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Preparation method of Ledipasvir

A formula and compound technology, applied in the direction of organic chemistry, can solve the problems of low total yield, only 38% yield, high synthesis cost, etc., and achieve the effect of reducing the cost of raw materials and the use of organic solvents

Active Publication Date: 2016-01-13
厦门蔚嘉制药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] In addition, other patents such as WO2012076942 have also reported the use of compounds through CaCO 3 , obtained directly in one step, but requires chromatographic column separation, and the yield is 62%
The subsequent cyclization reaction also requires chromatographic column separation, and the yield is only 38%.
It can be seen that due to the complex structure of ledipasvir, the synthesis route is relatively single, and the total yield for industrial production is relatively low, which makes the synthesis cost high, which is not conducive to large-scale production and the promotion and use as a drug

Method used

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  • Preparation method of Ledipasvir
  • Preparation method of Ledipasvir
  • Preparation method of Ledipasvir

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Embodiment Construction

[0034] Below by embodiment the content of the present invention is specified:

[0035] 1) As shown in formula I, under nitrogen protection, add formula (i) compound (20g, 82.9mmol), potassium carbonate K 2 CO 3 (8g, 57.9mmol), acetone (200mL) were mixed, stirred and reacted at 35°C for 3h, then added the compound of formula (ii) (30g, 83.9mmol) and sodium iodide NaI (3g), reacted at 35°C for 3h, and TLC (developing solvent PE (petroleum ether): EA (ethyl acetate) = 5:1 mixture) detection shows that the compound of formula (ii) reacts completely, add 100g of water to cool down the reaction system to 10-15°C, stir for 1h, pump Filter, wash the filter cake with 100ml of acetone-water mixed solution with a volume ratio of 1:4, and dry to obtain the compound of formula (iii), which is 45g and the yield is 97%;

[0036]

[0037] 2) As shown in formula I, add formula (iii) compound (42g, 75mmol), ammonium acetate NH 4 OAc (29.4g, 38.1mmol), toluene (380mL) and 2-methoxyethanol ...

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Abstract

The invention discloses a preparation method of Ledipasvir. The method has no need for chromatographic column separation, reduces the cost of raw materials, and can acquire a high purity product by a simple precipitation or crystallization purification means, thus providing feasible technical conditions for large-scale industrial production.

Description

technical field [0001] The invention relates to a preparation method of ledipasvir. Background technique [0002] Hepatitis C is a viral hepatitis caused by hepatitis C virus (HCV) infection, which is mainly transmitted through blood transfusion, acupuncture and drug abuse. Hepatitis C can lead to chronic inflammation, necrosis and fibrosis of the liver, and some patients can develop liver cirrhosis or even hepatocellular carcinoma (HCC), which is extremely harmful to the health and life of patients and has become a serious social and public health problem. [0003] The current treatment regimen for hepatitis C is usually a combination of ribavirin, interferon and protease inhibitors. These drugs need to be used continuously for 48 weeks. The burden on patients is heavy and the cost is high. Some patients may have serious side effects such as anemia, depression, and loss of appetite. [0004] Ledipasvir (Ledipasvir) is a hepatitis C virus NS5A inhibitor, its chemical name ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14
CPCC07D403/14
Inventor 侯鹏翼李泽敏温兆辉
Owner 厦门蔚嘉制药有限公司
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