AP369A - 1,5-Benzodiazepine derivatives. - Google Patents
1,5-Benzodiazepine derivatives. Download PDFInfo
- Publication number
- AP369A AP369A APAP/P/1993/000478A AP9300478A AP369A AP 369 A AP369 A AP 369A AP 9300478 A AP9300478 A AP 9300478A AP 369 A AP369 A AP 369A
- Authority
- AP
- ARIPO
- Prior art keywords
- solution
- phenyl
- give
- dioxo
- added
- Prior art date
Links
- ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical class N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 291
- -1 hydroxy, phenyl Chemical group 0.000 claims abstract description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000004202 carbamide Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 14
- AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
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- 108010052343 Gastrins Proteins 0.000 claims description 9
- 239000000460 chlorine Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 239000011737 fluorine Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
- 230000008901 benefit Effects 0.000 claims description 6
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- 239000003814 drug Substances 0.000 claims description 5
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 3
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- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
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- 238000003818 flash chromatography Methods 0.000 description 85
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
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- 229940049706 benzodiazepine Drugs 0.000 description 53
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- 238000005481 NMR spectroscopy Methods 0.000 description 33
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- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
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- DVARZUUKZACNGW-UHFFFAOYSA-N 2-(phenylhydrazinylidene)propanedioyl dichloride Chemical compound ClC(=O)C(C(Cl)=O)=NNC1=CC=CC=C1 DVARZUUKZACNGW-UHFFFAOYSA-N 0.000 description 16
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Classifications
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- 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
- C07D243/12—1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929201180A GB9201180D0 (en) | 1992-01-21 | 1992-01-21 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9300478A0 AP9300478A0 (en) | 1993-01-31 |
| AP369A true AP369A (en) | 1994-11-06 |
Family
ID=10708914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1993/000478A AP369A (en) | 1992-01-21 | 1993-01-20 | 1,5-Benzodiazepine derivatives. |
Country Status (29)
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9225492D0 (en) * | 1992-12-05 | 1993-01-27 | Glaxo Group Ltd | Amine derivatives |
| GB9307833D0 (en) * | 1993-04-15 | 1993-06-02 | Glaxo Inc | Modulators of cholecystokinin and gastrin |
| NZ265271A (en) * | 1993-04-15 | 1997-06-24 | Glaxo Wellcome Inc | 1-aminocarbonylmethyl-3-aminocarbonylamino-2,4-dioxo-1, 5-benzodiazepin derivatives pharmaceutical compositions thereof |
| GB9308421D0 (en) * | 1993-04-23 | 1993-06-09 | Glaxo Spa | Chemical compounds |
| GB9308431D0 (en) * | 1993-04-23 | 1993-06-09 | Glaxo Spa | Chemical compounds |
| GB9314977D0 (en) * | 1993-07-20 | 1993-09-01 | Glaxo Spa | Chemical compounds |
| GB2280182A (en) * | 1993-07-20 | 1995-01-25 | Glaxo Spa | Benzodiazepine derivatives |
| GB9314981D0 (en) * | 1993-07-20 | 1993-09-01 | Glaxo Spa | Chemical compounds |
| GB9315018D0 (en) * | 1993-07-20 | 1993-09-01 | Glaxo Spa | Chemical compounds |
| ATE181737T1 (de) * | 1994-04-14 | 1999-07-15 | Glaxo Wellcome Inc | Cck oder gastrin modulierende 5-heterocyclicyl- 1,5-benzodiazepine |
