JP2011506494A - 癌の治療に有用なキナーゼ阻害剤としてのインダゾリル、ベンズイミダゾリル、ベンゾトリアゾリル置換インドルモン誘導体 - Google Patents
癌の治療に有用なキナーゼ阻害剤としてのインダゾリル、ベンズイミダゾリル、ベンゾトリアゾリル置換インドルモン誘導体 Download PDFInfo
- Publication number
- JP2011506494A JP2011506494A JP2010538297A JP2010538297A JP2011506494A JP 2011506494 A JP2011506494 A JP 2011506494A JP 2010538297 A JP2010538297 A JP 2010538297A JP 2010538297 A JP2010538297 A JP 2010538297A JP 2011506494 A JP2011506494 A JP 2011506494A
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- Prior art keywords
- alkyl
- group
- optionally substituted
- phenyl
- independently
- 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.)
- Withdrawn
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- 0 Cc1cc(**2(*3)CCCCCCCC2)c3cc1 Chemical compound Cc1cc(**2(*3)CCCCCCCC2)c3cc1 0.000 description 7
- JSWBCLYBECAWJB-MHWRWJLKSA-N C/C(/c1cc([nH]nc2)c2cc1)=C(/c(cccc1)c1N1)\C1=O Chemical compound C/C(/c1cc([nH]nc2)c2cc1)=C(/c(cccc1)c1N1)\C1=O JSWBCLYBECAWJB-MHWRWJLKSA-N 0.000 description 1
- RKDCVQPINOVEQH-AADYKHLVSA-N CN(CC1)CCN1C(/C=C/c1n[nH]c2cc(/C=C(\c(cc(cc3)OC)c3N3)/C3=O)ccc12)=O Chemical compound CN(CC1)CCN1C(/C=C/c1n[nH]c2cc(/C=C(\c(cc(cc3)OC)c3N3)/C3=O)ccc12)=O RKDCVQPINOVEQH-AADYKHLVSA-N 0.000 description 1
- QVTKKPHAYXSKBL-LLFXVZEOSA-N COc(cc1)cc(/C2=C\c3ccc(c(/C=C/c(cc4)ccc4C(O)=O)n[nH]4)c4c3)c1NC2=O Chemical compound COc(cc1)cc(/C2=C\c3ccc(c(/C=C/c(cc4)ccc4C(O)=O)n[nH]4)c4c3)c1NC2=O QVTKKPHAYXSKBL-LLFXVZEOSA-N 0.000 description 1
- DCUNRLLJHAWKRZ-UHFFFAOYSA-N Cc(cc1)cc2c1[nH]nc2 Chemical compound Cc(cc1)cc2c1[nH]nc2 DCUNRLLJHAWKRZ-UHFFFAOYSA-N 0.000 description 1
- APYBEUHFLLBSDC-GEALHNJRSA-N Cc1c(/C=C/c2n[nH]c3cc(/C=C(\c(cccc4)c4N4)/C4=O)ccc23)[s]cn1 Chemical compound Cc1c(/C=C/c2n[nH]c3cc(/C=C(\c(cccc4)c4N4)/C4=O)ccc23)[s]cn1 APYBEUHFLLBSDC-GEALHNJRSA-N 0.000 description 1
- VNFLYLYPTVUKSB-NHSDSWEZSA-N Nc(cc1/C2=C\c3ccc(c(/C=C/c4ccncc4)n[nH]4)c4c3)ccc1NC2=O Chemical compound Nc(cc1/C2=C\c3ccc(c(/C=C/c4ccncc4)n[nH]4)c4c3)ccc1NC2=O VNFLYLYPTVUKSB-NHSDSWEZSA-N 0.000 description 1
- BPGUPPRJBLLMOX-JDCCHMEXSA-N O=C1Nc(cccc2)c2/C1=C\c1ccc(c(/C=C/c2ccccn2)n[nH]2)c2c1 Chemical compound O=C1Nc(cccc2)c2/C1=C\c1ccc(c(/C=C/c2ccccn2)n[nH]2)c2c1 BPGUPPRJBLLMOX-JDCCHMEXSA-N 0.000 description 1
- FWSSMHXWOLSPAA-WUXMJOGZSA-N O=C1Nc(nccc2)c2/C1=C\c1ccc(cn[nH]2)c2c1 Chemical compound O=C1Nc(nccc2)c2/C1=C\c1ccc(cn[nH]2)c2c1 FWSSMHXWOLSPAA-WUXMJOGZSA-N 0.000 description 1
- YOGBNAVTRJPWBO-QGMBQPNBSA-N O=C1Nc2cc(-c3cnccc3)ccc2/C1=C\c1ccc(cn[nH]2)c2c1 Chemical compound O=C1Nc2cc(-c3cnccc3)ccc2/C1=C\c1ccc(cn[nH]2)c2c1 YOGBNAVTRJPWBO-QGMBQPNBSA-N 0.000 description 1
- ZYBQEZCFMPZWOV-VZUCSPMQSA-N O=C1Nc2ccccc2/C1=C\c1cc(Cl)c(cn[nH]2)c2c1 Chemical compound O=C1Nc2ccccc2/C1=C\c1cc(Cl)c(cn[nH]2)c2c1 ZYBQEZCFMPZWOV-VZUCSPMQSA-N 0.000 description 1
- IASZMZSQVJBKSL-AEAXTBIWSA-N O=C1Nc2ncccc2/C1=C\c1ccc(c(/C=C/c2ccncc2)n[nH]2)c2c1 Chemical compound O=C1Nc2ncccc2/C1=C\c1ccc(c(/C=C/c2ccncc2)n[nH]2)c2c1 IASZMZSQVJBKSL-AEAXTBIWSA-N 0.000 description 1
