NO301642B1 - 6-heterocykliske-4-amino-1,3,4,5-tetrahydrobenz-(cd)indoler og farmasöytisk formulering - Google Patents
6-heterocykliske-4-amino-1,3,4,5-tetrahydrobenz-(cd)indoler og farmasöytisk formulering Download PDFInfo
- Publication number
- NO301642B1 NO301642B1 NO921128A NO921128A NO301642B1 NO 301642 B1 NO301642 B1 NO 301642B1 NO 921128 A NO921128 A NO 921128A NO 921128 A NO921128 A NO 921128A NO 301642 B1 NO301642 B1 NO 301642B1
- Authority
- NO
- Norway
- Prior art keywords
- indole
- solution
- propylamino
- tetrahydrobenz
- mmol
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 150000002475 indoles Chemical class 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 100
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 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
- 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 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
- HHJAHIKNLLDIQA-OAHLLOKOSA-N (4r)-6-(3h-oxadiazol-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=C1N1NC=CO1 HHJAHIKNLLDIQA-OAHLLOKOSA-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
- DZHJPXKHVYZWFZ-KRWDZBQOSA-N (4r)-n,n-bis(cyclopropylmethyl)-6-(1h-pyrazol-5-yl)-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C1CC1CN([C@@H]1CC=2C(C3=NNC=C3)=CC=C3NC=C(C=23)C1)CC1CC1 DZHJPXKHVYZWFZ-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
- 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
- BKAWJIRCKVUVED-UHFFFAOYSA-N 5-(2-hydroxyethyl)-4-methylthiazole Chemical compound CC=1N=CSC=1CCO BKAWJIRCKVUVED-UHFFFAOYSA-N 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
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 18
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- 239000000243 solution Substances 0.000 description 121
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- 238000002360 preparation method Methods 0.000 description 42
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- 238000006243 chemical reaction Methods 0.000 description 35
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- 229910002027 silica gel Inorganic materials 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 18
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- -1 n-octyl Chemical group 0.000 description 15
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- ZYVORBSWPVDTCX-UHFFFAOYSA-N 1,2,2a,3-tetrahydrobenzo[cd]indole Chemical class C1=CCC2CNC3=CC=CC1=C32 ZYVORBSWPVDTCX-UHFFFAOYSA-N 0.000 description 8
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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- 238000010561 standard procedure Methods 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
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- VTEKJMLRRQTTAX-UHFFFAOYSA-N tributyl(furan-3-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=1C=COC=1 VTEKJMLRRQTTAX-UHFFFAOYSA-N 0.000 description 1
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- CFQJBWKKHCMCGJ-UHFFFAOYSA-N tributyl(pyridin-3-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CN=C1 CFQJBWKKHCMCGJ-UHFFFAOYSA-N 0.000 description 1
- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- 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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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D405/02—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 containing two hetero rings
- C07D405/04—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 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Anesthesiology (AREA)
