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Preparation method and medical application of berberine hydrochloride conjugate

A technology of berberine hydrochloride and acid compound, applied in the field of food and pharmacy, can solve the problems of low oral bioavailability, low fat solubility, poor absorption and the like

Inactive Publication Date: 2016-07-06
HEFEI HUAFANG PHARMA SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, due to the poor water solubility of niacin, the oral bioavailability is not high, which limits its full efficacy.
However, berberine hydrochloride has very little water solubility, even less fat solubility, and poor absorption in the gastrointestinal tract, resulting in low oral bioavailability, which affects its systemic therapeutic effect.
Although nicotinic acid drugs and berberine have many similar pharmacological activities, their clinical use is limited to a certain extent due to their low bioavailability. The method of utilizing the degree and exerting the synergistic effect of the two will have very important clinical significance

Method used

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  • Preparation method and medical application of berberine hydrochloride conjugate
  • Preparation method and medical application of berberine hydrochloride conjugate
  • Preparation method and medical application of berberine hydrochloride conjugate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of nicotinic acid berberine conjugate

[0021] Take 3.7g of berberine hydrochloride, put it into a 100ml three-necked flask, add 100ml of ethanol, adjust the pH to 7-8 with 0.5mol / l sodium hydroxide, raise the temperature to 60-70°C, stir to dissolve, then add 1.25g of nicotinic acid , keep stirring at this temperature for 1-2 hours, filter while hot, concentrate the filtrate to one-third of the original volume, cool and crystallize, filter and dry to obtain 3.9 g of nicotinic acid berberine conjugate with a yield of 85%.

Embodiment 2

[0023] Synthesis of nicotinic acid berberine conjugate

[0024] Take 3.7g of berberine hydrochloride, put it into a 100ml three-neck flask, add 150ml of ethanol, adjust the pH to 7-8 with 0.6mol / l sodium hydroxide, raise the temperature to 60-70°C, stir to dissolve, then add 1.3g of nicotinic acid , keep stirring at this temperature for 1-2 hours, filter while hot, concentrate the filtrate to one-third of the original volume, cool and crystallize, filter and dry to obtain 4.1 g of nicotinic acid berberine conjugate with a yield of 89.5%.

Embodiment 3

[0026] Synthesis of nicotinic acid berberine conjugate

[0027] Take 3.7g of berberine hydrochloride, put it into a 100ml three-necked flask, add 100ml of ethanol, adjust the pH to 7-8 with 3mol / l sodium hydroxide, raise the temperature to 60-70°C, stir to dissolve, then add 2.0g of nicotinic acid, Stir at this temperature for 1-2 hours, filter while hot, concentrate the filtrate to one-third of the original volume, cool and crystallize, filter, and dry to obtain 4.0 g of nicotinic acid berberine conjugate with a yield of 87.3%. ESI-MS (M + +H)m / zcalcdforC 20 h 16 NO 4 + 337.13found337.17; ESI-MS (M + +H)m / zcalcdforC 6 h 4 NO 2 - 122.02found122.05.

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Abstract

The invention discloses a preparation method and medical application of a berberine hydrochloride conjugate, and belongs to the field of biological medicine.A hydrochloride derivative and berberine are salified through chemical synthesis, so that the problem that hydrochloride derivative medicine is poor in water solubility and low in oral bioavailability, and consequently full play of the medicinal effect of the hydrochloride derivative medicine is restricted is solved.Besides, berberine hydrochloride is poor in water solubility and poorer in lipid solubility and can not be well absorbed by the gastrointestinal tract, consequently, the oral bioavailability of berberine hydrochloride is low, and the holistic treatment effect of berberine hydrochloride is affected.The hydrochloride derivative shows an excellent effect of regulating the blood glucose and blood lipid of type-2 diabetes rats in animal experiments and has the main effects of improving oral glucose tolerance, promoting insulin secretion, improving insulin resistance, reducing the amount of triglyceride and the like.

Description

technical field [0001] The invention relates to the technical field of food and pharmaceuticals, in particular to the application of niacin derivatives in the preparation of products for preventing or treating obesity and related diseases or symptoms. Background technique [0002] About 12 million people die of cardiovascular disease and cerebral apoplexy every year in the world, and atherosclerosis caused by hyperlipidemia is the main cause of coronary heart disease, hypertension and cerebrovascular disease. In 2002, the global annual sales of only atorvastatin (a blood lipid-lowering drug) was nearly 8 billion US dollars, becoming the world's best-selling drug that year. It can be seen that the research and development of blood lipid-lowering drugs has significant social benefits and market prospects. Nicotinic acid is converted into nicotinamide in the body, and then forms nicotinamide adenine dinucleotide (coenzyme I) and nicotinamide adenine dinucleotide phosphate (coe...

Claims

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Application Information

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IPC IPC(8): C07D455/03A61K31/4545A61P3/04A61P3/10A61P3/06
CPCC07D455/03
Inventor 何勇高永好吴宗好封保龙
Owner HEFEI HUAFANG PHARMA SCI & TECH
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