AU2014274093B2 - Compounds for kinase modulation, and indications therefor - Google Patents
Compounds for kinase modulation, and indications therefor Download PDFInfo
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- AU2014274093B2 AU2014274093B2 AU2014274093A AU2014274093A AU2014274093B2 AU 2014274093 B2 AU2014274093 B2 AU 2014274093B2 AU 2014274093 A AU2014274093 A AU 2014274093A AU 2014274093 A AU2014274093 A AU 2014274093A AU 2014274093 B2 AU2014274093 B2 AU 2014274093B2
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- LBRZLAQWSGKDTI-HNNXBMFYSA-N methyl N-[(2S)-1-[[4-[2-tert-butyl-4-[3-[[ethyl(methyl)sulfamoyl]amino]-2-fluorophenyl]-1,3-thiazol-5-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound CCN(C)S(=O)(=O)Nc1cccc(-c2nc(sc2-c2ccnc(NC[C@H](C)NC(=O)OC)n2)C(C)(C)C)c1F LBRZLAQWSGKDTI-HNNXBMFYSA-N 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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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
- A61K31/4353—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
- A61K31/437—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 five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
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- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A—HUMAN NECESSITIES
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361829190P | 2013-05-30 | 2013-05-30 | |
| US61/829,190 | 2013-05-30 | ||
| PCT/US2014/040076 WO2014194127A1 (en) | 2013-05-30 | 2014-05-29 | Compounds for kinase modulation, and indications therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2014274093A1 AU2014274093A1 (en) | 2015-12-03 |
| AU2014274093B2 true AU2014274093B2 (en) | 2018-11-08 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2014274093A Ceased AU2014274093B2 (en) | 2013-05-30 | 2014-05-29 | Compounds for kinase modulation, and indications therefor |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US9873700B2 (OSRAM) |
| EP (1) | EP3004060B1 (OSRAM) |
| JP (1) | JP2016520131A (OSRAM) |
| KR (1) | KR20160013028A (OSRAM) |
| CN (1) | CN105228983A (OSRAM) |
| AR (1) | AR096450A1 (OSRAM) |
| AU (1) | AU2014274093B2 (OSRAM) |
| BR (1) | BR112015028845A2 (OSRAM) |
| CA (1) | CA2912568A1 (OSRAM) |
| HK (1) | HK1219732A1 (OSRAM) |
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Families Citing this family (100)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| SG183036A1 (en) | 2007-07-17 | 2012-08-30 | Plexxikon Inc | Compounds and methods for kinase modulation, and indications therefor |
| WO2009143018A2 (en) | 2008-05-19 | 2009-11-26 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| AR077468A1 (es) | 2009-07-09 | 2011-08-31 | Array Biopharma Inc | Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa |
| CN102740698A (zh) | 2009-11-18 | 2012-10-17 | 普莱希科公司 | 用于激酶调节的化合物和方法及其适应症 |
| BR112012015745A2 (pt) | 2009-12-23 | 2016-05-17 | Plexxikon Inc | compostos e métodos para a modulação de quinase, e indicações dos mesmos |
| TWI619713B (zh) | 2010-04-21 | 2018-04-01 | 普雷辛肯公司 | 用於激酶調節的化合物和方法及其適應症 |
| KR101911972B1 (ko) | 2011-02-07 | 2018-10-25 | 플렉시콘 인코퍼레이티드 | 키나제 조절을 위한 화합물 및 방법, 및 그에 대한 적응증 |
| SG194847A1 (en) | 2011-05-17 | 2013-12-30 | Plexxikon Inc | Kinase modulation and indications therefor |
