CN103588716A - Novel crystal form of 2-(5-bromine-4-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-ylsulfenyl) acetic acid and preparation method thereof - Google Patents
Novel crystal form of 2-(5-bromine-4-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-ylsulfenyl) acetic acid and preparation method thereof Download PDFInfo
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- FGQFOYHRJSUHMR-UHFFFAOYSA-N OC(CSc([n]1-c2ccc(C3CC3)c3c2cccc3)nnc1Br)=O Chemical compound OC(CSc([n]1-c2ccc(C3CC3)c3c2cccc3)nnc1Br)=O FGQFOYHRJSUHMR-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
Abstract
The invention relates to a 2-(5-bromine-4-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-ylsulfenyl) acetic acid anhydrous compound and solvent compound polymorphism. The invention further provides a preparation method of a novel crystal form of 2-(5-bromine-4-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-ylsulfenyl) acetic acid.
Description
Affiliated technical field
The present invention relates to chemical field of medicaments, particularly relate to new crystal of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid and preparation method thereof.
Background technology
2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid is that a kind of uricosuric escape orifice is taken medicine, and treats the patient with gout of hyperuricemia by suppressing the sub-URAT1 of uric acid transporter of kidney proximal tubule.The structure of this medicine is as follows:
WO2012092395A2 discloses crystallization polymorphic forms 1 and the form 2 of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid.Polymorphic forms 1 is characterised in that, its X-ray diffractogram exists peak at ° 2 θ places, 10.32,18.84 and 20.75 ° of 2 θ ± 0.1.Polymorphic forms 2 is characterised in that, its x-ray diffraction pattern exists peak at ° 2 θ places, 10.46,18.76 and 19.83 ° of 2 θ ± 0.1.
WO2011085009A2 discloses crystallization polymorphic and the middle facies pattern of solid of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) sodium acetate.Comprise 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) sodium acetate polymorphic A, polymorph b, polymorph b ', polymorphic C, polymorphic D, polymorphic E and 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) the middle phase 1 of sodium acetate solid, phase 2 in the middle of solid, phase 3 in the middle of solid.
Summary of the invention
The invention provides the new crystal of four kinds of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid, called after crystalline form III in the present invention, crystalline form IV, crystalline form V, crystal formation VI.
On the one hand, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form III of acetic acid, it is characterized in that, its X-ray powder diffraction pattern (XRPD) is 20.8 ° ± 0.2 °, 23.8 ° ± 0.2 ° and 11.9 ° ± 0.2 ° in 2theta value and locates to have characteristic peak.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form III of acetic acid, be further characterized in that, its x-ray diffraction pattern (XRPD) is 17.8 ° ± 0.2 °, 24.0 ° ± 0.2 °, 27.2 ° ± 0.2 °, 7.9 ° ± 0.2 °, 15.3 ° ± 0.2 °, 17.4 ° ± 0.2 ° and 22.4 ° ± 0.2 ° in 2theta value and locates to have characteristic peak, as shown in Figure 1.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form III of acetic acid, it is characterized in that, its differential scanning calorimetric analysis (DSC) locates to have an endotherm(ic)peak approximately 142 ℃ of starting temperatures, as shown in Figure 2.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form III of acetic acid, it is characterized in that, its thermogravimetric analysis (TGA) is weightlessness approximately 1.1% when being heated to approach 120 ℃, as shown in Figure 3.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form III, is characterized in that, this crystal formation is without hydrate.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) preparation method of acetic acid crystalline form III, it is characterized in that, its preparation method comprises the steps: (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2 by 2-, 4-triazole-3-base sulfenyl) acetic acid powder dissolution is in acetonitrile, ethyl acetate, toluene or other organic solvent, and the method by slow volatilization under room temperature condition obtains.
