IP Library › Granted Patent US 12,419,877
Granted Patent B2
US 12,419,877 · App. 18/319,287 · Granted Sep 23, 2025

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

Inventors: James Densmore Copp (Silverthorne, CO); Ann W. Newman (Lafayette, IN); Anne Luong (Mississauga, CA)
Assignee: Akebia Therapeutics, Inc.
A61K31/444A61K9/14A61K9/2054A61K9/48A61K9/4866A61K31/4418C07D213/803C07D213/81C07B2200/13C07D221/00
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Quick Facts
Patent No.
US 12,419,877
App. No.
18/319,287
Granted
Sep 23, 2025
Kind
B2
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.

Claims (33)

1. A method for preparing the Crystalline Compound (I):

comprising

a) preparing a solution of a Compound (I) in an organic solvent that is acetonitrile; and

b) evaporating the organic solvent;

wherein the Crystalline Compound (1) has X-ray powder diffraction pattern comprising peaks at 8.6, 15.3, 22.7, and 28.1±0.2° 2θ.

2. The method of claim 1 , wherein the Crystalline Compound (I) comprises less than 10% by weight of any other amorphous or crystalline forms of Compound (I).

3. The method of claim 2 , wherein the Crystalline Compound (I) comprises less than 5% by weight of any other amorphous or crystalline forms of Compound (I).

4. 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.

5. The method of claim 4 , wherein the Crystalline Compound (I) comprises less than 50 ppm of a compound of Formula (II).

6. The method of claim 5 , wherein the Crystalline Compound (I) comprises less than 10 ppm of a compound of Formula (II).

7. The method of claim 1 , wherein the Crystalline Compound (I) is at least 99.5% pure as measured by HPLC.

8. A method for preparing the Crystalline Compound (I):

comprising

a) preparing a solution of a Compound (I) in an organic solvent that is 2-methyltetrahydrofuran;

b) adding n-heptane;

c) heating the suspension;

d) cooling the suspension; and

e) isolating the crystals

wherein the Crystalline Compound (1) has X-ray powder diffraction pattern comprising peaks at 7.2, 17.4, 22.3, 22.4, 28.9, 33.7, and 33.8±0.2° 2θ.

9. The method of claim 8 , wherein the Crystalline Compound (I) comprises less than 10% by weight of any other amorphous or crystalline forms of Compound (I).

10. The method of claim 9 , wherein the Crystalline Compound (I) comprises less than 5% by weight of any other amorphous or crystalline forms of Compound (I).

11. The method of claim 8 , wherein the Crystalline Compound (I) comprises less than 100 ppm of a compound of Formula (II):

as determined by GC/MS.

12. The method of claim 11 , wherein the Crystalline Compound (I) comprises less than 50 ppm of a compound of Formula (II).

13. The method of claim 12 , wherein the Crystalline Compound (I) comprises less than 10 ppm of a compound of Formula (II).

14. The method of claim 8 , wherein the Crystalline Compound (I) is at least 99.5% pure as measured by HPLC.

15. The method of claim 8 , wherein the adding of the n-heptane in step b) is carried out over not less than 30 minutes.

16. The method of claim 8 , wherein the adding of the n-heptane in step b) is carried out at 40-50° C.

17. The method of claim 8 , wherein the isolating of the crystals in step e) comprises filtering the crystals.

18. The method of claim 17 , further comprising washing the crystals.

19. The method of claim 18 , further comprising washing the crystals with cold n-heptane/2-methyltetrahydrofuran.

20. The method of claim 8 , further comprising drying the crystals under vacuum.

Assignments (2)
SECURITY INTEREST Recorded Jan 29, 2024
From: AKEBIA THERAPEUTICS, INC.; KERYX BIOPHARMACEUTICALS, INC.
To: KREOS CAPITAL VII (UK) LIMITED
Reel/Frame 066377/0654 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 6, 2023
From: COPP, JAMES DENSMORE; NEWMAN, ANN W.; LUONG, ANNE
To: AKEBIA THERAPEUTICS, INC.
Reel/Frame 063861/0223 →
Continuity (8)
Continuation 17347700 · Jun 15, 2021
Continuation 16786187 · Feb 10, 2020
Continuation 16178191 · Nov 1, 2018
Continuation 15994348 · May 31, 2018
Division 15608186 · May 30, 2017
Division 14541284 · Nov 14, 2014
Provisional Application 61904803 · Nov 15, 2013
Related Publication 20240122910A1 · Apr 18, 2024
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