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Preparation method of dexrazoxane

A technology of dextropropylimine and diaminopropane, which is applied in the field of preparation of dextropropylimine, can solve the problems that the product purity cannot be improved, the synthesis route of dextropropylimine is complicated, and the post-processing steps are cumbersome, etc. The effect of industrialized production, shortened production cycle, and increased environmental friendliness

Active Publication Date: 2013-03-06
NANJING HAIRUN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The present invention aims at the problems that the synthesis route of dextropropyl imine is complicated, the cost is high, the post-treatment steps are cumbersome, and the product purity and product yield cannot be improved, and a preparation method of dextropropyl imine is provided, which comprises the following steps:

Method used

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  • Preparation method of dexrazoxane
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Examples

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Embodiment 1

[0043] Embodiment 1: the preparation of (S)-1,2-diaminopropane-tetraacetic acid methyl ester

[0044] Add 100 grams (0.68 moles) of (S)-1,2-diaminopropane hydrochloride, 324.76 grams (2.99 moles) of methyl chloroacetate, 283.3 grams (2.05 moles) of potassium carbonate, and 5 liters of acetone into 10 liters of reaction In the bottle, the temperature was raised to reflux for 16 hours. After the reaction was completed, the inorganic salt was filtered off, and the filtrate was concentrated to dryness to obtain a light yellow oil, which was dissolved in 2 liters of ethyl acetate and washed once with 0.2 liters of saturated sodium chloride solution. Dry over sodium sulfate, filter, and concentrate to obtain 195 g of methyl tetraacetate (yield of crude product: 79.2%).

[0045]

Embodiment 2

[0046] Embodiment 2: the preparation of (S)-1,2-diaminopropane-tetraacetic acid methyl ester

[0047] Add 50.4 grams (0.68 moles) of (S)-1,2-diaminopropane, 324.76 grams (2.99 moles) of methyl chloroacetate, 442 grams (3.20 moles) of potassium carbonate, and 5 liters of acetone into a 10-liter reaction flask, Heat up and reflux for 16 hours, the reaction is over, filter out the inorganic salts, concentrate the filtrate to dryness to obtain a light yellow oil, dissolve it in 2 liters of ethyl acetate, wash once with 0.2 liters of saturated sodium chloride solution, and wash with 50 grams of anhydrous sodium sulfate Dried, filtered, concentrated and dried to obtain 189 g of methyl tetraacetate (yield of crude product 76.8%).

[0048]

Embodiment 3

[0049] Embodiment 3: the preparation of (S)-1,2-diaminopropane-tetraacetic acid methyl ester

[0050] Add 100 grams (0.68 moles) of (S)-1,2-diaminopropane hydrochloride, 324.76 grams (2.99 moles) of methyl chloroacetate, 567 grams (4.1 moles) of potassium carbonate, and 5 liters of acetone into 10 liters of reaction In the bottle, the temperature was raised to reflux for 16 hours. After the reaction was completed, the inorganic salts were filtered off, and the filtrate was concentrated to dryness to obtain a light yellow oil, which was dissolved in 2 liters of ethyl acetate and washed once with 0.2 liters of saturated sodium chloride solution. Dry over sodium sulfate, filter, and concentrate to obtain 220 g of methyl tetraacetate (yield of crude product: 89.4%).

[0051]

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Abstract

The invention relates to the field of medicament synthesis, in particular relates the synthetic field of anti-tumor medicaments, and more particularly relates to a preparation method of dexrazoxane. Aiming at the problems that the current synthetic route of dexrazoxane is complex, the cost is high, the post treatment steps are tedious and the product purity and product yield cannot be improved, the invention provides the preparation method of dexrazoxane. (S)-1,2-diaminopropane-tetraacetate can be obtained through only one step, thus not only is the production cycle shortened, but also the production cost is reduced. Besides, according to the technical scheme disclosed by the invention, reaction conditions such as high temperature, long cycle and high toxicity are avoided, so that the synthetic process is more environment-friendly, and is more suitable for being used in current pharmaceutical industry.

Description

technical field [0001] The present invention relates to the field of drug synthesis, in particular to the field of synthesis of antineoplastic drugs, more specifically to a preparation method of dextropropimine. [0002] Background technique [0003] Dexrazoxane is the dextroisomer of razoxane, and its structural formula is as formula I: [0004] [0005] Dextropropimine is a lipophilic cyclic derivative of the chelating agent ethylenediaminetetraacetic acid, which is clinically used as a chemoprotectant, mainly for the prevention of anthracycline-induced cardiotoxicity. Dextropropylimine was developed by Chiron Corporation of the United States, first launched in Italy in 1992, and approved by FDA in July 1995. [0006] At present, there are mainly two synthetic methods of dextropropylimine, one is to obtain dextropropylimine by cyclization of 1,2-propylenediaminetetraacetic acid, and the other is to obtain dextropropylimine by cyclization of 1,2-propylenediaminetetraac...

Claims

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Application Information

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IPC IPC(8): C07D241/08
Inventor 赵小伟陈祥峰杜有国杨展雄
Owner NANJING HAIRUN PHARM CO LTD
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