JP2004505078A5 - - Google Patents
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- Publication number
- JP2004505078A5 JP2004505078A5 JP2002515887A JP2002515887A JP2004505078A5 JP 2004505078 A5 JP2004505078 A5 JP 2004505078A5 JP 2002515887 A JP2002515887 A JP 2002515887A JP 2002515887 A JP2002515887 A JP 2002515887A JP 2004505078 A5 JP2004505078 A5 JP 2004505078A5
- Authority
- JP
- Japan
- Prior art keywords
- heteroalkyl
- hydrogen
- compound according
- alkyl
- disease
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 27
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 125000004404 heteroalkyl group Chemical group 0.000 claims 15
- -1 cyano, nitro, amino Chemical group 0.000 claims 13
- 201000010099 disease Diseases 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 208000006673 asthma Diseases 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 7
- 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 claims 6
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 claims 6
- 239000003112 inhibitor Substances 0.000 claims 6
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims 5
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims 5
- 206010020751 Hypersensitivity Diseases 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 208000026935 allergic disease Diseases 0.000 claims 5
- 230000007815 allergy Effects 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004442 acylamino group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 206010003210 Arteriosclerosis Diseases 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 3
- 208000020925 Bipolar disease Diseases 0.000 claims 3
- 206010061598 Immunodeficiency Diseases 0.000 claims 3
- 208000029462 Immunodeficiency disease Diseases 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 230000007813 immunodeficiency Effects 0.000 claims 3
- 208000028867 ischemia Diseases 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 230000009529 traumatic brain injury Effects 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- MZUZXNZGBBUAIM-UHFFFAOYSA-N 3-(1h-indol-3-yl)-4-phenylfuran-2,5-dione Chemical compound C=1NC2=CC=CC=C2C=1C=1C(=O)OC(=O)C=1C1=CC=CC=C1 MZUZXNZGBBUAIM-UHFFFAOYSA-N 0.000 claims 1
- 102000004127 Cytokines Human genes 0.000 claims 1
- 108090000695 Cytokines Proteins 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22105800P | 2000-07-27 | 2000-07-27 | |
| PCT/EP2001/008293 WO2002010158A2 (en) | 2000-07-27 | 2001-07-18 | 3-indolyl-4-phenyl-1h-pyrrole-2,5-dione derivatives as inhibitors of glycogen synthase kinase-3beta |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004505078A JP2004505078A (ja) | 2004-02-19 |
| JP2004505078A5 true JP2004505078A5 (https=) | 2005-03-03 |
| JP3984157B2 JP3984157B2 (ja) | 2007-10-03 |
Family
ID=22826151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002515887A Expired - Lifetime JP3984157B2 (ja) | 2000-07-27 | 2001-07-18 | グリコーゲンシンターゼキナーゼ−３ベータのインヒビターとしての３−インドリル−４−フェニル−１ｈ−ピロール−２，５−ジオン誘導体 |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US6479490B2 (https=) |
| EP (1) | EP1307447B1 (https=) |
| JP (1) | JP3984157B2 (https=) |
| KR (1) | KR20030017655A (https=) |
| CN (1) | CN1185229C (https=) |
| AR (1) | AR033989A1 (https=) |
| AT (1) | ATE284885T1 (https=) |