| US9358235B2 (en) | 2012-03-19 | 2016-06-07 | Plexxikon Inc. | Kinase modulation, and indications therefor |
| CA2871375C (en) * | 2012-05-03 | 2020-10-27 | F. Hoffmann-La Roche Ag | Pyrazole aminopyrimidine derivatives as lrrk2 modulators for use in the treatment of parkinson's disease |
| US9150570B2 (en) * | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| WO2014039714A2 (en) | 2012-09-06 | 2014-03-13 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| CN104870475B (zh) | 2012-10-25 | 2019-11-08 | 美国比奥维拉迪维股份有限公司 | 抗补体C1s抗体和其用途 |
| CA2895239C (en) | 2012-12-21 | 2020-10-27 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| WO2014145051A1 (en) | 2013-03-15 | 2014-09-18 | Jiazhong Zhang | Heterocyclic compounds and uses thereof |
| US20140303121A1 (en) | 2013-03-15 | 2014-10-09 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| BR112015028845A2 (pt) | 2013-05-30 | 2017-07-25 | Plexxikon Inc | compostos para a modulação da quinase e indicações da mesma |
| US9771369B2 (en) | 2014-03-04 | 2017-09-26 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| WO2016044067A1 (en) | 2014-09-15 | 2016-03-24 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| TN2017000374A1 (en) | 2015-03-02 | 2019-01-16 | Bristol Myers Squibb Co | TGF-β INHIBITORS |
| WO2016164641A1 (en) | 2015-04-08 | 2016-10-13 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| CN104829613B (zh) * | 2015-04-13 | 2020-06-09 | 赤峰蒙广生物科技有限公司 | 二芳基取代的吡唑并环类衍生物、其制备方法及其在医药领域的应用 |
| BR112017023540B1 (pt) | 2015-05-06 | 2023-04-04 | Plexxikon, Inc. | Processos de preparação de derivados de 1h-pirrolo[2,3-b]piridina que modulam quinases |
| HRP20201383T1 (hr) | 2015-05-06 | 2020-11-27 | Plexxikon Inc. | Kruti oblici spoja za moduliranje kinaza |
| WO2016191296A1 (en) * | 2015-05-22 | 2016-12-01 | Plexxikon Inc. | Plx-8394 or plx-7904 for use in the treatment of braf-v600-related diseases |
| US10316032B2 (en) * | 2015-05-22 | 2019-06-11 | Plexxikon Inc. | Solid forms of a compound for modulating kinases |
| RS61485B1 (sr) | 2015-07-16 | 2021-03-31 | Array Biopharma Inc | Supstituisana pirazolo [1,5-a] piridinska jedinjenja kao inhibitori ret kinaze |
| WO2017019804A2 (en) | 2015-07-28 | 2017-02-02 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| EP3353179B1 (en) | 2015-09-21 | 2022-02-09 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| TN2018000138A1 (en) | 2015-10-26 | 2019-10-04 | Array Biopharma Inc | Point mutations in trk inhibitor-resistant cancer and methods relating to the same |
| WO2017100201A1 (en) | 2015-12-07 | 2017-06-15 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| US9630968B1 (en) | 2015-12-23 | 2017-04-25 | Arqule, Inc. | Tetrahydropyranyl amino-pyrrolopyrimidinone and methods of use thereof |
| ES2904615T3 (es) | 2016-03-16 | 2022-04-05 | Plexxikon Inc | Compuestos y métodos para la modulación de quinasas e indicaciones al respecto |
| RS65988B1 (sr) | 2016-04-04 | 2024-10-31 | Loxo Oncology Inc | Postupak lečenja pedijatrijskih karcinoma |
| CN109414442B (zh) | 2016-04-04 | 2024-03-29 | 洛克索肿瘤学股份有限公司 | 一种化合物的液体制剂 |
| US10045991B2 (en) | 2016-04-04 | 2018-08-14 | Loxo Oncology, Inc. | Methods of treating pediatric cancers |
