IP Library › Granted Patent US 12673930

Granted Patent B2

US 12673930 · App. 18/006,059 · Granted Jul 7, 2026

Thiophene HSD17B13 inhibitors and uses thereof

Inventors: Joshua Odingo (Bothell, WA); Sampath Kumar Anandan (Fremont, CA); Heather Kay Webb Hsu (Seattle, WA); Vincent Florio (Seattle, WA); Subramanyam Janardhan Tantry (Karnataka, IN); Athisayamani Jeyaraj Duraiswamy (Karnataka, IN)

Assignee: INIPHARM, INC.

C07D333/38 C07D409/12 C07D495/04

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Quick Facts

Patent No.: US 12673930
App. No.: 18/006,059
Granted: Jul 7, 2026
Kind: B2

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Abstract

Described herein are HSD17B13 inhibitors and pharmaceutical compositions comprising said inhibitors. The subject compounds and compositions are useful for the treatment of liver disease, metabolic disease, or cardiovascular disease, such as NAFLD or NASH, or drug induced liver injury (DILI).

Claims (97)

1 . A compound of Formula (I), or a pharmaceutically acceptable salt, solvate, or

wherein:

R 1 is halogen;

R 2 is hydrogen, —P(═O)OH 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is optionally substituted with one, two, or three R 2a ;

each R 2a is independently deuterium, halogen, —CN, —OH, —OR a , —NR c R d , —C(═O)R a , —C(═O)OR b , —C(═O)NR c R d , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

each R 3 is independently hydrogen, deuterium, halogen, —CN, —OH, —OR a , —SH, —SR a , —S(═O)R a , —S(═O) 2 R a , —NO 2 , —NR c R d , —NHS(═O) 2 R a , —S(═O) 2 NR c R d , —C(═O)R a , —OC(═O)R a , —C(═O)OR b , —OC(═O)OR b , —C(═O)NR c R d , —OC(═O)NR c R d , —NR b C(═O)NR c R d , —NR b C(═O)R a , —NR b C(═O)OR b , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

n is 1-3;

each R 4 is independently hydrogen, deuterium, halogen, —CN, —OH, —OR a , —SH, —SR a , —S(═O)R a , —S(═O) 2 R a , —NO 2 , —NR c R d , —NHS(═O) 2 R a , —S(═O) 2 NR c R d , —C(═O)R a , —OC(═O)R a , —C(═O)OR b , —OC(═O)OR b , —C(═O)NR c R d , —OC(═O)NR c R d , —NR b C(═O)NR c R d , —NR b C(═O)R a , —NR b C(═O)OR b , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

or two R 4 are taken together to form a cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein the cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is optionally substituted with one, two, or three deuterium, oxo, halogen, —CN, —OH, —OMe, —S(═O)Me, —S(═O) 2 Me, —NH 2 , —S(═O) 2 NH 2 , —C(═O)Me, —C(═O)OH, —C(═O)OMe, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, or C 1 -C 6 aminoalkyl;

m is 1 or 2;

R 5 and R 7 are independently hydrogen, —S(═O)R a , —S(═O) 2 R a , —S(═O) 2 NR c R d , —C(═O)R a , —C(═O)OR b , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

R 6 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl (cycloalkyl), C 1 -C 6 alkyl (heterocycloalkyl), C 1 -C 6 alkyl (aryl), or C 1 -C 6 alkyl (heteroaryl); wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 6a ;

each R 6a is independently deuterium, halogen, —CN, —OH, —OR 20 , —SH, —SR 20 , —S(═O)R 20 , —S(═O) 2 R 20 , —NO 2 , —NR 22 R 23 , —NHS(═O) 2 R 20 , —S(═O) 2 NR 22 R 23 , —S(═O) 2 NR 21 C(═O)R 20 , —C(═O)R 20 , —OC(═O)R 20 , —C(═O)OR 21 , —OC(═O)OR 21 , —C(═O)NR 22 R 23 , —OC(═O)NR 22 R 23 , —NR 21 C(═O)NR 22 R 23 , —NR 21 C(═O)R 20 , —NR 21 C(═O)OR 21 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

