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Crystalline ledipasvir compound and process for its preparation

A technology of solvate and acetonate, which is applied in the field of medicine and achieves the effects of less degraded impurities, stable crystal form and favorable storage.

Inactive Publication Date: 2017-10-27
NANJING CHIA TAI TIANQING PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Sofosbuvir is a nucleoside NS5B polymerase inhibitor prodrug developed by Gilead. It is the first anti-hepatitis C drug that can be used without interferon. It has been approved in combination with ribavirin for gene 2 , type 3 hepatitis C patients, but for patients with genotype 1 hepatitis C, sofosbuvir still needs to be used in combination with interferon

Method used

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  • Crystalline ledipasvir compound and process for its preparation
  • Crystalline ledipasvir compound and process for its preparation
  • Crystalline ledipasvir compound and process for its preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Preparation of Ledipavir Hemiacetone Solvate

[0029] Take 2.0 g of Radipavir diacetone hydrate, add 20 mL of n-heptane, and stir at 25-30°C for 5 hours. After filtration, the obtained solid was rinsed with n-heptane, and the solid was dried in a blast drying oven at 50° C. for 4 hours to obtain 1.6 g of light yellow solid.

[0030] The obtained light yellow solid proton nuclear magnetic resonance spectrum detection diagram is attached figure 1 , Attached figure 2 As shown, the peak of chemical shift 2.09 is a characteristic peak of acetone, which is 3.06H after integration, indicating that acetone and Ledipavir molecules form a complex with a molecular ratio of 1:2.

[0031] XRPD inspection chart is attached image 3 Shown.

[0032] Instruments and test conditions used for XRPD testing:

[0033] Instrument: Bruker d8 advance X-ray diffractometer

[0034] Test conditions: test current and voltage: 40kv / 40mA, detector: lyxEye, test step: 0.01°

[0035] Target type: Cu ...

Embodiment 2

[0036] Example 2: Preparation of Ledipavir Hemiacetone Solvate

[0037] Take 2.0 g of Radipavir diacetone hydrate, add 30 mL of n-hexane, and stir at 25-30°C for 4 hours. After filtration, the obtained solid was rinsed with n-hexane, and the solid was dried in a blast drying oven at 40° C. for 5 hours to obtain 1.5 g of a light yellow solid.

[0038] After testing, its proton nuclear magnetic resonance spectrum detection chart and XRPD detection chart are consistent with the product of Example 1.

Embodiment 3

[0039] Example 3: Preparation of Ledipavir Hemiacetone Solvate

[0040] Take 2.0 g of Radipavir diacetone hydrate, add 20 mL of petroleum ether, and stir at 25-30°C for 5 hours. After filtration, the obtained solid was rinsed with petroleum ether, and the solid was dried in a blast drying oven at 25° C. for 6 hours to obtain 1.6 g of light yellow solid.

[0041] After testing, its proton nuclear magnetic resonance spectrum detection chart and XRPD detection chart are consistent with the product of Example 1.

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PUM

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Abstract

The invention discloses a crystallized Ledipasvir compound, a preparation method therefor and a pharmaceutical composition comprising the crystallized Ledipasvir compound. The crystallized Ledipasvir compound provided by the invention has characteristics of being high in stability and beneficial for drying materials and transporting on production, and is suitable for being used as a bulk pharmaceutical chemical in industry. The invention further provides a preparation method for the crystallized Ledipasvir compound, and the preparation method is simple to operate and high in yield. A pharmaceutical composition comprising the crystallized Ledipasvir compound provided by the invention can be used for treating hepatitis c.

Description

Technical field [0001] The invention belongs to the technical field of medicine, and relates to Ledipavir semiacetone compound and its crystal form, a preparation method, a pharmaceutical composition containing it, and an application thereof. Background technique [0002] Hepatitis C (CHC) is a viral hepatitis caused by hepatitis C virus (HCV) infection. It is mainly spread through blood transfusion, acupuncture, drug use, etc. According to the World Health Organization, about 180 million people worldwide are infected with HCV. There are approximately 3 to 4 million new cases of hepatitis C each year. [0003] Sofosbuvir is a nucleoside NS5B polymerase inhibitor prodrug developed by Gilead. It is the first anti-hepatitis C drug that can be used without interferon. It has been approved in combination with ribavirin for gene 2 , 3 type hepatitis C patients, but for genotype 1 hepatitis C patients, sofosbuvir still needs to be used in combination with interferon. [0004] Sofosbuvir / L...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14A61K31/4184A61P31/14
CPCC07B2200/13C07D403/14
Inventor 张健柴雨柱徐丹朱春霞田舟山王润卿马仕珉
Owner NANJING CHIA TAI TIANQING PHARMA
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