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Method for preparing camptothecin derivatives and intermediates thereof

A technology for camptothecin and derivatives, which is applied in the field of organic chemical synthesis of pharmaceutical compound camptothecin derivatives, can solve problems such as harsh reaction conditions, low solubility, and difficult separation, and achieve increased reaction yield, reduced production cost, The effect of improving work efficiency

Inactive Publication Date: 2013-12-18
CHIA TAI TIANQING PHARMA GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In the above-mentioned preparation method, the reaction conditions are harsh, the reaction yield is very low (only about 20-30%), and it brings difficulties to the subsequent separation. Because the solubility of camptothecin in dichloromethane is low, it needs 6000 times of weight , in order to achieve the purpose of elution

Method used

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  • Method for preparing camptothecin derivatives and intermediates thereof
  • Method for preparing camptothecin derivatives and intermediates thereof
  • Method for preparing camptothecin derivatives and intermediates thereof

Examples

Experimental program
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Embodiment Construction

[0056] 1, the preparation of 7-hydroxyethyl camptothecin

[0057] In a 30 L reactor, 190.0 g (0.55 mol) of camptothecin, 570.0 g (2.05 mol) of ferrous sulfate heptahydrate and 6.18 L of deionized water were added. Stir to dissolve ferrous sulfate heptahydrate, add 3.33L concentrated sulfuric acid dropwise under cooling, and keep the temperature below 20°C. After dropping, add 1.90L (26.25mol) of 1,3-propanediol, cool to about 0°C, add dropwise 0.76L (7.44mol) of 30% hydrogen peroxide, and keep the temperature at 0-5°C. TLC inspection (developing solvent: methanol: chloroform = 1: 15, ultraviolet 365nm color development, Rf = 0.5) until the reaction of the raw materials was completed. Dilute to 190.0L with deionized water, absorb through HPD-400 macroporous adsorption resin column, and then wash with 24.0L deionized water until neutral. It was eluted with 50.0L of 95% ethanol and evaporated to dryness under reduced pressure to obtain 200.8g of crude product. The crude produc...

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Abstract

The invention discloses a method for preparing camptothecin derivatives and intermediates thereof and relates to the field of organic synthesis technologies, in particular to an organic chemical synthesis method of drug compound camptothecin derivatives. The invention provides a method for synthesizing the camptothecin derivatives and the intermediates thereof through a reaction of linear-chain diol and camptothecin, which solves problems of low yield and difficulty in separation in a traditional synthesis method. Compared with the traditional synthesis method, the synthesis method disclosed by the invention has a higher yield and is more convenient in subsequent processing.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an organic chemical synthesis method of a medicinal compound camptothecin derivative. Background technique [0002] Chinese invention patent application CN1580057A (application date on August 13, 2003) discloses a new class of camptothecin derivatives, and the general structural formula of this class of camptothecin derivatives is as follows: [0003] [0004] The patent also discloses several specific compounds, including: [0005] [0006] 7-Hydroxyethylcamptothecin succinate monoester 7-Hydroxyethylcamptothecin malonate monoester [0007] [0008] 7-Hydroxyethylcamptothecin glutarate monoester 7-Hydroxypropylcamptothecin succinate monoester [0009] This document also discloses the use of these camptothecin derivatives for anti-tumor and preparation of pharmaceutical preparations, wherein 7-hydroxyethyl camptothecin succinate monoester is also known as sin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/22
Inventor 张喜全张金生高勇刘飞
Owner CHIA TAI TIANQING PHARMA GRP CO LTD