| US5739129A (en) * | 1994-04-14 | 1998-04-14 | Glaxo Wellcome Inc. | CCK or gastrin modulating 5-heterocyclic-1, 5 benzodiazepines |
| PE27497A1 (es) * | 1994-04-15 | 1997-08-07 | Glaxo Inc | Derivados de 1,5 benzodiazepina |
| GB9420748D0 (en) * | 1994-10-14 | 1994-11-30 | Glaxo Inc | 1,5 benzodiazepine derivatives |
| US5780464A (en) * | 1994-10-14 | 1998-07-14 | Glaxo Wellcome Inc. | Enteric coated compositions of 1,5-benzodiazepine derivatives having CCK antagonistic or agonistic activity |
| US5750353A (en) * | 1995-12-11 | 1998-05-12 | New England Medical Center Hospitals, Inc. | Assay for non-peptide agonists to peptide hormone receptors |
| CA2239293A1 (en) | 1995-12-11 | 1997-06-19 | New England Medical Center Hosptials, Inc. | Assay for and uses of peptide hormone receptor ligands |
| WO1998025911A1 (fr) * | 1996-12-10 | 1998-06-18 | Zeria Pharmaceutical Co., Ltd. | Derives de 1,5-benzodiazepine |
| RU2321583C2 (ru) * | 2001-01-22 | 2008-04-10 | Мемори Фармасьютиклз Корпорейшн | Применение производных анилина в качестве ингибиторов фосфодиэстеразы 4 |
| ATE552236T1 (de) * | 2003-01-14 | 2012-04-15 | Cytokinetics Inc | Verbindungen, zusammensetzungen und verfahren zur behandlung von herzinsuffizienz |
| GB0307918D0 (en) * | 2003-04-05 | 2003-05-14 | Astrazeneca Ab | Therapeutic use |
| CA2545513C (en) * | 2003-11-18 | 2013-01-08 | Boehringer Ingelheim International Gmbh | Solid pharmaceutical preparation form |
| US8110595B2 (en) | 2004-06-17 | 2012-02-07 | Cytokinetics, Inc. | Ureas and their use in the treatment of heart failure |
| US7538223B2 (en) | 2005-08-04 | 2009-05-26 | Cytokinetics, Inc. | Compounds, compositions and methods |
| ES2419007T3 (es) | 2005-12-15 | 2013-08-19 | Cytokinetics, Inc. | Ciertas entidades químicas, composiciones y procedimientos |
| US7825120B2 (en) | 2005-12-15 | 2010-11-02 | Cytokinetics, Inc. | Certain substituted ((piperazin-1-ylmethyl)benzyl)ureas |
| US7718657B2 (en) | 2005-12-16 | 2010-05-18 | Cytokinetics, Inc. | Certain indanyl urea modulators of the cardiac sarcomere |
| EP1962852B1 (en) | 2005-12-19 | 2017-01-25 | Cytokinetics, Inc. | Compounds, compositions and methods |
| CU20090172A7 (es) | 2009-10-09 | 2011-10-05 | Ct De Investigación Y Desarrollo De Medicamentos | Sistemas tricíclicos y tetracíclicos con actividad sobre el sistema nervioso central y vascular |
| ES2613808T3 (es) | 2011-07-29 | 2017-05-26 | Oncotherapy Science, Inc. | Péptido derivado de ERAP1 y uso del mismo |
| CN103435562B (zh) * | 2013-08-26 | 2016-02-24 | 华东理工大学 | 6-取代苯并二氮卓-2,4-二酮类化合物及其用途 |
| WO2017015449A1 (en) | 2015-07-22 | 2017-01-26 | Enanta Pharmaceuticals, Inc. | Benzodiazepine derivatives as rsv inhibitors |
| EP3402799B1 (en) | 2016-01-15 | 2022-05-04 | Enanta Pharmaceuticals, Inc. | Heterocyclic compounds as rsv inhibitors |
| KR102573499B1 (ko) | 2017-02-16 | 2023-08-31 | 이난타 파마슈티칼스, 인코포레이티드 | 벤조디아제핀 유도체의 제조 방법 |
| US10752598B2 (en) * | 2017-06-07 | 2020-08-25 | Enanta Pharmaceuticals, Inc. | Aryldiazepine derivatives as RSV inhibitors |
| US10851115B2 (en) | 2017-06-30 | 2020-12-01 | Enanta Pharmaceuticals, Inc. | Heterocyclic compounds as RSV inhibitors |
| US11091501B2 (en) | 2017-06-30 | 2021-08-17 | Enanta Pharmaceuticals, Inc. | Heterocyclic compounds as RSV inhibitors |
| AU2018339068B2 (en) | 2017-09-29 | 2022-12-15 | Enanta Pharmaceuticals, Inc. | Combination pharmaceutical agents as RSV inhibitors |
| US10647711B2 (en) | 2017-11-13 | 2020-05-12 | Enanta Pharmaceuticals, Inc. | Azepin-2-one derivatives as RSV inhibitors |
| US10975094B2 (en) | 2018-04-11 | 2021-04-13 | Enanta Pharmaceuticals, Inc. | Heterocyclic compounds as RSV inhibitors |
| US20220098256A1 (en) | 2018-11-30 | 2022-03-31 | Tokushima University | Therapeutic agent for breast cancer comprising big3-phb2 interaction-inhibiting peptide derived from phb2 |
