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Piperazidine or homopiperazine oxalyl hydrazine class compound, preparation and use thereof

A compound, selected technology, applied in the direction of active ingredients of heterocyclic compounds, organic chemistry, drug combination, etc., can solve the problem of incomplete research on the relationship between the structure and properties of compounds

Active Publication Date: 2009-10-28
DONGGUAN ZHENGXING BEITE MEDICINE TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the compounds reported in the literature are only limited to piperazine ring acetyl hydrazide heterocyclic compounds, and there is no thorough research on the relationship between the structure and properties of the compounds.

Method used

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  • Piperazidine or homopiperazine oxalyl hydrazine class compound, preparation and use thereof
  • Piperazidine or homopiperazine oxalyl hydrazine class compound, preparation and use thereof
  • Piperazidine or homopiperazine oxalyl hydrazine class compound, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0213] Example 1, (4-benzyl-[1,4]diazepan-1-yl)-oxo-acetyl (3-allyl- Preparation of 2-hydroxy-methylenephenyl)hydrazine and its salt

[0214] The reaction scheme is outlined as follows:

[0215]

[0216]

[0217] step 1. Under the condition of 0 ℃ and electromagnetic stirring, in the reaction flask equipped with 1.9 g (10 mmol) of 4-benzyl homopiperazine and 1.11 g (11 mmol) of triethylamine and 50 ml of toluene, A solution of 2.0 g (15 mmol) ethyl oxalyl chloride in dichloromethane was added dropwise. After completion of the dropwise addition, stir at room temperature for 8 hours. After the reaction, add 50 ml of water, separate the organic layer, and use Na 2 SO 4 dry. After filtration and concentration, the obtained product was directly used in the next reaction with a yield of 95%.

[0218] Step 2. 2.94 g (10 mmol) of 4-benzyl homopiperazine oxaloethyl ester was added to a 300 ml round bottom flask, and 0.56 g (15 mmol) of 85% hydrazine hydrate was slowly...

Embodiment 2

[0221] Embodiment 2, (4-benzyl-piperidin-1-yl)-oxo-acetyl (2-hydroxyl-methylene phenyl) hydrazine and its salt preparation

[0222] The reaction scheme is outlined as follows:

[0223]

[0224] step 1. Under the condition of 0 ℃ and electromagnetic stirring, in the reaction flask equipped with 1.75 g (10 mmol) of 4-benzylpiperidine and 1.11 g (11 mmol) of triethylamine and 50 ml of toluene, gradually A dichloromethane solution of 2.0 g (15 mmol) ethyl oxalyl chloride was added dropwise. After completion of the dropwise addition, stir at room temperature for 8 hours. After the reaction, add 50 ml of water, separate the organic layer, and use Na 2 SO 4 dry. After filtration and concentration, the obtained product was directly used in the next reaction with a yield of 85%.

[0225] Step 2. 2.75 g (10 mmol) of 4-benzylpiperidine-1-oxaloethyl ester was added to a 300 ml round bottom flask, and 0.56 g (15 mmol) of 85% hydrazine hydrate was slowly added dropwise under ...

Embodiment 3

[0228] Example 3, (pyridine-3-methyl-piperazin-1-yl)-oxo-acetyl (3,5-dichloro-2-hydroxyl- Preparation of methylphenyl) hydrazine and its salt

[0229] The reaction scheme is outlined as follows:

[0230]

[0231] step 1. Under the condition of 0 ℃ and electromagnetic stirring, add 1.77 g (10 mmol) of [4-(1-pyridine-3-methyl)] piperazine- and 1.11 g (11 mmol) of triethylamine In a reaction flask with 50 ml of toluene, 2.0 g (15 mmol) of monoethyl oxalyl chloride in dichloromethane was added dropwise. After completion of the dropwise addition, stir at room temperature for 8 hours. After the reaction, add 50 ml of water, separate the organic layer, and use Na 2 SO 4 dry. After filtration and concentration, the obtained product was directly used in the next reaction with a yield of 90%.

[0232] Step 2. [4-(1-pyridine-3-methyl)]piperazine-1-oxalyl ethyl ester of 2.77 grams (10 mmoles) was added in the round-bottomed flask of 300 milliliters, slowly dripped 0.56 gram...

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PUM

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Abstract

The invention relates to a novel piperazidine or homopiperazine oxalyl hydrazine class compound as represented by formula I, wherein each symbol has meanings defined in the description. The invention further relates to the preparation of the piperazidine or homopiperazine oxalyl hydrazine class compound, use of the piperazidine or homopiperazine oxalyl hydrazine class compound in preparing medicament for treating and / or preventing tumor and / or cancer, medicament composition containing the piperazidine or homopiperazine oxalyl hydrazine class compound. The piperzzidine or homopiperazine oxalyl hydrazine class compound has effective anti-tumor activity.

Description

technical field [0001] The present invention relates to a class of novel piperazine or homopiperazine oxalyl hydrazide compounds, and the present invention also relates to a method for preparing said piperazine or homopiperazine oxalyl hydrazide compounds, said piperazine or homopiperazine oxalyl hydrazide Use of hydrazine compounds in preparing medicines for treating and / or preventing tumors and / or cancers, and pharmaceutical compositions containing the piperazine or homopiperazine oxalazide compounds. Background technique [0002] Heterocyclic compounds containing piperazine or homopiperazine are important intermediates or final products of drug synthesis, and all have various pharmaceutical activities, especially anticancer activities (see, for example, WO 2006128173, WO 2008134474), Therefore, heterocyclic compounds containing piperazine and homopiperazine have attracted more and more attention in the design, screening, and synthesis of a new generation of high-efficienc...

Claims

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Application Information

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IPC IPC(8): C07D295/185C07D295/194C07D295/108C07D211/16C07D213/40C07D241/04A61K31/551A61K31/445A61K31/495A61K31/496A61P35/00A61P35/02
Inventor 刘现军谭孟祥王丹丹
Owner DONGGUAN ZHENGXING BEITE MEDICINE TECH CO LTD
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