KR940006584A - 멀미 및 구토 치료용 6-헤데로시클릭-4-아미노-1,3,4,5-테트라하이드로벤즈[cd]인돌 - Google Patents
멀미 및 구토 치료용 6-헤데로시클릭-4-아미노-1,3,4,5-테트라하이드로벤즈[cd]인돌 Download PDFInfo
- Publication number
- KR940006584A KR940006584A KR1019930020227A KR930020227A KR940006584A KR 940006584 A KR940006584 A KR 940006584A KR 1019930020227 A KR1019930020227 A KR 1019930020227A KR 930020227 A KR930020227 A KR 930020227A KR 940006584 A KR940006584 A KR 940006584A
- Authority
- KR
- South Korea
- Prior art keywords
- tetrahydrobenz
- indole
- propylamino
- alkyl
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 201000003152 motion sickness Diseases 0.000 title claims abstract 4
- 206010047700 Vomiting Diseases 0.000 title claims abstract 3
- 230000008673 vomiting Effects 0.000 title claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- QEEUUCCJDYUBFJ-HNNXBMFYSA-N (4r)-6-(1,3-oxazol-2-yl)-n,n-dipropyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C([C@@H](CC1=C23)N(CCC)CCC)C2=CNC3=CC=C1C1=NC=CO1 QEEUUCCJDYUBFJ-HNNXBMFYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- MRUNDFRAOWUTJX-HNNXBMFYSA-N (4r)-6-(1,2-oxazol-3-yl)-n,n-dipropyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C([C@@H](CC1=C23)N(CCC)CCC)C2=CNC3=CC=C1C=1C=CON=1 MRUNDFRAOWUTJX-HNNXBMFYSA-N 0.000 claims 1
- CLFBIROENREVCF-HNNXBMFYSA-N (4r)-6-(1,2-oxazol-5-yl)-n,n-dipropyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C([C@@H](CC1=C23)N(CCC)CCC)C2=CNC3=CC=C1C1=CC=NO1 CLFBIROENREVCF-HNNXBMFYSA-N 0.000 claims 1
- WVWRMVCFJMZWKO-HNNXBMFYSA-N (4r)-6-(1,3-oxazol-5-yl)-n,n-dipropyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C([C@@H](CC1=C23)N(CCC)CCC)C2=CNC3=CC=C1C1=CN=CO1 WVWRMVCFJMZWKO-HNNXBMFYSA-N 0.000 claims 1
- DLENVBXYLRODJF-FQEVSTJZSA-N (4r)-6-(3-phenyl-2h-oxadiazol-5-yl)-n,n-dipropyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C([C@@H](CC1=C23)N(CCC)CCC)C2=CNC3=CC=C1C(ON1)=CN1C1=CC=CC=C1 DLENVBXYLRODJF-FQEVSTJZSA-N 0.000 claims 1
- ZPMJZDIHLNEYOP-KRWDZBQOSA-N (4r)-n,n-bis(cyclopropylmethyl)-6-(1,2-oxazol-5-yl)-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C1CC1CN([C@@H]1CC=2C(C=3ON=CC=3)=CC=C3NC=C(C=23)C1)CC1CC1 ZPMJZDIHLNEYOP-KRWDZBQOSA-N 0.000 claims 1
- LUXQMFSFBRSFPW-KRWDZBQOSA-N (4r)-n,n-bis(cyclopropylmethyl)-6-(1,3-oxazol-5-yl)-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C1CC1CN([C@@H]1CC=2C(C=3OC=NC=3)=CC=C3NC=C(C=23)C1)CC1CC1 LUXQMFSFBRSFPW-KRWDZBQOSA-N 0.000 claims 1
- IPNDYAWKQOVUSS-LBPRGKRZSA-N (4r)-n,n-dimethyl-6-(1h-pyrazol-4-yl)-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C([C@@H](CC1=C23)N(C)C)C2=CNC3=CC=C1C=1C=NNC=1 IPNDYAWKQOVUSS-LBPRGKRZSA-N 0.000 claims 1
- SITVQJDQZXARCM-HNNXBMFYSA-N (4r)-n,n-dipropyl-6-(1,3-thiazol-2-yl)-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C([C@@H](CC1=C23)N(CCC)CCC)C2=CNC3=CC=C1C1=NC=CS1 SITVQJDQZXARCM-HNNXBMFYSA-N 0.000 claims 1