| DK3800189T3 (da) | 2016-05-18 | 2023-07-31 | Loxo Oncology Inc | Fremstilling af (s)-n-(5-((r)-2-(2,5-difluorphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidin-1-carboxamid |
| DK3472165T3 (da) * | 2016-06-21 | 2023-12-11 | Nerviano Medical Sciences Srl | N-(substituererede-phenyl)-sulfonamidderivater som kinasehæmmere |
| CN107722013B (zh) * | 2016-08-11 | 2021-01-12 | 中国科学院上海药物研究所 | 去氮嘌呤类化合物及其药物组合物、制备方法和用途 |
| SG11201901197PA (en) * | 2016-08-24 | 2019-03-28 | Arqule Inc | Amino-pyrrolopyrimidinone compounds and methods of use thereof |
| TW201815766A (zh) | 2016-09-22 | 2018-05-01 | 美商普雷辛肯公司 | 用於ｉｄｏ及ｔｄｏ調節之化合物及方法以及其適應症 |
| WO2018055097A1 (en) | 2016-09-23 | 2018-03-29 | Cellipse | Lim kinase inhibitors, pharmaceutical composition and method of use in limk-mediated diseases |
| TWI704148B (zh) | 2016-10-10 | 2020-09-11 | 美商亞雷生物製藥股份有限公司 | 作為ｒｅｔ激酶抑制劑之經取代吡唑并[1,5-a]吡啶化合物 |
| JOP20190077A1 (ar) | 2016-10-10 | 2019-04-09 | Array Biopharma Inc | مركبات بيرازولو [1، 5-a]بيريدين بها استبدال كمثبطات كيناز ret |
| JOP20190092A1 (ar) | 2016-10-26 | 2019-04-25 | Array Biopharma Inc | عملية لتحضير مركبات بيرازولو[1، 5-a]بيريميدين وأملاح منها |
| WO2018136202A2 (en) | 2016-12-23 | 2018-07-26 | Plexxikon Inc. | Compounds and methods for cdk8 modulation and indications therefor |
| JP7300394B2 (ja) | 2017-01-17 | 2023-06-29 | ヘパリジェニックス ゲーエムベーハー | 肝再生の促進又は肝細胞死の低減もしくは予防のためのプロテインキナーゼ阻害 |
| EP3571203B1 (en) | 2017-01-18 | 2023-06-07 | Array BioPharma Inc. | Substituted pyrazolo[1,5-a]pyrazine compounds as ret kinase inhibitors |
| WO2018136663A1 (en) | 2017-01-18 | 2018-07-26 | Array Biopharma, Inc. | Ret inhibitors |
| JOP20190213A1 (ar) | 2017-03-16 | 2019-09-16 | Array Biopharma Inc | مركبات حلقية ضخمة كمثبطات لكيناز ros1 |
| CA3056777A1 (en) | 2017-03-20 | 2018-09-27 | Plexxikon Inc. | Crystalline forms of 4-(1-(1,1-di(pyridin-2-yl)ethyl)-6-(3,5-dimethylisoxazol-4-yl)-1h- pyrrolo[3,2-b]pyridin-3-yl)benzoic acid that inhibits bromodomain |
| WO2018226846A1 (en) | 2017-06-07 | 2018-12-13 | Plexxikon Inc. | Compounds and methods for kinase modulation |
| TWI805599B (zh) | 2017-07-25 | 2023-06-21 | 美商第一三共公司 | 激酶調節化合物之調配物 |
| HRP20220609T1 (hr) * | 2017-07-29 | 2022-06-24 | Lutris Pharma Ltd. | Novi braf inhibitori i njihovo korištenje za tretiranje kožnih reakcija |
| TWI876442B (zh) | 2017-10-10 | 2025-03-11 | 美商絡速藥業公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之調配物 |
| TWI791053B (zh) | 2017-10-10 | 2023-02-01 | 美商亞雷生物製藥股份有限公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之結晶形式及其醫藥組合物 |
| US10717735B2 (en) | 2017-10-13 | 2020-07-21 | Plexxikon Inc. | Solid forms of a compound for modulating kinases |
| TWI803530B (zh) | 2017-10-27 | 2023-06-01 | 美商普雷辛肯公司 | 調節激酶之化合物之調配物 |
| CA3087578C (en) | 2018-01-18 | 2023-08-08 | Array Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidine compounds as ret kinase inhibitors |
| EP3740491A1 (en) | 2018-01-18 | 2020-11-25 | Array Biopharma, Inc. | Substituted pyrrolo[2,3-d]pyrimidines compounds as ret kinase inhibitors |
| CN111615514B (zh) | 2018-01-18 | 2022-10-11 | 奥瑞生物药品公司 | 作为ret激酶抑制剂的取代的吡唑并[4,3-c]吡啶化合物 |
| WO2019142128A1 (en) * | 2018-01-18 | 2019-07-25 | Integral Biosciences Private Limited | Dual inhibitors of alk5 and p38α map kinase |
| US11858927B2 (en) | 2018-01-31 | 2024-01-02 | Heparegenix Gmbh | Protein kinase MKK4 inhibitors for promoting liver regeneration or reducing or preventing hepatocyte death |
