C crystal form of canagliflozin and crystal preparation method of canagliflozin

A technology of canagliflozin and crystal form, which is applied in the field of fine chemical industry and application, can solve the problems of many steps in the crystallization method, and achieve the effect of low cost, high solubility, and easy commercial industrialization scale implementation

Inactive Publication Date: 2014-07-23
TIANJIN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] Patents CN200880106239.X and WO2012154812A1 disclose the compound crystal form of canagliflozin and its crystallization method. T

Method used

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  • C crystal form of canagliflozin and crystal preparation method of canagliflozin
  • C crystal form of canagliflozin and crystal preparation method of canagliflozin
  • C crystal form of canagliflozin and crystal preparation method of canagliflozin

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 5.08 g of dry canagliflozin solids with a purity of 92.0% into 100 mL of isopropanol to form a suspension, heat the suspension to 35 °C under stirring, and dissolve all the solids. Add 200mL of n-hexane dropwise to the solution, then cool down to 5°C at a rate of 0.05°C / min to obtain a suspension; filter the resulting suspension and dry the obtained wet product at 30°C and a vacuum of 0.07MPa for 10 hours The crystal form C product of canagliflozin was obtained. The X-ray powder diffraction pattern of the product is as follows: figure 1 As shown, it has characteristic peaks at diffraction angles 2θ=3.42, 6.55, 12.74, 15.89, 19.85, 24.37, 24.80, and 29.13 degrees; the DSC analysis diagram is as follows figure 2 As shown, it has a characteristic endothermic peak at 68.3 °C. Microscopic pictures of the crystal shape as image 3 shown.

[0032] The prepared crystal form C canagliflozin product has good stability, with a purity of 99.3% and a yield of 89.9%. After t...

Embodiment 2

[0034] Add 13.28 g of dried canagliflozin solids with a purity of 94.0% into 100 mL of absolute ethanol to form a suspension, heat the suspension to 55 °C under stirring, and dissolve all the solids. Add 250mL of n-octane and 200mL of mixed eluent of n-butyl ether dropwise into the solution, then cool down to -5°C at a rate of 1.5°C / min to obtain a suspension; filter the resulting suspension and filter the resulting wet product Drying for 7 hours at 40°C and a vacuum of 0.1 MPa to obtain the crystal form C product of canagliflozin. The X-ray powder diffraction pattern of the product has characteristic peaks at diffraction angles 2θ=3.43, 6.56, 12.74, 15.88, 19.85, 24.38, 24.82, and 29.15 degrees, and the DSC analysis diagram has characteristic endothermic peaks at 69.1°C.

[0035]The prepared crystal form C canagliflozin product has good stability, with a purity of 99.1% and a yield of 91.1%. After the product was stored under normal temperature and dry conditions for 100 days...

Embodiment 3

[0037] Add 22.03 g of dried canagliflozin solid with a purity of 93.0% into 30 mL of acetone and neutralize 70 mL of n-butanol to form a suspension, and heat the suspension to 65 ° C while stirring to dissolve all the solids. Add 600mL of cyclohexane dropwise to the solution at a speed of 0.3°C / min to -20°C to obtain a suspension; filter the resulting suspension and store the wet product at 35°C and a vacuum of 0.09MPa Drying at lower temperature for 8 hours to obtain the crystal form C product of canagliflozin. The X-ray powder diffraction pattern of the product has characteristic peaks at diffraction angles 2θ=3.43, 6.55, 12.74, 15.88, 19.86, 24.38, 24.83, and 29.14 degrees, and the DSC analysis diagram has characteristic endothermic peaks at 68.8°C.

[0038] The prepared crystal form C canagliflozin product has good stability, with a purity of 99.2% and a yield of 92.3%. After the product was stored under normal temperature and dry conditions for 100 days, the product purit...

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Abstract

The invention discloses a C crystal form of canagliflozin and a crystal preparation method of the canagliflozin. The X-ray powder of the canagliflozin, which is diffracted at diffraction angles 2 theta which are equal to 3.4 +/- 0.1, 6.5 +/- 0.1, 12.7 +/- 0.1, 15.8 +/- 0.1, 19.8 +/- 0.1, 24.3 +/- 0.1, 24.8 +/- 0.1 and 29.1 +/- 0.1, has characteristic peaks and is called as C crystal form canagliflozin. The method has the beneficial effects of being simple to operate and less in energy consumption. The prepared novel crystal form product is good in stability, large in solubility and rapid in dissolution rate; the purity of the novel crystal product is higher than 99% and the yield of the novel crystal product is 91% or so; the purity, the color and the shape of the novel crystal product are not changed after the novel crystal product is stored for 100 days at a normal temperature under a drying condition. The novel crystal product can be easily smashed and is easily compatible with the dosage forms of medicine compositions as well as is low in cost. Thus, the novel crystal product is easily suitable for large-scale commercial and industrial applications.

Description

technical field [0001] The invention belongs to fine chemical industry and its application, in particular to a new crystal form of canagliflozin and its crystallization preparation method. Background technique [0002] The chemical name of canagliflozin is 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl] Benzene, with the molecular formula C 24 h 25 FO 5 S, the molecular weight is 444.52, and the structural formula is as formula (I). Canagliflozin, as a sodium-dependent glucose transport protein (SGLT) inhibitor, was approved by the U.S. Food and Drug Administration (FDA) on March 29, 2013. Its tablets are used in combination with diet and exercise for adult type 2 Diabetics control blood sugar. [0003] [0004] Diabetes is a chronic disease that plagues the world. At present, there are about 230 million patients in the world. By 2025, the number of diabetic patients will increase to 300 million. Type 2 diabetes usually occurs after the age of ...

Claims

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Application Information

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IPC IPC(8): C07D409/10A61P3/10A61P9/10A61P25/00A61P13/12
CPCC07D409/10
Inventor 郝红勋张洪姣范传文侯宝红高永宏尹秋响齐宪亮王静康王永莉
Owner TIANJIN UNIV
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