TW200806670A - Inhibitors of checkpoint kinases - Google Patents
Inhibitors of checkpoint kinases Download PDFInfo
- Publication number
- TW200806670A TW200806670A TW096113500A TW96113500A TW200806670A TW 200806670 A TW200806670 A TW 200806670A TW 096113500 A TW096113500 A TW 096113500A TW 96113500 A TW96113500 A TW 96113500A TW 200806670 A TW200806670 A TW 200806670A
- Authority
- TW
- Taiwan
- Prior art keywords
- isoquinoline
- triazolium
- group
- alkyl
- ketone
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 67
- 108091000080 Phosphotransferase Proteins 0.000 title description 7
- 102000020233 phosphotransferase Human genes 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 239
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 58
- 201000011510 cancer Diseases 0.000 claims abstract description 45
- 238000011282 treatment Methods 0.000 claims abstract description 45
- 125000001425 triazolyl group Chemical group 0.000 claims description 268
- OUQVKRKGTAUJQA-UHFFFAOYSA-N n-[(1-chloro-4-hydroxyisoquinolin-3-yl)carbonyl]glycine Chemical compound C1=CC=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C21 OUQVKRKGTAUJQA-UHFFFAOYSA-N 0.000 claims description 238
- -1 Ci-C10 alkyl Chemical group 0.000 claims description 143
- 125000000217 alkyl group Chemical group 0.000 claims description 126
- 125000000623 heterocyclic group Chemical group 0.000 claims description 108
- 125000003118 aryl group Chemical group 0.000 claims description 106
- 125000001424 substituent group Chemical group 0.000 claims description 78
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 74
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 71
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 70
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 70
- 125000003342 alkenyl group Chemical group 0.000 claims description 56
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 54
- 150000002576 ketones Chemical class 0.000 claims description 44
- 125000000304 alkynyl group Chemical group 0.000 claims description 43
- 239000003814 drug Substances 0.000 claims description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- GYPOFOQUZZUVQL-UHFFFAOYSA-N 2h-isoquinolin-3-one Chemical compound C1=CC=C2C=NC(O)=CC2=C1 GYPOFOQUZZUVQL-UHFFFAOYSA-N 0.000 claims description 32
- 239000007789 gas Substances 0.000 claims description 32
- 125000002950 monocyclic group Chemical group 0.000 claims description 31
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 29
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 29
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 23
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
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- QGFYFOHMBDMGBZ-UHFFFAOYSA-N 5-[(7-chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)phenol Chemical compound C1=C(O)C(CN(CC)CC)=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 QGFYFOHMBDMGBZ-UHFFFAOYSA-N 0.000 claims description 11
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- XBZYWSMVVKYHQN-MYPRUECHSA-N (4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid Chemical compound C1C[C@H](O)[C@@](C)(COS(O)(=O)=O)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C XBZYWSMVVKYHQN-MYPRUECHSA-N 0.000 claims description 5
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- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229940023080 viracept Drugs 0.000 description 1
- 229960000237 vorinostat Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 229940053867 xeloda Drugs 0.000 description 1
- 239000002676 xenobiotic agent Substances 0.000 description 1
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- WRSWIWOVJBYZAW-UHFFFAOYSA-M zinc;methanidylbenzene;bromide Chemical compound Br[Zn+].[CH2-]C1=CC=CC=C1 WRSWIWOVJBYZAW-UHFFFAOYSA-M 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229940061261 zolinza Drugs 0.000 description 1
- 229960000641 zorubicin Drugs 0.000 description 1
- FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79469406P | 2006-04-25 | 2006-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200806670A true TW200806670A (en) | 2008-02-01 |
