2-(4-carbamoyl)anilino-4-aminopyrimidine derivatives and their applications

A carbamoyl and aminopyrimidine technology, applied in the field of 2-anilino-4-aminopyrimidine derivatives and applications, can solve the problems of few reports in research, achieve good application prospects, high yield, and significant anti-tumor activity Effect

Active Publication Date: 2022-05-03
GUIZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many research reports on new FAK inhibitors, but there are few reports on other electron-withdrawing substituents on the pyrimidine ring in the middle of Defactinib

Method used

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  • 2-(4-carbamoyl)anilino-4-aminopyrimidine derivatives and their applications
  • 2-(4-carbamoyl)anilino-4-aminopyrimidine derivatives and their applications
  • 2-(4-carbamoyl)anilino-4-aminopyrimidine derivatives and their applications

Examples

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Embodiment 1

[0032] Synthesis of 2-(4-carbamoyl)anilino-4-aminopyrimidine derivatives

[0033] (1) Synthesis of intermediate 2 (N-methyl-4-nitrobenzamide):

[0034] synthetic route:

[0035]

[0036] Synthesis process: take 250mL dry reactor, add 4-nitrobenzoic acid (1g, 6mmol), then add 30mL oxalyl chloride to dissolve, stir reaction on an oil bath at 65-70°C (anhydrous operation), and wait for the solution When it became a light yellow transparent liquid, the solution was spin-dried under reduced pressure to obtain a yellow solid; the yellow solid was dissolved in dichloromethane, and triethylamine (1.8 g, 178 mmol) was slowly added in an ice bath, and then 40% methylamine aqueous solution ( 287mg, 5.2mmol), stirred at room temperature for about 30 minutes; after the reaction was complete, the solvent was spin-dried under reduced pressure, the spin-dried mixture was dissolved with ethyl acetate and an appropriate amount of water and the solution was extracted with ethyl acetate for 5...

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Abstract

The invention belongs to the technical field of chemistry and medicine, and in particular relates to 2-(4-carbamoyl)anilino-4-aminopyrimidine derivatives and their application. The present invention obtains a class of 2-(4-carbamoyl)anilino-4-aminopyrimidine by replacing the electron-withdrawing substituent - trifluoromethyl group on the pyrimidine ring in the middle of Defactinib by using nitro, carboxyl, cyano, etc. derivative. 2-(4-carbamoyl)anilino-4-aminopyrimidine derivatives are a novel FAK inhibitor with very significant antitumor activity, and the in vitro activity of some derivatives is significantly higher than that of Defactinib; in the preparation of therapeutic It has a very good application prospect in anticancer drugs such as lung cancer, pancreatic cancer and liver cancer.

Description

technical field [0001] The invention belongs to the technical field of chemistry and medicine, and in particular relates to 2-(4-carbamoyl)anilino-4-aminopyrimidine derivatives and their application. Background technique [0002] Focal adhesion kinase (FAK) is a highly conserved protein tyrosine kinase that localizes sites of cell contact and cell adhesion; it was discovered in 1990 in the cell membrane and acts like a nucleus in other cellular compartments, as a viral One of the important substrates of the oncogene v-Src, and the first tyrosine protein kinase whose phosphorylation is dependent on integrin-mediated cell adhesion to the cell wall. [0003] FAK plays an important role in cell signal transduction. It is a key enzyme in the process of adhesion molecule superfamily integrin-mediated signal transmission. The center conducts multiple signal pathways. Studies have found that FAK is highly expressed in ovarian cancer, breast cancer, colon cancer, gastric cancer, me...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/42C07D239/48C07D405/12C07D401/12A61P35/00A61K31/505A61K31/506
CPCC07D239/42C07D239/48C07D405/12C07D401/12A61P35/00
Inventor 周孟张荣红王珊廖尚高何迅徐国波董永喜关焕玉李勇军
Owner GUIZHOU MEDICAL UNIV
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