KR101088922B1 - 사이클린 의존성 키나제 억제제로서의 피라졸로피리미딘 - Google Patents
사이클린 의존성 키나제 억제제로서의 피라졸로피리미딘 Download PDFInfo
- Publication number
- KR101088922B1 KR101088922B1 KR1020057003655A KR20057003655A KR101088922B1 KR 101088922 B1 KR101088922 B1 KR 101088922B1 KR 1020057003655 A KR1020057003655 A KR 1020057003655A KR 20057003655 A KR20057003655 A KR 20057003655A KR 101088922 B1 KR101088922 B1 KR 101088922B1
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- compound
- aryl
- heteroaryl
- cycloalkyl
- 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.)
- Expired - Lifetime
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- 0 Brc(cn[n]12)c1nc1N[C@](CCCC3)[C@]3**(Cc3cnccc3)c2c1 Chemical compound Brc(cn[n]12)c1nc1N[C@](CCCC3)[C@]3**(Cc3cnccc3)c2c1 0.000 description 19
- XETHRXRKOYUSND-UHFFFAOYSA-N Brc1c2nc(C3CNCCC3)cc(NCc3cnccc3)[n]2nc1 Chemical compound Brc1c2nc(C3CNCCC3)cc(NCc3cnccc3)[n]2nc1 XETHRXRKOYUSND-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N CNc1ccccc1 Chemical compound CNc1ccccc1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- IRYYCCGBUYXPGE-UHFFFAOYSA-N NC(N(CC1)CCC1c(cc(NCc1cccnc1)[n]1nc2)nc1c2Br)=N Chemical compound NC(N(CC1)CCC1c(cc(NCc1cccnc1)[n]1nc2)nc1c2Br)=N IRYYCCGBUYXPGE-UHFFFAOYSA-N 0.000 description 2
- TYOGLDHDTWIXHJ-UHFFFAOYSA-N NCCCCNc([n]1nc2)cc(-c(cccc3)c3Cl)nc1c2Br Chemical compound NCCCCNc([n]1nc2)cc(-c(cccc3)c3Cl)nc1c2Br TYOGLDHDTWIXHJ-UHFFFAOYSA-N 0.000 description 2
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- JQSIFAJCGCUSRC-UHFFFAOYSA-N Brc(cn[n]1c(NCc2cnccc2)c2)c1nc2-c1ccc[s]1 Chemical compound Brc(cn[n]1c(NCc2cnccc2)c2)c1nc2-c1ccc[s]1 JQSIFAJCGCUSRC-UHFFFAOYSA-N 0.000 description 1
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- AYIRWZMCUVMWQQ-KZUDCZAMSA-N O[C@@H](CCC1)C1Nc(cc(NCc1cnccc1)[n]1nc2)nc1c2Br Chemical compound O[C@@H](CCC1)C1Nc(cc(NCc1cnccc1)[n]1nc2)nc1c2Br AYIRWZMCUVMWQQ-KZUDCZAMSA-N 0.000 description 1
- AYIRWZMCUVMWQQ-ZIAGYGMSSA-N O[C@H](CCC1)[C@@H]1Nc(cc(NCc1cnccc1)[n]1nc2)nc1c2Br Chemical compound O[C@H](CCC1)[C@@H]1Nc(cc(NCc1cnccc1)[n]1nc2)nc1c2Br AYIRWZMCUVMWQQ-ZIAGYGMSSA-N 0.000 description 1
- AAMVNGZDBULSOF-UHFFFAOYSA-N O[n+]1cccc(CNc([n]2nc3)cc(C4CCCCC4)nc2c3Br)c1 Chemical compound O[n+]1cccc(CNc([n]2nc3)cc(C4CCCCC4)nc2c3Br)c1 AAMVNGZDBULSOF-UHFFFAOYSA-N 0.000 description 1
- ZWODLOOYWJZGKZ-UHFFFAOYSA-N [O-][n+]1cccc(CNc([n]2nc3)cc(-c(cccc4)c4Cl)nc2c3Br)c1 Chemical compound [O-][n+]1cccc(CNc([n]2nc3)cc(-c(cccc4)c4Cl)nc2c3Br)c1 ZWODLOOYWJZGKZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Virology (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40802702P | 2002-09-04 | 2002-09-04 | |
| US60/408,027 | 2002-09-04 | ||
| US42195902P | 2002-10-29 | 2002-10-29 | |
| US60/421,959 | 2002-10-29 | ||
| PCT/US2003/027555 WO2004022561A1 (en) | 2002-09-04 | 2003-09-03 | Pyrazolopyrimidines as cyclin-dependent kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20050057120A KR20050057120A (ko) | 2005-06-16 |
| KR101088922B1 true KR101088922B1 (ko) | 2011-12-01 |
