CN102219784A - 可用于抑制chk1的杂芳基脲衍生物 - Google Patents
可用于抑制chk1的杂芳基脲衍生物 Download PDFInfo
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- CN102219784A CN102219784A CN2011101022112A CN201110102211A CN102219784A CN 102219784 A CN102219784 A CN 102219784A CN 2011101022112 A CN2011101022112 A CN 2011101022112A CN 201110102211 A CN201110102211 A CN 201110102211A CN 102219784 A CN102219784 A CN 102219784A
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- methyl
- pyrazine
- urea
- ylmethoxy
- phenyl
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Classifications
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- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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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
- C07D401/02—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 two hetero rings
- C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
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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
- C07D403/12—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
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- 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
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- 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
- C07D417/02—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 two hetero rings
- C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66602605P | 2005-03-29 | 2005-03-29 | |
| US60/666,026 | 2005-03-29 |
Related Parent Applications (1)
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5221367A (en) | 1988-08-03 | 1993-06-22 | International Business Machines, Corp. | Strained defect-free epitaxial mismatched heterostructures and method of fabrication |
| NZ575394A (en) | 2006-10-20 | 2012-01-12 | Icos Corp | Compositions of chk1 inhibitors and cyclodextrin |
| CN101200429B (zh) * | 2006-12-13 | 2012-08-22 | 上海睿智化学研究有限公司 | 2-硝基-4,5-二卤代苯酚类和2-氨基-4,5-二卤代苯酚类及其盐及其合成方法 |
| GB201008005D0 (en) | 2010-05-13 | 2010-06-30 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| AU2014293013A1 (en) | 2013-07-26 | 2016-03-17 | Race Oncology Ltd. | Combinatorial methods to improve the therapeutic benefit of bisantrene |
| US11179394B2 (en) | 2014-06-17 | 2021-11-23 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of Chk1 and ATR inhibitors |
| TW201702218A (zh) | 2014-12-12 | 2017-01-16 | 美國杰克森實驗室 | 關於治療癌症、自體免疫疾病及神經退化性疾病之組合物及方法 |
| US11464774B2 (en) | 2015-09-30 | 2022-10-11 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of DNA damaging agents and ATR inhibitors |
| CA3013514C (en) | 2016-02-04 | 2021-11-23 | Pharmaengine, Inc. | 3,5-disubstituted pyrazoles useful as checkpoint kinase 1 (chk1) inhibitors, and their preparations and applications |
| CN120661674A (zh) | 2016-03-15 | 2025-09-19 | 奥莱松基因组股份有限公司 | 用于治疗实体瘤的lsd1抑制剂的组合 |
| KR20190130621A (ko) * | 2017-03-31 | 2019-11-22 | 시애틀 지네틱스, 인크. | Chk1 저해제와 wee1 저해제의 조합물 |
| EP3461480A1 (en) | 2017-09-27 | 2019-04-03 | Onxeo | Combination of a dna damage response cell cycle checkpoint inhibitors and belinostat for treating cancer |
| CN112457306A (zh) | 2019-09-06 | 2021-03-09 | 上海瑛派药业有限公司 | 3,5-二取代吡唑化合物作为激酶抑制剂及其应用 |
| US12404332B2 (en) * | 2020-03-13 | 2025-09-02 | Research Development Foundation | Methods for diagnosing and treating cancers |
| NL2039212B1 (en) | 2024-12-02 | 2026-06-23 | Stichting Het Nederlands Kanker Inst Antoni Van Leeuwenhoek Ziekenhuis | Mitotic cell phase enrichment and ionizing radiation |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4293552A (en) | 1978-02-27 | 1981-10-06 | Eli Lilly And Company | Novel 1-(mono-o-substituted benzoyl)-3-(substituted pyrazinyl) ureas |
| US6174993B1 (en) | 1997-05-21 | 2001-01-16 | The Children's Medical Center Corp. | Short peptides which selectively modulate the activity of serine/threonine kinases |
| US6218109B1 (en) | 1997-09-05 | 2001-04-17 | Baylor College Of Medicine | Mammalian checkpoint genes and proteins |
