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Benzimidazole derivatives, preparation method and medicinal use thereof

A technology of phenyl and compound, applied in the field of benzimidazole derivatives and its preparation

Active Publication Date: 2014-04-09
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 derivatives, preparation method and medicinal use thereof
  • Benzimidazole derivatives, preparation method and medicinal use thereof
  • Benzimidazole derivatives, preparation method and medicinal use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] (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

[0088]

[0089] 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

[0091] 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

[0092]

[0093] 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

[0095] 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

[0096]

[0097] Dissolve QR01000-IN-01 (2.2mmol, 1.0eq) and QR01004-IN-03 (3.3mmol, 1.5eq) in 20mL of N-methylpyrrolidone, add triethylamine (4.4mmol, 2.0eq), 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 the pharmaceutical chemistry, and concretely discloses benzimidazole derivatives, and a preparation method and a medicinal use thereof. The benzimidazole derivatives comprise ligustrazine and NO donor derivatives, and the benzimidazole derivatives can rapidly release ligustrazine or NO in vivo, so there is an effective synergistic effect between the benzimidazole derivatives and azilsartan, thereby the benzimidazole derivatives enhances the antihypertension effect, reduces untoward effects, has an ideal protection effect on the liver and kidney of a patient, and fills a gap in the prior art.

Description

technical field [0001] 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 [0002] Hypertension (Hypertension) is the most common cardiovascular disease and 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, calcium channel antagonists, angiotensin converting enzyme inhibitors (ACEI, Puryl class), angiotensin II AT1 receptor blockers (ABR, sartan class), have been continuously discovered and successfully applied in clinical practice. After years of clinical prac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10C07D403/14C07D493/04C07D498/18A61K31/4245A61K31/497A61K31/501A61P9/12A61P9/06A61P9/00
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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