SK280907B6 - Deriváty tetrahydrokarbazolu, spôsob ich prípravy a farmaceutický prípravok s ich obsahom - Google Patents
Deriváty tetrahydrokarbazolu, spôsob ich prípravy a farmaceutický prípravok s ich obsahom Download PDFInfo
- Publication number
- SK280907B6 SK280907B6 SK1685-98A SK168598A SK280907B6 SK 280907 B6 SK280907 B6 SK 280907B6 SK 168598 A SK168598 A SK 168598A SK 280907 B6 SK280907 B6 SK 280907B6
- Authority
- SK
- Slovakia
- Prior art keywords
- tetrahydrocarbazole
- formula
- amino
- compound
- solution
- Prior art date
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- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- -1 -CO 2 R 4 Chemical group 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000556 agonist Substances 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 239000005557 antagonist Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 84
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 22
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
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- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- PMQBOSGFSARWCB-MRVPVSSYSA-N (6R)-6-amino-6,7,8,9-tetrahydro-5H-carbazole-3-carboxamide Chemical compound N1C2=CC=C(C(N)=O)C=C2C2=C1CC[C@@H](N)C2 PMQBOSGFSARWCB-MRVPVSSYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- DDLAOJUFZYVVOR-UHFFFAOYSA-N 6-amino-6,7,8,9-tetrahydro-5h-carbazole-3-carbonitrile Chemical compound N1C2=CC=C(C#N)C=C2C2=C1CCC(N)C2 DDLAOJUFZYVVOR-UHFFFAOYSA-N 0.000 claims description 2
- 238000005576 amination reaction Methods 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 1
- IWBWMPCHOBTEEO-UHFFFAOYSA-N 6-nitro-2,3,4,9-tetrahydro-1h-carbazol-3-amine Chemical compound N1C2=CC=C([N+]([O-])=O)C=C2C2=C1CCC(N)C2 IWBWMPCHOBTEEO-UHFFFAOYSA-N 0.000 claims 1
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
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- 239000000203 mixture Substances 0.000 description 39
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- 239000000047 product Substances 0.000 description 19
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 17
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- IGHGOYDCVRUTSU-UHFFFAOYSA-M sodium;2-hydroxypropane-1,2,3-tricarboxylic acid;hydroxide Chemical compound [OH-].[Na+].OC(=O)CC(O)(C(O)=O)CC(O)=O IGHGOYDCVRUTSU-UHFFFAOYSA-M 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-N sodium;5-ethyl-5-pentan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)NC1=O QGMRQYFBGABWDR-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- HZTXOKYBDOFKIR-UHFFFAOYSA-N tert-butyl n-(6-cyano-2,3,4,9-tetrahydro-1h-carbazol-3-yl)carbamate Chemical compound N1C2=CC=C(C#N)C=C2C2=C1CCC(NC(=O)OC(C)(C)C)C2 HZTXOKYBDOFKIR-UHFFFAOYSA-N 0.000 description 1
- GUQWIDZADFDWOI-UHFFFAOYSA-N tert-butyl n-[6-(cyanomethyl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]carbamate Chemical compound N1C2=CC=C(CC#N)C=C2C2=C1CCC(NC(=O)OC(C)(C)C)C2 GUQWIDZADFDWOI-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 to carbon atoms of the ring 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919113802A GB9113802D0 (en) | 1991-06-26 | 1991-06-26 | Medicaments |
