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Last Updated: March 29, 2025

Claims for Patent: 8,217,156


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Summary for Patent: 8,217,156
Title:Solid forms of (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol and methods of their use
Abstract:Solid forms of anhydrous (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol are disclosed, in addition to methods of their use in the treatment of various diseases and disorders.
Inventor(s):Susan Margaret De Paul, Anett Perlberg, Matthew Mangzhu Zhao
Assignee:Solvias AG, Lexicon Pharmaceuticals Inc
Application Number:US12/503,225
Patent Claims: 1. A crystalline compound, which is anhydrous (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol having a DSC endotherm at about 124° C.

2. The crystalline compound of claim 1, which has an X-ray powder diffraction pattern with peaks at one or more of about 4.0, 8.1, 9.8, 14.0 and/or 19.3 degrees 2Θ.

3. The crystalline compound of claim 2, which has an X-ray powder diffraction pattern with a peak at about 14.0 degrees 2Θ.

4. The crystalline compound of claim 1, which has an X-ray powder diffraction pattern that is substantially the same as that shown in FIG. 1.

5. The crystalline compound of claim 1, which has a Raman spectrum with peaks at one or more of about 3068, 2929, 2888, 2881, 1615, 1603, 1244, 1037, 692 and/or 372 cm−1.

6. The crystalline compound of claim 1, which has a Raman spectrum that is substantially the same as that shown in FIG. 2.

7. A crystalline compound, which is anhydrous (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol having a DSC endotherm at about 134° C.

8. The crystalline compound of claim 2, which has an X-ray powder diffraction pattern with peaks at one or more of about 4.4, 4.8, 14.5, 14.7, 15.5, 21.2, 22.1 and/or 23.8 degrees 2Θ.

9. The crystalline compound of claim 8, which has an X-ray powder diffraction pattern with a peak at about 4.4 degrees 2Θ.

10. The crystalline compound of claim 2, which has an X-ray powder diffraction pattern that is substantially the same as that shown in FIG. 3.

11. The crystalline compound of claim 2, which has a Raman spectrum with peaks at one or more of about 3061, 2927, 2877, 2864, 1605, 1038, 842, and/or 719 cm−1.

12. The crystalline compound of claim 2, which has a Raman spectrum that is substantially the same as that shown in FIG. 4.

13. A pharmaceutical dosage form comprising an active pharmaceutical ingredient and a pharmaceutically acceptable excipient or diluent, wherein the active pharmaceutical ingredient is crystalline anhydrous (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol having an X-ray powder diffraction pattern with peaks at one or more of about 4.0, 8.1, 9.8, 14.0 and/or 19.3 degrees 2Θ.

14. A pharmaceutical dosage form comprising an active pharmaceutical ingredient and a pharmaceutically acceptable excipient or diluent wherein the active pharmaceutical ingredient is crystalline anhydrous (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol having an X-ray powder diffraction pattern having peaks at one or more of about 4.4, 4.8, 14.5, 14.7, 15.5, 21.2, 22.1 and/or 23.8 degrees 2Θ.

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