Tyrosine kinase inhibitor, preparation method and application thereof

A tyrosine kinase and inhibitor technology, applied in the field of medicinal chemistry, can solve problems such as poor tumor effect

Inactive Publication Date: 2016-06-15
SHANGHAI INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the above-mentioned technical problems in the prior art, the present invention provides a tyrosine kinase inhibitor and its preparation method and use. The tyrosine kinase inhibitor and its preparation method and use should solve the existing The technical problem of poor effect of drugs in the treatment of tumors

Method used

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  • Tyrosine kinase inhibitor, preparation method and application thereof
  • Tyrosine kinase inhibitor, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 13

[0040] The synthesis of embodiment 13-chloro-4-butoxyaniline

[0041] Phenol potassium salt (0.600g, 2.84mmol), bromo-n-butane (0.501g, 3.70mmol), potassium carbonate (1.96g, 14.2mmol), and 15ml of acetonitrile were added to a three-necked flask and heated to reflux. After the reaction was completed, after a series of The treatment gave 0.540 g of yellow 2-chloro-4-butoxynitrobenzene with a yield of 95.4%. The product obtained by the reaction (0.54, 2.36mmol), iron powder (1.32g, 23.6mmol), ammonium chloride solid (1.62g, 23.6mmol) was added into 15ml of water and methanol mixed solvent into a three-necked flask and heated to reflux. After the reaction was completed, After a series of post-treatments, 0.420 g of the gray product 3-chloro-4-butoxyaniline was obtained, with a yield of 93.0%.

Embodiment 28

[0042] Synthesis of Example 28-(4-amino-2-chlorophenoxy) octanoic acid ethyl ester

[0043]Phenol potassium salt (0.200g, 0.948mmol) and ethyl 8-bromooctanoate (0.308g, 1.23mmol), potassium carbonate (0.601g, 4.34mmol), and 10ml of acetonitrile were added to a three-necked flask and heated to reflux. After the reaction was completed, a series of After post-treatment, 0.28 g of yellow ethyl 8-(2-chloro-4-nitrophenylamino)octanoate was obtained, with a yield of 90.6%. The product (0.28g, 0.816mmol) obtained by the reaction, iron powder (0.457g, 8.16mmol), ammonium chloride solid (0.436g, 8.16mmol) was added into a three-necked flask and heated to reflux with 24ml of water and methanol mixed solvent, after the reaction was completed 0.260 g of the gray product ethyl 8-(4-amino-2-chlorophenoxy)octanoate was obtained through a series of post-treatments, with a yield of 93.5%.

Embodiment 3

[0044] Synthesis of Example 32-(4-amino-2-chlorophenoxy) ethyl acetate

[0045] Phenol potassium salt (0.400g, 1.90mmol), ethyl bromoacetate (0.566g, 2.46mmol), potassium carbonate (1.21g, 8.68mmol), and 15ml of acetonitrile were added into a three-necked flask and heated to reflux for reaction. After the reaction was completed, a series of After post-treatment, 0.46 g of yellow ethyl 2-(2-chloro-4-nitrophenoxy)acetate was obtained, with a yield of 93.9%. The product obtained by the reaction (0.46g, 1.78mmol) and iron powder (0.991g, 17.8mmol), ammonium chloride solid (0.952g, 17.8mmol), 27ml water and methanol mixed solvent were heated to reflux, after the reaction was completed, after After treatment, 0.400 g of ethyl 2-(4-amino-2-chlorophenoxy)acetate was obtained as a gray product, with a yield of 92.2%.

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Abstract

A kind of tyrosine kinase inhibitor of the present invention, structure is as follows: Among them, R 1 is a halogen substituent, R 2 C1-C6 alkoxy, C1-C10 carbonate substituent, C1-C6 imino substituent, or R3 is methyl, ethyl, or -(CH 2 ) 2 OCH 3 . These tyrosine kinase inhibitors were synthesized by two methods starting from 2-halo-4-nitrophenol or 2-halo-4-nitroaniline. The invention takes the receptor (ErbB-1) and ErbB-2 (HER-2) on the tyrosine kinase epidermal growth factor as targets, and inhibits the activity of the tyrosine kinase to inhibit the tumor.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a tyrosine kinase inhibitor, in particular to a tyrosine kinase inhibitor and its preparation method and application. Background technique [0002] Over the past 30 years of reform and opening up, the total incidence of cancer in our country has shown a rapid upward trend, mainly reflected in the increase in types of cancer, which are caused by people's unhealthy lifestyles, such as lung cancer caused by smoking, etc. Liver cancer caused by drinking, etc. The serious situation of cancer forces people to invest more manpower and material resources in tumor treatment. [0003] Studies have found that the occurrence and appearance of various diseases are related to protein tyrosine kinase, and the occurrence and development of tumors are closely related to this kinase, and scientists have found that kinase inhibitors are highly effective and low-toxic, so more and more researchers h...

Claims

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Application Information

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IPC IPC(8): C07D239/94A61K31/519A61P35/00
CPCC07D239/94A61K31/519
Inventor 姚志艺薛楠楠宗豪强王东升王庆宣
Owner SHANGHAI INSTITUTE OF TECHNOLOGY
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