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Lacosamide synthesis method

A technology of lacosamide and synthesis method, which is applied in the field of medicine, can solve problems such as high cost, expensive raw materials, and cumbersome processes, and achieve the effects of reducing emissions, making the process route green and environmentally friendly, and simplifying the reaction steps

Active Publication Date: 2016-06-08
山东安信制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the process is more cumbersome, the price of raw materials is more expensive, and the cost is high

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0044] Embodiment 1 (the synthesis of R-2-isobutoxycarbonyl-N-benzyl-3-hydroxyl propionamide)

[0045]

[0046] Add 50g of D-serine into 200ml of dichloromethane, cool down to -15°C, add 96.2g of triethylamine dropwise, stir for 10min after dropping, add 130g of isobutyl chloroformate dropwise, stir for 10min after dropping, slowly add 51g of benzyl After the amine was added and reacted for 2 hours, the dichloromethane phase was washed with 200ml of water, 200ml of 1mol / L HCl solution, 200ml of 8% sodium bicarbonate solution, and 200ml of water in sequence, dried over anhydrous sodium sulfate, and filtered with suction, and the filtrate was directly used in the next reaction .

Embodiment 2

[0047]Example 2 (synthesis of R-2-isobutoxycarbonyl-N-benzyl-3-methoxypropionamide)

[0048]

[0049] Add dropwise 200ml of ether solution containing 20.5g of diazomethane to the above dichloromethane solution under ice bath, after the dripping is completed, rise to room temperature and react for 5h. for the next reaction.

Embodiment 3

[0050] Embodiment 3 (the synthesis of R-2-amino-N-benzyl-3-methoxy propionamide)

[0051]

[0052] Add 120ml of concentrated hydrochloric acid dropwise to the above dichloromethane phase, control the temperature at 20-30°C, and react for 2 hours after dropping. 300ml of water was extracted, and the aqueous phase was adjusted to pH 12 with 30% aqueous sodium hydroxide solution, and the aqueous phase was extracted with 300ml of dichloromethane, and the dichloromethane phase was dried with anhydrous sodium sulfate and filtered with suction, and the filtrate was directly used in the next reaction.

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Abstract

The invention discloses a lacosamide synthesis method. According to the method, D-serine, tertiary amine and alkyl chloroformate react with benzylamine to generate R-2-isobutoxy carbonyl-N-benzyl-3-hydroxy propanamide; then R-2-isobutoxy carbonyl-N-benzyl-3-hydroxy propionamide reacts with diazomethane to generate R-2-isobutoxy carbonyl-N-benzyl-3-methoxyl propanamide, and then reduction and acetylization are conducted, so that lacosamide is obtained. The purity of lacosamide prepared through the method reaches 99.95% and above, and the chiral purity reaches 99.90%.

Description

technical field [0001] The invention relates to a synthetic method of lacosamide, which belongs to the technical field of medicine. Background technique [0002] Lacosamide, Chinese chemical name: (R)-2-acetamido-N-benzyl-3-methoxypropionamide, molecular formula C 13 h 18 N 2 o 3 , the molecular weight is 250.29, and the structural formula is as follows: [0003] [0004] Lacosamide is a third-generation drug for the treatment of epilepsy and neuropathic pain developed by UCB Pharmaceutical Co., Ltd. in Belgium. Lacosamide is the first new antiepileptic drug for the treatment of partial seizures in the past three years, and it provides a new treatment method for patients with uncontrolled partial seizures. [0005] Lacosamide is a new type of N-methyl-D-aspartate (NMDA) receptor glycine site-binding antagonist, which belongs to a new type of functional amino acid anticonvulsant drug, and has dual effects of anticonvulsant and analgesia. The drug has been approved by...

Claims

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Application Information

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IPC IPC(8): C07C269/04C07C271/22C07C269/06C07C231/12C07C237/06C07C237/22C07C231/24
CPCC07C231/12C07C231/24C07C269/04C07C269/06C07C271/22C07C237/06C07C237/22
Inventor 周显峰李卓华左景冉吴兆申李文华李法东余志海董廷华张兆珍吴柯李保勇
Owner 山东安信制药有限公司
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