Solid forms of 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate

1. A crystalline compound, which is 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate or a salt thereof.

2. The crystalline compound of claim 1 , which is 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate freebase.

3. The crystalline compound of claim 2 , which has a DSC peak at about 177.9° C.

4. The crystalline compound of claim 1 , which is 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate benzoate.

5. The crystalline compound of claim 4 , which has a melting point of about 192.3° C. or a DSC peak at about 194.5° C.

6. The crystalline compound of claim 4 , which has an XRPD spectrum comprising peaks at about 6.5, 15.6, 16.5, 18.4, 19.2, 21.3, and 24.2±0.3 degrees 2θ.

7. The crystalline compound of claim 1 , which is 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate hydrochloride.

8. The crystalline compound of claim 7 , which has a melting point of about 245.8° C. or a DSC peak at about 248.9° C.

9. The crystalline compound of claim 7 , which has an XRPD spectrum comprising peaks at about 6.4, 11.7, 17.0, 19.2, 23.0, and 25.7±0.3 degrees 2θ.

10. The crystalline compound of claim 1 , which is 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate phosphate.

11. The crystalline compound of claim 10 , which has a melting point of about 164.6° C. or a DSC peak at about 170.9° C.

12. The crystalline compound of claim 10 , which has an XRPD spectrum comprising peaks at about 4.5, 12.9, 16.0, 18.5, 20.3, 21.4, and 23.0±0.3 degrees 2θ.

13. A pharmaceutical formulation comprising the crystalline compound of claim 1 and a pharmaceutically acceptable excipient.

14. A method of preparing a crystalline salt of 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate, which comprises:

heating a solution comprising 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate and a pharmaceutically acceptable acid to provide a salt of 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate;

reducing the solubility of the salt in the solution under conditions sufficient to provide a crystalline salt of 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate; and

isolating the crystalline salt.

15. A method of preparing crystalline 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate hydrochloride, which comprises:

heating a solution comprising water, 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate, and p-toluenesulfonic acid monohydrate;

adding an anti-solvent to the solution to provide a mixture;

cooling the mixture; and

isolating crystalline 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate hydrochloride from the mixture.

16. The method of claim 15 , wherein the anti-solvent is acetonitrile.

17. A method of lowering intraocular pressure in a patient, which comprises administering the pharmaceutical formulation of claim 13 to the eye of a patient.