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Claims for Patent: 8,546,436

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Claims for Patent: 8,546,436

Title:Polymorphic forms of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)ace- tic acid and uses thereof
Abstract: Crystalline polymorph forms of 2-(5-bromo-4-(4-cyclopropyl naphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid are described. Pharmaceutical compositions and the uses of such compounds, compound forms, and compositions for the treatment of a variety of diseases and conditions are also presented.
Inventor(s): Treiber; Laszlo R. (San Diego, CA), Galvin; Gabriel (San Diego, CA), Zamansky; Irina (Oceanside, CA), Girardet; Jean-Luc (San Diego, CA)
Assignee: Ardea Biosciences, Inc. (San Diego, CA)
Application Number:13/339,283
Patent Claims: 1. A crystalline polymorph of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)ace- tic acid: ##STR00009## characterized by peaks at 10.32, 18.84 and 20.75.degree.2.theta..+-.0.1.degree.2.theta..

2. A crystalline polymorph of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)ace- tic acid: ##STR00010## characterized by peaks at 10.46, 18.76, and 19.83.degree.2.theta..+-.0.1.degree.2.theta..

3. The crystalline polymorph of claim 2, further characterized by at least one further peak at 18.21 or 23.08.degree.2.theta..+-.0.1.degree.2.theta..

4. The crystalline polymorph of claim 2 that exhibits an x-ray powder diffraction pattern substantially the same as the x-ray powder diffraction pattern shown in FIG. 5.

5. A crystalline polymorphic form of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)ace- tic acid of claim 2 prepared by a method comprising the step of crystallizing 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)ace- tic acid from a mixture of water and ethyl acetate.

6. A solid pharmaceutical composition comprising: an effective amount of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)ace- tic acid, the 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)ace- tic acid comprising the crystalline polymorph of claim 2 as an active ingredient; and at least one excipient or carrier.

7. A process for the preparation of a crystalline polymorph of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4,-triazol-3-ylthio)ac- etic acid, the process comprising: dissolving sodium 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)ace- tate in water resulting in a solution; adding a mineral acid; adding ethylacetate; separating an organic layer; precipitating the crystalline polymorph from the organic layer; wherein the crystalline polymorph is characterized by peaks at 10.46, 18.76, and 19.83.degree.2.theta..+-.0.1.degree.2.theta..

8. The process of claim 7, wherein the process in characterized by one or more of the following: the mineral acid comprises hydrobromic acid; the mineral acid is added at about 1.05 equivalents; the volume of the organic layer is reduced to precipitate the crystalline polymorph; the organic layer is cooled to precipitate the crystalline polymorph; the crystalline polymorph is filtered and washed; and/or the crystalline polymorph is further characterized by at least one further peak at 18.21 or 23.08.degree.2.theta..+-.0.1.degree.2.theta..

9. A process for the preparation of a crystalline polymorph of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4,-triazol-3-ylthio)ac- etic acid of claim 2, comprising: (a) contacting sodium 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)ace- tate with aqueous hydrogen bromide solution and an organic solvent to form an aqueous phase and an organic phase; (b) isolating the organic phase from the mixture of step (a); and (c) crystallizing 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)ace- tic acid from the organic phase.

10. A process for the preparation of a crystalline polymorph of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4,-triazol-3-ylthio)ac- etic acid of claim 2, comprising crystallizing 2-(5-bromo-4-(4-cyclopropyl naphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid from a mixture of water and ethyl acetate.

11. A solid pharmaceutical composition comprising: 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4,-triazol-3-ylthio)ac- etic acid form 1 of claim 1 as an active ingredient; and 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4,-triazol-3-ylthio)ac- etic acid form 2 of claim 2 as an active ingredient; and at least one excipient or carrier.
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