Granted Patent B2

US 12,269,802 · App. 18/334,101 · Granted Apr 8, 2025

Inventors: Boris I. Gorin (Oakville, CA); Christopher M. Lanthier (Burlington, CA); Anne Buu Chau Luong (Mississauga, CA); James Densmore Copp (Bargersville, IN); Javier Gonzalez (Lafayette, IN); Sascha Jautze (Piscataway, NJ); Erich Kraus (Essen, DE); Alan O'Connor (Piscataway, NJ)

Assignee: Akebia Therapeutics, Inc.

C07D213/81

Abstract

Claims (30)

1. A compound of Formula (I):

or a salt thereof, wherein:

R 1 is C 1-4 alkyl, CH 2 Cl, phenyl, or benzyl, in which each of phenyl and benzyl may be independently substituted with one, two or three substituents selected from methyl, methoxy, nitro and halogen; and

R 2 is C 1-4 alkyl; and

wherein the compound comprises less than about 0.5% of the compound of Formula (5):

2. The compound of claim 1 or a salt thereof, wherein R 1 is t-butyl and/or R 2 is methyl.

3. The compound of claim 1 or a salt thereof, which is at least about 80% pure, about 85% pure, about 90% pure, or about 95% pure.

4. The compound of claim 1 or a salt thereof, wherein the compound comprises less than about 0.3% of the compound of Formula (5).

5. The compound of claim 1 or a salt thereof, wherein the compound comprises less than about 0.2% of the compound of Formula (5).

6. The compound of claim 1 or a salt thereof, wherein the compound comprises less than about 0.1% of the compound of Formula (5).

7. The compound of claim 1 or a salt thereof, wherein the compound comprises less than about 0.05% of the compound of Formula (5).

8. The compound of claim 1 or a salt thereof, wherein the compound of Formula (I) is isolated.

9. A composition comprising:

a) 80% or more of a compound of Formula (I) or a salt thereof,

wherein:

R 1 is C 1-4 alkyl, CH 2 Cl, phenyl, or benzyl, in which each of phenyl and benzyl may be independently substituted with one, two or three substituents selected from methyl, methoxy, nitro and halogen;

R 2 is C 1-4 alkyl; and

b) 20% or less of a compound of Formula (IV) or a salt thereof,

wherein R 2 is C 1-4 alkyl;

wherein the composition comprises less than about 0.5% of the compound of Formula (5):

and

wherein the combined amount of the compound of Formula (I), or a salt thereof, and the compound of Formula (IV), or a salt thereof, is between about 99% and about 100% of the composition.

10. The composition of claim 9 , wherein R 1 is t-butyl and or R 2 is methyl.

11. The composition of claim 9 , comprising 85% or more of the compound of Formula (I), or a salt thereof, and 15% or less of the compound of Formula (IV), or a salt thereof.

12. The composition of claim 9 , comprising 90% or more of the compound of Formula (I), or a salt thereof, and 10% or less of the compound of Formula (IV), or a salt thereof.

13. The composition of claim 9 , comprising less than about 0.3% of the compound of Formula (5).

14. The composition of claim 9 , comprising less than about 0.2% of the compound of Formula (5).

15. The composition of claim 9 , comprising less than about 0.1% of the compound of Formula (5).

16. The composition of claim 9 , comprising less than about 0.05% of the compound of Formula (5).

17. The compound of claim 3 , wherein purity is as measured by HPLC.

Assignments (7)

Continuity (3)

References Cited (323)