4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid salt crystal forms

1. A 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid addition salt crystal form, wherein said salt crystal form exhibits an X-ray powder diffraction pattern comprising at least two peaks selected from the group consisting of 5.68°, 12.11°, 16.04°, 17.03°, 18.16°, 19.00°, 21.67°, 22.55°, 23.48° and 24.30°±0.2° 2θ.

2. A pharmaceutical composition comprising the salt crystal form according to claim 1 , as active ingredient, together with a pharmaceutically acceptable diluent or carrier.

3. The salt crystal form according to claim 1, wherein the X-ray powder diffraction data is collected on a diffractometer operating with a copper anode with a nickel filter.

4. The salt crystal form according to claim 1, wherein said salt crystal form exhibits an X-ray powder diffraction pattern comprising at least three peaks selected from the group consisting of 5.68°, 12.11°, 16.04°, 17.03°, 18.16°, 19.00°, 21.67°, 22.55°, 23.48° and 24.30°, ±0.2° 2θ, wherein the X-ray powder diffraction data is collected on a diffractometer operating with a copper anode with a nickel filter.

5. The salt crystal form according to claim 1, wherein said salt crystal form exhibits an X-ray powder diffraction pattern comprising at least four peaks selected from the group consisting of 5.68°, 12.11°, 16.04°, 17.03°, 18.16°, 19.00°, 21.67°, 22.55°, 23.48° and 24.30°, ±0.2° 2θ, wherein the X-ray powder diffraction data is collected on a diffractometer operating with a copper anode with a nickel filter.

6. The salt crystal form according to claim 1, wherein said salt crystal form exhibits an X-ray powder diffraction pattern comprising at least five peaks selected from the group consisting of 5.68°, 12.11°, 16.04°, 17.03°, 18.16°, 19.00°, 21.67°, 22.55°, 23.48° and 24.30°, ±0.2° 2θ, wherein the X-ray powder diffraction data is collected on a diffractometer operating with a copper anode with a nickel filter.

7. The salt crystal form according to claim 1, wherein said salt crystal form exhibits an X-ray powder diffraction pattern comprising at least two peaks having D-spacing values selected from the group consisting of 15.543Å, 7.303Å, 5.520Å, 5.202Å, 4.882Å, 4.668Å, 4.097Å, 3.940Å, 3.786Å and 3.660Å, wherein the X-ray powder diffraction data is collected on a diffractometer operating with a copper anode with a nickel filter.

8. The salt crystal form according to claim 1, wherein said salt crystal form exhibits an X-ray powder diffraction pattern comprising at least five peaks having D-spacing values selected from the group consisting of 15.543Å, 7.303Å, 5.520Å, 5.202Å, 4.882Å, 4.668Å, 4.097Å, 3.940Å, 3.786Å and 3.660Å, wherein the X-ray powder diffraction data is collected on a diffractometer operating with a copper anode with a nickel filter.

9. The salt crystal form according to claim 1, wherein said salt crystal form exhibits a differential scanning calorimetry pattern comprising a peak temperature range of 180° C. to 181° C.

10. A pharmaceutical composition comprising the salt crystal form according to claim 3, as active ingredient, together with a pharmaceutically acceptable diluent or carrier.

11. A pharmaceutical composition comprising the salt crystal form according to claim 6, as active ingredient, together with a pharmaceutically acceptable diluent or carrier.

12. A pharmaceutical composition comprising the salt crystal form according to claim 7, as active ingredient, together with a pharmaceutically acceptable diluent or carrier.

13. A pharmaceutical composition comprising the salt crystal form according to claim 8, as active ingredient, together with a pharmaceutically acceptable diluent or carrier.

14. A pharmaceutical composition comprising the salt crystal form according to claim 9, as active ingredient, together with a pharmaceutically acceptable diluent or carrier.

15. The pharmaceutical composition according to claim 10, wherein the composition comprises up to 10% by weight of other crystal forms of 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′: 4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid addition salt.

16. The pharmaceutical composition according to claim 10, wherein the composition comprises up to 10% by weight of amorphous forms of 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′: 4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid addition salt.

17. A 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′: 4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid addition salt crystal form, wherein said salt crystal form is in triclinic, monoclinic, orthorhombic, tetragonal, rhombohedral, hexagonal or cubic crystal form.

18. The salt crystal form according to claim 17, wherein the salt crystal form exists as flakes or needles.

19. A method of manufacturing a pharmaceutical composition comprising 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′: 4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid addition salt, wherein the method comprises the step of combining the salt crystal form according to claim 1 with at least one pharmaceutically acceptable diluent or carrier.

20. The method according to claim 19, wherein the 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′: 4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid addition salt is the active ingredient of the pharmaceutical composition.

21. The method according to claim 19, wherein the 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′: 4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid addition salt consists of 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′: 4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone free base and toluenesulfonic acid in a 1:1 molar ratio.

22. A method of manufacturing a pharmaceutical composition comprising 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′: 4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid addition salt, wherein the method comprises the step of combining the salt crystal form according to claim 3 with at least one pharmaceutically acceptable diluent or carrier.

23. A method of manufacturing a pharmaceutical composition comprising 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′: 4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid addition salt, wherein the method comprises the step of combining the salt crystal form according to claim 6 with at least one pharmaceutically acceptable diluent or carrier.