Family
ID=38441857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW096113500A TW200806670A (en) | 2006-04-25 | 2007-04-17 | Inhibitors of checkpoint kinases |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7501435B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2013212A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5229221B2 (cg-RX-API-DMAC7.html) |
| AR (1) | AR060619A1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2007243520B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2649811A1 (cg-RX-API-DMAC7.html) |
| DO (1) | DOP2007000082A (cg-RX-API-DMAC7.html) |
| TW (1) | TW200806670A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2007127138A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102017525A (zh) * | 2005-01-06 | 2011-04-13 | 默克公司 | 关卡激酶抑制剂 |
| CN102014902A (zh) * | 2005-01-06 | 2011-04-13 | 默克公司 | 检查点激酶抑制剂 |
| WO2007081572A2 (en) | 2006-01-04 | 2007-07-19 | Merck & Co., Inc. | Inhibitors of checkpoint kinases |
| US9000027B2 (en) * | 2008-02-04 | 2015-04-07 | Dana-Farber Cancer Institute, Inc. | Chk1 suppresses a caspase-2 apoptotic response to DNA damage that bypasses p53, bcl-2 and caspase-3 |
| AU2009215073A1 (en) * | 2008-02-14 | 2009-08-20 | Merck Sharp & Dohme Corp. | Inhibitors of checkpoint kinases |
| US8614221B2 (en) | 2009-03-11 | 2013-12-24 | Merck Sharp & Dohme Corp. | Inhibitors of Akt activity |
| WO2013103899A2 (en) * | 2012-01-06 | 2013-07-11 | H. Lee Moffitt Cancer Center And Research Institute | Phosphorylation of histones and uses thereof |
| CA2938626A1 (en) | 2013-07-26 | 2015-01-29 | John Rothman | Compositions to improve the therapeutic benefit of bisantrene |
| TW201702218A (zh) | 2014-12-12 | 2017-01-16 | 美國杰克森實驗室 | 關於治療癌症、自體免疫疾病及神經退化性疾病之組合物及方法 |
| EP3950064A4 (en) * | 2019-04-03 | 2023-01-04 | Tera Stone Co., Ltd | THYMINE NUCLEOBASE BASED TRIAZOLOPYRIMIDINES AND PROCESS FOR THEIR PRODUCTION |
| CN117486890A (zh) | 2019-06-06 | 2024-02-02 | 和记黄埔医药（上海）有限公司 | 三环类化合物及其用途 |
| CN115197225B (zh) * | 2021-09-03 | 2023-04-11 | 贵州大学 | 一种五元杂环并喹唑啉酮类化合物及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1244501A (en) * | 1968-03-09 | 1971-09-02 | Aspro Nicholas Ltd | Heterocyclic amines |
| RU2145606C1 (ru) * | 1994-05-24 | 2000-02-20 | Ф.Хоффманн-Ля Рош Аг | Трициклические дикарбонильные производные и лекарственный препарат на их основе |
| US5677309A (en) * | 1996-03-22 | 1997-10-14 | Neurogen Corporation | 1,2,4-triazolo 4,3-c! quinazolin-3-ones and 1,2,4-triazolo 4,3-c!quinazolin-3-thiones; a new class of GABA brain receptor ligands |
| US20070149560A1 (en) * | 2003-03-14 | 2007-06-28 | Astrazeneca Ab | Novel fused triazolones and the uses thereof |
| JP5055494B2 (ja) * | 2005-06-10 | 2012-10-24 | メルク・シャープ・エンド・ドーム・コーポレイション | Ａｋｔ活性阻害剤 |
| WO2007081572A2 (en) | 2006-01-04 | 2007-07-19 | Merck & Co., Inc. | Inhibitors of checkpoint kinases |
-
2007
- 2007-04-17 TW TW096113500A patent/TW200806670A/zh unknown
- 2007-04-20 CA CA002649811A patent/CA2649811A1/en not_active Abandoned
- 2007-04-20 JP JP2009507739A patent/JP5229221B2/ja not_active Expired - Fee Related
- 2007-04-20 AU AU2007243520A patent/AU2007243520B2/en not_active Ceased
- 2007-04-20 EP EP07755786A patent/EP2013212A1/en not_active Withdrawn
- 2007-04-20 WO PCT/US2007/009643 patent/WO2007127138A1/en not_active Ceased
- 2007-04-20 AR ARP070101718A patent/AR060619A1/es not_active Application Discontinuation
- 2007-04-24 US US11/789,288 patent/US7501435B2/en not_active Expired - Fee Related
- 2007-04-25 DO DO2007000082A patent/DOP2007000082A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007243520B2 (en) | 2012-07-19 |
| WO2007127138A1 (en) | 2007-11-08 |
| AU2007243520A1 (en) | 2007-11-08 |
| JP5229221B2 (ja) | 2013-07-03 |
| US20070254879A1 (en) | 2007-11-01 |
| CA2649811A1 (en) | 2007-11-08 |
| JP2009535334A (ja) | 2009-10-01 |
| AR060619A1 (es) | 2008-07-02 |
| EP2013212A1 (en) | 2009-01-14 |
| DOP2007000082A (es) | 2007-12-31 |
| US7501435B2 (en) | 2009-03-10 |
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