CA2148380C - 5-arylindole derivatives - Google Patents
5-arylindole derivatives Download PDFInfo
- Publication number
- CA2148380C CA2148380C CA002148380A CA2148380A CA2148380C CA 2148380 C CA2148380 C CA 2148380C CA 002148380 A CA002148380 A CA 002148380A CA 2148380 A CA2148380 A CA 2148380A CA 2148380 C CA2148380 C CA 2148380C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- ylmethyl
- alkyl
- indol
- aryl
- 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.)
- Expired - Fee Related
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- 150000001875 compounds Chemical class 0.000 claims abstract description 250
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 98
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 63
- 239000001257 hydrogen Substances 0.000 claims abstract description 62
- 150000003839 salts Chemical class 0.000 claims abstract description 62
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 125000003118 aryl group Chemical group 0.000 claims abstract description 30
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 20
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 20
- 206010027599 migraine Diseases 0.000 claims abstract description 20
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
- 208000035475 disorder Diseases 0.000 claims abstract description 11
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 9
- 208000006561 Cluster Headache Diseases 0.000 claims abstract description 8
- 206010019233 Headaches Diseases 0.000 claims abstract description 8
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- 208000030814 Eating disease Diseases 0.000 claims abstract description 6
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- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- 230000002950 deficient Effects 0.000 claims abstract description 4
- 230000000862 serotonergic effect Effects 0.000 claims abstract description 4
- 230000005062 synaptic transmission Effects 0.000 claims abstract description 3
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 62
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- -1 cyano, methoxycarbonyl Chemical group 0.000 claims description 32
- 150000002431 hydrogen Chemical group 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000002460 imidazoles Chemical class 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
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- 125000005518 carboxamido group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 claims description 2
- ZAHXYMFVNNUHCP-UHFFFAOYSA-N Naphazoline nitrate Chemical group O[N+]([O-])=O.C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 ZAHXYMFVNNUHCP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 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 30
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052794 bromium Inorganic materials 0.000 abstract description 5
- 239000011737 fluorine Substances 0.000 abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 abstract description 5
- 239000011630 iodine Substances 0.000 abstract description 5
- 239000000460 chlorine Substances 0.000 abstract description 4
- 229940076279 serotonin Drugs 0.000 abstract description 4
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 abstract description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 3
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- 235000019000 fluorine Nutrition 0.000 abstract 1
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 171
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- 239000002904 solvent Substances 0.000 description 77
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
- 239000000243 solution Substances 0.000 description 67
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
- 239000002585 base Substances 0.000 description 59
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- 239000007787 solid Substances 0.000 description 58
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 57
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
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- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 10
