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New crystal form of telaprevir and preparation method thereof

A telaprevir and crystal form technology, applied in the field of medicinal chemistry, can solve problems such as high cost investment

Inactive Publication Date: 2018-11-20
刘凤娟
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Commercial-scale spray drying is a costly investment, and especially when using the solvents or solvent mixtures disclosed in the above-mentioned patent applications

Method used

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  • New crystal form of telaprevir and preparation method thereof
  • New crystal form of telaprevir and preparation method thereof
  • New crystal form of telaprevir and preparation method thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0024] The present invention also provides a method for preparing the new crystal form of telapivir, the specific steps are:

[0025] The method for preparing the new crystal form of telaprevir is characterized in that it comprises the following steps:

[0026] Step (1) Take telaprevir, add a solvent, and heat to 70°C to dissolve;

[0027] Step (2) Bring the solution obtained in step (1) to 40-60°C, and add water dropwise;

[0028] Step (3) heat preservation and stirring until crystallization is complete, suction filtration, washing with water, and drying to obtain telaprevir.

[0029] Preferably, the solvent in step (1) is selected from methanol, ethanol, isopropanol, n-heptane, ethylene glycol dimethyl ether, a mixed solvent of water and methanol, a mixed solvent of water and ethanol, water and isopropyl A mixed solvent of alcohol, water and ethylene glycol dimethyl ether; the mass-volume ratio of the telaprevir to the solvent is 1g:10ml~1g:50ml; the step (2) the telaprevir and water...

specific Embodiment approach

[0033] The following examples are used to describe the technical solutions of the present invention in detail, which will help to have a better understanding of the advantages and effects of the technical solutions of the present invention. The examples do not limit the protection scope of the present invention. The protection scope of the present invention is determined by the claims. To decide.

Embodiment

[0035] The preparation method of crude telaprevir is as follows:

[0036] Step 1: Preparation of 2-((S)-2-((S)-2-amino-2-cyclohexylacetamido)-3,3-dimethylbutyryl)octahydrocyclopenta[c] Pyrrole-l-carboxylic acid (lS, 3aR, 6aS)-tert-butyl ester

[0037] A 3L three-neck round bottom flask equipped with a top stirrer, thermocouple, addition funnel, nitrogen outlet, and ice / water bath was charged with HOBt·H 2 O (51.74g, 1.05 molar equivalent), EDC·HCl (64.8g; 1.05 molar equivalent), then DMF (200ml) was charged, and stirring was started. The slurry was cooled to 0-5°C, and then a solution of 2-aminocyclohexanoacetic acid (98.45g; 1.05 molar equivalent) in DMF (172.4g; 182.9ml) was added and charged into the addition funnel. Add it to the batch for about 30 minutes, maintaining the temperature at 0-5°C. Once the addition is complete, the reaction mixture is stirred at 0-5°C for 2 hours. The 2-((S)-2-amino-3,3-dimethylbutyryl)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid (lS, 3aR, ...

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Abstract

The invention belongs to the technical field of medicines, discloses a new crystal form of telaprevir and a preparation method thereof. The new crystal form of telaprevir shows characteristic diffraction peaks on an X-ray powder diffraction pattern represented by 2theta + / - 0.2 degrees at 10.78, 11.62, 18.04, 20.90, 23.12, 27.72, 31.00, 31.90, 32.86, 33.44, 37.30, 46.78 and 47.10, which is completely different from the prior art. The invention also discloses a preparation method of the new crystal form of telaprevir. The preparation method is simple, easy to operate, high in yield and purity and mild in reaction condition, and is suitable for large-scale production.

Description

Technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a new crystal form of telaprevir and a preparation method thereof. Background technique [0002] Hepatitis C (Hepatitis C) is a liver disease caused by Hepatitis C Virus (HCV). The virus can cause acute or chronic hepatitis, the severity of which ranges from mild illness lasting a few weeks to severe lifelong illness. Acute hepatitis C virus infection usually has no symptoms, and only in very rare cases can it cause life-threatening diseases. About 15%-45% of infected people can clear the virus by themselves within 6 months of infection without any treatment. The remaining 55%-85% of infected people will develop chronic hepatitis C virus infection. Among these chronic hepatitis C virus infections, the risk of cirrhosis within 20 years is 15%-30%. An estimated 71 million people worldwide are infected with chronic hepatitis C. In the mid-1990s, a lot of efforts were made in the ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K1/30
CPCC07K7/06
Inventor 刘凤娟
Owner 刘凤娟
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