- UEXOTVUUCUMYPS-HNNXBMFYSA-N (4r)-n,n-dipropyl-6-(1,3-thiazol-5-yl)-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C([C@@H](CC1=C23)N(CCC)CCC)C2=CNC3=CC=C1C1=CN=CS1 UEXOTVUUCUMYPS-HNNXBMFYSA-N 0.000 claims 1
- NIUKGBYRTPUOPO-HNNXBMFYSA-N (4r)-n,n-dipropyl-6-(1h-pyrazol-5-yl)-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C([C@@H](CC1=C23)N(CCC)CCC)C2=CNC3=CC=C1C1=CC=NN1 NIUKGBYRTPUOPO-HNNXBMFYSA-N 0.000 claims 1
- CMKKCWBNVBZBMZ-SFHVURJKSA-N (4r)-n,n-dipropyl-6-pyridin-4-yl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C([C@@H](CC1=C23)N(CCC)CCC)C2=CNC3=CC=C1C1=CC=NC=C1 CMKKCWBNVBZBMZ-SFHVURJKSA-N 0.000 claims 1
- MRUNDFRAOWUTJX-OAHLLOKOSA-N (4s)-6-(1,2-oxazol-3-yl)-n,n-dipropyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C([C@H](CC1=C23)N(CCC)CCC)C2=CNC3=CC=C1C=1C=CON=1 MRUNDFRAOWUTJX-OAHLLOKOSA-N 0.000 claims 1
- -1 3-pyrazolyl Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010028813 Nausea Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- NIUKGBYRTPUOPO-UHFFFAOYSA-N n,n-dipropyl-6-(1h-pyrazol-5-yl)-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C12=C3CC(N(CCC)CCC)CC2=CNC1=CC=C3C1=CC=NN1 NIUKGBYRTPUOPO-UHFFFAOYSA-N 0.000 claims 1
- YMSMRDRCQRZDBG-UHFFFAOYSA-N n,n-dipropyl-6-pyridin-2-yl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C12=C3CC(N(CCC)CCC)CC2=CNC1=CC=C3C1=CC=CC=N1 YMSMRDRCQRZDBG-UHFFFAOYSA-N 0.000 claims 1
- 230000008693 nausea Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract 4
- 150000002475 indoles Chemical class 0.000 abstract 1
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
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- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Otolaryngology (AREA)
- Urology & Nephrology (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/954,105 US5364856A (en) | 1991-03-28 | 1992-09-30 | 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[CD]indoles |
| US954,105 | 1992-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR940006584A true KR940006584A (ko) | 1994-04-25 |
Family
ID=25494930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930020227A Ceased KR940006584A (ko) | 1992-09-30 | 1993-09-28 | 멀미 및 구토 치료용 6-헤데로시클릭-4-아미노-1,3,4,5-테트라하이드로벤즈[cd]인돌 |
Country Status (15)
| Country | Link |
|---|---|
| US (10) | US5364856A (enExample) |
| EP (2) | EP0590971A1 (enExample) |
| JP (1) | JPH06211655A (enExample) |
| KR (1) | KR940006584A (enExample) |
| CN (1) | CN1056144C (enExample) |
| AU (1) | AU676849B2 (enExample) |
| CA (1) | CA2107010A1 (enExample) |
| CZ (1) | CZ9302010A3 (enExample) |
| HU (1) | HUT66076A (enExample) |
| IL (1) | IL107125A (enExample) |
| MX (1) | MX9305998A (enExample) |
| NO (1) | NO933477L (enExample) |
| RU (1) | RU2138262C1 (enExample) |
| TW (1) | TW248558B (enExample) |
| ZA (1) | ZA937153B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5347013A (en) * | 1991-03-28 | 1994-09-13 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz[cd]indoles |
| US5643934A (en) * | 1991-03-28 | 1997-07-01 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz [CD]indoles |
