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Canagliflozin of crystal form A, and crystallization preparation method thereof

A crystal form and crystal technology, which is applied to the new crystal form of canagliflozin and its crystallization preparation field, can solve the problems of many steps in the crystallization method, and achieve the effects of low cost, short time consumption and low energy consumption

Inactive Publication Date: 2014-08-13
TIANJIN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] 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 A, and crystallization preparation method thereof
  • Canagliflozin of crystal form A, and crystallization preparation method thereof
  • Canagliflozin of crystal form A, and crystallization preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 5.1 g of dry canagliflozin solid with a purity of 92.0% into 100 mL of n-propanol to form a suspension, and heat the suspension to 15 °C under stirring to dissolve all the solids; Add 300 mL of cyclohexane dropwise to the solution to obtain a suspension, vacuum filter the crystal slurry, and dry the product at 30°C under normal pressure for 8 hours to constant weight to obtain the crystal form A 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=3.71, 3.94, 7.77, 7.92, 11.53, 13.16, 13.58, 14.30, 15.56, 17.32, 18.81, 19.36, 20.31, 22.50, 22.79, 23.24, 23.48 degrees, DSC analysis Figure such as figure 2 , which has a characteristic endothermic peak at 105.4°C. Microscopic pictures of the crystal shape as image 3 shown.

[0030] The prepared crystal form A canagliflozin product has good stability, with a purity of 99.3% and a yield of 88.3%. After the p...

Embodiment 2

[0032] Add 14.3 g of dry canagliflozin solids with a purity of 96.0% into 100 mL of isopropanol to form a suspension, and heat the suspension to 25 °C under stirring to dissolve all the solids; Add 400mL of n-hexane and 100mL of water as a mixed eluent dropwise to obtain a suspension, vacuum filter the crystal slurry, and dry the product at 45°C under normal pressure for 7 hours to constant weight to obtain the A crystal form net. The X-ray powder diffraction pattern of the product has characteristics at diffraction angles 2θ=3.73, 3.96, 7.78, 7.94, 11.53, 13.15, 13.57, 14.31, 15.58, 17.34, 18.82, 19.35, 20.32, 22.52, 22.79, 23.25, 23.48 degrees Peak, DSC analysis chart has a characteristic endothermic peak at 105.56°C.

[0033] The prepared crystal form A canagliflozin product has good stability, with a purity of 99.1% and a yield of 89.6%. After the product was stored under normal temperature and dry conditions for 100 days, the product purity, color and shape did not chang...

Embodiment 3

[0035] Add 28.5 g of dried canagliflozin solids with a purity of 94.0% into 40 mL of ethanol and 60 mL of n-pentanol to form a suspension, and heat the suspension to 38 °C under stirring to dissolve all the solids; Add 650 mL of petroleum ether dropwise to the solution at a high speed to obtain a suspension, vacuum filter the crystal slurry, and dry the product at 45°C under normal pressure for 6 hours to constant weight to obtain crystal form A of canagliflozin. The X-ray powder diffraction pattern of the product has characteristics at diffraction angles 2θ=3.74, 3.96, 7.77, 7.95, 11.55, 13.17, 13.58, 14.32, 15.59, 17.36, 18.82, 19.36, 20.33, 22.53, 22.78, 23.25, 23.48 degrees Peak, DSC analysis chart has a characteristic endothermic peak at 106.72°C.

[0036] The prepared crystal form A canagliflozin product has good stability, with a purity of 99.2% and a yield of 90.5%. 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 canagliflozin of crystal form A, and a crystallization preparation method thereof. The X-ray powder diffraction pattern of the canagliflozin of crystal form A has characteristic peaks at diffraction angles 2theta with the values of 3.7+ / -0.1, 3.9+ / -0.1, 7.7+ / -0.1, 7.9+ / -0.1, 11.5+ / -0.1, 13.1+ / -0.1, 13.5+ / -0.1, 14.3+ / -0.1, 15.5+ / -0.1, 17.3+ / -0.1, 18.8+ / -0.1, 19.3+ / -0.1, 20.3+ / -0.1, 22.5+ / -0.1, 22.7+ / -0.1, 23.2+ / -0.1 and 23.4+ / -0.1. The preparation method has the advantages of simplicity and easy operation of operation steps, short time and less energy consumption. The above product prepared in the invention has a good stability, high a purity of above 99%, and has a yield of about 90%, 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.

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 US Food and Drug Administration (FDA) on March 29, 2013 in conjunction with diet and exercise. Glucose cannot be successfully reabsorbed into the blood and excreted with urine, thereby reducing blood sugar concentration, and is used to control blood sugar in adults with type 2 diabetes. [0003] [0004] Diabetes is a chronic disease that plagues the world. At present, there are about 230 million patients in the worl...

Claims

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Application Information

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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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