On the other hand, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form IV of acetic acid, it is characterized in that, its X-ray powder diffraction pattern (XRPD) is 6.8 ° ± 0.2 °, 18.5 ° ± 0.2 ° and 24.6 ° ± 0.2 ° in 2theta value and locates to have characteristic peak.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form IV of acetic acid, be further characterized in that, its x-ray diffraction pattern (XRPD) is 24.1 ° ± 0.2 °, 25.0 ° ± 0.2 °, 26.7 ° ± 0.2 °, 11.3 ° ± 0.2 °, 19.0 ° ± 0.2 °, 21.9 ° ± 0.2 ° and 20.6 ° ± 0.2 ° in 2theta value and locates to have characteristic peak, as shown in Figure 4.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form IV of acetic acid, it is characterized in that, its differential scanning calorimetric analysis (DSC) locates to have an endotherm(ic)peak approximately 97 ℃ of starting temperatures, locates to have another endotherm(ic)peak subsequently, as shown in Figure 5 approximately 138 ℃ of starting temperatures.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form IV of acetic acid, it is characterized in that, its thermogravimetric analysis (TGA) is weightlessness approximately 12.8% when being heated to approach 110 ℃, as shown in Figure 6.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form IV, is characterized in that, this crystal formation is methylene dichloride (DCM) solvate.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) preparation method of acetic acid crystalline form IV, it is characterized in that, its preparation method comprises the steps: (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2 by 2-, 4-triazole-3-base sulfenyl) acetic acid powder dissolution is in methylene dichloride (DCM) solvent, and the method by slow volatilization under room temperature condition obtains.
On the other hand, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form V of acetic acid, it is characterized in that, in its x-ray diffraction pattern, in 2theta value, be 20.9 ° ± 0.2 °, 6.1 ° ± 0.2 ° and 26.2 ° ± 0.2 ° and locate to there is characteristic peak.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form V of acetic acid, be further characterized in that, its x-ray diffraction pattern (XRPD) is 24.8 ° ± 0.2 °, 18.7 ° ± 0.2 °, 20.1 ° ± 0.2 °, 14.6 ° ± 0.2 °, 17.2 ° ± 0.2 °, 19.4 ° ± 0.2 ° and 23.6 ° ± 0.2 ° in 2theta value and locates to have characteristic peak, as shown in Figure 7.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form V of acetic acid, it is characterized in that, its differential scanning calorimetric analysis (DSC) locates to have an endotherm(ic)peak approximately 59 ℃ of starting temperatures, locates to have another endotherm(ic)peak subsequently, as shown in Figure 8 approximately 132 ℃ of starting temperatures.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form V of acetic acid, it is characterized in that, its thermogravimetric analysis (TGA) is weightlessness approximately 11.0% when being heated to approach 135 ℃, as shown in Figure 9.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form V, is characterized in that, this crystal formation is 2-methyltetrahydrofuran (2-MeTHF) solvate.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) preparation method of acetic acid crystalline form V, it is characterized in that, its preparation method comprises the steps: (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2 by 2-, 4-triazole-3-base sulfenyl) acetic acid powder dissolution is in 2-methyltetrahydrofuran (2-MeTHF) solvent, and the method by slow volatilization under room temperature condition obtains.
On the other hand, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) the crystal formation VI of acetic acid, it is characterized in that, in its x-ray diffraction pattern, in 2theta value, be 23.5 ° ± 0.2 °, 6.6 ° ± 0.2 ° and 18.3 ° ± 0.2 ° and locate to there is characteristic peak.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) the crystal formation VI of acetic acid, be further characterized in that, its x-ray diffraction pattern (XRPD) is 17.9 ° ± 0.2 °, 21.3 ° ± 0.2 °, 27.7 ° ± 0.2 °, 11.2 ° ± 0.2 °, 23.8 ° ± 0.2 °, 25.1 ° ± 0.2 ° and 29.6 ° ± 0.2 ° in 2theta value and locates to have characteristic peak, as shown in figure 10.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) the crystal formation VI of acetic acid, it is characterized in that, its differential scanning calorimetric analysis (DSC) locates to have an endotherm(ic)peak approximately 63 ℃ of starting temperatures, locates to have another endotherm(ic)peak subsequently, as shown in figure 11 approximately 132 ℃ of starting temperatures.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) the crystal formation VI of acetic acid, it is characterized in that, its thermogravimetric analysis (TGA) is weightlessness approximately 6.4% when being heated to approach 74 ℃, as shown in figure 12.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystal formation VI, is characterized in that, this crystal formation is trichloromethane solvate.
