ZA200501851B - Pyrazolopyrimidines as cyclin dependent kinase inhibitors. - Google Patents
Pyrazolopyrimidines as cyclin dependent kinase inhibitors. Download PDFInfo
- Publication number
- ZA200501851B ZA200501851B ZA200501851A ZA200501851A ZA200501851B ZA 200501851 B ZA200501851 B ZA 200501851B ZA 200501851 A ZA200501851 A ZA 200501851A ZA 200501851 A ZA200501851 A ZA 200501851A ZA 200501851 B ZA200501851 B ZA 200501851B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- cycloalkyl
- group
- alkyl
- aryl
- Prior art date
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- 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 title description 7
- APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title description 3
- 239000002875 cyclin dependent kinase inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- -1 -C(O)OR? Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 102000003903 Cyclin-dependent kinases Human genes 0.000 claims description 18
- 108090000266 Cyclin-dependent kinases Proteins 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 108091007914 CDKs Proteins 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 229910006069 SO3H Inorganic materials 0.000 claims description 4
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- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
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- 210000002307 prostate Anatomy 0.000 claims description 3
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 3
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
- 125000005038 alkynylalkyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
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- BIIVYFLTOXDAOV-YVEFUNNKSA-N alvocidib Chemical compound O[C@@H]1CN(C)CC[C@@H]1C1=C(O)C=C(O)C2=C1OC(C=1C(=CC=CC=1)Cl)=CC2=O BIIVYFLTOXDAOV-YVEFUNNKSA-N 0.000 description 1
- 230000006369 cell cycle progression Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 230000003081 coactivator Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- MWEQTWJABOLLOS-UHFFFAOYSA-L disodium;[[[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-oxidophosphoryl] hydrogen phosphate;trihydrate Chemical compound O.O.O.[Na+].[Na+].C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP([O-])(=O)OP(O)([O-])=O)C(O)C1O MWEQTWJABOLLOS-UHFFFAOYSA-L 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- GTVPOLSIJWJJNY-UHFFFAOYSA-N olomoucine Chemical compound N1=C(NCCO)N=C2N(C)C=NC2=C1NCC1=CC=CC=C1 GTVPOLSIJWJJNY-UHFFFAOYSA-N 0.000 description 1
- 230000006508 oncogene activation Effects 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000016596 traversing start control point of mitotic cell cycle Effects 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-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
- 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
- A61K31/495—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
-
- 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
- A61P31/10—Antimycotics
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Virology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40803002P | 2002-09-04 | 2002-09-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200501851B true ZA200501851B (en) | 2005-09-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200501851A ZA200501851B (en) | 2002-09-04 | 2005-03-03 | Pyrazolopyrimidines as cyclin dependent kinase inhibitors. |
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| EP (1) | EP1534709B1 (enExample) |
| JP (2) | JP2006501260A (enExample) |
| KR (1) | KR20050058507A (enExample) |
| CN (1) | CN1310918C (enExample) |
| AR (1) | AR041134A1 (enExample) |
| AT (1) | ATE364608T1 (enExample) |
| CA (1) | CA2497444C (enExample) |
| DE (1) | DE60314427T2 (enExample) |
| ES (1) | ES2285164T3 (enExample) |
| MX (1) | MXPA05002573A (enExample) |
| MY (1) | MY139336A (enExample) |
| NZ (1) | NZ539162A (enExample) |
| PE (1) | PE20041076A1 (enExample) |
| TW (1) | TW200413377A (enExample) |