| AU (1) | AU2001293702A1 (https=) |
| BR (1) | BR0112965A (https=) |
| CA (1) | CA2417277A1 (https=) |
| CZ (1) | CZ2003555A3 (https=) |
| DE (1) | DE60107857T2 (https=) |
| EC (1) | ECSP034452A (https=) |
| ES (1) | ES2233691T3 (https=) |
| GT (1) | GT200100151A (https=) |
| HR (1) | HRP20030030A2 (https=) |
| HU (1) | HUP0301431A2 (https=) |
| IL (1) | IL153851A0 (https=) |
| JO (1) | JO2293B1 (https=) |
| MA (1) | MA26936A1 (https=) |
| MX (1) | MXPA03000695A (https=) |
| NO (1) | NO20030328D0 (https=) |
| NZ (1) | NZ523462A (https=) |
| PA (1) | PA8523001A1 (https=) |
| PE (1) | PE20020338A1 (https=) |
| PL (1) | PL366701A1 (https=) |
| RU (1) | RU2003104796A (https=) |
| UY (1) | UY26857A1 (https=) |
| WO (1) | WO2002010158A2 (https=) |
| YU (1) | YU4403A (https=) |
| ZA (1) | ZA200300216B (https=) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001013916A1 (en) * | 1999-08-20 | 2001-03-01 | Sagami Chemical Research Center | Drugs inhibiting cell death |
| CA2424246A1 (en) * | 2000-10-02 | 2002-04-11 | Shianlen Cahoon | Methods and compositions for the treatment of inflammatory diseases |
| EP2070921A1 (en) * | 2000-11-07 | 2009-06-17 | Novartis Ag | Indolylmaleimide derivatives as protein kinase c inhibitors |
| US6645970B2 (en) | 2000-11-07 | 2003-11-11 | Novartis Ag | Indolylmaleimide derivatives |
| MXPA04002438A (es) * | 2001-09-24 | 2004-06-29 | Bayer Pharmaceuticals Corp | Preparacion y uso de derivados de pirroll para el tratamiento de la obesidad. |
| ES2316756T3 (es) * | 2002-01-10 | 2009-04-16 | F. Hoffmann-La Roche Ag | Uso de un inhibidor de gsk-3beta en la fabricacion de un medicamento para incrementar la formacion osea. |
| WO2003076442A1 (en) | 2002-03-05 | 2003-09-18 | Eli Lilly And Company | Purine derivatives as kinase inhibitors |
| ES2289274T3 (es) * | 2002-03-08 | 2008-02-01 | Eli Lilly And Company | Derivados de pirrol-2,5-diona y su uso como inhibidores de gsk-3. |
| SE0200979D0 (sv) * | 2002-03-28 | 2002-03-28 | Astrazeneca Ab | New compounds |
| SE0302546D0 (sv) | 2003-09-24 | 2003-09-24 | Astrazeneca Ab | New compounds |
| TW200918046A (en) * | 2002-04-03 | 2009-05-01 | Novartis Ag | Indolylmaleimide derivatives |
| JP2005531607A (ja) | 2002-06-05 | 2005-10-20 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | キナーゼ阻害剤として置換ピロリン |
| EP1513830A1 (en) | 2002-06-05 | 2005-03-16 | Janssen Pharmaceutica N.V. | Bisindolyl-maleimid derivatives as kinase inhibitors |
| GB0303319D0 (en) | 2003-02-13 | 2003-03-19 | Novartis Ag | Organic compounds |
| US7250444B2 (en) * | 2003-08-11 | 2007-07-31 | Pfizer Inc. | Pyrrole-based HMG-CoA reductase inhibitors |
| US7109436B2 (en) * | 2003-08-29 | 2006-09-19 | General Electric Company | Laser shock peening target |
| TWI339206B (en) * | 2003-09-04 | 2011-03-21 | Vertex Pharma | Compositions useful as inhibitors of protein kinases |
| EP1682103A1 (en) * | 2003-10-27 | 2006-07-26 | Novartis AG | Indolyl-pyrroledione derivatives for the treatment of neurological and vascular disorders related to beta-amyloid generation and/or aggregation |
| US20100152044A1 (en) * | 2004-05-12 | 2010-06-17 | Bayer Cropscience Gmbh | Plant growth regulation |
| WO2006061212A1 (en) | 2004-12-08 | 2006-06-15 | Johannes Gutenberg-Universität Mainz | 3-(indolyl)-4-arylmaleimide derivatives and their use as angiogenesis inhibitors |
