Sorbitol/dexlansoprazole co-crystals and method for making same

1. A crystal comprising: dexlansoprazole and sorbitol, wherein the crystal is a co-crystal or a salt thereof of dexlansoprazole and sorbitol and is substantially crystalline in structure.

2. The crystal of claim 1 , wherein the dexlansoprazole and the sorbitol are present at about a 1:1 molar ratio.

3. The crystal of claim 1 , wherein the dexlansoprazole and the sorbitol are present at about a 1:1.5 molar ratio.

4. The crystal of claim 1 , wherein the crystal has a differential scanning calorimetry (DSC) pattern substantially as set forth in FIG. 12 or FIG. 28 .

5. The crystal of claim 1 , wherein the crystal has a dynamic vapor sorption (DVS) pattern substantially as set forth in FIG. 13 , FIG. 30 a or FIG. 30 b.

6. The crystal of claim 1 , wherein the crystal has an X-ray powder diffraction (XRPD) pattern substantially as set forth in FIG. 15 or FIG. 22 .

7. The crystal of claim 1 , wherein the crystal has a Raman spectrum substantially as set forth in FIG. 14 or FIG. 29 .

8. The crystal of claim 1 , wherein the crystal has an 1 H-NMR spectrum substantially as set forth in FIG. 10 or FIG. 18 .

9. The crystal of claim 1 , wherein the dexlansoprazole and the sorbitol are at least about 90 mole percent of the crystal.

10. A method for making a co-crystal or salt thereof, comprising the steps of:

a) mixing dexlansoprazole and sorbitol in an amount of one or more solvents effective to yield a substantially homogeneously dispersed solution and

b) evaporating the one or more solvents from the solution.

11. The method of claim 10 , wherein the dexlansoprazole and the sorbitol are mixed in about a 1:1 molar ratio or about a 1:1.5 molar ratio.

12. The method of claim 10 , wherein the solution is evaporated under nitrogen.

13. The method of claim 10 , wherein the solution is evaporated at an ambient temperature.

14. The method of claim 10 , wherein the solution is mechanically agitated for at least about 24 hours after mixing and prior to evaporation of the solvent.

15. A method for making a co-crystal or salt thereof, comprising the steps of:

a) dissolving sorbitol in one or more solvents to form a sorbitol solution;

b) adjusting temperature of the sorbitol solution to about 40° C.;

c) dissolving dexlansoprazole in one or more solvents to form a dexlansoprazole solution;

d) adding the dexlansoprazole solution to the sorbitol solution to form a mixture at a temperature ranging from about 40° C. to about 45° C.;

e) cooling the mixture to a temperature ranging from about 2° C. to about 10° C.;

f) stirring the mixture at a temperature ranging from about 2° C. to about 10° C. for a period of time ranging from about 30 minutes to about 25 hours; and

g) recovering the co-crystal or salt thereof which precipitates from the mixture in step (f).

16. The method of claim 15 , wherein the one or more solvents comprise ethanol (EtOH), DMSO, ethyl acetate (EtOAc), tetrahydrofuran (THF), acrylonitrile (MeCN), acetonitrile, methanol (MeOH), tert-butyl methyl ether (TBME) or combination thereof.

17. The method of claim 15 , wherein the one or more solvents comprise DMSO/EtOH (1:5, v/v).

18. The method of claim 15 , wherein step (e) is carried out at a cooling rate ranging from about 0.1 K/min to about 0.2 K/min.

19. The method of claim 15 , wherein seeding crystals in a suspension are added to the mixture before step (e).

20. The method of claim 15 , wherein the co-crystal or salt thereof is recovered by vacuum filtration in step (g).

21. The method of claim 15 , wherein step (a) is carried out at an ambient temperature.

22. The method of claim 15 , wherein step (a) is carried out at an ambient temperature followed by heating to a temperature ranging from about 40° C. to about 60° C.

23. The method of claim 15 , wherein step (c) is carried out before or concurrently with step (b) or step (a).