Lyophilized pharmaceutical compositions

A method of treating a condition, the method comprising administering to a subject in need thereof a therapeutically effective amount of a T-cell activating agent and a therapeutically effective amount of a pharmaceutical composition prepared by a process, wherein the process comprises:

• (a) dissolving a compound of formula (1):
• or a pharmaceutically-acceptable salt thereof, in a solvent comprising dimethylsulfoxide (DMSO) to form a solution, wherein the solvent is then removed by a freeze-drying process to give the lyophilized pharmaceutical product, wherein the freeze-drying process comprises:
• (i) a first freezing stage in which the solution is frozen by reducing the temperature thereof to a temperature of no greater than about −20° C.;
• (ii) a first warming stage in which the temperature of the frozen solution is raised to a temperature in the range from about −15° C. to about 5° C., wherein the temperature in the range from about −15° C. to about 5° C. keeps the solution frozen;
• (iii) a second freezing stage in which the temperature of the solution is lowered to a temperature of no greater than about −20° C.;
• (iv) a primary drying stage, wherein the primary drying stage comprises a sublimation step in which the DMSO is removed by sublimation from the solution in its frozen state under reduced pressure to give a partially dried product, wherein the reduced pressure in the primary drying stage is from about 5 μBar to about 40 μBar;
• and
• (v) a secondary drying stage in which the DMSO is removed by evaporation from the partially dried product in a non-frozen state under reduced pressure to give the lyophilized pharmaceutical product, and
• (b) reconstituting the lyophilized pharmaceutical product in a substantially anhydrous solvent to give the pharmaceutical composition.

A method of preparing a pharmaceutical composition, the method comprising:

• (a) dissolving a compound of formula (1):
• or a pharmaceutically-acceptable salt thereof, in a solvent comprising dimethyl sulfoxide (DMSO) to form a solution;
• (b) removing the solvent by a freeze-drying process to give a lyophilized product;
• and
• (c) reconstituting the lyophilized product in a substantially anhydrous solvent to give the pharmaceutical composition, wherein the substantially anhydrous solvent comprises 45% to 85% (v/v) propylene glycol, 5% to 45% (v/v) glycerin, and 0% to 30% (v/v) ethanol.