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Novel crystal form of cefuroxime acid and preparation method thereof

A technology of cefuroxime acid and crystal form, which is applied in the field of new crystal form of cefuroxime acid and its crystal preparation, can solve the problems of poor crystal form of cefuroxime acid, high labor intensity, difficulty in filtration and drying, etc., and achieves thermal stability Good, low labor intensity, complete crystal form effect

Active Publication Date: 2012-10-24
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Cefuroxime acid products generally have poor crystal shape, dull appearance, small particle size and serious agglomeration, which makes filtration and drying difficult during the production process and labor-intensive
In addition, the solvents used in the production process of cefuroxime acid and its solvates are relatively toxic and costly

Method used

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  • Novel crystal form of cefuroxime acid and preparation method thereof
  • Novel crystal form of cefuroxime acid and preparation method thereof
  • Novel crystal form of cefuroxime acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 5g of cefuroxime sodium to a container containing 50ml of acetonitrile and N,N-dimethylformamide mixed solvent (volume ratio 1:9), stir and dissolve at a constant temperature of 25°C, and after continuous stirring for 30 minutes, Filter and decolorize. Transfer the filtrate into a crystallizer, add 6mol / l hydrochloric acid solution to adjust the pH of the solution to 3, cool to 15℃, add 0.25g seed crystals, grow crystals for 1h, add 50ml eluent water, continue to cool to 5℃, grow crystals for 1h After suction filtration, the filter cake was washed with 10 ml of pure water, and dried at 30° C. under a vacuum of 0.08 MPa for 5 hours. The molar yield of the final crystal product was 88.3%. The HPLC purity is 99.3%, and the main particle size is 120 μm.

[0027] The XRD pattern of the resulting product is as figure 2 As shown, the infrared absorption spectrum is as image 3 As shown, the scanning electron microscope photos are as Figure 4 Shown.

Embodiment 2

[0029] Add 5g of cefuroxime acid to a container containing 30ml of a mixed solvent of acetonitrile and acetone (volume ratio 1:5), stir to dissolve at a constant temperature of 30°C, continue stirring for 40 minutes, filter and decolorize. Transfer the filtrate into a crystallizer, add 3mol / l hydrochloric acid solution to adjust the pH of the solution to 3.5, cool to 15°C, add 0.15g seed crystals, grow the crystals for 2h, add 100ml of eluent ethyl acetate, and continue to cool to 2°C. After crystallizing for 3 hours, filter with suction, wash the filter cake with 10ml ethyl acetate, and dry for 12 hours at 40°C under a vacuum of 0.05MPa. The molar yield of the final crystal product was 90.2%. The HPLC purity is 99.5%, and the main particle size is 130 μm.

[0030] The XRD of the product has characteristic peaks at 8.06, 9.96, 10.45, 11.84, 12.82, 16.33, 19.02, 20.03, 21.86, 23.22, 25.46, 25.99, 33.12, 34.22 and 36.40 degrees. The infrared absorption spectrum is at 3396.03, 3296...

Embodiment 3

[0032] Add 25g of cefuroxime sodium to a container containing 125ml of mixed solvent of acetonitrile and N,N-dimethylformamide (volume ratio 1:4), stir and dissolve at a constant temperature of 35°C, and after continuous stirring for 60 minutes, Filter and decolorize. Transfer the filtrate into a crystallizer, add 6mol / l hydrochloric acid solution to adjust the pH of the solution to 3.8, cool to 10°C, add 0.025g seed crystals, grow crystals for 1.3h, add 550ml eluent water, continue to cool to 0°C, grow crystals After 2.5h, filter with suction, wash the filter cake with 40ml pure water, and dry for 7h at a vacuum of 0.09MPa at 50°C. The molar yield of the final crystal product was 91.5%. The HPLC purity is 99.4%, and the main particle size is 110 μm.

[0033] The XRD of the product has characteristic peaks at 8.07, 9.96, 10.44, 11.85, 12.82, 16.34, 19.03, 20.02, 21.86, 23.21, 25.46, 25.98, 33.14, 34.24 and 36.40 degrees. The infrared absorption spectrum is at 3396.01, 3296.56, ...

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Abstract

The invention relates to a novel crystal form of cefuroxime acid and a preparation method thereof. In X ray powder diffraction, the novel crystal form of cefuroxime acid has characteristic peaks at diffraction angles 2 theta of 8.06, 9.96, 10.44, 11.84, 12.82, 16.34, 19.02, 20.02, 21.86, 23.22, 25.46, 25.98, 33.12, 34.24 and 36.40 degrees. The preparation method comprises the following steps of adding cefuroxime raw materials into an acetonitrile mixed solvent to obtain a solution having a concentration of 0.1 to 0.2g / ml, stirring at a temperature of 25 to 35 DEG C for complete dissolution, continuously stirring for 30 to 60 minutes, carrying out filtration and decoloration, transferring filtrate to a crystallizer, adding a hydrochloric acid solution into the crystallizer to adjust a pH value of the mixed solution to 3-4, cooling to a temperature of 10 to 15 DEG C, adding cefuroxime acid seed crystals into the crystallizer, carrying out crystallization for 1 to 2 hours, adding water as a solventing-out agent into the crystallizer, sequentially cooling to a temperature of 0 to 5 DEG C, carrying out crystallization for 1 to 3 hours, filtering, washing filter cake by a washing solvent, and drying to obtain products. The novel crystal form of cefuroxime acid has HPLC content above 99.3%, avoids crystal accumulation, has large particle sizes, wherein a main particle size is more than 100 microns, and also has uniform particle size distribution and a single-cycle mole yield above 88% in crystallization.

Description

Technical field [0001] The invention belongs to the technical field of crystallization, and particularly relates to a new crystal form of cefuroxime acid and a crystal preparation method thereof. Background technique [0002] The chemical name of Cefuroxime acid is (6R,7R)-7-[2-furyl(methoxyimino)acetamido]-3-carbamoyloxymethyl-8-oxo-5- Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, molecular formula is C 16 H 16 N 4 O 8 S, molecular weight is 424.39, CAS number: 55268-75-2, and its chemical structure is shown below. [0003] [0004] Cefuroxime acid is an intermediate in the production of the second generation antibiotics cefuroxime sodium and cefuroxime axetil. Cefuroxime antibiotics are broad-spectrum antibiotics. They have obvious antibacterial activity against Gram-negative bacteria and Gram-positive bacteria. They can be used to treat respiratory infections, ear, nose, and throat infections, and urinary infections caused by sensitive bacteria. Tract infections, skin a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/12
Inventor 王永莉王冠龚俊波张美景尹秋响刘东侯宝红王静康谢闯周丽娜
Owner TIANJIN UNIV
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