| WO2019183145A1 (en) | 2018-03-20 | 2019-09-26 | Plexxikon Inc. | Compounds and methods for ido and tdo modulation, and indications therefor |
| US11731968B2 (en) | 2018-06-21 | 2023-08-22 | Heparegenix Gmbh | Tricyclic protein kinase inhibitors for promoting liver regeneration or reducing or preventing hepatocyte death |
| KR102836327B1 (ko) | 2018-07-16 | 2025-07-21 | 헤파레게닉스 게엠베하 | 간 재생 촉진, 또는 간세포 사멸의 감소 또는 예방용 단백질 키나제 억제제 |
| CA3224945C (en) | 2018-07-31 | 2025-11-18 | Loxo Oncology, Inc. | SPRAY DRIED DISPERSIONS, FORMULATIONS AND POLYMORPHIES OF (S)-5-AMINO-3-(4-((5-FLUORO-2-METHOXYBENZAMIDO)METHYL)PHENYL)(1,1,1-TRIFLUOROPROPAN-2-YL)-1H-PYRAZOLE-4-CARBOXAMIDE |
| US11952387B2 (en) | 2018-08-21 | 2024-04-09 | Kyorin Pharmaceutical Co., Ltd | Bicyclic heteroaromatic ring derivative |
| JP2022500383A (ja) | 2018-09-10 | 2022-01-04 | アレイ バイオファーマ インコーポレイテッド | Ｒｅｔキナーゼ阻害剤としての縮合複素環式化合物 |
| DK3891142T3 (da) | 2018-12-03 | 2022-10-24 | Boehringer Ingelheim Int | Heteroaromatiske forbindelser som vanininhibitorer |
| CN113474337A (zh) | 2018-12-19 | 2021-10-01 | 奥瑞生物药品公司 | 作为fgfr抑制剂用于治疗癌症的7-((3，5-二甲氧基苯基)氨基)喹喔啉衍生物 |
| US12180207B2 (en) | 2018-12-19 | 2024-12-31 | Array Biopharma Inc. | Substituted pyrazolo[1,5-a]pyridine compounds as inhibitors of FGFR tyrosine kinases |
| WO2020124397A1 (en) * | 2018-12-19 | 2020-06-25 | Inventisbio Shanghai Ltd. | C-terminal src kinase inhibitors |
| AU2020271836B2 (en) | 2019-04-09 | 2025-11-13 | Opna Bio SA | Condensed azines for EP300 or CBP modulation and indications therefor |
| AU2020283597A1 (en) * | 2019-05-31 | 2021-11-25 | Fochon Biosciences, Ltd. | Substituted pyrrolo (2, 3-b) pyridine and pyrazolo (3, 4-b) pyridine derivatives as protein kinase inhibitors |
| TW202116754A (zh) | 2019-07-11 | 2021-05-01 | 美商Ｅ 斯蓋普生物股份有限公司 | 作為ｌｒｒｋ２抑制劑之吲唑及氮雜吲唑 |
| NZ785221A (en) | 2019-07-29 | 2025-08-29 | Heparegenix Gmbh | Heteroaryl-substituted pyrazolo-pyridine protein kinase inhibitors for promoting liver regeneration or reducing or preventing hepatocyte death |
| WO2021113492A1 (en) | 2019-12-06 | 2021-06-10 | Schrödinger, Inc. | Cyclic compounds and methods of using same |
| KR102836833B1 (ko) | 2019-12-10 | 2025-07-22 | 에프. 호프만-라 로슈 아게 | 신규 메틸퀴나졸리논 유도체 |
| BR112022012684A2 (pt) | 2019-12-27 | 2023-03-07 | Schroedinger Inc | Compostos cíclicos e métodos de uso dos mesmos |
| CN114981267B (zh) | 2020-01-15 | 2024-11-08 | 海帕瑞吉尼克斯股份有限公司 | 用于治疗肝脏疾病的mkk4抑制剂3-苯甲酰基-1h-吡咯并[2,3-b]吡啶衍生物 |
| AU2021261383A1 (en) | 2020-04-23 | 2022-11-17 | Opna Bio SA | Compounds and methods for CD73 modulation and indications therefor |
| EP4143168A1 (en) | 2020-04-29 | 2023-03-08 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| US20230303551A1 (en) * | 2020-08-13 | 2023-09-28 | Albert Einstein College Of Medicine | N-cyclyl-sulfonamides useful for inhibiting raf |
| JP2023542473A (ja) | 2020-08-21 | 2023-10-10 | プレキシコン インコーポレーテッド | 併用薬抗がん治療 |
| US20230365584A1 (en) | 2020-09-10 | 2023-11-16 | Schrödinger, Inc. | Heterocyclic pericondensed cdc7 kinase inhibitors for the treatment of cancer |
| US20240148732A1 (en) | 2021-01-26 | 2024-05-09 | Schrödinger, Inc. | Tricyclic compounds useful in the treatment of cancer, autoimmune and inflammatory disorders |
