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Method for separating and purifying 9-nitro camptothecin

A technology for separation and purification of nitrocamptothecin, which is applied in the field of high-purity 9-nitrocamptothecin, and can solve problems such as harsh operating environment, cumbersome process, and difficulty in scaling up

Inactive Publication Date: 2007-04-25
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The purification process of the crude product in this process consumes a large amount of solvent due to the extraction, the process is cumbersome and not easy to scale up, the solvents dichloromethane and chloroform used in the process are all solvents restricted by the National Pharmacopoeia, and the operating environment is relatively harsh

Method used

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  • Method for separating and purifying 9-nitro camptothecin
  • Method for separating and purifying 9-nitro camptothecin
  • Method for separating and purifying 9-nitro camptothecin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 1500ml of concentrated sulfuric acid to a 2000ml flask, and place it in an ice-salt bath to cool to an internal temperature of -5°C. 5 grams (0.0143 mole) of camptothecin powder were added in batches under stirring, and the reaction liquid was orange-red. After the dissolution is complete, slowly add 4.5ml of concentrated nitric acid (65% to 68%) dropwise under stirring, and the reaction solution turns black after adding half an hour. After the addition was completed, the mixture was stirred at -5°C for one hour, then slowly warmed to room temperature, and the reaction was stopped after stirring for 72 hours. The reaction solution was poured into 2000 g of ice water to obtain a mixed acid solution of camptothecin nitration product for later use.

[0023] About 300 grams of the processed macroporous adsorption resin HZ-802 (treated according to the conventional treatment method of ion exchange resin and adsorption resin) is packed into a glass column with a diameter...

Embodiment 2

[0026] The mixed acid solution of the camptothecin nitration product was obtained in the same manner as in Example 1, the macroporous adsorption resin was HZ-816, and the eluent was acetone. Silica gel chromatography separation silica gel adopts 200-400 mesh chromatographic silica gel, and the eluent ratio is changed to: a) 500ml of n-hexane; b) 1000ml of n-hexane: ethyl acetate as a mixture of 4:3; c) 500ml of n-hexane Alkane: ethyl acetate is a mixed solution of 2: 3; d) 500ml of ethyl acetate rinses, others are operated by the same equipment and process steps as in Example 1, and part b of the rinse solution can obtain a yellow powder through vacuum distillation 1.2 g, its melting point is 275.5-277 ° C, and its purity by high pressure liquid chromatography is 99.7%.

Embodiment 3

[0028] The mixed acid solution of the camptothecin nitration product was obtained in the same manner as in Example 1, the macroporous adsorption resin was HZ-841, and the eluent was methanol. The eluent ratio of the silica gel chromatography separation is changed to: a) 500ml of n-hexane; b) 1000ml of n-hexane: ethyl acetate is a 6:5 mixture; c) 500ml of n-hexane: ethyl acetate is 2:3 d) the ethyl acetate rinse of 500ml, others are operated by the same equipment and process steps as in Example 1, and the b part of the rinse solution can obtain 1.3 grams of yellow powder through vacuum distillation, and its melting point is 275.5-277 °C, and the purity was 99.6% as tested by high pressure liquid chromatography.

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Abstract

A process for separating and purifying 9-nitro camptothecine includes such steps as nitrifying the camptothecine by concentrated sulfuric acid or nitric acid, adsorbing the acid liquid containing coarse product by macroreticular resin, desorbing to obtain coarse product, chromatography by silicon gel column, eluting by n-hexane, ethyl acetate, or their mixture, rotation evaporating to recover solvent, and vacuum drying. Its purity is 99.5-99.9%.

Description

technical field [0001] The invention relates to a biochemical separation technology, in particular to a method for separating and purifying crude 9-nitrocamptothecin by adsorption chromatography and preparing high-purity 9-nitrocamptothecin. Background technique [0002] Camptothecin is an alkaloid present in the roots, bark, stems and seeds of the deciduous tree Camptotheca acuminata in the Davidiaceae family. In 1966, Wall et al. extracted and isolated the alkaloid from the stem of Campylodon sativa, and tested it against mouse leukemia and Wacker cancer in vitro, showing strong anticancer activity, which aroused great concern from people. Countries such as the United States, Japan, Canada and the United Kingdom have actively invested in the development of camptothecin and its analogues, and have synthesized hundreds of derivatives for biochemical screening. Many drugs have been or are about to undergo clinical research. Camptothecin has become...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/22C07D221/00C07D311/00C07D209/00
Inventor 徐环昕宁方红陈骏赵延斌庄思永刘坐镇
Owner EAST CHINA UNIV OF SCI & TECH
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