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Benzimidazole derivative, and preparation method and pharmaceutical applications thereof

A technology of use, pharmacy, applied in drug combination, cardiovascular system diseases, organic chemistry, etc.

Active Publication Date: 2016-01-13
WUHAN LL SCI & TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The development of tetramethylpyrazine AT1 receptor blockers can not only effectively enhance the antihypertensive effect of AT1 receptor blockers, but also achieve effective protection of liver and kidney, and also have potential therapeutic significance for other cardiovascular diseases. There is no related report in the prior art

Method used

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  • Benzimidazole derivative, and preparation method and pharmaceutical applications thereof
  • Benzimidazole derivative, and preparation method and pharmaceutical applications thereof
  • Benzimidazole derivative, and preparation method and pharmaceutical applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] (Isopropyloxycarbonyloxy)methyl-2-ethoxy-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazole)- Synthesis of 3-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate

[0089]

[0090] Dissolve QR01000-IN-01 (2.2 mmol, 1.0 equivalent) and QR01002-IN-01 (3.3 mmol, 1.5 equivalent) in 20 mL of N-methylpyrrolidone, add triethylamine (4.4 mmol, 2.0 equivalent), and heat to 65 °C, the reaction was monitored by TLC, and the reaction was complete. Water and ethyl acetate were added to the reaction liquid, extraction and separation were carried out, and the organic layer was washed with water and saturated brine. The organic layer was dried and concentrated, and purified by column chromatography to obtain the target compound QR01002, whose structure was double-confirmed by LCMS spectrum and H NMR spectrum.

Embodiment 2

[0092] 1-(isopropyloxycarbonyloxy)ethyl-2-ethoxy-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazole Synthesis of )-3-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate

[0093]

[0094] Dissolve QR01000-IN-01 (2.2 mmol, 1.0 equivalent) and QR01003-IN-01 (3.3 mmol, 1.5 equivalent) in 20 mL of N-methylpyrrolidone, add triethylamine (4.4 mmol, 2.0 equivalent), and heat to 65 °C, the reaction was monitored by TLC, and the reaction was complete. Water and ethyl acetate were added to the reaction liquid, extraction and separation were carried out, and the organic layer was washed with water and saturated brine. The organic layer was dried and concentrated, and purified by column chromatography to obtain the target compound QR01003, whose structure was double confirmed by LCMS spectrum and H NMR spectrum.

Embodiment 3

[0096] Acetoxyethyl-2-ethoxy-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol)-3-yl)biphenyl- Synthesis of 4-yl]methyl}-1H-benzimidazole-7-carboxylate

[0097]

[0098] Dissolve QR01000-IN-01 (2.2 mmol, 1.0 equivalent) and QR01004-IN-03 (3.3 mmol, 1.5 equivalent) in 20 mL of N-methylpyrrolidone, add triethylamine (4.4 mmol, 2.0 equivalent), and heat to 65 °C, the reaction was monitored by TLC, and the reaction was complete. Water and ethyl acetate were added to the reaction liquid, extraction and separation were carried out, and the organic layer was washed with water and saturated brine. The organic layer was dried and concentrated, and purified by column chromatography to obtain the target compound QR01004, whose structure was double-confirmed by LCMS spectrum and H NMR spectrum.

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PUM

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Abstract

The invention belongs to the technical field of pharmaceutical chemistry, and more specifically discloses a benzimidazole derivative, and a preparation method and pharmaceutical applications thereof. The benzimidazole derivative comprises ligustrazine and a NO donor derivative. In vivo, ligustrazine or NO can be released from the benzimidazole derivative quickly, so that effective synergistic effect with Azilsartan is achieved, anti-hypertension curative effect is improved, adverse reaction is reduced, ideal protection effect on livers and kidneys of patients is achieved, and the blank of the prior art is filled.

Description

[0001] This application is a divisional application for the filing date of February 4, 2013, the application number: 201310042669.2, the name of the invention: benzimidazole derivatives and their preparation methods and medical applications. technical field [0002] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a class of benzimidazole derivatives, a preparation method and a medical application thereof. Background technique [0003] Hypertension (Hypertension) is the most common cardiovascular disease, and it is also a major risk factor leading to increased morbidity and mortality of congestive heart failure, stroke, coronary heart disease, renal failure, and aortic aneurysm. Antihypertensive drugs play a key role in the treatment and prevention of hypertensive diseases. With the deepening understanding of the pathogenesis of hypertension, many antihypertensive drugs with better efficacy, such as diuretics, β-blockers, calc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14A61P9/12A61P9/06A61P9/00
CPCC07D403/14C07D413/10C07D413/14C07D493/04C07D498/18
Inventor 葛建马建义项光亚王玮王朝东
Owner WUHAN LL SCI & TECH DEV
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