Claims for Patent: 11,926,584

Summary for Patent: 11,926,584

Title:	Methods of making bempedoic acid and compositions of the same
Abstract:	The invention provides methods of preparing 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid and methods of making a pharmaceutical material comprising a purified amount of 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid. Also provided are compositions and pharmaceutical materials including a purified amount of 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid as well as methods of treating various diseases and conditions using the compositions and pharmaceutical materials.
Inventor(s):	Richard Copp, Mohamed Abdelnasser, Christopher M. Cimarusti, Jonathan Lane, Michael Barkman, Rasidul Amin, Arthur John Cooper, Damodaragounder Gopal, Philipp Selig
Assignee:	Olon Ricerca Bioscience LLC , Esperion Therapeutics Inc
Application Number:	US18/297,846
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 11,926,584
Patent Claims:	1. A method of lowering low-density lipoprotein cholesterol (LDL-C) in a human in need thereof comprising administering to the human a therapeutically effective amount of a pharmaceutical material comprising a crystalline form of the compound of formula (V): or a pharmaceutically acceptable salt thereof; wherein the pharmaceutical material comprises the compound of formula (V), or a pharmaceutically acceptable salt thereof, in an amount greater than 99.0% by weight based on the total weight of the pharmaceutical material, and the pharmaceutical material comprises 0.0001% to less than or equal to 0.15% of a compound of formula (VI): 2. The method of claim 1, wherein the crystalline form of the compound of formula (V) is characterized by an X-ray powder diffraction pattern substantially the same as shown in FIG. 4 . 3. The method of claim 1, wherein the crystalline form of the compound of formula (V) has a melting point onset as determined by differential scanning calorimetry in a range from 90° C. to 94° C. 4. The method of claim 1, wherein the pharmaceutical material comprises the compound of formula (V), or a pharmaceutically acceptable salt thereof, in an amount greater than 99.5% by weight based on the total weight of the pharmaceutical material. 5. The method of claim 1, wherein the pharmaceutical material comprises the compound of formula (V), or a pharmaceutically acceptable salt thereof, in an amount greater than 99.7% by weight based on the total weight of the pharmaceutical material. 6. The method of claim 1, wherein the pharmaceutical material comprises the compound of formula (V), or a pharmaceutically acceptable salt thereof, in an amount greater than 99.9% by weight based on the total weight of the pharmaceutical material. 7. The method of claim 1, wherein the pharmaceutical material comprises less than or equal to 0.2% by weight of unknown impurities. 8. The method of claim 1, further comprising administering a second therapeutic agent, wherein the second therapeutic agent is ezetimibe. 9. A method of lowering low-density lipoprotein cholesterol (LDL-C) in a human in need thereof comprising administering to the human a therapeutically effective amount of a pharmaceutical material comprising a crystalline form of the compound of formula (V): wherein the pharmaceutical material comprises the compound of formula (V) in an amount of from 98% to 102% by weight based on the total weight of the pharmaceutical material, as determined by a high performance liquid chromatography (HPLC) assay; and the pharmaceutical material comprises 0.0001% to less than or equal to 0.15% of a compound of formula (VI): 10. The method of claim 9, wherein the HPLC assay uses a Waters XBridge BEH C18 column having the dimensions 4.6 mm i.d.×150 mm, with a particle size of 2.5 μm, at a temperature of 40° C., with isocratic elution of a mobile phase comprising 0.05% phosphoric acid in 50:50 water/acetonitrile at a flow rate of 1.2 mL/minute, and detection at 215 nm, wherein the retention time of the compound of formula (V) is 4.6 minutes. 11. The method of claim 9, wherein the pharmaceutical material has a melting point onset as determined by differential scanning calorimetry in a range from 90° C. to 94° C. 12. The method of claim 9, wherein the pharmaceutical material comprises less than or equal to 0.2% by weight of unknown impurities. 13. The method of claim 9, further comprising administering a second therapeutic agent, wherein the second therapeutic agent is ezetimibe. 14. A method of lowering low-density lipoprotein cholesterol (LDL-C) in a human in need thereof comprising administering to the human a therapeutically effective amount of a pharmaceutical material comprising a crystalline form of the compound of formula (V): or a pharmaceutically acceptable salt thereof; wherein the pharmaceutical material comprises the compound of formula (V), or a pharmaceutically acceptable salt thereof, in an amount greater than 85% by weight based on the total weight of the pharmaceutical material, and the pharmaceutical material comprises 0.0001% to less than or equal to 0.15% of a compound of formula (VI): 15. The method of claim 14, wherein the pharmaceutical material has a melting point onset as determined by differential scanning calorimetry in a range from 90° C. to 94° C. 16. The method of claim 14, wherein the pharmaceutical material comprises the compound of formula (V), or a pharmaceutically acceptable salt thereof, in an amount greater than 90% by weight based on the total weight of the pharmaceutical material. 17. The method of claim 14, wherein the pharmaceutical material comprises the compound of formula (V) or a pharmaceutically acceptable salt thereof, in an amount greater than 95% by weight based on the total weight of the pharmaceutical material. 18. The method of claim 14, wherein the pharmaceutical material comprises the compound of formula (V) or a pharmaceutically acceptable salt thereof, in an amount greater than 96% by weight based on the total weight of the pharmaceutical material. 19. The method of claim 14, wherein the pharmaceutical material comprises the compound of formula (V) or a pharmaceutically acceptable salt thereof, in an amount greater than 97% by weight based on the total weight of the pharmaceutical material. 20. The method of claim 14, further comprising administering a second therapeutic agent, wherein the second therapeutic agent is ezetimibe.