Family
ID=42828922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057003655A Expired - Lifetime KR101088922B1 (ko) | 2002-09-04 | 2003-09-03 | 사이클린 의존성 키나제 억제제로서의 피라졸로피리미딘 |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1537116B1 (https=) |
| JP (1) | JP4881558B2 (https=) |
| KR (1) | KR101088922B1 (https=) |
| AT (1) | ATE469903T1 (https=) |
| AU (1) | AU2003263071B2 (https=) |
| BR (1) | BRPI0314001B8 (https=) |
| CA (1) | CA2497440C (https=) |
| DK (1) | DK1537116T3 (https=) |
| IL (1) | IL167086A (https=) |
| MX (1) | MXPA05002571A (https=) |
| NO (1) | NO20051647L (https=) |
| NZ (1) | NZ539165A (https=) |
| WO (1) | WO2004022561A1 (https=) |
Families Citing this family (118)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7563798B2 (en) * | 2002-09-04 | 2009-07-21 | Schering Corporation | Substituted pyrazolo[1,5-a]pyrimidines as protein kinase inhibitors |
| US7605155B2 (en) * | 2002-09-04 | 2009-10-20 | Schering Corporation | Substituted pyrazolo[1,5-a]pyrimidines as protein kinase inhibitors |
| US7119200B2 (en) * | 2002-09-04 | 2006-10-10 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| US7601724B2 (en) * | 2002-09-04 | 2009-10-13 | Schering Corporation | Substituted pyrazolo[1,5-a]pyrimidines as protein kinase inhibitors |
| CA2497444C (en) * | 2002-09-04 | 2010-11-30 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| US7196078B2 (en) * | 2002-09-04 | 2007-03-27 | Schering Corpoartion | Trisubstituted and tetrasubstituted pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| JP4564485B2 (ja) * | 2003-02-28 | 2010-10-20 | 帝人ファーマ株式会社 | ピラゾロ[1,5−a]ピリミジン誘導体 |
| GB0305559D0 (en) * | 2003-03-11 | 2003-04-16 | Teijin Ltd | Compounds |
| US20070179161A1 (en) * | 2003-03-31 | 2007-08-02 | Vernalis (Cambridge) Limited. | Pyrazolopyrimidine compounds and their use in medicine |
| ES2300672T3 (es) * | 2003-04-30 | 2008-06-16 | Merck Patent Gmbh | Derivados de cromenona. |
| MXPA06002618A (es) * | 2003-09-09 | 2006-06-05 | Ono Pharmaceutical Co | Antagonistas del factor de liberacion de corticotropina (crf) y compuestos heterobiciclicos. |
| JP2007533749A (ja) * | 2004-04-20 | 2007-11-22 | アムゲン インコーポレイティッド | アリールスルホンアミドおよびそれに関連する使用方法 |
| GB0412553D0 (en) * | 2004-06-04 | 2004-07-07 | Univ Aberdeen | Therapeutic agents for the treatment of bone conditions |
| JP5080970B2 (ja) | 2004-06-17 | 2012-11-21 | サイトキネティクス・インコーポレーテッド | 心疾患を治療するための置換尿素誘導体 |
| US7667036B2 (en) | 2004-08-13 | 2010-02-23 | Teijin Pharma Limited | Pyrazolo[1,5-a]pyrimidine derivatives |
| EP1780212A4 (en) * | 2004-08-13 | 2008-10-22 | Teijin Pharma Ltd | DERIVATIVE OF PYRAZOLO [1,5-a] PYRIMIDINE |
| AU2005281704A1 (en) | 2004-09-06 | 2006-03-16 | Nycomed Gmbh | Novel pyrazolopyrimidines |
| GB0515026D0 (en) * | 2005-07-21 | 2005-08-31 | Novartis Ag | Organic compounds |
| WO2007017678A1 (en) * | 2005-08-09 | 2007-02-15 | Eirx Therapeutics Limited | Pyrazolo[1,5-a] pyrimidine compounds and pharmaceutical compositions containing them |
