Solid forms of (R)-N-(2-(5-fluoropyridin-3-yl)-8-isopropylpyrazolo[1,5-a] [1,3,5]triazin-4-yl)-2,3,4,9-tetrahydro-1H-carbazol-3-amine as aryl hydrocarbon receptor (AHR) inhibitors

1. A compound selected from the group consisting of Compound 1, Compound 3, Compound 4, Compound 5, Compound 6, and Compound 7:

(1) Compound 1:

(2) Compound 3:

(3) Compound 4:

(4) Compound 5:

(5) Compound 6:

wherein 1≤x≤2; and

(6) Compound 7:

wherein 1≤x≤2.

2. The compound according to claim 1 , wherein the compound is Compound 1:

3. The compound according to claim 1 , wherein the compound is Compound 3:

4. The compound according to claim 1 , wherein the compound is Compound 4:

5. The compound according to claim 1 , wherein the compound is Compound 5:

6. The compound according to claim 1 , wherein the compound is Compound 6:

wherein 1≤x≤2.

7. The compound according to claim 1 , wherein the compound is Compound 7:

wherein 1≤x≤2.

8. A pharmaceutical composition comprising the compound according to claim 1 and a pharmaceutically acceptable carrier, excipient, or vehicle.

9. A method for inhibiting aryl hydrocarbon receptor (AHR) activity in a biological sample, wherein the method comprises contacting the biological sample with the compound according to claim 1 .

10. A method for inhibiting aryl hydrocarbon receptor (AHR) activity in a patient in need thereof, wherein the method comprises administering to the patient a therapeutically effective amount of the compound according to claim 1 .

11. A method for inhibiting aryl hydrocarbon receptor (AHR) activity in a patient in need thereof, wherein the method comprises administering to the patient a therapeutically effective amount of the pharmaceutical composition according to claim 8 .

12. A process for preparing the compound according to claim 1 selected from the group consisting of Compound 1, Compound 3, Compound 4, Compound 5, Compound 6, and Compound 7:

(1) Compound 1:

(2) Compound 3:

(3) Compound 4:

(4) Compound 5:

(5) Compound 6:

wherein 1≤x≤2; and

(6) Compound 7:

wherein 1≤x≤2;

wherein the process comprises the following step:

combining a compound represented by formula A:

with an acid represented by a formula selected from the group consisting of:

thereby forming Compound 1;

thereby forming Compound 3;

thereby forming Compound 4;

thereby forming Compound 5;

thereby forming Compound 6; and

thereby forming Compound 7,

optionally in the presence of a solvent.

13. A crystal form of a compound selected from the group consisting of:

(1) Compound A:

wherein the crystal form is Form B or Form C;

wherein Form B is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 9.5°±0.2° 2θ, 9.8°±0.2° 2θ, and 14.7°±0.2° 2θ; and

wherein Form C is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 6.02°±0.2° 2θ, 8.61°±0.2° 2θ, and 10.29°±0.2° 2θ;

(2) Compound 1:

wherein the crystal form is Form A or Form B;

wherein Form A is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 5.8°±0.2° 2θ, 11.6°±0.2° 2θ, and 18.8°±0.2° 2θ; and

wherein Form B is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 5.6°±0.2° 2θ, 11.2°±0.2° 2θ, and 16.9°±0.2° 2θ;

(3) Compound 3:

wherein the crystal form is Form A or Form B;

wherein Form A is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 5.6°±0.2° 2θ, 11.2°±0.2° 2θ, and 16.9°±0.2° 2θ; and

wherein Form B is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 6.0°±0.2° 2θ, 12.1°±0.2° 2θ, and 18.1°±0.2° 2θ;

(4) Compound 4:

wherein the crystal form is Form A; and

wherein Form A is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 7.5°±0.2° 2θ, 8.4°±0.2° 2θ, and 20.1°±0.2° 2θ;

(5) Compound 5:

wherein the crystal form is Form A; and

wherein Form A is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 6.4°±0.2° 2θ, 7.1°±0.2° 2θ, and 12.7°±0.2° 2θ;

