Benzimidazole compound and its preparing method and use in medicine production

A technology of benzimidazole and compound, applied in the field of drug synthesis, can solve problems such as weakened effect

Inactive Publication Date: 2007-04-11
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 eff

Method used

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  • Benzimidazole compound and its preparing method and use in medicine production
  • Benzimidazole compound and its preparing method and use in medicine production
  • Benzimidazole compound and its preparing method and use in medicine production

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1: 1-Benzyl-N-p-tolyl-1H-benzimidazol-2-amine

[0067]

[0068] (1) Synthesis of intermediate 1H-benzimidazolone: ​​Add 6.00 g (0.10 mol) of urea and 50 ml of n-amyl alcohol to 5.40 g (0.05 mol) of o-phenylenediamine, and stir and reflux for 10 hours. Cool to room temperature, filter out, recrystallize with absolute ethanol, and dry under infrared light to obtain 5.12 g of light yellow flaky crystals (1H-benzimidazolone), m.p.: 320-322°C, yield: 76.42%.

[0069] (2) Synthesis of intermediate 2-chloro-1H-benzimidazole: add 40mlPOCl to 5.36g (0.04mol) of 1H-benzimidazolone 3 After stirring and refluxing for 3 hours, dry HCl gas was passed into the reflux state for 3 hours. After concentrating the reaction solution, add 40 ml of distilled water while stirring in an ice-water bath to obtain a light yellow turbid liquid, which is filtered, and the filtrate is adjusted to a pH of 8-9 with concentrated ammonia water, and solids are precipitated, and refrigerated ov...

Embodiment 2

[0075] Example 2: 1-Benzyl-N-m-tolyl-1H-benzimidazol-2-amine

[0076]

[0077] By the method of step (4) in Example 1, replace p-methylaniline with m-methylaniline, and 1-benzyl-2-chloro-1H-benzimidazole (according to Example 1 steps (1)~(3) Preparation, the same below) reaction, the title compound was obtained as white powder 0.55g. m.p.: 182-184°C, yield: 87.86%.

[0078] IR(KBr), cm -1 : 3439, 3379, 3037, 1617, 1527, 1492, 1251, 857, 780, 735

[0079] EI-MS: m / z313: m / z222: m / z207(BasePeak):

[0080] 1 H-NMR (DMSO-d6), δ: 8.96 (s, 1H, -NH-), 7.70 (d, 1H, J=8.16Hz, Ar-H), 7.64 (s, 1H, Ar-H), 7.41 (dd, 1H, J=0.71, 7.65Hz, Ar-H), 7.14-7.33(m, 7H, Ar-H), 6.94-7.04(m, 2H, Ar-H), 6.76(d, 1H, J =7.42Hz, Ar-H), 5.53(s, 2H, -NCH 2 ph), 2.30(s, 3H, phCH 3 )ppm.

Embodiment 3

[0081] Example 3: 1-Benzyl-N-(3,4-dimethyl)phenyl-1H-benzimidazol-2-amine

[0082]

[0083]According to the method of step (4) in Example 1, 3,4-dimethylaniline was used instead of p-methylaniline, and 1-benzyl-2-chloro-1H-benzimidazole was reacted to obtain the title compound as a white flocculent Solid 0.31 g. m.p.: 178-179°C, yield: 61.16%.

[0084] IR(KBr), cm -1 : 3481, 1617, 1523, 1251, 819, 739, 713

[0085] EI-MS: m / z327: m / z236: m / z221(Base Peak):

[0086]

[0087] 1 H-NMR (DMSO-d6), δ: 7.63 (dd, 1H, J=2.25, 2.34Hz, Ar-H), 7.53 (d, 1H, J=1.99Hz, Ar-H), 7.38(d, 1H , J=7.58Hz, Ar-H), 7.28-7.33(m, 2H, Ar-H), 7.23-7.26(m, 1H, Ar-H), 7.14-7.20(m, 3H, Ar-H), 6.99-7.08(m, 2H, Ar-H), 6.94-6.99(t, 1H, Ar-H), 5.51(s, 2H, -NCH 2 ph), 2.21(s, 3H, phCH 3 ), 2.17 (s, 3H, ph-CH 3 )ppm

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Abstract

The present invention discloses one kind of benzimidazole compound and its prepare and application in producing medicine. The compound has the general expression as shown. The compound is potassium ion channel retardant, has arrhythmia treating activity and no side effect, and may be used in preparing medicine for arrhythmia. The preparation process has facile material and mild reaction condition.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to a benzimidazole compound. The invention also relates to a preparation method of the compound and an application of the compound in preparing antiarrhythmic drugs. 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 bloc...

Claims

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Application Information

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IPC IPC(8): C07D235/30C07D235/28A61K31/4184A61K31/496A61P9/06
Inventor 尤启冬杜吕佩杨倩李敏勇夏霖
Owner CHINA PHARM UNIV
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