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Anti-tumor compound and application thereof

A compound, phenyl technology, applied in the field of small molecule compounds, can solve the problem of persistent drug resistance, and achieve the effects of good anti-tumor activity, inhibition of proliferation, and good inhibition rate

Active Publication Date: 2020-09-25
SICHUAN PROVINCIAL PEOPLES HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a brand-new small molecule compound for the problem that the mutation of several existing ALK small molecule inhibitor drug resistance genes causes drug resistance to persist

Method used

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  • Anti-tumor compound and application thereof
  • Anti-tumor compound and application thereof
  • Anti-tumor compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Synthesis of tert-butyl 4-(4-amino-5-isopropoxy-2-methyl-phenyl)piperidine-1-carboxylate (compound a)

[0070] Weigh 1mmol (284.20mg) of 2-isopropoxy-5-methyl-4-(4-piperidine)aniline hydrochloride into a 25ml round bottom reaction bottle, add an appropriate amount of dichloromethane as a solvent, and shake to dissolve Add 3 mmol (383.54 μl) triethylamine, and finally add 4 equivalents of BOC anhydride to completely dissolve into a colorless liquid, stir at room temperature for 4 h, and monitor the reaction progress by thin layer chromatography (TLC). After the reaction is complete, spin the reaction solution directly to obtain a yellow oil, fill a silica gel column with 200-300 mesh silica gel powder, separate through the column with dichloromethane:methanol=2:1, detect the product by TLC, and spin dry to obtain a colorless oil Intermediate a. The yield was 95.7%.

Embodiment 2

[0072] Synthesis of tert-butyl 4-(4-(2,5-dichloro-4-pyrimidine)amino-5-isopropoxy-2-methylphenyl)piperidine-1-carboxylate (compound b)

[0073] Weigh 1mmol (350.20mg) of compound a into a 25ml round-bottomed reaction flask, add an appropriate amount of isopropanol as a solvent, then add 3mmol (523.98μl) N,N-diisopropylethylamine; weigh 1.5mmol (275.88mg ) 2,4,5-trichloropyrimidine was dissolved in 1ml of isopropanol, and added dropwise to the reaction system, and reacted for about 5 hours, and the reaction progress was monitored by TLC. After the reaction is complete, add about 15ml of water to disperse and extract with dichloromethane, a small amount for several times. After the extraction is complete, combine all the organic layers of dichloromethane, then add an appropriate amount of saturated sodium chloride solution to wash for 2-3 times, and then add anhydrous magnesium sulfate After drying for about 30 minutes, it was concentrated and dried under reduced pressure to obt...

Embodiment 3

[0075] (1) 5-chloro-N2-(4-fluorophenyl)-N4-(2-isopropoxy-5-methyl-4-piperidine-phenyl)pyrimidine-2,4-diamine (CR -B1) synthetic method:

[0076] Weigh 1mmol (495.20mg) of intermediate b and 1.5mmol (166.68mg) of p-fluoroaniline into a 25ml round bottom flask, add an appropriate amount of isopropanol as a solvent, and then add a catalytic amount (about 1%) of concentrated hydrochloric acid, The reaction was continued overnight at 80°C. The progress of the reaction was monitored by TLC. After the reaction is complete, cool the reaction solution to room temperature, add a small amount (about 5 drops) of trifluoroacetic acid, and stir at room temperature for 1 hour. The corresponding solid precipitates out. The solid is collected by filtration to remove the solvent, washed with water several times, and dried in vacuum to obtain the target product CR-B1. Yield 71.3%.

[0077] 1H NMR (400MHz, DMSO) δ10.18(s,1H),9.10(s,2H),8.30(s,1H),7.64(s,1H),7.51(s,2H),7.05(t,J= 8.8Hz, 2H), 6...

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Abstract

The present invention relates to a compound having a structure of formula I, in which the substituent R is C6-C8 cycloalkyl, aryl, n R1 substituted aryl, or n R1 substituted C6-C8 cycloalkyl, n being1-4; wherein the R1 is independently selected from a halogen atom, a C1-C6 alkyl group, a C2-C4 alkenyl group, a C2-C3 alkynyl group, a fluorine-substituted C1-C4 alkyl group, a phenyl group, a substituted phenyl group, a nitro group, a pyridyl group, a pyrrolyl group, a pyrazinyl group, a piperazinyl group and a furyl group; the R2 is a C1-C3 alkyl group; R3 is a C1-C4 alkyl group; and R4 is a compound containing o-aminophenyl, m-aminophenyl, p-aminophenyl, pyrrolyl, pyridyl, piperidyl, piperazinyl, pyrazinyl, pyrimidinyl and quinolyl.

Description

technical field [0001] The present invention relates to a small molecule compound, especially a small molecule compound with anti-tumor activity. Background technique [0002] Lung cancer is one of the most common causes of high mortality among many cancers. About 1.6 million people worldwide die from lung cancer every year. Lung cancer is the most common primary malignant tumor. In 2007, through systematic exploration and searching for new oncogenes related to the pathogenesis of non-small cell lung cancer, it was finally discovered that ALK in non-small cell lung cancer was activated and rearranged. So far, a variety of small molecular compounds have been proven to have a certain degree of ALK tyrosine kinase inhibitory activity, and obtained support from in vivo and in vitro studies. In recent years, the FDA has approved some ALK inhibitors for the clinical treatment of non-small cell lung cancer, which has brought new hope for the treatment of patients with ALK-positive...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D401/14A61P35/00A61K31/506
CPCA61P35/00C07D401/12C07D401/14
Inventor 师健友
Owner SICHUAN PROVINCIAL PEOPLES HOSPITAL
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