| JP4747364B2 (ja) * | 2005-04-04 | 2011-08-17 | 独立行政法人産業技術総合研究所 | 紫外線皮膚炎抑止剤およびアトピー性皮膚炎抑止剤 |
| US20080207594A1 (en) | 2005-05-04 | 2008-08-28 | Davelogen Aktiengesellschaft | Use of Gsk-3 Inhibitors for Preventing and Treating Pancreatic Autoimmune Disorders |
| EP2275095A3 (en) | 2005-08-26 | 2011-08-17 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| AU2006308889A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | GABA receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| EP2382975A3 (en) | 2006-05-09 | 2012-02-29 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| ES2446269T3 (es) | 2006-12-19 | 2014-03-06 | The Board Of Trustees Of The University Of Illinois | 3-Benzofuranil-4-indolil-maleimidas como potentes inhibidores de GSK-3 para trastornos neurodegenerativos |
| WO2008080824A1 (en) * | 2006-12-29 | 2008-07-10 | F. Hoffmann-La Roche Ag | Aromatic sulfonated ketals |
| BRPI0914772A2 (pt) * | 2008-06-25 | 2015-10-20 | Envivo Pharmaceuticals Inc | compostos heterocíclicos 1,2-dissubstituídos |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| EP2343291A1 (en) | 2009-12-18 | 2011-07-13 | Johannes Gutenberg-Universität Mainz | 3-(Indolyl)- or 3-(Azaindolyl)-4-arylmaleimide compounds and their use in tumor treatment |
| KR101851518B1 (ko) * | 2010-09-08 | 2018-04-23 | 스미또모 가가꾸 가부시끼가이샤 | 피리다지논 화합물 및 그 중간체의 제조 방법 |
| EP2474541A1 (en) | 2010-12-23 | 2012-07-11 | Johannes- Gutenberg-Universität Mainz | Conjugated 3-(indolyl)- and 3-(azaindolyl)-4-arylmaleimide compounds and their use in tumor treatment |
| KR20130034672A (ko) * | 2011-09-28 | 2013-04-08 | 김동식 | 보텍스타입 열교환기 |
| KR101440724B1 (ko) * | 2013-03-29 | 2014-09-18 | 중앙대학교 산학협력단 | 글리코겐 신타아제 키나아제-3베타 억제물질을 유효성분으로 포함하는 난소과립세포종양의 예방 또는 치료용 약학적 조성물 및 건강기능성식품 조성물 |
| CA2945263A1 (en) | 2014-04-09 | 2015-10-15 | Christopher Rudd | Use of gsk-3 inhibitors or activators which modulate pd-1 or t-bet expression to modulate t cell immunity |
| TWI677489B (zh) | 2014-06-20 | 2019-11-21 | 美商基利科學股份有限公司 | 多環型胺甲醯基吡啶酮化合物之合成 |
| EP3187495A1 (en) | 2015-12-30 | 2017-07-05 | Johannes Gutenberg-Universität Mainz | 3-(5-fluoroindolyl)-4-arylmaleimide compounds and their use in tumor treatment |
| WO2018132636A1 (en) * | 2017-01-12 | 2018-07-19 | The Research Foundation For The State University Of New York | [18f]maleimide-based glycogen synthase kinase-3beta ligands for positron emission tomography imaging and radiosynthesis method |
| CN112538458B (zh) | 2020-11-26 | 2025-10-31 | 北京孟眸生物科技有限公司 | 用于重编程细胞的方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ227850A (en) * | 1988-02-10 | 1991-11-26 | Hoffmann La Roche | Indole substituted pyrrole derivatives; preparatory process and medicaments for use against inflammatory immunological, bronchopulmonary or vascular disorders |
| MC2096A1 (fr) | 1989-02-23 | 1991-02-15 | Hoffmann La Roche | Pyrroles substitues |
| GB8904161D0 (en) | 1989-02-23 | 1989-04-05 | Hoffmann La Roche | Substituted pyrroles |
| GB9123396D0 (en) | 1991-11-04 | 1991-12-18 | Hoffmann La Roche | A process for the manufacture of substituted maleimides |
| CA2116460A1 (en) | 1993-03-02 | 1994-09-03 | Mitsubishi Chemical Corporation | Preventive or therapeutic agents for alzheimer's disease, a screening method of alzheimer's disease and tau-protein kinase i originated from human being |