| AU2020240024B2 (en) | 2019-03-18 | 2025-06-26 | Enanta Pharmaceuticals, Inc | Benzodiazepine derivatives as RSV inhibitors |
| US11179400B2 (en) | 2019-04-09 | 2021-11-23 | Enanta Pharmaceuticals, Inc. | Heterocyclic compounds as RSV inhibitors |
| US11505558B1 (en) | 2019-10-04 | 2022-11-22 | Enanta Pharmaceuticals, Inc. | Antiviral heterocyclic compounds |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0376849A1 (fr) * | 1988-12-29 | 1990-07-04 | Roussel-Uclaf | Nouveaux dérivés de la 2,4-dioxo 2,3,4,5-tétrahydro 1H-1,5-benzodiazépine, leur procédé et les intermédiaires de préparation, leur application comme médicaments et les compositions les renfermant |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3984398A (en) * | 1966-12-14 | 1976-10-05 | Roussel-Uclaf | 1,5-Benzodiazepine-2,4-diones |
| US4207228A (en) * | 1977-09-21 | 1980-06-10 | The B. F. Goodrich Company | UV-Light-stabilized compositions containing substituted 1,5-diazacycloalkanes, novel compounds and synthesis thereof |
| JPS60158190A (ja) * | 1984-01-30 | 1985-08-19 | Eisai Co Ltd | ヒダントイン誘導体およびその製法ならびにそれを含有する医薬 |
| US4647561A (en) * | 1985-08-05 | 1987-03-03 | E. R. Squibb & Sons, Inc. | 1,5-benzodiazepine compounds |
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1992
- 1992-01-21 GB GB929201180A patent/GB9201180D0/en active Pending
- 1992-01-21 GE GEAP19922651A patent/GEP20001968B/en unknown
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1993
- 1993-01-15 US US08/256,359 patent/US5580895A/en not_active Expired - Fee Related
- 1993-01-19 RO RO94-01216A patent/RO114128B1/ro unknown
- 1993-01-19 PL PL93304684A patent/PL175340B1/pl unknown
- 1993-01-19 HU HU9402150A patent/HU221297B1/hu not_active IP Right Cessation
- 1993-01-19 UA UA94005364A patent/UA29416C2/uk unknown
- 1993-01-19 WO PCT/EP1993/000098 patent/WO1993014074A1/en active IP Right Grant
- 1993-01-19 RU RU94037768A patent/RU2124009C1/ru active
- 1993-01-19 KR KR1019940702491A patent/KR100263625B1/ko not_active Expired - Fee Related
- 1993-01-19 AU AU34501/93A patent/AU3450193A/en not_active Abandoned
- 1993-01-19 SK SK864-94A patent/SK280173B6/sk unknown
- 1993-01-19 CZ CZ941736A patent/CZ283950B6/cs not_active IP Right Cessation
- 1993-01-20 MX MX9300261A patent/MX9300261A/es not_active IP Right Cessation
- 1993-01-20 CA CA002087672A patent/CA2087672C/en not_active Expired - Fee Related
- 1993-01-20 ZA ZA93375A patent/ZA93375B/xx unknown
- 1993-01-20 AU AU31935/93A patent/AU661749B2/en not_active Ceased
- 1993-01-20 JP JP02483193A patent/JP3253723B2/ja not_active Expired - Fee Related
- 1993-01-20 MY MYPI93000093A patent/MY131307A/en unknown
- 1993-01-20 NZ NZ245715A patent/NZ245715A/en unknown
- 1993-01-20 AP APAP/P/1993/000478A patent/AP369A/en active
- 1993-01-20 IS IS3970A patent/IS3970A/is unknown
- 1993-01-20 PH PH45583A patent/PH30894A/en unknown
- 1993-01-20 IL IL104447A patent/IL104447A/en not_active IP Right Cessation
- 1993-01-21 CN CN93101143A patent/CN1049217C/zh not_active Expired - Fee Related
- 1993-02-02 TW TW082100666A patent/TW226013B/zh active
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1994
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- 1994-07-18 OA OA60539A patent/OA09964A/en unknown
- 1994-07-19 FI FI943421A patent/FI111632B/fi active
- 1994-07-20 NO NO942720A patent/NO305952B1/no unknown
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1995
- 1995-06-16 HU HU95P/P00242P patent/HU211295A9/hu unknown
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1996
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0376849A1 (fr) * | 1988-12-29 | 1990-07-04 | Roussel-Uclaf | Nouveaux dérivés de la 2,4-dioxo 2,3,4,5-tétrahydro 1H-1,5-benzodiazépine, leur procédé et les intermédiaires de préparation, leur application comme médicaments et les compositions les renfermant |
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