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Mefenamic acid-piperazine salt form and preparation method thereof

A technology of mefenamic acid and piperazine, applied in the field of a salt form of mefenamic acid and its preparation, can solve the problem of low solubility of mefenamic acid

Active Publication Date: 2019-09-20
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to overcome the deficiencies of the prior art and solve the problem of low solubility of the existing mefenamic acid, the present invention provides a salt form of mefenamic acid-piperazine

Method used

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  • Mefenamic acid-piperazine salt form and preparation method thereof
  • Mefenamic acid-piperazine salt form and preparation method thereof
  • Mefenamic acid-piperazine salt form and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Accurately weigh 724mg of mefenamic acid and 155mg of piperazine, place them in a 50ml crystallizer, add 35g of methanol to it, heat to 30°C, and stir to dissolve the solid part to form a suspension. Keep the temperature constant at 30°C and continue to stir to carry out reaction crystallization. After continuous stirring for 12 hours, the obtained solid was filtered while it was hot, washed with the mother liquor, and dried at 25° C. under normal pressure for 6 hours, and the obtained product was the mefenamic acid-piperazine salt type.

[0035] The powder X-ray diffraction pattern of the product has characteristic peaks at 2θ at 4.7, 9.8, 13.9, 15.4, 18.6, 23.4, 25.2, 25.4, 26.8, 29.4, and 33.4 degrees, and DSC shows that its melting point is 170.12 ° C, confirming that the obtained solid is Mefenamic acid-piperazine salt type. In the water-ethanol mixed solvent with a volume ratio of 1:1, the concentration of mefenamic acid in the saturated solution at 37°C was meas...

Embodiment 2

[0037] Accurately weigh 745mg of mefenamic acid and 155mg of piperazine, place them in a 50ml crystallizer, add 54g of methanol to it, heat to 20°C, and stir to dissolve the solid part to form a suspension. Keep the temperature constant at 20°C and continue to stir to carry out reaction crystallization. After continuous stirring for 12 hours, the obtained solid was filtered while it was hot, washed with the mother liquor, and dried at 25° C. under normal pressure for 8 hours, and the obtained product was the mefenamic acid-piperazine salt type.

[0038] The powder X-ray diffraction spectrum of the product has characteristic peaks at 2θ of 4.6, 9.7, 13.9, 15.2, 18.6, 23.5, 25.3, 25.5, 26.7, 29.5, 33.4 degrees, and DSC shows that its melting point is 169.92 ° C, confirming that the obtained solid is Mefenamic acid-piperazine salt type. In the water-ethanol mixed solvent with a volume ratio of 1:1, the concentration of mefenamic acid in the saturated solution at 37°C was measure...

Embodiment 3

[0040] Accurately weigh 930mg of mefenamic acid and 155mg of piperazine, place them in a 100ml crystallizer, add 50g of ethanol to it, heat to 40°C, and stir to dissolve the solid part to form a suspension. Keep the temperature constant at 40°C and continue to stir to carry out reaction crystallization. After continuous stirring for 10 hours, the obtained solid was filtered while it was hot, washed with mother liquor, and dried at 25° C. under normal pressure for 8 hours, and the obtained product was the mefenamic acid-piperazine salt type.

[0041] The powder X-ray diffraction pattern of the product has characteristic peaks at 2θ at 4.5, 9.8, 13.9, 15.3, 18.5, 23.5, 25.2, 25.6, 26.7, 29.4, 33.5 degrees, and DSC shows that its melting point is 169.54 ° C, confirming that the obtained solid is Mefenamic acid-piperazine salt type. In the water-ethanol mixed solvent with a volume ratio of 1:1, the concentration of mefenamic acid in the saturated solution at 37°C was measured to be...

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Abstract

The invention discloses a mefenamic acid-piperazine salt form and a preparation method of the mefenamic acid-piperazine salt form. The mefenamic acid-piperazine salt form disclosed by the invention is an asymmetric unit formed by one deprotonated mefenamic acid and 0.5 protonated piperazine, and the space group of the asymmetric unit is an orthogonal P bca crystal system; wherein the crystallographic characteristics are as follows: alpha = beta = gamma = 90 degrees. The preparation method comprises the following steps: adding mefenamic acid and piperazine into an organic solvent, heating to enable the mefenamic acid and the piperazine to be partially dissolved, and performing a reaction to obtain a suspension; and stirring the suspension for reaction, filtering the crystal slurry, washing the crystal slurry with mother liquor, and drying the product to obtain the mefenamic acid-piperazine salt form. The method is simple to operate and good in reproducibility. The salt form has good thermodynamic stability and solubility, and the solubility of the salt form is 6.15 times that of mefenamic acid.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical crystallization, and in particular relates to a salt form of mefenamic acid and a preparation method thereof. Background technique [0002] Mefenamic acid, also known as mefenamic acid, is also an intermediate for the preparation of acridine antimalarials and anticancer drugs. It is a non-steroidal anti-inflammatory analgesic that has been used in clinical practice for a long time. It is widely used in the treatment of rheumatism, rheumatoid arthritis, dysmenorrhea, headache, toothache, neuralgia, muscle pain and post-operative and other inflammatory pain. Because mefenamic acid has broad application prospects, all countries have been expanding production scale in recent years. However, mefenamic acid belongs to the second class of BCS drugs and has poor water solubility, which limits its bioavailability. [0003] Mefenamic acid, the chemical name is N-(2,3-xylyl)-2-aminobenzoic acid, and...

Claims

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Application Information

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IPC IPC(8): C07D295/023C07D295/027C07C227/42C07C227/18C07C229/58
CPCC07D295/023C07D295/027C07C227/42C07C227/18C07C229/58C07B2200/13
Inventor 龚俊波王馨逸刘裕陈艺夫侯宝红尹秋响
Owner TIANJIN UNIV
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