Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof

Patent metadata

Field	Value
Publication number	US-10596158-B2
Application number	US-201816178191-A
Country	US
Kind code	B2
Filing date	Nov 1, 2018
Priority date	Nov 15, 2013
Publication date	Mar 24, 2020
Grant date	Mar 24, 2020

Abstract

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.

First claim

What is claimed is:

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.

Assignees

• Akebia Therapeutics Inc

Inventors

• Copp James Densmore
• Newman Ann W
• Luong Anne

Classifications

• A61K9/2054 Primary

  Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P7/06

  Antianaemics · CPC title

• C07D213/81 Primary

  Amides; Imides · CPC title