Further, 2-provided by the invention (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) preparation method of acetic acid crystal formation VI, it is characterized in that, its preparation method comprises the steps: (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2 by 2-, 4-triazole-3-base sulfenyl) acetic acid powder dissolution is in trichloromethane solvent, and the method by slow volatilization under room temperature condition obtains.
Accompanying drawing explanation
Fig. 1 is the XRPD figure of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form III.
Fig. 2 is the DSC figure of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form III.
Fig. 3 is the TGA figure of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form III.
Fig. 4 is the XRPD figure of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form IV.
Fig. 5 is the DSC figure of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form IV.
Fig. 6 is the TGA figure of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form IV.
Fig. 7 is the XRPD figure of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form V.
Fig. 8 is the DSC figure of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form V.
Fig. 9 is the TGA figure of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form V.
Figure 10 is the XRPD figure of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystal formation VI.
Figure 11 is the DSC figure of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystal formation VI.
Figure 12 is the TGA figure of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystal formation VI.
Embodiment
Below will further set forth the present invention by specific embodiment, but be not limited to protection scope of the present invention.Those skilled in the art can make improvements preparation method and use instrument within the scope of claim, and these improvement also should be considered as protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.
In following embodiment, except as otherwise noted, described test method is implemented according to the condition of normal condition or manufacturer's suggestion conventionally; Shown raw material, reagent all can obtain by the mode of commercially available purchase.
X-ray powder diffraction pattern of the present invention gathers on Panalytical Empyrean x-ray powder diffraction instrument.The method parameter of X-ray powder diffraction of the present invention is as follows:
X-ray reflection parameter: CuKa
1.540598；
1.544426
Voltage: 45 KVs (kV)
Electric current: 40 milliampere(mA)s (mA)
Divergent slit: automatically
Scan pattern: continuously
Sweep limit: from 3.0 to 40.0 degree
Sampling step length: 0.013 degree
Every step Measuring Time: 78.795 seconds/step
Differential scanning calorimetric thermogram of the present invention gathers in TAQ2000 differential scanning calorimeter.The method parameter of differential scanning calorimetric analysis of the present invention is as follows:
Temperature range/℃: room temperature-300 ℃
Scanning speed/℃/min: 10 ℃/min
Shielding gas: nitrogen 50 ml/min
Thermogravimetric analysis figure of the present invention gathers on TAQ500 thermogravimetric analyzer.The method parameter of thermogravimetric analysis of the present invention is as follows:
Temperature range/℃: room temperature-320 ℃
Scanning speed/℃/min: 10 ℃/min
Shielding gas: nitrogen 60 ml/min
Embodiment 1:
The preparation of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form III:
By 10mg2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid powder dissolution is in 1.0mL acetonitrile solvent, filtration obtains settled solution, the sample bottle that this settled solution is housed is sealed up to the sealed membrane of pricking hole, slowly evaporate at ambient temperature solid and separate out, collect solid and obtain crystalline form III.Its X-ray powder diffraction figure (XRPD) as shown in Figure 1.
In X-ray powder diffraction pattern, in 2theta value, be 20.8 °, 23.8 °, 11.9 °, 17.8 °, 24.0 °, 27.2 °, 7.9 °, 15.3 °, 17.4 ° and 22.4 ° and locate to there is characteristic peak.
Embodiment 2:
The preparation of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form IV:
By 10mg2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid powder dissolution is in 2.0mL methylene dichloride (DCM) solvent, filtration obtains settled solution, the sample bottle that this settled solution is housed is sealed up to the sealed membrane of pricking hole, slowly evaporate at ambient temperature solid and separate out, collect solid and obtain crystalline form IV.Its X-ray powder diffraction figure (XRPD) as shown in Figure 4.