| PCT/GB1992/001082 WO1993000086A1 (en) | 1991-06-26 | 1992-06-17 | Use of tetrahydrocarbazone derivatives as 5ht1 receptor agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK280907B6 true SK280907B6 (sk) | 2000-09-12 |
Family
ID=10697363
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1319-93A SK280905B6 (sk) | 1991-06-26 | 1992-06-17 | 3-metylamino-6-karboxamido-1,2,3,4-tetrahydrokarbazol, spôsob jeho prípravy, farmaceutický prípravok s jeho obsahom a jeho použitie |
| SK1054-98A SK280906B6 (sk) | 1991-06-26 | 1992-06-17 | Použitie tetrahydrokarbazolových derivátov |
| SK1685-98A SK280907B6 (sk) | 1991-06-26 | 1992-06-17 | Deriváty tetrahydrokarbazolu, spôsob ich prípravy a farmaceutický prípravok s ich obsahom |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1319-93A SK280905B6 (sk) | 1991-06-26 | 1992-06-17 | 3-metylamino-6-karboxamido-1,2,3,4-tetrahydrokarbazol, spôsob jeho prípravy, farmaceutický prípravok s jeho obsahom a jeho použitie |
| SK1054-98A SK280906B6 (sk) | 1991-06-26 | 1992-06-17 | Použitie tetrahydrokarbazolových derivátov |
Country Status (34)
| Country | Link |
|---|---|
| US (2) | US5464864A (cs) |
| EP (1) | EP0591280B1 (cs) |
| JP (1) | JP3261502B2 (cs) |
| KR (1) | KR100251571B1 (cs) |
| CN (1) | CN1034072C (cs) |
| AP (1) | AP344A (cs) |
| AT (1) | ATE170746T1 (cs) |
| BR (2) | BR9206237A (cs) |
| CA (1) | CA2113726C (cs) |
| CZ (3) | CZ282083B6 (cs) |
| DE (2) | DE69226953T2 (cs) |
| DK (1) | DK0591280T3 (cs) |
| FI (1) | FI103967B (cs) |
| GB (1) | GB9113802D0 (cs) |
| HU (1) | HU218907B (cs) |
| IE (1) | IE922062A1 (cs) |
| IL (4) | IL102322A (cs) |
| LU (1) | LU90939I2 (cs) |
| MA (1) | MA22563A1 (cs) |
| MX (1) | MX9203444A (cs) |
| NL (1) | NL300103I2 (cs) |
| NO (2) | NO304774B1 (cs) |
| NZ (1) | NZ243288A (cs) |
| PL (3) | PL169410B1 (cs) |
| PT (1) | PT100620B (cs) |
| RU (1) | RU2137474C1 (cs) |
| SA (1) | SA92130141B1 (cs) |
| SG (1) | SG47877A1 (cs) |
| SI (1) | SI9200125B (cs) |
| SK (3) | SK280905B6 (cs) |
| TW (1) | TW214544B (cs) |
| UA (1) | UA41254C2 (cs) |
| WO (1) | WO1993000086A1 (cs) |
| ZA (1) | ZA924658B (cs) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9211277D0 (en) | 1992-05-28 | 1992-07-15 | Glaxo Group Inc | Pharmaceutical compositions |
| GB9226566D0 (en) * | 1992-12-21 | 1993-02-17 | Smithkline Beecham Plc | Compounds |
| US5616603A (en) * | 1995-05-26 | 1997-04-01 | Smithkline Beecham Plc | Enantiomers of carbazole derivatives as 5-HT1 -like agonists |
| GB9226530D0 (en) * | 1992-12-21 | 1993-02-17 | Smithkline Beecham Plc | Compounds |
| US5618948A (en) * | 1995-05-26 | 1997-04-08 | Smithkline Beecham P.L.C. | Process for preparing an enantiomer of a carbazole derivative |
| EP0749962B1 (en) * | 1995-06-23 | 2000-11-02 | Eli Lilly And Company | 6-substituted-1,2,3,4-tetrahydro-9H-carbazoles and 7-substituted-10H-cyclohepta(7,6-B)indoles |
| US5917054A (en) * | 1995-07-18 | 1999-06-29 | Smithkline Beecham P.L.C. | Process for preparing enantiomers of carbazole derivatives as 5-HT1 -like agonists |
