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Sofosbuvir monocrystal M and preparation method and applications of sofosbuvir monocrystal M

A sofosbuvir single crystal technology, which is applied in the field of sofosbuvir single crystal M and its preparation and application, can solve the problems of curative effect, change of drug bioavailability, drug absorption, transport influence and other problems, and achieve good application foreground effect

Inactive Publication Date: 2015-01-14
汤律进 +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, since the crystal form of the drug has a major impact on the absorption and transport of the drug, it will change the bioavailability of the drug and have a greater impact on the efficacy

Method used

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  • Sofosbuvir monocrystal M and preparation method and applications of sofosbuvir monocrystal M
  • Sofosbuvir monocrystal M and preparation method and applications of sofosbuvir monocrystal M
  • Sofosbuvir monocrystal M and preparation method and applications of sofosbuvir monocrystal M

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: Preparation of sofosbuvir single crystal

[0040] Dissolve 1g of Sofosbuvir in 20mL of 50°C chloroform-isopropanol (volume ratio 50:1) mixed solution, stir to dissolve, then cool the solution in which Sofosbuvir is dissolved to room temperature while stirring and crystallizing, Filter until no solid precipitates out, wash with a small amount of cold solvent (hexane or dichloromethane) (4°C), and send the sample for single crystal X-ray diffraction to determine the crystal structure. The obtained sofosbuvir is detected by HPLC, and the content is 99.9%; by gas chromatography, the residual solvent content is lower than 40ppm.

[0041] Its single crystal X-ray diffraction pattern has the following characteristics, the crystal belongs to the monoclinic system, the space group is P21, and the unit cell parameters: β = 108.96(3)°. unit cell volume The number of molecules in the unit cell is Z=2.

[0042] The drug used in the present invention is Sofosbuvir...

Embodiment 2

[0044] Embodiment 2: Preparation of Sofosbuvir single crystal

[0045] Dissolve 1g of Sofosbuvir in 6mL of dimethyl carbonate at 50°C, slowly crystallize under stirring, collect the crystals by filtration, wash with a small amount of cold solvent (hexane or dichloromethane), select the crystals and send them to the sample for determination Crystal X-ray diffraction to determine the three-dimensional structure of the obtained new crystal form of Sofosbuvir.

[0046] Its single crystal X-ray diffraction pattern has the following characteristics, the crystal belongs to the monoclinic system, the space group is P21, and the unit cell parameters: β = 108.96(3)°. unit cell volume The number of molecules in the unit cell is Z=2.

[0047] The drug used in the present invention is Sofosbuvir, and its chemical name is S-2-(((S)-(((2R,3R,4R,5R)-5-(2,4-oxo-3, 4-Dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyl-tetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propionic aci...

Embodiment 3

[0048] Embodiment 3: Preparation of new crystal form of Sofosbuvir

[0049] Dissolve 1 g of sofosbuvir in 10 mL of diethyl oxalate at 50°C, slowly cool to room temperature, and volatilize and crystallize. After no more solids were precipitated, the crystals were collected by filtration, washed with a small amount of cold solvent (hexane or dichloromethane), and then sent to determine single crystal X-ray diffraction.

[0050] Its single crystal X-ray diffraction pattern has the following characteristics, the crystal belongs to the monoclinic system, the space group is P21, and the unit cell parameters: β = 108.96(3)°. unit cell volume The number of molecules in the unit cell is Z=2.

[0051] The drug used in the present invention is Sofosbuvir, and its chemical name is S-2-(((S)-(((2R,3R,4R,5R)-5-(2,4-oxo-3, 4-Dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyl-tetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propionic acid iso Propyl ester, molecular formula C...

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Abstract

The invention discloses a sofosbuvir monocrystal M and a preparation method and applications of the sofosbuvir monocrystal M. The sofosbuvir monocrystal prepared according to the preparation method disclosed by the invention belongs to a monoclinic system, and the space group is P21; the unit cell parameters are as follows: a=13.816 (3) A, b=5.973 (2) A, c=17.666 (4) A, and Beta=108.96 (3); the unit cell volume is 1378.7 (3) A3, and the number Z of molecules in a unit cell is 2. Solvents selected in the sofosbuvir monocrystal M disclosed by the invention are methylene chloride, chloroform, ethanol, isopropanol, acetonitrile, and C3-C7 alkyl cyanoacetate or C3-C7 dialkyl carbonate or C3-C7 dialkyl oxalate, and the like, and the sofosbuvir monocrystal is prepared by using a solvent evaporation method. The sofosbuvir monocrystal prepared according to the preparation method disclosed by the invention has good stability.

Description

technical field [0001] The invention relates to a sofosbuvir single crystal M and its preparation method and application. Background technique [0002] Gilead's hepatitis C drug Sofosbuvir (trade name: Sovaldi, generic name: Sofosbuvir, formerly known as GS-7977, PSI-7977, 400mg tablet) was approved by the US Food and Drug Administration on December 6, 2013 FDA approved for the treatment of adult patients with genotype 1, 2, 3 and 4 chronic hepatitis C (Hepatitis C). Sofosbuvir is the first drug approved for the full oral treatment of hepatitis C. When used for the treatment of specific genotypes (type 2, type 3) of chronic hepatitis C, it can eliminate the need for traditional injection drug interferon ( IFN) demand. [0003] [0004] [0005] Sofosbuvir is an inhibitor of hepatitis C virus NS5B polymerase. For HCV genotype 2 (HCV GT2) and HCV genotype 3 (HCV GT3) infection, Sofosbuvir only needs to be combined with Ribavirin It is therefore the world's first all-o...

Claims

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Application Information

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IPC IPC(8): C07H19/10C07H1/06A61K31/7072A61P1/16A61P31/14
CPCC07B2200/13C07H1/06C07H19/10
Inventor 汤律进周守明王彩琴冯汝宏
Owner 汤律进
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