1, 2, 4-triazole derivative compound and application thereof in treating inflammatory bowel disease

A technology of derivatives and compounds, applied in the direction of drug combinations, anti-inflammatory agents, digestive system, etc., can solve problems that have not been reported, achieve good preventive or therapeutic effects, and good development prospects

Pending Publication Date: 2021-02-09
王剑
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention innovatively synthesizes 1,2,4-triazole derivatives compounds, in order to obtain brand new compounds for treating gastrointestinal inflammation and ulcerative colitis, and there are no reports of related structures in the prior art

Method used

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  • 1, 2, 4-triazole derivative compound and application thereof in treating inflammatory bowel disease
  • 1, 2, 4-triazole derivative compound and application thereof in treating inflammatory bowel disease
  • 1, 2, 4-triazole derivative compound and application thereof in treating inflammatory bowel disease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1, the preparation of compound 1

[0039] (1), the synthesis of 3-cyclopropyl benzimidic acid methyl ester

[0040]

[0041] Dissolve 3-cyclopropylbenzonitrile (150mmol) in methanol (150mL), cool down to 0°C, then pass HCl gas for about 4 to 5 hours, react overnight at constant temperature, concentrate, and add the obtained solid to diethyl ether for beating to obtain a white Solid 3-cyclopropylbenzimidic acid methyl ester hydrochloride, then the above white solid was added to water (250mL), cooled to 10-20°C, and solid sodium bicarbonate (130mmol) was added in batches to obtain a mixture Dichloromethane (200mL×3) was added to extract, the organic layers were combined, dried by adding anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain methyl 3-cyclopropylbenzimidate, 22.6g, with a yield of 86.0%.

[0042] 1 H-NMR (400MHz, CDCl 3 )δ:1.33(m,2H),1.51(m,2H),2.74(m,1H),3.84(s,3H),7.19-7.28(m,2H),7.64(m,1H),7.81(m ,1H),9.13(s,1H)...

Embodiment 2

[0054] Embodiment 2, the preparation of compound 2

[0055]

[0056] 2-(1-(4-chlorophenyl)-5-(3-cyclopropylphenyl)-1H-1,2,4-triazol-3-yl)phenol (50mmol) in absolute ethanol ( 100ml) solution was stirred thoroughly, then 2-(piperazin-1-yl)ethan-1-ol (120mmol) was added, and after stirring at room temperature for 10-12 hours, petroleum ether (150ml) was added to crystallize the product and filtered. Subsequent purification using flash column chromatography gave off-white solid 2-(5-(3-cyclopropylphenyl)-1-(4-(4-(hydroxymethyl)piperidin-1-yl)phenyl)- 1H-1,2,4-triazol-3-yl)phenol (compound 2), 18.2 g, yield 78.0%. LC-MS (ESI, pos, ion) m / z: 467 [M+H].

Embodiment 3

[0057] Embodiment 3, the preparation of compound 3

[0058]

[0059]2-(1-(4-chlorophenyl)-5-(3-cyclopropylphenyl)-1H-1,2,4-triazol-3-yl)phenol (50mmol) in absolute ethanol ( 100ml) solution was stirred well, then 2-(piperazin-1-yl)ethan-1-ol (120mmol) was added, and after stirring at room temperature for 10-12 hours, petroleum ether (150ml) was added to crystallize the product and filtered. Subsequent purification using flash column chromatography afforded 2-(5-(3-cyclopropylphenyl)-1-(4-(4-propylpiperidin-1-yl)phenyl)-1H-1 as an off-white solid ,2,4-triazol-3-yl)phenol (compound 3), 17.0 g, yield 71.0%. LC-MS (ESI, pos, ion) m / z: 479 [M+H].

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Abstract

The invention belongs to the field of medicines, and relates to a 1, 2, 4-triazole derivative compound and application thereof in treatment of inflammatory bowel diseases. The structural formula of the 1, 2, 4-triazole derivative compound is shown as a formula I. In a 3% dextran sodium sulfate induced mouse ulcerative colitis model, the compound prepared by the invention has a remarkable improvement effect.

Description

technical field [0001] The invention belongs to the field of medicine and relates to a 1,2,4-triazole derivative compound and its application in treating inflammatory bowel disease. Background technique [0002] Inflammatory bowel disease involves chronic inflammation of all or part of the digestive tract. The two main forms of inflammatory bowel disease are ulcerative colitis and Crohn's disease. The most common symptoms of ulcerative colitis are diarrhea and blood in the stool. The disease is of unknown etiology, the result of an interaction of environmental, genetic, and microbial factors, and is characterized by periodic quiescence and outbreaks. Ulcerative colitis has no sex difference, and the peak age of onset is between 30 and 40 years old. Currently, the incidence and prevalence of ulcerative colitis are increasing worldwide. [0003] Clinically, the purpose of drug therapy for ulcerative colitis is mainly to relieve clinical symptoms, that is, to stop blood in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08C07D401/10A61P1/04A61P1/00A61P29/00
CPCA61P1/00A61P1/04A61P29/00C07D249/08C07D401/10
Inventor 王健
Owner 王剑
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