Granted Patent B2

US 12,590,118 · App. 17/597,919 · Granted Mar 31, 2026

Inventors: Zongbin Li (Shanghai, CN); Yuanzhuo Kuang (Shanghai, CN); Linsong Guo (Shanghai, CN)

Assignees: Shanghai Hansoh Biomedical Co., Ltd.; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.

C07J43/003C07B2200/13

Abstract

Claims (41)

1 . A crystal form of formula (VI), having the following structure:

wherein x is 0, the crystal form is crystal form I of free base, the X-ray powder diffraction pattern thereof has any 3 to 11 of the diffraction peaks at 2θ (±0.2°) of 16.7, 12.6, 17.4, 7.3, 20.2, 20.6, 11.9, 11.1, 23.9, 21.9 and 38

or,

wherein x is 0, the crystal form is crystal form II of free base, the X-ray powder diffraction pattern thereof has diffraction peaks at 2θ (±0.2°) of 11.7, 13.4, 13.6, 16.6 and 18.9;

or,

wherein x is 0, the crystal form is crystal form III of free base, the X-ray powder diffraction pattern thereof has diffraction peaks at 2θ (±0.2°) of 10.0, 11.7, 13.7, 16.6, 18.9 and 19.2:

or,

wherein M is methanesulfonic acid, x is 1, the X-ray powder diffraction pattern thereof has diffraction peaks at 2θ (±0.2°) of 12.5, 13.5, 194 and 19.9.

2 . The crystal form according to claim 1 , wherein,

the DSC spectrum of the crystal form I of free base has an endothermic peak at 151.4±0.5° C.;

or, the DSC spectrum of the crystal form II of free base has an endothermic peak at 193.5±0.5° C.;

or, the DSC spectrum of the crystal form III of free base has an endothermic peak at 206.4±0.5° C.

3 . The crystal form according to claim 1 , wherein the crystal form is crystal form I of free base and the X-ray powder diffraction pattern of the crystal form comprises any 5 to 8 or 6 to 8 of the diffraction peaks.

4 . The crystal form according to claim 1 , wherein the crystal form is crystal form I of free base and the X-ray powder diffraction pattern of the crystal form comprises any 3, 6, 8, 10 or 11 of the diffraction peaks.

5 . The crystal form according to claim 1 , wherein

the crystal form is crystal form I of free base and the X-ray powder diffraction pattern of the crystal form has diffraction peaks at 2θ (±0.2°) of 16.7, 12.6 and 17.4;

the crystal form is crystal form II of free base and the X-ray powder diffraction pattern further has diffraction peaks at 2θ (±0.2°) of 9.5, 10.1, 14.7 and 19.3;

the crystal form is crystal form III of free base and the X-ray powder diffraction pattern further has diffraction peaks at 2θ (±0.2°) of 13.4, 19.6, 20.6, 20.9, 22.0, 22.7, 23.4 and 25.6;

or

the X-ray powder diffraction pattern of the methanesulfonic acid crystal form further has diffraction peaks at 2θ (±0.2°) of 15.1, 15.8, 16.5, 17.3, 18.7 and 23.1.

6 . The crystal form according to claim 5 , wherein

the crystal form is crystal form I of free base and the X-ray powder diffraction pattern of the crystal form further comprises one or more diffraction peaks at 2θ (±0.2°) of 7.3, 20.2, 20.6, 11.9, 11.1, 23.9, 21.9 and 38.4;

the crystal form is crystal form II of free base and the X-ray powder diffraction pattern further has diffraction peaks at 2θ (±0.2°) of 19.6, 20.6, 20.9, 21.6, 22.1, 22.5, 22.7 and 24.4;

or

the crystal form is crystal form of methanesulfonic acid and the X-ray powder diffraction pattern further has diffraction peaks at 2θ (±0.2°) of 11.1, 11.5, 13.9, 18.5, 213, 21.7, 26.5 and 28.9.

7 . The crystal form according to claim 1 , wherein the crystal form is crystal form I of free base and the X-ray powder diffraction pattern of the crystal form has diffraction peaks at 2θ (±0.2°) of 16.7, 12.6, 17.4, 7.3, 20.2 and 20.6.

8 . The crystal form according to claim 1 , wherein the crystal form is crystal form I of free base and the X-ray powder diffraction pattern of the crystal form has diffraction peaks at 2θ (±0.2°) of 16.7, 12.6, 17.4, 73, 20.2, 20.6, 11.9 and 11.1.

9 . The crystal form according to claim 1 , wherein the crystal form is crystal form I of free base and the X-ray powder diffraction pattern of the crystal form has diffraction peaks at 2θ (±0.2°) of 16.7, 12.6, 17.4, 7.3, 20.2, 20.6, 11.9, 11.1, 23.9 and 21.9.

10 . The crystal form according to claim 1 , wherein the crystal form is crystal form I of free base, and the X-ray powder diffraction pattern of the crystal form has diffraction peaks at 2θ (±0.2°) of 16.7, 12.6, 17.4, 7.3, 20.2, 20.6, 11.9, 11.1, 23.9, 21.9 and 38.4.

11 . The crystal form according to claim 1 , wherein

the crystal form is crystal form I of free base and the X-ray powder diffraction pattern of the crystal form is substantially as shown in FIG. 1 ;

the crystal form is crystal form II of free base and the X-ray powder diffraction pattern thereof is substantially as shown in FIG. 3 ;

the crystal form is crystal form III of free base and the X-ray powder diffraction pattern thereof is substantially as shown in FIG. 5 ; or

the crystal form is crystal form of methanesulfonic acid and the X-ray powder diffraction pattern thereof is substantially as shown in FIG. 7 .

12 . A pharmaceutical composition, comprising a therapeutically effective amount of the crystal form of the compound of formula (VI) according to claim 1 , and one or more pharmaceutically acceptable carriers.

13 . A crystal form of a compound of formula (VI), having the following structure,

wherein

x is 0, the crystal form is crystal form I of free base and the X-ray powder diffraction pattern thereof has diffraction peaks at 2θ (±0.2°) of 16.7, 12.6 and 14.6;

the crystal form I of free base has diffraction peaks at 2θ (±0.2°) of 7.3, 13.2, 17.4, 19.4, 20.2 and 20.6; or

the crystal form I of free base has diffraction peaks at 2θ (±0.2°) of 9.2, 11.1, 11.9, 19.6, 22.3 and 25.5.

14 . A pharmaceutical composition, comprising a therapeutically effective amount of the crystal form of the compound of formula (VI) according to claim 13 , and one or more pharmaceutically acceptable carriers.

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (22)