Crystal, preparation method and applications of crystal

A crystal form and recrystallization technology, which can be used in pharmaceutical formulations, medical preparations containing active ingredients, metabolic diseases, etc., can solve problems such as interference, and achieve the effect of reducing diabetic complications

Active Publication Date: 2014-07-23
王军
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, hemihydrate crystal form A (US 2008 / 0146515 A1 crystal form) is easily obtained in an aqueous solvent system, which interferes with the preparation of crystal forms B and C

Method used

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  • Crystal, preparation method and applications of crystal
  • Crystal, preparation method and applications of crystal
  • Crystal, preparation method and applications of crystal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Weigh about 10mg of 1-(b-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene into a glass bottle, at room temperature Add 0.4mL of n-octanol to dissolve the sample until clear, then place the sample at 5°C overnight (12h), the solid precipitates out, put the suspension in a filter centrifuge tube, and centrifuge at 4000rpm for 3 minutes to obtain The solid was detected by XRPD according to the method specified in this patent, and octanol and 1-(b-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)- The molar ratio of 2-thienylmethyl]benzene. The XRPD results show that the obtained solid position is crystal form III, and octanol and 1-(b-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl Base] The molar ratio of benzene is 0.5:1. X-ray powder diffraction in this patent, the operation and analysis steps are as follows:

[0038] The X-ray powder diffraction pattern was collected on a Bruker D8 Discover X-ray powder diffractometer of GADDS...

Embodiment 2

[0044] Weigh about 10mg of 1-(b-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene into a glass bottle, at room temperature Add 0.5mL of n-octanol to dissolve the sample until clear, then gradually add 3.05mL of n-heptane, crystallize and precipitate a solid, place the suspension in a filter centrifuge tube, and centrifuge at 4000rpm for 3 minutes to obtain a solid. The XRPD method is used for detection, and it is crystal form III.

Embodiment 3

[0046] Weigh about 10mg of 1-(b-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene into a glass bottle, at room temperature Add 0.5 mL of n-octanol to dissolve the sample until clear, take 3 mL of anti-solvent into a 20 mL glass bottle, put the 1.5 mL glass bottle containing the n-octanol solution of the compound into a 20 mL glass bottle, and let the anti-solvent gas diffuse Put the suspension into the sample solution, place the suspension in a filter centrifuge tube, and centrifuge at 4000rpm for 3 minutes to obtain a solid that is detected by the XRPD method described in Example 1 and is crystal form III. Here, n-hexane, pentane, cyclohexane, toluene, n-heptane, etc. can also be used as the anti-solvent.

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Abstract

The invention discloses crystal forms III and IV of 1-(b-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene. In an X-ray powder diffraction diagram, the crystal forms III and IV at least have characteristic peaks at 2q values being 6.61+/-0.2, 3.92+/-0.2 and 19.68+/-0.2, as well as 17.40+/-0.2, 15.35+/-0.2 and 14.91+/-0.2, respectively. The invention further discloses a preparation method and medical applications of the crystal. The crystal form III is an octanol complex and has more obvious action effect on the diabetes treatment effect. The crystal form IV is an anhydrous complex, and is high in purity; the drying process for preparing the anhydrous complex is simple; on the aspect of preparation technology, the anhydrous complex has obvious advantages compared with the hydrous complex.

Description

technical field [0001] The present invention relates to a novel crystal of 1-(b-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene and its preparation method and use . Background technique [0002] Diabetes mellitus is a group of endocrine-metabolic diseases with hyperglycemia as its common sign. Disorders of sugar, protein, fat and secondary water and electrolyte metabolism caused by absolute or relative insufficient secretion of insulin. It can involve chronic damage and dysfunction of various systems of the whole body, especially the eyes, kidneys, heart, blood vessels, and nerves, and even induce many fatal complications. With the aging of the world population, diabetes has become a common and frequently-occurring disease, and it is a disease that seriously endangers human health. Research data show that the number of diabetic patients worldwide has increased from 150 million in 2000 to 280 million, and it is estimated that nearly 500 million peo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/10A61K31/381A61P3/10A61P9/10A61P25/28A61P13/12A61P17/02A61P5/50A61P3/06A61P3/04A61P9/12A61P19/06
CPCC07D409/10A61K31/381
Inventor 王军
Owner 王军
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