| WO (1) | WO2004022559A1 (enExample) |
| ZA (1) | ZA200501851B (enExample) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0977563B1 (en) | 1996-12-03 | 2005-10-12 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
| US20020058286A1 (en) * | 1999-02-24 | 2002-05-16 | Danishefsky Samuel J. | Synthesis of epothilones, intermediates thereto and analogues thereof |
| WO2004018478A2 (en) | 2002-08-23 | 2004-03-04 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
| US6921769B2 (en) | 2002-08-23 | 2005-07-26 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| US7649006B2 (en) | 2002-08-23 | 2010-01-19 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| US7119200B2 (en) * | 2002-09-04 | 2006-10-10 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| DE60313872T2 (de) | 2002-09-04 | 2008-01-17 | Schering Corp. | Pyrazoloä1,5-aüpyrimidine als hemmstoffe cyclin-abhängiger kinasen |
| US7196092B2 (en) * | 2002-09-04 | 2007-03-27 | Schering Corporation | N-heteroaryl pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| US7205308B2 (en) * | 2002-09-04 | 2007-04-17 | Schering Corporation | Trisubstituted 7-aminopyrazolopyrimidines as cyclin dependent kinase inhibitors |
| EP1537116B1 (en) * | 2002-09-04 | 2010-06-02 | Schering Corporation | Pyrazolopyrimidines suitable for the treatment of cancer diseases |
| NZ539162A (en) * | 2002-09-04 | 2006-07-28 | Schering Corp | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| 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 |
| MXPA05008955A (es) | 2003-02-28 | 2006-02-22 | Teijin Pharma Ltd | Derivados de pirazolo [1,5-a] pirimidina. |
| GB0305559D0 (en) * | 2003-03-11 | 2003-04-16 | Teijin Ltd | Compounds |
| EP1608652A1 (en) * | 2003-03-31 | 2005-12-28 | Vernalis (Cambridge) Limited | Pyrazolopyrimidine compounds and their use in medicine |
| US20070275961A1 (en) * | 2003-06-04 | 2007-11-29 | Vernalis (Cambridge) Limited. | Triazolo ' 1, 5-A ! Pyrimidines and Their Use in Medicine |
| EP1666468A4 (en) * | 2003-09-09 | 2007-03-21 | Ono Pharmaceutical Co | CRF ANTAGONISTS AND HETEROBICYCLIC COMPOUNDS |
| US8071603B2 (en) | 2004-09-20 | 2011-12-06 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| TW200626138A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
| MX2007003319A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
| CA2580857A1 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| MX2007003318A (es) | 2004-09-20 | 2007-05-18 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
| CN101084212A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为硬脂酰CoA去饱和酶介导剂的用途 |
| CA2580855A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| EP2029138A1 (en) | 2005-06-03 | 2009-03-04 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| CA2621983A1 (en) | 2005-09-09 | 2007-03-22 | Schering Corporation | Azafused cyclin dependent kinase inhibitors |
| WO2007044426A2 (en) * | 2005-10-06 | 2007-04-19 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
| TWI421078B (zh) * | 2005-10-06 | 2014-01-01 | Merck Sharp & Dohme | 關卡激酶抑制劑及其用途 |
| TWI403320B (zh) | 2005-12-16 | 2013-08-01 | Infinity Discovery Inc | 用於抑制ｂｃｌ蛋白和結合夥伴間之交互作用的化合物及方法 |
| US8008307B2 (en) | 2006-08-08 | 2011-08-30 | Millennium Pharmaceuticals, Inc. | Heteroaryl compounds useful as inhibitors of E1 activating enzymes |
| GB0704652D0 (en) * | 2007-03-09 | 2007-04-18 | Syngenta Participations Ag | Novel herbicides |
| CA2689667A1 (en) * | 2007-06-07 | 2008-12-18 | Schering Corporation | Synthesis of substituted-3-aminopyrazoles |
| DE102008022221A1 (de) * | 2008-05-06 | 2009-11-12 | Universität des Saarlandes | Inhibitoren der humanen Aldosteronsynthase CYP11B2 |
| UY32395A (es) | 2009-01-27 | 2010-08-31 | Takeda Pharmaceutical | Compuesto con anillo fusionado y su uso |
| US8993535B2 (en) | 2009-09-04 | 2015-03-31 | Merck Sharp & Dohme Corp. | Modulators of cell cycle checkpoints and their use in combination with checkpoint kinase inhibitors |
