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Improved synthesis method of eslicarbazepine acetate

A technology of eslicarbazepine acetate and a synthesis method, applied in the field of medicinal chemistry, can solve the problems of high cost of reaction reagents, low conversion rate of raw materials, complicated post-processing, etc., and achieves reduction of production cost and environmental pollution, shortening of reaction steps, The effect of improving product purity

Active Publication Date: 2016-03-09
开封豫港制药有限公司 +2
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The purpose of the present invention is to overcome the disadvantages of high reaction reagent cost, high toxicity, long reaction route, low conversion rate of raw materials and complicated aftertreatment in the above-mentioned prior art, and provide an improved synthetic method for preparing eslicarbazepine acetate

Method used

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  • Improved synthesis method of eslicarbazepine acetate
  • Improved synthesis method of eslicarbazepine acetate
  • Improved synthesis method of eslicarbazepine acetate

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Add 200mL of toluene, 42g of intermediate 1 ((s)-10-hydroxyl-10,11dihydro-5H-dibenzo[b,f]azepine) and 33ml of triethylamine to a 500mL reaction flask, followed by Stir in an ice bath, then slowly add 17g of acetyl chloride dropwise, keep the temperature not exceeding 10°C, continue to keep warm for 30 minutes after the dropwise addition, TLC detection (developer: PE:EA=4:1) The reaction of raw materials is complete.

[0023] Add perfluorosulfonic acid resin to the system, continue to stir, and then dropwise add an aqueous solution of potassium cyanate (containing 18 g of potassium cyanate) into the system, raise the temperature to 70-80°C and react for 4 hours. A large amount of light yellow solid appeared in the system, filtered, and the filter cake was washed with water.

[0024] The solid obtained above was dissolved in 100 mL of ethyl acetate, the resin was removed by filtration, and then 400 mL of xylene was added dropwise to the obtained solution, during which mor...

Embodiment 2

[0027] The steps are the same as above, except that the acid-binding agent in step (1) is selected from sodium bicarbonate and pyridine. Finally, white powdery eslicarbazepine acetate was obtained with a yield of 91%. The product purity reaches 99.7% (HPLC).

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Abstract

The invention relates to an improved synthesis method of eslicarbazepine acetate, and belongs to the field of pharmaceutical chemistry. (s)-10-hydroxyl-10,11-dihydro-5H-dibenzo[b,f]azepine is taken as the raw material, then the raw material is acylated by acetyl chloride to obtain (s)-10-acetyl-10,11-dihydro-5H-dibenzo[b,f]azepine, the reaction system is not separated, potassium cyanate is directly added into the reaction system to carry out reactions in the presence of strong acid ion exchanged resin so as to obtain (s)-10-acetyl-10,11-dihydro-5H-dibenzo[b,f]azepine-5-methanamide (eslicarbazepine acetate), and finally the coarse product is purified to obtain pure eslicarbazepine acetate. The provided method has the advantages that the reagent is cheap and has little toxicity, the reactions are safe and reliable, the reaction solvent and resin can be recycled and reused, the operation of post treatment is simple and convenient, the synthesis method is environment-friendly, the yield and purity are high, and the method can be applied to massive industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing and purifying eslicarbazepine acetate, belonging to the field of medicinal chemistry. Background technique [0002] Eslicarbazepine acetate, chemical name (s)-10-acetyl-10,11 dihydro-5H-dibenzo[b,f]azepine-5-carboxamide, an anti-inflammatory drug developed by Bial company in Portugal Epilepsy drugs were launched in Europe for the first time in October 2009 and were approved by the FDA in November 2013. It can be used as an adjuvant treatment for partial seizures in adult epilepsy patients with or without secondary generalized seizures, and has good safety and low neuropsychiatric side effects, and has broad market prospects. [0003] Currently, several methods for the synthesis of eslicarbazepine acetate have been reported. Invention patents WO2007012793 (A1) (route 1) and CN101421245A (route 2) disclose a method for preparing eslicarbazepine acetate by asymmetric catalytic hydrogenation using oxcarb...

Claims

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Application Information

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IPC IPC(8): C07D223/22
CPCC07D223/22
Inventor 陈水库田玉华朱来峰张涛王欣杨占稳郭海波郝平平张方杰杨蕾贾斌路存真时永琪
Owner 开封豫港制药有限公司
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