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Inclusion compound of quinidine and amine cyclodextrin

A technology of cyclodextrin and inclusion complex, which is applied in the directions of active ingredients of heterocyclic compounds, pharmaceutical combinations, and medical preparations of non-active ingredients, etc. The requirements of drug application, etc., to achieve the effects of easy operation, mild conditions, and simple preparation methods

Inactive Publication Date: 2018-07-03
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Among the three commonly used cyclodextrins mentioned above, β-cyclodextrin is the most widely used due to its cheap and easy to obtain, moderate size and non-toxic properties, but the water solubility and inclusion of β-cyclodextrin The ability is limited, and it is often difficult to meet the requirements of pharmaceutical applications as an inclusion host molecule; therefore, how to properly modify the structure of β-cyclodextrin is the focus of research and development by those skilled in the art

Method used

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  • Inclusion compound of quinidine and amine cyclodextrin
  • Inclusion compound of quinidine and amine cyclodextrin
  • Inclusion compound of quinidine and amine cyclodextrin

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Preparation of Inclusion Complex of Quinidine and Mono-(6-amino-6-deoxy)-β-cyclodextrin

[0037] (1) Preparation of mono-6-OTs-β-CD

[0038] Take 210 g of β-cyclodextrin recrystallized with water, add it in batches to a three-necked flask (3 L) filled with 1300 mL of water, and stir at room temperature; weigh 17.2 g of sodium hydroxide and dissolve it in 50 mL of water, then slowly Add it dropwise to the suspension of β-cyclodextrin until the reaction solution gradually becomes clear, and continue stirring for 1.5 h; after the cyclodextrin in the reaction solution is completely dissolved and becomes clear, dissolve 26.0 g of p-toluenesulfonyl chloride in 80 mL Sonicate the acetonitrile until it becomes clear, and slowly add the solution dropwise to the reaction solution (dropping is completed in about 30 minutes), continue to stir for 2 hours, filter off the insoluble matter, and adjust the filtrate to pH = 7.5 with 2 mol / L hydrochloric acid. At this time, there is a la...

Embodiment 2

[0047] Preparation of Inclusion Complex of Quinidine and Mono-(6-Ethylenediamine-6-deoxy)-β-cyclodextrin

[0048] (1) The preparation method of mono-6-OTs-β-CD is the same as step (1) in Example 1.

[0049] (2) Preparation of mono-(6-ethylenediamine-6-deoxy)-β-cyclodextrin

[0050] Dissolve 3.0 g (2.3 mmol) of 6-OTs-βCD in 20 mL of molecular sieve-dried ethylenediamine, stir at room temperature until completely dissolved, react for 10 h under nitrogen protection at 80 °C, and evaporate under reduced pressure after the reaction is complete. Solvent, add a small amount of water to the reaction flask to dissolve the solid, continue to evaporate the solvent, then add 2 mL of water to dissolve the product, and slowly drop it into 400 mL of acetone, stir at room temperature for 30 min, collect the white precipitate by suction filtration, and The resulting crude solid was dried in a vacuum oven for 24 h. The dried solid powder was redissolved in 2 mL of distilled water, filtered to...

Embodiment 3

[0054] Preparation of Inclusion Complex of Quinidine and Mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin

[0055] (1) The preparation method of mono-6-OTs-β-CD is the same as step (1) in Example 1.

[0056] (2) Preparation of mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin

[0057] Dissolve 3.0 g (2.3 mmol) of mono-6-OTs-β-CD in 20 mL of dry diethylenetriamine, stir at room temperature until completely dissolved, and react at 80°C for 10 h under nitrogen protection. After the reaction is completed, Slowly drop the reaction solution into 400 mL of acetone, stir at room temperature for 30 min, remove the filtrate by suction filtration, collect the white precipitate, dissolve the precipitate in a small amount of water, drop it into 300 mL of acetone again, stir for 0.5 h, and then suction filter The white precipitate was collected and dried in a vacuum oven. The obtained solid powder was ground and added to 200 mL of ethanol, and the white precipitate was collected by ultr...

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Abstract

The invention discloses an inclusion compound of quinidine and amine cyclodextrin, belonging to the technical field of pharmacy. According to the invention, the amine cyclodextrin in the inclusion compound is amino-substituted beta-cyclodextrin; the inclusion compound of the amine cyclodextrin and the quinidine is prepared through a solvent method or an ultrasonic method; the amine cyclodextrin and the quinidine are adopted to form the inclusion compound; except for the inclusion effect of the cavity of the cyclodextrin with the quinidine, the cyclodextrin can form an alkali environment in anaqueous solution and forms an ion interaction with hydroxy of the quinidine; meanwhile, amino can form a cation in water and generates a hydrogen-bond interaction with a nitrogen atom on a quinidine molecule, thereby facilitating reinforcing water-solubility and stability of the inclusion compound. The inclusion compound provided by the invention has high stability and good water-solubility, and is expected to improve the bioutilizability of the quinidine. Meanwhile, the preparation method for the inclusion compound provided by the invention is simple and convenient, has mild conditions, facilitates operation and is applicable to industrial application.

Description

technical field [0001] The invention relates to an inclusion compound of quinidine and amine cyclodextrin, belonging to the technical field of pharmacy. Background technique [0002] Malaria is one of the most contagious and life-threatening diseases, infecting more than 300 million people worldwide and killing an average of more than 1 million people every year. Although malaria has been largely eliminated in most parts of the world, the total number of malaria infections continues to increase year by year. Cinchona alkaloid quinidine (English name Quinidine, structure as shown in formula II) is one of the first drugs used in malaria patients. This drug was found to have almost no side effects. At the same time, quinidine also has some other important biological activities, such as anti-heat, anti-arrhythmia and so on. However, due to the poor water solubility of quinidine, it leads to poor and irregular absorption of oral administration, which greatly limits its applicat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16A61K47/69A61K31/49A61P33/06A61P29/00A61P9/06
CPCA61K31/49C08B37/0015
Inventor 廖霞俐周诚宋爽杨波
Owner KUNMING UNIV OF SCI & TECH
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