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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

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 of the mesophase is not high, Mixed with amorphous, amorphous is thermodynamically unstable, and there is a risk of crystal transformation in the subsequent process

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

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Experimental program
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Effect test

Embodiment 1

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

[0081] Dissolve 200 mg of amorphous sodium 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetate in 1.0 mL In pure water, a clear solution was obtained, stirred at room temperature for 24 hours until solids were precipitated, and the wet solids were collected for XRPD testing to obtain Form I. Its XRPD pattern is as follows figure 1 As shown, the DSC diagram is shown in figure 2 As shown, the TGA graph is shown as image 3 shown.

[0082] Table 1 Powder X-ray Diffraction Data of Form I

[0083] 2theta

[0084] 17.55

[0085] 28.77

Embodiment 2

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

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

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

[0090] 2theta

[0091] 23.63

Embodiment 3

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

[0094] Dissolve 3.8 mg of amorphous sodium 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetate in 2.0 mL of ethyl acetate solvent to obtain a clear solution, which was slowly evaporated at room temperature until solids were precipitated, and the solids were collected to obtain Form III. Its XRPD pattern is as follows Figure 9 As shown, the DSC diagram is shown in Figure 10 As shown, the TGA graph is shown as Figure 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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