each R 20 is independently C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three deuterium, oxo, halogen, —CN, —OH, —OMe, —S(═O)Me, —S(═O) 2 Me, —NH 2 , —S(═O) 2 NH 2 , —C(═O)Me, —C(═O)OH, —C(═O)OMe, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, or C 1 -C 6 aminoalkyl;

each R 21 is independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three deuterium, oxo, halogen, —CN, —OH, —OMe, —S(═O)Me, —S(═O) 2 Me, —NH 2 , —S(═O) 2 NH 2 , —C(═O)Me, —C(═O)OH, —C(═O)OMe, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, or C 1 -C 6 aminoalkyl;

each R 22 and R 23 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three oxo, deuterium, halogen, —CN, —OH, —OMe, —S(═O)Me, —S(═O) 2 Me, —NH 2 , —S(═O) 2 NH 2 , —C(═O)Me, —C(═O)OH, —C(═O)OMe, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, or C 1 -C 6 aminoalkyl;

or R 22 and R 23 are taken together with the atom to which they are attached to form a heterocycloalkyl optionally substituted with one, two, or three oxo, deuterium, halogen, —CN, —OH, —OMe, —S(═O)Me, —S(═O) 2 Me, —NH 2 , —S(═O) 2 NH 2 , —C(═O)Me, —C(═O)OH, —C(═O)OMe, C 1 -C 6 alkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, or C 1 -C 6 aminoalkyl;

each R a is independently C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl (cycloalkyl), C 1 -C 6 alkyl (heterocycloalkyl), C 1 -C 6 alkyl (aryl), or C 1 -C 6 alkyl (heteroaryl); wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three deuterium, oxo, halogen, —CN, —OH, —OMe, —S(═O)Me, —S(═O) 2 Me, —NH 2 , —S(═O) 2 NH 2 , —C(═O)Me, —C(═O)OH, —C(═O)OMe, C 1 -C 6 alkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, or C 1 -C 6 aminoalkyl;

each R b is independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl (cycloalkyl), C 1 -C 6 alkyl (heterocycloalkyl), C 1 -C 6 alkyl (aryl), or C 1 -C 6 alkyl (heteroaryl); wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three deuterium, oxo, halogen, —CN, —OH, —OMe, —S(═O)Me, —S(═O) 2 Me, —NH 2 , —S(═O) 2 NH 2 , —C(═O)Me, —C(═O)OH, —C(═O)OMe, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, or C 1 -C 6 aminoalkyl; and

each R c and R d are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl (cycloalkyl), C 1 -C 6 alkyl (heterocycloalkyl), C 1 -C 6 alkyl (aryl), or C 1 -C 6 alkyl (heteroaryl); wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three oxo, deuterium, halogen, —CN, —OH, —OMe, —S(═O)Me, —S(═O) 2 Me, —NH 2 , —S(═O) 2 NH 2 , —C(═O)Me, —C(═O)OH, —C(═O)OMe, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, or C 1 -C 6 aminoalkyl;

or R c and R d are taken together with the atom to which they are attached to form a heterocycloalkyl optionally substituted with one, two, or three oxo, deuterium, halogen, —CN, —OH, —OMe, —S(═O)Me, —S(═O) 2 Me, —NH 2 , —S(═O) 2 NH 2 , —C(═O)Me, —C(═O)OH, —C(═O)OMe, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, or C 1 -C 6 aminoalkyl.

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

R 1 is chloro.

3 . The compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

R 2 is hydrogen.

4 . The compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

each R 3 is independently hydrogen, halogen, or C 1 -C 6 alkyl.

5 . The compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

n is 1.

6 . The compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

each R 4 is independently hydrogen, halogen, or C 1 -C 6 alkyl.

7 . The compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

m is 1.

8 . The compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

R 5 is hydrogen.

9 . The compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

R 7 is hydrogen.

10 . The compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

R 6 is C 1 -C 6 alkyl (aryl) or C 1 -C 6 alkyl (heteroaryl); wherein the alkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 6a .

11 . The compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

R 6 is C 1 -C 6 alkyl (aryl); wherein the alkyl and aryl is independently optionally substituted with one, two, or three R 6a .

