Crystalline bromodomain inhibitors

An isolated crystalline form of N-[4-(2,4-difluorophenoxy)-3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl]ethanesulfonamide, wherein the crystalline form has a powder X-ray diffraction pattern comprising the following 2θ peak values ±0.2:

• 6.2°, 9.0°, 11.0°, 12.3°, 12.6°, 13.1°, 14.1°, 15.6°, 16.4°, 16.5°, 16.9°, 17.8°, 18.1°, 18.3°, 18.9°, 20.4°, 21.1°, 21.6°, 21.8°, 22.1°, 22.9°, 23.2°, 24.4°, 24.7°, 25.6°, 26.3°, 27.0°, and 27.3°.

A method of making a pharmaceutical composition comprising N-[4-(2,4-difluorophenoxy)-3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl]ethanesulfonamide and a pharmaceutically acceptable carrier, comprising:

• mixing an isolated crystalline form of N-[4-(2,4-difluorophenoxy)-3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl]ethanesulfonamide, wherein the crystalline form has a powder X-ray diffraction pattern comprising three or more 2θ peak values ±0.2 selected from the group consisting of:
• 6.2°, 9.0°, 12.3°, 12.6°, 15.6°, 22.1°, 25.6°, 26.3°, 27.0°, and 27.3°, with a pharmaceutically acceptable carrier.

A composition comprising greater than 90% (w/w) crystalline form II of N-[4-(2,4-difluorophenoxy)-3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl]ethanesulfonamide, wherein the crystalline form has a powder X-ray diffraction pattern comprising three or more 2θ peak values ±0.2 selected from the group consisting of:

• 6.2°, 9.0°, 12.3°, 12.6°, 15.6°, 22.1°, 25.6°, 26.3°, 27.0°, and 27.3°.