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Omeprazole sodium semihydrate and preparation method thereof

A technology of omeprazole sodium and hemihydrate, which is applied in the field of chemical engineering and pharmaceutical crystallization, can solve the problems of long time, 10-24 hours, low thermal decomposition temperature, poor stability and the like, and achieves difficult coalescence and molar yield. High and stable effect

Active Publication Date: 2015-07-22
TIANJIN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The monohydrate has poor stability and a low thermal decomposition temperature of 209.0°C
This patent adopts the preparation method of omeprazole and alkali reaction crystallization. Two kinds of mixed solvents must be used, and the crystallization operation takes a long time, requiring 10 to 24 hours, and the efficiency is low.

Method used

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  • Omeprazole sodium semihydrate and preparation method thereof
  • Omeprazole sodium semihydrate and preparation method thereof
  • Omeprazole sodium semihydrate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Add 0.45g omeprazole sodium monohydrate, 20mL ethyl acetate and 10mL sec-butanol to the crystallizer, stir for 2 hours at 35°C and a magnetic sub-rotation speed of 200r / min, filter and dry to obtain omeprazole Sodium hemihydrate 0.42g, molar yield 95.6%, HPLC content 99.8%. X-ray powder diffraction pattern of the product and attached figure 1 Consistent, solid-state Fourier transform infrared spectroscopy and attached figure 2 Consistently, the DSC decomposition temperature is 227.5°C. The main particle size of the crystal is 92 μm, no coalescence, and the Carr index is 14.3%, indicating that it has good fluidity. It is still a white crystal after being placed at a high temperature of 60°C for ten days, and the X-ray diffraction pattern does not change significantly. The result of the thermal stability test at 60°C shows that the weight change rate is 2.4% in 10 days, and the thermal stability is good. Under the conditions of 40°C and 75% relative humidity for 3 day...

Embodiment 2

[0040] Add 2.40g omeprazole sodium monohydrate and 20mL methyl isobutyl ketone to the crystallizer, stir for 7 hours at 60°C and a mechanical stirring speed of 300r / min, filter, dry at 35°C and a vacuum of 0.05MPa to obtain Omeprazole sodium hemihydrate 2.27g, molar yield 96.8%, HPLC content 100.2%. The X-ray powder diffraction pattern of the product has characteristic peaks at diffraction angles 2θ of 6.34, 11.18, 12.26, 15.58, 16.02, 17.06, 19.12, 21.04, 22.66, 23.52, 24.10, 26.44 and 28.04 degrees. Solid Fourier transform infrared The spectra are at wavenumbers 3414.5, 3132.1, 2969.9, 2939.8, 2846.9, 2756.5, 1607.7, 1571.9, 1474.5, 1441.5, 1377.3, 1266.0, 1147.8, 1112.3, 1072.8, 1032.9, 901.3, 83, 83 -1 There are characteristic peaks, and the DSC decomposition temperature is 229.2°C. The main particle size of the crystal is 95 μm, no coalescence, and the Carr index is 13.9%, indicating that it has good fluidity. It is still a white crystal after being placed at a high tem...

Embodiment 3

[0042] Add 3.00 g of omeprazole sodium hydrate (water content 7.02%), 10 mL of tetrahydrofuran, 10 mL of formamide and 10 mL of methyl ethyl ketone into the crystallizer, and stir for 9 hours at 25° C. with a mechanical stirring speed of 600 r / min. Filter and dry at 30°C under a vacuum of 0.1 MPa to obtain 2.78 g of omeprazole sodium hemihydrate with a molar yield of 97.4% and an HPLC content of 100.0%. The X-ray powder diffraction pattern of the product has characteristic peaks at diffraction angles 2θ of 6.28, 11.16, 12.16, 15.62, 16.02, 17.02, 19.10, 21.00, 22.60, 23.44, 24.16, 26.42 and 28.02 degrees. Solid Fourier transform infrared The spectra are at wavenumbers 3413.0, 3132.3, 2968.7, 2938.1, 2846.8, 2754.6, 1605.4, 1572.1, 1474.6, 1441.5, 1375.8, 1266.2, 1146.8, 1111.0, 1074.2, 10362.9, 712.8, 83.8 cm -1 There are characteristic peaks, and the DSC decomposition temperature is 229.5°C. The main particle size of the crystal is 100μm, no coalescence, and the Carr index i...

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Abstract

The invention discloses omeprazole sodium semihydrate and a preparation method thereof. Every mole of omeprazole sodium semihydrate contains 0.5 mole of water, and an X-ray diffraction spectrum has characteristic peaks at diffraction angles 2Theta of 6.26+ / -0.1 degrees, 11.10+ / -0.1 degrees, 12.20+ / -0.1 degrees, 15.58+ / -0.1 degrees, 16.02+ / -0.1 degrees, 17.12+ / 0.1 degrees, 19.08+ / 0.1 degrees, 21.00+ / 0.1 degrees, 22.68+ / -0.1 degrees, 23.48+ / -0.1 degrees, 24.08+ / -0.1 degrees, 26.52+ / -0.1 degrees and 28.08+ / -0.1 degrees. The omeprazole sodium semihydrate is obtained by adding a raw material omeprazole sodium hydrate into an organic solvent, stirring the mixture for 2 to 9 hours at constant temperature of 25 to 60 DEG C and performing filtration and drying. The omeprazole sodium semihydrate is high in purity, stability and flowability and low in agglomeration rate, and has broader application prospect.

Description

technical field [0001] The invention belongs to the technical field of chemical engineering pharmaceutical crystallization, and relates to omeprazole sodium hemihydrate and a preparation method thereof. Background technique [0002] The chemical name of Omeprazole Sodium is 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, with a relative molecular mass of 367.4, has the following structural formula: [0003] [0004] Omeprazole sodium is a racemic mixture of a pair of active optical enantiomers, which reduces the secretion of gastric acid through a highly targeted effect, and is a special inhibitor of the acid pump in the gastric parietal cells. Omeprazole is fat-soluble and can be concentrated around the secretory tubules of parietal cells and converted into active sulfenamide derivatives. Compared with H2 receptor blockers, omeprazole sodium has significant curative effect, hig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
CPCC07D401/12C07B2200/13
Inventor 鲍颖陶灵刚李龙郝红勋吕军侯宝红
Owner TIANJIN UNIV
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