCC)CCC1=CC=CC(N)=C1N PLOMFWYHXDTNRJ-UHFFFAOYSA-N 0.000 description 2
- IFDIMWJXGASBLT-UHFFFAOYSA-N 3-[2-[butyl(methyl)amino]ethyl]benzene-1,2-diamine Chemical compound CCCCN(C)CCC1=CC=CC(N)=C1N IFDIMWJXGASBLT-UHFFFAOYSA-N 0.000 description 2
- XPCWMKVIKQPFSX-UHFFFAOYSA-N 4-[2-(dipropylamino)ethyl]-1,3-dihydrobenzimidazol-2-one Chemical compound CCCN(CCC)CCC1=CC=CC2=C1NC(=O)N2 XPCWMKVIKQPFSX-UHFFFAOYSA-N 0.000 description 2
- IPNDYABROJLNOR-UHFFFAOYSA-N 4-[2-[butyl(methyl)amino]ethyl]-1,3-dihydrobenzimidazole-2-thione Chemical compound CCCCN(C)CCC1=CC=CC2=C1NC(=S)N2 IPNDYABROJLNOR-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
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- 230000001800 adrenalinergic effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910000085 borane Inorganic materials 0.000 description 2
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 2
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- 125000004432 carbon atom Chemical group C* 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
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- 150000002390 heteroarenes Chemical class 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
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- ULOCHOLAPFZTGB-UHFFFAOYSA-N 1,3-benzothiazol-3-ium;bromide Chemical compound [Br-].C1=CC=C2SC=[NH+]C2=C1 ULOCHOLAPFZTGB-UHFFFAOYSA-N 0.000 description 1
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- HTOMICONFYSCTM-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]-n,n,n',n'-tetrapropylmethanediamine Chemical compound CCCN(CCC)C(OC(C)(C)C)N(CCC)CCC HTOMICONFYSCTM-UHFFFAOYSA-N 0.000 description 1
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- JUOHNWGCIDUACA-UHFFFAOYSA-N 2-(2,1,3-benzothiadiazol-4-yl)acetic acid Chemical compound OC(=O)CC1=CC=CC2=NSN=C12 JUOHNWGCIDUACA-UHFFFAOYSA-N 0.000 description 1
- CQOXALSPDITZGJ-UHFFFAOYSA-N 2-(2,3-dinitrophenyl)-n,n-dimethylethenamine Chemical compound CN(C)C=CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CQOXALSPDITZGJ-UHFFFAOYSA-N 0.000 description 1
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- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
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- VVCJBYVWJIAZOU-UHFFFAOYSA-N 3-[2-[propyl(2-thiophen-2-ylethyl)amino]ethyl]benzene-1,2-diamine Chemical compound C=1C=CC(N)=C(N)C=1CCN(CCC)CCC1=CC=CS1 VVCJBYVWJIAZOU-UHFFFAOYSA-N 0.000 description 1
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- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
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- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873728695 DE3728695A1 (de) | 1987-08-25 | 1987-08-25 | Neue benzimidazol-derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD274215A5 true DD274215A5 (de) | 1989-12-13 |
Family
ID=6334659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD88319141A DD274215A5 (de) | 1987-08-25 | 1988-08-23 | Verfahren zur herstellung von neuen benzimidazol-derivaten |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4925854A (pt) |
| EP (1) | EP0304789B1 (pt) |
| JP (1) | JP2818170B2 (pt) |
| AT (1) | ATE86982T1 (pt) |
| AU (1) | AU615939B2 (pt) |
| CA (1) | CA1330440C (pt) |
| DD (1) | DD274215A5 (pt) |
| DE (2) | DE3728695A1 (pt) |
| DK (1) | DK169701B1 (pt) |
| ES (1) | ES2054752T3 (pt) |
| FI (1) | FI99013C (pt) |
| HU (1) | HU201746B (pt) |
| IE (1) | IE63283B1 (pt) |
| IL (1) | IL87561A (pt) |
| NO (1) | NO170852C (pt) |
| PT (1) | PT88326B (pt) |
| ZA (1) | ZA886336B (pt) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE914003A1 (en) * | 1990-11-20 | 1992-05-20 | Astra Pharma Prod | Biologically Active Amines |
| US5371102A (en) * | 1992-03-11 | 1994-12-06 | University Of Hawaii | Compositions and methods of inhibiting thyroid activity |
| PE27997A1 (es) | 1994-04-29 | 1997-09-20 | Lilly Co Eli | Antagonistas de receptores de taquicininas |
