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6-piperazinemethyl-7-hydroxybenzofuran compound and medical application thereof

A compound and hydroxybenzene technology, applied in the field of compounds and their medicinal uses, can solve problems such as difficulty in controlling intestinal symptoms, and achieve the effect of a simple synthesis method

Active Publication Date: 2019-06-14
SHENYANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, Xenical is the best-selling pancreatic lipase inhibitor in the market, which has the characteristics of strong activity and good stability, but it also has the disadvantages of difficult-to-control intestinal symptoms, greasy stools, vomiting and abdominal distension.

Method used

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  • 6-piperazinemethyl-7-hydroxybenzofuran compound and medical application thereof
  • 6-piperazinemethyl-7-hydroxybenzofuran compound and medical application thereof
  • 6-piperazinemethyl-7-hydroxybenzofuran compound and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Example 1: Preparation of 6-[(4-phenylpiperazin-1-yl)methyl]-7-hydroxybenzofuran (T01):

[0064] Add 4.0 g (0.030 mol) of 7-hydroxybenzofuran, 4.9 g (0.030 mol) of 1-phenylpiperazine, 1.0 g (0.033 mol) of paraformaldehyde, and 1 mL of glacial acetic acid into the reaction flask, use an appropriate amount of ethanol as a solvent, and heat Reflux for 4~8h, TLC monitors the reaction process, after the reaction is completed, cool down, and remove ethanol by rotary evaporation to obtain a yellow oil, which is separated and purified by column chromatography with ethyl acetate:petroleum ether (1:5) as eluent, The solvent was removed by rotary evaporation, and 2.6 g of a light yellow solid was precipitated by freezing, with a yield of 28.2%. ESI-MS m / z: 309.2; 1 H-NMR (CDCl 3 ) δ(ppm): 2.62-2.68 (4H, m), 3.16-3.22 (4H, m), 3.78 (2H, s), 6.70(1H, m), 6.80(1H, d, J =8.1 Hz), 6.98-7.08(2H, m), 7.16-7.22 (4H, m),7.68(1H, d, J =8.1 Hz). Example 2: Preparation of 6-{[4-(4-methyl...

Embodiment 2

[0065] According to the preparation method of Example 1, a light yellow solid was obtained with a yield of 26.1%. ESI-MS m / z: 351.4; 1 H-NMR (CDCl 3 ) δ(ppm): 2.27 (3H, s), 2.65-2.70 (4H, m), 3.20-3.32 (4H, m), 3.80 (2H, s), 6.70(1H, d, J =8.1 Hz), 6.96 (2H, d, J = 8.2 Hz), 7.00-7.06(2H, m), 7.16(2H, d, J =8.2 Hz), 7.72(1H, d, J =8.1 Hz).

Embodiment 3

[0066] Example 3: Preparation of 6-{[4-(2-methylphenyl)piperazin-1-yl]methyl}-7-hydroxybenzofuran (T03):

[0067] According to the preparation method of Example 1, a light yellow solid was obtained with a yield of 24.9%. ESI-MS m / z: 351.4; 1 H-NMR (CDCl 3 ) δ(ppm): 2.28 (3H, s), 2.58-2.66 (4H, m), 3.25-3.34 (4H, m), 3.86 (2H, s), 6.56-6.65 (1H, m), 6.77(1H , d, J =8.1 Hz), 6.94-7.03(3H, m), 7.08-7.13(2H,m), 7.82(1H, d, J =8.1 Hz).

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Abstract

The invention provides a 6-piperazinemethyl-7-hydroxybenzofuran compound and medical application thereof, and relates to a compound and medical application thereof. The compound comprises the 6-piperazinemethyl-7-hydroxybenzofuran compound shown as a formula I as well as stereoisomers and pharmaceutically acceptable salts of the compound. The compound has an obvious pancrelipase inhibition effect.The compound is a compound shown as the formula I; the formula I is shown in the description, wherein Ar can be independently selected from phenyl, C1-C4 alkyl-substituted phenyl, C1-C4 alkoxy-substituted phenyl and halogen-substituted phenyl; furthermore, Ar is independently selected from phenyl, 4-methylphenyl, 2-methylphenyl, 4-methoxyphenyl, 4-chlorphenyl, 2-chlorphenyl, 4-bromophenyl, 4-fluorophenyl and 2-fluorophenyl. The compound contains a high-selectivity and long-acting gastrointestinal lipase inhibitor, is applicable to obesity, and is suitable for obese people including healthy obese people and obese people with non-insulin-dependent diabetes mellitus.

Description

technical field [0001] The present invention relates to a compound and its medical application, in particular to 6-piperazinemethyl-7-hydroxybenzofuran compound and its medical application. Background technique [0002] Obesity is a common disease worldwide. In recent years, the incidence of obesity has been increasing all over the world, especially in developed countries. Due to the rapid development of the economy and the continuous improvement of living standards, the problems of insufficient exercise and relative excess energy intake have always existed in the lifestyle of modern people, which has led to the energy intake of many modern people exceeding energy consumption, and the excess energy Part of it will be stored as fat in adipose tissue, leading to obesity, and obesity can cause a variety of metabolic abnormalities, which is one of the main risk factors for diabetes and cardiovascular diseases, and is associated with increased morbidity and mortality of cardiovas...

Claims

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Application Information

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IPC IPC(8): C07D307/79A61P3/04A61K31/496A61K49/00
Inventor 谭日红
Owner SHENYANG UNIV
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