| TW248556B (enExample) * | 1993-01-18 | 1995-06-01 | Takeda Pharm Industry Co | |
| US5385928A (en) * | 1994-05-18 | 1995-01-31 | Eli Lilly And Company | Tetrahydrobenz [CD] indazoles, compositions and use |
| US5990114A (en) * | 1996-02-28 | 1999-11-23 | Recordati, S.A., Chemical And Pharmaceutical Company | Use of 5-HT1A receptor antagonists for the treatment of urinary incontinence |
| US7189753B1 (en) | 1997-11-06 | 2007-03-13 | Cady Roger K | Preemptive prophylaxis of migraine |
| EP1083918A1 (en) * | 1998-06-08 | 2001-03-21 | Advanced Medicine, Inc. | Novel therapeutic agents that modulate 5-ht receptors |
| WO2000073277A1 (en) * | 1999-06-02 | 2000-12-07 | Ishihara Sangyo Kaisha, Ltd. | Fused tricyclic compounds, process for their preparation, and herbicidal compositions containing them |
| US6770596B1 (en) | 2000-04-21 | 2004-08-03 | Ishihara Sangyo Kaisha Ltd. | Fused tricyclic compounds, process for their preparation, and herbicidal compositions containing them |
| RU2197961C2 (ru) * | 2000-07-17 | 2003-02-10 | Центр по разработке эластомеров Казанского государственного технологического университета | Средство для профилактики и купирования тошноты и рвоты |
| KR20140145141A (ko) | 2012-03-30 | 2014-12-22 | 클래리언트 다이아그노스틱 서비시즈, 인크. | 생물학적 샘플의 영상 생성 방법 |
| CN111265268A (zh) * | 2018-12-05 | 2020-06-12 | 苏州英途康医疗科技有限公司 | 医疗器械 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3194811A (en) * | 1963-09-05 | 1965-07-13 | Merck & Co Inc | Aroyl-benzindolyl acids |
| BE755270A (fr) * | 1969-08-27 | 1971-02-25 | Sandoz Sa | Nouveaux derives du benzo(cd)indole, leur preparation et medicaments contenant ces derives |
| CH517732A (de) * | 1969-10-24 | 1972-01-15 | Sandoz Ag | Verfahren zur Herstellung neuer Guanidin- Verbindungen |
| BE757879A (fr) * | 1969-10-24 | 1971-04-22 | Sandoz Sa | Derives du benzo(cd)indole, leur preparation et medicaments contenant ces derives |
| FI206974A7 (enExample) * | 1973-07-16 | 1975-01-17 | Sandoz Ag | |
| US4110339A (en) * | 1977-11-25 | 1978-08-29 | Eli Lilly And Company | 4-(Di-n-propyl)amino-1,3,4,5-tetrahydrobenz[cd]indole |
| ZA795239B (en) * | 1978-10-12 | 1980-11-26 | Glaxo Group Ltd | Heterocyclic compounds |
| US4282240A (en) * | 1979-11-23 | 1981-08-04 | Merck & Co., Inc. | Amino substituted tetrahydrobenzindoles |
| FR2510111A1 (fr) * | 1981-07-24 | 1983-01-28 | Roussel Uclaf | Nouveaux derives du piperidin-3-yl indole, leurs sels, leur procede de preparation, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant |
| FR2522658A1 (fr) * | 1982-03-05 | 1983-09-09 | Roussel Uclaf | Application a titre de medicaments de derives du trans 4-amino benz (c,d) indol-5-ol ainsi que de leurs sels, compositions les renfermant, nouveaux derives et leur procede de preparation |
| JPS5969151A (ja) * | 1982-10-13 | 1984-04-19 | Unitika Ltd | 球状イオン交換樹脂とその製造法及び吸着処理法 |
