TYK2 inhibitors, uses, and methods for production thereof
View Patent ↗The present invention provides compounds useful as inhibitors of Tyrosine Kinase 2 (Tyk2), solid forms and compositions thereof, methods of producing the same, and methods of using the same in the treatment of Tyk2-mediated diseases.
1. A compound of Formula I:
or a pharmaceutically acceptable salt thereof,
wherein each of X, Y, and Z is independently hydrogen or deuterium.
2. The compound of claim 1 of the formula:
or a pharmaceutically acceptable salt thereof.
3. The mesylate salt of the compound of claim 2 .
4. The free base of the compound of claim 2 .
5. The compound of claim 1 , wherein said compound is selected from the group consisting of:
or a pharmaceutically acceptable salt thereof.
6. A solid form of a compound of claim 1 .
7. A crystalline form of a compound according to claim 4 having a powder X-ray diffraction (XRPD) pattern as depicted in FIG. 1 .
8. A crystalline form of a compound according to claim 3 having a powder X-ray diffraction (XRPD) pattern as depicted in FIG. 2 .
9. A crystalline form of a compound according to claim 3 having a powder X-ray diffraction (XRPD) pattern as depicted in FIG. 3 .
10. A crystalline form of a compound according to claim 3 having a powder X-ray diffraction (XRPD) pattern as depicted in FIG. 4 .
11. A crystalline form of a compound according to claim 3 having a powder X-ray diffraction (XRPD) pattern as depicted in FIG. 5 .
12. A crystalline form of a compound according to claim 3 having a powder X-ray diffraction (XRPD) pattern as depicted in FIG. 6 .
13. A process for producing a compound of the formula:
comprising contacting a compound of the formula:
with an acid.
14. A process for producing a compound of the formula:
comprising contacting a compound of the formula:
with a compound of formula:
under aryl amination conditions.
15. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier, adjuvant, or diluent.
16. A method of inhibiting a Tyk2 enzyme in a patient or biological sample comprising contacting said patient or biological sample with a compound according to claim 1 .