| EP1928437A2 (en) | 2005-08-26 | 2008-06-11 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| CA2621983A1 (en) | 2005-09-09 | 2007-03-22 | Schering Corporation | Azafused cyclin dependent kinase inhibitors |
| CN101321760A (zh) * | 2005-10-06 | 2008-12-10 | 先灵公司 | 作为蛋白激酶抑制剂的吡唑并嘧啶 |
| US20070082900A1 (en) * | 2005-10-06 | 2007-04-12 | Schering Corporation | Methods for inhibiting protein kinases |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| US20070112017A1 (en) | 2005-10-31 | 2007-05-17 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| TW200808321A (en) | 2005-12-15 | 2008-02-16 | Cytokinetics Inc | Certain chemical entities, compositions and methods |
| US7825120B2 (en) * | 2005-12-15 | 2010-11-02 | Cytokinetics, Inc. | Certain substituted ((piperazin-1-ylmethyl)benzyl)ureas |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| AU2007249399A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| BRPI0712016A2 (pt) * | 2006-05-22 | 2011-12-27 | Schering Corp | pirazolo[1,5-a]pirimidinas |
| CA2660953A1 (en) * | 2006-08-18 | 2008-02-21 | Schering Corporation | Process for resolving chiral piperidine alcohol and process for synthesis of pyrazolo [1,5-a] pyrimidine derivatives using same |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| AU2007312390B2 (en) | 2006-10-19 | 2013-03-28 | F. Hoffmann-La Roche Ag | Aminomethyl-4-imidazoles |
| DE102007012645A1 (de) * | 2007-03-16 | 2008-09-18 | Bayer Healthcare Ag | Substituierte Imidazo- und Triazolopyrimidine |
| GB0705400D0 (en) | 2007-03-21 | 2007-05-02 | Univ Aberdeen | Therapeutic compounds andm their use |
| DE102007032349A1 (de) * | 2007-07-11 | 2009-01-15 | Bayer Healthcare Ag | Imidazo-, Pyrazolopyrazine und Imidazotriazine und ihre Verwendung |
| US20110009429A1 (en) * | 2008-02-26 | 2011-01-13 | Paul Oakley | Heterocyclic compounds as inhibitors of cxcr2 |
| TW200944526A (en) * | 2008-04-22 | 2009-11-01 | Vitae Pharmaceuticals Inc | Carbamate and urea inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| ES2522346T3 (es) | 2008-08-22 | 2014-11-14 | Novartis Ag | Compuestos de pirrolopirimidina como inhibidores de CDK |
| GB0817207D0 (en) | 2008-09-19 | 2008-10-29 | Pimco 2664 Ltd | therapeutic apsac compounds and their use |
| GB0817208D0 (en) | 2008-09-19 | 2008-10-29 | Pimco 2664 Ltd | Therapeutic apsap compounds and their use |
| PT2350075E (pt) | 2008-09-22 | 2014-06-09 | Array Biopharma Inc | Compostos imidazo[1,2b]piridazina substituídos como inibidores da trk cinase |
| AR074052A1 (es) | 2008-10-22 | 2010-12-22 | Array Biopharma Inc | Compuestos pirazolo{1,5-a}pirimidina sustituida como inhibidores de trk cinasa |
| WO2010080864A1 (en) * | 2009-01-12 | 2010-07-15 | Array Biopharma Inc. | Piperidine-containing compounds and use thereof |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| US8591943B2 (en) | 2009-04-09 | 2013-11-26 | Merck Sharp & Dohme Corp. | Pyrazolo[1,5-a]pyrimidine derivatives as mTOR inhibitors |