- Otolaryngology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/677,016 US5244912A (en) | 1991-03-28 | 1991-03-28 | 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz(cd)indoles and pharmaceutical use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO921128D0 NO921128D0 (no) | 1992-03-23 |
| NO921128L NO921128L (no) | 1992-09-29 |
| NO301642B1 true NO301642B1 (no) | 1997-11-24 |
Family
ID=24716969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO921128A NO301642B1 (no) | 1991-03-28 | 1992-03-23 | 6-heterocykliske-4-amino-1,3,4,5-tetrahydrobenz-(cd)indoler og farmasöytisk formulering |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US5244912A (de) |
| EP (1) | EP0506363B1 (de) |
| JP (1) | JP3159766B2 (de) |
| KR (1) | KR100221158B1 (de) |
| CN (2) | CN1059210C (de) |
| AT (1) | ATE180256T1 (de) |
| AU (1) | AU649319B2 (de) |
| BR (1) | BR9201089A (de) |
| CA (1) | CA2064384A1 (de) |
| CS (1) | CS85692A3 (de) |
| DE (1) | DE69229197T2 (de) |
| DK (1) | DK0506363T3 (de) |
| ES (1) | ES2133303T3 (de) |
| FI (1) | FI921347A (de) |
| GR (1) | GR3030760T3 (de) |
| HK (1) | HK1013824A1 (de) |
| HU (1) | HU217590B (de) |
| IE (1) | IE921001A1 (de) |
| IL (1) | IL101324A (de) |
| MX (1) | MX9201374A (de) |
| MY (1) | MY108450A (de) |
| NO (1) | NO301642B1 (de) |
| NZ (1) | NZ242088A (de) |
| RU (1) | RU2059621C1 (de) |
| YU (1) | YU31492A (de) |
| ZA (1) | ZA922070B (de) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5244911A (en) * | 1991-03-28 | 1993-09-14 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz(cd)indoles and pharmaceutical use thereof |
| US5364856A (en) * | 1991-03-28 | 1994-11-15 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[CD]indoles |
| GB9211277D0 (en) | 1992-05-28 | 1992-07-15 | Glaxo Group Inc | Pharmaceutical compositions |
| NZ314570A (en) * | 1993-06-10 | 2000-11-24 | Lilly Co Eli | Treatment of emesis using tetrahydrobenz[cd]indole-6-carboxamides |
| US5385928A (en) * | 1994-05-18 | 1995-01-31 | Eli Lilly And Company | Tetrahydrobenz [CD] indazoles, compositions and use |
| WO1995032965A1 (fr) * | 1994-06-01 | 1995-12-07 | Yamanouchi Pharmaceutical Co. Ltd. | Derive de l'oxadiazole et composition medicinale a base de ce dernier |
| FR2732964B1 (fr) * | 1995-04-14 | 1997-05-16 | Adir | Nouveaux amides tricycliques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| TW430660B (en) * | 1996-05-30 | 2001-04-21 | Mochida Pharm Co Ltd | Novel benzindole derivatives for neuron cell protection, processes for production, and the pharmaceutical compounds containing them |
| US7189753B1 (en) | 1997-11-06 | 2007-03-13 | Cady Roger K | Preemptive prophylaxis of migraine |
| US6479535B1 (en) * | 1998-05-15 | 2002-11-12 | Wyeth | 2-phenyl-1-[4-(2-aminoethoxy)-benzyl]-indole and estrogen formulations |
| WO1999064044A1 (en) * | 1998-06-08 | 1999-12-16 | Advanced Medicine, Inc. | Novel therapeutic agents that modulate 5-ht receptors |
| KR102355670B1 (ko) | 2013-03-15 | 2022-02-08 | 인사이트 홀딩스 코포레이션 | Bet 단백질 저해제로서의 삼환식 복소환 |
| CA2917319A1 (en) | 2013-07-08 | 2015-01-15 | Incyte Holdings Corporation | Tricyclic heterocycles as bet protein inhibitors |
| US9399640B2 (en) | 2013-11-26 | 2016-07-26 | Incyte Corporation | Substituted pyrrolo[2,3-c]pyridines and pyrazolo[3,4-c]pyridines as BET protein inhibitors |
| WO2015081189A1 (en) | 2013-11-26 | 2015-06-04 | Incyte Corporation | Bicyclic heterocycles as bet protein inhibitors |
| WO2015095492A1 (en) | 2013-12-19 | 2015-06-25 | Incyte Corporation | Tricyclic heterocycles as bet protein inhibitors |
| UA119870C2 (uk) | 2014-04-23 | 2019-08-27 | Інсайт Корпорейшн | 1H-ПІРОЛО[2,3-c]ПІРИДИН-7(6H)-ОНИ ТА ПІРАЗОЛО[3,4-c]ПІРИДИН-7(6H)-ОНИ ЯК ІНГІБІТОРИ БІЛКІВ BET |
