Single pot conversion of artemisinin into arteether

A kind of arteether and artemisinin technology, which is applied in the field of single-pot method of converting artemisinin into artemisinin

Inactive Publication Date: 2005-11-09
COUNCIL OF SCI & IND RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It should be noted that the aforementioned application does not use polyols as catalysts in the process of reducing artemisinin to dihydroartemisinin

Method used

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  • Single pot conversion of artemisinin into arteether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Artemisinin (1 g) and polyhydroxy catalyst dextrose (5 g) were stirred in ethanol (20 ml) for 5 minutes at room temperature. At this point sodium borohydride (600 mg) was added slowly over 10 minutes and the reaction mixture was stirred at room temperature (20 to 23°C) for about 1 hour. The reaction was monitored by TLC to check the completion of the reduction step. The acid catalyst trimethylchlorosilane (3.5ml) was slowly added at 10-23°C, and the reaction mixture was stirred at room temperature for about 1 hour. Cold water (about 150ml) was added to the reaction mixture and the aqueous reaction mixture was extracted with 1% ethyl acetate in hexane (3 x 50ml).

[0056] The combined ethyl acetate-hexane extracts were washed with 0.5% sodium bicarbonate solution (100 mL) and then with water (50 mL). The n-hexane extract was dried over anhydrous sodium sulfate and the solvent was evaporated to obtain 1.038 g of crude artether with some impurities. The impure artemethe...

Embodiment 2

[0058] Artemisinin (1 g) and polyhydroxy catalyst dextrose (4 g) were stirred in ethanol (15 ml). Sodium borohydride (500 mg) was added slowly over 10 minutes, and the reaction mixture was stirred at room temperature (20 to 23° C.) for 30 minutes. After the reduction step was complete, trimethylchlorosilane (3.5 ml) was added and the reaction mixture was stirred at room temperature for an additional 1.5 hours. After conventional work-up and purification by column chromatography (1:5 ratio), a mixture of alpha and beta arteether (0.805 g, 80.5% w / w) was obtained.

Embodiment 3

[0060] Artemisinin (1 g) and polyhydroxy catalyst dextrose (2 g) were stirred in ethanol (25 ml). Sodium borohydride (700 mg) was added slowly over 10 minutes, and the reaction mixture was stirred at room temperature (20 to 23° C.) for 1.5 hours. After the reduction step was complete, chlorotrimethylsilane (4 ml) was added and the reaction mixture was stirred at room temperature (20 to 23° C.) for an additional 2 hours to obtain 0.95 g of crude artether. After conventional work-up and purification by column chromatography, 0.95 g of crude artether yielded 0.825 g of a mixture of alpha and beta artether (82.5% w / w).

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Abstract

The present invention provides a method for the preparation of arteether from artemisinin in one pot in just about 4 hours comprising reduction of artemisinin into dihydroartemisinin by less quantity of sodium borohydride in ethanol at room temperature in the presence of a novel polyhydroxy catalyst, acylation of dihydroartemisinin in the presence of an acid catalyst, extraction of arteether from an aqueous reaction mixture using 1% ethyl acetate in n-hexane followed by workup and purification of the impure arteether to yield 80-86% (w / w) pure alpha, beta arteether.

Description

technical field [0001] The present invention relates to an improved single pot process for the preparation of arteether from artemisinin. Artether prepared by this method can be used to treat uncomplicated malaria, severe complicated malaria and multidrug-resistant malaria. Background technique [0002] Every year, among the 4 billion malaria patients in the world, about 1 to 3 million people (mainly children) die from malaria. The rapid spread of multidrug-resistant parasites to standard quinoline-based antimalarials such as chloroquine and mefloquine-based antimalarials has complicated chemotherapy in the treatment of malaria patients. [0003] Artemisinin and its derivatives artemether, artether, artelinate, and artesunate, a class of antimalarial compounds derived from Artemisia annua, have demonstrated promising activity and are being used in For the treatment of uncomplicated malaria, severely complicated malaria / cerebral malaria and multidrug resistant malaria. Dih...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/92C07D493/18C07D493/22
CPCC07D307/92
Inventor R・S・巴克乌尼A・特瓦里T・辛格S・P・S・哈努加
Owner COUNCIL OF SCI & IND RES
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