| AR077468A1 (es) | 2009-07-09 | 2011-08-31 | Array Biopharma Inc | Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa |
| US20110071115A1 (en) * | 2009-09-11 | 2011-03-24 | Cylene Pharmaceuticals, Inc. | Pharmaceutically useful heterocycle-substituted lactams |
| US9180127B2 (en) | 2009-12-29 | 2015-11-10 | Dana-Farber Cancer Institute, Inc. | Type II Raf kinase inhibitors |
| US9227971B2 (en) | 2010-01-19 | 2016-01-05 | Merck Sharp & Dohme Corp. | Pyrazolo[1,5-a]pyrimidine compounds as mTOR inhibitors |
| WO2011094953A1 (en) * | 2010-02-08 | 2011-08-11 | F. Hoffmann-La Roche Ag | Compounds for the treatment and prevention of influenza |
| AR081331A1 (es) * | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| US9133123B2 (en) | 2010-04-23 | 2015-09-15 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| NZ604708A (en) | 2010-05-20 | 2015-05-29 | Array Biopharma Inc | Macrocyclic compounds as trk kinase inhibitors |
| JP6007417B2 (ja) | 2011-05-31 | 2016-10-12 | レセプトス エルエルシー | 新規glp−1受容体安定剤および調節剤 |
| WO2012178125A1 (en) | 2011-06-22 | 2012-12-27 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| WO2013012915A1 (en) | 2011-07-19 | 2013-01-24 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| CA2856291C (en) | 2011-11-17 | 2020-08-11 | Dana-Farber Cancer Institute, Inc. | Inhibitors of c-jun-n-terminal kinase (jnk) |
| WO2013144532A1 (en) * | 2012-03-30 | 2013-10-03 | Astrazeneca Ab | 3 -cyano- 5 -arylamino-7 -cycloalkylaminopyrrolo [1, 5 -a] pyrimidine derivatives and their use as antitumor agents |
| US9758522B2 (en) | 2012-10-19 | 2017-09-12 | Dana-Farber Cancer Institute, Inc. | Hydrophobically tagged small molecules as inducers of protein degradation |
| US9573954B2 (en) | 2012-11-16 | 2017-02-21 | University Health Network | Pyrazolopyrimidine compounds |
| SI2941432T1 (en) | 2012-12-07 | 2018-07-31 | Vertex Pharmaceuticals Incorporated | 2-AMINO-6-FLUORO-N- (5-FLUORO-4- (4- (4- (OXETHAN-3-YL) PIPERAZIN-1-CARBONYL) PIPERIDIN-1-YLIPRIDIN-3-YL) 1,5 ALFA) PYRIMIDINE-3-CARBOXAMIDE AS ATR KINAZE INHIBITOR |
| CA2896731A1 (en) | 2012-12-28 | 2014-07-03 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Inhibitors of the usp1/uaf1 deubiquitinase complex and uses thereof |
| JP2016512815A (ja) | 2013-03-15 | 2016-05-09 | バーテックス ファーマシューティカルズ インコーポレイテッドVertex Pharmaceuticals Incorporated | Atrキナーゼの阻害剤として有用な縮合ピラゾロピリミジン誘導体 |
| EP2970289A1 (en) | 2013-03-15 | 2016-01-20 | Vertex Pharmaceuticals Inc. | Compounds useful as inhibitors of atr kinase |
| WO2014143242A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| CN109867630A (zh) | 2013-06-11 | 2019-06-11 | 赛尔基因第二国际有限公司 | 新型glp-1受体调节剂 |
| GB201311361D0 (en) | 2013-06-26 | 2013-08-14 | Pimco 2664 Ltd | Compounds and their therapeutic use |
| KR102529049B1 (ko) | 2013-08-14 | 2023-05-08 | 노파르티스 아게 | 암의 치료를 위한 조합 요법 |
| US10047070B2 (en) | 2013-10-18 | 2018-08-14 | Dana-Farber Cancer Institute, Inc. | Polycyclic inhibitors of cyclin-dependent kinase 7 (CDK7) |
