TW201408658A - 絲胺酸／酥胺酸激酶抑制劑 - Google Patents
絲胺酸／酥胺酸激酶抑制劑 Download PDFInfo
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- TW201408658A TW201408658A TW102130680A TW102130680A TW201408658A TW 201408658 A TW201408658 A TW 201408658A TW 102130680 A TW102130680 A TW 102130680A TW 102130680 A TW102130680 A TW 102130680A TW 201408658 A TW201408658 A TW 201408658A
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
-
- 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
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
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- Organic Chemistry (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
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- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
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| MX340756B (es) | 2011-08-04 | 2016-07-25 | Array Biopharma Inc | Compuestos de quinazolina como inhibidores de serina/treonina quinasa. |
| PT2820009T (pt) | 2012-03-01 | 2018-04-12 | Array Biopharma Inc | Inibidores de serina/treonina quinases |
| KR102127026B1 (ko) * | 2012-07-27 | 2020-06-25 | 비오겐 엠에이 아이엔씨. | Atx 조절제들 |
| CA2884766A1 (en) | 2012-10-16 | 2014-04-24 | Daniel Jon Burdick | Serine/threonine kinase inhibitors |
| US9532987B2 (en) | 2013-09-05 | 2017-01-03 | Genentech, Inc. | Use of a combination of a MEK inhibitor and an ERK inhibitor for treatment of hyperproliferative diseases |
| EA031243B1 (ru) | 2013-12-06 | 2018-12-28 | Дженентек, Инк. | Ингибиторы серин/треонинкиназ |
| CN105980387B (zh) | 2013-12-30 | 2019-04-19 | 阵列生物制药公司 | 丝氨酸/苏氨酸激酶抑制剂 |
| CA2934679C (en) | 2013-12-30 | 2023-02-28 | Genentech, Inc. | Serine/threonine kinase inhibitors |
| WO2016106009A1 (en) * | 2014-12-22 | 2016-06-30 | Eli Lilly And Company | Erk inhibitors |
| CN109072311A (zh) | 2016-04-15 | 2018-12-21 | 豪夫迈·罗氏有限公司 | 用于癌症的诊断和治疗方法 |
| CN106749117B (zh) * | 2016-11-29 | 2018-10-09 | 北京怡力生物科技有限公司 | 一种3-氨基甲基四氢呋喃的制备方法 |
| MA48994A (fr) | 2017-03-30 | 2020-02-05 | Hoffmann La Roche | Isoquinoléines utilisées en tant qu'inhibiteurs de hpk1 |
| JP6906105B2 (ja) * | 2017-06-16 | 2021-07-21 | 成都先導薬物開発股▲ふん▼有限公司Ｈｉｔｇｅｎ Ｌｔｄ． | Ｒｏｃｋを阻害する化合物及びその使用 |
| WO2019051296A1 (en) | 2017-09-08 | 2019-03-14 | Genentech, Inc. | DIAGNOSTIC AND THERAPEUTIC METHODS OF CANCER |
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| TW202024053A (zh) | 2018-10-02 | 2020-07-01 | 美商建南德克公司 | 異喹啉化合物及其用途 |
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| EP4211119A4 (en) * | 2020-09-02 | 2024-11-06 | Merck Sharp & Dohme LLC | 2-AMINOQUINAZOLINES AS LRRK2 INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT672042E (pt) | 1993-10-01 | 2006-08-31 | Novartis Ag | Derivados de pirimidinoamina farmacologicamente activos e processos para a sua preparacao |
| JPH08503971A (ja) | 1993-10-01 | 1996-04-30 | チバ−ガイギー アクチェンゲゼルシャフト | ピリミジンアミン誘導体及びその調製のための方法 |
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| BR9713863A (pt) | 1996-12-05 | 2000-03-14 | Amgen Inc | Composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, processos de profilaxia ou tratamento, para abaixar as concentrações no plasma, para diminuir a produção de prostaglandinas, e, para diminuir a atividade de enzima ciclooxigenase |
| GB9812683D0 (en) * | 1998-06-12 | 1998-08-12 | Smithkline Beecham Plc | Novel compounds |
| US6602872B1 (en) | 1999-12-13 | 2003-08-05 | Merck & Co., Inc. | Substituted pyridazines having cytokine inhibitory activity |
| BR0108611A (pt) | 2000-02-25 | 2003-05-06 | Hoffmann La Roche | Moduladores de receptor de adenosina |
| ATE284712T1 (de) | 2000-04-26 | 2005-01-15 | Eisai Co Ltd | Medizinische zusammensetzungen zur förderung der aktivierung der eingeweide |
| WO2002088079A2 (en) | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| WO2003030909A1 (en) | 2001-09-25 | 2003-04-17 | Bayer Pharmaceuticals Corporation | 2- and 4-aminopyrimidines n-substtituded by a bicyclic ring for use as kinase inhibitors in the treatment of cancer |
| CA2485166A1 (en) | 2002-05-21 | 2003-12-04 | Amgen Inc. | Substituted pyrimidinone and pyridinone compounds |
| JP4530852B2 (ja) | 2002-07-15 | 2010-08-25 | メルク・シャープ・エンド・ドーム・コーポレイション | 糖尿病治療のためのピペリジノピリミジンジペプチジルペプチダーゼ阻害剤 |
| TW200533357A (en) | 2004-01-08 | 2005-10-16 | Millennium Pharm Inc | 2-(amino-substituted)-4-aryl pyrimidines and related compounds useful for treating inflammatory diseases |
