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Method for preparing epirubicin hydrochloride and intermediate compound

A technology for epirubicin hydrochloride and intermediates, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of long reaction route, high cost, and heavy metal pollution, and reduce the consumption of raw materials , reduce the cost of response, and improve the effect of core competitiveness

Inactive Publication Date: 2017-07-25
CHENGDU UNIV
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Problems solved by technology

[0007] In order to solve the technical problems of long reaction route, heavy metal pollution and high cost in the existing synthesis method of epirubicin hydrochloride, the present invention provides a simple and environmentally friendly method, which not only greatly reduces the discharge of three wastes, but also reduces energy consumption and consumption of raw materials have improved the core competitiveness of such drugs in my country. The method of the present invention is mainly obtained by selectively oxidizing and reducing doxorubicin, and its reaction route is as follows: figure 1 shown

Method used

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  • Method for preparing epirubicin hydrochloride and intermediate compound
  • Method for preparing epirubicin hydrochloride and intermediate compound
  • Method for preparing epirubicin hydrochloride and intermediate compound

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Embodiment 1

[0056] 1. Preparation of intermediate compounds

[0057] Under the protection of nitrogen, install a stirrer and a thermometer in a 500mL three-necked flask, add 300mL of dichloromethane and 54.3g (100mmol) of doxorubicin as a raw material, and cool to -20°C. At this temperature, add 16.8g (60mmol) of 2-iodobenzoic acid IBX and 39.0g (50mmol) of dimethyl sulfoxide DMSO in batches, continue stirring for 3 hours, rise to 0°C and continue stirring for 0.5 hours, and slowly rise to room temperature . Add 300 mL of dichloromethane to dilute, filter, and wash the organic phase with 0.1M dilute hydrochloric acid solution, saturated sodium bicarbonate solution, and saturated brine, respectively. Dry over anhydrous magnesium sulfate, and concentrate the organic phase to obtain an oily liquid. Add 300 mL of n-hexane to this liquid, crystallize under slow stirring at -5°C, and filter to obtain an orange powdery solid intermediate. It is determined that the yield of the intermediate re...

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Abstract

The invention discloses a novel method for synthesizing epirubicin hydrochloride (compound 1) from adriamycin. Epirubicin is directly obtained by selective oxidation and reduction. Compared with the existing method, the novel method has the advantages that the reaction route is more concise, the synthesis efficiency is improved, raw materials for reaction are easily obtained, conditions are mild, the energy consumption and the cost are reduced, and the total yield reaches 68 percent.

Description

technical field [0001] The invention relates to the field of medicine preparation, in particular to a preparation method of epirubicin hydrochloride and an intermediate compound thereof. Background technique [0002] Epirubicin hydrochloride (eprubicin hydrochloride, epirubicin hydrochloride), is an anthracycline antitumor antibiotic developed by Pfizer for the treatment of breast cancer, lung cancer, and liver cancer. It was launched in Europe in 1984 and in the United States in 1999. It has broad application in the treatment of leukemia, lymphoma and various solid tumors including breast cancer, non-small cell tumors, cervical cancer and head and neck cancer. Its mechanism of action is to intercalate directly between DNA nucleobase pairs, interfere with the transcription process, prevent the formation of mRNA, and thus inhibit the synthesis of DNA and RNA. In addition, epirubicin also inhibits topoisomerase II. As a cell cycle non-specific drug, it is effective for a var...

Claims

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Application Information

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IPC IPC(8): C07H15/252C07H1/00C07D309/30
CPCC07D309/30C07H1/00C07H15/252
Inventor 曹胜华董宏波罗红兵杜伟宏唐克慧王宇驰张春然侯明孟键
Owner CHENGDU UNIV
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