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- 229940054051 antipsychotic indole derivative Drugs 0.000 description 3
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- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A61P25/06—Antimigraine agents
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- A—HUMAN NECESSITIES
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- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- 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
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- 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
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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
- 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
- C07D403/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
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- Saccharide Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002340999A CA2340999C (en) | 1992-11-02 | 1993-10-19 | 5-arylindole derivatives |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97075892A | 1992-11-02 | 1992-11-02 | |
| US07/970,758 | 1992-11-02 | ||
| PCT/US1993/009790 WO1994010171A1 (en) | 1992-11-02 | 1993-10-19 | 5-arylindole derivatives and their use as serotonin (5-ht1) agonists |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002340999A Division CA2340999C (en) | 1992-11-02 | 1993-10-19 | 5-arylindole derivatives |
Publications (2)
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|---|---|
| CA2148380A1 CA2148380A1 (en) | 1994-05-11 |
| CA2148380C true CA2148380C (en) | 2001-08-14 |
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| CA002340999A Expired - Fee Related CA2340999C (en) | 1992-11-02 | 1993-10-19 | 5-arylindole derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002340999A Expired - Fee Related CA2340999C (en) | 1992-11-02 | 1993-10-19 | 5-arylindole derivatives |
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| AT (1) | ATE202102T1 (enExample) |
| AU (1) | AU685066B2 (enExample) |
| BR (1) | BR9307348A (enExample) |
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| GR (1) | GR3036579T3 (enExample) |
| HU (1) | HU222235B1 (enExample) |
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| NZ (1) | NZ257059A (enExample) |
| PL (1) | PL176091B1 (enExample) |
| PT (1) | PT666858E (enExample) |
| RU (1) | RU2134266C1 (enExample) |
| TW (1) | TW251284B (enExample) |
| WO (1) | WO1994010171A1 (enExample) |
| ZA (1) | ZA938137B (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9210400D0 (en) * | 1992-05-15 | 1992-07-01 | Merck Sharp & Dohme | Therapeutic agents |
| AU686654B2 (en) * | 1993-08-31 | 1998-02-12 | Pfizer Inc. | 5-arylindole derivatives |
| CA2183084A1 (en) * | 1994-02-10 | 1995-08-17 | John Eugene Macor | 5-heteroarylindole derivatives |
| GB9420529D0 (en) | 1994-10-12 | 1994-11-30 | Pfizer Ltd | Indoles |
| PL322843A1 (en) * | 1995-03-20 | 1998-02-16 | Lilly Co Eli | 5-substituted 3-91,2,3,6-tetrahydropyridin-4-yl)- and 3-9piperydin-4-4-yl0-1h-indoles nevel 5-htif natagonists |
| AU7261196A (en) * | 1995-10-10 | 1997-04-30 | Eli Lilly And Company | N-{2-substituted-3-(2-aminoethyl)-1h-indol-5-yl}-amides: new 5-ht1f agonists |
| AU746706B2 (en) * | 1997-07-03 | 2002-05-02 | Du Pont Pharmaceuticals Company | Imidazopyrimidines and imidazopyridines for the treatment of neurological disorders |
| US6465484B1 (en) | 1997-09-26 | 2002-10-15 | Merck & Co., Inc. | Angiogenesis inhibitors |
| US7189753B1 (en) | 1997-11-06 | 2007-03-13 | Cady Roger K | Preemptive prophylaxis of migraine |
| AU4850199A (en) * | 1998-06-30 | 2000-01-17 | Eli Lilly And Company | Pyrrolidine and pyrroline derivatives having effects on serotonin related systems |
| US6365589B1 (en) | 1998-07-02 | 2002-04-02 | Bristol-Myers Squibb Pharma Company | Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists |
| GB9819035D0 (en) * | 1998-09-01 | 1998-10-28 | Cerebrus Res Ltd | Chemical compounds VII |
| US5994352A (en) * | 1998-11-13 | 1999-11-30 | Pfizer Inc. | 5-arylindole derivatives |
