Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof
Provided herein are solid forms comprising {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions comprising the solid forms, methods of making the solid forms and methods of their use for the treatment of various diseases and/or disorders.
1. A method for preparing a crystalline Compound (I):
a) preparing a solution of a Compound (I) in an organic solvent that is acetone;
b) bringing the solution to super-saturation to cause formation of crystals; and
c) isolating the crystals.
2. The method of claim 1 , wherein the crystalline Compound (I) has an X-ray powder diffraction pattern comprising peaks at 18.1, 20.3, 22.9, 24.0, and 26.3±2° 2θ.
3. The method of claim 1 , wherein the crystalline Compound (I) comprises less than 10% by weight of any other crystalline Compound (I).
4. The method of claim 3 , wherein the crystalline compound (I) comprises less than 5% by weight of any other crystalline Compound (I).
5. The method of claim 1 , wherein the crystalline compound comprises less than 10% by weight of amorphous Compound (I).
6. The method of claim 5 , wherein the crystalline compound (I) comprises less than 5% by weight of amorphous Compound (I).
7. The method of claim 1 , wherein the crystalline compound (I) has a DSC endotherm at about 175.8° C.
8. The method of claim 1 , wherein the crystalline compound (I) comprises less than 100 ppm of a compound of Formula (II),
as determined by GC/MS.
9. The method of claim 8 , wherein the crystalline compound (I) comprises less than 50 ppm of a compound of Formula (II).
10. The method of claim 9 , wherein the crystalline compound (I) comprises less than 10 ppm of a compound of Formula (II).
11. The method of claim 10 , wherein the crystalline Compound (I) is at least 99.5% pure as measured by HPLC.
12. The method of claim 1 , further comprising filtering the solution through a charcoal filter.
13. The method of claim 1 , wherein bringing the solution to super-saturation comprises addition of an anti-solvent that is water, allowing the solution to cool, and reducing the volume of the solution by evaporation, solvent exchange, or any combination thereof.
14. The method of claim 1 , further comprising washing the crystals.
15. The method of claim 14 , wherein the washing comprises washing with acetone or water, or any combination thereof.
16. The method of claim 14 , wherein the washing comprises washing with a combination of acetone and water.
17. The method of claim 1 , wherein isolating the crystals comprises filtering the crystals.
18. The method of claim 1 , further comprising drying the crystals under reduced pressure, optionally at an elevated temperature.
19. The method of claim 18 , wherein the drying is performed at a temperature of about 50° C.