| EP1742634B1 (en) | 2004-04-13 | 2010-10-27 | ICAgen, Inc. | Polycyclic pyrimidines as potassium ion channel modulators |
| US7429604B2 (en) | 2004-06-15 | 2008-09-30 | Bristol Myers Squibb Company | Six-membered heterocycles useful as serine protease inhibitors |
| WO2006021458A2 (en) | 2004-08-27 | 2006-03-02 | Gpc Biotech Ag | Pyrimidine derivatives |
| GB0420722D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| GB0428514D0 (en) | 2004-12-31 | 2005-02-09 | Prosidion Ltd | Compounds |
| US20070078135A1 (en) | 2005-04-18 | 2007-04-05 | Neurogen Corporation | Substituted heteroaryl CB1 antagonists |
| US7572809B2 (en) | 2005-12-19 | 2009-08-11 | Hoffmann-La Roche Inc. | Isoquinoline aminopyrazole derivatives |
| MX2008010635A (es) | 2006-02-16 | 2008-10-28 | Schering Corp | Derivados de pirrolidina como inhibidores de cinasa regulada por señales extracelulares. |
| JP2009535393A (ja) * | 2006-05-01 | 2009-10-01 | ファイザー・プロダクツ・インク | 置換２−アミノ縮合複素環式化合物 |
| DE102006035202A1 (de) | 2006-07-29 | 2008-01-31 | Lanxess Deutschland Gmbh | Konservierungsmittel auf Basis von Carbonsäureanhydriden |
| TWI389899B (zh) * | 2006-08-08 | 2013-03-21 | Msd Oss Bv | 具口服活性之凝血酶抑制劑 |
| ATE530540T1 (de) | 2006-08-23 | 2011-11-15 | Pfizer Prod Inc | Pyrimidonverbindungen als gsk-3-inhibitoren |
| WO2008039882A1 (en) | 2006-09-30 | 2008-04-03 | Sanofi-Aventis U.S. Llc | A combination of niacin and a prostaglandin d2 receptor antagonist |
| BRPI0720635A2 (pt) | 2006-12-22 | 2014-01-07 | Novartis Ag | Compostos orgânicos e seus usos |
| EP2200436B1 (en) | 2007-09-04 | 2015-01-21 | The Scripps Research Institute | Substituted pyrimidinyl-amines as protein kinase inhibitors |
| JP2011503006A (ja) | 2007-11-06 | 2011-01-27 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 殺菌性複素環アミン |
| WO2009146034A2 (en) | 2008-03-31 | 2009-12-03 | Takeda Pharmaceutical Company Limited | Mapk/erk kinase inhibitors and methods of use thereof |
| NZ589843A (en) | 2008-06-27 | 2012-12-21 | Avila Therapeutics Inc | Pyrimidine heteroaryl compounds and uses thereof as protein kinase inhibitors |
| BRPI0913966A2 (pt) | 2008-06-27 | 2015-11-17 | Novartis Ag | compostos orgânicos |
| US8940891B2 (en) | 2008-12-08 | 2015-01-27 | Arena Pharmaceuticals, Inc. | Modulators of the prostacyclin (PGI2) receptor useful for the treatment of disorders related thereto |
| RU2013143839A (ru) | 2011-02-28 | 2015-04-10 | Эррэй Биофарма Инк. | Ингибиторы сериновых/треониновых киназ |
| MX340756B (es) * | 2011-08-04 | 2016-07-25 | Array Biopharma Inc | Compuestos de quinazolina como inhibidores de serina/treonina quinasa. |
| PT2820009T (pt) | 2012-03-01 | 2018-04-12 | Array Biopharma Inc | Inibidores de serina/treonina quinases |
-
2013
- 2013-08-27 HK HK15111084.7A patent/HK1210174A1/xx unknown
- 2013-08-27 CN CN201380051518.1A patent/CN105143200B/zh active Active
- 2013-08-27 KR KR1020157007729A patent/KR20150047597A/ko not_active Withdrawn
- 2013-08-27 JP JP2015529957A patent/JP6378182B2/ja active Active
- 2013-08-27 MX MX2015002508A patent/MX369989B/es active IP Right Grant
- 2013-08-27 AR ARP130103040A patent/AR092253A1/es unknown
- 2013-08-27 BR BR112015004548A patent/BR112015004548A2/pt not_active IP Right Cessation
- 2013-08-27 EP EP13759395.0A patent/EP2888247B1/en active Active
- 2013-08-27 WO PCT/US2013/056876 patent/WO2014036015A1/en not_active Ceased
- 2013-08-27 US US14/011,501 patent/US9388171B2/en active Active
- 2013-08-27 TW TW102130680A patent/TW201408658A/zh unknown
- 2013-08-27 RU RU2015110985A patent/RU2644947C2/ru not_active IP Right Cessation
- 2013-08-27 CA CA2882750A patent/CA2882750A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP6378182B2 (ja) | 2018-08-22 |
| BR112015004548A2 (pt) | 2017-08-08 |
| CN105143200A (zh) | 2015-12-09 |
| EP2888247B1 (en) | 2020-03-25 |
| MX2015002508A (es) | 2015-10-12 |
| HK1210174A1 (en) | 2016-04-15 |
| JP2015526519A (ja) | 2015-09-10 |
| WO2014036015A1 (en) | 2014-03-06 |
| CN105143200B (zh) | 2018-10-16 |
| RU2644947C2 (ru) | 2018-02-15 |
| AR092253A1 (es) | 2015-04-08 |
| RU2015110985A (ru) | 2016-10-20 |
| KR20150047597A (ko) | 2015-05-04 |
| US20140066453A1 (en) | 2014-03-06 |
| US9388171B2 (en) | 2016-07-12 |
| MX369989B (es) | 2019-11-27 |
| CA2882750A1 (en) | 2014-03-06 |
| EP2888247A1 (en) | 2015-07-01 |
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