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Quinazoline-based carboxylate compound and use thereof

An ester compound, quinazoline-based technology, applied in the field of carboxylate compounds

Inactive Publication Date: 2020-04-03
贾玉庆
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, vandetanib is not yet on the market in my country (Wang Wei et al., Modern Oncology Medicine 2016, 24(23), 3703-3705)

Method used

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  • Quinazoline-based carboxylate compound and use thereof
  • Quinazoline-based carboxylate compound and use thereof
  • Quinazoline-based carboxylate compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl-(2-acetoxy)benzoate (formula I A Shown compound, abbreviated as "compound I A ", hereinafter the same) synthesis:

[0028]

[0029] Take 1.125g (0.00625mol) of 2-(acetoxy)benzoic acid and 30ml CH 2 Cl 2 Add to a 100ml round bottom flask to make solution I. Take 2ml (0.0026mol) SOCl 2 Dissolve in 10ml CH 2 Cl 2 , to prepare solution II. Under the ice-water bath, the solution I was cooled, and the solution II was added dropwise into the solution I under stirring, and after the solution II was added dropwise, the solution was refluxed for 30-60 minutes. The temperature was raised naturally, then gradually heated to 60°C, and refluxed for 5 hours. The solvent and other residues were removed under reduced pressure to obtain a yellow viscous liquid (compound II A ).

[0030] Compound (0.0025mol) shown in 0.800g formula III and 30mlCH 2 Cl 2 Add to a 50ml round bottom flask to make solution IV. Compoun...

Embodiment 2

[0035] 4-((3-Chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl-[2-amino-3-(4-tert-butoxy)phenyl) ] Propionate ("Compound I B ")Synthesis:

[0036]

[0037] Get 0.480g amino-protected 2-amino-3-(4-tert-butoxyphenyl) propionic acid (0.00105mol, compound a) (compound a was purchased from Chengdu Taihe Weiye Biotechnology Co., Ltd.) and 30mlCH 2 Cl 2 Add to a 100ml round bottom flask to make solution I. Take 0.6ml (0.0078mol) SOCl 2 Dissolve in 10ml CH 2 Cl 2 , to prepare solution II. Cool solution I in an ice-water bath, add solution II dropwise under stirring conditions, and reflux for 30 to 60 minutes, then raise the temperature of the reaction system to 60° C., and continue to reflux for 4 to 5 hours. The solvent was removed under reduced pressure to obtain a brown-yellow viscous liquid (compound II Ba ).

[0038] The above-mentioned brownish-yellow viscous liquid (compound II Ba ) dissolved in 20ml CH 2 Cl 2 , to make reaction solution III. Compound (0.001...

Embodiment 3

[0043] 6-(((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)-oxygen)carbonyl)picolinic acid ("Compound I C ")Synthesis:

[0044]

[0045] Take pyridine-2,6-dicarboxylic acid 1.25g (0.0075mol) and 30ml CH 2 Cl 2 Add to a 100ml round bottom flask to make solution I. Take 0.6ml (0.0078mol) SOCl 2 Dissolve in 10ml CH 2 Cl 2 , to prepare solution II. Under the ice-water bath, the solution I was cooled, and the solution II was added dropwise into the solution I under stirring, and after the solution II was added dropwise, the solution was refluxed for 30-60 minutes. Gradually heat to 60°C and reflux for 3 to 5 hours. After removing the solvent under reduced pressure, a light yellow viscous liquid (compound II C ).

[0046] The above light yellow viscous liquid (compound II C ) dissolved in 20ml CH 2 Cl 2 , to make reaction solution III. Compound shown in 2.400g formula III (0.0075mol) and 30mlCH 2 Cl 2 Add to a 50ml round bottom flask to make solution I...

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Abstract

The invention relates to a quinazolinyl group-containing carboxylate compound and a use thereof. The carboxylate compound is a compound represented by formula I, or a pharmaceutically acceptable salt thereof. The carboxylate compound can be used for preparing broad-spectrum anticancer drugs. In the formula I, R is an ethyl group substituted with a substituted phenyl group or / and an amino group, a substituted phenyl group, or a substituted pyridinyl group; and the substituent group of the substituted phenyl group is one of groups shown in the description, and the substituent group of the pyridinyl group is also shown in the description.

Description

technical field [0001] The invention relates to a quinazoline group-containing carboxylate compound and its application. Background technique [0002] Tumor is a multiple major disease, and the death rate of cancer patients in the world exceeds 6.9 million every year, and the incidence and mortality of tumors are on the rise rapidly. Although the causes of tumors are related to unfavorable living environment, living habits, and unknown unfavorable factors, the abnormal expression of oncogenes in the human body and the variation of signal transduction pathways lead to unlimited proliferation of cells, which is the driving force for tumor development, differentiation, and migration. important reason. In most human tumors, the mutation or overexpression of tyrosine kinases (Protein tyrosinekinases) causes intracellular downstream signaling pathways such as: MAP kinase (microtubule-associated protein kinase), PI3 kinase (3-phosphatidylinositol kinase), etc. Activated to inhibi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/94C07D401/12A61K31/517A61P35/00
CPCC07D239/94C07D401/12
Inventor 贾玉庆黄青春邱伟钟国清贾青张成业周玉胜饶文兵栾绍嵘
Owner 贾玉庆
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