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-quinoli- necarboxamide 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-quinoli- necarboxamide hydrochloride, hydrobromide, p-toluenesulfonate, sulfate, methanesulfonate or ethanesulfonate, or a solvate thereof.
Inventor(s):	Matsushima; Tomohiro (Tsukuba, JP), Nakamura; Taiju (Kamisu, JP), Yoshizawa; Kazuhiro (Kamisu, JP), Kamada; Atsushi (Tsukuba, JP), Ayata; Yusuke (Kamisu, JP), Suzuki; Naoko (Ushiku, JP), Arimoto; Itaru (Tokyo, JP), Sakaguchi; Takahisa (Tsukuba, JP), Gotoda; Masaharu (Tsukuba, JP)
Assignee:	Eisai R&D Management Co., Ltd. (Tokyo, JP)
Application Number:	10/577,531
Patent Claims:	1. A crystalline form (Form A) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide methanesulfonate having diffraction peaks at diffraction angles (2.theta..+-.0.2.degree.) of 9.65.degree. and 18.37.degree. in a powder X-ray diffraction. 2. A crystalline form (Form A) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide 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 .sup.13C Solid State Nuclear Magnetic Resonance spectrum. 3. A crystalline form (Form A) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide methanesulfonate having absorption bands at wavenumbers of 1161.+-.1 cm.sup.-1 and 1044.+-.1 cm.sup.-1 in an infrared absorption spectrum. 4. A crystalline form (Form B) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide methanesulfonate having diffraction peaks at diffraction angles (2.theta..+-.0.2.degree.) of 5.72.degree. and 13.84.degree. in a powder X-ray diffraction. 5. A crystalline form (Form B) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide methanesulfonate having absorption bands at wavenumbers of 1068.+-.1 cm.sup.-1 and 918.+-.1 cm.sup.-1 in an infrared absorption spectrum. 6. A crystalline form (Form C) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide methanesulfonate having diffraction peaks at diffraction angles (2.theta..+-.0.2.degree.) of 14.20.degree. and 17.59.degree. in a powder X-ray diffraction. 7. A crystalline form (Form C) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide 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 .sup.13C Solid State Nuclear Magnetic Resonance spectrum. 8. A crystalline form (Form C) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide methanesulfonate having absorption bands at wavenumbers of 1324.+-.1 cm.sup.-1 and 579.+-.1 cm.sup.-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-quinoli- necarboxamide methanesulfonate having diffraction peaks at diffraction angles (2.theta..+-.0.2.degree.) of 8.02.degree. and 18.14.degree. 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-quinoli- necarboxamide methanesulfonate having diffraction peaks at diffraction angles (2.theta..+-.0.2.degree.) of 9.36.degree. and 12.40.degree. 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-quinoli- necarboxamide methanesulfonate having absorption bands at wavenumbers of 1750.+-.1 cm.sup.-1 and 1224.+-.1 cm.sup.-1 in an infrared absorption spectrum. 12. A crystalline form (Form .alpha.) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide ethanesulfonate having diffraction peaks at diffraction angles (2.theta..+-.0.2.degree.) of 15.70.degree. and 17.18.degree. in a powder X-ray diffraction. 13. A crystalline form (Form .alpha.) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide ethanesulfonate having absorption bands at wavenumbers of 1320.+-.1 cm.sup.-1 and 997.+-.1 cm.sup.-1 in an infrared absorption spectrum. 14. A crystalline form (Form .beta.) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide ethanesulfonate having diffraction peaks at diffraction angles (2.theta..+-.0.2.degree.) of 6.48.degree. and 9.58.degree. in a powder X-ray diffraction. 15. A crystalline form (Form .beta.) of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide ethanesulfonate having absorption bands at wavenumbers of 1281.+-.1 cm.sup.-1 and 985.+-.1 cm.sup.-1 in an infrared absorption spectrum. 16. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide methanesulfonate (Form A), comprising a step of mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide, methanol and methanesulfonic acid to dissolve. 17. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide methanesulfonate (Form A), comprising: mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide, 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-quinoli- necarboxamide 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-quinoli- necarboxamide methanesulfonate (Form I) at 30.degree. C. for 3 hours and at 40.degree. 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-quinoli- necarboxamide 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-quinoli- necarboxamide methanesulfonate at 115.degree. C. for 10 hours. 20. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide 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-quinoli- necarboxamide methanesulfonate (Form I) and ethanol. 21. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-methoxy-6-quinoline- carboxamide Methanesulfonate (Form C), comprising: mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide, 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-quinoli- necarboxamide methanesulfonate (Form C), comprising a step of humidifying a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide methanesulfonate (Form B). 23. A process for preparing a crystalline form of the hydrate of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide methanesulfonate (Form F), comprising: mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide, 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-quin- olinecarboxamide methanesulfonate (Form I), comprising: mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide, 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-quinoli- necarboxamide ethanesulfonate (Form .alpha.), comprising a step of mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide, 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-quinoli- necarboxamide ethanesulfonate (Form .beta.), comprising a step of mixing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide ethanesulfonate (Form .alpha.) and ethanol. 27. A process for preparing a crystalline form of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide ethanesulfonate (Form .beta.), comprising: mixing 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinoli- necarboxamide, 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.