Method used for preparing Lopinavir using one-pot method

A technology of tetrahydropyrimidine and methylbutyric acid, applied in the field of medicine, can solve the problems of cumbersome operation and post-processing, increase the reaction steps of activated ester, and be unsuitable for industrial production, etc., and achieve easy separation and purification, short production cycle, synthesis and yield high rate effect

Inactive Publication Date: 2018-06-29
YANCHENG DESANO PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0012] Although the product quality and yield of method 3 are acceptable, the step of activated ester reaction is increased, and the operation and post-treatment are cumbersome. Considering the cost, it is not suitable for industrial production;

Method used

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  • Method used for preparing Lopinavir using one-pot method
  • Method used for preparing Lopinavir using one-pot method

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Embodiment 1

[0031] The present embodiment provides a method for preparing lopinavir by a one-pot method, specifically:

[0032] Add (2S)-(1-tetrahydropyrimidin-2-one)-3-methylbutanoic acid 20.0g (0.1mol) and dichloromethane 100ml into the reaction flask and place it under ice water, control the temperature below 10°C , 13.9 g (0.11 mol) of thionyl chloride was dropped into the reaction solution. After the dropwise addition was completed, the reaction was carried out at 0~10°C with stirring for 1 h, and then refluxed for 1 h to obtain (2S)-(1-tetrahydropyrimidine-2- Ketone)-3-methylbutyryl chloride reaction solution; the reaction solution was lowered to 0~20°C, 25.3g (0.25mol) of triethylamine was added, and placed under ice water, the temperature was controlled below 10°C, and N-[ (1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy)acetamide 42.4 g (0.095mol) was added to the reaction solution, after the addition was completed, the reaction was carried ou...

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Abstract

The invention discloses a method used for preparing lopinavir using one-pot method. According to the method, under certain organic solvent conditions, (2S)-(1-Tetrahydropyramid-2-one)-3-methylbutanoicacid is reacted with thionyl chloride so as to obtain (2S)-(1-Tetrahydropyramid-2-one)-3-methyl butyryl chloride; a weak base acid binding agent and N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy)acetamide are added into an obtained reaction system for amidation reaction; after amidation reaction, an obtained product is subjected to post-treatment so as toobtain lopinavir finished product. According to the method, on-pot method is adopted, the process is simple, production period is short, the finial products can be separated and purified easily, synthesis yield is high, the method is economical and is high in feasibility, and is suitable for industrialized production.

Description

technical field [0001] The invention relates to a method for preparing lopinavir by a one-pot method, which belongs to the technical field of medicine. Background technique [0002] Lopinavir, chemical name: (2S)-N-[(2R,4S,5S)-5-[[2-(2,6-Dimethylphenoxy)acetyl]amino]-4-hydroxy -1,6-diphenyl-hex-2-yl]-3-methyl-2-(2-oxo-1,3-diazacyclohex-1-yl)butanamide, its structure is as follows Shown: [0003] [0004] Lopinavir is an HIV-1 and HIV-2 protease inhibitor, which can be combined with low-dose ritonavir to improve its pharmacokinetic properties. Lopinavir combined with low-dose ritonavir compound tablet was approved by the United States in 2000 Approved by the Food and Drug Administration for marketing, it has reliable curative effect, few side effects, and is less affected by food. It is currently used as a first-line or second-line treatment drug against human immunodeficiency virus, and plays an important role in the antiviral treatment of HIV patients who have failed i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/10
CPCC07D239/10
Inventor 熊玉友汪守军张超吴德全
Owner YANCHENG DESANO PHARMA CO LTD
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