Amorphous substance of canagliflozin and preparation method of amorphous substance

An amorphous, endothermic peak technology, applied in the field of medicine, can solve the problems of high industrialization cost and poor control, and achieve the effects of simple preparation method, good stability, and good preparation adaptability

Inactive Publication Date: 2014-10-29
CHONGQING PHARMA RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally, the preparation of amorphous is spray drying, melting solidification or rapid evaporation solvent solidification, etc. These methods have high industrialization costs and are difficult to control.

Method used

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  • Amorphous substance of canagliflozin and preparation method of amorphous substance
  • Amorphous substance of canagliflozin and preparation method of amorphous substance
  • Amorphous substance of canagliflozin and preparation method of amorphous substance

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Preparation of Canagliflozin Amorphous Form

[0057] Dissolve 20g of canagliflozin in 80ml of ethyl acetate at 50-60°C, add dropwise to 160ml of cyclohexane solution at room temperature, stir while adding dropwise, continue stirring for 1 hour at room temperature after the dropwise addition, precipitate solid, and filter; The filter cake was dried at 30-40°C to obtain 18 g of amorphous canagliflozin, HPLC: 99.5%. Test X-ray powder diffraction, the results are as follows figure 1 ;Test TG-DSC, the result is as follows figure 2 ;Test the infrared spectrum, the result is as follows image 3 ;Test granularity, the result is as follows Figure 4 .

Embodiment 2

[0058] Embodiment 2 (comparative embodiment)

[0059] Preparation of Canagliflozin Amorphous Form

[0060] Dissolve 10g of canagliflozin in 100ml of ethyl acetate at 30-40°C, quickly distill off the solvent under reduced pressure at 40-50°C to obtain a solid powder; dry under reduced pressure at 40-50°C to obtain 9.9g of canagliflozin amorphous, HPLC: 99.5%. Test X-ray powder diffraction, the results are as follows Figure 5 ;Test TG-DSC, the result is as follows Image 6 .

[0061]

Embodiment 3

[0063] Preparation of Canagliflozin Amorphous Form

[0064] Dissolve 50g of canagliflozin in 300ml of toluene at 20-30°C, add dropwise to 150ml of n-hexane solution with an internal temperature of 0-10°C under stirring, continue to stir for 0.5h at 0-10°C after the dropwise addition, and a solid precipitates , filtered; the filter cake was dried under reduced pressure at 40-50° C. to obtain 43 g of canagliflozin amorphous, HPLC: 99.7%.

[0065] The resulting amorphous has Figure 1-3 Characteristics.

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Abstract

The invention discloses an amorphous substance of canagliflozin and a preparation method of the amorphous substance. Through DSC (Differential Scanning Calorimetry) scanning, the amorphous substance is found to have an endothermic peak within the temperature range of 53-63 DEG C and has characteristic absorption peaks at the wavelengths of about 832cm<-1> and 809cm<-1> in an infrared spectrogram. The invention also discloses an application of the amorphous substance to preparation of drugs for treating type-2 diabetes.

Description

technical field [0001] The invention relates to the field of medicine, in particular to an amorphous canagliflozin substance, a preparation method thereof, and an application of the amorphous substance in medicine. Background technique [0002] Canagliflozin, chemical name: 1-(?-D-glucopyranosyl)-4-methyl-3-(5-(4-fluorophenyl)-2-thienylmethyl) Benzene, the structure of which is shown in formula I, can be prepared by the method disclosed in CN101801371. [0003] [0004] Canagliflozin is a selective type 2 sodium glucose cotransporter (SGLT2) inhibitor developed by Johnson & Johnson in the United States. It is mainly used for the treatment of type II diabetic patients who are ineffective through exercise or diet control. [0005] Canagliflozin is a poorly water-soluble compound and is generally used in solid form in preparations, so the study of its crystal form is of great significance. [0006] Patent CN101573368 discloses a hemihydrate crystal form of canagliflozin, w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/10
CPCC07D409/10
Inventor 林蒙唐远富冯浩陈浩樊斌叶文润
Owner CHONGQING PHARMA RES INST
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