Crystalline Forms of D-Glucitol, 1-Deoxy-1-(Methylamino)-, 1-(6-Amino-3,5-Difluoropyridine-2-Yl)-8-Chloro-6-Fluoro-1,4-Dihydro-7-(3-Hydroxyazetidin-1-Yl)-4-Oxo-3-Quinolinecarboxylate

1 . A process for the preparation of a crystalline anhydrous Form 1A of 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-quinolinecarboyxlate, which comprises the steps of:

(a) drying delafloxacin meglumine trihydrate; and

(b) exposing the dried delafloxacin meglumine to heat and humidity.

2 . The process of claim 1 , wherein said drying delafloxacin meglumine trihydrate is performed under reduced pressure.

3 . The process of claim 1 , wherein said drying delafloxacin meglumine trihydrate is performed at a temperature between about 30° C. and about 60° C.

4 . The process of claim 1 , wherein the delafloxacin meglumine trihydrate is dried for between about 24 hours to about 72 hours.

5 . The process of claim 4 , wherein the delafloxacin meglumine trihydrate is dried for about 48 hours.

6 . The process of claim 1 , wherein said heat is between about 30° C. and about 70° C.

7 . The process of claim 6 , wherein said heat is between about 50° C. and about 60° C.

8 . The process of claim 1 , wherein said humidity is between about 30% and about 70% relative humidity.

9 . The process of claim 8 , wherein said humidity is between about 40% and about 60% relative humidity.

10 . The process of claim 1 , wherein the dried delafloxacin meglumine is exposed to heat and humidity for between about 8 hours to about 36 hours.

11 . The process of claim 10 , wherein the dried delafloxacin meglumine is exposed to heat and humidity for about 18 hours.

12 . The process of claim 1 , further comprising drying the delafloxacin meglumine which has been exposed to heat and humidity to further drying.

13 . The process of claim 12 , wherein said further drying comprises drying at a temperature between about 30° C. and about 70° C.

14 . The process of claim 13 , wherein said further drying comprises drying at a temperature between about 50° C. and about 60° C.

15 . The process of claim 12 , wherein the drying occurs at a humidity less than about 30% relative humidity.

16 . The process of claim 12 , wherein the drying occurs for between about 24 hours and about 72 hours.

17 . The process of claim 16 , wherein the drying occurs for about 48 hours.

18 . The process of claim 1 , wherein said drying delafloxacin meglumine trihydrate produces delafloxacin meglumine anhydrate.

19 . The process of claim 12 , wherein said further drying is under reduced pressure.

20 . A process for the preparation of a crystalline anhydrous Form 1B of 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-quinolinecarboyxlate, which comprises drying delafloxacin meglumine trihydrate under low humidity conditions.

21 . The process of claim 20 , wherein said drying occurs at a temperature between about 30° C. and about 40° C.

22 . The process of claim 21 , wherein said drying occurs at a temperature of about 35° C.

23 . The process of claim 20 , wherein said drying occurs under vacuum.

24 . The process of claim 23 , wherein said vacuum comprises a pressure of about 1 to about 10 mbar.

25 . The process of claim 24 , wherein said pressure is about 3 mbar.

26 . The process of claim 20 , wherein said humidity is below about 30% relative humidity.

27 . The process of claim 20 , wherein the delafloxacin meglumine trihydrate is dried for between about 4 hours to about 24 hours.

28 . The process of claim 27 , wherein the delafloxacin meglumine trihydrate is dried for about 12 hours.

29 . A process for producing a crystalline anhydrous Form 1A of 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-quinolinecarboyxlate from a crystalline anhydrous Form 1B of 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-quinolinecarboyxlate, the process comprising exposing delafloxacin meglumine to heat and humidity.

30 . The process of claim 29 , wherein said heat is between about 30° C. and about 60° C.

31 . The process of claim 30 , wherein said heat is between about 40° C. and about 50° C.

32 . The process of claim 29 , wherein said humidity is between about 20% and about 60% relative humidity.

33 . The process of claim 32 , wherein said humidity is between about 30% and about 50% relative humidity.

34 . The process of claim 29 , wherein the dried delafloxacin meglumine trihydrate is exposed to heat and humidity for about 12 hours to about 48 hours.

35 . The process of claim 34 , wherein the dried delafloxacin meglumine trihydrate is exposed to heat and humidity for about 30 hours.

36 . The process of claim 29 , further comprising drying the resulting delafloxacin meglumine to further drying.

37 . The process of claim 36 , wherein said further drying comprises drying at a temperature between about 30° C. and about 70° C.

38 . The process of claim 37 , wherein said further drying comprises drying at a temperature between about 50° C. and about 60° C.

39 . The process of claim 36 , wherein said further drying occurs under reduced pressure.

40 . The process of claim 36 , wherein said further drying occurs at a humidity below about 30% relative humidity.

41 . The process of claim 29 , wherein the delafloxacin meglumine comprises delafloxacin meglumine trihydrate.

42 . The process of claim 29 , wherein the delafloxacin meglumine comprises delafloxacin meglumine anhydrate.

43 . The process of claim 29 , wherein the delafloxacin meglumine comprises a mixture of delafloxacin meglumine trihydrate and delafloxacin meglumine anhydrate.

44 . A crystalline anhydrous Form 1A of 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-quinolinecarboyxlate prepared according to the method of any one of claims 1 to 19 .

45 . A crystalline anhydrous Form 1B of 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-quinolinecarboyxlate prepared according to the method of any one of claims 20 to 28 .

46 . A crystalline anhydrous Form 1A of 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-quinolinecarboyxlate prepared according to the method of any one of claims 29 to 43 .

47 . A method of treating a bacterial infection in a fish or mammal in need thereof, the method comprising administering to the fish or mammal a therapeutically effective amount of a composition comprising the crystalline form of any one of claims 44 to 46 .

48 . The method of claim 47 , wherein the composition is administered to a mammal.

49 . The method of any one of claims 47 to 48 , wherein the therapeutically effective amount is from about 0.03 to about 200 mg/kg body weight.