4-methoxy-n,n-bisubstituted phenyl-1,3-benzene bisulfonamide compound and application thereof

A technology of benzenedisulfonamide and dimethylphenyl, applied in the field of anti-platelet aggregation drugs, can solve unseen problems and the like, and achieve the effects of simple preparation method, strong anti-platelet aggregation activity and simple process

Active Publication Date: 2015-05-20
INNOCHEM BEIJING TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are no patent reports on the four 4-methoxy-N,N'-disubstituted phenyl-1,3-benzenedisulfonamide compounds related to the rights of the present invention; there are no relevant literature reports on the present invention

Method used

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  • 4-methoxy-n,n-bisubstituted phenyl-1,3-benzene bisulfonamide compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] A 4-methoxy-N,N'-bis(4-fluorobenzyl)-1,3-benzenedisulfonamide (C 21 N 2 o 5 S 2 f 2 h 20 ) preparation method, the steps are as follows:

[0017] 1) Add 0.63g (5mmol) p-fluorobenzylamine and 0.75g (2.5mmol) 4-methoxy-1,3-benzenedisulfonyl chloride into 10ml ethyl acetate and mix well, react at 0°C for 24h , and the solvent was distilled off to obtain the target crude product;

[0018] 2) Put the above target crude product into a single-necked bottle after drying, add 25ml of acetone, heat to boiling, cool to room temperature, filter and stand still, and then the pure target product can be obtained. After recrystallization with acetone, 0.98 g of transparent target crystals were obtained. Yield: 82.7%, mp: 164.5-166.8C. The group number of the compound in the rabbit platelet aggregation reaction experiment is PN463.

[0019] Infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy ( 1 H-NMR) confirmed the structure of PN463: IR (KBr, cm -1 ):3267...

Embodiment 2

[0021] A 4-methoxy-N,N'-bis(2-fluorobenzyl)-1,3-benzenedisulfonamide (C 21 N 2 o 5 S 2 f 2 h 20 ) preparation method, the steps are as follows:

[0022] 1) Add 0.63g (5mmol) o-fluorobenzylamine and 0.75g (2.5mmol) 4-methoxy-1,3-benzenedisulfonyl chloride into 10ml dichloromethane and mix well, react at 0°C for 30h , and the solvent was distilled off to obtain the target crude product;

[0023] 2) Put the above target crude product into a single-necked bottle after drying, add 30ml of absolute ethanol, heat to boiling, cool to room temperature, filter and stand still, and the pure target product can be obtained. After recrystallization from absolute ethanol, 0.8 g of white target crystals were obtained. Yield: 65.89%, mp: 169.1-171.2 o c. The group number of the compound in the rabbit platelet aggregation reaction experiment is PN466.

[0024] Infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy ( 1 H-NMR) confirmed the structure of PN466: IR (KBr, ...

Embodiment 3

[0026] A 4-methoxy-N,N'-bis(4-fluorophenethyl)-1,3-benzenedisulfonamide (C 23 N 2 o 5 S 2 f 2 h 24 )) preparation method, the steps are as follows:

[0027] 1) Add 0.7g (5mmol) p-fluorophenethylamine and 0.75g (2.5mmol) 4-methoxy-1,3-benzenedisulfonyl chloride into 10ml acetone and mix well, react at 0°C for 24h, The solvent is distilled off to obtain the target crude product;

[0028] 2) Put the above target crude product into a one-necked bottle after drying, add 20ml of methanol, heat to boiling, cool to room temperature, filter and stand still, and then the pure target product can be obtained. After recrystallization from methanol, 0.65 g of white target crystals were obtained. Yield: 52.0%, mp: 151.6-153.1 o c. The group number of the compound in the rabbit platelet aggregation reaction experiment is PN468.

[0029] Infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy ( 1 H-NMR) confirmed the structure of PN468: IR (KBr) cm -1: 3190.62, 1605....

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Abstract

The invention discloses a 4-methoxy-N,N-bisubstituted phenyl-1,3-benzene bisulfonamide compound and an application thereof. The preparation method comprises the following steps: synthesizing a crude target product, namely adding an arylamine compound and 4-methoxy1,3-benzene bisulfonyl chloride into a solvent a and uniformly mixing, reacting for 4-120 hours at minus 5 to 80 DEG C, and distilling to remove the solvent so as to obtain the crude target product; and recrystallizing the crude target product, drying the crude target product, subsequently adding a solvent b, heating till being boiled, cooling down to be the room temperature, filtering and standing so as to obtain a pure target product for preparing a medicament for inhibiting platelet aggregation. The 4-methoxy-N,N-bisubstituted phenyl-1,3-benzene bisulfonamide compound has the advantages that the compound has a high platelet aggregation prevention activity, the preparation method is simple in process and easy to implement, the yield can be 25-99%, and good foundation is made for further study and development of medicaments and applications of the medicaments for platelet aggregation prevention.

Description

technical field [0001] The invention relates to anti-platelet aggregation drugs, especially a 4-methoxy-N, N'-disubstituted phenyl-1,3-benzenedisulfonamide compound and its application. Background technique [0002] Anti-platelet aggregation drugs refer to drugs that can inhibit the adhesion and aggregation of platelets and inhibit the formation of thrombus, so they play an important role in the treatment of thrombosis. [0003] In recent years, in order to find newer, more effective and broader-spectrum anti-platelet aggregation new drugs, the present invention has made further progress on 4-methoxy-N,N'-disubstituted phenyl-1,3-benzenedisulfonamide compounds Research. It was found that four of the compounds have high anti-platelet aggregation activity, and all of them have the prospect of being developed as new anti-platelet aggregation drugs. The 4-methoxy-N,N'-disubstituted phenyl-1,3-benzenedisulfonamide compounds involved in the present invention include: 4-methoxy-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C311/29C07C303/38A61P7/02
Inventor 刘秀杰张庆响
Owner INNOCHEM BEIJING TECH CO LTD
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