Salts of indoleamine 2,3-dioxygenase inhibitors
Provided herein are compounds, salts, crystalline forms, and pharmaceutical compositions that are related to IDO inhibitors, in particular, Compound 1,1-(5-((4-chlorophenyl)amino)-6-(ethyl(tetrahydro-2H-pyran-4-yl)amino)pyridin-3-yl)cyclobutane-1-carboxylic acid. Also provided are methods of treating a disease or disorder such as a cancer or infectious disease that comprises administering to a subject in need thereof one or more of the compounds or compositions of the present disclosure.
1 . A hydrochloride salt of Compound 1:
which is in a crystalline Form I, characterized by an X-ray powder diffraction (XRPD) pattern having the following peaks: 14.7, 17.5, 19.8, 22.4, 22.9 degrees 2 theta, ±0.2°.
2 . The hydrochloride salt of claim 1 , wherein the crystalline Form I is characterized by an X-ray powder diffraction (XRPD) pattern having the following peaks: 12.7, 14.7, 15.0, 15.9, 17.5, 18.7, 19.8, 20.5, 22.4, 22.9, 24.8, 25.5, 26.2, 28.4, 28.7, 29.0 and 30.1 degrees 2 theta, ±0.2°.
3 . The hydrochloride salt of claim 1 , which is prepared by a process comprising: a) mixing Compound 1 and HCl in a solvent system comprising at least one non-aqueous solvent to form the hydrochloride salt; and b) separating the hydrochloride salt from the solvent system.
4 . The hydrochloride salt of claim 3 , wherein the at least one non-aqueous solvent comprises isopropanol.
5 . The hydrochloride salt of claim 3 , wherein the solvent system is free of a primary alcohol.
6 . The hydrochloride salt of claim 1 , which has a purity by weight and/or by HPLC area of at least 90%.
7 . A pharmaceutical composition comprising the hydrochloride salt of claim 1 , and optionally a pharmaceutically acceptable excipient.
8 . The pharmaceutical composition of claim 7 , which is free of Compound 1 in free acid form.
9 . The pharmaceutical composition of claim 7 , comprising the hydrochloride salt, wherein the pharmaceutical composition is free of Compound 1 in a salt form other than hydrochloride salt.
10 . The pharmaceutical composition of claim 7 , comprising the hydrochloride salt, wherein the pharmaceutical composition is free of hydrochloride salt of Compound 1 in a solid form other than Form I.
11 . The pharmaceutical composition of claim 7 , further comprising hydrochloride salt of Compound 1 in an amorphous form.
12 . The pharmaceutical composition of claim 7 , which is a solid dosage form.