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Quinazoline derivatives for inhibiting cancer cell growth and method for the preparation thereof

A kind of technology of quinazoline and derivatives, applied in the field of quinazoline derivatives and medicinal salts thereof

Inactive Publication Date: 2007-12-26
HANMI SCI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] However, for treatment, it is necessary to administer the above-mentioned conventional quinazoline derivatives in large doses, which causes such side effects as diarrhea and rash

Method used

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  • Quinazoline derivatives for inhibiting cancer cell growth and method for the preparation thereof
  • Quinazoline derivatives for inhibiting cancer cell growth and method for the preparation thereof
  • Quinazoline derivatives for inhibiting cancer cell growth and method for the preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0339] Example 1 : Preparation of ({4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-ylcarbamoyl}-methyl)-carbamic acid t-butyl ester

[0340] (1-1) Preparation of 6-nitro-3H-quinazolin-4-one

[0341] 150 g of 2-amino-5-nitro-benzoylic acid was added to 200 ml of formamide, and the resulting solution was heated to 170°C for 4 hours, and cooled to 100°C. 500 ml of ice water was added thereto, stirred for 1 hour, and the resulting mixture was filtered under reduced pressure. The obtained residue was washed with water to obtain a solid, which was dried at 40°C for 15 hours to obtain the title compound of the above formula (140 g, 90%).

[0342] 1 H-NMR(DMSO-d 6 , 300MHz): δ8.77 (d, J = 2.7 Hz, 1H), 8.55 (dd, J = 6.9 Hz, 1H), 8.36 (s, 1H), 7.84 (d, J = 9 Hz, 1H).

[0343] (1-2) Preparation of 4-chloro-6-nitro-quinazoline hydrochloride

[0344] Add 415ml of thionyl(di)chloride and 123ml of phosphorousoxy chloride to 80g of the compound obtained in (1-1), add 3ml of N,N-dim...

Embodiment 2

[0355] Example 2 : Preparation of N-({4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-ylcarbamoyl}-methyl)-2-methoxy Base-acetamide

[0356] (2-1) Preparation of (2-Methoxy-Acetylamino)-Ethyl Acetate

[0357] 1.5 ml of triethylamine was added to 500 mg of amino-ethyl acetate hydrochloride dissolved in 5 ml of chloroform, and the solution was cooled to -78°C. 0.34 ml of methoxyacetyl chloride diluted with 3 ml of chloroform was slowly added thereto, and the resulting solution was slowly heated to room temperature and reacted for 6 hours. The reacted solution was washed with distilled water, adjusted to pH 8-9 by adding saturated sodium bicarbonate solution, extracted with an organic solvent, dried over magnesium sulfate, filtered and distilled under reduced pressure to obtain the title compound (595 mg, 75% ).

[0358] 1 H-NMR(CDCl 3 , 300MHz): δ7.15 (br s, 1H), 4.26 (q, 2H), 4.11 (d, 2H), 3.98 (s, 2H), 3.48 (s, 3H), 1.33 (t, 3H).

[0359] (2-2) Preparation of (2-methox...

Embodiment 3

[0368] Example 3 : Preparation of N-({4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-ylcarbamoyl}-methyl)-2-methanesulfon Acyl-acetamide

[0369] Add 16 mg of 1-hydroxybenzotriazole and 53 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride to 18 mg of methanesulfonyl acetic acid dissolved in 3 ml of THF. After 50 mg of the compound obtained in Example 2 (2-1), the solution was reacted for 2 hours. The reaction solution was extracted with distilled water, and the obtained residue was filtered under reduced pressure to obtain the title compound (44 mg, 70%).

[0370] 1 H-NMR(CDCl 3 , 300MHz): δ 8.60 (s, 1H), 8.52 (s, 1H), 7.82 (d, 1H), 7.69 (m, 2H), 7.54 (dd, 1H), 7.31 (m, 2H), 7.21 (t , 2H), 6.97(m, 2H), 5.12(s, 2H), 4.12(s, 2H), 4.03(s, 2H), 3.14(s, 3H).

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PUM

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Abstract

The present invention relates to a novel quinazoline derivative and a pharmaceutically acceptable salt thereof for inhibiting the growth of cancer cells and a pharmaceutical composition comprising same as an active ingredient.

Description

Invention field [0001] The present invention relates to a novel quinazoline derivative and a pharmaceutical salt thereof for inhibiting the growth of cancer cells, a method for preparing the same, and a pharmaceutical composition containing it as an active ingredient. Background of the invention [0002] Most of the traditional drugs used to treat cancer such as taxanes such as paclitaxel and doxetaxel; vinca alkaloids such as vincristine, vinblastine and vinorelbine; anthracyclines such as daunorubicin and doxetaxel ; Camptothecins such as topotecan, irinotecan; actinomycin; and etopocid are based on selective cytotoxicity, but this selectivity for cancer cells has produced many unsatisfactory side effects. [0003] In order to overcome this problem, recent research has focused on targets at a specific molecular level in cells to maximize the therapeutic effect of anticancer agents without causing adverse side effects. [0004] In cells, there are many signal transduction system...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/94
CPCC07D401/12C07D239/94C07D409/12C07D405/12C07D413/12C07D403/12A61P35/00A61P43/00A61K31/517
Inventor 咸泳孔智贤车美英金锺佑金孟燮金银英宋芝连金昌仁金世永李宽淳
Owner HANMI SCI CO LTD
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