| PE20030008A1 (es) | 2001-06-19 | 2003-01-22 | Bristol Myers Squibb Co | Inhibidores duales de pde 7 y pde 4 |
| US20040102360A1 (en) * | 2002-10-30 | 2004-05-27 | Barnett Stanley F. | Combination therapy |
| US7399764B2 (en) | 2002-10-30 | 2008-07-15 | Merck & Co., Inc. | Inhibitors of Akt activity |
| US7332508B2 (en) * | 2002-12-18 | 2008-02-19 | Novo Nordisk A/S | Substituted homopiperidine, piperidine or pyrrolidine derivatives |
| AU2004233827B2 (en) | 2003-04-24 | 2009-05-28 | Merck Sharp & Dohme Corp. | Inhibitors of Akt activity |
| DE10337184A1 (de) | 2003-08-13 | 2005-03-10 | Gruenenthal Gmbh | Substituierte 3-Pyrrolidin-Indol-Derivate |
| EP1658289B1 (en) * | 2003-08-21 | 2009-03-18 | OSI Pharmaceuticals, Inc. | 3-substituted imidazopyridine-derivatives as c-kit inhibitors |
| US7442709B2 (en) * | 2003-08-21 | 2008-10-28 | Osi Pharmaceuticals, Inc. | N3-substituted imidazopyridine c-Kit inhibitors |
| US8871782B2 (en) | 2003-10-03 | 2014-10-28 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| AU2004293078B2 (en) | 2003-11-25 | 2012-01-19 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| DE102004014304A1 (de) | 2004-03-22 | 2005-10-06 | Grünenthal GmbH | Substituierte 1,4,8- Triazaspiro[4,5]decan-2-on-Verbindungen |
| WO2006084251A2 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
| CN101405285B (zh) * | 2006-03-22 | 2012-10-10 | 詹森药业有限公司 | 作为mdm2和p53间相互作用的抑制剂的环状-烷基胺衍生物 |
| WO2014078568A1 (en) | 2012-11-14 | 2014-05-22 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| CN105142623A (zh) | 2013-03-15 | 2015-12-09 | 艾吉因生物股份有限公司 | 用于改善认知功能的方法和组合物 |
| EP2968237A4 (en) | 2013-03-15 | 2016-08-31 | Univ Johns Hopkins | METHOD AND COMPOSITIONS FOR IMPROVING COGNITIVE FUNCTION |
| AU2016256413B2 (en) | 2015-04-29 | 2020-10-08 | Janssen Pharmaceutica Nv | Indolone compounds and their use as AMPA receptor modulators |
| MX373652B (es) | 2015-04-29 | 2020-04-02 | Janssen Pharmaceutica Nv | Imidazopirazinas y pirazolopirimidinas y su uso como moduladores del receptor de ampa. |
| MX378389B (es) | 2015-04-29 | 2025-03-10 | Janssen Pharmaceutica Nv | Compuestos de bencimidazolona y benzotiazolona y su uso como moduladores del receptor ampa. |
| WO2016176460A1 (en) * | 2015-04-29 | 2016-11-03 | Janssen Pharmaceutica Nv | Azabenzimidazoles and their use as ampa receptor modulators |
| CN107810002B (zh) | 2015-05-22 | 2021-01-05 | 艾吉因生物股份有限公司 | 左乙拉西坦的延时释放药物组合物 |
| WO2017076842A1 (en) | 2015-11-06 | 2017-05-11 | F. Hoffmann-La Roche Ag | Indolin-2-one derivatives |
| CN108349944B (zh) | 2015-11-06 | 2021-03-30 | 豪夫迈·罗氏有限公司 | 二氢吲哚-2-酮衍生物 |
| WO2017076932A1 (en) | 2015-11-06 | 2017-05-11 | F. Hoffmann-La Roche Ag | Indolin-2-one derivatives useful in the treatment of cns diseases |
| WO2017076931A1 (en) | 2015-11-06 | 2017-05-11 | F. Hoffmann-La Roche Ag | Indolin-2-one derivatives for use in the treatment of cns and related disorders |
| CN111822047B (zh) * | 2020-07-17 | 2022-05-27 | 曲阜师范大学 | 一种磁性介孔聚合离子液体负载催化合成吲哚类衍生物的方法 |
| WO2025104490A1 (en) * | 2023-11-14 | 2025-05-22 | Mindset Pharma Inc. | Indole derivatives as serotonergic agents useful for the treatment of disorders related thereto |
| WO2025104491A1 (en) * | 2023-11-14 | 2025-05-22 | Mindset Pharma Inc. | Indole derivatives as serotonergic agents useful for the treatment of disorders related thereto |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA795239B (en) * | 1978-10-12 | 1980-11-26 | Glaxo Group Ltd | Heterocyclic compounds |
| ZA815541B (en) * | 1980-08-12 | 1983-03-30 | Glaxo Group Ltd | Heterocyclic compounds |
| US4983622A (en) * | 1984-02-06 | 1991-01-08 | Eli Lilly And Company | 6-substituted-4-dialkylaminotetrahydrobenz(c,d)indoles |
| GB8600397D0 (en) * | 1986-01-08 | 1986-02-12 | Glaxo Group Ltd | Chemical compounds |
| GB8719167D0 (en) * | 1987-08-13 | 1987-09-23 | Glaxo Group Ltd | Chemical compounds |
| GB8724912D0 (en) * | 1987-10-23 | 1987-11-25 | Wellcome Found | Indole derivatives |
| GB8819024D0 (en) * | 1988-08-10 | 1988-09-14 | Glaxo Group Ltd | Chemical compounds |
