Granted Patent B2

US 12,606,527 · App. 18/772,244 · Granted Apr 21, 2026

Inventors: Christian Bacilieri (Breganzona, CH); Gionata Frasca (Minusio, CH)

Assignee: Helsinn Healthcare SA

C07D213/75

Abstract

Claims (18)

1 . A method of making a liquid dosage form comprising mixing a crystalline micronized free-base form of the compound 2-(3,5-bis(trifluoromethyl)phenyl)-N,2-dimethyl-N-(6-(4-methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)propenamide and one or more liquid pharmaceutical excipients, wherein the compound has an X-ray powder diffraction pattern comprising one or more characteristic peaks in terms of 2θ at 4.5°±0.2°; 8.4°±0.2°; 11.5°±0.2°; 13.1°±0.2°; 13.9°±0.2°; 14.8°±0.2°; 16.7°±0.2°; 17.4°±0.2°; 17.7°±0.2°; 19.5°±0.2°; 21.2°±0.2°; 21.6°±0.2°; or 21.8°±0.2°.

2 . The method of claim 1 wherein the compound has an X-ray powder diffraction pattern comprising four or more characteristic peaks in terms of 2θ at 4.5°±0.2°; 8.4°±0.2°; 11.5°±0.2°; 13.1°±0.2°; 13.9°±0.2°; 14.8°±0.2°; 16.7°±0.2°; 17.4°±0.2°; 17.7°±0.2°; 19.5°±0.2°; 21.2°±0.2°; 21.6°±0.2°; or 21.8°±0.2°.

3 . The method of claim 1 wherein the compound has an X-ray powder diffraction pattern comprising the following characteristic peaks in terms of 2θ at 4.5°±0.2°; 8.4°±0.2°; 11.5°±0.2°; 13.1°±0.2°; 13.9°±0.2°; 14.8°±0.2°; 16.7°±0.2°; 17.4°±0.2°; 17.7°±0.2°; 19.5°±0.2°; 21.2°±0.2°; 21.6°±0.2°; or 21.8°±0.2°.

4 . The method of claim 1 wherein the compound has an X-ray powder diffraction pattern comprising one or more characteristic peaks in terms of 2θ at 4.5°±0.2°, 11.5°±0.2°, or 13.1°±0.2°.

5 . The method of claim 1 wherein the compound has an X-ray powder diffraction pattern comprising the following characteristic peaks in terms of 2θ at 4.5°±0.2°, 11.5°±0.2°, or 13.1°±0.2°.

6 . The method of claim 1 wherein the compound has an X-ray powder diffraction pattern comprising a characteristic peak in terms of 2θ at 4.5°±0.2°.

7 . The method of claim 1 wherein the compound has an X-ray powder diffraction pattern comprising a characteristic peak in terms of 2θ at 11.5°±0.2°.

8 . The method of claim 1 wherein the compound has an X-ray powder diffraction pattern comprising a characteristic peak in terms of 13.1°±0.2°.

9 . The method of claim 1 wherein the compound comprises less than 1% impurities.

10 . The method of claim 1 , wherein the compound lacks amorphous character.

11 . The method of claim 1 wherein the compound has a triclinic crystal system.

12 . The method of claim 1 wherein the compound has a needle-like crystal habit.

13 . The method of claim 1 wherein the compound has a melting temperature (T onset ) of about 159.5° C.

14 . The method of claim 1 wherein the compound is anhydrous.

15 . The method of claim 1 wherein the compound is non-solvated.

16 . The method of claim 1 wherein the compound is in the form of particles in which 90% of the particles are greater than 0.01 microns and less than 500 microns.

17 . The method of claim 1 wherein the compound is in the form of particles in which 90% of the particles are greater than 0.1 microns and less than 100 microns.

18 . The method of claim 1 wherein the liquid dosage form is an injectable solution.

Continuity (7)

References Cited (21)