| AU678435B2 (en) | 1993-05-10 | 1997-05-29 | F. Hoffmann-La Roche Ag | Substituted pyrroles |
| US5721230A (en) | 1993-05-10 | 1998-02-24 | Hoffmann-La Roche Inc. | Substituted pyrroles |
| JP2000502097A (ja) | 1995-12-20 | 2000-02-22 | メディカル、リサーチ、カウンシル | タンパク質合成の制御、および作用薬のスクリーニング法 |
| WO1997041854A1 (en) | 1996-05-07 | 1997-11-13 | The Trustees Of The University Of Pennsylvania | Inhibitors of glycogen synthase kinase-3 and methods for identifying and using the same |
| SE9603285D0 (sv) | 1996-09-10 | 1996-09-10 | Astra Ab | New compounds |
| AU6111699A (en) * | 1998-10-08 | 2000-05-01 | Smithkline Beecham Plc | Novel method and compounds |
| GB9828640D0 (en) * | 1998-12-23 | 1999-02-17 | Smithkline Beecham Plc | Novel method and compounds |
-
2001
- 2001-07-18 CA CA002417277A patent/CA2417277A1/en not_active Abandoned
- 2001-07-18 EP EP01974083A patent/EP1307447B1/en not_active Expired - Lifetime
- 2001-07-18 CZ CZ2003555A patent/CZ2003555A3/cs unknown
- 2001-07-18 WO PCT/EP2001/008293 patent/WO2002010158A2/en not_active Ceased
- 2001-07-18 PL PL01366701A patent/PL366701A1/xx not_active Application Discontinuation
- 2001-07-18 HR HR20030030A patent/HRP20030030A2/hr not_active Application Discontinuation
- 2001-07-18 NZ NZ523462A patent/NZ523462A/en unknown
- 2001-07-18 BR BR0112965-1A patent/BR0112965A/pt not_active IP Right Cessation
- 2001-07-18 MX MXPA03000695A patent/MXPA03000695A/es unknown
- 2001-07-18 DE DE60107857T patent/DE60107857T2/de not_active Expired - Fee Related
- 2001-07-18 CN CNB018134068A patent/CN1185229C/zh not_active Expired - Fee Related
- 2001-07-18 JP JP2002515887A patent/JP3984157B2/ja not_active Expired - Lifetime
- 2001-07-18 ES ES01974083T patent/ES2233691T3/es not_active Expired - Lifetime
- 2001-07-18 AU AU2001293702A patent/AU2001293702A1/en not_active Abandoned
- 2001-07-18 KR KR10-2003-7001111A patent/KR20030017655A/ko not_active Ceased
- 2001-07-18 YU YU4403A patent/YU4403A/sh unknown
- 2001-07-18 RU RU2003104796/04A patent/RU2003104796A/ru not_active Application Discontinuation
- 2001-07-18 AT AT01974083T patent/ATE284885T1/de not_active IP Right Cessation
- 2001-07-18 IL IL15385101A patent/IL153851A0/xx unknown
- 2001-07-18 HU HU0301431A patent/HUP0301431A2/hu unknown
- 2001-07-23 PE PE2001000742A patent/PE20020338A1/es not_active Application Discontinuation
- 2001-07-24 PA PA20018523001A patent/PA8523001A1/es unknown
- 2001-07-24 JO JO2001126A patent/JO2293B1/en active
- 2001-07-25 AR ARP010103541A patent/AR033989A1/es not_active Application Discontinuation
- 2001-07-26 UY UY26857A patent/UY26857A1/es not_active Application Discontinuation
- 2001-07-26 GT GT200100151A patent/GT200100151A/es unknown
- 2001-07-27 US US09/916,706 patent/US6479490B2/en not_active Expired - Fee Related
-
2002
- 2002-05-06 US US10/139,410 patent/US20020188018A1/en not_active Abandoned
-
2003
- 2003-01-08 ZA ZA200300216A patent/ZA200300216B/en unknown
- 2003-01-22 NO NO20030328A patent/NO20030328D0/no not_active Application Discontinuation
- 2003-01-24 EC EC2003004452A patent/ECSP034452A/es unknown
- 2003-01-24 MA MA27013A patent/MA26936A1/fr unknown
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