Granted Patent B2

US 12,698,291 · App. 18/612,147 · Granted Aug 4, 2026

Inventors: Martin Smrcina (Oro Valley, AZ); Ronghua Li (Oro Valley, AZ); Anil Nair (Oro Valley, AZ); Paul August (Oro Valley, AZ); Kirsten Bjergarde (Oro Valley, AZ)

Assignee: ACURASTEM INCORPORATED

C07D491/048C07D405/14C07D413/14

Abstract

Claims (46)

1 . A compound of the formula (I)

or a pharmaceutically acceptable salt thereof, wherein

R 1 is hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl;

R 2 is substituted phenyl;

R 3 is selected from:

Ring A is (i) 5 or 6-membered heteroaryl having at least one nitrogen or oxygen ring atom, or (ii) phenyl;

L 1 is absent, C 1 -C 2 alkylene, —O—, —S—, —C(O)—, —NHC(O)—, or —C(O)NH—;

L 2 is —O—(CR a R b ) m —, NR c —(CR a R b ) m —, or —S—(CR a R b ) m —;

X 1 is CH, N, or CR c ;

each occurrence of R a and R b are independently hydrogen, hydroxy, hydroxy(C 1-4 )alkyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl, halogen, nitro, —OR d , —SR d , —NR d R e , —C(O)R d , —C(S)R d , —OC(O)R d , —SC(O)R d , OC(S)R d , SC(S)R d , —NR c C(O)R d , —NR c C(S)R d , —SO 2 R c , —S(O)R c , —NR c SO 2 R d , —OS(O) 2 R d , —OP(O)R d R e , or —P(O)R d R e ;

R c is hydrogen or C 1-6 alkyl;

each occurrence of R d and R e are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl;

m is 1-4; and

p is 1.

2 . The compound of claim 1 , wherein R 3 is selected from

3 . The compound of claim 1 , wherein ring A is 5-membered heteroaryl having at least one nitrogen ring atom.

4 . The compound of claim 1 , wherein ring A is selected from

5 . The compound of claim 1 , wherein ring A is selected from

6 . The compound of claim 1 , wherein L 1 is absent.

7 . The compound of claim 1 , wherein L 2 is —OCH 2 CH 2 —, —OCH 2 —, or —OCH 2 CH 2 CH(OH)CH 2 —.

8 . The compound of claim 1 , wherein the moiety

is selected from,

9 . A compound of the formula (II)

or a pharmaceutically acceptable salt thereof, wherein

R 1 is hydroxy, substituted or unsubstituted heteroaryl, or substituted or unsubstituted heterocyclyl;

R 2 is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl;

R 3 is substituted or unsubstituted oxygen-containing heterocyclyl;

Ring A is 5-membered heteroaryl having at least one nitrogen ring atom;

L 2 is —O—(CR a R b ) m —;

each occurrence of R a and R b are independently hydrogen, hydroxy, or hydroxy(C 1-4 )alkyl; and

m is 1-4.

10 . The compound of claim 9 , wherein R 3 is selected from

11 . The compound of claim 10 , wherein R 3 is

12 . The compound of claim 9 , wherein ring A is selected from

13 . A compound selected from

and pharmaceutically acceptable salts thereof.

14 . The compound of claim 13 , wherein the compound is selected from

and pharmaceutically acceptable salts thereof.

15 . The compound of claim 14 , wherein the compound is

and pharmaceutically acceptable salts thereof.

16 . The compound of claim 14 , wherein the compound is

and pharmaceutically acceptable salts thereof.

17 . The compound of claim 14 , wherein the compound is

and pharmaceutically acceptable salts thereof.

18 . The compound of claim 14 , wherein the compound is

and pharmaceutically acceptable salts thereof.

Assignments (1)

Continuity (3)

References Cited (149)