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Optically pure quinazoline compounds

A compound and composition technology, applied in the field of optically pure quinazoline compounds, can solve problems such as the absence of optically pure isomers

Active Publication Date: 2015-07-01
JIANGSU HANSOH PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Chinese patent 99803887.3 publicly reported a series of compounds, which have protein tyrosine kinase inhibitory activity; Chinese patent 20081000815 also publicly reported a series of new quinazoline compounds, but they were all developed in the form of racemates, and did not its optically pure isomers

Method used

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  • Optically pure quinazoline compounds
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  • Optically pure quinazoline compounds

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0102] Preparation Example 1 Preparation of N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)-6-iodoquinazolin-4-amine

[0103] Add 6-iodo-3H-quinazolin-4-one (100g) in a 2000mL flask, dissolve in a mixed solvent of thionyl chloride (1000ml) and N,N-dimethylformamide (20ml), heat Reflux until the reaction solution is clear and transparent. Thionyl chloride was distilled off, dried twice with toluene, and set aside.

[0104] Dissolve the standby intermediate in isopropanol (2000ml), add 3-chloro-4-(3-fluoro-benzyloxy)-aniline hydrochloride (70g), add anhydrous K under mechanical stirring 2 CO 3 (150g), heated to reflux overnight. The next day, the reaction solution was cooled to room temperature, filtered under reduced pressure, and the filter cake was beaten with water to remove K 2 CO 3 To neutral, filter under reduced pressure, and dry in vacuo to obtain the title product: 95g, off-white solid.

[0105] m / z(M+1) + :506.

preparation example 2

[0106] Preparation Example 2 Preparation of N-(1-(3-fluorobenzyl)-1H-indazol-5-yl)-6-iodoquinazolin-4 amine

[0107] The method is the same as in Preparation Example 1, except that 3-chloro-4-(3-fluoro-benzyloxy)-aniline hydrochloride is changed to 1-(3-fluorobenzyl)-1H-indazole-5amine Hydrochloride.

[0108] m / z(M+1) + :496.

preparation example 3

[0109]Preparation Example 3 Preparation of 5-(4-(4-(3-fluorobenzyloxy)-3-chlorophenylamino)quinazolin-6-yl)furan-2-aldehyde

[0110] Preparation Example 1 compound (50g), 5-boronic acid-2-furfural (21g), Pd(PPh 3 ) 2 Cl 2 (6.2g), triethylamine (62ml), and methanol (1000ml) were put into the reaction flask, and refluxed for 2 hours. Cool to room temperature, filter, wash the filter cake with a small amount of methanol, and then dry at 50°C to obtain the title compound: 40g, a yellow solid.

[0111] m / z(M+1) + :473.

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PUM

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Abstract

The present invention relates to an optically pure quinazoline compound, especially the compound as represented by formula (I), and a pharmaceutical composition containing therapeutically effective amount of the compound. Also a use of the pharmaceutical composition for the preparation of a medicament for the treatment of diseases related to the modulation of c-erbB-2 and / or the activity of EGF-R protein tyrosine kinase.

Description

technical field [0001] The invention relates to an optically pure quinazoline compound, a pharmaceutical composition containing a therapeutically effective amount of the compound, and its preparation for treating diseases related to the regulation of c-erbB-2 and / or EGF-R protein tyrosine kinase activity use in medicines. Background technique [0002] Protein tyrosine kinases catalyze the phosphorylation of specific tyrosine residues in various proteins involved in the regulation of cell growth and differentiation. Protein tyrosine kinases can be broadly classified as receptor (eg EGFr, c-erbB-2, c-met, tie-2, PDGFr, FGFr) or non-receptor (eg c-src, lck, zap70) kinases. Inappropriate or uncontrolled activation of many of these kinases, ie aberrant protein tyrosine kinase activity, for example by overexpression or mutation, has been shown to lead to uncontrolled cellular production. [0003] Abnormal activities of protein tyrosine kinases, such as c-erbB-2, c-src, c-met, EG...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04C07D417/04C07D405/14C07C309/30C07C303/32A61K31/517A61P35/00A61P17/06
CPCA61K31/517A61P17/06A61P35/00
Inventor 岑均达唐家邓吴雪松
Owner JIANGSU HANSOH PHARMA CO LTD