- JELULNODQHPMJY-UHFFFAOYSA-N O=Cc1ccc2c(C#Cc3cccnc3)n[nH]c2c1 Chemical compound O=Cc1ccc2c(C#Cc3cccnc3)n[nH]c2c1 JELULNODQHPMJY-UHFFFAOYSA-N 0.000 description 1
- MIUOLLPIUVFVMU-WOJGMQOQSA-N OC1Nc2ccccc2/C1=C\c(cc1)cc2c1c(-c1cc(cccc3)c3[nH]1)n[nH]2 Chemical compound OC1Nc2ccccc2/C1=C\c(cc1)cc2c1c(-c1cc(cccc3)c3[nH]1)n[nH]2 MIUOLLPIUVFVMU-WOJGMQOQSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M [O-]C(C(F)(F)F)=O Chemical compound [O-]C(C(F)(F)F)=O DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
Images
Classifications
-
- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- 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
-
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D417/14—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 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US886507P | 2007-12-21 | 2007-12-21 | |
| US13171708P | 2008-06-11 | 2008-06-11 | |
| PCT/CA2008/002227 WO2009079767A1 (en) | 2007-12-21 | 2008-12-19 | Indazolyl, benzimidazolyl, benzotriazolyl substituted indolinone derivatives as kinase inhibitors useful in the treatment of cancer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011506494A true JP2011506494A (ja) | 2011-03-03 |
| JP2011506494A5 JP2011506494A5 (enExample) | 2012-02-16 |
Family
ID=40800609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010538297A Withdrawn JP2011506494A (ja) | 2007-12-21 | 2008-12-19 | 癌の治療に有用なキナーゼ阻害剤としてのインダゾリル、ベンズイミダゾリル、ベンゾトリアゾリル置換インドルモン誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8765748B2 (enExample) |
| EP (1) | EP2235004A4 (enExample) |
| JP (1) | JP2011506494A (enExample) |
| CN (1) | CN101970426A (enExample) |
| AU (1) | AU2008340991B2 (enExample) |
| CA (1) | CA2709536C (enExample) |
| WO (1) | WO2009079767A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016537326A (ja) * | 2013-10-18 | 2016-12-01 | ユニバーシティー ヘルス ネットワーク | Plk4阻害剤の塩および結晶形態 |
| JP2024521657A (ja) * | 2021-05-11 | 2024-06-04 | オリック ファーマシューティカルズ,インク. | ポロ様キナーゼ4阻害剤 |
| US12325700B2 (en) | 2019-04-24 | 2025-06-10 | University Health Network | Crystal form S4 of the PLK4 inhibitor (1R,2S)-(e)-2-(3-(4-((cis-2,6-dimethylmorpholino)methyl)styryl)-1 h-imidazol-6-yl)-5′-methoxyspiro[cyclopropane-1,3′-indolin]-2′-one fumarate |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011506494A (ja) | 2007-12-21 | 2011-03-03 | ユニバーシティ・ヘルス・ネットワーク | 癌の治療に有用なキナーゼ阻害剤としてのインダゾリル、ベンズイミダゾリル、ベンゾトリアゾリル置換インドルモン誘導体 |
| CA2756568C (en) | 2009-04-06 | 2018-02-13 | University Health Network | Kinase inhibitors and method of treating cancer with same |
| PT2556071T (pt) | 2010-04-06 | 2016-11-22 | Univ Health Network | Inibidores de quinase e seus usos no tratamento de cancro |
| US8933070B2 (en) | 2010-07-02 | 2015-01-13 | University Health Network | Methods of targeting PTEN mutant diseases and compositions therefor |
| WO2012048411A1 (en) * | 2010-10-13 | 2012-04-19 | University Health Network | Plk-4 inhibitors and method of treating cancer with same |
| CN102295640B (zh) * | 2011-06-29 | 2013-09-18 | 南京工业大学 | 3-杂环席夫碱-5-氟-吲哚-2-酮类化合物及其制备方法和应用 |
