Claims for Patent: 12,404,227

Summary for Patent: 12,404,227

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:	Esperion Therapeutics Inc
Application Number:	US18/450,591
Patent Claims:	1. 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 0.15% or a pharmaceutically acceptable salt thereof, based on the total weight of the pharmaceutical material. 2. The pharmaceutical material of claim 1, wherein the crystalline form of the compound of formula (V) exhibits an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):10.4±0.2, 17.91±0.2, 18.8±0.2, 19.5±0.2, and 20.7±0.2. 3. The pharmaceutical material 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 . 4. The pharmaceutical material claim 1, wherein the crystalline form of the compound of formula (V) has a melting point onset as determined by differential scanning calorimetry in the range of from about 90° C. to about 94° C. 5. The pharmaceutical material of claim 1, wherein the pharmaceutical material comprises the compound of formula (V) in an amount greater than 99.5% by weight based on the total weight of the pharmaceutical material. 6. 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 about 98% to about 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 0.15% of a compound of formula (VIII): or a pharmaceutically acceptable salt thereof, based on the total weight of the pharmaceutical material. 7. The pharmaceutical material of claim 6, wherein the HPLC assay uses a C18 column (4.6 mm i.d.×150 mm, 2.5 μm) at a temperature of about 40° C., with isocratic elution of a mobile phase comprising about 0.05% phosphoric acid in water/acetonitrile (about 50:50) at a flow rate of about 1.2 mL/minute, and detection at 215 nm, wherein the retention time of the compound of formula (V) is about 4.6 minutes. 8. A method of treating primary hyperlipidemia in a patient in need thereof, the method comprising administering to a patient a therapeutically-effective amount of the pharmaceutical material of claim 1. 9. 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 0.15% of a compound of formula (VIII): or a pharmaceutically acceptable salt thereof, based on the total weight of the pharmaceutical material. 10. The pharmaceutical material of claim 9 wherein the crystalline form of the compound of formula (V) exhibits an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ):10.4±0.2, 17.9±0.2, 18.8±0.2, 19.5±0.2, and 20.7±0.2. 11. The pharmaceutical material 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 pharmaceutical material of claim 9 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. 13. The pharmaceutical material of claim 9, 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. 14. The pharmaceutical material of claim 9, 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. 15. The pharmaceutical material of claim 9, 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. 16. The pharmaceutical material of claim 9, wherein the pharmaceutical material comprises the compound of formula (V) or a pharmaceutically acceptable salt thereof, in an amount greater than 98% by weight based on the total weight of the pharmaceutical material. 17. The pharmaceutical material of claim 9, further comprising a compound of formula (VI): or a pharmaceutically acceptable salt thereof. 18. The pharmaceutical material of claim 17, wherein the pharmaceutical material comprises 0.0001% to 0.15% of a compound of formula (VI), based on the total weight of the pharmaceutical material. 19. The pharmaceutical material of claim 1, further comprising a compound of formula (VI): or a pharmaceutically acceptable salt thereof. 20. The pharmaceutical material of claim 19, wherein the pharmaceutical material comprises 0.0001% to 0.15% of a compound of formula (VI), based on the total weight of the pharmaceutical material.