| CN112574200B (zh) * | 2021-02-26 | 2021-06-11 | 安润医药科技（苏州）有限公司 | Btk和/或btk的突变体c481s的小分子抑制剂 |
| CN113018415B (zh) * | 2021-03-17 | 2022-07-01 | 遵义医科大学 | 一种药物组合及其应用 |
| TW202300150A (zh) | 2021-03-18 | 2023-01-01 | 美商薛定諤公司 | 環狀化合物及其使用方法 |
| CA3222612A1 (en) * | 2021-06-09 | 2022-12-15 | F. Hoffmann-La Roche Ag | New solid forms of (3r)-n-[2-cyano-4-fluoro-3-(3-methyl-4-oxo-quinazolin-6-yl)oxy-phenyl]-3-fluoro-pyrrolidine-1-sulfonamide |
| CN113941001B (zh) * | 2021-12-09 | 2023-09-08 | 宁夏医科大学 | Craf抑制剂在制备抗肿瘤的药物中的应用 |
| JP2025509886A (ja) | 2022-03-28 | 2025-04-11 | ニカング セラピューティクス， インコーポレイテッド | サイクリン依存性キナーゼ２阻害剤としてのスルホンアミド誘導体 |
| WO2023213965A1 (en) * | 2022-05-05 | 2023-11-09 | University Of Dundee | Inhibitors of cdk8 and cdk19 |
| WO2023240024A1 (en) * | 2022-06-08 | 2023-12-14 | Nikang Therapeutics, Inc. | Sulfamide derivatives as cyclin-dependent kinase 2 inhibitors |
| WO2025026377A1 (en) * | 2023-08-02 | 2025-02-06 | Insilico Medicine Ip Limited | Ectonucleotide pyrophosphatase-phosphodiesterase 1 (enpp1) inhibitors and uses thereof |
| WO2025059027A1 (en) | 2023-09-11 | 2025-03-20 | Schrödinger, Inc. | Cyclopenta[e]pyrazolo[1,5-a]pyrimidine derivatives as malt1 inhibitors |
| WO2025229494A1 (en) * | 2024-04-29 | 2025-11-06 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| CN119899194B (zh) * | 2025-03-31 | 2025-06-24 | 浙江省人民医院 | 双环杂芳基类braf负变构调节剂及其制备方法与应用 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009012283A1 (en) * | 2007-07-17 | 2009-01-22 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| WO2009111279A1 (en) * | 2008-02-29 | 2009-09-11 | Array Biopharma Inc. | Pyrazole [3, 4-b] pyridine raf inhibitors |
| WO2009137391A2 (en) * | 2008-05-06 | 2009-11-12 | Smithkline Beecham Corporation | Benzene sulfonamide thiazole and oxazole compounds |
| WO2011025938A2 (en) * | 2009-08-28 | 2011-03-03 | Array Biopharma Inc. | Raf inhibitor compounds and methods of use thereof |
| WO2011023773A1 (en) * | 2009-08-28 | 2011-03-03 | Novartis Ag | Compounds and compositions as protein kinase inhibitors |
| WO2011059610A1 (en) * | 2009-11-10 | 2011-05-19 | Glaxosmithkline Llc | Benzene sulfonamide thiazole and oxazole compounds |
| WO2013043935A1 (en) * | 2011-09-21 | 2013-03-28 | Neupharma, Inc. | Certain chemical entites, compositions, and methods |
| WO2014039714A2 (en) * | 2012-09-06 | 2014-03-13 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
Family Cites Families (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040171062A1 (en) | 2002-02-28 | 2004-09-02 | Plexxikon, Inc. | Methods for the design of molecular scaffolds and ligands |
| KR20120104412A (ko) | 2002-09-06 | 2012-09-20 | 인설트 테라페틱스, 인코퍼레이티드 | 공유결합된 치료제 전달을 위한 사이클로덱스트린-기초 중합체 |
| EP1558751A4 (en) | 2002-09-16 | 2007-08-22 | Plexxikon Inc | CRYSTALLINE STRUCTURE OF PROTEIN KINASE PIM-1 |
| US20050048573A1 (en) | 2003-02-03 | 2005-03-03 | Plexxikon, Inc. | PDE5A crystal structure and uses |
| JP2007524374A (ja) | 2003-02-28 | 2007-08-30 | プレキシコン，インコーポレーテッド | Ｐｙｋ２結晶構造および使用 |
| US20050079548A1 (en) | 2003-07-07 | 2005-04-14 | Plexxikon, Inc. | Ligand development using PDE4B crystal structures |
| WO2005009958A1 (en) | 2003-07-17 | 2005-02-03 | Plexxikon, Inc. | Ppar active compounds |
