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Berberine additive product, medicament containing the same and preparation thereof

An adduct, berberine technology, applied in the field of prodrugs, can solve the problems of limiting the application of berberine, bactericidal effect affecting the balance of intestinal flora, etc., to improve bioavailability, simple synthesis method, and reduce pathology The effect of hyperglycemia

Inactive Publication Date: 2008-12-17
CENT HOSPITAL XUHUI DISTRICT SHANGHAI CITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The bactericidal effect of high doses of berberine on normal intestinal flora will seriously affect the balance of intestinal flora, which greatly limits the application of berberine in the treatment of systemic diseases

Method used

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  • Berberine additive product, medicament containing the same and preparation thereof
  • Berberine additive product, medicament containing the same and preparation thereof
  • Berberine additive product, medicament containing the same and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 40g of berberine hydrochloride, add 500ml of water, stir in a water bath at 60°C to make a suspension, take it out, let it cool to about 40°C, add about 60ml of 20% (g / ml) sodium hydroxide dropwise until the pH is 11-12 , put it in an ice bath to cool to room temperature, add 40ml of acetone dropwise under continuous stirring to obtain a yellow precipitate, filter it to dryness, wash with 5000ml of water to pH 6-7, and dry at 60°C. Recrystallized with acetone, the resulting product was used for solubility determination, structure analysis and purity determination.

[0021] 1. Solubility

[0022] The compound is yellow or yellow-brown powder, almost insoluble in water, slightly soluble in ethanol, slightly soluble in acetonitrile and acetone.

[0023] 2. Structural analysis

[0024] 2.1 Proton NMR spectrum is as follows (the solvent is deuterated dimethyl sulfoxide):

[0025] 1 H NMR, δ7.250 (1H, s, H-1), 6.850 (1H, d, J=8.1Hz, H-11), 6.755 (1H, s, H-4), 6.715 (1...

Embodiment 2

[0043] Take 30g of berberine hydrochloride, put it in a three-neck flask, install a stirrer in the middle mouth, install a reflux device in one mouth, add 200ml of water to the other side of the feeding mouth, start stirring, slowly add 30ml of acetone, and heat to 60°C in a water bath , so that the reflux. Prepare 36ml of 20% (g / ml) sodium hydroxide solution, add it dropwise slowly, and stir constantly. After the dropwise addition, stir for 2 hours. After the reaction is over, put it into cold water to cool it, and filter the crystals with a Buchner funnel. Wash with 4000ml of water and dry at 60°C to obtain acetone berberine adduct.

Embodiment 3

[0045]Take 30g of berberine hydrochloride, put it in a three-neck flask, install a stirrer in the middle mouth, install a reflux device in one mouth, add 200ml of water to the other side of the feeding mouth, start stirring, slowly add 38ml of methyl ethyl ketone, and heat in a water bath to 80°C , so that the reflux. Prepare 36ml of 20% (g / ml) sodium hydroxide solution, add it dropwise slowly, and stir constantly. After the dropwise addition, stir for 2 hours. After the reaction is over, put it into cold water to cool it, and filter the crystals with a Buchner funnel. Wash with 4000ml of water and dry at 60°C to obtain methyl ethyl ketone berberine adduct.

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PUM

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Abstract

The invention relates to an additive product of berberine with a general formula (I), the structure of which is that: in the general formula (I), R refers to alkyl of C3-C5 containing beta-carbonyl. A preparation method of the additive product comprises the following steps that: berberine hydrochloride is prepared into aqueous solution which then reacts with a carbonyl compound with alpha-reactive hydrogen atom such as acetone or methyl ethyl ketone or methyl propyl ketone under the condition of pH value of 11-12, and then the mixture is filtered, cleaned and dried so as to obtain the additive product of berberine. Additive products containing the berberine or the additive product of berberine together with pharmaceutically usable auxiliary materials are used for preparing oral medicines with higher bioavailability than berberine pro-medicines, especially for preparing the medicines for resisting arrhythmia and heart failure, lowering blood fat or treating diabetes, and etc., and the medicines can exert the function of the berberine to cure systemic diseases of animals and human beings. The positive effect of the additive product of berberine of the invention is that: the synthesis method is simple; the additive product of berberine as a pro-medicine increases the blood concentration of the berberine medicines in a human body, thus promoting the bioavailability of berberine.

Description

technical field [0001] The invention relates to a prodrug that greatly improves the oral bioavailability of berberine, in particular to an adduct of berberine, a drug containing the compound, and a preparation method thereof. Background technique [0002] Berberine, also known as berberine, is a traditional natural antibacterial active substance extracted from plants such as Coptis chinensis, and is mainly used clinically for the treatment of intestinal bacterial infections. Pharmacological studies in recent years have found that in addition to being used for antibacterial and anti-inflammation, berberine hydrochloride also has various pharmacological activities such as improving cardiovascular diseases, lowering blood sugar, and lowering blood lipids. However, because berberine is a strong polar quaternary ammonium base in structure, it is difficult to penetrate the lipophilic barrier of the intestinal tract, and the water solubility of its hydrochloride is very small, resu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/03A61K31/4375A61P9/06A61P9/04A61P3/06A61P3/10
Inventor 余琛周菊珍潘俊芳王逸平贾晶莹陆川刘罡一李水军周红刘昀张梦琪刘艳梅王伟张之川
Owner CENT HOSPITAL XUHUI DISTRICT SHANGHAI CITY