In X-ray powder diffraction pattern, in 2theta value, be 6.8 °, 18.5 °, 24.6 °, 24.1 °, 25.0 °, 26.7 °, 11.3 °, 19.0 °, 21.9 ° and 20.6 ° and locate to there is characteristic peak.
Embodiment 3:
The preparation of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystalline form V:
By 10mg2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid powder dissolution is in 0.3mL2-methyltetrahydrofuran (2-MeTHF) solvent, filtration obtains settled solution, the sample bottle that this settled solution is housed is sealed up to the sealed membrane of pricking hole, slowly evaporate at ambient temperature solid and separate out, collect solid and obtain crystalline form V.Its X-ray powder diffraction figure (XRPD) as shown in Figure 7.
In X-ray powder diffraction pattern, in 2theta value, be 20.8 °, 23.7 °, 6.2 °, 22.4 °, 24.0 °, 27.2 °, 11.9 °, 17.3 °, 24.9 ° and 26.2 ° and locate to there is characteristic peak.
Embodiment 4:
The preparation of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid crystal formation VI:
By 10mg2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid powder dissolution is in 0.4mL trichloromethane solvent, filtration obtains settled solution, the sample bottle that this settled solution is housed is sealed up to the sealed membrane of pricking hole, slowly evaporate at ambient temperature solid and separate out, collect solid and obtain crystal formation VI.Its X-ray powder diffraction figure (XRPD) as shown in figure 10.
In X-ray powder diffraction pattern, in 2theta value, be 23.5 °, 20.8 °, 6.7 °, 23.9 °, 27.2 °, 21.4 °, 11.9 °, 17.3 °, 18.3 ° and 25.2 ° and locate to there is characteristic peak.
Claims (19)
1. 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form III of acetic acid, it is characterized in that, in its x-ray diffraction pattern, in 2theta value, be 20.8 ° ± 0.2 °, 23.8 ° ± 0.2 °, 11.9 ° ± 0.2 °, 17.8 ° ± 0.2 °, 24.0 ° ± 0.2 °, 27.2 ° ± 0.2 °, 7.9 ° ± 0.2 °, 15.3 ° ± 0.2 °, 17.4 ° ± 0.2 ° and 22.4 ° ± 0.2 ° and locate to there is characteristic peak.
2. crystalline form III according to claim 1, is characterized in that, figure is substantially consistent with Fig. 1 for its X-ray diffraction (XRPD).
3. crystalline form III according to claim 1, is characterized in that the means of differential scanning calorimetry shown in Fig. 2 (DSC) curve.
4. crystalline form III according to claim 1, is characterized in that the thermogravimetric analysis shown in Fig. 3 (TGA) curve.
5. 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form IV of acetic acid, it is characterized in that, in its x-ray diffraction pattern, in 2theta value, be 6.8 ° ± 0.2 °, 18.5 ° ± 0.2 °, 24.6 ° ± 0.2 °, 24.1 ° ± 0.2 °, 25.0 ° ± 0.2 °, 26.7 ° ± 0.2 °, 11.3 ° ± 0.2 °, 19.0 ° ± 0.2 °, 21.9 ° ± 0.2 ° and 20.6 ° ± 0.2 ° and locate to there is characteristic peak.
6. crystalline form IV according to claim 5, is characterized in that, figure is substantially consistent with Fig. 4 for its X-ray diffraction (XRPD).
7. crystalline form IV according to claim 5, is characterized in that the means of differential scanning calorimetry shown in Fig. 5 (DSC) curve.
8. crystalline form IV according to claim 5, is characterized in that the thermogravimetric analysis shown in Fig. 6 (TGA) curve.
9. crystalline form IV according to claim 5, is characterized in that, this crystal formation is methylene dichloride (DCM) solvate.
