JP2013542210A5 - - Google Patents
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- JP2013542210A5 JP2013542210A5 JP2013535272A JP2013535272A JP2013542210A5 JP 2013542210 A5 JP2013542210 A5 JP 2013542210A5 JP 2013535272 A JP2013535272 A JP 2013535272A JP 2013535272 A JP2013535272 A JP 2013535272A JP 2013542210 A5 JP2013542210 A5 JP 2013542210A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- represented
- general formula
- imino
- substituted
- 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.)
- Granted
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 51
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 35
- 125000004429 atom Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052707 ruthenium Inorganic materials 0.000 claims description 25
- 125000001302 tertiary amino group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 239000000376 reactant Substances 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 17
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 150000003246 quinazolines Chemical class 0.000 claims description 15
- 239000003909 protein kinase inhibitor Substances 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 229940043355 kinase inhibitor Drugs 0.000 claims description 13
- 229910000510 noble metal Inorganic materials 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims description 3
- 125000005277 alkyl imino group Chemical group 0.000 claims description 2
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 42
- 239000013067 intermediate product Substances 0.000 claims 39
- -1 alkoxyacyl halide Chemical class 0.000 claims 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 33
- 239000003960 organic solvent Substances 0.000 claims 30
- 239000003446 ligand Substances 0.000 claims 26
- 150000001412 amines Chemical class 0.000 claims 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 18
- 229910052783 alkali metal Inorganic materials 0.000 claims 16
- 238000006243 chemical reaction Methods 0.000 claims 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 9
- 239000011230 binding agent Substances 0.000 claims 9
- 239000007795 chemical reaction product Substances 0.000 claims 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 9
- 230000035484 reaction time Effects 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 239000000243 solution Substances 0.000 claims 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 7
- 238000010992 reflux Methods 0.000 claims 7
- 150000003304 ruthenium compounds Chemical class 0.000 claims 7
- 239000007859 condensation product Substances 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 6
- 125000001118 alkylidene group Chemical group 0.000 claims 5
- 229910021529 ammonia Inorganic materials 0.000 claims 5
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 5
- 150000002460 imidazoles Chemical class 0.000 claims 5
- 238000002360 preparation method Methods 0.000 claims 5
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 4
- 239000013522 chelant Substances 0.000 claims 4
- 150000002191 fatty alcohols Chemical class 0.000 claims 4
- 239000000706 filtrate Substances 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 238000002156 mixing Methods 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- 239000000539 dimer Substances 0.000 claims 3
- 238000005658 halogenation reaction Methods 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- 239000011574 phosphorus Substances 0.000 claims 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 3
- 239000012279 sodium borohydride Substances 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- 229910017744 AgPF6 Inorganic materials 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 2
- 238000006555 catalytic reaction Methods 0.000 claims 2
- 230000009920 chelation Effects 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- 238000006482 condensation reaction Methods 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical class CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 claims 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000005262 alkoxyamine group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 238000005915 ammonolysis reaction Methods 0.000 claims 1