| CN103006642B (zh) * | 2013-01-04 | 2014-10-22 | 中国药科大学 | 一类炔亚甲基吲哚-2-酮类衍生物的用途 |
| JP2016533350A (ja) | 2013-10-04 | 2016-10-27 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 植物のストレス耐性を増大させるための置換されているジヒドロオキシインドリルスルホンアミド類又はその塩の使用 |
| JP6525983B2 (ja) | 2013-10-18 | 2019-06-05 | ユニバーシティー ヘルス ネットワーク | 膵癌の治療法 |
| WO2015164956A1 (en) * | 2014-04-29 | 2015-11-05 | The University Of British Columbia | Benzisothiazole derivative compounds as therapeutics and methods for their use |
| US10633375B2 (en) | 2016-08-31 | 2020-04-28 | Jinagsu Hengrui Medicine Co., Ltd | Oxopicolinamide derivative, preparation method therefor and pharmaceutical use thereof |
| CN106916143B (zh) * | 2017-03-14 | 2019-09-27 | 哈尔滨医科大学 | 一种预防和治疗冠心病的药物及其应用 |
| TW202300485A (zh) * | 2021-03-02 | 2023-01-01 | 大陸商上海齊魯製藥研究中心有限公司 | Plk4抑制劑及其用途 |
| WO2024209363A1 (en) | 2023-04-06 | 2024-10-10 | Pfizer Inc. | Substituted indazole propionic acid derivative compounds and uses thereof as ampk activators |
| ES3022196A1 (es) * | 2023-11-27 | 2025-05-28 | Univ Madrid Complutense | Derivados de 2-indolinona y usos de los mismos |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1326A (en) * | 1839-09-17 | Improvement in the mode of setting and arranging sugar-kettles | ||
| DE3310891A1 (de) * | 1983-03-25 | 1984-09-27 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue indolinon-(2)-derivate, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und zwischenprodukte |
| US5182397A (en) * | 1990-05-31 | 1993-01-26 | American Cyanamid Company | Aryloxyspiroalkylindolinone herbicides |
| GB9507298D0 (en) | 1995-04-07 | 1995-05-31 | Pharmacia Spa | Substituted indolylmethylene-oxindale analogues as tyrosine kinase inhibitors |
| US5880141A (en) | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| ATE308520T1 (de) * | 1996-08-23 | 2005-11-15 | Sugen Inc | Kombinatorische bibliotheken von indolinone und verwandte produkte und verfahren zur behandlung von krankheiten |
| GB9716557D0 (en) | 1997-08-06 | 1997-10-08 | Glaxo Group Ltd | Benzylidene-1,3-dihydro-indol-2-one derivatives having anti-cancer activity |
| US6133305A (en) * | 1997-09-26 | 2000-10-17 | Sugen, Inc. | 3-(substituted)-2-indolinones compounds and use thereof as inhibitors of protein kinase activity |
| AU5468499A (en) * | 1998-08-04 | 2000-02-28 | Sugen, Inc. | 3-methylidenyl-2-indolinone modulators of protein kinase |
| EP1165513A1 (en) | 1999-03-24 | 2002-01-02 | Sugen, Inc. | Indolinone compounds as kinase inhibitors |
| US7148249B2 (en) | 2002-09-12 | 2006-12-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Indolinones substituted by heterocycles, the preparation thereof and their use as medicaments |
| US7205328B2 (en) * | 2002-10-21 | 2007-04-17 | Irm Llc | Oxindoles with anti-HIV activity |
| WO2005058309A1 (en) * | 2003-12-16 | 2005-06-30 | Leo Pharma A/S | Novel therapeutic use of indolinone derivatives |
| US7309787B2 (en) | 2005-07-13 | 2007-12-18 | Allergan, Inc. | Kinase inhibitors |
