CN103275019A - 4-[3-氯-4-取代苯胺基]-6-取代甲氧基甲酰氨基喹唑啉类化合物及制备和应用 - Google Patents
4-[3-氯-4-取代苯胺基]-6-取代甲氧基甲酰氨基喹唑啉类化合物及制备和应用 Download PDFInfo
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- CN103275019A CN103275019A CN2013101535466A CN201310153546A CN103275019A CN 103275019 A CN103275019 A CN 103275019A CN 2013101535466 A CN2013101535466 A CN 2013101535466A CN 201310153546 A CN201310153546 A CN 201310153546A CN 103275019 A CN103275019 A CN 103275019A
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- chloro
- quinazoline
- diethylin
- anilino
- kharophen
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- 238000002360 preparation method Methods 0.000 title claims abstract description 35
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical class [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 title abstract 2
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title abstract 2
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 12
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 12
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims abstract description 10
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- 230000002265 prevention Effects 0.000 claims abstract description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 5
- 201000005202 lung cancer Diseases 0.000 claims abstract description 5
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 3
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- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 claims description 66
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 66
- -1 formamido group quinazoline compounds Chemical class 0.000 claims description 44
- RPTKRGHYKSBDJL-UHFFFAOYSA-N 6-nitroquinazoline Chemical compound N1=CN=CC2=CC([N+](=O)[O-])=CC=C21 RPTKRGHYKSBDJL-UHFFFAOYSA-N 0.000 claims description 41
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 238000006073 displacement reaction Methods 0.000 claims description 22
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
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- LZOSFEDULGODDH-UHFFFAOYSA-N 4-chloro-6-nitroquinazoline Chemical compound N1=CN=C(Cl)C2=CC([N+](=O)[O-])=CC=C21 LZOSFEDULGODDH-UHFFFAOYSA-N 0.000 claims description 13
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 7
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 claims description 4
- 201000008275 breast carcinoma Diseases 0.000 claims description 4
- 235000017550 sodium carbonate Nutrition 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 230000000259 anti-tumor effect Effects 0.000 abstract description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
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- 150000003246 quinazolines Chemical class 0.000 description 5
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- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
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Claims (10)
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CN201310153546.6A CN103275019B (zh) | 2013-04-26 | 2013-04-26 | 4-[3-氯-4-取代苯胺基]-6-取代甲氧基甲酰氨基喹唑啉类化合物及制备和应用 |
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CN103275019A true CN103275019A (zh) | 2013-09-04 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104876882A (zh) * | 2015-05-13 | 2015-09-02 | 浙江工业大学 | 6-氨基喹唑啉类化合物及应用 |
CN104926737A (zh) * | 2015-05-13 | 2015-09-23 | 浙江工业大学 | 4-(3-取代苯胺基)-6-取代基喹唑啉类化合物及制备和应用 |
CN106432206A (zh) * | 2016-08-30 | 2017-02-22 | 成都美睿科生物科技有限公司 | 一种用于合成拉帕替尼或其中间体5‑(4‑羟基喹唑啉)‑呋喃‑2‑甲醛的方法 |
CN108276386A (zh) * | 2018-01-24 | 2018-07-13 | 浙江工业大学 | 环己基甲氧基甲酰氨基喹唑啉类化合物及制备和应用 |
CN108324718A (zh) * | 2018-01-24 | 2018-07-27 | 浙江工业大学 | 环己基甲氧基甲酰氨基氯代苯并氮杂*基喹唑啉类化合物在治疗白血病药物中的应用 |
Citations (6)
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EP0566226A1 (en) * | 1992-01-20 | 1993-10-20 | Zeneca Limited | Quinazoline derivatives |
US6015814A (en) * | 1995-04-27 | 2000-01-18 | Zeneca Limited | Quinazoline derivative |
CN101619043A (zh) * | 2008-06-30 | 2010-01-06 | 和记黄埔医药(上海)有限公司 | 喹唑啉衍生物及其医药用途 |
CN101665466A (zh) * | 2009-08-24 | 2010-03-10 | 江苏省原子医学研究所 | 一种喹唑啉二硫二氮衍生物的制备方法 |
WO2010076764A1 (en) * | 2008-12-29 | 2010-07-08 | Universita' Degli Studi Di Parma | Irreversible egfr inhibitor compounds with antiproliferative activity |
US20120283280A1 (en) * | 2011-04-18 | 2012-11-08 | Bertrand Jean-Claude | Imidazotetrazinone-based combi-molecules |
-
2013
- 2013-04-26 CN CN201310153546.6A patent/CN103275019B/zh not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0566226A1 (en) * | 1992-01-20 | 1993-10-20 | Zeneca Limited | Quinazoline derivatives |
US6015814A (en) * | 1995-04-27 | 2000-01-18 | Zeneca Limited | Quinazoline derivative |
CN101619043A (zh) * | 2008-06-30 | 2010-01-06 | 和记黄埔医药(上海)有限公司 | 喹唑啉衍生物及其医药用途 |
WO2010076764A1 (en) * | 2008-12-29 | 2010-07-08 | Universita' Degli Studi Di Parma | Irreversible egfr inhibitor compounds with antiproliferative activity |
CN101665466A (zh) * | 2009-08-24 | 2010-03-10 | 江苏省原子医学研究所 | 一种喹唑啉二硫二氮衍生物的制备方法 |
US20120283280A1 (en) * | 2011-04-18 | 2012-11-08 | Bertrand Jean-Claude | Imidazotetrazinone-based combi-molecules |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104876882A (zh) * | 2015-05-13 | 2015-09-02 | 浙江工业大学 | 6-氨基喹唑啉类化合物及应用 |
CN104926737A (zh) * | 2015-05-13 | 2015-09-23 | 浙江工业大学 | 4-(3-取代苯胺基)-6-取代基喹唑啉类化合物及制备和应用 |
CN104876882B (zh) * | 2015-05-13 | 2018-05-08 | 浙江工业大学 | 6-氨基喹唑啉类化合物及应用 |
CN106432206A (zh) * | 2016-08-30 | 2017-02-22 | 成都美睿科生物科技有限公司 | 一种用于合成拉帕替尼或其中间体5‑(4‑羟基喹唑啉)‑呋喃‑2‑甲醛的方法 |
CN108276386A (zh) * | 2018-01-24 | 2018-07-13 | 浙江工业大学 | 环己基甲氧基甲酰氨基喹唑啉类化合物及制备和应用 |
CN108324718A (zh) * | 2018-01-24 | 2018-07-27 | 浙江工业大学 | 环己基甲氧基甲酰氨基氯代苯并氮杂*基喹唑啉类化合物在治疗白血病药物中的应用 |
CN108276386B (zh) * | 2018-01-24 | 2020-10-09 | 浙江工业大学 | 环己基甲氧基甲酰氨基喹唑啉类化合物及制备和应用 |
CN108324718B (zh) * | 2018-01-24 | 2020-10-09 | 浙江工业大学 | 环己基甲氧基甲酰氨基氯代苯并氮杂*基喹唑啉类化合物在治疗白血病药物中的应用 |
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