Granted Patent B2

US 12,528,767 · App. 17/631,422 · Granted Jan 20, 2026

Inventors: Florence Fevrier Wagner (Cambridge, MA); Jacob Matthew Hooker (Winchester, MA); Stéphane Ouellet (Sudbury, MA)

Assignee: Eikonizo Therapeutics, Inc.

C07D205/12C07D209/08C07D217/04C07D237/30C07D405/04C07D451/06C07D471/04C07D487/04C07D491/08C07D491/107C07D493/08C07D498/04

Abstract

Claims (46)

1 . A compound of Formula (I):

or a pharmaceutically acceptable salt thereof, wherein:

X 1 is hydrogen or fluoro;

X 2 is hydrogen or fluoro; provided that at least one of X 1 and X 2 is fluoro;

A is substituted or unsubstituted alkyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted aryl;

R 1 is hydrogen or substituted or unsubstituted alkyl;

R 2 is hydrogen or substituted or unsubstituted alkyl; or R 1 and R 2 together form a substituted or unsubstituted heterocyclyl, or a substituted or unsubstituted cycloalkyl;

R a is hydrogen or is joined with R c to form a substituted or unsubstituted bridged ring;

R b is hydrogen or is joined with R c to form a substituted or unsubstituted bridged ring;

R c is hydrogen or substituted or unsubstituted alkyl or is joined with at least one of R a and R b to form a substituted or unsubstituted bridged ring;

m is 0 or 1; and

n is 0 or 1.

2 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

X 1 is hydrogen; and

X 2 is fluoro.

3 . The compound of claim 2 , or a pharmaceutically acceptable salt thereof, wherein:

A is unsubstituted C 1-4 alkyl, C 1-4 haloalkyl, substituted or unsubstituted C 3-14 carbocyclyl, substituted or unsubstituted 3-14-membered heterocyclyl, substituted or unsubstituted 5-14 membered monocyclic or polycyclic heteroaryl, or substituted or unsubstituted C 6-14 aryl.

4 . The compound of claim 2 , or a pharmaceutically acceptable salt thereof, wherein:

A is —CF 3 , —C(CH 3 ) 3 , phenyl, 2,6-dimethylphenyl, tetrahydrofuranyl, oxetanyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl,

5 . The compound of claim 3 , or a pharmaceutically acceptable salt thereof, wherein:

R 1 is hydrogen; and

R 2 is hydrogen.

6 . The compound of claim 5 , or a pharmaceutically acceptable salt thereof, wherein:

R a , R b , and Re are each hydrogen.

7 . The compound of claim 6 , or a pharmaceutically acceptable salt thereof, wherein:

n is 1.

8 . The compound of claim 1 , wherein the compound is of Formula (I-c) or Formula (I-d):

or a pharmaceutically acceptable salt thereof, wherein

A is C 3-14 carbocyclyl or 3-14 membered heterocyclyl;

R 1 is hydrogen, methyl or ethyl; and R 2 is hydrogen, methyl or ethyl; or

R 1 and R 2 together form a substituted or unsubstituted C 3-6 cycloalkyl.

9 . A compound of formula:

or a pharmaceutically acceptable salt thereof.

10 . The compound of claim 3 , or a pharmaceutically acceptable salt thereof, wherein:

R a , R b , and Re are each hydrogen;

R 1 is hydrogen, methyl, or ethyl; and

R 2 is hydrogen, methyl, or ethyl; or R 1 and R 2 together form a C 3-6 cycloalkyl.

11 . The compound of claim 10 , or a pharmaceutically acceptable salt thereof, wherein A is substituted or unsubstituted C 6 aryl or substituted or unsubstituted 5-6 membered heteroaryl.

12 . The compound of claim 10 , or a pharmaceutically acceptable salt thereof, wherein A is substituted or unsubstituted C 3-6 monocyclic cycloalkyl.

13 . The compound of claim 10 , or a pharmaceutically acceptable salt thereof, wherein A is substituted or unsubstituted monocyclic 4-7 membered heterocyclyl.

14 . The compound of claim 10 , or a pharmaceutically acceptable salt thereof, wherein A is substituted or unsubstituted 8-10 membered bridged heterocyclyl.

15 . The compound of claim 10 , or a pharmaceutically acceptable salt thereof, wherein A is substituted or unsubstituted C 3-14 polycyclic carbocyclyl or substituted or unsubstituted 3-14 membered heterocyclyl.

16 . The compound of claim 15 , or a pharmaceutically acceptable salt thereof, wherein A is a substituted or unsubstituted bicyclic spirocyclic C 3-14 carbocyclyl or a substituted or unsubstituted bicyclic spirocyclic 3-14 membered heterocyclyl.

17 . The compound of claim 16 , or a pharmaceutically acceptable salt thereof, wherein A is a substituted or unsubstituted C 5-10 spirocyclic cycloalkyl.

18 . The compound of claim 10 , or a pharmaceutically acceptable salt thereof, wherein A is a substituted or unsubstituted oxetanyl, or a substituted or unsubstituted adamantyl.

19 . The compound of claim 10 , or a pharmaceutically acceptable salt thereof, wherein A is unsubstituted C 1-4 alkyl or C 1-4 haloalkyl.

Assignments (1)

Continuity (2)

References Cited (400)