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Synthesis process of ledipasvir intermediate

A synthesis process and intermediate technology, applied in the field of synthesis process of ledipasvir intermediates, can solve anemia, allergies and depression-like psychosis, high difficulty in separation of catalyst and reaction liquid, increased cost of industrial waste liquid treatment, etc. problems, to achieve the effect of convenient separation, high yield and increased specific surface area

Active Publication Date: 2021-05-28
日照巴洛特药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The goal of the treatment of chronic hepatitis C is to clear the virus, thereby limiting or preventing the occurrence of complications, and the standard of successful treatment is defined as 24 weeks after stopping the treatment, the RNA of the hepatitis C virus cannot be detected in the serum of the patient, and the current hepatitis C The standard therapy for hepatitis is a combination of pegylated interferon and ribavirin, but this method may cause side effects such as anemia, allergic reactions, and depression-like psychosis. Therefore, research on new anti-chronic hepatitis C virus drugs has always been a research hotspot field, ledipasvir is a drug for the preparation of hepatitis C virus
[0004] The existing synthesis process of ledipasvir intermediate has low yield and long time-consuming process. A catalyst needs to be used in the synthesis process. Most of the existing catalysts are used once. After the reaction, the catalyst and the reaction solution Separation is difficult, which increases the treatment cost of industrial waste liquid

Method used

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  • Synthesis process of ledipasvir intermediate
  • Synthesis process of ledipasvir intermediate
  • Synthesis process of ledipasvir intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] A synthetic technique for a ledipasvir intermediate, specifically comprising the steps of:

[0044] Step S1: add glycolaldehyde into deionized water, stir until glycolaldehyde is completely dissolved, and prepare glycolaldehyde solution, add α-phenylethylamine and dichloromethane into the reaction kettle, at a speed of 200r / min, At a temperature of 25°C, stir until α-phenylethylamine is completely dissolved, continue stirring and add glycolaldehyde solution and anhydrous sodium sulfate, and react for 5 hours to obtain Intermediate 1;

[0045]Step S2: Add the intermediate 1 and deionized water prepared in step S1 into the reaction kettle, stir until the intermediate 1 is completely dissolved, add copper powder, and react for 1.5 hours at a temperature of 80°C to prepare To obtain intermediate 2, add intermediate 2 and acidic potassium permanganate solution into the reaction kettle, and react for 3 hours at a temperature of 50°C to obtain intermediate 3;

[0046] Step S3...

Embodiment 2

[0054] A synthetic technique for a ledipasvir intermediate, specifically comprising the steps of:

[0055] Step S1: add glycolaldehyde into deionized water, stir until glycolaldehyde is completely dissolved, and prepare glycolaldehyde solution, add α-phenylethylamine and dichloromethane into the reaction kettle, at a speed of 220r / min, At a temperature of 26°C, stir until α-phenylethylamine is completely dissolved, continue stirring and add glycolaldehyde solution and anhydrous sodium sulfate, and react for 4.8 hours to obtain Intermediate 1;

[0056] Step S2: Add the intermediate 1 and deionized water prepared in step S1 into the reaction kettle, stir until the intermediate 1 is completely dissolved, add copper powder, and react for 1.3 hours at a temperature of 82°C. To obtain intermediate 2, add intermediate 2 and acidic potassium permanganate solution into the reaction kettle, and react at a temperature of 53°C for 2.8 hours to obtain intermediate 3;

[0057] Step S3: Met...

Embodiment 3

[0065] A synthetic technique for a ledipasvir intermediate, specifically comprising the steps of:

[0066] Step S1: add glycolaldehyde into deionized water, stir until glycolaldehyde is completely dissolved, and prepare glycolaldehyde solution, add α-phenylethylamine and dichloromethane into the reaction kettle, at a speed of 260r / min, At a temperature of 28°C, stir until α-phenylethylamine is completely dissolved, continue to stir, add glycolaldehyde solution and anhydrous sodium sulfate, and react for 4.5 hours to obtain Intermediate 1;

[0067] Step S2: Add the intermediate 1 and deionized water prepared in step S1 into the reaction kettle, stir until the intermediate 1 is completely dissolved, add copper powder, and react for 1.4 hours at a temperature of 88°C. To obtain intermediate 2, add intermediate 2 and acidic potassium permanganate solution into the reaction kettle, and react at a temperature of 57°C for 2.5 hours to obtain intermediate 3;

[0068] Step S3: Methano...

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Abstract

The invention discloses a synthesis process of a ledipasvir intermediate, wherein the intermediate is prepared by taking alpha-phenylethylamine and o-nitroaniline as raw materials, the two raw materials are low in price and easy to store, the alpha-phenylethylamine is further made into an intermediate 4, enamine is effectively prevented from reverse reaction under an acidic condition, and then the yield of the ledipasvir intermediate is affected; in addition, a catalyst is prepared in the process of preparing the ledipasvir intermediate, the catalyst takes a carbon nanotube as a carrier, the surface of the carbon nanotube contains a large number of active groups under the action of mixed acid, and the modified carbon nanotube is prepared; the modified carbon nanotube is soaked in an ethanol solution of palladium chloride and ruthenium chloride, so that the surface of the modified carbon nanotube contains a large amount of palladium and ruthenium; and compared with a traditional catalyst, the catalyst can be repeatedly used and is more convenient to separate from a reaction solution, the treatment difficulty of industrial wastewater is greatly reduced, and environmental pollution is prevented.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical preparations, and in particular relates to a synthesis process of a ledipasvir intermediate. Background technique [0002] Hepatitis C virus, referred to as hepatitis C, is a viral hepatitis caused by hepatitis C virus. According to the World Health Organization, the global hepatitis C infection rate is about 3%, and it is estimated that about 170 million people carry it. Hepatitis C virus, hepatitis C can lead to chronic inflammation, necrosis and fibrosis of the liver, and some patients may develop cirrhosis or even liver cancer, which poses a great threat to the health and life of patients. [0003] The goal of the treatment of chronic hepatitis C is to clear the virus, thereby limiting or preventing the occurrence of complications, and the standard of successful treatment is defined as 24 weeks after stopping the treatment, the RNA of the hepatitis C virus cannot be detected in the seru...

Claims

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Application Information

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IPC IPC(8): C07C249/02C07C251/08C07D209/52C07D403/04B01J21/18B01J35/10B01J27/13
CPCC07C249/02C07D209/52C07D403/04B01J21/185B01J27/13C07B2200/07B01J35/61C07C251/08Y02P20/584
Inventor 刘加林霍萧勇方朝杰张渊源
Owner 日照巴洛特药业有限公司
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