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High piperazine acetydrazide derivatives, and preparation and use thereof

A compound and prodrug technology, applied in the field of preparing the homopiperazine acetyl hydrazide derivatives, can solve problems that do not involve possible uses of novel compounds

Active Publication Date: 2009-08-12
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 organic compounds containing homopiperazine reported in the literature do not relate to novel compounds relevant to the present invention and their possible uses

Method used

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  • High piperazine acetydrazide derivatives, and preparation and use thereof
  • High piperazine acetydrazide derivatives, and preparation and use thereof
  • High piperazine acetydrazide derivatives, and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0130] Example 1, (4-benzyl-[1,4]diazepan-1-yl)-acetyl (3-allyl-2-hydroxy Preparation of phenyl-methylene phenyl) hydrazine fumarate

[0131] The reaction flow diagram is as follows:

[0132]

[0133] step 1. Add 50 g (395 mmol) of benzyl chloride and 40 g (400 mmol) of homopiperazine into a 500 ml reaction flask, dissolve them in 300 ml of tetrahydrofuran, and heat to reflux for 5 hours. Cool, filter, and evaporate THF to a small amount. Add 300 ml of water, extract with ethyl acetate, use Na 2 SO 4 dry. Ethyl acetate was distilled off to obtain a crude product, which was separated on silica gel to obtain the pure product 1-benzylhomopiperazine with a yield of 95%.

[0134] Step 2. Under the condition of room temperature and electromagnetic stirring, add 9.5 g (50 mmol) of 1-benzyl homopiperazine and 7.35 g (60 mmol) of 2-chloroacetic ethyl ester and 100 ml of toluene solution to the reaction flask In, add 7.0 g (70 mmol) of triethylamine. After the reaction ...

Embodiment 2

[0140] Example 2, (4-phenyl-[1,4]diazepan-1-yl)-acetyl (2-hydroxyl-methylene Preparation of phenyl)hydrazine fumarate

[0141] The reaction flow diagram is as follows:

[0142]

[0143] step 1. Under the condition of room temperature and electromagnetic stirring, add 8.6 g (50 mmol) of 1-phenylhomopiperazine and 7.35 g (60 mmol) of 2-chloroacetate ethyl ester and 100 ml of toluene solution to the reaction flask In, add 7.0 g (70 mmol) of triethylamine. After the reaction solution was heated to reflux for 8 hours, the reaction was stopped, and the solvent was distilled off. The product was dissolved in 100 ml of ethyl acetate and washed twice with 20 ml of water each. The organic phase was dried over magnesium sulfate, the solvent was evaporated, and the obtained product was separated by column chromatography to obtain 12.4 g of liquid ethyl 4-phenylhomopiperazine-1-acetate with a yield of 92%.

[0144] Proton spectrum (400MHz, CDCl 3 ): 7.18-7.30(m, 5H); 4.08-4.13...

Embodiment 3

[0148] Example 3, (4-phenylethyl-[1,4]diazepan-1-yl)-acetyl (3,5-diallyl- Preparation of 2-Hydroxy-Methylenephenyl)hydrazine Fumarate

[0149] The reaction flow diagram is as follows:

[0150]

[0151]

[0152] step 1. Add 50 g (355 mmol) of 2-chloroethylbenzene and 40 g (400 mmol) of homopiperazine into a 500 ml reaction flask, dissolve them in 300 ml of tetrahydrofuran, and heat to reflux for 5 hours. Cool, filter, and evaporate THF to a small amount. Add 300 ml of water, extract with ethyl acetate, use Na 2 SO 4 dry. Ethyl acetate was distilled off to obtain a crude product, which was separated on silica gel to obtain the pure product 1-phenethylhomopiperazine with a yield of 80%.

[0153] Step 2. Under the condition of room temperature and electromagnetic stirring, react to 1-phenethyl homopiperazine and 7.35 grams (60 mmol) of 1-phenylethyl homopiperazine and 100 milliliters of toluene solution equipped with 10.2 grams (50 mmol) In the bottle, add 7.0 g...

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Abstract

The invention relates to a novel high piperazidine acethydrazide-type derivative indicated by formula I or II. In the formula, the definitions of various symbols are the same as those in the Description. The invention also relates to a method for preparing the high piperazidine acethydrazide-type derivative, the usage of the high piperazidine acethydrazide-type derivative in preparing medicines for curing and / or preventing tumors and / or cancers, and a pharmaceutical composition containing the high piperazidine acethydrazide-type derivative. The high piperazidine acethydrazide-type derivative has effective antitumor activity.

Description

technical field [0001] The present invention relates to a novel class of homopiperazine acetyl hydrazide derivatives, and the invention also relates to a method for preparing said homopiperazine acetyl hydrazide derivatives, which are used in the preparation of / or use in medicines for preventing tumors and / or cancers, and pharmaceutical compositions comprising the homopiperazine acetyl hydrazide derivatives. Background technique [0002] At present, the chemical drugs used in the clinical treatment of advanced cancer are basically non-selective to cancer cells, and the side effects of drugs have brought great harm to the body and mind of cancer patients. Molecular targeted therapy is a new way to selectively treat tumors. Molecular targeted drugs provide feasibility for personalized treatment of cancer patients. The advantage is that it not only reduces toxic side effects, but also prolongs the life of cancer patients. [0003] It has been reported in the literature (see, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D243/08A61K31/551A61P35/00
Inventor 刘现军谭孟群王丹丹
Owner DONGGUAN ZHENGXING BEITE MEDICINE TECH CO LTD
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