New crystal forms of sodium 2-(5-bro-4-(4-cyclopropylnaphthalene-1- yl)-4H-1,2,4-triazole-3-yl sulfenyl) acetate and preparation method thereof

A technology of cyclopropylnaphthalene and thiol, which is applied in the field of chemical medicine, can solve the problems of mesophase crystallinity, mixed amorphous, crystal transformation, etc., achieve good stability, and is conducive to long-term storage and placement. Simple operation effect

Inactive Publication Date: 2015-03-04
CRYSTAL PHARMATECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The polymorph B, polymorph B′, polymorph C, polymorph D and polymorph E in this patent are all prepared from polymorph A as the starting material; the crystallinity

Method used

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  • New crystal forms of sodium 2-(5-bro-4-(4-cyclopropylnaphthalene-1- yl)-4H-1,2,4-triazole-3-yl sulfenyl) acetate and preparation method thereof
  • New crystal forms of sodium 2-(5-bro-4-(4-cyclopropylnaphthalene-1- yl)-4H-1,2,4-triazole-3-yl sulfenyl) acetate and preparation method thereof
  • New crystal forms of sodium 2-(5-bro-4-(4-cyclopropylnaphthalene-1- yl)-4H-1,2,4-triazole-3-yl sulfenyl) acetate and preparation method thereof

Examples

Experimental program
Comparison scheme
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Example Embodiment

[0079] Example 1

[0080] Preparation of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio) sodium acetate crystal form I:

[0081] Dissolve 200 mg of the amorphous form of sodium 2-(5-bromo-4-(4-cyclopropylnaphthalene-1-yl)-4H-1,2,4-triazol-3-ylthio)acetate in 1.0 mL Obtain a clear solution in pure water, stir at room temperature for 24 hours until a solid precipitates, collect the wet solid product and test XRPD to obtain crystal form I. Its XRPD diagram is like figure 1 As shown, the DSC chart is figure 2 As shown, the TGA diagram is as image 3 Shown.

[0082] Table 1 Powder X-ray diffraction data of crystal form Ⅰ

[0083] 2theta

[0084] 17.55

[0085] 28.77

Example Embodiment

[0086] Example 2

[0087] Preparation of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio) sodium acetate crystal form II:

[0088] Dissolve 50 mg of the amorphous form of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetate sodium in 0.5mL In the mixed system of ethyl acetate: water = 976:24 (v:v), stir at room temperature for more than 48 hours, and collect the solid to obtain crystal form II. Its XRPD diagram is like Figure 5 As shown, the DSC chart is Image 6 As shown, the TGA diagram is as Figure 7 Shown.

[0089] Table 2 X-ray powder diffraction data of crystal form Ⅱ

[0090] 2theta

[0091] 23.63

Example Embodiment

[0092] Example 3

[0093] Preparation of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio) sodium acetate crystal form III:

[0094] 3.8 mg of 2-(5-bromo-4-(4-cyclopropylnaphthalene-1-yl)-4H-1,2,4-triazol-3-ylthio) sodium acetate was dissolved in an amorphous form in 2.0 In mL of ethyl acetate solvent, a clear solution was obtained, which was slowly volatilized at room temperature until a solid precipitated. The solid was collected to obtain crystal form III. Its XRPD diagram is like Picture 9 As shown, the DSC chart is Picture 10 As shown, the TGA diagram is as Picture 11 Shown.

[0095] Table 3 X-ray powder diffraction data of crystal form Ⅲ

[0096] 2theta

[0097] 20.05

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Abstract

The invention relates to four novel crystal forms of 2-(5-bromine-4(4-cyclopropyl naphthaline)-1-yl)-4H-1,2,4-triazole-3-yl-sulfenyl) sodium acetate. The invention also provides a preparation method for the novel crystal forms of 2-(5-bromine-4(4-cyclopropyl naphthaline)-1-yl)-4H-1,2,4-triazole-3-yl-sulfenyl) sodium acetate.

Description

technical field [0001] The present invention relates to the field of chemical medicine, in particular to 2-(5-bromo-4-(4-cyclopropylnaphthalene-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid Crystal forms of sodium and methods for their preparation. Background technique [0002] 2-(5-Bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid (Lesinurad), manufactured by AstraZeneca ) is a uricosuric oral drug that treats gout patients with hyperuricemia by inhibiting the uric acid transporter URAT1 in the renal proximal tubule. At present, Lesinurad has reached the research endpoint in a phase III clinical trial, and compared with existing drugs, this drug has a better safety profile. It is predicted that by 2018, it is expected to become the dominant player in the gout drug market. The structure of its sodium salt is shown below: [0003] [0004] Polymorphism exists widely in pharmaceuticals. Different crystal forms of the same drug have significant ...

Claims

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Application Information

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IPC IPC(8): C07D249/12
CPCC07B2200/13C07D249/12
Inventor 陈敏华张炎锋杨朝惠张晓宇王鹏李丕旭
Owner CRYSTAL PHARMATECH CO LTD
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