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6-substituted quinazoline derivative, preparation method and application thereof

A quinazoline and derivative technology, applied in the field of medicinal chemistry, can solve the problems of increasing the difficulty of curing and the probability of recurrence

Inactive Publication Date: 2011-06-01
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If the receptors of cancer cells are overexpressed or overactivated, the cancer cells will grow in large numbers, thus increasing the difficulty of curing and the probability of recurrence

Method used

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  • 6-substituted quinazoline derivative, preparation method and application thereof
  • 6-substituted quinazoline derivative, preparation method and application thereof
  • 6-substituted quinazoline derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 16-

[0024] The preparation of embodiment 16-iodoquinazolin-4-ketone III

[0025] 2-Amino-5-iodobenzoic acid (105.2g, 0.40mol) and methyl imidium acetate (83.2g, 0.80mol) were added to 1000mL of glycerol, heated to dissolve, and a large amount of white solids precipitated after half an hour. Cool and filter to obtain 93.5 g of white solid 6-iodoquinazolin-4-one III, yield 86.1%, m.p.135-136°C; 1 H NMR (400MHz, DMSO): δ7.43-8.37 (m, 4H, ArH), 12.36 (s, 1H, ArH). ESI-MS: m / z 273 [M+H] + .

Embodiment 24-

[0026] The preparation of embodiment 24-chloro-6-iodoquinazoline IV

[0027] Dissolve 6-iodoquinazolin-4-one (93.5g, 0.34mol) in DMF (300mL), add thionyl chloride dropwise, and heat to reflux for 3h. The solvent was evaporated, and ethyl acetate was recrystallized to obtain 4-chloro-6-iodoquinazoline IV (90.2 g, 90.5%) as a white solid, m.p.165-167°C; 1 H NMR (400MHz, DMSO): δ7.43-8.37 (m, 4H, ArH). ESI-MS: m / z 291 [M+H] + .

Embodiment 3

[0028] The preparation of embodiment 32-chloro-4-(6-iodoquinazoline-4-amino)phenol V

[0029] 4-Chloro-6-iodoquinazoline (90.2 g, 0.31 mol) and 4-amino-2-chlorophenol (44.5 g, 0.31 mol) were dissolved in isopropanol (500 mL), and heated to reflux for 2 h. After the solution was cooled, it was filtered, washed with isopropanol and ether, and dried to obtain 2-chloro-4-(6-iodoquinazoline-4-amino)phenol V (112.8g, 91.3%), m.p.143-144°C; 1 H NMR (400MHz, DMSO): δ4.03 (s, 1H, NH), 7.43-8.37 (m, 7H, ArH), 10.31 (s, 1H, OH). ESI-MS: m / z 398 [M+ H] + .

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Abstract

The invention belongs to the technical field of pharmaceutical chemistry and discloses quinazoline derivatives as shown in a general formula (I), wherein the R1 and R2 are defined by the specification. The invention also discloses a preparation method for the derivatives, physiologically acceptable salts formed by the derivatives and inorganic or organic acid or alkali as well as a pharmaceutical composition containing the derivatives and the physiologically acceptable salts. The compounds have the valuable pharmacological properties, especially the inhibitory effect on the signal transduction caused by tyrosine kinase. The invention also discloses a method for treating diseases, especially treating diseases which have the characteristic of abnormal erbB family protein tyrosine kinase (PTK) activity.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a class of novel quinazoline derivatives or pharmaceutically acceptable salts thereof, a method for preparing said quinazoline derivatives, and pharmaceutical compositions containing these compounds in the preparation of anti-inflammatory drugs. Use in tumor medicine. Background technique [0002] Tyrosine Kinase Inhibitor mainly acts on epidermal growth factor receptor (EGFR). EGFR has an important influence and control correlation on the growth of cancer cells. If the receptors of cancer cells are overexpressed or overactivated, the cancer cells will grow in large numbers, thereby increasing the difficulty of curing and the probability of recurrence. EGFR receptors can be divided into four types of human epidermal growth factor receptors (Human Epidermal Receptor). The first type is usually called EGFR, the second type is called HER2, and the other types are thi...

Claims

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Application Information

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IPC IPC(8): C07F9/6558A61K31/675A61P35/00A61P35/02
Inventor 李祎亮蔡志强石玉刘巍徐为人邹美香汤立达侯文彬刘冰妮刘金雷刘经国李洪明任铁顺
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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