| US7348338B2 (en) | 2003-07-17 | 2008-03-25 | Plexxikon, Inc. | PPAR active compounds |
| US20050164300A1 (en) | 2003-09-15 | 2005-07-28 | Plexxikon, Inc. | Molecular scaffolds for kinase ligand development |
| US7504509B2 (en) | 2003-12-19 | 2009-03-17 | Plexxikon, Inc. | Compounds and methods for development of Ret modulators |
| US20070066641A1 (en) | 2003-12-19 | 2007-03-22 | Prabha Ibrahim | Compounds and methods for development of RET modulators |
| US7517970B2 (en) | 2003-12-19 | 2009-04-14 | Plexxikon, Inc. | Nucleic acids encoding kinase and phosphatase enzymes, expression vectors and cells containing same |
| CA2565965A1 (en) | 2004-05-06 | 2006-07-27 | Plexxikon, Inc. | Pde4b inhibitors and uses therefor |
| US20060058339A1 (en) | 2004-06-17 | 2006-03-16 | Ibrahim Prabha N | Compounds modulating c-kit activity and uses therefor |
| US7498342B2 (en) | 2004-06-17 | 2009-03-03 | Plexxikon, Inc. | Compounds modulating c-kit activity |
| CA2583428A1 (en) | 2004-09-03 | 2006-03-09 | Plexxikon, Inc. | Bicyclic heteroaryl pde4b inhibitors |
| CA2589896A1 (en) | 2004-11-30 | 2006-06-08 | Plexxikon, Inc. | Indole derivatives for use as ppar active compounds |
| AU2005311925A1 (en) | 2004-11-30 | 2006-06-08 | Plexxikon, Inc. | Indole derivatives for use as PPAR PPAR active compounds |
| US20060160135A1 (en) | 2004-12-08 | 2006-07-20 | Weiru Wang | SF-1 and LRH-1 modulator development |
| WO2007013896A2 (en) | 2005-05-17 | 2007-02-01 | Plexxikon, Inc. | Pyrrol (2,3-b) pyridine derivatives protein kinase inhibitors |
| TWI473808B (zh) | 2005-06-22 | 2015-02-21 | Plexxikon Inc | 用於激酶調節的化合物及方法及其適應症 |
| CN101304992A (zh) | 2005-09-07 | 2008-11-12 | 普莱希科公司 | 用作ppar调节剂的1,3-二取代吲哚衍生物 |
| JP2009507846A (ja) | 2005-09-07 | 2009-02-26 | プレキシコン，インコーポレーテッド | Ｐｐａｒ活性化合物 |
| US20080234349A1 (en) | 2005-09-07 | 2008-09-25 | Jack Lin | PPAR active compounds |
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| JP2010514695A (ja) | 2006-12-21 | 2010-05-06 | プレキシコン，インコーポレーテッド | キナーゼ調節のための化合物および方法およびそのための適応症 |
| WO2008079909A1 (en) | 2006-12-21 | 2008-07-03 | Plexxikon, Inc. | Pyrrolo [2,3-b] pyridines as kinase modulators |
| PE20121126A1 (es) | 2006-12-21 | 2012-08-24 | Plexxikon Inc | Compuestos pirrolo [2,3-b] piridinas como moduladores de quinasa |
| JP2010520303A (ja) | 2007-03-08 | 2010-06-10 | プレキシコン，インコーポレーテッド | Ｐｐａｒ活性化合物 |
| PE20090159A1 (es) | 2007-03-08 | 2009-02-21 | Plexxikon Inc | COMPUESTOS DERIVADOS DE ACIDO INDOL-PROPIONICO COMO MODULADORES PPARs |
| WO2009111278A2 (en) | 2008-02-29 | 2009-09-11 | Array Biopharma Inc. | Raf inhibitor compounds and methods of use thereof |
| WO2009143018A2 (en) | 2008-05-19 | 2009-11-26 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| PE20091846A1 (es) * | 2008-05-19 | 2009-12-16 | Plexxikon Inc | DERIVADOS DE PIRROLO[2,3-d]-PIRIMIDINA COMO MODULADORES DE CINASAS |
| CN104530052A (zh) | 2008-06-10 | 2015-04-22 | 普莱希科公司 | 用于激酶调节的5h-吡咯[2,3-b]吡嗪衍生物和其适应症 |
| WO2009152087A1 (en) | 2008-06-10 | 2009-12-17 | Plexxikon, Inc. | Bicyclic heteroaryl compounds and methods for kinase modulation, and indications therefor |
| KR101663339B1 (ko) | 2009-03-11 | 2016-10-06 | 플렉시콘 인코퍼레이티드 | Ｒａｆ 키나제의 억제를 위한 피롤로［２,３-ｂ］피리딘 유도체 |
| CN102421775A (zh) | 2009-03-11 | 2012-04-18 | 普莱希科公司 | 抑制Raf激酶的吡咯并[2，3-b]吡啶衍生物 |
