CN103626710A - Cocrystals of 2-(5-bromo-4-(4-cyclopropylnaphthalene-1-yl)-4H-1, 2, 4-triazol-3-ylthio) acetic acid and preparation method thereof - Google Patents

Cocrystals of 2-(5-bromo-4-(4-cyclopropylnaphthalene-1-yl)-4H-1, 2, 4-triazol-3-ylthio) acetic acid and preparation method thereof Download PDF

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CN103626710A
CN103626710A CN201310706091.6A CN201310706091A CN103626710A CN 103626710 A CN103626710 A CN 103626710A CN 201310706091 A CN201310706091 A CN 201310706091A CN 103626710 A CN103626710 A CN 103626710A
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bromo
acetic acid
triazole
cocrystallizing type
base sulfenyl
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陈敏华
张炎锋
杨朝惠
张晓宇
王鹏
李丕旭
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SUZHOU PENGXU PHARMATECH Co Ltd
Crystal Pharmatech Co Ltd
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SUZHOU PENGXU PHARMATECH Co Ltd
Crystal Pharmatech Co Ltd
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Publication of CN103626710A publication Critical patent/CN103626710A/en
Priority to CN201710052927.3A priority patent/CN106866559B/en
Priority to CN201410783346.3A priority patent/CN104529919B/en
Priority to PCT/US2014/071501 priority patent/WO2015095703A1/en
Priority to US15/106,361 priority patent/US9969701B2/en
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
    • C07C59/06—Glycolic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Abstract

The invention relates to two cocrystal forms of a compound, namely 2-(5-bromo-4-(4-cyclopropylnaphthalene-1-yl)-4H-1, 2, 4-triazol-3-ylthio) acetic acid and respectively relates to a cocrystal form A of 2-(5-bromo-4-(4-cyclopropylnaphthalene-1-yl)-4H-1, 2, 4-triazol-3-ylthio) acetic acid-proline and a cocrystal form B of 2-(5-bromo-4-(4-cyclopropylnaphthalene-1-yl)-4H-1, 2, 4-triazol-3-ylthio) acetic acid-glycolic acid.

