Canagliflozin crystal form e, crystal form f and preparation method thereof

A crystal form and crystallization technology, applied in the field of chemical medicine, can solve the problems of poor crystallinity, poor fluidity, and unstable baseline of C crystal form, achieve good physical and chemical stability, improve drug solubility and dissolution rate, Process controllable effect

Active Publication Date: 2018-02-02
CRYSTAL PHARMATECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Patents CN103980261A, CN103980262A and CN103936725A disclose A crystal form, B crystal form and C crystal form of canagliflozin. According to the patent data, A and B crystal forms are flaky structures with poor fluidity; C crystal form The stability is not good, the baseline is unstable and almost all broad peaks, there is the possibility of mixed crystals, and the stability needs to be further verified

Method used

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  • Canagliflozin crystal form e, crystal form f and preparation method thereof
  • Canagliflozin crystal form e, crystal form f and preparation method thereof
  • Canagliflozin crystal form e, crystal form f and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] Embodiment 1: Preparation of the crystal form E of canagliflozin

[0090] Dissolve 499.5 mg of canagliflozin powder in 13.25 mL of acetic acid: n-heptane = 1:3 (v:v) mixed system, and then quickly place it at -20°C and stir for 20 hours. The obtained solid is crystal Type E. Its XRPD pattern is shown in figure 1 , whose DSC diagram is shown in figure 2 , whose TGA diagram is shown in image 3 .

[0091] The corresponding values ​​of 2theta value and intensity of crystal form E in this embodiment are shown in Table 1:

[0092] Table 1 Corresponding value of 2theta value and intensity of crystal form E

[0093] 2theta

[0094] 38.89

Embodiment 2

[0095] Embodiment 2: Preparation of crystal form E of canagliflozin

[0096] Dissolve 19.6 mg of canagliflozin powder in 0.20 mL of acetic acid: n-heptane = 1:1 (v:v) mixed solvent, then quickly place it at -20°C and stir for 20 hours, and the obtained solid is crystal Type E.

[0097] The corresponding values ​​of 2theta value and relative intensity of crystal form E in this embodiment are shown in Table 2:

[0098] Table 2 Corresponding value of 2theta value and relative intensity of crystal form E

[0099] 2theta

Embodiment 3

[0100] Embodiment 3: Preparation of crystal form E of canagliflozin

[0101] Dissolve 21.1 mg of canagliflozin powder in 0.40 mL of acetic acid solvent, then add 0.50 mL of n-heptane and stir at room temperature for 5 days, and the obtained solid is Form E.

[0102] The 2theta value and intensity corresponding value of crystal form E in this embodiment are shown in Table 3:

[0103] Table 3 Corresponding values ​​of 2theta value and intensity of crystal form E

[0104] 2theta

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PUM

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Abstract

The invention provides two new crystal forms: a crystal form E and a crystal form F, of canagliflozin, and the preparation method thereof. The new crystal forms are greatly improved in form and particle size. The particles are fine in size and are dispersed uniformly, so that it is beneficial to improvement of medicine solubility and dissolution rate, thereby being beneficial to preparation development.

Description

technical field [0001] The invention relates to the field of chemistry and medicine, in particular to crystal form E and crystal form F of canagliflozin, which can be used as a hypoglycemic drug for treating type II diabetes, and a preparation method thereof. Background technique [0002] Canagliflozin (canagliflozin, the compound shown in formula I), the chemical name is 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)- 2-Thienylmethyl]benzene, developed by Janssen Pharmaceuticals, a subsidiary of Johnson & Johnson, was approved by the FDA on March 29, 2013 as a hypoglycemic drug for the treatment of type 2 diabetes. It is the first drug approved by the FDA. A sodium-glucose cotransporter 2 (SGLT2) inhibitor. SGLT2 inhibitors can specifically inhibit the reabsorption of glucose by the kidneys, excrete excess glucose from the urine and directly reduce blood glucose levels. The structure of the drug molecule is shown below: [0003] [0004] It is well known that p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/10
CPCC07B2200/13C07D409/10
Inventor 陈敏华张炎锋杨朝惠陆飞张晓宇
Owner CRYSTAL PHARMATECH CO LTD
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