Canagliflozin of crystal form B, and crystallization preparation method thereof

A canagliflozin and crystal form technology, which is applied in the fine chemical industry and application fields, can solve the problems of many steps in the crystallization method, and achieve the effects of low cost, short time consumption, and easy pulverization

Inactive Publication Date: 2014-08-13
TIANJIN UNIV +1
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  • 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. The crystallization method described in this document has many steps and needs to be carried out under the condition of argon protection.

Method used

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  • Canagliflozin of crystal form B, and crystallization preparation method thereof
  • Canagliflozin of crystal form B, and crystallization preparation method thereof
  • Canagliflozin of crystal form B, and crystallization preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 10.02 g of dry canagliflozin with a purity of 92.0% into 100 mL of isoamyl alcohol to form a suspension, heat the suspension to 48 ° C under stirring, and dissolve all the solids, and add to the solution at a speed of 0.3 mL / min 300mL of n-butane was added dropwise to obtain a suspension; then starting from 48°C, 80mL of solvent was evaporated within 5 hours; the suspension was filtered to obtain a wet crystal product, which was dried at 20°C under normal pressure for 10 hours to constant Weight, to obtain B crystal form canagliflozin product. 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, 6.64, 12.64, 13.27, 15.30, 15.65, 16.59, 19.45, 19.88, and 23.79 degrees. The DSC analysis diagram is as follows figure 2 As shown, there is an endothermic peak at 84.2°C, and its micrograph is shown in image 3 shown.

[0032] The prepared crystal form B canagliflozin product has...

Embodiment 2

[0034] Add 21.98 g of dry canagliflozin with a purity of 93.0% into 100 mL of n-propanol to form a suspension, heat the suspension to 55 °C under stirring, and dissolve all the solids, and add to the solution at a speed of 8.5 mL / min A mixed eluent of 550 mL of n-heptane and 300 mL of cyclohexane was added dropwise to obtain a suspension, and then from 55° C., 380 mL of solvent was evaporated within 10 hours; the obtained suspension was filtered to obtain a wet crystal product, and It was dried at 45° C. under normal pressure for 7 hours to constant weight to obtain crystal form B canagliflozin product. The X-ray powder diffraction pattern of the product has characteristic peaks at diffraction angles 2θ=3.41, 6.69, 12.67, 13.25, 15.30, 15.66, 16.58, 19.46, 19.88, 23.78 degrees, and DSC has an endothermic peak at 84.8°C.

[0035]The prepared crystal form B canagliflozin product has good stability, with a purity of 99.1% and a yield of 93.6%. After the product is stored under no...

Embodiment 3

[0037] Add 35.55 g of dry canagliflozin with a purity of 95.0% into 20 mL of sec-butanol and 80 mL of n-propanol to form a suspension, and heat the suspension to 60 °C under stirring to dissolve all the solids. Add 500mL of n-hexane dropwise to the solution at a high speed to obtain a suspension; then start from 60°C and evaporate 360mL of solvent within 8 hours; Dry for 6 hours to constant weight to obtain crystal form B canagliflozin product. The X-ray powder diffraction pattern of the product has characteristic peaks at diffraction angles 2θ=3.40, 6.69, 12.64, 13.26, 15.30, 15.65, 16.57, 19.43, 19.86, and 23.79 degrees, and DSC has an endothermic peak at 83.9°C.

[0038] The prepared crystal form B canagliflozin product has good stability, with a purity of 99.2% and a yield of 94.5%. After the product is stored under normal temperature and dry conditions for 100 days, the product has no change in purity, color and shape. The product is easy to crush and easy to add to the ...

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Abstract

The invention discloses a canagliflozin of crystal form B, and a crystallization preparation method thereof. The X-ray powder diffraction pattern of the canagliflozin of crystal form B has characteristic peaks at diffraction angles 2theta with the values of 3.4+ / -0.1, 6.6+ / -0.1, 12.6+ / -0.1, 13.2+ / -0.1, 15.3+ / -0.1, 15.6+ / -0.1, 16.5+ / -0.1, 19.4+ / -0.1, 19.8+ / -0.1 and 23.7+ / -0.1. The method has the advantages of high efficiency, easy operation and short time. Canagliflozin crystals of crystal form B prepared in the invention have a large solubility and a fast dissolving rate, the above product has a purity of above 99%, and has a yield of about 95%, and the purity, the color and the form of the product are unchanged after the product is stored under normal temperature dry conditions for 100d. The product has the advantages of easy crushing, easy addition of medicinal compositions, low cost, and easy commercial industrial large-scale enforcement.

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 follows. Canagliflozin is a sodium-dependent glucose transport protein (SGLT) inhibitor. On March 29, 2013, the US Food and Drug Administration (FDA) approved its tablet in combination with diet and exercise for adults with type 2 diabetes Patient controls blood sugar. [0003] [0004] Long-term high blood sugar increases the risk of serious complications, including heart disease, blindness, and nerve and kidney damage. With the improvement of living standards, the incidence of diabetes in children has also increased in recent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/10A61P3/10A61P27/02A61P25/00A61P13/12A61P5/48
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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