CN102452988B - 一种喹唑啉衍生物及其制备方法 - Google Patents
一种喹唑啉衍生物及其制备方法 Download PDFInfo
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- 238000011393 cytotoxic chemotherapy Methods 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000011242 molecular targeted therapy Methods 0.000 description 1
- TZNGZBTWAOBVGW-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-2-(3-oxo-2,4-dihydro-1h-quinoxalin-2-yl)acetamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(=O)CC1C(=O)NC2=CC=CC=C2N1 TZNGZBTWAOBVGW-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000027405 negative regulation of phosphorylation Effects 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical group C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000011555 saturated liquid Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 150000003668 tyrosines Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
-
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (5)
| 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 |
| US13/882,100 US9233995B2 (en) | 2010-10-27 | 2011-10-27 | Quinazoline derivatives and quinazoline complex protein kinase inhibitor for inhibiting multiplication of tumor cells and preparation method thereof |
| EP11835642.7A EP2634178B1 (en) | 2010-10-27 | 2011-10-27 | Quinazoline derivative and quinazoline complex protein kinase inhibitor for inhibiting multiplication of tumor cells and preparation method thereof |
| JP2013535272A 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 |
| 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 |
Applications Claiming Priority (1)
| 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 |
Publications (2)
| Publication Number | Publication Date |
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| CN102452988A CN102452988A (zh) | 2012-05-16 |
| CN102452988B true CN102452988B (zh) | 2016-01-27 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201010521382.4A Expired - Fee Related CN102452988B (zh) | 2010-10-27 | 2010-10-27 | 一种喹唑啉衍生物及其制备方法 |
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 |
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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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Also Published As
| Publication number | Publication date |
|---|---|
| EP2634178A1 (en) | 2013-09-04 |
| US9233995B2 (en) | 2016-01-12 |
| EP2634178A4 (en) | 2013-09-04 |
| JP2013542210A (ja) | 2013-11-21 |
| EP2634178B1 (en) | 2016-08-24 |
| US20130225811A1 (en) | 2013-08-29 |
| WO2012055369A1 (zh) | 2012-05-03 |
| JP5837079B2 (ja) | 2015-12-24 |
| CN102452988A (zh) | 2012-05-16 |
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