10. 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) crystalline form V of acetic acid, it is characterized in that, in its x-ray diffraction pattern, in 2theta value, be 20.9 ° ± 0.2 °, 6.1 ° ± 0.2 °, 26.2 ° ± 0.2 °, 24.8 ° ± 0.2 °, 18.7 ° ± 0.2 °, 20.1 ° ± 0.2 °, 14.6 ° ± 0.2 °, 17.2 ° ± 0.2 °, 19.4 ° ± 0.2 ° and 23.6 ° ± 0.2 ° and locate to there is characteristic peak.
11. crystalline form Vs according to claim 10, is characterized in that, figure is substantially consistent with Fig. 7 for its X-ray diffraction (XRPD).
12. crystalline form Vs according to claim 10, is characterized in that the means of differential scanning calorimetry shown in Fig. 8 (DSC) curve.
13. crystalline form Vs according to claim 10, is characterized in that the thermogravimetric analysis shown in Fig. 9 (TGA) curve.
14. crystalline form Vs according to claim 10, is characterized in that, this crystal formation is 2-methyltetrahydrofuran (2-MeTHF) solvate.
15. 1 kinds of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) the crystal formation VI of acetic acid, it is characterized in that, in its x-ray diffraction pattern, in 2theta value, be 23.5 ° ± 0.2 °, 6.6 ° ± 0.2 °, 18.3 ° ± 0.2 °, 17.9 ° ± 0.2 °, 21.3 ° ± 0.2 °, 27.7 ° ± 0.2 °, 11.2 ° ± 0.2 °, 23.8 ° ± 0.2 °, 25.1 ° ± 0.2 ° and 29.6 ° ± 0.2 ° and locate to there is characteristic peak.
16. crystal formation VI according to claim 15, is characterized in that, figure is substantially consistent with Figure 10 for its X-ray diffraction (XRPD).
17. crystal formation VI according to claim 15, is characterized in that the means of differential scanning calorimetry shown in Figure 11 (DSC) curve.
18. crystal formation VI according to claim 15, is characterized in that the thermogravimetric analysis shown in Figure 12 (TGA) curve.
19. crystal formation VI according to claim 15, is characterized in that, this crystal formation is trichloromethane solvate.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310597329.6A CN103588716A (en) | 2013-11-22 | 2013-11-22 | Novel crystal form of 2-(5-bromine-4-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-ylsulfenyl) acetic acid and preparation method thereof |
| CN201410660068.2A CN104447590B (en) | 2013-11-22 | 2014-11-19 | Crystal formation of 2 (the base sulfenyl of 5 bromine 4 (base of 4 cyclopropyl naphthalene 1) 1,2,4 triazoles of 4H 3) acetic acid and preparation method thereof |
| US15/038,470 US10351536B2 (en) | 2013-11-22 | 2014-11-20 | Crystalline forms of lesinurad and its sodium salt |
| EP14863925.5A EP3071554B1 (en) | 2013-11-22 | 2014-11-20 | Crystalline forms of lesinurad |
| ES14863925T ES2704198T3 (en) | 2013-11-22 | 2014-11-20 | Crystal forms of lesinurad |
| PCT/IB2014/003077 WO2015075561A2 (en) | 2013-11-22 | 2014-11-20 | Crystalline forms of lesinurad and its sodium salt |
| JP2016554929A JP6470761B2 (en) | 2013-11-22 | 2014-11-20 | Crystalline form of Resinurad and its sodium salt |
| AU2014351486A AU2014351486C1 (en) | 2013-11-22 | 2014-11-20 | Crystalline forms of lesinurad and its sodium salt |
| CA2931430A CA2931430A1 (en) | 2013-11-22 | 2014-11-20 | Crystalline forms of lesinurad and its sodium salt |
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| CN201310597329.6A CN103588716A (en) | 2013-11-22 | 2013-11-22 | Novel crystal form of 2-(5-bromine-4-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-ylsulfenyl) acetic acid and preparation method thereof |
