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Epirubicin hydrochloride intermediate compound III

A technology of epirubicin hydrochloride and compounds, which is applied in the direction of sugar derivatives, sugar derivatives, organic chemistry, etc., can solve the problems of being unsuitable for industrial production, high production cost, and high technology requirements, so as to be suitable for industrial production and improve Safety, high-purity effect

Pending Publication Date: 2021-03-30
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The yield is low, it is easy to produce large impurities, the operation is cumbersome, the production cost is high, the technology is high, and it is not suitable for industrial production. Therefore, it is of great significance to study and provide a new synthesis method of epirubicin

Method used

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  • Epirubicin hydrochloride intermediate compound III
  • Epirubicin hydrochloride intermediate compound III
  • Epirubicin hydrochloride intermediate compound III

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054]Dissolve compound I (9.3g, 0.015mol) in methanol (150mL), slowly add iodobenzene diacetate (5.80g, 0.018mol), control the temperature at 0°C, stir for 1h, detect the reaction by TLC, after the reaction is complete, add ethyl acetate / Purified water (V 乙酸乙酯 :V 纯化水 =4:1, 150mL), the organic phase was collected, dried over anhydrous sodium sulfate, filtered, concentrated, crystallized by adding n-hexane (200mL), filtered, and dried to obtain compound II with a yield of 92.5% and a purity of 99.95%.

Embodiment 2

[0056] Dissolve compound I (9.3g, 0.015mol) in methanol (150mL), slowly add iodobenzene diacetate (4.83g, 0.015mol), control the temperature at 0°C, stir for 1h, detect the reaction by TLC, after the reaction is complete, add ethyl acetate / Purified water (V 乙酸乙酯 :V 纯化水 =4:1, 150mL) extraction, the organic phase was collected, dried over anhydrous sodium sulfate, filtered, concentrated, crystallized by adding n-hexane (200mL), filtered, and dried to obtain compound II with a yield of 90.4% and a purity of 99.93%.

Embodiment 3

[0058] Dissolve compound I (9.3g, 0.015mol) in methanol (150mL), slowly add iodobenzene diacetate (6.28g, 0.020mol), control the temperature at 0°C, stir for 1h, detect the reaction by TLC, after the reaction is complete, add ethyl acetate / Purified water (V 乙酸乙酯 :V 纯化水 =4:1, 150mL), the organic phase was collected, dried over anhydrous sodium sulfate, filtered, concentrated, crystallized by adding n-hexane (200mL), filtered, and dried to obtain compound II with a yield of 89.9% and a purity of 99.90%.

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to an epirubicin hydrochloride intermediate compound III. The synthetic method of the epirubicin hydrochloride intermediate compound III comprises the following steps: adding a compound II into an organic solvent B, conducting stirring for dissolution, adding a reducing agent, controlling the temperature for reaction, conducting extracting with an extracting agent after the reaction is finished, drying an organic phase with anhydrous sodium sulfate, conducting filtering, conducting concentrating underreduced pressure, and conducting drying to obtain a compound III. The compound synthesis is simple and easy to control; when the compound is used for preparing epirubicin, the route operation is simple and convenient, and the operation safety is improved; the production cost is saved and the method is more suitable for industrial production; and the target product prepared by the method has high purity and yield, and can overcome the defects of complex operation, high production cost, high technical requirements and the like in the prior art.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to an intermediate compound III of epirubicin hydrochloride. Background technique [0002] Epirubicin hydrochloride (also known as epirubicin hydrochloride), chemical name: (8S,10S)-10-[(3-amino-2,3,6-trideoxy-α-L-arabinopyranosyl )oxy]-6,8,11-trihydroxy-8-(hydroxyacetyl)-l-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride , is one of the anthracycline anticancer drugs, the structural formula is as follows: [0003] [0004] Epirubicin hydrochloride is an isomer of doxorubicin hydrochloride. The difference from doxorubicin is that the 4'-OH group of the amino sugar part changes from cis to trans, but this slight change in the three-dimensional structure Lead to its heart, bone marrow toxicity was significantly reduced. The mechanism of action is embedded in DNA nucleobase pairs, preventing mRNA transcription, thereby inhibiting the formation of DNA and R...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/252C07H1/00
CPCC07H15/252C07H1/00
Inventor 张贵民朱学环朱安国
Owner LUNAN PHARMA GROUP CORPORATION