Salt and crystalline forms thereof of a drug

1. A composition comprising D-glucitol, 1-deoxy-1-(methylamino)-, 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxyazetidin-1-yl)-4-oxo-3-quinolinecarboxylate salt prepared by a process comprising the steps of:

(1) combining 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxyazetidin-1-yl)-4-oxo-3-quinolinecarboxylate and 1-deoxy-1-(methylamino)-D-glucitol in a solvent to provide a mixture;

(2) filtering said mixture to provide a solid; and

(3) drying said solid to provide said D-glucitol, 1-deoxy-1-(methylamino)-, 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxyazetidin-1-yl)-4-oxo-3-quinolinecarboxylate salt.

2. The composition of claim 1 , wherein the salt is crystalline.

3. The composition of claim 2 , wherein the salt has substantial crystalline purity.

4. The composition of claim 3 , wherein the salt has at least about 95% crystalline purity.

5. The composition of claim 1 , wherein the salt has substantial chemical purity.

6. The composition of claim 5 , wherein the salt is about 97% chemically pure.

7. The composition of claim 5 , wherein the salt is about 98% chemically pure.

8. The composition of claim 5 , wherein the salt is about 100% chemically pure.

9. A therapeutic composition comprising at least one excipient and D-glucitol, 1-deoxy-1-(methylamino)-, 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxyazetidin-1-yl)-4-oxo-3-quinolinecarboxylate salt prepared by a process comprising the steps of:

(1) combining 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxyazetidin-1-yl)-4-oxo-3-quinolinecarboxylate and 1-deoxy-1-(methylamino)-D-glucitol in a solvent to provide a mixture;

(2) filtering said mixture to provide a solid; and

(3) drying said solid to provide said D-glucitol, 1-deoxy-1-(methylamino)-, 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxyazetidin-1-yl)-4-oxo-3-quinolinecarboxylate salt.

10. The therapeutic composition of claim 9 , wherein the salt is present in a therapeutically acceptable amount.

11. The therapeutic composition of claim 9 , wherein the salt is crystalline.

12. The therapeutic composition of claim 11 , wherein the salt has substantial crystalline purity.

13. The therapeutic composition of claim 12 , wherein the salt has at least about 95% crystalline purity.

14. The therapeutic composition of claim 9 , wherein the salt has substantial chemical purity.

15. The therapeutic composition of claim 14 , wherein the salt is about 97% chemically pure.

16. The therapeutic composition of claim 14 , wherein the salt is about 98% chemically pure.

17. The therapeutic composition of claim 14 , wherein the salt is about 100% chemically pure.

18. The therapeutic composition of claim 10 , wherein the composition is an orally administered dosage form.

19. The therapeutic composition of claim 10 , wherein the composition is a solid dosage form for oral administration.

20. The therapeutic composition of claim 10 , wherein the composition is a parenterally administered dosage form.

21. The therapeutic composition of claim 9 , wherein the at least one excipient is selected from the group consisting of agar, alginic acid, aluminum hydroxide, benzyl alcohol, benzyl benzoate, 1,3-butylene glycol, carbomers, castor oil, cellulose, cellulose acetate, cocoa butter, corn starch, corn oil, cottonseed oil, cross-povidone, diglycerides, ethanol, ethyl cellulose, ethyl laurate, ethyl oleate, fatty acid esters, gelatin, germ oil, glucose, glycerol, groundnut oil, hydroxypropylmethyl cellulose, isopropanol, isotonic saline, lactose, magnesium hydroxide, magnesium stearate, malt, mannitol, monoglycerides, olive oil, peanut oil, potassium phosphate salts, potato starch, povidone, propylene glycol, Ringer's solution, safflower oil, sesame oil, sodium carboxymethyl cellulose, sodium phosphate salts, sodium lauryl sulfate, sodium sorbitol, soybean oil, stearic acids, stearyl fumarate, sucrose, surfactants, talc, tragacanth, tetrahydrofurfuryl alcohol, triglycerides, water, and mixtures thereof.

22. The therapeutic composition of claim 9 , wherein said at least one excipient comprises at least one filler, at least one binder, at least one disintegrating agent, at least one buffering agent and at least one lubricant.

23. The therapeutic composition of claim 22 , wherein the salt is present in a therapeutically acceptable amount.

24. The therapeutic composition of claim 22 , wherein the salt is crystalline.

25. The therapeutic composition of claim 24 , wherein the salt has substantial crystalline purity.

26. The therapeutic composition of claim 25 , wherein the salt has at least about 95% crystalline purity.

27. The therapeutic composition of claim 22 , wherein the salt has substantial chemical purity.

28. The therapeutic composition of claim 27 , wherein the salt is about 97% chemically pure.

29. The therapeutic composition of claim 27 , wherein the salt is about 98% chemically pure.

30. The therapeutic composition of claim 27 , wherein the salt is about 100% chemically pure.

31. The therapeutic composition of claim 22 , wherein the composition is an orally administered dosage form.

32. The therapeutic composition of claim 22 , wherein the at least one filler comprises cellulose.

33. The therapeutic composition of claim 22 , wherein the at least one binder comprises povidone.

34. The therapeutic composition of claim 22 , wherein the at least one disintegrating agent comprises cross-povidone.

35. The therapeutic composition of claim 22 , wherein the at least one buffering agent comprises a sodium phosphate salt.

36. The therapeutic composition of claim 22 , wherein the at least one buffering agent comprises a citrate.

37. The therapeutic composition of claim 22 , wherein the at least one lubricant comprises magnesium stearate.

38. The therapeutic composition of claim 22 , wherein the at least one filler comprises cellulose, the at least one binder comprises povidone, the at least one disintegrating agent comprises cross-povidone, the at least one buffering agent comprises a sodium phosphate salt, and the at least one lubricant comprises magnesium stearate.

39. The therapeutic composition of claim 38 , further comprising a citrate.

40. The therapeutic composition of claim 9 , wherein said at least one excipient comprises cellulose, povidone, cross-povidone, a sodium phosphate salt and magnesium stearate.

41. The therapeutic composition of claim 40 , further comprising a citrate.

42. A method of treating a bacterial infection in a fish or a mammal comprising administering thereto a therapeutic composition of claim 9 .

43. The method of claim 42 , wherein the composition is administered to a mammal.

44. The method of claim 42 , wherein the therapeutically acceptable amount is from about 0.03 to about 200 mg/kg body weight.

45. A method of treating a bacterial infection in a fish or a mammal comprising administering thereto a therapeutic composition of claim 21 .

46. The method of claim 45 , wherein the composition is administered to a mammal.

47. The method of claim 45 , wherein the therapeutically acceptable amount is from about 0.03 to about 200 mg/kg body weight.

48. A method of treating a bacterial infection in a fish or a mammal comprising administering thereto a therapeutic composition of claim 22 .

49. The method of claim 48 , wherein the composition is administered to a mammal.

50. The method of claim 48 , wherein the therapeutically acceptable amount is from about 0.03 to about 200 mg/kg body weight.

51. A method of treating a bacterial infection in a fish or a mammal comprising administering thereto a therapeutic composition of claim 38 .

52. The method of claim 51 , wherein the composition is administered to a mammal.

53. The method of claim 51 , wherein the therapeutically acceptable amount is from about 0.03 to about 200 mg/kg body weight.