| US5565454A (en) * | 1995-05-31 | 1996-10-15 | Ergo Science, Incorporated | Method for preventing intervention-associated stenosis and other symptoms associated with stenosis of blood vessels following non-bypass, invasive interventions |
| TW356468B (en) * | 1995-09-15 | 1999-04-21 | Astra Pharma Prod | Benzothiazolone compounds useful as beta2-adrenoreceptor and dopamine DA2 receptor agonists process for preparing same and pharmaceutical compositions containing same |
| GB9526511D0 (en) * | 1995-12-23 | 1996-02-28 | Astra Pharma Prod | Pharmaceutically active compounds |
| WO2004032861A2 (en) * | 2002-10-11 | 2004-04-22 | Bristol-Myers Squibb Company | Hexahydro-benzimidazolone compounds useful as anti-inflammatory agents |
| CN103987363B (zh) | 2011-12-16 | 2016-12-28 | 高露洁-棕榄公司 | 颜色变化的组合物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3813409A (en) * | 1972-07-31 | 1974-05-28 | Squibb & Sons Inc | Benzimidazolinone compounds |
| DE3042481A1 (de) * | 1980-11-11 | 1982-06-16 | A. Nattermann & Cie GmbH, 5000 Köln | (omega)-(2-oxo-benzazolinyl)-alkansaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| US4367337A (en) * | 1981-01-05 | 1983-01-04 | The Sherwin-Williams Company | Process for conversion of benzimidazolones to benzotriazoles |
| US4958026A (en) * | 1984-08-15 | 1990-09-18 | Schering Aktiengesllschaft | Novel dopamine derivatives, processes for their preparation, and their use as medicinal agents |
| US4554287A (en) * | 1984-09-12 | 1985-11-19 | Smithkline Beckman Corporation | Antihypertensive 7-[2-(dialkylamino)ethyl]-4-hydroxy-1,3-benzimidazol-2-ones |
-
1987
- 1987-08-25 DE DE19873728695 patent/DE3728695A1/de not_active Withdrawn
-
1988
- 1988-08-17 DE DE8888113339T patent/DE3879322D1/de not_active Expired - Lifetime
- 1988-08-17 EP EP88113339A patent/EP0304789B1/de not_active Expired - Lifetime
- 1988-08-17 AT AT88113339T patent/ATE86982T1/de active
- 1988-08-17 ES ES88113339T patent/ES2054752T3/es not_active Expired - Lifetime
- 1988-08-22 IE IE255288A patent/IE63283B1/en not_active IP Right Cessation
- 1988-08-23 DD DD88319141A patent/DD274215A5/de not_active IP Right Cessation
- 1988-08-23 JP JP63207486A patent/JP2818170B2/ja not_active Expired - Lifetime
- 1988-08-24 PT PT88326A patent/PT88326B/pt not_active IP Right Cessation
- 1988-08-24 NO NO883776A patent/NO170852C/no unknown
- 1988-08-24 CA CA000575617A patent/CA1330440C/en not_active Expired - Fee Related
- 1988-08-24 HU HU884447A patent/HU201746B/hu not_active IP Right Cessation
- 1988-08-25 DK DK474288A patent/DK169701B1/da not_active IP Right Cessation
- 1988-08-25 FI FI883930A patent/FI99013C/fi not_active IP Right Cessation
- 1988-08-25 ZA ZA886336A patent/ZA886336B/xx unknown
- 1988-08-25 AU AU21498/88A patent/AU615939B2/en not_active Ceased
- 1988-08-25 US US07/236,383 patent/US4925854A/en not_active Expired - Fee Related
- 1988-08-25 IL IL87561A patent/IL87561A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2054752T3 (es) | 1994-08-16 |
| DE3728695A1 (de) | 1989-03-09 |
| IL87561A0 (en) | 1989-01-31 |
| NO170852B (no) | 1992-09-07 |
| NO170852C (no) | 1992-12-16 |
| AU615939B2 (en) | 1991-10-17 |
| NO883776D0 (no) | 1988-08-24 |
| JP2818170B2 (ja) | 1998-10-30 |
| PT88326A (pt) | 1989-06-30 |
| NO883776L (no) | 1989-02-27 |
| EP0304789A3 (en) | 1989-10-04 |
| FI883930L (fi) | 1989-02-26 |
| JPS6468359A (en) | 1989-03-14 |
| DE3879322D1 (de) | 1993-04-22 |
| IE882552L (en) | 1989-02-25 |
| DK474288A (da) | 1989-02-26 |
| IE63283B1 (en) | 1995-04-05 |
| IL87561A (en) | 1993-02-21 |
| ZA886336B (en) | 1989-04-26 |
| ATE86982T1 (de) | 1993-04-15 |
| FI883930A0 (fi) | 1988-08-25 |
| CA1330440C (en) | 1994-06-28 |
| HU201746B (en) | 1990-12-28 |
| FI99013B (fi) | 1997-06-13 |
| DK474288D0 (da) | 1988-08-25 |
| EP0304789A2 (de) | 1989-03-01 |
| EP0304789B1 (de) | 1993-03-17 |
| US4925854A (en) | 1990-05-15 |
| PT88326B (pt) | 1995-03-31 |
| AU2149888A (en) | 1989-03-02 |
| DK169701B1 (da) | 1995-01-16 |
| FI99013C (fi) | 1997-09-25 |
| HUT49589A (en) | 1989-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| VZ | Disclaimer of patent (art. 11 and 12 extension act) |