JP2011506494A5 - - Google Patents
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- Publication number
- JP2011506494A5 JP2011506494A5 JP2010538297A JP2010538297A JP2011506494A5 JP 2011506494 A5 JP2011506494 A5 JP 2011506494A5 JP 2010538297 A JP2010538297 A JP 2010538297A JP 2010538297 A JP2010538297 A JP 2010538297A JP 2011506494 A5 JP2011506494 A5 JP 2011506494A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- optionally substituted
- phenyl
- halogen
- 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- Withdrawn
Links
- 125000000217 alkyl group Chemical group 0.000 claims 99
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 78
- 229910052736 halogen Inorganic materials 0.000 claims 61
- 150000002367 halogens Chemical group 0.000 claims 60
- 125000001424 substituent group Chemical group 0.000 claims 47
- -1 hydroxy, nitro, cyano, amino, phenyl Chemical group 0.000 claims 37
- 150000001875 compounds Chemical class 0.000 claims 32
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 30
- 125000004663 dialkyl amino group Chemical group 0.000 claims 30
- 125000001072 heteroaryl group Chemical group 0.000 claims 24
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 23
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims 22
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 21
- 125000001188 haloalkyl group Chemical group 0.000 claims 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 20
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 125000003282 alkyl amino group Chemical group 0.000 claims 15
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 14
- 125000004438 haloalkoxy group Chemical group 0.000 claims 14
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 12
- 125000004103 aminoalkyl group Chemical group 0.000 claims 12
- 125000001931 aliphatic group Chemical group 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 10
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 5
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000004450 alkenylene group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000004970 halomethyl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000021309 Germ cell tumor Diseases 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 201000010915 Glioblastoma multiforme Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010027406 Mesothelioma Diseases 0.000 claims 1
- 208000034176 Neoplasms, Germ Cell and Embryonal Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical group CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229960005222 phenazone Drugs 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 0 *N(C(CCCCCC1)=C1C1=*c2cc(***3)c3cc2)C1=O Chemical compound *N(C(CCCCCC1)=C1C1=*c2cc(***3)c3cc2)C1=O 0.000 description 1
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 JP2011506494A (ja) | 2011-03-03 |
| JP2011506494A5 true 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) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2235004A4 (en) | 2007-12-21 | 2011-05-04 | Univ Health Network | INDAZOLYL, BENZIMIDAZOLYL, BENZOTRIAZOLYL-SUBSTITUTED INDOLUND DERIVATIVES AS A KINASE-HEMMER FOR CANCER TREATMENT |
| WO2010115279A1 (en) | 2009-04-06 | 2010-10-14 | University Health Network | Kinase inhibitors and method of treating cancer with same |
| TWI516262B (zh) * | 2010-04-06 | 2016-01-11 | 健康網路大學 | 激酶抑制劑及以其治療癌症的方法 |
| CA2803446C (en) | 2010-07-02 | 2019-06-04 | University Health Network | Use of plk4 antagonists for treating pten mutant diseases |
| 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 |
| AU2014331111B2 (en) | 2013-10-04 | 2018-05-31 | Bayer Cropscience Aktiencesellschaft | Use of substituted dihydro-oxindolyl sulfonamides, or the salts thereof, for increasing the stress tolerance of plants |
| TR201902875T4 (tr) | 2013-10-18 | 2019-03-21 | Univ Health Network | Plk-4 inhibitörünün tuz ve kristal formları. |
| EA030089B1 (ru) | 2013-10-18 | 2018-06-29 | Юниверсити Хелс Нетуорк | Лечение рака поджелудочной железы |
| WO2015164956A1 (en) * | 2014-04-29 | 2015-11-05 | The University Of British Columbia | Benzisothiazole derivative compounds as therapeutics and methods for their use |
| CN113912586B (zh) | 2016-08-31 | 2023-04-07 | 江苏恒瑞医药股份有限公司 | 氧代吡啶酰胺类衍生物、其制备方法及其在医药上的应用 |
| 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 |
| EP3959209A4 (en) | 2019-04-24 | 2022-12-28 | University Health Network | S4 CRYSTALLINE FORM OF A PLK4 INHIBITOR (1R,2S)-(E)-2-(3-(4-((CIS-2,6-DIMETHYLMORPHOLINO)METHYL)STYRYL)-1H-IMIDAZOL-6-YL )-5'-METHOXYSPIRO[CYCLOPROPANE-L,3'-INDOLIN]-2'-ONE FUMARATE |
| 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 |
| TWI926033B (zh) | 2021-05-11 | 2026-05-21 | 美商歐瑞克製藥公司 | 類ｐｏｌｏ激酶４抑制劑 |
| 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 |
| EP0929520B1 (en) * | 1996-08-23 | 2005-11-02 | Sugen, Inc. | Indolinone combinatorial libraries and related products and methods for the treatment of disease |
| 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 |
| CA2383623A1 (en) * | 1998-08-04 | 2000-02-17 | Sugen, Inc. | 3-methylidenyl-2-indolinone modulators of protein kinase |
| AU3770000A (en) | 1999-03-24 | 2000-10-09 | 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 |
| EP2181108A2 (en) | 2007-06-12 | 2010-05-05 | Boehringer Ingelheim International GmbH | 3-hetrocyclylidene-indolinone derivatives as inhibitors of specific cell cycle kinases |
| EP2235004A4 (en) | 2007-12-21 | 2011-05-04 | Univ Health Network | INDAZOLYL, BENZIMIDAZOLYL, BENZOTRIAZOLYL-SUBSTITUTED INDOLUND DERIVATIVES AS A KINASE-HEMMER FOR CANCER TREATMENT |
| 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 |
| WO2010115279A1 (en) | 2009-04-06 | 2010-10-14 | University Health Network | Kinase inhibitors and method of treating cancer with same |
| TWI516262B (zh) | 2010-04-06 | 2016-01-11 | 健康網路大學 | 激酶抑制劑及以其治療癌症的方法 |
-
2008
- 2008-12-19 EP EP08865534A patent/EP2235004A4/en not_active Withdrawn
- 2008-12-19 CA CA2709536A patent/CA2709536C/en active Active
- 2008-12-19 WO PCT/CA2008/002227 patent/WO2009079767A1/en not_active Ceased
- 2008-12-19 US US12/808,961 patent/US8765748B2/en not_active Expired - Fee Related
- 2008-12-19 CN CN2008801272472A patent/CN101970426A/zh active Pending
- 2008-12-19 JP JP2010538297A patent/JP2011506494A/ja not_active Withdrawn
- 2008-12-19 AU AU2008340991A patent/AU2008340991B2/en not_active Ceased
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