Rheinic acid berberine ion pair compound, preparation method and applications

A technology of berberine hydrochloride and rhein, applied in carboxylate preparation, digestive system, organic chemistry, etc., can solve the problems of affecting systemic therapeutic effect, low oral bioavailability, poor preparation stability, etc., and achieves increase Bioavailability, beneficial for long-term storage and in vivo use, and the effect of improving drug efficacy

Inactive Publication Date: 2013-09-25
王从品 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Because rhein is insoluble in water and cannot be completely absorbed by the gastrointestinal tract, resulting in low bioavailability, these have limited the application of rhein, and the formation of salts between rhein and metal ions increases the water solubility of rhein. properties, improve the bioavailability of oral route, but rhein sodium salt, potassium salt (US6197818, CN97107137) are strong base and weak salt, the aqueous solution is alkaline, and the pH value of making water injection is higher, which will cause physiological damage to the human bod

Method used

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  • Rheinic acid berberine ion pair compound, preparation method and applications
  • Rheinic acid berberine ion pair compound, preparation method and applications
  • Rheinic acid berberine ion pair compound, preparation method and applications

Examples

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Example Embodiment

[0043] The preparation of embodiment 1 rhein berberine ion pair compound

[0044]

[0045] Dissolve 3.9 g (0.01 mol) of berberine hydrochloride in 500 ml of water, heat to above 80°C until berberine hydrochloride is completely dissolved, and make berberine hydrochloride aqueous solution (A); dissolve 3.06 g of rhein sodium salt ( 0.01mol) was dissolved in 200ml of water to make rhein sodium salt aqueous solution (B); slowly drop (B) into (A), stir continuously at 80°C, react for 1 hour (h), and cool to room temperature , the separated precipitate was suction filtered and washed with pure water, and the precipitate was dried in a vacuum oven at 60°C to obtain purple-red crystals.

Example Embodiment

[0046] The preparation of embodiment 2 rhein berberine ion pair compound

[0047] Dissolve 3.9 g (0.01 mol) of berberine hydrochloride in 500 ml of water, heat to above 90°C until berberine hydrochloride is completely dissolved, and make berberine hydrochloride aqueous solution (A); dissolve 6.12 g of rhein sodium salt ( 0.02mol) was dissolved in 300ml of water to prepare sodium rhein salt aqueous solution (B); slowly added (B) dropwise to (A) and stirred continuously at 80°C, reacted for 1h, cooled to room temperature, and precipitated The precipitate was suction-filtered and washed with pure water, and dried in a vacuum oven at 60°C to obtain purple-red crystals.

Example Embodiment

[0048] The preparation of embodiment 3 rhein berberine ion pair compound

[0049] Dissolve 3.9 g (0.01 mol) of berberine hydrochloride in 500 ml of water, heat to above 90°C until berberine hydrochloride is completely dissolved, and make berberine hydrochloride aqueous solution (A); dissolve 1.61 g of rhein potassium salt ( 0.005mol) was dissolved in 500ml ethanol to prepare rhein ethanol solution (B); slowly add (B) dropwise to (A) and keep stirring at 60°C, react for 1h, cool to room temperature, and dissolve the precipitated The precipitate was suction-filtered and washed with pure water, and dried in a vacuum oven at 60°C to obtain purple-red crystals.

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Abstract

The invention relates to a rheinic acid berberine ion pair compound with a formula (I) structure and a preparation method thereof, comprising the following steps of: (1) preparing a berberine hydrochloride solution, (2) adding rheinic acid or an alkali metal salt of rheinic acid into the solution obtained in the step (1), heating, stirring and fully reacting; and (3) filtering, washing, refining and drying the reaction products to obtain the rheinic acid berberine ion pair compound. The invention further relates to pharmaceutical compositions containing the ion pair compound, wherein the weight of the ion pair compound is 0.1-99.9% that of the compositions. The invention also relates to applications of the ion pair compound and the compositions thereof for preparing medicines for treating bacterial infection, peptic ulcer, diabetes, hyperlipemia, obesity, arthritis, heart failure, arrhythmia, platelet aggregation, hypertension, intestinal adhesion, etc. The rheinic acid berberine ion pair compound can increases lipid solubility of rheinic acid and berberine, and substantially raises a biological utilization degree.

Description

technical field [0001] The invention relates to a rhein berberine ion-pair compound and a preparation method, as well as the application of the drug in the preparation of drugs for treating antibacterial, peptic ulcer, diabetes and the like. Background technique [0002] Rhein is obtained from Rheum palmatum L., Rheum tanguticum Maxim.ex Balf. or Rheum officinale Baill.), Polygonum cuspidatum Sieb.et Zucc., Folium sennae, Polygonum multiflorum Thunb. ), Semen cassiae (Semen cassiae) and other plants, the compound of formula (II) is prepared by extraction, refinement or appropriate chemical modification. Rhein has pharmacological effects such as lowering blood sugar, lowering fat, improving insulin resistance and reducing urinary protein excretion, and can play multi-target and multi-level effects in diabetes and its complication diabetic nephropathy (CN 1899277A); rhein compounds It has been studied in the preparation of osteoarthritis, rheumatoid arthritis and rheumatoid a...

Claims

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Application Information

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IPC IPC(8): C07D455/03C07C66/02C07C51/41A61K31/4375A61K31/192A61P31/04A61P31/10A61P31/12A61P1/16A61P1/04A61P3/10A61P3/06A61P3/04A61P19/02A61P29/00A61P13/12A61P9/10A61P25/00A61P9/04A61P9/06A61P7/02A61P9/12A61P1/00
Inventor 王从品孙伟新方正陆重琳朱正宏毛李征张海燕朱明辉
Owner 王从品
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