| US5708187A (en) * | 1996-06-27 | 1998-01-13 | Eli Lilly And Company | 6-substituted-1,2,3,4-tetrahydro-9H-carbazoles and 7-substituted-10H-cyclohepta 7,6-B!indoles: New 5-HT1F agonists |
| US5891885A (en) * | 1996-10-09 | 1999-04-06 | Algos Pharmaceutical Corporation | Method for treating migraine |
| GB9723061D0 (en) * | 1997-10-31 | 1998-01-07 | Vanguard Medica Ltd | Medicaments |
| US6066092A (en) * | 1997-11-06 | 2000-05-23 | Cady; Roger K. | Preemptive prophylaxis of migraine device and method |
| US7189753B1 (en) | 1997-11-06 | 2007-03-13 | Cady Roger K | Preemptive prophylaxis of migraine |
| GB9808069D0 (en) | 1998-04-16 | 1998-06-17 | Vanguard Medica Ltd | Novel processes |
| GB9817911D0 (en) * | 1998-08-17 | 1998-10-14 | Vanguard Medica Ltd | New use |
| US20030198669A1 (en) * | 2001-07-05 | 2003-10-23 | R.T. Alamo Ventures I, Llc | Compositions and methods for rapid dissolving formulations of dihydroergotamine and caffeine for the treatment of migraine |
| US20030017175A1 (en) * | 2001-07-05 | 2003-01-23 | R.T. Alamo Ventures I, Inc. | Sublingual administration of dihydroergotamine for the treatment of migraine |
| US6685951B2 (en) | 2001-07-05 | 2004-02-03 | R. T. Alamo Ventures I, Inc. | Administration of dihydroergotamine as a sublingual spray or aerosol for the treatment of migraine |
| DE60221683T2 (de) * | 2001-09-28 | 2008-04-30 | F. Hoffmann-La Roche Ag | Pseudopolymorphe formen von carvedilol |
| MXPA04012834A (es) | 2002-06-21 | 2005-04-25 | Suven Life Sciences Ltd | Arilalquil indoles novedosos que tienen afinidad por el receptor de la serotonina, utiles como agentes terapeuticos, proceso para su preparacion y composiciones farmaceuticas que los contienen. |
| WO2004000849A2 (en) | 2002-06-21 | 2003-12-31 | Suven Life Sciences Limited | Tetracyclic arylsulfonyl indoles having serotonin receptor affinity |
| CA2507505C (en) | 2002-11-28 | 2011-10-04 | Suven Life Sciences Limited | N-arylsulfonyl-3-aminoalkoxyindoles |
| US7875605B2 (en) | 2002-11-28 | 2011-01-25 | Suven Life Sciences Limited | N-arylsulfonyl-3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical composition containing them |
| DE60312226T2 (de) | 2002-12-18 | 2007-11-15 | Suven Life Sciences Ltd. | Tetrazyklische 3-substituierte indole mit serotoninrezeptoraffinität |
| RU2430088C2 (ru) * | 2004-07-14 | 2011-09-27 | Центарис Гмбх | Производные тетрагидрокарбазола и фармацевтическая композиция на их основе |
| US7601856B2 (en) | 2006-07-27 | 2009-10-13 | Wyeth | Benzofurans as potassium ion channel modulators |
| JP5220013B2 (ja) * | 2006-08-07 | 2013-06-26 | アクテリオン ファーマシューティカルズ リミテッド | （３−アミノ−１，２，３，４−テトラヒドロ−９ｈ−カルバゾール−９−イル）−酢酸誘導体 |
| SI2124556T1 (sl) | 2006-10-09 | 2015-01-30 | Charleston Laboratories, Inc. | Farmacevtske sestave |
| ES2538082T3 (es) | 2007-02-11 | 2015-06-17 | Map Pharmaceuticals Inc | Método de administración terapéutica de DHE para permitir el rápido alivio de migraña mientras que se minimiza el perfil de efectos secundarios |
