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2,4,6-Tri-substituted pyrido[3,4-d]pyrimidines and their salts and applications

A compound, 4-d technology, applied in the field of anti-cancer drugs, can solve the problems of low efficiency and drug resistance, and achieve the effects of easy synthesis, novel structure, and significant anti-tumor activity in vivo

Active Publication Date: 2020-03-17
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, after clinical application of drugs such as gefitinib, it is found that their effectiveness is not high, and some patients develop acquired drug resistance after use

Method used

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  • 2,4,6-Tri-substituted pyrido[3,4-d]pyrimidines and their salts and applications
  • 2,4,6-Tri-substituted pyrido[3,4-d]pyrimidines and their salts and applications
  • 2,4,6-Tri-substituted pyrido[3,4-d]pyrimidines and their salts and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: 2-anilino-4-pyrrolidinyl-6-(5-(4-methyl-1-piperazinyl)-2-pyridyl)aminopyrido[3,4-d]pyrimidine ( Compound 1)

[0050] Step 1: Synthesis of 2,6-dichloro-4-pyrrolidinopyrido[3,4-d]pyrimidine (intermediate a1)

[0051]

[0052] Add 2,4,6-trichloropyrido[3,4-d]pyrimidine (2.50g, 10.66mmol) into a 250mL eggplant-shaped bottle, dissolve it in tetrahydrofuran, add DIPEA (2.8mL, 15.99mmol), Tetrahydropyrrole (1.0mL, 11.73mmol) was added dropwise under magnetic stirring. During the dropwise addition, yellow solids were continuously precipitated. After the drop was completed, the mixture was stirred at room temperature for 4 hours, and the solvent was removed by rotary evaporation. The residue was suspended in water, and a large amount of yellow solids precipitated. Suction filtration, washing the filter cake with water, and drying to obtain intermediate a1, light yellow solid powder, 2.61 g, yield 91.0%. 1 H NMR (400Mz, CDCl 3 )δ8.98(s,1H,Ar-H),7.94(s,1H,Ar-H),3....

Embodiment 2

[0059] Example 2: 2-(3-fluoroanilino)-4-pyrrolidinyl-6-(5-(4-methyl-1-piperazinyl)-2-pyridyl)aminopyrido[3,4 -d] pyrimidine (compound 2)

[0060] The method is the same as the preparation of compound 1, yellow solid powder.

Embodiment 3

[0061] Example 3: 2-(3-chloro-4-fluoroanilino)-4-pyrrolidinyl-6-(5-(4-methyl-1-piperazinyl)-2-pyridyl)aminopyrido [3,4-d]pyrimidine (compound 3)

[0062] The method is the same as the preparation of compound 1, yellow solid powder.

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PUM

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Abstract

The invention provides 2,4,6-trisubstituted pyridino[3, 4-d]pyrimidine compounds, salts thereof and application and belongs to the technical field of anti-cancer drugs. The compounds are novel in structure and easy in synthesis, have inhibiting activity to epidermal growth factor receptor (EGFR) tyrosine kinase, have obvious inhibiting activity to EGFR of a single mutant (L858R) and double mutants (L858R / T790M), have obvious in-vivo and in-vitro anti-tumor activity and can be applied to the treatment of EGFR mutation related cancers, the synthesis raw materials are readily available, and the synthesis method is easy to achieve.

Description

technical field [0001] The invention belongs to the technical field of anticancer drugs, and specifically relates to 2,4,6-trisubstituted pyrido[3,4-d]pyrimidine compounds and their salt compounds, preparation methods and applications. Background technique [0002] Cancer is one of the malignant diseases that seriously threaten human health. In the past 30 years, the incidence of cancer in my country has been in a period of rapid rise. The incidence of cancer is about 2 million per 100,000 people. Every year, there are more than 3.2 million new cases, about 2.7 million deaths, and more than 7 million patients under treatment. [0003] At present, the main treatment methods for cancer are still surgical treatment, radiotherapy and drug treatment, but to a large extent, drug treatment is still the main treatment. Therefore, it is of great significance to research and develop new anticancer drugs. [0004] Traditional antitumor drugs have strong activity, but lack of selectiv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61K31/519A61K31/5377A61P35/00
CPCC07D471/04
Inventor 张三奇张浩曹永孝赵宏义段伟民吕社民
Owner XI AN JIAOTONG UNIV
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