A kind of omeprazole sodium 1,2-propylene glycol solvate and preparation method

A technology of omeprazole sodium and solvate, applied in the field of chemical engineering crystallization, can solve the problems of inconvenient aseptic operation in pharmaceutical production, need preparation of crystal seeds, etc., and achieves high crystal purity, short time consumption and high efficiency Effect

Active Publication Date: 2017-06-20
TIANJIN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, this patent adopts the preparation method of reacting omeprazole and sodium hydroxide in ethanol and adding seed crystals to crystallize, which requires the preparation of seed crystals, which is not convenient for aseptic operation in pharmaceutical production

Method used

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  • A kind of omeprazole sodium 1,2-propylene glycol solvate and preparation method
  • A kind of omeprazole sodium 1,2-propylene glycol solvate and preparation method
  • A kind of omeprazole sodium 1,2-propylene glycol solvate and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Add 3.00 g of omeprazole sodium amorphous powder to 10 mL of 1,2-propanediol and stir for 2 hours at 60°C. Then it was filtered, and the filter cake was dried at 60° C. and a vacuum of 0.05 MPa for 2 hours. Obtained 3.46 g of omeprazole sodium 1,2-propanediol solvate with a molar yield of 95.5%.

[0038] The X-ray powder diffraction pattern of the obtained omeprazole sodium 1,2-propanediol solvate and attached figure 1 Consistent, solid Fourier transform infrared spectroscopy and attached figure 2 In agreement, the DSC transition temperature is 150.1°C, the decomposition temperature is 220.6°C, and the main crystal grain size is 120μm, without coalescence.

Embodiment 2

[0040] Add 7.20g of omeprazole sodium monohydrate to 18mL of 1,2-propanediol, add 90mL of n-heptane at a time under stirring at 60℃, then continue to add 60mL of n-heptane at a rate of 1mL / min, and then continue stirring 5 hours. The crystal slurry is filtered, and the filter cake is dried at 20°C under normal pressure for 4 hours. Obtained 7.95 g of omeprazole sodium 1,2-propanediol solvate with a molar yield of 96.0%.

[0041] The X-ray powder diffraction pattern of the obtained omeprazole sodium 1,2-propylene glycol solvate at the diffraction angle 2θ was 5.90, 10.80, 11.72, 15.52, 20.32, 20.92, 22.58, 22.96, 23.92, 24.44, 24.64, 25.30, 26.32 , 27.86, 29.72, 31.74, 32.46 degrees have characteristic diffraction peaks, solid Fourier transform infrared spectroscopy in the wave number is 3421.3,2931.5,2362.2,1613.3,1567.6,1475.6,1389.6,1268.2,1201.3,1153.8,1077.4,1026.4,836.2 ,832.4,629.5cm -1 There is a characteristic absorption peak, the DSC transition temperature is 149.7℃, t...

Embodiment 3

[0043] 7.20g of omeprazole sodium amorphous powder was added to 14mL of 1,2-propanediol, and the temperature was lowered to 30°C at a rate of 0.5°C / min at 50°C with stirring. Add 15 mL of ethyl acetate at one time, and continue stirring for 3 hours. The crystal slurry is filtered, and the filter cake is dried for 4 hours at 40° C. and 0.08 MPa vacuum. Obtained 8.44 g of omeprazole sodium 1,2-propanediol solvate with a molar yield of 97.1%.

[0044] The X-ray powder diffraction pattern of the obtained omeprazole sodium 1,2-propylene glycol solvate at the diffraction angle 2θ is 5.82, 10.82, 11.74, 15.56, 20.30, 20.94, 22.56, 22.94, 23.94, 24.46, 24.68, 25.34, 26.34 , 27.86, 29.70, 31.76, 32.44 degrees have characteristic diffraction peaks, solid Fourier transform infrared spectroscopy in the wave number is 3422.8,2931.6,2364.1,1613.1,1568.6,1475.4,1387.9,1268.7,1201.6,1153.3,1075.8,1026.1,838.0 ,831.9,627.6cm -1 There is a characteristic absorption peak, the DSC transition tempe...

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Abstract

The present invention discloses an esomeprazole sodium 1,2-propylene glycol solvate and a preparation process thereof, wherein X-ray powder diffraction spectrogram has characteristic diffraction peaks when a diffraction angle 2theta is 5.84+ / -0.1, 10.88+ / -0.1, 11.78+ / -0.1, 15.58+ / -0.1, 20.36+ / -0.1, 20.98+ / -0.1,22.54+ / -0.1, 22.90+ / -0.1, 23.98+ / -0.1, 24.42+ / -0.1, 24.68+ / -0.1, 25.32+ / -0.1, 26.36+ / -0.1, 27.82+ / -0.1, 29.76+ / -0.1, 31.74+ / -0.1, and 32.40+ / -0.1. The starting material esomeprazole sodium is added to the 1,2-propylene glycol, the mixture is stirred at a temperature of 10 to 60 DEG C for 2 to 9 hours, and through filtering and drying, the esomeprazole sodium 1,2-propylene glycol solvate is obtained. The preparation process according to the present invention is simple, achieves a high yield, and obtains safe and nontoxic solvent. The obtained product esomeprazole sodium 1,2-propylene glycol solvate has a greater crystalline granularity, fails to be aggregated simply, and achieves a good stability.

Description

Technical field [0001] The invention belongs to the technical field of chemical engineering crystallization, and relates to a 1,2-propanediol solvate of omeprazole sodium and a preparation method thereof. Background technique [0002] Omeprazole Sodium is chemically named 5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}- 1H-benzimidazole sodium salt, molecular formula C 17 H 18 N 3 NaO 3 S, the relative molecular mass is 367.4, and the structural formula is as follows: [0003] [0004] The active ingredient of omeprazole sodium is omeprazole, which is converted into sulfenamide derivatives in the body, its sulfur atom and H + ,K + -The sulfhydryl groups on the ATPase (proton pump) combine to make H + The pump is inactivated, reducing gastric acid secretion. But omeprazole has poor water solubility, so its injections are often made in the form of sodium salt. [0005] Patent US4738974A reports the medicinal salt of omeprazole, such as sodium salt, and prepares the h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 鲍颖陶灵刚李龙郝红勋吕军侯宝红
Owner TIANJIN UNIV
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