Description

Eutectic 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
Affiliated technical field
The present invention relates to chemical field of medicaments, particularly relate to eutectic 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 (Lesinurad) 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:
Figure BDA0000442385520000011
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 discloses 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) cocrystallizing type of the cocrystallizing type of acetic acid-proline(Pro) and 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid-oxyacetic acid.
On the one hand, the invention discloses the cocrystallizing type of a kind of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid-proline(Pro), called after cocrystallizing type A in the present invention.
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 cocrystallizing type A of acetic acid-proline(Pro), it is characterized in that, in its X-ray diffractogram, in 2theta value, be 21.9 ° ± 0.2 °, 18.1 ° ± 0.2 ° and 20.2 ° ± 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) the cocrystallizing type A of acetic acid-proline(Pro), be further characterized in that, in its X-ray diffractogram, in 2theta value, be 12.6 ° ± 0.2 °, 13.1 ° ± 0.2 °, 14.8 ° ± 0.2 °, 18.9 ° ± 0.2 °, 19.8 ° ± 0.2 °, 20.5 ° ± 0.2 °, 24.8 ° ± 0.2 ° and locate to there is 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) the cocrystallizing type A of acetic acid-proline(Pro), it is characterized in that, its differential scanning calorimetric analysis (DSC) 58.1 ℃, 66.2 ℃, near there is respectively endotherm(ic)peak, near 152.6 ℃ of starting temperatures, start to occur another endotherm(ic)peak, 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) the cocrystallizing type A of acetic acid-proline(Pro), it is characterized in that, weightlessness approximately 2.8% when it is heated to approach 85.0 ℃, its thermogravimetric analysis figure is as shown in Figure 3.
The invention provides a kind of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) preparation method of acetic acid-proline(Pro) eutectic, it is characterized in that, its preparation method comprises the steps: (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1 by 2-, 2,4-triazole-3-base sulfenyl) acetic acid (Lesinurad) powder dissolution is in organic solvent, by mol ratio 2:1(proline(Pro)/Lesinurad) proline(Pro) add in this solution, under room temperature condition, stir, the centrifugal solid obtaining is this cocrystallizing type.
On the other hand, the invention discloses the cocrystallizing type of a kind of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid-oxyacetic acid, called after cocrystallizing type B in the present invention.
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 cocrystallizing type B of acetic acid-oxyacetic acid, it is characterized in that, in its X-ray diffractogram, in 2theta value, be 21.3 ° ± 0.2 °, 20.9 ° ± 0.2 ° and 17.9 ° ± 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 cocrystallizing type B of acetic acid-oxyacetic acid, be further characterized in that, in its X-ray diffractogram, in 2theta value, be 10.9 ° ± 0.2 °, 11.4 ° ± 0.2 °, 13.0 ° ± 0.2 °, 17.4 ° ± 0.2 °, 24.3 ° ± 0.2 °, 25.4 ° ± 0.2 °, 27.3 ° ± 0.2 ° and locate to there is 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) the cocrystallizing type B of acetic acid-oxyacetic acid, it is characterized in that, its differential scanning calorimetric analysis (DSC) starts respectively to occur endotherm(ic)peak near 52.8 ℃, 111.3 ℃, as shown in Figure 5.
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 cocrystallizing type B of acetic acid-oxyacetic acid, it is characterized in that, weightlessness approximately 10.0% when it is heated to approach 135.0 ℃, its thermogravimetric analysis figure is as shown in Figure 6.
The invention provides a kind of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) preparation method of the cocrystallizing type of acetic acid-oxyacetic acid, it is characterized in that, its preparation method comprises the steps: (the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1 by 2-, 2,4-triazole-3-base sulfenyl) acetic acid (Lesinurad) powder dissolution is in the mixed solvent of organic solvent or organic solvent and water, by mol ratio 1:1(oxyacetic acid/Lesinurad) oxyacetic acid add in this solution, under room temperature condition, slowly volatilization obtains this cocrystallizing type.
Accompanying drawing explanation
Fig. 1 is the XRPD figure of the cocrystallizing type A of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid and proline(Pro).
Fig. 2 is the DSC figure of the cocrystallizing type A of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid and proline(Pro).
Fig. 3 is the TGA figure of the cocrystallizing type A of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid and proline(Pro).
Fig. 4 is the XRPD figure of the cocrystallizing type B of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid and oxyacetic acid.
Fig. 5 is the DSC figure of the cocrystallizing type B of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid and oxyacetic acid.
Fig. 6 is the TGA figure of the cocrystallizing type B of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid and oxyacetic acid.
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 figure 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
Kα1
Figure BDA0000442385520000051
：1.540598；Kα2
Figure BDA0000442385520000052
：1.544426
K α 2/K α 1 intensity: 0.50
Voltage: 45 KVs (kV)
Electric current: 40 milliampere(mA)s (mA)
Divergent slit: automatically
Scan pattern: continuously
Scan scope: 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 the cocrystallizing type A of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid-proline(Pro):
By 151.2mg2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid (Lesinurad) powder dissolution is in 1.0mL ethyl acetate solvent, 84.8mg proline(Pro) is added in this solution, under room temperature condition, stir 24 hours, the centrifugal solid obtaining is this crystal formation.
Described 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) the cocrystallizing type A of acetic acid-proline(Pro), its X-ray powder diffraction figure (XRPD) as shown in Figure 4, it is characterized in that, in 2theta value, be 21.9 °, 18.1 °, 20.2 °, 12.6 °, 13.1 °, 14.8 °, 18.9 °, 19.8 °, 20.5 °, 24.8 ° and locate to there is characteristic peak.
Embodiment 2:
The preparation of the cocrystallizing type B of 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid-oxyacetic acid:
By 10mg2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid (Lesinurad) powder dissolution is in 0.3mL methyl alcohol, again 1.9mg oxyacetic acid is added in this solution, obtain settled solution, slowly evaporate at ambient temperature solvent and volatilize, can obtain the cocrystallizing type of oxyacetic acid.
Described 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) the cocrystallizing type B of acetic acid-oxyacetic acid, its X-ray powder diffraction figure (XRPD) as shown in Figure 4, it is characterized in that, in 2theta value, be 21.3 °, 20.9 °, 17.9 °, 10.9 °, 11.4 °, 13.0 °, 17.4 °, 24.3 °, 25.4 °, 27.3 ° and locate to there is characteristic peak.