| IL96891A0 (en) * | 1990-01-17 | 1992-03-29 | Merck Sharp & Dohme | Indole-substituted five-membered heteroaromatic compounds,their preparation and pharmaceutical compositions containing them |
| US5340838A (en) * | 1990-05-04 | 1994-08-23 | Eli Lilly And Company | Method of inhibiting gastric acid secretion with 2-phenylcyclopropylamines |
| CA2042295A1 (fr) * | 1990-05-15 | 1991-11-16 | Jacques Chauveau | Derives de mediateurs endogenes, leurs sels, procede de preparation, applications, et compositions les renfermant |
| ATE204275T1 (de) * | 1990-06-07 | 2001-09-15 | Astrazeneca Ab | Indolderivate als 5-ht1-like agonisten |
| DK158590D0 (da) * | 1990-07-02 | 1990-07-02 | Lundbeck & Co As H | Indolderivater |
| BR9106978A (pt) * | 1990-10-15 | 1993-09-28 | Pfizer | Derivados de indol |
| SK278998B6 (sk) * | 1991-02-01 | 1998-05-06 | Merck Sharp & Dohme Limited | Deriváty imidazolu, triazolu a tetrazolu, spôsob i |
| FR2672602B1 (fr) * | 1991-02-12 | 1993-06-04 | Centre Nat Rech Scient | Composes derives des beta-carbolines ligands du recepteur des benzodiazepines ayant un effet agoniste inverse et antagoniste vis-a-vis des benzodiazepines et medicaments les contenant. |
| US5229401A (en) * | 1991-09-23 | 1993-07-20 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted pyridinylamino benzo[b]thiophene compounds |
| US5187159A (en) * | 1991-10-07 | 1993-02-16 | Merck & Co., Inc. | Angiotensin II antagonists incorporating a substituted 1,3-benzodioxole or 1,3-benzodithiole |
| GB9210400D0 (en) * | 1992-05-15 | 1992-07-01 | Merck Sharp & Dohme | Therapeutic agents |
| US5378846A (en) * | 1993-06-11 | 1995-01-03 | Russian-American Institute For New Drug Development | 1,2,3,4-tetrahydropyrrolo-[1,2-a]-pyrazine derivatives |
-
1993
- 1993-10-16 TW TW082108604A patent/TW251284B/zh active
- 1993-10-19 PT PT93923389T patent/PT666858E/pt unknown
- 1993-10-19 NZ NZ257059A patent/NZ257059A/en unknown
- 1993-10-19 KR KR1019950701729A patent/KR0163371B1/ko not_active Expired - Fee Related
- 1993-10-19 CA CA002148380A patent/CA2148380C/en not_active Expired - Fee Related
- 1993-10-19 DE DE69330351T patent/DE69330351T2/de not_active Expired - Fee Related
- 1993-10-19 CA CA002340999A patent/CA2340999C/en not_active Expired - Fee Related
- 1993-10-19 BR BR9307348A patent/BR9307348A/pt not_active Application Discontinuation
- 1993-10-19 EP EP93923389A patent/EP0666858B1/en not_active Expired - Lifetime
- 1993-10-19 AU AU53294/94A patent/AU685066B2/en not_active Ceased
- 1993-10-19 ES ES93923389T patent/ES2157224T3/es not_active Expired - Lifetime
- 1993-10-19 CZ CZ951108A patent/CZ283001B6/cs not_active IP Right Cessation
- 1993-10-19 US US08/424,357 patent/US5886008A/en not_active Expired - Fee Related
- 1993-10-19 JP JP6511101A patent/JP2788551B2/ja not_active Expired - Lifetime
- 1993-10-19 WO PCT/US1993/009790 patent/WO1994010171A1/en not_active Ceased
- 1993-10-19 EP EP00124422A patent/EP1094064A1/en not_active Withdrawn
- 1993-10-19 AT AT93923389T patent/ATE202102T1/de not_active IP Right Cessation
- 1993-10-19 RU RU95109927/04A patent/RU2134266C1/ru not_active IP Right Cessation
- 1993-10-19 DK DK93923389T patent/DK0666858T3/da active
- 1993-10-25 IL IL10738693A patent/IL107386A/en not_active IP Right Cessation
- 1993-11-01 ZA ZA938137A patent/ZA938137B/xx unknown
- 1993-11-01 MY MYPI93002280A patent/MY109696A/en unknown
- 1993-11-01 FI FI934825A patent/FI111257B/fi not_active IP Right Cessation
- 1993-11-01 CN CN93120716A patent/CN1051313C/zh not_active Expired - Fee Related
- 1993-11-02 EG EG69793A patent/EG20396A/xx active
- 1993-11-02 HU HU9303118A patent/HU222235B1/hu not_active IP Right Cessation
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1995
- 1995-04-28 NO NO951633A patent/NO309652B1/no not_active IP Right Cessation
- 1995-05-01 PL PL93308669A patent/PL176091B1/pl unknown
-
2000
- 2000-11-15 FI FI20002505A patent/FI20002505A7/fi unknown
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2001
- 2001-09-11 GR GR20010401436T patent/GR3036579T3/el not_active IP Right Cessation
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| MKLA | Lapsed |