Benzofuryl-containing acetylpiperazine compound and application thereof to medicine

A technology of benzofuryl and acetylpiperazine, which is applied in the field of compounds and its application in medicine, can solve problems such as difficult to control intestinal symptoms, and achieve the effect of simple synthesis method and inhibition of pancreatic lipase activity

Active Publication Date: 2018-05-04
丹东龙泽化工有限责任公司
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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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  • Benzofuryl-containing acetylpiperazine compound and application thereof to medicine
  • Benzofuryl-containing acetylpiperazine compound and application thereof to medicine
  • Benzofuryl-containing acetylpiperazine compound and application thereof to medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Preparation of 1-[2-(benzofuran-7-oxyl)acetyl]-4-phenylpiperazine (compound number T01)

[0043] Add 4.0 g (0.03mol) of 7-hydroxybenzofuran, 9.4 g (0.03mol) of 4-phenyl-4-chloroacetylpiperazine, 0.8 g (0.005mol) of potassium iodide, and 13.8g (0.10mol) of potassium carbonate In the reaction flask, an appropriate amount of acetone was used as a solvent, and heated to reflux for 3.5 h. Suction filtration, rotary evaporation to remove acetone, add an appropriate amount of petroleum ether to dissolve, extract once with 5% NaOH aqueous solution, collect the organic layer and dry it with anhydrous magnesium sulfate. Filter, rotary evaporate to remove petroleum ether, and freeze to precipitate a white solid. Recrystallized from ethanol to obtain 5.2 g of white solid, yield 51.6%, mp: 123-124°C. ESI-MS m / z: 337.2; 1 H-NMR (CDCl 3 ) δ(ppm): 3.28-3.34(4H, m), 3.56-3.62 (4H, m), 4.86 (2H, s), 6.72(1H, d, J =8.4 Hz), 6.79-6.84(1H, m), 6.95(2H, d, J =6.6 Hz) , 7.06(...

Embodiment 2

[0044] Example 2: Preparation of 1-[2-(benzofuran-7-oxyl)acetyl]-4-(4-methylphenyl)piperazine (Compound No. T02)

[0045] According to the preparation method of Example 1, a white solid was obtained with a yield of 62.8%, mp: 134-136°C. ESI-MS m / z: 351.4; 1 H-NMR (CDCl 3 ) δ(ppm): 2.40 (3H, s), 3.27-3.35 (4H, m), 3.54-3.62 (4H, m), 4.85 (2H, s), 6.74(1H, d, J =8.4 Hz), 6.82 (2H, d, J = 6.6 Hz), 6.96(1H, d, J =7.2 Hz), 7.08 (2H, d, J = 6.6 Hz), 7.18(1H, d, J =7.2 Hz), 7.28-7.33(1H, m),7.68(1H, d, J =8.4 Hz); IR(KBr) υ / cm -1 : 3018, 2934, 1638, 1569, 1514, 1472, 1445, 1282, 1199, 1167, 1130, 1119, 1060, 834, 720, 652.

Embodiment 3

[0046] Example 3: Preparation of 1-[2-(benzofuran-7-oxyl)acetyl]-4-(2-methylphenyl)piperazine (Compound No. T03)

[0047] According to the preparation method of Example 1, a white solid was obtained with a yield of 45.6%, mp: 122-123°C. ESI-MS m / z: 351.4; 1 H-NMR (CDCl 3 ) δ(ppm): 2.36 (3H, s), 3.25-3.31 (4H, m), 3.58-3.64 (4H, m), 4.85 (2H, s), 6.56-6.62 (2H, m), 6.74(1H , m), 6.96(1H, d, J =7.2 Hz), 7.02(1H, d, J = 6.6 Hz), 7.08-7.12 (1H, d, J = 6.6 Hz), 7.18(1H, d, J =7.2 Hz),7.28-7.33(1H, m), 7.68(1H, d, J =8.4 Hz); IR(KBr) υ / cm -1: 3016, 2929, 1640, 1572, 1524, 1488, 1449, 1276, 1199, 1168, 1130, 1118, 1055, 834, 730, 649.

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Abstract

The invention discloses a benzofuryl-containing acetylpiperazine compound and application thereof to a medicine, and relates to a compound and application thereof to the medicine. The benzofuryl-containing acetylpiperazine compound as well as an analogue and pharmacologically applicable salt thereof or a stereisomer and a prodrug thereof are used as lipase inhibitors. The structural general formula is as shown in the right: as shown in the specification. In the structural formula, Ar can be independently selected from a phenyl group, a C1 to C4 alkyl-substituted phenyl group, a C1 to C4 alkoxy-substituted phenyl group, and a halogen-substituted phenyl group. The new compound disclosed by the invention can be used as a lipase inhibitor capable of inhibiting the activity of lipase, so that fat cannot be converted and absorbed, and is discharged along with excrement; the benzofuryl-containing acetylpiperazine compound is used as a novel nutrition absorption reducer, can work on the gastrointestinal tract, prevent catalytic decomposition of the lipase and inhibit absorption of part of fat ingested by diets, and is applicable to obesity, including healthy obese people and obese people suffering from non-insulin-dependent diabetes.

Description

technical field [0001] The invention relates to a compound and its application in medicine, in particular to a benzofuryl-containing acetylpiperazine compound and its application in medicine. 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 cardiov...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/86A61K31/496A61P3/04
CPCC07D307/86
Inventor 谭日红安旭焕
Owner 丹东龙泽化工有限责任公司
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