| DE3346573A1 (de) * | 1983-12-23 | 1985-07-04 | Troponwerke GmbH & Co KG, 5000 Köln | 1,3,4,5-tetrahydrobenz(c,d)indole, ein verfahren zu ihrer herstellung und ihre verwendung |
| US4983622A (en) * | 1984-02-06 | 1991-01-08 | Eli Lilly And Company | 6-substituted-4-dialkylaminotetrahydrobenz(c,d)indoles |
| US4576959A (en) * | 1984-02-06 | 1986-03-18 | Eli Lilly And Company | 6-Substituted-4-dialkylaminotetrahydrobenz[c,d]indoles |
| IL74222A (en) * | 1984-02-06 | 1988-07-31 | Lilly Co Eli | 6-substituted-4-dialkylamino tetrahydrobenz(c,d)indoles,their preparation and pharmaceutical compositions comprising them |
| CA1266482A1 (en) * | 1984-05-24 | 1990-03-06 | Carl Kaiser | 6-oxygenated-1,3,4,5-tetrahydrobenz(cd)indol-4-amines |
| DE3525564A1 (de) * | 1985-07-15 | 1987-02-05 | Schering Ag | Tricyclische verbindungen mit indolstruktur, verfahren zu ihrer herstellung und deren verwendung als arzneimittel |
| US4745126A (en) * | 1987-03-12 | 1988-05-17 | Eli Lilly And Company | Method of treating anxiety with tetrahydrobenz[c,d]indole-6-carboxamides |
| US4943428A (en) * | 1987-07-10 | 1990-07-24 | Wright State University | Stimulation of serotonin-1A receptors in mammals to alleviate motion sickness and emesis induced by chemical agents |
| DE3809155A1 (de) * | 1988-03-18 | 1989-09-28 | Bayer Ag | 1,3,4,5-tetrahydrobenz-(c,d)-indole |
| GB8824744D0 (en) * | 1988-10-21 | 1988-11-30 | Erba Carlo Spa | Antiemesis ergoline derivatives |
| US5204340A (en) * | 1989-04-11 | 1993-04-20 | Eli Lilly And Company | Tetrahydrobenz(c,d)indole serotonin agonists |
| US4977172A (en) * | 1989-09-29 | 1990-12-11 | Warner-Lambert Company | Method of treating the symptoms of cognitive decline in an elderly patient employing (S)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)-methyl]-2-oxazolidinone |
| US5039820A (en) * | 1990-02-26 | 1991-08-13 | Eli Lilly And Company | 4-amino-6-iodo-hexahydrobenz(cd)indoles |
| TW219933B (enExample) * | 1990-02-26 | 1994-02-01 | Lilly Co Eli | |
| US5302612A (en) * | 1990-02-26 | 1994-04-12 | Eli Lilly And Company | 6-substituted-hexahydrobenz[cd]indoles |
| US5212319A (en) * | 1990-02-26 | 1993-05-18 | Eli Lilly And Company | Intermediates to 4-amino-hexahydrobenz[cd]indoles and processes therefor |
| US5397779A (en) * | 1990-06-15 | 1995-03-14 | Roussel-Uclaf | Cephalosporins |
| US5229410A (en) * | 1990-08-15 | 1993-07-20 | Eli Lilly And Company | 6-substituted-hexahydrobenz[cd]indoles |
| US5643934A (en) * | 1991-03-28 | 1997-07-01 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz [CD]indoles |
| US5244912A (en) * | 1991-03-28 | 1993-09-14 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz(cd)indoles and pharmaceutical use thereof |
| US5347013A (en) * | 1991-03-28 | 1994-09-13 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz[cd]indoles |
| US5266571A (en) * | 1992-01-09 | 1993-11-30 | Amer Moh Samir | Treatment of hemorrhoids with 5-HT2 antagonists |
