EGFR (epidermal growth factor receptor) inhibitor for treating cancer and synthesis method of EGFR inhibitor

A technology of epidermal growth factor and receptor inhibitors, applied in the field of drug synthesis, can solve problems such as unclear roles, and achieve the effect of easy purchase of raw materials, simple operation, and cheap raw materials

Inactive Publication Date: 2018-10-02
杨文思
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Likewise, aberrant EGFR signaling is associated with psoriasis, eczema, and atherosclerosis, however, the role played is unclear

Method used

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  • EGFR (epidermal growth factor receptor) inhibitor for treating cancer and synthesis method of EGFR inhibitor
  • EGFR (epidermal growth factor receptor) inhibitor for treating cancer and synthesis method of EGFR inhibitor
  • EGFR (epidermal growth factor receptor) inhibitor for treating cancer and synthesis method of EGFR inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthetic conditions of 3-cyclopropylamino-6-methylthio-2-pyrazinecarboxylic acid ethyl ester 2 are:

[0041] Mix ethyl 3-chloro-6-methylthio-2-pyrazinecarboxylate 1 (35.8g), cyclopropylamine (13.18g), potassium carbonate (44.65g) and dimethylformamide (358mL) and heat to Stir at 60-100°C for 8-14 hours; cool down to 15-25°C, add ice water (700mL) to the system, stir for 2-5 hours, and filter to obtain 3-cyclopropylamino-6-methylthio - Ethyl 2-pyrazinecarboxylate 2 (34.9 g, 90%).

[0042] 1 H NMR (CDCl 3 ,400MHz): δ(ppm)=8.42(s,1H),7.56(brs,1H),4.23(q,2H),2.59(s,3H),2.29(m,1H),1.29(t,3H) ,0.85(m,2H),0.57(m,2H); m / z(MS-ESI):254.47[M+1] + .

[0043] The synthetic conditions of 2-hydroxymethyl-3-cyclopropylamino-6-methylthiopyrazine 3 are:

[0044] Mix ethyl 3-cyclopropylamino-6-methylthio-2-pyrazinecarboxylate 2 (31.5g), lithium aluminum hydride (14.2g) and tetrahydrofuran (150mL), cool to -60-0°C, stir 2-5 hours; warm up to room temperature, add saturated ammo...

Embodiment 2

[0062] Biological Activity of Compounds of the Invention

[0063] 1. Experimental materials

[0064] 1. Cell lines: human glioma cell U251, human brain astroglioblastoma cell U87, cervical cancer cell Hela, human colon cancer cell HCT-l16, human breast cancer cell line MCF-7, human umbilical cord Venous endothelial cell line HUVEC.

[0065] 2. Experimental reagents: MTT (3-(4,5-dimethylthiazole-2)-2,5-diphenyltetrazolium bromide), PBS buffer, DMEM medium: Gibco, fetal bovine serum: Sijiqing company, DMSO: Sigma, trypsin: Gibco.

[0066] 3. Experimental equipment: cell incubator: Japan Sanyo Electric Co., Ltd., microplate reader: MOLECULAR company, optical microscope: LEICA company, ultra-clean workbench: Beijing Weida Purification Technology Research Institute.

[0067] Second, the preparation of reagents:

[0068] (1) PBS solution: NaCl 8g, KCl 0.2g, NaCl 2 HPO 4 2H 2 O 3.62g, KH 2 PO 4

[0069] 0.24g, the above mixture was dissolved in 900ml of distilled water, the...

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Abstract

The invention discloses an EGFR (epidermal growth factor receptor) inhibitor N-(5-(1-cyclopropyl-6-((3-fluorobenzyl)amino)-2-oxo-1,4-dihydropteridin-3(2H)-yl)pyridin-3-yl)acrylamide for treating cancer and a synthesis process of the EGFR inhibitor. The synthesis condition and method are simple to operate, raw materials are cheap and easy to buy, the EGFR N-(5-(1-cyclopropyl-6-((3-fluorobenzyl)amino)-2-oxo-1,4-dihydropteridin-3(2H)-yl)pyridin-3-yl)acrylamide can be prepared on a large scale, and sufficient N-(5-(1-cyclopropyl-6-((3-fluorobenzyl)amino)-2-oxo-1,4-dihydropteridine-3(2H)-yl)pyridine-3-yl)acrylamide can be provided for the following pharmacological tests.

Description

technical field [0001] The field of the invention belongs to the field of drug synthesis, in particular to an epidermal growth factor receptor inhibitor N-(5-(1-cyclopropyl-6-((3-fluorobenzyl)amino)- 2-oxo-1,4-dihydropteridin-3(2H)-yl)pyridin-3-yl)acrylamide and its synthesis process. Background technique [0002] The epidermal growth factor receptor (EGFR; ErbB-1; HER1 in humans) is a transmembrane protein that is the receptor for members of the epidermal growth factor family (EGF family) of extracellular protein ligands. EGFR(ErbB-1), HER2 / neu(ErbB-2), Her3(ErbB-3) and Her2(ErbB-3) are all members of the ErbB receptor family, which are four closely related receptors Subfamily 4 (ErbB-4) of tyrosine kinases. In many cancer types, mutations that affect EGFR expression or activity can lead to cancer. [0003] Insufficient signaling of EGFR and other receptor tyrosine kinases in humans has been linked to diseases such as Alzheimer's disease, while overexpression of its sign...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D475/00A61P35/00
CPCC07D475/00A61P35/00
Inventor 杨文思
Owner 杨文思
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