| EP3057955B1 (en) | 2013-10-18 | 2018-04-11 | Syros Pharmaceuticals, Inc. | Heteroaromatic compounds useful for the treatment of prolferative diseases |
| DK3077397T3 (da) | 2013-12-06 | 2019-12-16 | Vertex Pharma | 2-amino-6-fluor-n-[5-fluor-pyridin-3-yl]pyrazolo[1,5-a]pyrimidin-3-carboxamidforbindelse anvendelig som atr-kinase-inhibitor, dens fremstilling, forskellige faste former og radiomarkerede derivater deraf |
| GB201403093D0 (en) | 2014-02-21 | 2014-04-09 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| CN106458990B (zh) | 2014-04-04 | 2019-06-07 | 希洛斯医药品股份有限公司 | 细胞周期蛋白依赖性激酶7(cdk7)的抑制剂 |
| EP3129371B1 (en) * | 2014-04-05 | 2020-07-29 | Syros Pharmaceuticals, Inc. | Inhibitors of cyclin-dependent kinase 7 (cdk7) |
| PL3152212T3 (pl) | 2014-06-05 | 2020-06-15 | Vertex Pharmaceuticals Inc. | Radioznakowane pochodne związku 2-amino-6-fluoro-n-[5-fluoro-piridyn-3-ylo]-pirazolo[1,5-a]pirymidino-3-karboksamidu przydatne jako inhibitor kinazy atr, wytwarzanie tego związku i jego różnych postaci stałych |
| LT3157566T (lt) | 2014-06-17 | 2019-08-12 | Vertex Pharmaceuticals Incorporated | Vėžio gydymo būdas, panaudojant chk1 ir atr inhibitorių derinį |
| HUE061448T2 (hu) | 2014-11-16 | 2023-07-28 | Array Biopharma Inc | (S)-N-(5-((R)-2-(2,5-difluorofenil)-pirrolidin-1-il)-pirazolo[1,5-A]pirimidin-3-il) -3-hidroxipirrolidin-1-karboxamid-hidrogénszulfát kristályos formája |
| AU2015360364B2 (en) | 2014-12-10 | 2020-04-30 | Receptos Llc | GLP-1 receptor modulators |
| SI3262028T1 (sl) | 2014-12-17 | 2022-02-28 | Pimco 2664 Limited | N-(4-hidroksi-4-metil-cikloheksil)-4-fenil-benzensulfonamidne in N-(-4hidroksi-4-metil-cikloheksil)-4-(2-piridil)-benzensulfonamidne spojine in njihova terapevtska uporaba |
| AU2015371251B2 (en) | 2014-12-23 | 2020-06-11 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 (CDK7) |
| HK1246645A1 (zh) * | 2015-03-27 | 2018-09-14 | 达纳-法伯癌症研究所股份有限公司 | 细胞周期蛋白依赖性激酶的抑制剂 |
| US10702527B2 (en) | 2015-06-12 | 2020-07-07 | Dana-Farber Cancer Institute, Inc. | Combination therapy of transcription inhibitors and kinase inhibitors |
| EP3347018B1 (en) | 2015-09-09 | 2021-09-01 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| GB201517263D0 (en) * | 2015-09-30 | 2015-11-11 | Ucb Biopharma Sprl And Katholieke Universiteit Leuven | Therapeutic agents |
| HK1258570A1 (zh) | 2015-09-30 | 2019-11-15 | Vertex Pharmaceuticals Inc. | 使用dna损伤剂及atr抑制剂的组合治疗癌症的方法 |
| CN108697708A (zh) | 2015-10-26 | 2018-10-23 | 洛克索肿瘤学股份有限公司 | Trk抑制剂抗性癌症中的点突变以及与此相关的方法 |
| US10045991B2 (en) | 2016-04-04 | 2018-08-14 | Loxo Oncology, Inc. | Methods of treating pediatric cancers |
| ES2987474T3 (es) | 2016-04-04 | 2024-11-15 | Loxo Oncology Inc | Formulaciones líquidas de (S)-N-(5-((R)-2-(2,5-difluorofenil)-pirrolidin-1-IL)-pirazolo[1,5-A]pirimidin-3-IL)-3-hidroxipirrolidina-1-carboxamida |
| ES2836222T3 (es) | 2016-05-18 | 2021-06-24 | Loxo Oncology Inc | Preparación de (S)-N-(5-((R)-2-(2,5-difluorofenil)pirrolidin-1-il)pirazolo[1,5-a]pirimidin-3-il)-3-hidroxipirrolidina-1-carboxamida |
