Methods of treating diabetes
View Patent ↗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.
1. A method of treating diabetes in a patient, which comprises administering to a patient in need thereof a therapeutically effective amount of crystalline 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. A method of treating diabetes in a patient, which comprises administering to a patient in need thereof a therapeutically effective amount of 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.
3. The method of claim 2 , wherein the X-ray powder diffraction pattern contains a peak at about 14.0 degrees 2θ.
4. The method of claim 2 , wherein the X-ray powder diffraction pattern is substantially the same as that shown in FIG. 1 .
5. The method of claim 1 , wherein the crystalline anhydrous (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol 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 method of claim 5 , wherein the Raman spectrum is substantially the same as that shown in FIG. 2 .
7. A method of treating diabetes in a patient, which comprises administering to a patient in need thereof a therapeutically effective amount of crystalline 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. A method of treating diabetes in a patient, which comprises administering to a patient in need thereof a therapeutically effective amount of 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 4.4, 4.8, 14.5, 14.7, 15.5, 21.2, 22.1 and/or 23.8 degrees 2θ.
9. The method of claim 8 , wherein the X-ray powder diffraction pattern has a peak at about 4.4 degrees 2θ.
10. The method of claim 8 , wherein the X-ray powder diffraction pattern is substantially the same as that shown in FIG. 3 .
11. The method of claim 7 , wherein the crystalline anhydrous (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol 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 method of claim 11 , wherein the Raman spectrum is substantially the same as that shown in FIG. 4 .
13. The method of claim 1 , wherein the diabetes is Type 1 diabetes.
14. The method of claim 2 , wherein the diabetes is Type 1 diabetes.
15. The method of claim 7 , wherein the diabetes is Type 1 diabetes.
16. The method of claim 8 , wherein the diabetes is Type 1 diabetes.