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Benzenesulfonyl piperazine compounds or benzoyl piperazine compounds, preparation methods and uses thereof

A kind of compound, the technology of piperazine, be used in the pharmaceutical composition that comprises described compound, prepare described compound field

Active Publication Date: 2012-12-26
DONGGUAN ZHENGXING BEITE MEDICINE TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, researchers such as Professor Paul J. Hergenrother subsequently reported that after high-dose administration, PAC-1 had significant neurotoxicity symptoms in mice (mainly manifested as jumping, tremor, and unsteady standing, etc.)

Method used

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  • Benzenesulfonyl piperazine compounds or benzoyl piperazine compounds, preparation methods and uses thereof
  • Benzenesulfonyl piperazine compounds or benzoyl piperazine compounds, preparation methods and uses thereof
  • Benzenesulfonyl piperazine compounds or benzoyl piperazine compounds, preparation methods and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0139] Example 1, 2-(4-(4-(4-methylpiperazin-1-yl)benzenesulfonyl)piperazin-1-yl)-acetyl (3-allyl-2-hydroxyl-methylene The preparation of phenyl) hydrazine

[0140] The reaction process is as follows:

[0141]

[0142] Step 1. Add piperazine (25.8 g, 0.3 mol) and DCM (50 ml) into the reaction flask under a water bath at room temperature, and stir to gradually dissolve the solid to form a suspension. Then slowly add DCM (50ml) of p-bromobenzenesulfonyl chloride (25.5g, 0.1mol) dropwise, stir for 30min after completion of the dropwise addition, TLC monitoring reaction ends, then add tap water (50ml) to wash once, separate the DCM layer, water Layer was extracted with DCM (50ml), separated, and the DCM layers were combined, and the DCM was removed by rotary evaporation, and a solid was precipitated. The solid was basically dissolved with methanol (30ml), and then tap water (100ml) was slowly added dropwise. A large amount of solids were precipitated, filtered, and filtered. ...

Embodiment 2

[0147] Embodiment 2, the preparation of 2-(4-(4-morpholinylbenzenesulfonyl)piperazin-1-yl)-acetyl(3-allyl-2-hydroxyl-methylenephenyl)hydrazine

[0148] The reaction process is as follows:

[0149]

[0150] Step 1. Add (3.05g, 10mmol) compound 1 (see Example 1 for the preparation method), N-methylpyrrolidone (10ml) and morpholine (2.61g, 30mol) into the reaction flask, stir at room temperature to dissolve all the solids, Then put the reaction bottle into an oil bath, seal it with a balloon, and raise the temperature to 170°C for a constant temperature reaction until the raw materials disappear. After 15 hours of reaction, the reaction was completed, cooled to room temperature, then poured into a 50ml beaker, added DCM (10ml), stirred evenly, then added tap water (100ml), extracted, separated the DCM layer, and used tap water (4*20ml) After washing four times, the DCM layer was separated, dried over anhydrous magnesium sulfate (2 g), filtered, and the filter cake was washed ...

Embodiment 3

[0154] Example 3, Preparation of 2-(4-(p-toluenesulfonyl)piperazin-1-yl)-acetyl(3-allyl-2-hydroxyl-methylenephenyl)hydrazine

[0155] The reaction process is as follows:

[0156]

[0157] Step 1. Add piperazine (25.8 g, 0.3 mol) and DCM (50 ml) into the reaction flask under a water bath at room temperature, and stir to gradually dissolve the solid to form a suspension. Then slowly add DCM (50ml) of p-toluenesulfonyl chloride (25.5g, 0.1mol) dropwise, stir for 30min after completion of the dropwise addition, TLC monitoring reaction ends, then add tap water (50ml) to wash once, separate DCM layer, water layer Extract with DCM (50ml), separate, combine the DCM layers, remove the DCM by rotary evaporation, and precipitate a solid, which is basically dissolved with methanol (30ml), and then slowly add tap water (100ml) dropwise, a large amount of solids precipitate, filter, filter cake Rinse with water. After infrared drying, 24 g of white solid was obtained; yield: 80%. Mass...

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Abstract

The present invention relates to benzenesulfonyl piperazine compounds represented by a formula I or benzoyl piperazine compounds represented by a formula II, or pharmaceutically acceptable salts, solvates, stereoisomers or precursor drugs thereof, wherein various symbols are described in an instruction. The present invention further relates to preparation methods for the compounds, uses of the compounds in preparation of drugs for treatment and / or prevention of tumors and / or cancers, methods for treatment and / or prevention of tumors and / or cancers by using the compounds, and drug compositions containing the compounds having an effective treatment and / or prevention amount. The compounds of the present invention have characteristics of effective anticancer activity and low toxicity.

Description

technical field [0001] The present invention relates to a class of benzenesulfonyl or benzoylpiperazine compounds, and the present invention also relates to a method for preparing the compound, and the use of the compound in the preparation of medicines for treating and / or preventing tumors and / or cancers , and pharmaceutical compositions comprising said compounds. Background technique [0002] As a worldwide disease, tumor has become an important disease that threatens human health and survival and causes human death. Chemotherapy is the main treatment for advanced cancer. However, currently used chemotherapy drugs are basically non-selective to cancer cells. While killing cancer cells, they also kill a large number of normal cells, causing great physical and mental harm to cancer patients. [0003] Molecular targeted therapy is a new way to selectively treat tumors, and molecular targeted drugs provide feasibility for personalized treatment of cancer patients. In recent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/26C07D295/192A61K31/5377A61K31/496A61K31/495A61P35/00A61P35/02
Inventor 钟宪斌程笠人谭孟群唐升斌马志柯
Owner DONGGUAN ZHENGXING BEITE MEDICINE TECH CO LTD
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