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

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 13 C 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 13 C 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.