| US20090069399A1 (en) * | 2007-09-12 | 2009-03-12 | Protia, Llc | Deuterium-enriched frovatriptan |
| CA2749273C (en) | 2008-01-09 | 2018-09-04 | Charleston Laboratories, Inc. | Pharmaceutical oral dosage form comprising a triptan and an antiemetic |
| WO2010073253A1 (en) * | 2008-12-22 | 2010-07-01 | Natco Pharma Limited | Method for preparing an optically active frovatriptan |
| EP3311667A1 (en) | 2009-07-08 | 2018-04-25 | Charleston Laboratories, Inc. | Pharmaceutical compositions |
| US10098674B2 (en) | 2009-10-22 | 2018-10-16 | Nuvasive, Inc. | System and method for posterior cervical fusion |
| US9204906B2 (en) | 2009-10-22 | 2015-12-08 | Nuvasive, Inc. | Posterior cervical fusion system and techniques |
| WO2013016223A2 (en) | 2011-07-22 | 2013-01-31 | The University Of Chicago | Treatments for migraine and related disorders |
| HK1216250A1 (zh) | 2012-12-21 | 2016-10-28 | Map Pharmaceuticals, Inc. | 8'-羟基-二氢麦角胺化合物及组合物 |
| EP2816030A1 (en) | 2013-06-20 | 2014-12-24 | Duke Chem, S. A. | Process for the preparation of frovatriptan and its enantiomer |
| GB201312768D0 (en) | 2013-07-17 | 2013-08-28 | Ge Healthcare Ltd | Work-up procedure |
| JP2019507181A (ja) | 2016-03-04 | 2019-03-14 | チャールストン ラボラトリーズ，インコーポレイテッド | 医薬組成物 |
| EP3766483A1 (en) | 2019-07-19 | 2021-01-20 | BioPharma Synergies, S. L. | Orodispersible powder composition comprising a triptan |
| WO2025038666A2 (en) * | 2023-08-13 | 2025-02-20 | GATC Health Corp | Compounds and methods for treating addiction |
| CN119499195A (zh) * | 2024-11-26 | 2025-02-25 | 青岛国信制药有限公司 | 一种快速吸收琥珀酸呋罗曲坦片及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3642816A (en) * | 1967-08-10 | 1972-02-15 | Sterling Drug Inc | 3-acetamido-1 2 3 4-tetrahydrocarbazole |
| US3959309A (en) | 1968-01-24 | 1976-05-25 | Sterling Drug Inc. | 3-Amido-1,2,3,4-tetrahydrocarbazoles |
| US4062864A (en) * | 1968-01-24 | 1977-12-13 | Sterling Drug Inc. | 3-Hydroxy carbazole derivatives |
| US3592824A (en) * | 1970-03-12 | 1971-07-13 | Miles Lab | 3-substituted amino-1,2,3,4-tetrahydrocarbazoles |
| US4172834A (en) | 1971-08-16 | 1979-10-30 | Sterling Drug Inc. | 3-Amino-tetrahydrocarbazoles |
| BE787537A (fr) * | 1971-08-16 | 1973-02-14 | Sterling Drug Inc | Tetrahydrocarbazoles |
| DE2815926A1 (de) * | 1978-04-13 | 1979-10-18 | Boehringer Mannheim Gmbh | Neue carbazolyl-(4)-oxy-propanolamin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4257952A (en) * | 1977-06-06 | 1981-03-24 | Sterling Drug Inc. | 3-Amino-tetrahydrocarbazoles |
| US4254134A (en) * | 1978-03-17 | 1981-03-03 | Endo Laboratories, Inc. | Antidepressant 2-amino- and -2-(substituted amino)-cis-hexahydro-carbazoles |
| EP0115607A1 (de) * | 1983-01-04 | 1984-08-15 | MERCK PATENT GmbH | Tetrahydrocarbazolderivate |
-
1991
- 1991-06-26 GB GB919113802A patent/GB9113802D0/en active Pending
-
1992
- 1992-06-17 KR KR1019930704055A patent/KR100251571B1/ko not_active Expired - Lifetime
- 1992-06-17 DE DE69226953T patent/DE69226953T2/de not_active Expired - Lifetime
- 1992-06-17 DE DE2002199042 patent/DE10299042I2/de active Active
