Nilotinib salts and crystalline forms thereof

A crystalline form of Nilotinib hydrobromide selected from:

• a) Nilotinib hydrobromide form I, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 4.8, 6.8, 9.0, 9.6 and 13.6 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 51, and combinations thereof;
• b) Nilotinib hydrobromide form II, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 17.3, 21.5, 24.5 and 26.5 degrees two theta±0.2 degrees two theta and a broad peak having a maximum at 20.8 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 52, and combinations thereof;
• c) Nilotinib hydrobromide form III, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 6.5, 8.5, 12.3, 19.5 and 20.6 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 53, and combinations thereof;
• d) Nilotinib hydrobromide form IV, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 4.7, 9.3, 11.3, 14.0 and 20.2 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 54, and combinations thereof;
• e) Nilotinib hydrobromide form V, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 7.4, 9.4, 12.0, 14.8 and 16.0 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 55, and combinations thereof;
• f) Nilotinib hydrobromide form VI, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 2.9, 11.8, 12.8, 18.4 and 22.3 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 56, and combinations thereof;
• g) Nilotinib hydrobromide form VII, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 8.1, 12.2, 13.8, 16.3 and 23.3 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 58, and combinations thereof;
• h) Nilotinib hydrobromide form VIII, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 8.5, 17.0, 19.2, 20.6 and 21.8 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 64, and combinations thereof;
• i) Nilotinib hydrobromide form IX, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 16.9, 18.7, 20.9, 21.8 and 26.7 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 65, and combinations thereof;
• j) Nilotinib hydrobromide form X, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 8.8, 15.5, 18.6, 22.2 and 24.2 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 66, and combinations thereof;
• and
• k) Nilotinib hydrobromide form XI, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 7.1, 14.1, 18.6, 21.9 and 22.5 degrees two theta±0.2 degrees two theta;
• an X-ray powder diffraction pattern substantially as depicted in FIG. 67, a solid state 13C NMR spectrum having signals at 129.8, 132.3 and 160.5±0.2 ppm, a solid-state 13C NMR spectrum having chemical shift differences between the signal exhibiting the lowest chemical shift in the chemical shift range of 100 to 180 ppm and another in the chemical shift range of 100 to 180 ppm of 23.0, 25.5 and 53.7±0.1 ppm, a solid state 13C NMR spectrum as depicted in any one of FIGS. 73-74, and combinations thereof.

A crystalline form of Nilotinib succinate selected from:

• a) Nilotinib succinate Form I, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 4.5, 7.6, 11.3, 17.4 and 18.7 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern having peaks at 4.4, 7.6, 11.3, 17.3 and 18.7 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 10, and combinations thereof;
• b) Nilotinib succinate form II, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 4.8, 9.5, 13.3, 19.2 and 21.0 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 11, and combinations thereof;
• and
• c) Nilotinib succinate form III, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 6.8, 9.0, 10.4, 15.3 and 19.4 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 12, and combinations thereof.

A crystalline form of Nilotinib acetate selected from:

• a) Nilotinib acetate form I, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 5.4, 7.6, 8.8 degrees two theta±0.2 degrees two theta and broad peaks having maxima at 18.4 and 24.5 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 37, and combinations thereof;
• b) Nilotinib acetate form II, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 7.2, 7.8, 8.6, 10.9 and 13.6 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 38, and combinations thereof;
• c) Nilotinib acetate form III, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 3.6, 6.7, 10.0, 15.8 and 21.2 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 39, and combinations thereof;
• d) Nilotinib acetate form IV, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 4.7, 7.1, 9.5 and 14.9 degrees two theta±0.2 degrees two theta and a broad peak having a maximum at 14.1 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 40, and combinations thereof;
• e) Nilotinib acetate form V, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 7.4, 11.3, 14.2, 14.9 and 19.1 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 41, and combinations thereof;
• and
• f) Nilotinib acetate form VI, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 6.4, 10.8, 17.7, 19.0 and 19.7 degrees two theta±0.2 degrees two theta, an X-ray powder diffraction pattern substantially as depicted in FIG. 42, and combinations thereof.

A crystalline form of Nilotinib maleate selected from:

• a) Nilotinib maleate Form I, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 7.5, 11.1, 15.3, 16.9 and 18.6 degrees two theta±0.2 degrees two theta;
• an X-ray powder diffraction pattern substantially as depicted in FIG. 32;
• and combinations thereof;
• b) Nilotinib maleate Form II, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 5.2, 10.4, 15.6, 21.0 and 25.6 degrees two theta±0.2 degrees two theta;
• an X-ray powder diffraction pattern substantially as depicted in FIG. 33;
• and combinations thereof;
• c) Nilotinib maleate Form III, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 7.4, 10.4, 14.9, 16.1 and 18.4 degrees two theta±0.2 degrees two theta;
• an X-ray powder diffraction pattern substantially as depicted in FIG. 34;
• and combinations thereof;
• d) Nilotinib maleate Form IV, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 5.6, 8.3, 10.1, 14.8 and 17.0 degrees two theta±0.2 degrees two theta;
• an X-ray powder diffraction pattern substantially as depicted in FIG. 36;
• and combinations thereof;
• and
• e) Nilotinib maleate Form V, characterized by data selected from:
• an X-ray powder diffraction pattern having peaks at 9.7, 13.5, 16.6, 20.3 and 21.8 degrees two theta±0.2 degrees two theta;
• an X-ray powder diffraction pattern substantially as depicted in FIG. 57;
• and combinations thereof.