| AU2017311691B2 (en) | 2016-08-18 | 2021-12-02 | Vidac Pharma Ltd. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
| JOP20190092A1 (ar) | 2016-10-26 | 2019-04-25 | Array Biopharma Inc | عملية لتحضير مركبات بيرازولو[1، 5-a]بيريميدين وأملاح منها |
| CN108017641B (zh) * | 2016-11-02 | 2021-01-05 | 深圳铂立健医药有限公司 | 吡唑并嘧啶化合物作为pi3k抑制剂及其应用 |
| WO2018082444A1 (zh) * | 2016-11-02 | 2018-05-11 | 叶宝欢 | 吡唑并嘧啶化合物作为pi3k抑制剂及其应用 |
| WO2018154133A1 (en) * | 2017-02-27 | 2018-08-30 | Janssen Pharmaceutica Nv | [1,2,4]-triazolo [1,5-a]-pyrimidinyl derivatives substituted with piperidine, morpholine or piperazine as oga inhibitors |
| JOP20190213A1 (ar) | 2017-03-16 | 2019-09-16 | Array Biopharma Inc | مركبات حلقية ضخمة كمثبطات لكيناز ros1 |
| PL233595B1 (pl) * | 2017-05-12 | 2019-11-29 | Celon Pharma Spolka Akcyjna | Pochodne pirazolo[1,5-a]pirymidyny jako inhibitory kinazy JAK |
| KR102717819B1 (ko) | 2017-07-28 | 2024-10-14 | 다케다 야쿠힌 고교 가부시키가이샤 | Tyk2 억제제 및 이의 용도 |
| GB201715194D0 (en) | 2017-09-20 | 2017-11-01 | Carrick Therapeutics Ltd | Compounds and their therapeutic use |
| USRE50663E1 (en) | 2017-10-04 | 2025-11-18 | Bayer Aktiengesellschaft | Heterocycle derivatives as pesticides |
| IL276013B2 (en) | 2018-01-17 | 2024-03-01 | Glaxosmithkline Ip Dev Ltd | Pi4kiiibeta inhibitors |
| KR20200131268A (ko) | 2018-03-12 | 2020-11-23 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 융합된 비시클릭 헤테로시클릭 유도체 |
| AU2019254499A1 (en) | 2018-04-20 | 2020-12-03 | Bayer Aktiengesellschaft | Heterocyclene derivatives as pest control agents |
| US12187701B2 (en) | 2018-06-25 | 2025-01-07 | Dana-Farber Cancer Institute, Inc. | Taire family kinase inhibitors and uses thereof |
| JP7179161B2 (ja) | 2018-09-10 | 2022-11-28 | イーライ リリー アンド カンパニー | 乾癬および全身性エリテマトーデスの処置に有用なピラゾロ[1,5-a]ピリミジン-3-カルボキサミド誘導体 |
| AU2019370200B2 (en) * | 2018-10-30 | 2024-12-19 | Kronos Bio, Inc. | Compounds, compositions, and methods for modulating CDK9 activity |
| TWI800696B (zh) | 2018-12-10 | 2023-05-01 | 美商美國禮來大藥廠 | 7-(甲基胺基)吡唑并[1,5-a]嘧啶-3-甲醯胺衍生物 |
| GB201918541D0 (en) | 2019-12-16 | 2020-01-29 | Carrick Therapeutics Ltd | Therapeutic compounds and their use |
| WO2021162944A1 (en) | 2020-02-12 | 2021-08-19 | Eli Lilly And Company | Substituted 7-(methylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide derivatives |
| TWI810520B (zh) | 2020-02-12 | 2023-08-01 | 美商美國禮來大藥廠 | 7-(甲基胺基)吡唑并[1,5-a]嘧啶-3-甲醯胺化合物 |
| WO2022187518A1 (en) * | 2021-03-03 | 2022-09-09 | Ikena Oncology, Inc. | Substituted 4-piperidinyl-imidazo[4,5-b]pyridines and related compounds and their use in treating medical conditions |
| AU2022271290A1 (en) | 2021-05-07 | 2023-11-23 | Kymera Therapeutics, Inc. | Cdk2 degraders and uses thereof |
| GB202108572D0 (en) * | 2021-06-16 | 2021-07-28 | Carrick Therapeutics Ltd | Therapeutic compounds and their use |
| WO2024054602A1 (en) * | 2022-09-08 | 2024-03-14 | Halda Therapeutics Opco, Inc. | Heterobifunctional compounds and methods of treating disease |
| TW202543650A (zh) | 2024-03-08 | 2025-11-16 | 美商海爾達醫療運營公司 | 異雙官能化合物及其在治療疾病中之用途 |
