Claims for Patent: 10,259,791

Summary for Patent: 10,259,791

Title:	High-purity quinoline derivative and method for manufacturing same
Abstract:	Provided is a compound represented by formula (IV) or a salt thereof, wherein the content of the compound represented by formula (I) is 350 ppm by mass or less.
Inventor(s):	Taiju Nakamura, Taichi Abe, Yusuke Miyashita, Hirofumi Kuroda, Yusuke Ayata, Atsushi Akao
Assignee:	Eisai R&D Management Co Ltd
Application Number:	US15/503,108
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 10,259,791
Patent Claims:	1. A methanesulfonate salt of a compound represented by formula (IV), wherein the content of a compound represented by formula (A-1) is 60 ppm by mass or less 2. The methanesulfonate salt of a compound represented by formula (IV) according to claim 1, wherein the content of a compound represented by formula (I) is 183 ppm by mass or less, and the content of a compound represented by formula (A-1) is 60 ppm by mass or less 3. A method for producing a compound represented by formula (IV) or a salt thereof, comprising: a step B of allowing a compound represented by formula (I) or a salt thereof to react with a compound represented by formula (II-A) or formula (II-B) wherein R1 is a C1-6 alkyl group, a C2-6 alkenyl group, a C6-10 aryl group, or a C7-11 aralkyl group, wherein the C1-6 alkyl group or the C2-6 alkenyl group may have one to three substituents that may be the same or different and are selected from the group consisting of a halogen atom and a methoxy group, and wherein the C6-10 aryl group or the C7-11 aralkyl group may have one to three substituents that may be the same or different and are selected from the group consisting of a halogen atom, a methyl group, a methoxy group, and a nitro group; and X is a halogen atom, in the presence of a base to thereby obtain a compound represented by formula (III) wherein R1 is the same group as above, and a step C of, after allowing the compound represented by formula (III) obtained in the step B to react without isolation with cyclopropylamine, precipitating and isolating a compound represented by formula (IV) or a salt thereof by introducing a hydrous organic solvent to a reaction solution. 4. The method according to claim 3, comprising: a step A of, after allowing a compound represented by formula (A-1) to react with a compound represented by formula (A-2) or a salt thereof in the presence of a base, precipitating and isolating a compound presented by formula (I) or a salt thereof from a reaction solution by introducing a hydrous organic solvent to the reaction solution, a step B of allowing the compound represented by formula (I) or a salt thereof obtained in the step A to react with a compound represented by formula (II-A) or formula (II-B) wherein R1 is a C1-6 alkyl group, a C2-6 alkenyl group, a C6-10 aryl group, or a C7-11 aralkyl group, wherein the C1-6 alkyl group or the C2-6 alkenyl group may have one to three substituents that may be the same or different and are selected from the group consisting of a halogen atom and a methoxy group, and wherein the C6-10 aryl group or the C7-11 aralkyl group may have one to three substituents that may be the same or different and are selected from the group consisting of a halogen atom, a methyl group, a methoxy group, and a nitro group; and X is a halogen atom, in the presence of a base to thereby obtain a compound represented by formula (III) wherein R1 is the same group as above, and a step C of, after allowing the compound represented by formula (III) obtained in the step B to react without isolation with cyclopropylamine, precipitating and isolating a compound represented by formula (IV) or a salt thereof by introducing a hydrous organic solvent to a reaction solution. 5. The method according to claim 3, further comprising a step D of converting the compound represented by formula (IV) obtained in the step C into a salt of the compound represented by formula (IV). 6. The method according to claim 5, wherein the salt obtained in the step D is a methanesulfonate. 7. The method according to claim 3, wherein the step B is a step of allowing the compound represented by formula (I) or a salt thereof to react with the compound represented by formula (II-A) wherein R1 is a C6-10 aryl group that may have one to three substituents that may be the same or different and are selected from the group consisting of a halogen atom, a methyl group, a methoxy group, and a nitro group; and X is a halogen atom, in the presence of a base to thereby obtain a compound represented by formula (III) wherein R1 is the same group as above. 8. The method according to claim 3, wherein the compound represented by formula (II-A) is phenyl chloroformate. 9. The methanesulfonate salt of a compound represented by formula (IV) according to claim 3, wherein the content of the methanesulfonate salt of a compound represented by formula (IV) is 98.0% by mass or more 10. The methanesulfonate salt of a compound represented by formula (IV) according to claim 2, wherein the content of the methanesulfonate salt of a compound represented by formula (IV) is 98.0% by mass or more 11. The methanesulfonate salt of a compound represented by formula (IV) according to claim 3, wherein the content of the compound represented by formula (A-1) is determined by HPLC. 12. The methanesulfonate salt of a compound represented by formula (IV) according to claim 2, wherein the content of the compound represented by formula (I) and the content of the compound represented by formula (A-1) are measured by HPLC.