| WO2010111527A1 (en) | 2009-03-26 | 2010-09-30 | Plexxikon, Inc. | Pyrazolo [ 3, 4 -b] pyridines as kinase inhibitors and their medical use |
| AU2010232670B2 (en) | 2009-04-03 | 2015-07-09 | F. Hoffmann-La Roche Ag | Propane- I-sulfonic acid {3- [5- (4 -chloro-phenyl) -1H-pyrrolo [2, 3-b] pyridine-3-carbonyl] -2, 4-difluoro-pheny l } -amide compositions and uses thereof |
| MX2011011735A (es) | 2009-05-04 | 2011-11-29 | Plexxikon Inc | Compuestos y metodos para la inhibicion de renina, e indicaciones para ello. |
| TW201041888A (en) | 2009-05-06 | 2010-12-01 | Plexxikon Inc | Compounds and methods for kinase modulation, and indications therefor |
| EP2470539A1 (en) | 2009-08-28 | 2012-07-04 | Array Biopharma, Inc. | Raf inhibitor compounds and methods of use thereof |
| EP2470538A1 (en) * | 2009-08-28 | 2012-07-04 | Array Biopharma, Inc. | Raf inhibitor compounds and methods of use thereof |
| AR077975A1 (es) * | 2009-08-28 | 2011-10-05 | Irm Llc | Derivados de pirazol pirimidina y composiciones como inhibidores de cinasa de proteina |
| MX2012005284A (es) | 2009-11-06 | 2012-06-28 | Plexxikon Inc | Compuestos y metodos para la modulacion de cinasas. e indicaciones para ello. |
| CN102740698A (zh) | 2009-11-18 | 2012-10-17 | 普莱希科公司 | 用于激酶调节的化合物和方法及其适应症 |
| BR112012015745A2 (pt) | 2009-12-23 | 2016-05-17 | Plexxikon Inc | compostos e métodos para a modulação de quinase, e indicações dos mesmos |
| TWI619713B (zh) | 2010-04-21 | 2018-04-01 | 普雷辛肯公司 | 用於激酶調節的化合物和方法及其適應症 |
| US8642606B2 (en) | 2010-09-29 | 2014-02-04 | Plexxikon Inc. | ZAP-70 active compounds |
| KR101911972B1 (ko) | 2011-02-07 | 2018-10-25 | 플렉시콘 인코퍼레이티드 | 키나제 조절을 위한 화합물 및 방법, 및 그에 대한 적응증 |
| TWI558702B (zh) | 2011-02-21 | 2016-11-21 | 普雷辛肯公司 | 醫藥活性物質的固態形式 |
| SG194847A1 (en) | 2011-05-17 | 2013-12-30 | Plexxikon Inc | Kinase modulation and indications therefor |
| US9358235B2 (en) | 2012-03-19 | 2016-06-07 | Plexxikon Inc. | Kinase modulation, and indications therefor |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| CA2895239C (en) | 2012-12-21 | 2020-10-27 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| US20140303121A1 (en) | 2013-03-15 | 2014-10-09 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| WO2014145051A1 (en) | 2013-03-15 | 2014-09-18 | Jiazhong Zhang | Heterocyclic compounds and uses thereof |
| BR112015028845A2 (pt) | 2013-05-30 | 2017-07-25 | Plexxikon Inc | compostos para a modulação da quinase e indicações da mesma |
| US9771369B2 (en) | 2014-03-04 | 2017-09-26 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| WO2016044067A1 (en) | 2014-09-15 | 2016-03-24 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| WO2016164641A1 (en) | 2015-04-08 | 2016-10-13 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| HRP20201383T1 (hr) | 2015-05-06 | 2020-11-27 | Plexxikon Inc. | Kruti oblici spoja za moduliranje kinaza |
| BR112017023540B1 (pt) | 2015-05-06 | 2023-04-04 | Plexxikon, Inc. | Processos de preparação de derivados de 1h-pirrolo[2,3-b]piridina que modulam quinases |
| WO2016191296A1 (en) | 2015-05-22 | 2016-12-01 | Plexxikon Inc. | Plx-8394 or plx-7904 for use in the treatment of braf-v600-related diseases |
| US10316032B2 (en) | 2015-05-22 | 2019-06-11 | Plexxikon Inc. | Solid forms of a compound for modulating kinases |
