Granted Patent B2

US 12,295,950 · App. 17/973,362 · Granted May 13, 2025

Inventor: Lixin Li (Beijing, CN)

Assignee: Birdie Biopharmaceuticals, Inc.

A61K31/4745C07D471/04

Abstract

Claims (45)

1. A sulfate salt of resiquimod in crystal form, characterized by an x-ray powder diffraction spectrum that comprises peaks at 7 to 8 degrees 2θ, 13.5 to 14.5 degrees 2θ, 19 to 20 degrees 2θ, or 19.5 to 20.5 degrees 2θ, as determined by XRPD using Cu Kα1 and Cu Kα2 radiation.

2. The sulfate salt of resiquimod in crystal form of claim 1 , wherein the sulfate salt of resiquimod is a crystal form having one or more of:

A) an X-ray powder diffractogram substantially as shown in FIG. 7 , as determined by XRPD using Cu Kα1 and Cu Kα2 radiation;

B) a differential scanning calorimetry thermogram comprising an endothermic peak at about 217.1° C.;

C) a differential scanning calorimetry thermogram substantially as shown in FIG. 9 ;

D) a thermogravimetric analysis substantially as shown in FIG. 9 ;

E) an X-ray powder diffractogram substantially as shown in FIG. 50 , as determined by XRPD using Cu Kα1 and Cu Kα2 radiation;

F) a differential scanning calorimetry thermogram comprising an endothermic peak at about 105.3° C., about 219.2° C., or both;

G) a differential scanning calorimetry thermogram substantially as shown in FIG. 51 ; or

H) a thermogravimetric analysis substantially as shown in FIG. 51 .

3. The sulfate salt of resiquimod in crystal form of claim 1 , wherein the x-ray powder diffraction spectrum comprises peaks at 7.6±0.2 degrees 2θ, 11.7±0.2 degrees 2θ, and 18.2±0.2 degrees 2θ, optionally further comprises peaks at 15.5±0.2 degrees 2θ, 17.6 ±0.2 degrees 2θ, and 24.4±0.2 degrees 2θ, and optionally further comprises peaks at 9.6±0.2 degrees 2θ, 13.4±0.2 degrees 2θ, and 23.5±0.2 degrees 2θ, as determined by XRPD using Cu Kα1 and Cu Kα2 radiation.

4. A dosage form, comprising the sulfate salt of resiquimod in crystal form of claim 1 .

5. The dosage form of claim 4 , which is a solid dosage form, a semi-solid dosage form, or a liquid dosage form.

6. A method of treating a cancer in a subject in need thereof, comprising administering the sulfate salt of resiquimod in crystal form of claim 1 to the subject.

7. A method of treating a tumor in a subject in need thereof, comprising administering the sulfate salt of resiquimod in crystal form of claim 1 to the subject.

8. The method of claim 7 , wherein the tumor comprises is a carcinoma, a sarcoma, a blastoma, or a combination thereof.

9. The sulfate salt of resiquimod in crystal form of claim 1 , wherein the sulfate salt of resiquimod in crystal form is a monosulfate salt and is an anhydrate.

10. The sulfate salt of resiquimod in crystal form of claim 9 , wherein the sulfate salt of resiquimod in crystal form is characterized by an X-ray powder diffraction spectrum that exhibits peaks at:

7.6±0.2° 2θ,

11.7±0.2° 2θ,

15.5±0.2° 2θ,

17.6±0.2° 2θ,

18.2±0.2° 2θ; and

24.4±0.2° 2θ.

11. The sulfate salt of resiquimod in crystal form of claim 9 , wherein the sulfate salt of resiquimod in crystal form is characterized by an X-ray powder diffraction spectrum that exhibits peaks at:

7.6±0.2° 2θ,

9.6±0.2° 2θ,

11.7±0.2° 2θ,

13.4±0.2° 2θ,

15.5±0.2° 2θ,

17.6=0.2° 2θ,

18.2±0.2° 2θ;

23.5±0.2° 2θ, and

24.4±0.2° 2θ.

12. A composition comprising the sulfate salt of resiquimod in crystal form of claim 10 and a pharmaceutically acceptable carrier or excipient.

13. A method for preparing a composition comprising combining the sulfate salt of resiquimod in crystal form of claim 10 with a pharmaceutically acceptable carrier or excipient.

14. A composition prepared by the method of claim 13 .

15. A method of treating cancer in a subject in need thereof comprising administering to the subject the composition of claim 12 .

16. The method of claim 15 , wherein the cancer is selected from breast cancer, head and neck cancer, ovarian cancer, uterine cancer, skin cancer, brain cancer, bladder cancer, thyroid cancer, liver cancer, pancreatic cancer, lung cancer, ocular cancer, throat cancer, esophageal cancer, stomach cancer, intestinal cancer, rectal cancer, testicular cancer, ovarian cancer, vaginal cancer, bone cancer, blood cancer, and prostate cancer.

17. A method of treating a tumor in a subject in need thereof comprising administering to the subject the composition of claim 12 .

18. The method of claim 17 , wherein the tumor is a carcinoma, sarcoma or blastoma, or a combination thereof.

19. A method of treating cancer in a subject in need thereof comprising administering to the subject the composition of claim 14 .

20. The method of claim 19 , wherein the cancer is selected from breast cancer, head and neck cancer, ovarian cancer, uterine cancer, skin cancer, brain cancer, bladder cancer, thyroid cancer, liver cancer, pancreatic cancer, lung cancer, ocular cancer, throat cancer, esophageal cancer, stomach cancer, intestinal cancer, rectal cancer, testicular cancer, ovarian cancer, vaginal cancer, bone cancer, blood cancer, and prostate cancer.

21. A method of treating a tumor in a subject in need thereof comprising administering to the subject the composition of claim 14 .

22. The method of claim 21 , wherein the tumor is a carcinoma, sarcoma or blastoma, or a combination thereof.

Assignments (1)

Continuity (2)

References Cited (342)