Claims for Patent: 11,981,659

Summary for Patent: 11,981,659

Title:	Salt of an aminopyridine derivative compound, a crystalline form thereof, and a process for preparing the same
Abstract:	The present invention relates to novel mesylate salt of N-(5-(4-(4-((dimethylamino)methyl)-3-phenyl-1H-pyrazol-1-yl)pyrimidine-2-ylamino)-4-methoxy-2-morpholinophenyl)acrylamide, a novel crystalline form thereof, and a process for preparing the same. More specifically, the present invention relates to mesylate salt of N-(5-(4-(4-((dimethylamino)methyl)-3-phenyl-1H-pyrazol-1-yl)pyrimidine-2-ylamino)-4-methoxy-2-morpholinophenyl)acrylamide, which is excellent in stability, solubility, and bioavailability when it is administered not only alone but also in combination with other drugs and which has a high purity, a crystalline form thereof, and a process for preparing the same.
Inventor(s):	Sang Ho Oh, Jong Gyun Kim, Se-Woong Oh, Tae Dong Han, Soo Yong Chung, Seong Ran LEE, Kyeong Bae Kim, Young Sung Lee, Woo Seob Shin, Hyun Ju, Jeong Ki Kang, Su Min Park, Dong Kyun Kim
Assignee:	Yuhan Corp
Application Number:	US17/697,655
Patent Claims:	1. A method of treating a protein kinase-mediated disorder, which comprises the step of administering to a subject a mesylate salt of N-(5-(4-(4-((dimethylamino)methyl)-3-phenyl-1H-pyrazol-1-yl)pyrimidine-2-ylamino)-4-methoxy-2-morpholinophenyl)acrylamide, as represented by the following Formula 1: which is in a crystalline form (I) that has diffraction peaks in a PXRD (powder X-ray diffraction) graph present at 2θ (theta) angles of 5.614±0.2, 17.143±0.2, and 21.585±0.2 degrees. 2. A method of inhibiting the activity of epidermal growth factor receptor (EGFR) having at least one mutation as compared with wild-type EGFR, which comprises the step of administering to a subject a mesylate salt of N-(5-(4-(4-((dimethylamino)methyl)-3-phenyl-1H-pyrazol-1-yl)pyrimidine-2-ylamino)-4-methoxy-2-morpholinophenyl)acrylamide, as represented by the following Formula 1: which is in a crystalline form (I) that has diffraction peaks in a PXRD (powder X-ray diffraction) graph present at 2θ (theta) angles of 5.614±0.2, 17.143±0.2, and 21.585±0.2 degrees. 3. The method according to claim 1, wherein the crystalline form (I) has diffraction peaks in a PXRD (powder X-ray diffraction) graph present at 2θ (theta) angles of 5.614±0.2, 12.394±0.2, 14.086±0.2, 17.143±0.2, 21.585±0.2, 22.131±0.2, and 22.487±0.2 degrees. 4. The method according to claim 1, wherein the crystalline form (I) has diffraction peaks in a PXRD (powder X-ray diffraction) graph present at 2θ (theta) angles of 5.614±0.2, 12.394±0.2, 14.086±0.2, 17.143±0.2, 18.020±0.2, 19.104±0.2, 21.585±0.2, 22.131±0.2, and 22.487±0.2 degrees. 5. The method according to claim 1, wherein the crystalline form (I) has an endothermic transition peak value at 210 to 230° C. in a DSC (differential scanning calorimetry) graph. 6. The method according to claim 5, wherein the crystalline form (I) has an endothermic transition peak value at 217±2° C. in a DSC graph. 7. The method according to claim 1, wherein the crystalline form (I) has a water content of about 2.48% to about 3.19%. 8. The mesylate salt of claim 7, wherein the crystalline form (I) has a water content of about 2.70%. 9. The method according to claim 2, wherein the crystalline form (I) has diffraction peaks in a PXRD (powder X-ray diffraction) graph present at 2θ (theta) angles of 5.614±0.2, 12.394±0.2, 14.086±0.2, 17.143±0.2, 21.585±0.2, 22.131±0.2, and 22.487±0.2 degrees. 10. The method according to claim 2, wherein the crystalline form (I) has diffraction peaks in a PXRD (powder X-ray diffraction) graph present at 2θ (theta) angles of 5.614±0.2, 12.394±0.2, 14.086±0.2, 17.143±0.2, 18.020±0.2, 19.104±0.2, 21.585±0.2, 22.131±0.2, and 22.487±0.2 degrees. 11. The method according to claim 2, wherein the crystalline form (I) has an endothermic transition peak value at 210 to 230° C. in a DSC (differential scanning calorimetry) graph. 12. The method according to claim 11, wherein the crystalline form (I) has an endothermic transition peak value at 217±2° C. in a DSC graph. 13. The method according to claim 2, wherein the crystalline form (I) has a water content of about 2.48% to about 3.19%. 14. The method of claim 13, wherein the crystalline form (I) has a water content of about 2.70%. 15. The method according to claim 1, wherein the protein kinase-mediated disorder is non-small cell lung cancer. 16. The method according to claim 1, wherein the protein kinase-mediated disorder is non-small cell lung cancer with at least one EGFR mutation as compared with wild-type EGFR. 17. The method according to claim 2, wherein the subject has non-small cell lung cancer.