| WO2017019804A2 (en) | 2015-07-28 | 2017-02-02 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| EP3353179B1 (en) | 2015-09-21 | 2022-02-09 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| WO2017100201A1 (en) | 2015-12-07 | 2017-06-15 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| ES2904615T3 (es) | 2016-03-16 | 2022-04-05 | Plexxikon Inc | Compuestos y métodos para la modulación de quinasas e indicaciones al respecto |
| TW201815766A (zh) | 2016-09-22 | 2018-05-01 | 美商普雷辛肯公司 | 用於ｉｄｏ及ｔｄｏ調節之化合物及方法以及其適應症 |
| WO2018136202A2 (en) | 2016-12-23 | 2018-07-26 | Plexxikon Inc. | Compounds and methods for cdk8 modulation and indications therefor |
| CA3056777A1 (en) | 2017-03-20 | 2018-09-27 | Plexxikon Inc. | Crystalline forms of 4-(1-(1,1-di(pyridin-2-yl)ethyl)-6-(3,5-dimethylisoxazol-4-yl)-1h- pyrrolo[3,2-b]pyridin-3-yl)benzoic acid that inhibits bromodomain |
| WO2018226846A1 (en) | 2017-06-07 | 2018-12-13 | Plexxikon Inc. | Compounds and methods for kinase modulation |
-
2014
- 2014-05-29 BR BR112015028845A patent/BR112015028845A2/pt not_active IP Right Cessation
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-
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- 2015-11-23 PH PH12015502610A patent/PH12015502610A1/en unknown
-
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- 2017-12-11 US US15/838,268 patent/US10421761B2/en active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009012283A1 (en) * | 2007-07-17 | 2009-01-22 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| WO2009111279A1 (en) * | 2008-02-29 | 2009-09-11 | Array Biopharma Inc. | Pyrazole [3, 4-b] pyridine raf inhibitors |
| WO2009137391A2 (en) * | 2008-05-06 | 2009-11-12 | Smithkline Beecham Corporation | Benzene sulfonamide thiazole and oxazole compounds |
| WO2011025938A2 (en) * | 2009-08-28 | 2011-03-03 | Array Biopharma Inc. | Raf inhibitor compounds and methods of use thereof |
| WO2011023773A1 (en) * | 2009-08-28 | 2011-03-03 | Novartis Ag | Compounds and compositions as protein kinase inhibitors |
| WO2011059610A1 (en) * | 2009-11-10 | 2011-05-19 | Glaxosmithkline Llc | Benzene sulfonamide thiazole and oxazole compounds |
| WO2013043935A1 (en) * | 2011-09-21 | 2013-03-28 | Neupharma, Inc. | Certain chemical entites, compositions, and methods |
| WO2014039714A2 (en) * | 2012-09-06 | 2014-03-13 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
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| CN105228983A (zh) | 2016-01-06 |
| US10421761B2 (en) | 2019-09-24 |
| PH12015502610A1 (en) | 2016-02-29 |
| US20180099975A1 (en) | 2018-04-12 |
| BR112015028845A2 (pt) | 2017-07-25 |
| HK1219732A1 (zh) | 2017-04-13 |
| US20140357612A1 (en) | 2014-12-04 |
| CA2912568A1 (en) | 2014-12-04 |
| RU2015149937A (ru) | 2017-07-06 |
| MX2015015966A (es) | 2016-04-13 |
| AU2014274093A1 (en) | 2015-12-03 |
| KR20160013028A (ko) | 2016-02-03 |
| US9873700B2 (en) | 2018-01-23 |
| UY35596A (es) | 2014-12-31 |
| IL242587A0 (en) | 2016-02-01 |
| AR096450A1 (es) | 2015-12-30 |
| EP3004060A1 (en) | 2016-04-13 |
| JP2016520131A (ja) | 2016-07-11 |
| TW201533028A (zh) | 2015-09-01 |
| WO2014194127A1 (en) | 2014-12-04 |
| SG11201509338QA (en) | 2015-12-30 |
| EP3004060B1 (en) | 2019-11-27 |
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