| US20070135509A1 (en) * | 2005-12-09 | 2007-06-14 | Blackburn Thomas P | Indolone compounds useful to treat cognitive impairment |
| US8207179B2 (en) | 2007-06-12 | 2012-06-26 | Boehringer Ingelheim International Gmbh | Substituted indolines as tyrosine kinase inhibitors |
| JP2011506494A (ja) | 2007-12-21 | 2011-03-03 | ユニバーシティ・ヘルス・ネットワーク | 癌の治療に有用なキナーゼ阻害剤としてのインダゾリル、ベンズイミダゾリル、ベンゾトリアゾリル置換インドルモン誘導体 |
| EP2108641A1 (en) | 2008-04-11 | 2009-10-14 | Laboratorios Almirall, S.A. | New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors |
| EP2113503A1 (en) | 2008-04-28 | 2009-11-04 | Laboratorios Almirall, S.A. | New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors |
| CA2756568C (en) | 2009-04-06 | 2018-02-13 | University Health Network | Kinase inhibitors and method of treating cancer with same |
| PT2556071T (pt) * | 2010-04-06 | 2016-11-22 | Univ Health Network | Inibidores de quinase e seus usos no tratamento de cancro |
-
2008
- 2008-12-19 JP JP2010538297A patent/JP2011506494A/ja not_active Withdrawn
- 2008-12-19 US US12/808,961 patent/US8765748B2/en active Active
- 2008-12-19 CN CN2008801272472A patent/CN101970426A/zh active Pending
- 2008-12-19 EP EP08865534A patent/EP2235004A4/en not_active Withdrawn
- 2008-12-19 AU AU2008340991A patent/AU2008340991B2/en not_active Ceased
- 2008-12-19 CA CA2709536A patent/CA2709536C/en active Active
- 2008-12-19 WO PCT/CA2008/002227 patent/WO2009079767A1/en not_active Ceased
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016537326A (ja) * | 2013-10-18 | 2016-12-01 | ユニバーシティー ヘルス ネットワーク | Plk4阻害剤の塩および結晶形態 |
| US10392374B2 (en) | 2013-10-18 | 2019-08-27 | University Health Network | Salt and crystal forms of PLK-4 inhibitor |
| US10472353B2 (en) | 2013-10-18 | 2019-11-12 | University Health Network | Salt and crystal forms of PLK-4 inhibitor |
| US10919886B2 (en) | 2013-10-18 | 2021-02-16 | University Health Network | Salt and crystal forms of PLK-4 inhibitor |
| US11667627B2 (en) | 2013-10-18 | 2023-06-06 | University Health Network | Salt and crystal forms of PLK-4 inhibitor |
| US12325700B2 (en) | 2019-04-24 | 2025-06-10 | University Health Network | Crystal form S4 of the PLK4 inhibitor (1R,2S)-(e)-2-(3-(4-((cis-2,6-dimethylmorpholino)methyl)styryl)-1 h-imidazol-6-yl)-5′-methoxyspiro[cyclopropane-1,3′-indolin]-2′-one fumarate |
| JP2024521657A (ja) * | 2021-05-11 | 2024-06-04 | オリック ファーマシューティカルズ,インク. | ポロ様キナーゼ4阻害剤 |
| JP7717842B2 (ja) | 2021-05-11 | 2025-08-04 | オリック ファーマシューティカルズ,インク. | ポロ様キナーゼ4阻害剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| US8765748B2 (en) | 2014-07-01 |
| EP2235004A4 (en) | 2011-05-04 |
| CN101970426A (zh) | 2011-02-09 |
| CA2709536A1 (en) | 2009-07-02 |
| CA2709536C (en) | 2016-05-31 |
| WO2009079767A9 (en) | 2009-10-01 |
| EP2235004A1 (en) | 2010-10-06 |
| AU2008340991A1 (en) | 2009-07-02 |
| AU2008340991B2 (en) | 2012-02-23 |
| WO2009079767A1 (en) | 2009-07-02 |
| US20110065702A1 (en) | 2011-03-17 |
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