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Aryl formyl piperazine compound and its preparing method and use in medicine production

A technique for aroylpiperazines and compounds, which is applied in the field of preparation of the aroylpiperazines, can solve problems such as weakening effects, and achieve the effects of mild reaction conditions, strong antiarrhythmic activity, and easy-to-obtain raw materials

Inactive Publication Date: 2010-05-12
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has two major disadvantages: proarrhythmia and reduced effect on increased heart rate and stimulation of beta-receptors

Method used

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  • Aryl formyl piperazine compound and its preparing method and use in medicine production
  • Aryl formyl piperazine compound and its preparing method and use in medicine production
  • Aryl formyl piperazine compound and its preparing method and use in medicine production

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Example 1: 2-thienyl-[1-(4-(3-methyl)phenyl)piperazine]methanone hydrochloride

[0072]

[0073] (1) Preparation of 1-(3-methylphenyl)piperazine hydrochloride: add m-toluidine 1.07g (0.01mol) in nitrogen mustard 1.785g (0.01mol), anhydrous K 2 CO 3 0.69g (0.005mol) and 20ml of n-butanol, stirred and refluxed for 48 hours. Concentrate, refrigerate, precipitate a solid, filter it out, and recrystallize the solid from absolute ethanol to obtain 1.05 g of white flaky crystals, m.p.: 127-129°C (dec), yield: 49.41%.

[0074] (2) Preparation of the title compound: Add 10ml of chloroform to 0.64g (0.005mol) of thiophene-2-carboxylic acid, add 2.38g (0.02mol) of SOCl dropwise 2 10ml of chloroform solution, reflux for 1 hour. Concentrate to dryness and dissolve in 15ml of chloroform to obtain a solution of acid chloride in chloroform for use.

[0075] Add 10ml of chloroform to 0.53g (0.0025mol) of 1-(3-methyl)phenylpiperazine hydrochloride, stir at room temperature, slowly...

Embodiment 2

[0079] Example 2: 2-benzofuryl-[1-(4-(3-methyl)phenyl)piperazine]methanone

[0080]

[0081] Prepared according to the method of Example 1, substituting benzofurancarboxylic acid for thiophene-2-carboxylic acid in step (2) to obtain 0.29 g of the title compound as pale yellow flaky crystals, m.p.: 167-168°C, yield: 45.31%.

[0082] IR(KBr), cm -1 : 2823, 1612, 1443, 1432, 1248, 953, 773, 748, 689

[0083] EI-MS: m / z320: M m / z146:

[0084] 1 H-NMR (CDCl 3 ), δ: 7.67 (dd, 1H, ), 7.54(dd, 1H, Ar-H), 7.42(t, 1H, Ar-H), 7.35(s, 1H, Ar-H), 7.31(t, 1H, Ar-H), 7.18(t, 1H, ), 6.75(t, 3H, ), 4.01(s, 4H, ), 3.27(d, 4H, ), 2.33(s, 3H, -C H 3 )ppm.

Embodiment 3

[0085] Example 3: 3-Chlorophenyl-[1-(4-(3-methyl)phenyl)piperazine]methanone hydrochloride

[0086]

[0087] According to the method of Example 1, m-chlorobenzoic acid was used instead of thiophene-2-carboxylic acid in step (2) to obtain 0.30 g of the title compound as a white loose solid. m.p.: 199-200°C, yield: 34.19%.

[0088] IR(KBr), cm -1 : 2998, 2328, 1655, 1427, 1256, 1110, 1035, 926, 767

[0089] EI-MS: m / z314: M m / z146:

[0090] 1 H-NMR (CDCl 3 ), δ: 7.68(s, 1H, Ar-H), 7.60(dd, 1H, Ar-H), 7.45-7.49(m, 2H, Ar-H), 7.38-7.43(m, 2H, Ar-H ), 7.33-7.38(m, 1H, Ar-H), 7.28-7.31(d, 1H, Ar-H), 4.39(s, 4H, ), 3.49(d, 4H, ), 2.42(s, 3H, - CH 3 )ppm.

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PUM

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Abstract

The present invention discloses one kind of aryl formyl piperazine compound and its preparation process and application in preparing medicine. The compound and its medicinal salt have the general expressions shown. The compound may be used in preparing medicine for arrhythmia. The compound has rich material source, mild reaction condition and simple preparation process and post-treatment.

Description

technical field [0001] The invention relates to an aroylpiperazine compound, and also relates to a preparation method and application of the aroylpiperazine compound. Background technique [0002] At present, there are four types of antiarrhythmic drugs in clinical use, but there is a lack of effective and safe drugs in clinical practice. Most antiarrhythmic drugs produce arrhythmic side effects in clinical use. However, since the discovery of potassium ion channels in the early 1990s and the development of drugs based on this, in the past ten years, great changes have taken place in the drug treatment of arrhythmia. Global new drug developers have paid more attention to antiarrhythmic drugs The safety and efficacy of the CAST experiment in 1998 made its research focus shift from class I antiarrhythmic drugs to class III antiarrhythmic drugs, and the research on potassium ion channel blockers has made great progress. The antiarrhythmic drugs reported later are almost all po...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/38C07D307/85C07D295/192A61K31/496A61P9/06
Inventor 尤启冬杜吕佩李敏勇夏霖
Owner CHINA PHARM UNIV
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