Salt forms of bempedoic acid and methods for using the same
AssigneeEsperion Therapeutics, Inc.
InventorsRichard Copp, Mohamed Abdelnasser, Christopher M. Cimarusti, Chengxiang Liu
Life of this patent
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Abstract
The invention provides crystalline salt and cocrystal forms of bempedoic acid. Also provided are compositions and pharmaceutical materials including a crystalline salt or cocrystal form of bempedoic acid as well as methods of treating various diseases and conditions using the compositions and pharmaceutical materials.
Claims38
The crystalline form of claim 61, wherein the crystalline form is the crystalline betaine salt of the compound of formula (V):
- wherein the crystalline betaine salt of the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 6.2±0.2°, 13.5±0.2°, and 25.6±0.2°.
-4. (canceled)
The crystalline form of claim 61, wherein the crystalline form is the crystalline calcium salt of the compound of formula (V):
- wherein the crystalline calcium salt of the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 4.9±0.2°, 9.1±0.2°, and 19.7±0.2°.
-7. (canceled)
The crystalline form of claim 61, wherein the crystalline form is the crystalline calcium salt of the compound of formula (V):
- wherein the crystalline calcium salt of the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 6.0±0.2°, 6.8±0.2°, 8.5±0.2°, and 9.8±0.2°.
-10. (canceled)
The crystalline form of claim 61, wherein the crystalline form is the crystalline diethylamine salt of the compound of formula (V):
- wherein the crystalline diethylamine salt of the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 9.6±0.2°, 14.1±0.2°, and 19.8±0.2°.
(canceled)
The crystalline form of claim 61, wherein the crystalline form is the crystalline ethylenediamine salt of the compound of formula (V):
- wherein the crystalline ethylenediamine salt of the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 10.8±0.2°, 16.2±0.2°, and 18.3±0.2°.
-16. (canceled)
The crystalline form of claim 61, wherein the crystalline form is the crystalline isonicotinamide salt of the compound of formula (V):
- wherein the crystalline isonicotinamide salt of the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 4.4±0.2°, 18.8±0.2°, 20.1±0.2°, and 24.5±0.2°.
-19. (canceled)
The crystalline form of claim 61, wherein the crystalline form is the crystalline potassium salt of the compound of formula (V):
- wherein the crystalline potassium salt of the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 5.7±0.2°, 7.3±0.2°, 9.6±0.2°, and 22.1±0.2°.
-22. (canceled)
The crystalline form of claim 61, wherein the crystalline form is the crystalline L-lysine salt of the compound of formula (V):
- wherein the crystalline L-lysine salt of the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 4.2±0.2°, 19.1±0.2°, and 21.9±0.2°.
-26. (canceled)
The crystalline form of claim 61, wherein the crystalline form is the crystalline sodium salt of the compound of formula (V):
- wherein the crystalline sodium salt of the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 6.1±0.2°, 14.2±0.2°, 18.3±0.2°, and 24.5±0.2°.
-29. (canceled)
The crystalline form of claim 61, wherein the crystalline form is the crystalline ammonium salt of the compound of formula (V):
- wherein the crystalline ammonium salt of the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 7.1±0.2°, 14.3±0.2°, and 16.0±0.2°.
-33. (canceled)
The crystalline form of claim 61, wherein the crystalline form is the crystalline piperazine salt of the compound of formula (V):
- wherein the crystalline piperazine salt of the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 6.7±0.2°, 15.7±0.2°, and 16.0±0.2°.
-37. (canceled)
The crystalline form of claim 61, wherein the crystalline form is the crystalline tromethamine salt of the compound of formula (V):
- wherein the crystalline tromethamine salt of the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 6.6±0.2°, 18.2±0.2°, 18.6±0.2°, and 19.8±0.2°.
-40. (canceled)
The co-crystal of claim 62, wherein the co-crystal is the cocrystal of aspartame and the compound of formula (V):
-43. (canceled)
The co-crystal of claim 62, wherein the co-crystal is the cocrystal of aspartame and the compound of formula (V):
- wherein the cocrystal of aspartame and the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 7.6±0.2°, 17.3±0.2°, and 18.4±0.2°.
-47. (canceled)
The co-crystal of claim 62, wherein the co-crystal is the cocrystal of aspartame and the compound of formula (V):
- wherein the cocrystal of aspartame and the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 4.4±0.2°, 10.6±0.2°, and 18.4±0.2°.
-51. (canceled)
The co-crystal of claim 62, wherein the co-crystal is the cocrystal of palmitic acid and the compound of formula (V):
(canceled)
The co-crystal of claim 62, wherein the co-crystal is the cocrystal of palmitic acid and the compound of formula (V):
- wherein the cocrystal of palmitic acid and the compound of formula (V) is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):
- 4.3±0.2°, 6.3±0.2°, 8.5±0.2°, and 17.0±0.2°.
-57. (canceled)
A method of lowering LDL-C or treating cardiovascular disease, the method comprising administering to a patient a therapeutically-effective amount of the crystalline form of the compound of formula (V) of claim 61.
-60. (canceled)
A crystalline form of the compound of formula (V):
- wherein the crystalline form is selected from the group consisting of a crystalline betaine salt, a crystalline calcium salt, a crystalline diethylamine salt, a crystalline ethylenediamine salt, a crystalline isonicotinamide salt, a crystalline potassium salt, a crystalline L-lysine salt, a crystalline sodium salt, a crystalline ammonium salt, a crystalline piperazine salt, and a crystalline tromethamine salt.
A co-crystal comprising the compound of formula (V):
- wherein the co-crystal is a cocrystal of aspartame and the compound of formula (V), or a cocrystal of palmitic acid and the compound of formula (V).
Dependencies are inferred from the claim text.