New quinazoline hind derivative, medicinal composition containing same and their use

A technology of derivatives and mixtures, applied in the field of 4-substituted anilinoquinazoline derivatives, can solve the problems of blocking cell differentiation regulation function, inducing tumors and the like

Inactive Publication Date: 2006-01-25
SHENYANG J & HEALTH PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, pathological mechanisms such as gene mutation, gene fusion, autocrine and paracrine cycles will lead to the continuous activati

Method used

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  • New quinazoline hind derivative, medicinal composition containing same and their use
  • New quinazoline hind derivative, medicinal composition containing same and their use
  • New quinazoline hind derivative, medicinal composition containing same and their use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0155] Example 1: 4-(3-chloro-4-fluoroanilino)-6-methoxy-7-[[3-[(5-dimethylamino)methylfuran-2-]methylthio] Propoxy]quinazoline oxalate

[0156]Step A: Preparation of methyl 3-methoxy-4-(3-chloropropoxy)benzoate

[0157] In 150 mL of dimethylformamide (DMF), add 9.1 g (0.05 mol) of methyl 3-methoxy-4-hydroxybenzoate, 15.8 g (0.1 mol) of 1,3-bromochloropropane, anhydrous carbonic acid Potassium 10.4g (0.075mol), stirred at 70-80°C for 6h. After the reaction was completed, the reaction solution was poured into ice water, extracted with dichloromethane, the organic phases were combined, washed with water, dried over anhydrous magnesium sulfate, evaporated to remove the solvent, and dried to obtain 12.3 g of the product (yield: 95.3%).

[0158] Step B: Preparation of methyl 2-nitro-4-(3-chloropropoxy)-5-methoxybenzoate

[0159] 12.3 g (0.048 mol) of methyl 3-methoxy-4-(3-chloropropoxy)benzoate was added to 100 mL of chloroform, and stirred to dissolve. Cool to about 10°C, slow...

Embodiment 2-39

[0173] According to the method of Example 1, using methyl 3-methoxy-4-hydroxybenzoate and 1,3-bromochloropropane or 1,2-bromochloroethane as starting materials, first prepare 4-chloro- 6-methoxy-7-(3-chloroalkoxy) quinazoline, then with suitable amine substitution reaction, then with furanmethylthiol substitution reaction, and then carry out Mannich reaction with suitable aliphatic amine, respectively Compounds of Examples 2-39 were obtained:

Embodiment 2

[0174] Example 2: 4-(3-chloro-4-fluoroanilino)-6-methoxy-7-[[3-[5-(N-methylethylamino)methylfuran-2-]methanol Thio]propoxy]quinazoline oxalate

[0175] 1 H-NMR(DMSO): 1.20(t, 3H), 2.05(m, 2H), 2.62(s, 3H), 2.68(t, 2H), 2.99(q, 2H), 3.82(s, 2H), 3.96 (s, 3H), 4.19(t, 2H), 4.29(s, 2H), 6.39(d, 1H), 6.61(d, 1H), 7.20(s, 1H), 7.44(t, 1H), 7.81( m, 1H), 7.86(s, 1H), 8.13(dd, 1H), 8.51(s, 1H); MS: 545.2(M+H).

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Abstract

The invention relates to quinazoline derivatives having a general formula (I), and mixture of their optically active body or racemic body, and diastereoisomer, their pharmaceutically acceptable salts, hydrate or solvate, wherein R1, R2, A, X and Q1 are defined in the specification. The derivatives can be used for preparing protein tyrosine coyness inhibitor, and for preparing medicament for treating and/or preventing cancer and other hyperplasia diseases.

Description

technical field [0001] The present invention relates to 4-substituted anilinoquinazoline derivatives, pharmaceutical compositions containing the derivatives as active ingredients, and their use in the preparation of protein tyrosine kinase inhibitors and in the treatment and / or prevention of various Use in medicine for cancer and other proliferative diseases. Background technique [0002] Cancer, also known as malignant tumor, is a common disease that seriously threatens human health. At present, the mortality rate of cancer is still rising, and there is still a lack of effective drugs for common solid tumors. Most of the existing chemotherapy drugs kill cancer cells by interfering with certain links in the cell division process. There is no essential difference between cancer cells and normal cells. While killing cancer cells, they will also produce toxic side effects. [0003] Protein tyrosine kinase (protein tyrosine kinase) is an enzyme that can selectively phosphorylat...

Claims

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Application Information

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IPC IPC(8): C07D239/94C07D405/12A61K31/517A61K31/5355A61K31/496A61P35/00A61P9/10A61P17/06
Inventor 史秀兰
Owner SHENYANG J & HEALTH PHARMA
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