12 . The compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

R 6 is C 1 -C 6 alkyl optionally substituted with one, two, or three R 6a .

13 . The compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

each R 6a is independently deuterium, halogen, —CN, —OH, —OR 20 , —NR 22 R 23 , C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl.

14 . The compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

each R 6a is independently —OR 20 .

15 . The compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, wherein:

each R 20 is independently C 1 -C 6 alkyl.

16 . A compound of Formula (II), or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof:

wherein:

m is 1 or 2;

each R 8 is independently hydrogen, deuterium, halogen, —CN, —OH, —OR a , —SH, —SR a , —S(═O)R a , —S(═O) 2 R a , —NO 2 , —NR c R d , —NHS(═O) 2 R a , —S(═O) 2 NR c R d , —C(═O)R a , —OC(═O)R a , —C(═O)OR b , —OC(═O)OR b , —C(═O)NR c R d , —OC(═O)NR c R d , —NR b C(═O)NR c R d , —NR b C(═O)R a , —NR b C(═O)OR b , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

p is 1-4;

R 9 is hydrogen, —P(═O)OH 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

R 10 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl (cycloalkyl), C 1 -C 6 alkyl (heterocycloalkyl), C 1 -C 6 alkyl (aryl), or C 1 -C 6 alkyl (heteroaryl); wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 10a ;

each R 10a is independently deuterium, halogen, —CN, —OH, —OR 20 , —OP(═O)OH 2 , —SH, —SR 20 , —S(═O)R 20 , —S(═O) 2 R 20 , —NO 2 , —NR 22 R 23 , —NHS(═O) 2 R 20 , —S(═O) 2 NR 22 R 23 , —S(═O) 2 NR 21 C(═O)R 20 , —C(═O)R 20 , —OC(═O)R 20 , —C(═O)OR 21 , —OC(═O)OR 21 , —C(═O)NR 22 R 23 , —OC(═O)NR 22 R 23 , —NR 21 C(═O)NR 22 R 23 , —NR 21 C(═O)R 20 , —NR 21 C(═O)OR 21 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

17 . A compound of Formula (IV), or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof:

wherein:

R 1 is halogen;

R 2 is hydrogen, —P(═O)OH 2 , C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is optionally substituted with one, two, or three R 2a ;

n is 1-3;

each R 4 is independently hydrogen, deuterium, halogen, —CN, —OH, —OR a , —SH, —SR a , —S(═O)R a , —S(═O) 2 R a , —NO 2 , —NR c R d , —NHS(═O) 2 R a , —S(═O) 2 NR c R d , —C(═O)R a , —OC(═O)R a , —OC(═O)OR b , —C(═O)NR c R d , —OC(═O)NR c R d , —NR b C(═O)NR c R d , —NR b C(═O)R a , —NR b C(═O)OR b , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

m is 1 or 2;

R 6 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl (cycloalkyl), C 1 -C 6 alkyl (heterocycloalkyl), C 1 -C 6 alkyl (aryl), or C 1 -C 6 alkyl (heteroaryl); wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 6a ;

each R 6a is independently deuterium, halogen, —CN, —OH, —OR 20 , —SH, —SR 20 , —S(═O)R 20 , —S(═O) 2 R 20 , —NO 2 , —NR 22 R 23 , —NHS(═O) 2 R 20 , —S(═O) 2 NR 22 R 23 , —C(═O)R 20 , —OC(═O)R 20 , —C(═O)OR 21 , —OC(═O)OR 21 , —C(═O)NR 22 R 23 , —OC(═O)NR 22 R 23 , —NR 21 C(═O)NR 22 R 23 , —NR 21 C(═O)R 20 , —NR 21 C(═O)OR 21 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 aminoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

18 . The compound of claim 1 selected from the group consisting of:

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

19 . A pharmaceutical composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, and a pharmaceutically acceptable carrier.

20 . A method of treating Nonalcoholic Fatty Liver Disease in a subject in need thereof, the method comprising administering a pharmaceutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof.

21 . The compound of claim 16 selected from the group consisting of:

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

22 . The compound of claim 17 selected from the group consisting of:

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