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| CN201410660068.2A Expired - Fee Related CN104447590B (en) | 2013-11-22 | 2014-11-19 | Crystal formation of 2 (the base sulfenyl of 5 bromine 4 (base of 4 cyclopropyl naphthalene 1) 1,2,4 triazoles of 4H 3) acetic acid and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015075561A3 (en) * | 2013-11-22 | 2015-09-11 | Crystal Pharmatech Co., Ltd. | Crystalline forms of lesinurad and its sodium salt |
| CN107298657A (en) * | 2016-04-15 | 2017-10-27 | 浙江京新药业股份有限公司 | The crystal formation II of 2- (the bromo- 4- of 5- (4- cyclopropyl naphthalene -1- bases) -4H-1,2,4- triazole -3- bases sulfenyl) acetic acid axial chirality enantiomer |
| CN107337649A (en) * | 2016-04-29 | 2017-11-10 | 四川科伦药物研究院有限公司 | A kind of acetic acid sodium hydrate is unformed and its production and use |
| WO2019001325A1 (en) * | 2017-06-28 | 2019-01-03 | 苏州科睿思制药有限公司 | Crystal form xv of lesinurad and preparation method therefor |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111153862B (en) * | 2020-01-19 | 2021-07-06 | 北京鑫开元医药科技有限公司海南分公司 | Raisinard refining method |
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| US20100056464A1 (en) * | 2008-09-04 | 2010-03-04 | Ardea Biosciences | Compounds, compositions and methods of using same for modulating uric acid levels |
| WO2010028190A2 (en) * | 2008-09-04 | 2010-03-11 | Ardea Biosciences, Inc. | Compounds, compositions and methods of using same for modulating uric acid levels |
| CN102741234A (en) * | 2010-01-08 | 2012-10-17 | 亚德生化公司 | Polymorphic, crystalline and mesophase forms of sodium 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-ylthio)acetate, and uses thereof |
| CN103298796A (en) * | 2010-12-30 | 2013-09-11 | 阿迪亚生命科学公司 | Polymorphic forms of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio) acetic acid and uses thereof |
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| AR069753A1 (en) * | 2007-11-27 | 2010-02-17 | Ardea Biosciences Inc | 1,2,4-TRIAZOL COMPOUNDS AND COMPOSITIONS, USEFUL IN THE MODULATION OF SANGUINEO URIC ACID LEVELS |
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- 2013-11-22 CN CN201310597329.6A patent/CN103588716A/en active Pending
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100056464A1 (en) * | 2008-09-04 | 2010-03-04 | Ardea Biosciences | Compounds, compositions and methods of using same for modulating uric acid levels |
| WO2010028190A2 (en) * | 2008-09-04 | 2010-03-11 | Ardea Biosciences, Inc. | Compounds, compositions and methods of using same for modulating uric acid levels |
| CN102741234A (en) * | 2010-01-08 | 2012-10-17 | 亚德生化公司 | Polymorphic, crystalline and mesophase forms of sodium 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-ylthio)acetate, and uses thereof |
| CN103298796A (en) * | 2010-12-30 | 2013-09-11 | 阿迪亚生命科学公司 | Polymorphic forms of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio) acetic acid and uses thereof |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015075561A3 (en) * | 2013-11-22 | 2015-09-11 | Crystal Pharmatech Co., Ltd. | Crystalline forms of lesinurad and its sodium salt |
| CN107298657A (en) * | 2016-04-15 | 2017-10-27 | 浙江京新药业股份有限公司 | The crystal formation II of 2- (the bromo- 4- of 5- (4- cyclopropyl naphthalene -1- bases) -4H-1,2,4- triazole -3- bases sulfenyl) acetic acid axial chirality enantiomer |
| CN107337649A (en) * | 2016-04-29 | 2017-11-10 | 四川科伦药物研究院有限公司 | A kind of acetic acid sodium hydrate is unformed and its production and use |
| WO2019001325A1 (en) * | 2017-06-28 | 2019-01-03 | 苏州科睿思制药有限公司 | Crystal form xv of lesinurad and preparation method therefor |
Also Published As
| Publication number | Publication date |
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| CN104447590B (en) | 2017-11-28 |
| CN104447590A (en) | 2015-03-25 |
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