Nilotinib salts and crystalline forms thereof
AssigneeTeva Pharmaceutical Industries Ltd.
InventorsMaytal Piran, Jacob Rendell
Life of this patent
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Abstract
Nilotinib salts and crystalline forms thereof have been prepared and characterized.
Claims34
A crystalline form of Nilotinib hydrochloride selected from the group consisting of
- a) crystalline form T20 of Nilotinib hydrochloride characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 5.3, 7.0, 14.4, 20.1, and 21.1 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 1;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 2;
- and combinations thereof;
- b) crystalline form T27 of Nilotinib hydrochloride characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 6.8, 11.8, 12.6, 13.7, and 25.3 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 68;
- and combinations thereof;
- c) crystalline form T28 of Nilotinib hydrochloride characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 4.2, 8.5, 11.3, 12.8, and 16.0 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 69;
- and combinations thereof;
- and
- d) crystalline form T29 of Nilotinib hydrochloride characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 6.0, 6.4, 8.9, 19.7, and 20.6 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 70;
- and combinations thereof.
A crystalline form of Nilotinib fumarate selected from the group consisting of
- a) crystalline form I of Nilotinib fumarate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 4.8, 8.9, 16.2, 18.5, and 19.7 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 5;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 6;
- and combinations thereof;
- and
- b) crystalline form II of Nilotinib fumarate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 4.2, 8.4, 10.0, 17.1 and 19.3 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 7;
- and combinations thereof.
A crystalline form of Nilotinib 2-chloro-mandelate that is crystalline form I of Nilotinib 2-chloro-mandelate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 14.8, 16.2, 17.6, 18.5, and 19.6 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 8;
- and combinations thereof.
A crystalline form of Nilotinib adipate that is crystalline form I of Nilotinib adipate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 5.3, 7.6, 10.5, 18.6, and 19.8 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 13;
- and combinations thereof.
A crystalline form of Nilotinib glutarate selected from the group consisting of
- a) crystalline form I of Nilotinib glutarate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 4.9, 7.5, 11.5, 20.8, and 21.7 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 17;
- and combinations thereof;
- b) crystalline form II of Nilotinib glutarate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 4.9, 7.5, 21.4, 25.0, and 25.6 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 18;
- and combinations thereof;
- and
- c) crystalline form III of Nilotinib glutarate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 12.0, 19.0, 21.6, and 22.5 degrees two theta ±0.2 degrees two theta;
- and a broad peak having a maximum at 6.7 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 19;
- and combinations thereof.
A crystalline form of Nilotinib p-toluenesulfonate selected from the group consisting of
- a) crystalline form I of Nilotinib p-toluenesulfonate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having with broad peaks having maxima at 4.9, 7.0, 18.5, and 25.7 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 20;
- and combinations thereof;
- and
- b) crystalline form II of Nilotinib p-toluenesulfonate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 5.0, 14.6, 18.3, and 27.0 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 21;
- and combinations thereof.
A crystalline form of Nilotinib camphorsulfonate that is crystalline form I of Nilotinib camphorsulfonate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 3.0, 5.4, and 6.2 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 22;
- and combinations thereof.
A crystalline form of Nilotinib palmitate that is crystalline form I of Nilotinib palmitate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 2.1, 4.1, 6.2, 10.4, and 14.6 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 25;
- and combinations thereof.
A crystalline form of Nilotinib quinate that is crystalline form I of Nilotinib quinate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 4.9, 7.6, 10.0, 11.5, and 20.0 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 26;
- and combinations thereof.
A crystalline form of Nilotinib citrate that is crystalline form I of Nilotinib citrate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 4.4, 5.2, 7.5, 11.2, and 15.3 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 27;
- and combinations thereof.
A crystalline form of Nilotinib L-aspartate selected from the group consisting of
- a) crystalline form I of Nilotinib L-aspartate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 4.4, 5.4, 9.0, and 18.0 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 46;
- and combinations thereof;
- b) crystalline form II of Nilotinib L-aspartate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 5.3, 7.8, 10.9, 19.3, and 25.1 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 47;
- and combinations thereof;
- and
- c) crystalline form III of Nilotinib L-aspartate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 7.2, 8.6, 13.7, 14.5, and 20.9 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 48;
- and combinations thereof.
A crystalline form of Nilotinib malonate that is crystalline form I of Nilotinib malonate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 6.2, 16.9, 18.0, 19.9, and 24.0 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 59;
- and combinations thereof.
A crystalline form of Nilotinib oxalate that is crystalline form I of Nilotinib oxalate characterized by data selected from the group consisting of:
- an X-ray powder diffraction pattern having peaks at 8.3, 10.0, 13.6, 16.5, and 23.3 degrees two theta ±0.2 degrees two theta;
- an X-ray powder diffraction pattern substantially as depicted in FIG. 63;
- and combinations thereof.
Dependencies are inferred from the claim text.