Claims for Patent: 7,612,208

Summary for Patent: 7,612,208

Title:	Crystalline form of the salt of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide or the solvate of the salt and a process for preparing the same
Abstract:	A crystal of a 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide hydrochloride, hydrobromide, p-toluenesulfonate, sulfate, methanesulfonate or ethanesulfonate, or a solvate thereof.
Inventor(s):	Tomohiro Matsushima, Taiju Nakamura, Kazuhiro Yoshizawa, Atsushi Kamada, Yusuke Ayata, Naoko Suzuki, Itaru Arimoto, Takahisa Sakaguchi, Masaharu Gotoda
Assignee:	Eisai R&D Management Co Ltd
Application Number:	US10/577,531
Patent Claims:	1. A crystalline form (Form A) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate having diffraction peaks at diffraction angles (2θ±0.2°) of 9.65° and 18.37° in a powder X-ray diffraction. 2. A crystalline form (Form A) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate having peaks at chemical shifts of about 162.4 ppm, about 128.0 ppm, about 102.3 ppm and about 9.9 ppm in a 13C Solid State Nuclear Magnetic Resonance spectrum. 3. A crystalline form (Form A) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate having absorption bands at wavenumbers of 1161±1 cm−1 and 1044±1 cm−1 in an infrared absorption spectrum. 4. A crystalline form (Form B) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate having diffraction peaks at diffraction angles (2θ±0.2°) of 5.72° and 13.84° in a powder X-ray diffraction. 5. A crystalline form (Form B) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate having absorption bands at wavenumbers of 1068±1 cm−1 and 918±1 cm−1 in an infrared absorption spectrum. 6. A crystalline form (Form C) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate having diffraction peaks at diffraction angles (2θ±0.2°) of 14.20° and 17.59° in a powder X-ray diffraction. 7. A crystalline form (Form C) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate having peaks at chemical shifts of about 160.2 ppm, about 126.6 ppm, about 105.6 ppm and about 7.8 ppm in a 13C Solid State Nuclear Magnetic Resonance spectrum. 8. A crystalline form (Form C) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate having absorption bands at wavenumbers of 1324±1 cm−1 and 579±1 cm−1 in an infrared absorption spectrum. 9. A crystalline form (Form F) of a hydrate of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate having diffraction peaks at diffraction angles (2θ±0.2°) of 8.02° and 18.14° in a powder X-ray diffraction. 10. A crystalline form (Form I) of an acetic acid solvate of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate having diffraction peaks at diffraction angles (2θ±0.2°) of 9.36° and 12.40° in a powder X-ray diffraction. 11. A crystalline form (Form I) of an acetic acid solvate of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate having absorption bands at wavenumbers of 1750±1 cm−1 and 1224±1 cm−1 in an infrared absorption spectrum. 12. A crystalline form (Form α) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide ethanesulfonate having diffraction peaks at diffraction angles (2θ±0.2°) of 15.70° and 17.18° in a powder X-ray diffraction. 13. A crystalline form (Form α) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide ethanesulfonate having absorption bands at wavenumbers of 1320±1 cm−1 and 997±1 cm−1 in an infrared absorption spectrum. 14. A crystalline form (Form β) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide ethanesulfonate having diffraction peaks at diffraction angles (2θ±0.2°) of 6.48° and 9.58° in a powder X-ray diffraction. 15. A crystalline form (Form β) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide ethanesulfonate having absorption bands at wavenumbers of 1281±1 cm−1 and 985±1 cm−1 in an infrared absorption spectrum. 16. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate (Form A), comprising a step of mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide, methanol and methanesulfonic acid to dissolve. 17. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate (Form A), comprising: mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide, acetic acid and methanesulfonic acid to dissolve; and adding ethanol to the mixture. 18. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate (Form B), comprising a step of drying a crystalline form of the acetic acid solvate of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate (Form I) at 30° C. for 3 hours and at 40° C. for 16 hours to remove acetic acid. 19. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate (Form C), comprising a step of heating a crystalline form of the dimethyl sulfoxide solvate of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate at 115° C. for 10 hours. 20. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate (Form C), comprising a step of mixing a crystalline form of the acetic acid solvate of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate (Form I) and ethanol. 21. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-methoxy-6-quinolinecarboxamide Methanesulfonate (Form C), comprising: mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide, acetic acid and methanesulfonic acid to dissolve; and adding 2-propanol to the mixture. 22. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate (Form C), comprising a step of humidifying a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate (Form B). 23. A process for preparing a crystalline form of the hydrate of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate (Form F), comprising: mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide, acetic acid and methanesulfonic acid to dissolve and adding ethyl acetate to the mixture. 24. A process for preparing a crystalline form of the acetic acid solvate of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide methanesulfonate (Form I), comprising: mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide, acetic acid and methanesulfonic acid to dissolve; and adding 1-propanol to the mixture. 25. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide ethanesulfonate (Form α), comprising a step of mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide, dimethyl sulfoxide and ethanesulfonic acid to dissolve. 26. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide ethanesulfonate (Form β), comprising a step of mixing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide ethanesulfonate (Form α) and ethanol. 27. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide ethanesulfonate (Form β), comprising: mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide, acetic acid and ethanesulfonic acid to dissolve; and adding 2-propanol and water to the mixture. 28. A pharmaceutical composition in the form of a tablet, powder, granule, capsule or lozenge, said pharmaceutical composition comprising the crystalline form according to claim 15; and a pharmaceutically acceptable carrier.