| WO2026057043A1 (zh) * | 2024-09-14 | 2026-03-19 | 正大天晴药业集团股份有限公司 | 作为cdk抑制剂的三并环化合物及其应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002050079A1 (fr) | 2000-12-20 | 2002-06-27 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Inhibiteurs de kinases dependantes des cylines (cdk) et de la glycogene synthase kinase-3 (gsk-3) |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792533A (fr) * | 1971-12-09 | 1973-06-08 | Int Chem & Nuclear Corp | Nouvelles pyrazolo (1,5a) pyrimidines et leur procede de preparation |
| JPS57140870A (en) * | 1981-11-09 | 1982-08-31 | Canon Inc | Controlling apparatus for concentration of plating solution |
| JPS6157587A (ja) * | 1984-08-29 | 1986-03-24 | Shionogi & Co Ltd | 縮合複素環誘導体および抗潰瘍剤 |
| EP0628559B1 (en) * | 1993-06-10 | 2002-04-03 | Beiersdorf-Lilly GmbH | Pyrimidine compounds and their use as pharmaceuticals |
| ATE355841T1 (de) * | 1997-12-13 | 2007-03-15 | Bristol Myers Squibb Co | Verwendung von pyrazolo ( 3,4-b) pyridin als cyclin-abhängige kinase hemmer |
| US6413974B1 (en) * | 1998-02-26 | 2002-07-02 | Aventis Pharmaceuticals Inc. | 6,9,-disubstituted 2-[trans-(4-aminocyclohexyl) amino] purines |
| FR2805160B1 (fr) * | 2000-02-23 | 2002-04-05 | Oreal | Compositions pour la teinture d'oxydation des fibres keratiniques comprenant un n(2-hydroxybenzene)-carbramate ou un n-(2-hydroxybenzene)-uree et une pyrazolopyrimidine, et procedes de teinture |
| ATE335737T1 (de) | 2000-09-15 | 2006-09-15 | Vertex Pharma | Isoxazole und ihre verwendung als erk-inhibitoren |
| FR2817469B1 (fr) * | 2000-12-04 | 2003-04-18 | Oreal | Composition de coloration, procede d'obtention et utilisation pour la coloration de fibres keratiniques |
| CA2497444C (en) * | 2002-09-04 | 2010-11-30 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| JP2004277337A (ja) * | 2003-03-14 | 2004-10-07 | Sumitomo Pharmaceut Co Ltd | ピラゾロ[1,5−a]ピリミジン誘導体 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2002050079A1 (fr) | 2000-12-20 | 2002-06-27 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Inhibiteurs de kinases dependantes des cylines (cdk) et de la glycogene synthase kinase-3 (gsk-3) |
Also Published As
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|---|---|
| EP1537116B1 (en) | 2010-06-02 |
| ATE469903T1 (de) | 2010-06-15 |
| CA2497440A1 (en) | 2004-03-18 |
| HK1071756A1 (en) | 2005-07-29 |
| EP1537116A1 (en) | 2005-06-08 |
| KR20050057120A (ko) | 2005-06-16 |
| JP4881558B2 (ja) | 2012-02-22 |
| AU2003263071A1 (en) | 2004-03-29 |
| CA2497440C (en) | 2011-03-22 |
| BRPI0314001B1 (pt) | 2018-10-23 |
| AU2003263071B2 (en) | 2007-03-15 |
| NO20051647L (no) | 2005-06-03 |
| JP2006502163A (ja) | 2006-01-19 |
| WO2004022561A1 (en) | 2004-03-18 |
| NZ539165A (en) | 2008-03-28 |
| IL167086A (en) | 2015-01-29 |
| BR0314001A (pt) | 2005-07-05 |
| BRPI0314001B8 (pt) | 2021-05-25 |
| MXPA05002571A (es) | 2005-09-08 |
| DK1537116T3 (da) | 2010-09-27 |
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