Crystalline forms of [3-(4- {2-butyl-1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl} -phenoxy)-propyl]-diethyl-amine
The present invention relates to crystalline forms of [3-(4-{2-butyl-1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethylamine (“COMPOUND I”) useful in the treatment of RAGE mediated diseases.
1. A solid state form of [3-(4-{2-butyl-1-[4-(4-chlorophenoxy)phenyl]-1H-imidazol-4-yl}phenoxy)-propyl]-diethylamine, wherein the solid state form is crystalline and is characterized by an X-ray Powder Diffraction (XRPD) pattern having peaks at 2θ angles of 5.4°±0.2°, 21.5°±0.2°, and 22.0°±0.2°.
2. The solid state form of claim 1 , characterized by an XRPD pattern as shown in FIG. 1 .
3. The solid state form of claim 2 , characterized by an endothermic peak at about 59° C., as determined by Differential Scanning Calorimetry (DSC).
4. The solid state form of claim 2 , characterized by a Differential Scanning Calorimetry (DSC) profile as shown in FIG. 2 .
5. The solid state form of claim 2 , characterized by an about 2.3 wt % loss between room temperature and about 150° C., as determined by Thermogravimetry Analysis (TGA).
6. The solid state form of claim 2 , characterized by a Thermogravimetry Analysis (TGA) profile as shown in FIG. 2 .
7. The solid state form of claim 1 , characterized by the following features:
i) an XRPD pattern having peaks at 2θ angles of 5.4°±0.2°, 21.5°±0.2°, and 22.0°±0.2°;
ii) a Differential Scanning Calorimetry (DSC) profile as shown in FIG. 2 ; and
iii) a Thermogravimetry Analysis (TGA) profile as shown in FIG. 2 .
8. A solid state form of [3-(4-{2-butyl-1-[4-(4-chlorophenoxy)phenyl]-1H-imidazol-4-yl}phenoxy)-propyl]-diethylamine, wherein the solid state form is crystalline and is characterized by an X-ray Powder Diffraction (XRPD) pattern having peaks at 2θ angles of 19.7°±0.2°, 22.0°±0.2°, and 30.2°±0.2°.
9. The solid state form of claim 8 , characterized by an XRPD pattern having peaks at 2θ angles of 5.4°±0.2°, 19.7°±0.2°, 21.8°±0.2°, 22.0°±0.2°, and 30.2°±0.2°.
10. The solid state form of claim 8 , characterized by an XRPD pattern as shown in FIG. 3 .
11. The solid state form of claim 8 , characterized by an endothermic peak at about 51.9° C., as determined by Differential Scanning Calorimetry (DSC).
12. The solid state form of claim 8 , characterized by a Differential Scanning Calorimetry (DSC) profile as shown in FIG. 4 .
13. The solid state form of claim 8 , characterized by an about 4.2 wt % loss between room temperature and about 150° C., as determined by Thermogravimetry Analysis (TGA).
14. The solid state form of claim 8 , characterized by a TGA profile as shown in FIG. 4 .
15. The solid state form of claim 8 , characterized by the following features:
i) an XRPD pattern having peaks at 2θ angles of 19.7°±0.2°, 22 . 0 °± 0 . 2 °, and 30.2°±0.2°;
ii) a Differential Scanning Calorimetry (DSC) profile as shown in FIG. 4 ; and
iii) a TGA profile as shown in FIG. 4 .
16. A pharmaceutical composition comprising the solid state form of claim 1 and one or more pharmaceutically acceptable carriers or diluents.
17. A pharmaceutical composition comprising the solid state form of claim 8 and one or more pharmaceutically acceptable carriers or diluents.