(6) Compound 6:

wherein the crystal form is Form A or Form B;

wherein Form A is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 5.5°±0.2° 2θ, 11.1°±0.2° 2θ, and 18.9°±0.2° 2θ;

wherein Form B is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 6.2°±0.2° 2θ, 6.8°±0.2° 2θ, and 13.5°±0.2° 2θ; and

wherein 1≤x≤2; and

(7) Compound 7:

wherein the crystal form is Form A;

wherein Form A is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 6.6°±0.2° 2θ, 10.4°±0.2° 2θ, and 13.2°±0.2° 2θ; and

wherein 1≤x≤2.

14. The crystal form according to claim 13 , wherein the crystal form is of Compound A:

wherein the crystal form is Form B or Form C;

wherein Form B is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 9.5°±0.2° 2θ, 9.8°±0.2° 2θ, and 14.7°±0.2° 2θ; and

wherein Form C is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 6.02°±0.2° 2θ, 8.61°±0.2° 2θ, and 10.29°±0.2° 2θ.

15. The crystal form according to claim 13 , wherein the crystal form is of Compound 1:

wherein the crystal form is Form A or Form B;

wherein Form A is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 5.8°±0.2° 2θ, 11.6°±0.2° 2θ, and 18.8°±0.2° 2θ; and

wherein Form B is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 5.6°±0.2° 2θ, 11.2°±0.2° 2θ, and 16.9°±0.2° 2θ.

16. The crystal form according to claim 13 , wherein the crystal form is of Compound 3:

wherein the crystal form is Form A or Form B;

wherein Form A is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 5.6°±0.2° 2θ, 11.2°±0.2° 2θ, and 16.9°±0.2° 2θ; and

wherein Form B is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 6.0°±0.2° 2θ, 12.1°±0.2° 2θ, and 18.1°±0.2° 2θ.

17. The crystal form according to claim 13 , wherein the crystal form is of Compound 4:

wherein the crystal form is Form A; and

wherein Form A is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 7.5°±0.2° 2θ, 8.4°±0.2° 2θ, and 20.1°±0.2° 2θ.

18. The crystal form according to claim 13 , wherein the crystal form is of Compound 5:

wherein the crystal form is Form A; and

wherein Form A is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 6.4°±0.2° 2θ, 7.1°±0.2° 2θ, and 12.7°±0.2° 2θ.

19. The crystal form according to claim 13 , wherein the crystal form is of Compound 6:

wherein the crystal form is Form A or Form B;

wherein Form A is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 5.5°±0.2° 2θ, 11.1°±0.2° 2θ, and 18.9°±0.2° 2θ;

wherein Form B is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 6.2°±0.2° 2θ, 6.8°±0.2° 2θ, and 13.5°±0.2° 2θ; and

wherein 1≤x≤2.

20. The crystal form according to claim 13 , wherein the crystal form is of Compound 7:

wherein the crystal form is Form A;

wherein Form A is characterized by an X-ray powder diffraction pattern comprising at least one characteristic peak at an angle (°2θ) selected from the group consisting of 6.6°±0.2° 2θ, 10.4°±0.2° 2θ, and 13.2°±0.2° 2θ; and

wherein 1≤x≤2.

21. A pharmaceutical composition comprising the crystal form according to claim 13 and a pharmaceutically acceptable carrier, excipient, or vehicle.

22. A method for inhibiting aryl hydrocarbon receptor (AHR) activity in a biological sample, wherein the method comprises contacting the biological sample with the crystal form according to claim 13 .

23. A method for inhibiting aryl hydrocarbon receptor (AHR) activity in a patient in need thereof, wherein the method comprises administering to the patient a therapeutically effective amount of the crystal form according to claim 13 .

24. A method for inhibiting aryl hydrocarbon receptor (AHR) activity in a patient in need thereof, wherein the method comprises administering to the patient a therapeutically effective amount of the pharmaceutical composition according to claim 21 .