| ES2855225T3 (es) | 2014-09-15 | 2021-09-23 | Incyte Corp | Heterociclos tricíclicos para su uso como inhibidores de proteínas BET |
| AR106520A1 (es) | 2015-10-29 | 2018-01-24 | Incyte Corp | Forma sólida amorfa de un inhibidor de proteína bet |
| DK3472157T3 (da) | 2016-06-20 | 2023-05-01 | Incyte Corp | Krystallinske faste former af en bet-inhibitor |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE517732C (de) * | 1927-10-27 | 1931-02-09 | Then Rudolf | Faerbekufe mit einem drehbaren, trommelartigen Rahmen fuer die auf aus-wechselbaren Faerbestoecken aufgehaengten Waren, insbesondere Struempfe |
| 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 |
| BE757879A (fr) * | 1969-10-24 | 1971-04-22 | Sandoz Sa | Derives du benzo(cd)indole, leur preparation et medicaments contenant ces derives |
| FI206974A (de) * | 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 |
| 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 |
| 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 |
| US4576959A (en) * | 1984-02-06 | 1986-03-18 | Eli Lilly And Company | 6-Substituted-4-dialkylaminotetrahydrobenz[c,d]indoles |
| 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 |
| DE3809155A1 (de) * | 1988-03-18 | 1989-09-28 | Bayer Ag | 1,3,4,5-tetrahydrobenz-(c,d)-indole |
| SE8901889D0 (sv) * | 1989-05-26 | 1989-05-26 | Astra Ab | Novel 8-substituted-2-aminotetralines |
| US5244911A (en) * | 1991-03-28 | 1993-09-14 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz(cd)indoles and pharmaceutical use thereof |
-
1991
- 1991-03-28 US US07/677,016 patent/US5244912A/en not_active Expired - Fee Related
-
1992
- 1992-03-20 CS CS92856A patent/CS85692A3/cs unknown
- 1992-03-20 ZA ZA922070A patent/ZA922070B/xx unknown
- 1992-03-20 MY MYPI92000474A patent/MY108450A/en unknown
- 1992-03-22 IL IL10132492A patent/IL101324A/en not_active IP Right Cessation
- 1992-03-23 NZ NZ242088A patent/NZ242088A/en unknown
- 1992-03-23 NO NO921128A patent/NO301642B1/no not_active IP Right Cessation
- 1992-03-25 ES ES92302573T patent/ES2133303T3/es not_active Expired - Lifetime
- 1992-03-25 EP EP92302573A patent/EP0506363B1/de not_active Expired - Lifetime
- 1992-03-25 DK DK92302573T patent/DK0506363T3/da active
- 1992-03-25 DE DE69229197T patent/DE69229197T2/de not_active Expired - Fee Related
- 1992-03-25 AT AT92302573T patent/ATE180256T1/de not_active IP Right Cessation
- 1992-03-25 RU SU925011479A patent/RU2059621C1/ru active
- 1992-03-26 HU HU9201015A patent/HU217590B/hu not_active IP Right Cessation
- 1992-03-26 KR KR1019920004936A patent/KR100221158B1/ko not_active IP Right Cessation
- 1992-03-26 AU AU13826/92A patent/AU649319B2/en not_active Ceased
- 1992-03-27 JP JP07082692A patent/JP3159766B2/ja not_active Expired - Fee Related
- 1992-03-27 MX MX9201374A patent/MX9201374A/es not_active IP Right Cessation
- 1992-03-27 CA CA002064384A patent/CA2064384A1/en not_active Abandoned
- 1992-03-27 BR BR929201089A patent/BR9201089A/pt not_active Application Discontinuation
- 1992-03-27 FI FI921347A patent/FI921347A/fi unknown
- 1992-03-27 YU YU31492A patent/YU31492A/sh unknown
- 1992-03-27 IE IE100192A patent/IE921001A1/en unknown
- 1992-03-27 CN CN92103386A patent/CN1059210C/zh not_active Expired - Fee Related
-
1998
- 1998-12-23 HK HK98115188A patent/HK1013824A1/xx not_active IP Right Cessation
-
1999
- 1999-07-14 GR GR990401845T patent/GR3030760T3/el unknown
- 1999-08-17 CN CN99118107A patent/CN1268352A/zh active Pending
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