Lacosamide synthesis technology

A synthesis process, lacosamide technology, applied in the field of lacosamide synthesis process, can solve the problems of harsh conditions, complicated operation, high cost, etc., achieve the effect of optimizing reaction, optimizing process conditions and reducing usage

Inactive Publication Date: 2013-09-25
WUHAN INSTITUTE OF TECHNOLOGY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The problem to be solved by the present invention is to provide a synthetic process for lacosamide aiming at the above-mentioned prior art, which overcomes the shortcomings of the existing routes such as low yield, high cost, harsh conditions, and complicated operation, and has potential industrial application prospects

Method used

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  • Lacosamide synthesis technology
  • Lacosamide synthesis technology
  • Lacosamide synthesis technology

Examples

Experimental program
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Embodiment 1

[0023] 1) At 0°C, add 44.8g (0.57mol) of acetyl chloride to 250ml of anhydrous methanol, then add 20g (0.19mol) of D-serine (2), and heat up to 70°C for 7 hours under reflux after the addition. After the reaction was completed, it was concentrated to dryness at 45°C to a solid, then added acetone and stirred overnight, filtered the next morning, and dried to obtain 26.6 g of D-3-hydroxy-2-alanine methyl ester (3) as a white solid, with a yield of 90%. Melting point 163-164°C;

[0024] 2) At room temperature, dissolve 10g (0.064mol) of methyl D-3-hydroxy-2-alanine (3) in 40ml of acetone solution, then add 14.3g (0.141mol) of triethylamine and (BOC) 2 O14g (0.064mol) was added dropwise to the system, and reacted at room temperature for 10h. After the reaction was completed, acetone was evaporated under reduced pressure, water was added, extracted with ethyl acetate 3*50ml, the ethyl acetate layers were combined, and saturated hydrogen carbonate Wash with sodium 2*50ml, saturate...

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Abstract

The invention relates to a lacosamide synthesis technology. Lacosamide as a required product is prepared by esterification, protection, amidation, methylation, deprotection and acetylation. The lacosamide synthesis technology has simple processes, is suitable for industrial production, utilizes a single reaction, allows mild conditions, can be controlled easily and has a good market prospect.

Description

technical field [0001] The invention relates to a synthesis process of lacosamide. Background technique [0002] Lacosamide is clinically mainly used for the adjuvant treatment of diabetic neuralgia and partial seizures in adult patients with epilepsy. Lacosamide is a novel NMDA receptor glycine site-binding antagonist, which belongs to a new class of functional amino acids and is an anticonvulsant drug with a new dual mechanism of action. It selectively promotes the slow inactivation of sodium channels and regulates the collapse response mediator protein CRMP-2, which may slow or even prevent seizures and reduce neuropathic pain in diabetes. [0003] The patent (WO2011144983A2) reports that there are currently four main methods for the preparation of lacosamide. Method 1: D-serine is protected, methylated with dimethyl sulfate, condensed with benzylamine under the action of a condensing agent, deprotected, and acetylated to prepare lacosamide. This method uses expensive ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/22C07C231/14
Inventor 王凯金琪宋率华马云峰郭嘉张秀兰张珩
Owner WUHAN INSTITUTE OF TECHNOLOGY
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