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Nicotinic acid derivative, its preparation method and its pharmaceutical composition

A technology of drugs and compounds, applied in the field of medicine, can solve the problems of large therapeutic dose, limited clinical application, induced ulcer disease and gout, etc.

Active Publication Date: 2016-08-03
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a lipid-lowering drug, niacin has been used clinically for nearly 50 years. A large number of randomized and controlled clinical trials have confirmed that niacin alone or in combination with other drugs can reduce cardiovascular disease mortality. The required therapeutic dose is relatively large (3-6g / d), and it is easy to produce side effects such as facial flushing, itching, ulcer disease and gout, which limits its clinical application

Method used

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  • Nicotinic acid derivative, its preparation method and its pharmaceutical composition
  • Nicotinic acid derivative, its preparation method and its pharmaceutical composition
  • Nicotinic acid derivative, its preparation method and its pharmaceutical composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041]

[0042] N-(2-(5-(1,2-dithiolan-3-yl)pentanamido)ethyl)nicotinamide

[0043] Dissolve lipoic acid (6.18g, 30mmol) and BOP (15.9g, 36mmol) in 48ml of dichloromethane, add ethylenediamine (120mmol, 8.01ml) dropwise in an ice bath environment, stir for 60 minutes, then at room temperature Reacted for 30 minutes, the system was extracted three times with 20ml of saturated brine each time, and once with water, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to obtain the product, which was dissolved in 60ml of dichloromethane, and 4.2ml of TEA and niacin (1.11g, 9mmol) were added. With BOP (4.38g, 9.9mmol), the reaction was stirred at room temperature, monitored by TLC until the reaction was complete, and then extracted three times with 60ml of saturated brine each time, once with water, dried over anhydrous magnesium sulfate, concentrated to obtain the crude product, silica gel column Chromatographic separation, eluent methanol: dichloromethane = 1...

Embodiment 2

[0045]

[0046] N-(3-(5-(1,2-dithiolan-3-yl)pentanamido)propyl)nicotinamide

[0047] Dissolve lipoic acid (1.03g, 5mmol) and BOP (2.65g, 6mmol) in 16ml of dichloromethane, drop them into 1,3-propanediamine (3.40ml, 40mmol) in an ice bath, and stir for 60 Minutes, then react at room temperature for 30 minutes. The system is extracted three times with 20ml saturated brine each time, and once with water, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to obtain the product, which is dissolved in 20ml dichloromethane, and 1.4ml TEA, niacin (0.37 g, 3mmol) and BOP (1.46g, 3.3mmol). The reaction was stirred at room temperature. The reaction was monitored by TLC until the reaction was complete. Then, it was extracted three times with 20ml of saturated brine and once with water, dried over anhydrous magnesium sulfate, and concentrated to obtain a crude The product was separated by silica gel column chromatography, eluent methanol: dichloromethane = (1:100-5:1...

Embodiment 3

[0049]

[0050] N-(6-(5-(1,2-dithiolan-3-yl)pentanamido)hexyl)nicotinamide

[0051] Lipoic acid (1.03g, 5mmol) and BOP (2.65g, 6mmol) were dissolved in 16ml of dichloromethane, and added dropwise to 1,6-hexanediamine (5.27ml, 40mmol) in an ice bath, and stirred for 60 Minutes, then react at room temperature for 30 minutes. The system is extracted three times with 20ml saturated brine each time, and once with water, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to obtain the product, which is dissolved in 20ml dichloromethane, and 1.4ml TEA, niacin (0.37 g, 3mmol) and BOP (1.46g, 3.3mmol). The reaction was stirred at room temperature. The reaction was monitored by TLC until the reaction was complete. Then, it was extracted three times with 20ml of saturated brine and once with water, dried over anhydrous magnesium sulfate, and concentrated to obtain a crude The product was separated by silica gel column chromatography, eluent methanol: dichloromethan...

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PUM

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Abstract

The invention relates to the synthesis of a series of nicotinic acid hybrids and derivatives. The structural formula is shown in formula (I). The present invention also provides the preparation of the above-mentioned pharmaceutical composition, and its application in drugs for lowering blood lipids, preventing and treating atherosclerosis, reducing the risk of cardiovascular and cerebrovascular events, and other neuroprotective drugs involved in oxidative stress.

Description

Invention field [0001] The invention relates to a series of nicotinic acid hybrids, preparation methods, pharmaceutical compositions containing them, and medical applications. It is mainly used in compounds and compositions for dyslipidemia, diabetes, atherosclerosis, metabolic syndrome and similar diseases, and belongs to the field of medicine. Background of the invention [0002] The scientific name of niacin is pyridine-3-carboxylic acid, also known as niotinic acid (niacid), niacin or nicotinic acid, VB for short 5 , V pp Or NA, which is stable in the air and does not absorb moisture; it is very toxic. Niacin is an important hypolipidemic drug. Its effect is to reduce the content of triglyceride (TG) and free fatty acid (FFA) in the blood, relax blood vessels, and reduce the fluidity of fat in the serum. Not only that, NA can block the degradation of adipose tissue and reduce FFA in the blood at high doses, thereby reducing the secretion of very low-density lipoprotein-chole...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/12A61K31/496A61K31/455A61P3/10A61P3/06A61P9/10A61P3/00A61P25/00
Inventor 皮荣标姜伊鸣巢晓娟刘培庆黄燕姚美村何细新
Owner SUN YAT SEN UNIV
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