Granted Patent B2

US 12,377,159 · App. 18/361,275 · Granted Aug 5, 2025

Inventors: Amy Han (Hockessin, DE); Andrew J. Murphy (Croton-on-Hudson, NY); William Olson (Yorktown Heights, NY)

Assignee: REGENERON PHARMACEUTICALS, INC.

A61K47/6803A61K31/566A61K31/58A61K47/61A61K47/6801A61K47/6849A61K47/6889A61K47/6951A61P29/00C07J41/005C07J41/0088C07J71/0026C07J71/0031

Abstract

Claims (56)

1. A compound of Formula (A):

or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

R 1 and R 2 together form

wherein R 4 is linear or branched alkyl, aryl, arylalkyl, or an N-containing heterocycloalkyl,

wherein the alkyl, aryl, arylalkyl, and N-containing heterocycloalkyl are, independently in each instance, optionally substituted with —NR c R d ,

wherein R c and R d are, independently in each instance, —H, alkyl, or optionally substituted aryl;

R 3 is —NR a R b ,

wherein R a and R b are, independently in each instance, —H, alkyl, or optionally substituted aryl;

R 5 is, independently in each instance, —OH, halo, alkyl, or arylalkyl; and

n is an integer from 0-19.

2. The compound of claim 1 , wherein the compound of Formula (A) is a compound of Formula (A 1 ):

or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

R 1 , R 2 , and R 3 are as defined above; and

R 5A and R 5B are, independently in each instance, —H or halo.

3. The compound of claim 2 , wherein:

R 1 and R 2 together form

wherein R 4 is linear or branched alkyl, aryl, or arylalkyl,

wherein the alkyl, aryl, and arylalkyl are, independently in each instance, optionally substituted with —NR c R d ,

wherein R c and R d are, independently in each instance, —H, alkyl, or optionally substituted aryl.

4. The compound of claim 1 , wherein R a is H and R b is H or alkyl.

5. The compound of claim 1 , wherein the compound of Formula (A) is a compound of Formula (A 4 ):

or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

R 3 is —NR a R b ;

R 4 is linear or branched alkyl; and

R a and R b are, independently in each instance, —H or alkyl.

6. The compound of claim 5 , wherein R 4 is C 1-4 linear or branched alkyl.

7. The compound of claim 5 , wherein R 3 is —NH 2 , —NHCH 3 , or —N(CH 3 ) 2 .

8. The compound of claim 1 , wherein the compound of Formula (A) is a compound of Formula (A 6 ):

or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

R 3 is —NR a R b ;

R 4 is linear or branched alkyl; and

R a and R b are, independently in each instance, —H or alkyl.

9. The compound of claim 1 , wherein the compound of Formula (A) is a compound of Formula 1110, 1120, 1130 or 1140:

or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

R 3 and R 4 are as defined above.

10. The compound of claim 9 wherein R 4 is n-propyl.

11. The compound of claim 10 according to formula 1120.

12. The compound of claim 9 wherein R 4 is H 2 NCH 2 CH 2 — or

13. The compound of claim 1 wherein R 4 is linear or branched alkyl, aryl, or arylalkyl.

14. The compound of claim 13 wherein R 3 is —NH 2 , —N(H)CH 3 , or —N(CH 3 ) 2 .

15. The compound of claim 13 wherein R 4 is n-propyl.

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

or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof.

17. A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier, diluent, or excipient.

18. The compound of claim 1 , of the formula

or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof.

19. The compound of claim 1 , of the formula

or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof.

20. The compound of claim 1 , of the formula

or a pharmaceutically acceptable salt or solvate.

21. The compound of claim 1 , according to Formula (A 2 )

wherein n is an integer from 0 to 4.

22. The compound of claim 1 , according to Formula (A 3 ):

wherein n is an integer from 1-4.

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

or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof.

Assignments (1)

Continuity (5)

References Cited (305)