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Ampelopsin pro-dug and preparing method and application thereof

A technology for estropodin and prodrug, which is applied in the field of novel podosin prodrug compounds, can solve problems such as being unfavorable for injection administration, difficult for industrialized production, complicated preparation process, etc., so as to improve bioavailability and realize clinical application. , good water solubility

Inactive Publication Date: 2012-05-02
FUJIAN HEALTH COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Staphylococcus has been proven to have anti-tumor, anti-oxidation, hypolipidemic, anti-inflammatory, antibacterial and other effects, but due to its low solubility and the possibility of being metabolized by bacteria in the intestinal tract, the bioavailability of oral administration is low
In addition, due to its low solubility in water, it is not conducive to making injection forms
These are the obstacles that affect its clinical application. At present, there are no related products of prednisone monomer used in clinical practice.
Although there are reports in the literature (Ruan LP, Yu BY, et.al.Improving the solubility of ampelopsin by solid dispersions and inclusion complexes.Journal of Pharmaceutical and Biomedical Analysis.2005, 38 (3): 457-64) using solid dispersion technology, ring Preparation technologies such as dextrin inclusion technology are used to improve the solubility of staphylophyllin, but these methods have disadvantages such as complicated preparation process, high cost, and difficult industrial production.
However, the use of surfactants, ethanol, dimethyl sulfoxide and other reagents to increase solubility has the disadvantage of high toxicity or irritation

Method used

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  • Ampelopsin pro-dug and preparing method and application thereof
  • Ampelopsin pro-dug and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation of embodiment 1 compound (I)

[0023] (1) Preparation of staphylophyllin meglumine complex: Feed according to the molar ratio of staphylophyllin and meglumine 1.05:1. Weigh 1.95g of meglumine and add it into 100ml of absolute ethanol, heat to reflux at 60°C, and stir until completely dissolved; another weigh 3.36g of staphylophyllin and dissolve it in 10ml of absolute ethanol, and heat to maintain the same temperature; Slowly add the absolute ethanol solution to the steroid solution, stir while adding, keep at 60°C for 30min, evaporate part of the solvent under reduced pressure until the solution becomes cloudy, store at -15°C for 12h, and filter to obtain the crude product.

[0024] (2) Refining: add the crude product to 10 ml of absolute ethanol, stir and wash, filter, repeat three times, and dry under reduced pressure to obtain compound (I). The yield was 74.2%.

Embodiment 2

[0025] The preparation of embodiment 2 compound (I)

[0026] (1) Preparation of staphylophyllin meglumine complex: Feed according to the molar ratio of staphylophyllin and meglumine 1:1. Weigh 195mg of meglumine and add it to 20ml of absolute ethanol, heat to reflux at 50°C, and stir until completely dissolved; another weigh 320mg of staphylophyllin and dissolve it in 5ml of absolute ethanol, and heat to maintain the same temperature; The solution was slowly added to the staphylocoxine solution, stirred while adding, kept at 50°C for 20 minutes, evaporated part of the solvent under reduced pressure until the solution became cloudy, stored at -4°C for 12 hours, and filtered to obtain the crude product.

[0027] (2) Refining: the crude product was added to 5 ml of absolute ethanol, stirred and washed, filtered, repeated three times, and dried in a phosphorus pentoxide desiccator to obtain compound (I). The yield was 69.5%.

Embodiment 3

[0028] The preparation of embodiment 3 compound (I)

[0029] (1) Preparation of staphylophyllin meglumine complex: Feed according to the molar ratio of staphylophyllin and meglumine 1.03:1. Weigh 390mg of meglumine and add it to 40ml of absolute ethanol, heat to reflux at 40°C, and stir until completely dissolved; another weigh 660mg of staphylophyllin and dissolve it in 10ml of absolute ethanol, and heat to maintain the same temperature; The solution was slowly added to the staphylocoxine solution, stirred while adding, kept at 40°C for 20 minutes, evaporated part of the solvent under reduced pressure until the solution became cloudy, stored at -4°C for 12 hours, and filtered to obtain the crude product.

[0030] (2) Refining: the crude product was added into a small amount of ethyl acetate, stirred and washed, filtered, repeated three times, and freeze-dried to obtain compound (I). The yield was 71.5%.

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Abstract

The invention discloses an ampelopsin pro-drug and a preparing method and application thereof. The general formula (I) of the ampelopsin pro-drug is:, and compared with ampelopsin, the compound increases the water solubility obviously. In the preparing method, poisonous organic solvent is not used, all the solvents can be recycled, and other non-environmental-friendly reagents are not used. The ampelopsin pro-drug compound can be prepared into various dosage forms in pharmacy, including injection, tablets, capsules and granules, which is especially suitable for preparing powder-injection for injection.

Description

Technical field: [0001] The invention relates to the field of medicine, in particular to a novel predrug compound of predrug, a preparation method thereof and a preparation using the compound as an active ingredient. Background technique: [0002] Staphylococcus, also known as dihydromyricetin, was first isolated by Kotake and Kubota in 1940 from the leaves of Fujian tea, A. Meliaefolia, a plant of the genus Vitis vinifera, and named as staphylococcus. Staphylococcus has been proven to have anti-tumor, anti-oxidation, hypolipidemic, anti-inflammatory, antibacterial and other effects, but due to its low solubility and the possibility of being metabolized by bacteria in the intestinal tract, the bioavailability of oral administration is low. In addition, because of its low solubility in water, it is unfavorable to be made into an injection form. These are the obstacles that affect its clinical application, and there are no related products of staphylovinyl monomer used in cli...

Claims

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Application Information

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IPC IPC(8): C07D311/32C07C215/10A61K9/14A61K31/352A61P35/00A61P39/06A61P3/06A61P29/00A61P31/04
Inventor 黄仁杰
Owner FUJIAN HEALTH COLLEGE
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