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 235000015320 potassium carbonate Nutrition 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- QSUBCYLNKZGIEQ-UHFFFAOYSA-N CCCCCC(C)Oc1cc2c(Nc(cc3Cl)ccc3F)ncnc2cc1OC Chemical compound CCCCCC(C)Oc1cc2c(Nc(cc3Cl)ccc3F)ncnc2cc1OC QSUBCYLNKZGIEQ-UHFFFAOYSA-N 0.000 description 1
- CHFHEMXVBHXICF-UHFFFAOYSA-N CNOc1cc2c(Nc(cc3Cl)ccc3F)ncnc2cc1OC Chemical compound CNOc1cc2c(Nc(cc3Cl)ccc3F)ncnc2cc1OC CHFHEMXVBHXICF-UHFFFAOYSA-N 0.000 description 1
- 0 COc1cc2ncnc(Nc(cc3Cl)ccc3F)c2cc1O*1*C1 Chemical compound COc1cc2ncnc(Nc(cc3Cl)ccc3F)c2cc1O*1*C1 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010521382.4A CN102452988B (zh) | 2010-10-27 | 2010-10-27 | 一种喹唑啉衍生物及其制备方法 |
| CN201010521382.4 | 2010-10-27 | ||
| PCT/CN2011/081453 WO2012055369A1 (zh) | 2010-10-27 | 2011-10-27 | 一种抑制肿瘤细胞增殖的喹唑啉衍生物、喹唑啉配合物蛋白激酶抑制剂及它们的制备方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013542210A JP2013542210A (ja) | 2013-11-21 |
| JP2013542210A5 true JP2013542210A5 (https=) | 2015-10-08 |
| JP5837079B2 JP5837079B2 (ja) | 2015-12-24 |
Family
ID=45993179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013535272A Expired - Fee Related JP5837079B2 (ja) | 2010-10-27 | 2011-10-27 | キナゾリン錯体、ならびにキナゾリン錯体の調製方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9233995B2 (https=) |
| EP (1) | EP2634178B1 (https=) |
| JP (1) | JP5837079B2 (https=) |
| CN (1) | CN102452988B (https=) |
| WO (1) | WO2012055369A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI577671B (zh) | 2011-11-14 | 2017-04-11 | Sunshine Lake Pharma Co Ltd | Aminoquinazoline derivatives and salts thereof and methods of use thereof |
| JP2017512776A (ja) | 2014-03-15 | 2017-05-25 | ウェイク フォレスト ユニバーシティ | 貴金属求電子体で修飾された官能化チロシンキナーゼ阻害剤およびそれと関連した方法 |
| EP2924045A1 (en) * | 2014-03-25 | 2015-09-30 | Medizinische Universität Wien | New agents for the treatment of cancer |
| CN106188147B (zh) * | 2015-05-08 | 2021-08-20 | 中国科学院化学研究所 | 含喹唑啉类配体的Pt配合物及其制备方法和应用 |
| CN105153047A (zh) * | 2015-08-25 | 2015-12-16 | 佛山市赛维斯医药科技有限公司 | 含新型苯并喹唑啉和邻位氟结构的酪氨酸激酶抑制剂及用途 |
| CN105153046A (zh) * | 2015-08-25 | 2015-12-16 | 佛山市赛维斯医药科技有限公司 | 双卤素取代的乙氧基苯并喹唑啉类酪氨酸激酶抑制剂及用途 |
| CN114524853B (zh) * | 2022-02-28 | 2023-12-12 | 南京师范大学 | 一种全反式维甲酸-芳基金属配合物、制备方法及应用 |
| CN116217550B (zh) * | 2022-12-26 | 2024-12-27 | 上海前瞻创新研究院有限公司 | 一种咪唑三联吡啶钌配合物溶解氧检测探针及其制备方法与应用 |
| CN119569738A (zh) * | 2024-12-09 | 2025-03-07 | 太原学院 | 一种喹唑啉小分子化合物及其制备方法与应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1268484A1 (en) * | 2000-03-17 | 2003-01-02 | Novo Nordisk A/S | Condensed imidazoles as histamine h3 receptor ligands |
| CA2476008C (en) * | 2002-03-30 | 2011-12-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| ES2305844T3 (es) | 2003-09-16 | 2008-11-01 | Astrazeneca Ab | Derivados de quinazolina como inhibidores de tirosina cinasa. |
| GB0321620D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| WO2005097134A2 (en) * | 2004-03-31 | 2005-10-20 | The Scripps Research Institute | Quinazoline based protein kinase inhibitors |
| CN1313449C (zh) * | 2005-07-14 | 2007-05-02 | 沈阳中海生物技术开发有限公司 | 新的喹唑啉类衍生物、含有其的药物组合物以及它们的用途 |
| CA2619037A1 (en) * | 2005-08-22 | 2007-03-01 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles medicaments comprising said compounds use and method for production thereof |
| US7977346B2 (en) | 2006-01-17 | 2011-07-12 | Guoqing Paul Chen | Spiro compounds and methods of use |
| CN101535279B (zh) * | 2006-09-11 | 2015-05-20 | 柯瑞斯公司 | 含锌结合基的喹唑啉基egfr抑制剂 |
| EP2190287B1 (en) * | 2007-09-10 | 2014-10-29 | Curis, Inc. | Tartrate salts or complexes of quinazoline based egfr inhibitors containing a zinc binding moiety |
| US8119616B2 (en) * | 2007-09-10 | 2012-02-21 | Curis, Inc. | Formulation of quinazoline based EGFR inhibitors containing a zinc binding moiety |
| CN101367793B (zh) * | 2008-09-26 | 2013-09-11 | 中国科学院广州生物医药与健康研究院 | 一种具有抗肿瘤活性的氨基喹唑啉衍生物及其盐类 |
-
2010
- 2010-10-27 CN CN201010521382.4A patent/CN102452988B/zh not_active Expired - Fee Related
-
2011
- 2011-10-27 JP JP2013535272A patent/JP5837079B2/ja not_active Expired - Fee Related
- 2011-10-27 US US13/882,100 patent/US9233995B2/en not_active Expired - Fee Related
- 2011-10-27 WO PCT/CN2011/081453 patent/WO2012055369A1/zh not_active Ceased
- 2011-10-27 EP EP11835642.7A patent/EP2634178B1/en not_active Not-in-force
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