-
1992
- 1992-09-30 US US07/954,105 patent/US5364856A/en not_active Expired - Fee Related
-
1993
- 1993-09-27 CZ CZ932010A patent/CZ9302010A3/cs unknown
- 1993-09-27 ZA ZA937153A patent/ZA937153B/xx unknown
- 1993-09-27 TW TW082107947A patent/TW248558B/zh active
- 1993-09-27 CA CA002107010A patent/CA2107010A1/en not_active Abandoned
- 1993-09-27 IL IL10712593A patent/IL107125A/en not_active IP Right Cessation
- 1993-09-28 KR KR1019930020227A patent/KR940006584A/ko not_active Ceased
- 1993-09-28 HU HU9302749A patent/HUT66076A/hu unknown
- 1993-09-28 AU AU48682/93A patent/AU676849B2/en not_active Ceased
- 1993-09-28 MX MX9305998A patent/MX9305998A/es unknown
- 1993-09-29 CN CN93114191A patent/CN1056144C/zh not_active Expired - Fee Related
- 1993-09-29 NO NO933477A patent/NO933477L/no not_active Application Discontinuation
- 1993-09-29 EP EP93307747A patent/EP0590971A1/en not_active Ceased
- 1993-09-29 JP JP5242612A patent/JPH06211655A/ja active Pending
- 1993-09-29 EP EP99202258A patent/EP1000621A3/en not_active Withdrawn
- 1993-09-29 RU RU93054754A patent/RU2138262C1/ru active
-
1994
- 1994-08-31 US US08/299,175 patent/US5594019A/en not_active Expired - Fee Related
-
1995
- 1995-05-31 US US08/455,774 patent/US5641797A/en not_active Expired - Fee Related
- 1995-05-31 US US08/456,256 patent/US5674884A/en not_active Expired - Fee Related
- 1995-05-31 US US08/454,798 patent/US5750554A/en not_active Expired - Fee Related
- 1995-05-31 US US08/455,431 patent/US5736562A/en not_active Expired - Fee Related
- 1995-05-31 US US08/456,225 patent/US5643930A/en not_active Expired - Fee Related
- 1995-05-31 US US08/454,888 patent/US5665743A/en not_active Expired - Fee Related
- 1995-05-31 US US08/454,900 patent/US5665758A/en not_active Expired - Fee Related
- 1995-05-31 US US08/456,974 patent/US5624944A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2107010A1 (en) | 1994-03-31 |
| US5643930A (en) | 1997-07-01 |
| HU9302749D0 (en) | 1993-12-28 |
| US5624944A (en) | 1997-04-29 |
| AU4868293A (en) | 1994-07-14 |
| EP1000621A3 (en) | 2003-05-14 |
| ZA937153B (en) | 1995-03-27 |
| US5594019A (en) | 1997-01-14 |
| EP0590971A1 (en) | 1994-04-06 |
| TW248558B (enExample) | 1995-06-01 |
| US5641797A (en) | 1997-06-24 |
| NO933477L (no) | 1994-04-05 |
| CN1056144C (zh) | 2000-09-06 |
| US5736562A (en) | 1998-04-07 |
| IL107125A0 (en) | 1993-12-28 |
| JPH06211655A (ja) | 1994-08-02 |
| US5364856A (en) | 1994-11-15 |
| HUT66076A (en) | 1994-09-28 |
| NO933477D0 (no) | 1993-09-29 |
| RU2138262C1 (ru) | 1999-09-27 |
| US5665758A (en) | 1997-09-09 |
| US5674884A (en) | 1997-10-07 |
| IL107125A (en) | 1998-09-24 |
| US5665743A (en) | 1997-09-09 |
| EP1000621A2 (en) | 2000-05-17 |
| MX9305998A (es) | 1995-01-31 |
| US5750554A (en) | 1998-05-12 |
| AU676849B2 (en) | 1997-03-27 |
| CZ9302010A3 (en) | 1994-05-18 |
| CN1094724A (zh) | 1994-11-09 |
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