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Triazolone compound as well as preparation method and application thereof

A compound and general formula technology, applied in the field of triazolone derivatives and their preparation, can solve the problems of low specificity, poor selectivity, toxic and side effects, etc.

Inactive Publication Date: 2010-06-09
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

They have obvious clinical therapeutic effects, but their disadvantages are: low specificity and poor selectivity, leading to obvious toxic and side effects, and prone to serious cancer multidrug resistance

Method used

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  • Triazolone compound as well as preparation method and application thereof
  • Triazolone compound as well as preparation method and application thereof
  • Triazolone compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] 1-(4-aminophenyl)-4,5-dihydro-1,2,4-triazol-5-one (V)

[0054]

[0055] A 100 mL round bottom flask was charged with 2.06 g (10 mmol) of compound IV, 0.1 g of 5% Pd / C catalyst and 60 mL of methanol. The reaction system was hydrogenated at room temperature and pressure for 1 hour with stirring. The catalyst in the reaction mixture was removed by filtration, and the filtrate was evaporated to remove the solvent on a rotary evaporator to obtain colorless crystals, namely product V. 1.72g, 98%. IR(KBr), 3342, 3321, 1645cm -1 .

Embodiment 2

[0057] 1-(4-Aminophenyl)-4-benzyl-4,5-dihydro-1,2,4-triazol-5-one (VII-1)

[0058]

[0059] 1.76g (10mmol) of compound V was added to a 100mL round bottom flask, dissolved in 30mL of dry THF, and 0.4g (10mmol, 60%) of solid NaH was added in batches under stirring, and stirred for half an hour. Then 1.27 g (10 mmol) of BnCl VI-1 was added and stirred overnight at room temperature. The solid in the reaction system was removed by filtration, and the solvent was evaporated from the filtrate on a rotary evaporator to obtain a colorless solid, which was recrystallized from absolute ethanol to obtain product VII-1. Colorless crystals, 2.23g, yield 84%. IR(KBr), 3345, 3328, 1641cm -1 .

[0060] Compound VI-1 is one of the compounds of general formula VI, likewise compound VII-1 is one of the compounds of general formula VII.

Embodiment 3-17

[0062] Referring to the operation of Example 2, VI-2 to VI-16 in the following table replaced VI-1 in Example 2, and the rest of the operations were the same as in Example 2 to obtain compounds VII-2 to VII-16.

[0063] Compounds VI-2 to VI-16 belong to the compounds of the general formula VI, likewise compounds VII-2 to VII-16 belong to the compounds of the general formula VII.

[0064] Reality

Example sequence

No

Produce

Rate / %

VI

VII

3

82

VI-2: 2-

Chlorobenzyl chloride

VII-2: 1-(4-aminophenyl)-4-(2-chloro)benzyl-4,

5-Dihydro-1,2,4-triazol-5-one

4

83

VI-3: 3-A

yl-2-nitrobenzyl

chlorine

VII-3: 1-(4-aminophenyl)-4-(3-methyl-2-nitrate

Base) benzyl-4,5-dihydro-1,2,4-triazol-5-one

5

80

VI-4: 3-fluoro

Benzyl chloride

VII-4: 1-(4-aminophenyl)-4-(3-fluoro)benzyl-4, ...

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PUM

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Abstract

The invention relates to the field of medicaments relevant to cancer resistance, in particular to a triazolone derivative with the general formula I and cancer resistance, a preparation method, a medicament composition and an application. Definitions of all groups are stated in the specification.

Description

technical field [0001] The invention relates to the field of medicines related to anticancer. Specifically, the present invention relates to triazolone derivatives with anticancer properties, their preparation methods, and pharmaceutical compositions containing them. Background technique [0002] Cancer is the primary disease that threatens human life. According to statistics, the total number of cancer deaths in the world reaches 7 million people every year. In my country, more than 1 million patients die from cancer every year, and it is gradually increasing. It has become the first cause of death in urban population. At present, the traditional medicines for the treatment of cancer diseases clinically in my country include: alkylating agents (such as phosphoramide), anti-metabolites (such as 5-fluorouracil), antibiotics (such as idarubicin), anti-cancer herbal medicines (such as Hydroxycamptothecin). They have obvious therapeutic effects in clinic, but their disadvantage...

Claims

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Application Information

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IPC IPC(8): C07D249/12C07D403/12C07D417/12A61K31/4196A61K31/427A61P35/00
Inventor 赵桂龙徐为人刘兵王润玲刘巍汤立达张士俊王玉丽谭初兵刘冰妮
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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