Claims (8)

1. 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) the cocrystallizing type A of acetic acid (Lesinurad) and proline(Pro), it is characterized in that, in its X-ray diffractogram, in 2theta value, be 21.9 ° ± 0.2 °, 18.1 ° ± 0.2 ° and 20.2 ° ± 0.2 ° and locate to there is characteristic peak.
2. cocrystallizing type A according to claim 1, be further characterized in that, in its X-ray diffractogram, in 2theta value, be 12.6 ° ± 0.2 °, 13.1 ° ± 0.2 °, 14.8 ° ± 0.2 °, 18.9 ° ± 0.2 °, 19.8 ° ± 0.2 °, 20.5 ° ± 0.2 °, 24.8 ° ± 0.2 ° and locate to there is characteristic peak.
3. cocrystallizing type A according to claim 1, is characterized in that, figure is substantially consistent with Fig. 1 for its X-ray diffraction (XRPD).
4. cocrystallizing type A according to claim 1, it is characterized in that, its preparation method is by 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid (Lesinurad) powder dissolution is in organic solvent, by mol ratio 2:1(proline(Pro)/Lesinurad) proline(Pro) add in this solution, under room temperature condition, stir, the centrifugal solid obtaining is this cocrystallizing type.
5. 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) the cocrystallizing type B of acetic acid and oxyacetic acid, it is characterized in that, in its X-ray diffractogram, in 2theta value, be 21.3 ° ± 0.2 °, 20.9 ° ± 0.2 ° and 17.9 ° ± 0.2 ° and locate to there is characteristic peak.
6. cocrystallizing type B according to claim 5, be further characterized in that, in its X-ray diffractogram, in 2theta value, be 10.9 ° ± 0.2 °, 11.4 ° ± 0.2 °, 13.0 ° ± 0.2 °, 17.4 ° ± 0.2 °, 24.3 ° ± 0.2 °, 25.4 ° ± 0.2 °, 27.3 ° ± 0.2 ° and locate to there is characteristic peak.
7. cocrystallizing type B according to claim 5, is characterized in that, figure is substantially consistent with Fig. 4 for its X-ray diffraction (XRPD).
8. cocrystallizing type B according to claim 5, it is characterized in that, its preparation method is by 2-(the bromo-4-of 5-(4-cyclopropyl naphthalene-1-yl)-4H-1,2,4-triazole-3-base sulfenyl) acetic acid (Lesinurad) powder dissolution is in the mixed solvent of organic solvent or organic solvent and water, by mol ratio 1:1(oxyacetic acid/Lesinurad) oxyacetic acid add in this solution, slowly volatilization obtains this cocrystallizing type at ambient temperature.
CN201310706091.6A 2013-12-20 2013-12-20 Cocrystals of 2-(5-bromo-4-(4-cyclopropylnaphthalene-1-yl)-4H-1, 2, 4-triazol-3-ylthio) acetic acid and preparation method thereof Pending CN103626710A (en)

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CN201710052927.3A CN106866559B (en) 2013-12-20 2014-12-17 Eutectic of Lei Xina get and preparation method thereof
CN201410783346.3A CN104529919B (en) 2013-12-20 2014-12-17 Eutectic 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
PCT/US2014/071501 WO2015095703A1 (en) 2013-12-20 2014-12-19 Novel salts and co-crystals of lesinurad
US15/106,361 US9969701B2 (en) 2013-12-20 2014-12-19 Salts and co-crystals of lesinurad

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104557748A (en) * 2014-01-25 2015-04-29 广东东阳光药业有限公司 Novel solid form of sulpho-1,2,4-triazole derivative
WO2016000568A1 (en) * 2014-07-02 2016-01-07 成都海创药业有限公司 Compound for treating gout

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN115838343A (en) * 2022-11-22 2023-03-24 天津大学 belinostat-L-proline zwitter-ion eutectic and preparation method and application thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI370818B (en) * 2006-04-05 2012-08-21 Astellas Pharma Inc Cocrystal of c-glycoside derivative and l-proline
TWI415840B (en) * 2007-11-27 2013-11-21 Ardea Biosciences Inc Novel compounds and compositions and methods of use
EP2123626A1 (en) * 2008-05-21 2009-11-25 Laboratorios del Dr. Esteve S.A. Co-crystals of duloxetine and co-crystal formers for the treatment of pain

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
王义成等: ""药物共晶的最新研究进展"", 《药学进展》 *
高缘等: ""药物共晶研究进展"", 《化学进展》 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104557748A (en) * 2014-01-25 2015-04-29 广东东阳光药业有限公司 Novel solid form of sulpho-1,2,4-triazole derivative
WO2016000568A1 (en) * 2014-07-02 2016-01-07 成都海创药业有限公司 Compound for treating gout
CN105294585A (en) * 2014-07-02 2016-02-03 成都海创药业有限公司 Compound for treating gout
CN105294585B (en) * 2014-07-02 2019-02-12 成都海创药业有限公司 A kind of compound for treating gout

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