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2, 6-disubstituted purine compound as well as preparation method and application thereof

A technology of compounds and purines, applied in the field of anti-tumor pharmacy, can solve problems such as difficulty in exerting ideal anti-tumor effects

Active Publication Date: 2022-07-29
ZIGONG NO 4 PEOPLES HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The existing EGFR tyrosine kinase inhibitors have been developed to the third-generation inhibitors that have the advantages of combining EGFR sensitive mutations and T790M mutation sites, but the emergence of drug resistance makes it difficult for them to exert ideal anti-tumor effects

Method used

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  • 2, 6-disubstituted purine compound as well as preparation method and application thereof
  • 2, 6-disubstituted purine compound as well as preparation method and application thereof
  • 2, 6-disubstituted purine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] A 2,6-disubstituted purine compound provides the following general structural formula of the compound or a pharmaceutically acceptable salt thereof:

[0034]

Embodiment 2

[0036] A kind of 2,6-disubstituted purine compounds, adopt following reaction formula to synthesize:

[0037] The compound was synthesized using the following reaction formula:

[0038]

[0039] Conditions used therein: (i) TEA, THF; (ii) DIPEA, i-PrOH, 75-85°C; (iii) TFA, 2-butanol, 75-85°C; (iv) Ranny-Ni, Hydrazine hydrate, MeOH , 0-25°C; (v) TEA, THF, 0-25°C. The detailed steps are as follows:

[0040] (1) Synthesis of Intermediate 1:

[0041] Dissolve 2,6-dichloro-9H-purine in tetrahydrofuran, add 1-fluoro-4-(2-bromoethyl)benzene, add triethylamine dropwise, react at room temperature for 1 hour, and concentrate under reduced pressure. After separation by column chromatography, intermediate 1 was obtained; wherein 2,6-dichloro-9H-purine: tetrahydrofuran: 1-fluoro-4-(2-bromoethyl)benzene: dropwise addition of triethylamine=9:14: 8:22;

[0042] (2) Synthesis of Intermediate 2:

[0043] The intermediate 1 was dissolved in isopropanol and stirred at room temperature, a...

Embodiment 3

[0053] (1) Synthesis of Intermediate 1:

[0054] Dissolve 2,6-dichloro-9H-purine in tetrahydrofuran, add 1-fluoro-4-(2-bromoethyl)benzene, add triethylamine dropwise, react at room temperature for 3 hours, and concentrate under reduced pressure. After separation by column chromatography, intermediate 1 was obtained; wherein 2,6-dichloro-9H-purine: tetrahydrofuran: 1-fluoro-4-(2-bromoethyl)benzene: dropwise addition of triethylamine=11:16: 9:24;

[0055] (2) Synthesis of Intermediate 2:

[0056] The intermediate 1 was dissolved in isopropanol and stirred at room temperature, and 4-(4-methylpiperazine)aniline and DIPEA were sequentially added. Then the reaction solution was heated to 85°C and reacted for 3 hours, and the yellow solid was obtained by suction filtration under reduced pressure. The crude product was separated by column chromatography to obtain Intermediate 2; wherein, Intermediate 1: isopropanol: 4-(4-methyl) Piperazine) aniline: DIPEA=12.5:32:6:3;

[0057] (3)...

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Abstract

The invention belongs to the technical field of anti-tumor pharmacy, and particularly relates to a 2, 6-disubstituted purine compound and application thereof, and the compound or pharmaceutically acceptable salt thereof, which can be used as an inhibitor of targeted EGFR L858R / T790M, has anti-tumor activity, can effectively inhibit the growth of cancer cells, and is simple in production method and low in cost.

Description

technical field [0001] The invention belongs to the technical field of antitumor pharmacy, and in particular relates to a 2,6-disubstituted purine compound, a preparation method and an application. Background technique [0002] Epidermal growth factor receptor (EGFR) is a member of the HER family. EGFR is the expression product of the proto-oncogene c-erbB-1 and is a transmembrane tyrosine kinase receptor. EGFR plays an important role in physiological processes such as cell growth, proliferation and differentiation by affecting downstream signaling pathways such as PI3K / AKT. The loss of function or abnormal activity of EGFR can cause tumor, diabetes, immune deficiency and cardiovascular disease. In particular, EGFR has also been identified as a key target in non-small cell lung cancer. [0003] Existing EGFR tyrosine kinase inhibitors have been developed into third-generation inhibitors that have the advantage of combining EGFR sensitive mutations and T790M mutation sites...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61P35/00A61K31/52
CPCC07D487/04A61P35/00
Inventor 罗昌彬车仕箭江从兵徐平王贯裴俊平
Owner ZIGONG NO 4 PEOPLES HOSPITAL
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