Granted Patent B2

US 12,358,884 · App. 18/511,627 · Granted Jul 15, 2025

Inventors: Christopher L. Rinsch (Lausanne, CH); Penelope Andreux (Eclepens, CH); Jonathan Mark Sutton (Harlow, GB); Eileen Mary Seward (Harlow, GB); Jamie D. Knight (Harlow, GB); Ian Linney (London, GB); Peter C. Sennhenn (Munich, DE); Said Oumouch (Wittenheim, FR); Florent Beaufils (Bartenheim, FR); Thomas Christian Fessard (Küsnacht, CH)

Assignee: Vandria SA

C07D311/80C07D217/24C07D279/02C07D407/12C07D491/04C07D491/107C07D493/04C07D493/10

Abstract

Claims (34)

1. A compound of Formula (Ia):

wherein

A is

X 1 is O;

Y 1 is O;

R 1 , R 4 , R 5 and R 8 are independently selected from H and halogen;

R 3 and R 6 are independently selected from H, CN, OH, CF 3 , halogen, and alkyl;

R 2 is OH; and R 7 is alkynyl-R 9 ;

R 9 is selected from OH, O-alkyl, NHSO 2 -alkyl, N(CH 3 )SO 2 -alkyl, unsubstituted or substituted cycloalkyl, and unsubstituted or substituted heterocycloalkyl; and

each cycloalkyl or heterocycloalkyl, when substituted, is substituted with alkyl, halogen, hydroxyl, carboxyl, thiocarbonyl, alkoxy, amino, amido, amidine, an imine, cyano, nitro, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, heterocyclyl, and/or aralkyl;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein R 9 is selected from OH and unsubstituted or substituted heterocycloalkyl.

3. The compound of claim 1 , wherein R 1 , R 3 , R 4 , R 5 , R 6 , and R 8 are each H.

4. The compound of claim 1 , wherein one of R 1 , R 3 , R 4 , R 5 , R 6 , and R 8 is not H.

5. The compound of claim 1 , wherein two of R 1 , R 3 , R 4 , R 5 , R 6 , and R 8 are not H.

6. The compound of claim 1 , wherein the compound is selected from:

7. The compound of claim 1 , wherein the compound is selected from:

or a pharmaceutically acceptable salt thereof.

8. A pharmaceutical composition, comprising a compound of claim 1 ; and a pharmaceutically acceptable carrier.

9. The compound of claim 1 , wherein each cycloalkyl or heterocycloalkyl, when substituted, is substituted with hydroxy or alkoxy.

10. The compound of claim 1 , wherein R 9 is OH.

11. The compound of claim 1 , wherein R 9 is O-alkyl.

12. The compound of claim 1 , wherein R 9 is unsubstituted heterocycloalkyl.

13. The compound of claim 1 , wherein R 9 is substituted cycloalkyl.

14. The compound of claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

15. The compound of claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

16. The compound of claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

17. A pharmaceutical composition, comprising a compound of claim 7 ; and a pharmaceutically acceptable carrier.

18. A pharmaceutical composition, comprising a compound of claim 14 ; and a pharmaceutically acceptable carrier.

19. A pharmaceutical composition, comprising a compound of claim 15 ; and a pharmaceutically acceptable carrier.

20. A pharmaceutical composition, comprising a compound of claim 16 ; and a pharmaceutically acceptable carrier.

Assignments (7)

Continuity (3)

References Cited (156)