- 1992-06-17 PL PL92307118A patent/PL169410B1/pl unknown
- 1992-06-17 CA CA002113726A patent/CA2113726C/en not_active Expired - Lifetime
- 1992-06-17 SK SK1319-93A patent/SK280905B6/sk not_active IP Right Cessation
- 1992-06-17 JP JP51108692A patent/JP3261502B2/ja not_active Expired - Lifetime
- 1992-06-17 CZ CS932861A patent/CZ282083B6/cs not_active IP Right Cessation
- 1992-06-17 SK SK1054-98A patent/SK280906B6/sk not_active IP Right Cessation
- 1992-06-17 US US08/167,846 patent/US5464864A/en not_active Expired - Lifetime
- 1992-06-17 BR BR9206237A patent/BR9206237A/pt not_active Application Discontinuation
- 1992-06-17 HU HU9303731A patent/HU218907B/hu active IP Right Revival
- 1992-06-17 DK DK92912379T patent/DK0591280T3/da active
- 1992-06-17 UA UA93002251A patent/UA41254C2/uk unknown
- 1992-06-17 PL PL92311304A patent/PL171034B1/pl unknown
- 1992-06-17 SG SG1996004938A patent/SG47877A1/en unknown
- 1992-06-17 WO PCT/GB1992/001082 patent/WO1993000086A1/en not_active Ceased
- 1992-06-17 AT AT92912379T patent/ATE170746T1/de active
- 1992-06-17 EP EP92912379A patent/EP0591280B1/en not_active Expired - Lifetime
- 1992-06-17 CZ CZ961506A patent/CZ150696A3/cs not_active IP Right Cessation
- 1992-06-17 RU RU93058534A patent/RU2137474C1/ru active Protection Beyond IP Right Term
- 1992-06-17 SK SK1685-98A patent/SK280907B6/sk not_active IP Right Cessation
- 1992-06-17 CZ CZ961505A patent/CZ282061B6/cs not_active IP Right Cessation
- 1992-06-17 PL PL92301883A patent/PL169392B1/pl unknown
- 1992-06-24 PT PT100620A patent/PT100620B/pt not_active IP Right Cessation
- 1992-06-24 ZA ZA924658A patent/ZA924658B/xx unknown
- 1992-06-24 MA MA22853A patent/MA22563A1/fr unknown
- 1992-06-24 NZ NZ243288A patent/NZ243288A/en not_active IP Right Cessation
- 1992-06-25 TW TW081104991A patent/TW214544B/zh not_active IP Right Cessation
- 1992-06-25 IL IL102322A patent/IL102322A/xx not_active IP Right Cessation
- 1992-06-25 IL IL11710596A patent/IL117105A0/xx unknown
- 1992-06-25 IL IL117104A patent/IL117104A/xx not_active IP Right Cessation
- 1992-06-25 IL IL117105A patent/IL117105A/en not_active IP Right Cessation
- 1992-06-25 AP APAP/P/1992/000403A patent/AP344A/en active
- 1992-06-25 CN CN92108831A patent/CN1034072C/zh not_active Expired - Lifetime
- 1992-06-26 SI SI9200125A patent/SI9200125B/sl unknown
- 1992-06-26 MX MX9203444A patent/MX9203444A/es unknown
- 1992-07-01 IE IE206292A patent/IE922062A1/en not_active IP Right Cessation
- 1992-10-04 SA SA92130141A patent/SA92130141B1/ar unknown
-
1993
- 1993-12-23 FI FI935842A patent/FI103967B/fi not_active IP Right Cessation
- 1993-12-23 NO NO934759A patent/NO304774B1/no not_active IP Right Cessation
-
1995
- 1995-05-15 US US08/442,719 patent/US5637611A/en not_active Expired - Lifetime
-
1997
- 1997-05-06 BR BR1100460-6A patent/BR1100460A/pt active IP Right Grant
-
2002
- 2002-07-24 LU LU90939C patent/LU90939I2/fr unknown
- 2002-10-14 NL NL300103C patent/NL300103I2/nl unknown
-
2005
- 2005-05-03 NO NO2005011C patent/NO2005011I2/no unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Expiry date: 20120617 |