| US10953012B2 (en) | 2011-04-26 | 2021-03-23 | Bioenergenix Llc | Heterocyclic compounds for the inhibition of pask |
| EP2723746A1 (en) | 2011-06-22 | 2014-04-30 | Vertex Pharmaceuticals Inc. | Compounds useful as inhibitors of atr kinase |
| UA116534C2 (uk) | 2012-02-17 | 2018-04-10 | Мілленніум Фармасьютікалз, Інк. | Піразолопіримідинілові інгібітори убіквітинактивуючого ферменту |
| WO2014066795A1 (en) | 2012-10-25 | 2014-05-01 | Bioenergenix | Heterocyclic compounds for the inhibition of pask |
| WO2014066743A1 (en) | 2012-10-25 | 2014-05-01 | Bioenergenix | Heterocyclic compounds for the inhibition of pask |
| AU2013344716B2 (en) | 2012-11-16 | 2018-03-01 | University Health Network | Pyrazolopyrimidine compounds |
| BR112015012454B1 (pt) | 2012-12-07 | 2022-07-05 | Vertex Pharmaceuticals Incorporated | Compostos inibidores de atr quinase, seu uso e composição farmacêutica compreendendo os mesmos |
| US10035801B2 (en) | 2013-03-13 | 2018-07-31 | Genentech, Inc. | Pyrazolo compounds and uses thereof |
| WO2014143242A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| WO2014143240A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Fused pyrazolopyrimidine derivatives useful as inhibitors of atr kinase |
| WO2014143241A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| CA2916468C (en) | 2013-07-02 | 2019-07-23 | Millennium Pharmaceuticals, Inc. | Heteroaryl compounds useful as inhibitors of sumo activating enzyme |
| ES2768678T3 (es) | 2013-12-06 | 2020-06-23 | Vertex Pharma | Compuesto de 2-amino-6-fluoro-N-[5-fluoro-piridin-3-il]pirazolo[1,5-a]pirimidin-3-carboxamida útil como inhibidor de la ATR quinasa, su preparación, diferentes formas sólidas y derivados radiomarcados de las mismas |
| ES2777608T3 (es) | 2014-06-05 | 2020-08-05 | Vertex Pharma | Derivados radiomarcados de un compuesto de 2-amino-6-fluoro-N-[5-fluoro-piridin-3-il]-pirazolo[1,5-a]pirimidin-3-carboxamida útiles como inhibidores de ATR cinasa, la preparación de dicho compuesto y diferentes formas sólidas del mismo |
| KR20170016498A (ko) | 2014-06-17 | 2017-02-13 | 버텍스 파마슈티칼스 인코포레이티드 | Chk1 및 atr 저해제의 병용물을 사용하는 암의 치료 방법 |
| NZ728162A (en) | 2014-07-01 | 2023-06-30 | Takeda Pharmaceuticals Co | Heteroaryl compounds useful as inhibitors of sumo activating enzyme |
| CN106699785A (zh) * | 2015-07-13 | 2017-05-24 | 南开大学 | 作为CDK4/6抑制剂的2-(N-氧化吡啶-2基氨基)-吡啶并[2,3-d]嘧啶-7-酮类化合物 |
| US10336761B2 (en) * | 2015-07-23 | 2019-07-02 | Bristol-Myers Squibb Company | TGFβ receptor antagonist |
| KR102678021B1 (ko) | 2015-09-30 | 2024-06-26 | 버텍스 파마슈티칼스 인코포레이티드 | Dna 손상제와 병용되는, atr 저해제를 포함하는 암 치료용 약제학적 조성물 |
| JP6895963B2 (ja) | 2015-11-18 | 2021-06-30 | ジェンザイム・コーポレーション | 多発性嚢胞腎のバイオマーカーおよびその使用 |
| 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 |
| CA3059939A1 (en) | 2017-04-21 | 2018-10-25 | Kyn Therapeutics | Indole ahr inhibitors and uses thereof |
| AU2020394424A1 (en) | 2019-11-26 | 2022-06-16 | Ikena Oncology, Inc. | Polymorphic carbazole derivatives and uses thereof |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5688949A (en) * | 1991-04-22 | 1997-11-18 | Otsuka Pharmaceutical Factory, Inc. | Pyrazolo 1,5-A!pyrimidine derivatives and anti-inflammatory agent containing the same |
| US5571813A (en) * | 1993-06-10 | 1996-11-05 | Beiersdorf-Lilly Gmbh | Fused pyrimidine compounds and their use as pharmaceuticals |
| EP0628559B1 (en) | 1993-06-10 | 2002-04-03 | Beiersdorf-Lilly GmbH | Pyrimidine compounds and their use as pharmaceuticals |
| WO1995035298A1 (en) * | 1994-06-21 | 1995-12-28 | Otsuka Pharmaceutical Factory, Inc. | PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVE |
| US5919815A (en) * | 1996-05-22 | 1999-07-06 | Neuromedica, Inc. | Taxane compounds and compositions |
| US6191131B1 (en) * | 1997-07-23 | 2001-02-20 | Dupont Pharmaceuticals Company | Azolo triazines and pyrimidines |
| US6262096B1 (en) * | 1997-11-12 | 2001-07-17 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
| US6040321A (en) * | 1997-11-12 | 2000-03-21 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
