Solid forms of a toll-like receptor modulator
The present invention provides crystalline forms, solvates and hydrates of 4-amino-2-butoxy-8-(3-(pyrrolidin-1-ylmethyl)benzyl)-7,8-dihydropteridin-6(5H)-one, and methods of making.
1. A crystalline form of Compound I having the structure:
characterized by an XRPD pattern comprising three peaks at 5.8, 11.4, 11.6, 17.7, 20.1, 20.9, 22.3, 23.9, 26.0 or 26.8 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using CuK α1 radiation.
2. The crystalline form of claim 1 , characterized by an X-ray powder diffraction (XRPD) pattern further comprising four peaks at 5.8, 11.4, 11.6, 17.7, 20.1, 20.9, 22.3, 23.9, 26.0 or 26.8 degrees 2θ (±0.2 degrees 2θ) wherein the XRPD is made using CuK α1 radiation.
3. The crystalline form of claim 1 , characterized by an XRPD pattern comprising peaks at 5.8, 11.4, 11.6, 17.7, 20.1, 20.9, 22.3, 23.9, 26.0 and 26.8 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using CuK α1 radiation.
4. The crystalline form of claim 1 , characterized by the XRPD pattern substantially in accordance with that of FIG. 1 .
5. The crystalline form of claim 1 , characterized by one or more differential scanning calorimetry (DSC) endotherms at about 133° C. or about 170° C.
6. The crystalline form of any of claim 1 , characterized by DSC endotherms at about 133° C. and about 170° C.
7. A method of preparing the crystalline form of Compound I of claim 1 , comprising:
forming a mixture comprising Compound I, and a solvent comprising a C 1 -C 3 alcohol and dichloromethane, and evaporating the solvent, thereby forming the crystalline form of Compound I of claim 1 .
8. The method of claim 7 , wherein the solvent comprises one of methanol, ethanol, or isopropanol.
9. The method of claim 7 , wherein the solvent comprises methanol and dichloromethane.
10. A pharmaceutical composition comprising a therapeutically effective amount of the crystalline form of Compound I of claim 1 , and a pharmaceutically acceptable carrier or excipient.
11. The crystalline form of claim 1 , characterized by an X-ray powder diffraction (XRPD) pattern comprising five peaks at 5.8, 11.4, 11.6, 17.7, 20.1, 20.9, 22.3, 23.9, 26.0 or 26.8 degrees 2θ (±0.2 degrees 2θ) wherein the XRPD is made using CuK α1 radiation.
12. The crystalline form of claim 1 , characterized by an X-ray powder diffraction (XRPD) pattern comprising six peaks at 5.8, 11.4, 11.6, 17.7, 20.1, 20.9, 22.3, 23.9, 26.0 or 26.8 degrees 2θ (±0.2 degrees 2θ) wherein the XRPD is made using CuK α1 radiation.
13. A crystalline form of Compound I having the structure:
characterized by an XRPD pattern comprising peaks at 5.8, 11.6 and 22.3 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using CuK α1 radiation.
14. The crystalline form of claim 13 , characterized by an X-ray powder diffraction (XRPD) pattern further comprising an additional peak at 17.7, 23.9 or 26.0 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using CuK α1 radiation.
15. The crystalline form of claim 13 , characterized by an X-ray powder diffraction (XRPD) pattern further comprising two additional peaks at 17.7, 23.9 or 26.0 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using CuK α1 radiation.
16. The crystalline form of claim 13 , characterized by an XRPD pattern comprising peaks at 5.8, 11.6, 17.7, 20.1, 20.9, 22.3, 23.9, 26.0 and 26.8 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using CuK α1 radiation.
17. A pharmaceutical composition comprising a therapeutically effective amount of the crystalline form of Compound I of claim 13 , and a pharmaceutically acceptable carrier or excipient.
18. A crystalline form of Compound I having the structure:
characterized by an XRPD pattern comprising peaks at 5.8, 11.6, 22.3, and 23.9 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using CuK α1 radiation.
19. The crystalline form of claim 18 , characterized by an XRPD pattern comprising peaks at 5.8, 11.6, 17.7, 22.3, 23.9, 26.0 and 26.8 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using CuK α1 radiation.
20. A pharmaceutical composition comprising a therapeutically effective amount of the crystalline form of Compound I of claim 18 , and a pharmaceutically acceptable carrier or excipient.