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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- 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
-
- 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)
- Organic Chemistry (AREA)
- 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)
- Plural Heterocyclic 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 |
Family
ID=25517470
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| Application Number | Title | Priority Date | Filing Date |
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| CA002148380A Expired - Fee Related CA2148380C (en) | 1992-11-02 | 1993-10-19 | 5-arylindole derivatives |
| 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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| JP (1) | JP2788551B2 (enExample) |
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| CN (1) | CN1051313C (enExample) |
| AT (1) | ATE202102T1 (enExample) |
| AU (1) | AU685066B2 (enExample) |
| BR (1) | BR9307348A (enExample) |
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| ES (1) | ES2157224T3 (enExample) |
| FI (2) | FI111257B (enExample) |
| GR (1) | GR3036579T3 (enExample) |
| HU (1) | HU222235B1 (enExample) |
| IL (1) | IL107386A (enExample) |
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| NO (1) | NO309652B1 (enExample) |
| 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 |
| CN1129933A (zh) * | 1993-08-31 | 1996-08-28 | 辉瑞大药厂 | 5-芳基吲哚衍生物 |
| JP2829788B2 (ja) * | 1994-02-10 | 1998-12-02 | ファイザー インク． | ベンゾジアゼピン受容体部位アゴニスト及びアンタゴニストとしての５−ヘテロアリールインドール誘導体 |
| GB9420529D0 (en) | 1994-10-12 | 1994-11-30 | Pfizer Ltd | Indoles |
| CN1184425A (zh) * | 1995-03-20 | 1998-06-10 | 伊莱利利公司 | 5－取代－3－(1,2,3,6－四氢吡啶－4－基)－和3－(哌啶－4－基)－1h－吲哚:新型5－ht1f激动剂 |
| JPH11513666A (ja) * | 1995-10-10 | 1999-11-24 | イーライ・リリー・アンド・カンパニー | Ｎ−［２−置換−３−（２−アミノエチル）−１ｈ−インドール−５−イル］−アミド：新規５−ｈｔ▲下１ｆ▼作動剤 |
| CN1268137A (zh) * | 1997-07-03 | 2000-09-27 | 杜邦药品公司 | 治疗神经失调的咪唑并嘧啶和咪唑并吡啶 |
| 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 |
| EP1100501A4 (en) * | 1998-06-30 | 2002-12-04 | Lilly Co Eli | PYRROLIDINE AND PYRROLIDINE DERIVATIVES INFLUENTING THE SYSTEMS ASSOCIATED WITH SEROTONIN |
| 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 |
| CA2501365C (en) | 2002-10-30 | 2011-05-31 | Merck & Co., Inc. | Inhibitors of akt activity |
| US20040102360A1 (en) * | 2002-10-30 | 2004-05-27 | Barnett Stanley F. | Combination therapy |
| US7332508B2 (en) | 2002-12-18 | 2008-02-19 | Novo Nordisk A/S | Substituted homopiperidine, piperidine or pyrrolidine derivatives |
| CN1809351A (zh) | 2003-04-24 | 2006-07-26 | 麦克公司 | Akt活性抑制剂 |
| DE10337184A1 (de) | 2003-08-13 | 2005-03-10 | Gruenenthal Gmbh | Substituierte 3-Pyrrolidin-Indol-Derivate |
| US7442709B2 (en) * | 2003-08-21 | 2008-10-28 | Osi Pharmaceuticals, Inc. | N3-substituted imidazopyridine c-Kit inhibitors |
| AU2004268950A1 (en) * | 2003-08-21 | 2005-03-10 | Osi Pharmaceuticals, Inc. | N3-substituted imidazopyridine-derivatives as c-kit inhibitors |
| AR046046A1 (es) | 2003-10-03 | 2005-11-23 | 3M Innovative Properties Co | Imidazoquinolinas alcoxi sustituidas. composiciones farmaceuticas. |
| MXPA06005910A (es) | 2003-11-25 | 2006-08-23 | 3M Innovative Properties Co | Sistemas de anillo imidazo sustituido y metodos. |
| DE102004014304A1 (de) * | 2004-03-22 | 2005-10-06 | Grünenthal GmbH | Substituierte 1,4,8- Triazaspiro[4,5]decan-2-on-Verbindungen |
| CA2597092A1 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
| ES2346157T3 (es) * | 2006-03-22 | 2010-10-11 | Janssen Pharmaceutica N.V. | Derivados de alquilaminas ciclicas como inhibidores de la interaccion entre mdm2 y p53. |
| JP6440625B2 (ja) | 2012-11-14 | 2018-12-19 | ザ・ジョンズ・ホプキンス・ユニバーシティー | 精神分裂病を処置するための方法および組成物 |