| 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 |
| US6282096B1 (en) * | 2000-04-28 | 2001-08-28 | Siliconware Precision Industries Co., Ltd. | Integration of heat conducting apparatus and chip carrier in IC package |
| US7067520B2 (en) * | 2000-11-17 | 2006-06-27 | Ishihara Sangyo Kaisha, Ltd. | Preventive or therapeutic medicines for diabetes containing fused-heterocyclic compounds or their salts |
| FR2817469B1 (fr) | 2000-12-04 | 2003-04-18 | Oreal | Composition de coloration, procede d'obtention et utilisation pour la coloration de fibres keratiniques |
| CA2432417A1 (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) |
| JP4733794B2 (ja) * | 2000-12-26 | 2011-07-27 | 共栄電工株式会社 | 部材内面の表面処理方法および装置 |
| US6919815B2 (en) * | 2002-01-24 | 2005-07-19 | Emerson Electric Co. | Appliance control communication methods and apparatus |
| AU2003227437A1 (en) | 2002-04-23 | 2003-11-10 | Shionogi And Co., Ltd. | PYRAZOLO(1,5-a)PYRIMIDINE DERIVATIVE AND NAD(P)H OXIDASE INHIBITOR CONTAINING THE SAME |
| DE10223917A1 (de) | 2002-05-29 | 2003-12-11 | Bayer Cropscience Ag | Pyrazolopyrimidine |
| EP1537116B1 (en) * | 2002-09-04 | 2010-06-02 | Schering Corporation | Pyrazolopyrimidines suitable for the treatment of cancer diseases |
| NZ539162A (en) * | 2002-09-04 | 2006-07-28 | Schering Corp | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| EP1608652A1 (en) * | 2003-03-31 | 2005-12-28 | Vernalis (Cambridge) Limited | Pyrazolopyrimidine compounds and their use in medicine |
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2003
- 2003-09-03 NZ NZ539162A patent/NZ539162A/en not_active IP Right Cessation
- 2003-09-03 MX MXPA05002573A patent/MXPA05002573A/es active IP Right Grant
- 2003-09-03 ES ES03749317T patent/ES2285164T3/es not_active Expired - Lifetime
- 2003-09-03 US US10/654,157 patent/US7078525B2/en not_active Expired - Lifetime
- 2003-09-03 AT AT03749317T patent/ATE364608T1/de not_active IP Right Cessation
- 2003-09-03 JP JP2004534424A patent/JP2006501260A/ja not_active Withdrawn
- 2003-09-03 AR ARP030103189A patent/AR041134A1/es unknown
- 2003-09-03 KR KR1020057003150A patent/KR20050058507A/ko not_active Ceased
- 2003-09-03 CA CA2497444A patent/CA2497444C/en not_active Expired - Fee Related
- 2003-09-03 DE DE60314427T patent/DE60314427T2/de not_active Expired - Lifetime
- 2003-09-03 WO PCT/US2003/027405 patent/WO2004022559A1/en not_active Ceased
- 2003-09-03 CN CNB038244489A patent/CN1310918C/zh not_active Expired - Fee Related
- 2003-09-03 EP EP03749317A patent/EP1534709B1/en not_active Expired - Lifetime
- 2003-09-03 MY MYPI20033320A patent/MY139336A/en unknown
- 2003-09-03 TW TW092124349A patent/TW200413377A/zh unknown
- 2003-09-04 PE PE2003000901A patent/PE20041076A1/es not_active Application Discontinuation
-
2005
- 2005-03-03 ZA ZA200501851A patent/ZA200501851B/en unknown
-
2006
- 2006-03-31 US US11/395,974 patent/US7470695B2/en not_active Expired - Lifetime
-
2010
- 2010-03-02 JP JP2010045900A patent/JP2010132704A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004022559A1 (en) | 2004-03-18 |
| AR041134A1 (es) | 2005-05-04 |
| CA2497444C (en) | 2010-11-30 |
| US7078525B2 (en) | 2006-07-18 |
| ATE364608T1 (de) | 2007-07-15 |
| TW200413377A (en) | 2004-08-01 |
| JP2010132704A (ja) | 2010-06-17 |
| DE60314427T2 (de) | 2008-06-12 |
| CN1310918C (zh) | 2007-04-18 |
| EP1534709B1 (en) | 2007-06-13 |
| JP2006501260A (ja) | 2006-01-12 |
| NZ539162A (en) | 2006-07-28 |
| MY139336A (en) | 2009-09-30 |
| PE20041076A1 (es) | 2005-01-22 |
| DE60314427D1 (de) | 2007-07-26 |
| ES2285164T3 (es) | 2007-11-16 |
| MXPA05002573A (es) | 2005-09-08 |
| CN1738821A (zh) | 2006-02-22 |
| CA2497444A1 (en) | 2004-03-18 |
| US7470695B2 (en) | 2008-12-30 |
| HK1071570A1 (en) | 2005-07-22 |
| EP1534709A1 (en) | 2005-06-01 |
| US20040102451A1 (en) | 2004-05-27 |
| US20060235025A1 (en) | 2006-10-19 |
| KR20050058507A (ko) | 2005-06-16 |
| AU2003268357A1 (en) | 2004-03-29 |
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