| GB9718952D0 (en) | 1997-09-05 | 1997-11-12 | Medical Res Council | Mammalian chk1 effector cell cycle checkpoint protein kinase materials and methods |
| DE69818083T2 (de) | 1997-10-06 | 2004-07-08 | Abbott Gmbh & Co. Kg | INDENO[1,2-c]-,NAPHTHO[1,2-C]-UND BENZO[6,7]CYCLOHEPTA[1,2-c]PYRAZOLDERIVATE |
| EP1135135A4 (en) | 1998-09-18 | 2006-08-09 | Smithkline Beecham Corp | CHK1 KINASE INHIBITORS |
| YU54202A (sh) | 2000-01-18 | 2006-01-16 | Agouron Pharmaceuticals Inc. | Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije |
| HN2001000008A (es) | 2000-01-21 | 2003-12-11 | Inc Agouron Pharmaceuticals | Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo |
| WO2001057206A2 (en) | 2000-02-03 | 2001-08-09 | Ribozyme Pharmaceuticals, Inc. | Method and reagent for the inhibition of checkpoint kinase-1 (chk 1) enzyme |
| WO2001062900A1 (en) | 2000-02-25 | 2001-08-30 | The Regents Of The University Of California. | Scytonemin and methods of using thereof |
| US6211164B1 (en) | 2000-03-10 | 2001-04-03 | Abbott Laboratories | Antisense oligonucleotides of the human chk1 gene and uses thereof |
| US6534691B2 (en) | 2000-07-18 | 2003-03-18 | E. I. Du Pont De Nemours And Company | Manufacturing process for α-olefins |
| MXPA03001452A (es) | 2000-08-18 | 2004-05-04 | Agouron Pharma | Hidroximino-fluorenos heterociclicos y su uso para la inhibicion de las proteinas cinasas. |
| US20040116497A1 (en) | 2001-01-26 | 2004-06-17 | Gabriella Traquandi | Chromane derivatives, process for their preparation and their use as antitumor agents |
| UA76977C2 (en) | 2001-03-02 | 2006-10-16 | Icos Corp | Aryl- and heteroaryl substituted chk1 inhibitors and their use as radiosensitizers and chemosensitizers |
| JP2004536113A (ja) | 2001-07-03 | 2004-12-02 | カイロン コーポレイション | チロシンキナーゼおよびセリン/スレオニンキナーゼのインヒビターとしてのインダゾールベンズイミダゾール化合物 |
| WO2003028724A1 (en) | 2001-10-04 | 2003-04-10 | Smithkline Beecham Corporation | Chk1 kinase inhibitors |
| WO2003029241A1 (en) | 2001-10-04 | 2003-04-10 | Smithkline Beecham Corporation | Chk1 kinase inhibitors |
| US7166639B2 (en) | 2001-10-04 | 2007-01-23 | Smithkline Beecham Corporation | NF-κB inhibitors |
| WO2003028731A1 (en) | 2001-10-04 | 2003-04-10 | Smithkline Beecham Corporation | Chk1 kinase inhibitors |
| AU2002356871A1 (en) | 2001-10-30 | 2003-05-12 | Pharmacia Corporation | Heteroaromatic carboxamide derivatives for the treatment of inflammation |
| US20030187026A1 (en) | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| US20030119839A1 (en) | 2001-12-13 | 2003-06-26 | Nan-Horng Lin | Protein kinase inhibitors |
| AU2003224341A1 (en) | 2002-04-26 | 2003-11-10 | Warner-Lambert Company Llc | Inhibitors of checkpoint kinases (wee1 and chk1) |
| AU2003243318A1 (en) * | 2002-05-29 | 2003-12-19 | Millennium Pharmaceuticals, Inc. | Diarylurea compounds and derivatives as chk-1 inhibitors for the treatment of cancer |
| US20040034038A1 (en) | 2002-08-13 | 2004-02-19 | Goaquan Li | Urea kinase inhibitors |
| US7056925B2 (en) * | 2002-08-13 | 2006-06-06 | Abbott Laboratories | Urea kinase inhibitors |
| EP2573079A3 (en) | 2002-08-23 | 2015-03-11 | Novartis AG | Benzimidazole quinolinones and uses thereof |
| WO2004048343A1 (en) | 2002-11-28 | 2004-06-10 | Schering Aktiengesellschaft | Chk-, pdk- and akt-inhibitory pyrimidines, their production and use as pharmaceutical agents |
| EA009337B1 (ru) | 2003-01-09 | 2007-12-28 | Пфайзер Инк. | Трициклические соединения, представляющие собой ингибиторы протеинкиназ, для увеличения эффективности противоопухолевых агентов и лучевой терапии |
| AU2005267185A1 (en) * | 2004-06-25 | 2006-02-02 | Icos Corporation | Bisarylurea derivatives useful for inhibiting CHK1 |
| CA2679908A1 (en) | 2009-09-23 | 2011-03-23 | Shell Internationale Research Maatschappij B.V. | Closed loop solvent extraction process for oil sands |
| CN104407475B (zh) | 2014-12-04 | 2017-04-05 | 厦门天马微电子有限公司 | 液晶显示面板 |
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