| EP2968237A4 (en) | 2013-03-15 | 2016-08-31 | Univ Johns Hopkins | METHOD AND COMPOSITIONS FOR IMPROVING COGNITIVE FUNCTION |
| EP2968220B1 (en) | 2013-03-15 | 2021-05-05 | Agenebio, Inc. | Methods and compositions for improving cognitive function |
| BR112017023038A2 (pt) | 2015-04-29 | 2018-07-03 | Janssen Pharmaceutica Nv | imidazopirazinas e pirazolopirimidinas e seu uso como moduladores do receptor ampa |
| CA2984290C (en) | 2015-04-29 | 2022-03-01 | Janssen Pharmaceutica Nv | Benzimidazolone and benzothiazolone compounds and their use as ampa receptor modulators |
| KR20170140382A (ko) * | 2015-04-29 | 2017-12-20 | 얀센 파마슈티카 엔.브이. | 아자벤즈이미다졸 및 ampa 수용체 조절제로서의 이의 용도 |
| CN107750250B (zh) | 2015-04-29 | 2021-09-07 | 詹森药业有限公司 | 吲哚酮化合物及其作为ampa受体调节剂的用途 |
| MX384391B (es) | 2015-05-22 | 2025-03-14 | Agenebio Inc | Composiciones farmacéuticas de levetiracetam de liberación extendida. |
| JP6839184B2 (ja) | 2015-11-06 | 2021-03-03 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | インドリン−２−オン誘導体 |
| UA122589C2 (uk) | 2015-11-06 | 2020-12-10 | Ф. Хоффманн-Ля Рош Аг | Похідні індолін-2-ону |
| CN108137555B (zh) | 2015-11-06 | 2021-02-19 | 豪夫迈·罗氏有限公司 | 可用于治疗cns疾病的二氢吲哚-2-酮衍生物 |
| 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 |
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| 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 |
| SI9111010B (sl) * | 1990-06-07 | 2005-02-28 | Astrazeneca Ab | 3,5-disubstituirani indolni derivati kot "5-HT1-podobni" receptorski agonisti |
| DK158590D0 (da) * | 1990-07-02 | 1990-07-02 | Lundbeck & Co As H | Indolderivater |
| PL168919B1 (pl) * | 1990-10-15 | 1996-05-31 | Pfizer | Sposób wytwarzania nowych pochodnych indolu PL PL PL PL |
| 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 |
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1993
- 1993-10-16 TW TW082108604A patent/TW251284B/zh active
- 1993-10-19 CA CA002148380A patent/CA2148380C/en not_active Expired - Fee Related
- 1993-10-19 ES ES93923389T patent/ES2157224T3/es not_active Expired - Lifetime
- 1993-10-19 KR KR1019950701729A patent/KR0163371B1/ko not_active Expired - Fee Related
- 1993-10-19 DE DE69330351T patent/DE69330351T2/de not_active Expired - Fee Related
- 1993-10-19 EP EP93923389A patent/EP0666858B1/en not_active Expired - Lifetime
- 1993-10-19 JP JP6511101A patent/JP2788551B2/ja not_active Expired - Lifetime
- 1993-10-19 EP EP00124422A patent/EP1094064A1/en not_active Withdrawn
- 1993-10-19 DK DK93923389T patent/DK0666858T3/da active
- 1993-10-19 RU RU95109927/04A patent/RU2134266C1/ru not_active IP Right Cessation
- 1993-10-19 AU AU53294/94A patent/AU685066B2/en not_active Ceased
- 1993-10-19 US US08/424,357 patent/US5886008A/en not_active Expired - Fee Related
- 1993-10-19 BR BR9307348A patent/BR9307348A/pt not_active Application Discontinuation
- 1993-10-19 AT AT93923389T patent/ATE202102T1/de not_active IP Right Cessation
- 1993-10-19 CA CA002340999A patent/CA2340999C/en not_active Expired - Fee Related
- 1993-10-19 NZ NZ257059A patent/NZ257059A/en unknown
- 1993-10-19 PT PT93923389T patent/PT666858E/pt unknown
- 1993-10-19 CZ CZ951108A patent/CZ283001B6/cs not_active IP Right Cessation
- 1993-10-19 WO PCT/US1993/009790 patent/WO1994010171A1/en not_active Ceased
- 1993-10-25 IL IL10738693A patent/IL107386A/en not_active IP Right Cessation
- 1993-11-01 FI FI934825A patent/FI111257B/fi not_active IP Right Cessation
- 1993-11-01 MY MYPI93002280A patent/MY109696A/en unknown
- 1993-11-01 CN CN93120716A patent/CN1051313C/zh not_active Expired - Fee Related
- 1993-11-01 ZA ZA938137A patent/ZA938137B/xx unknown
- 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
-
2001
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