Granted Patent B2

US 12,351,567 · App. 18/511,586 · Granted Jul 8, 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 (40)

1. A compound of Formula (Ic):

wherein

A is

one of n and m is 0; and the other of n and m is 1;

X 1 and Y 1 are each O;

R 2 and R 7 are each OH;

R 1 , R 3 , R 6 , and R 8 are independently selected from H, OH, OCH 3 , OAc, NH 2 , halogen, CN, CF 3 , CO 2 H, NO 2 , NHAc, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, alkylamino, alkyl-R 9 , alkenyl-R 9 , alkynyl-R 9 , OR 10 , NHR 10 , NR 11 C(O)R 12 , C(O)NR 11 R 12 , and NR 11 SO 2 R 12 ;

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

each occurrence of R 9 is independently selected from OH, NH 2 , O-alkyl, O-alkyl-O-alkyl, alkylamino, NHC(O)-alkyl, N(CH 3 )C(O)-alkyl, NHSO 2 -alkyl, N(CH 3 )SO 2 -alkyl, aryl, heteroaryl, cycloalkyl, and heterocycloalkyl;

R 10 is selected from C 2 -C 12 alkyl, hydroxyalkyl, aminoalkyl, alkyl-O-alkyl, alkyl-O-alkyl-OH, alkyl-O-alkyl-O-alkyl, alkenyl, alkynyl, aralkyl, heteroaralkyl, alkyl-cycloalkyl, alkyl-heterocycloalkyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, SO 3 H, SO 2 -alkyl, and SO 2 -haloalkyl;

each occurrence of R 11 is selected from H and alkyl; and

each occurrence of R 12 is selected from alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, O-alkyl, aminoalkyl, aralkyl, heteroaralkyl, alkyl-cycloalkyl, and alkyl-heterocycloalkyl;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein A is

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 4 , wherein one of R 1 , R 3 , R 4 , R 5 , R 6 , and R 8 is alkyl or halogen.

7. The compound of claim 5 , wherein two of R 1 , R 3 , R 4 , R 5 , R 6 , and R 8 are alkyl or halogen.

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

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

or a pharmaceutically acceptable salt thereof.

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

or a pharmaceutically acceptable salt thereof.

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

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

and, or a pharmaceutically acceptable salt thereof.

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

or a pharmaceutically acceptable salt thereof.

14. A pharmaceutical composition comprising a compound of claim 9 ; and a pharmaceutically acceptable carrier.

15. A pharmaceutical composition comprising a compound of claim 10 ; and a pharmaceutically acceptable carrier.

16. A pharmaceutical composition comprising a compound of claim 12 ; and a pharmaceutically acceptable carrier.

17. A pharmaceutical composition comprising a compound of claim 13 ; and a pharmaceutically acceptable carrier.

18. The compound of claim 1 , wherein

wherein

A is

R 2 and R 7 are each OH; and

R 1 , R 3 , R 4 , R 5 , R 6 , and R 8 are independently selected from H, halogen, and alkyl;

or a pharmaceutically acceptable salt thereof.

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

Assignments (7)

Continuity (3)

References Cited (157)