IP Library › Granted Patent US 12,509,459

Granted Patent B2

US 12,509,459 · App. 19/089,839 · Granted Dec 30, 2025

Inhibitors of NLRP3 inflammasome

Inventors: George Hartman (Lansdale, PA); Yan Wang (Richmond, CA); Paul Humphries (Richmond, CA); Rusty Montgomery (Richmond, CA); Matthias Geyer (Bonn, DE); Kevin Wilhelmsen (Richmond, CA); Shijun Yan (Richmond, CA)

C07D471/04 A61K31/416 A61K31/437 A61K31/4545 A61K31/5377 A61P3/04 A61P19/06 C07D231/56 C07D403/06

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Quick Facts

Patent No.: US 12,509,459
App. No.: 19/089,839
Granted: Dec 30, 2025
Kind: B2

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Abstract

The present disclosure relates to compounds that act as inhibitors of NLRP3 inflammasomes; pharmaceutical compositions comprising the compounds; and methods of treating cancer and disorders associated with inflammation and inflammaging.

Claims (155)

1 . A compound of Formula I:

or a pharmaceutically acceptable salt thereof;

wherein

Ring A is selected from the group consisting of C 6-10 aryl, 5-10 membered heteroaryl, C 3-10 cycloalkyl, and 4-10 membered heterocycloalkyl;

Ring B is selected from the group consisting of C 6-10 aryl, 5-6 membered heteroaryl, C 3-6 cycloalkyl, and 3-6 membered heterocycloalkyl;

alternatively, Ring B and R 5 are absent;

R 1 is selected from the group consisting of H, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkoxy, OC 3-6 cycloalkyl, O(C 0-6 alkylene-C 6-10 aryl), and C 0-6 alkylene-C 6-10 aryl, wherein alkyl and cycloalkyl are optionally substituted with OH, OC(O)C 1-6 alkyl, C(O)C 1-6 alkyl, N(R a ) 2 , and halo;

each R a is independently H, C 1-6 alkyl, C 3-6 cycloalkyl, and C(O)C 1-6 alkyl;

R 2 is H or C 1-6 alkyl;

R 3 is selected from the group consisting of C 1-6 alkyl, C 3-6 cycloalkyl, 3-6 membered heterocycloalkyl, and 5-10 membered heteroaryl, wherein C 1-6 alkyl and C 3-6 cycloalkyl are substituted by OH, C 1-6 alkoxy, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl)(C 1-6 haloalkyl), NH(C 1-6 haloalkyl), N(C 1-6 alkyl) 2 , N(C 1-6 haloalkyl) 2 , halo, SO 2 R 6 , NHCOR 6 , 3-6 membered heterocycloalkyl optionally substituted with one or two halo or OH, or C 0-3 alkylene-5-10 membered heteroaryl, wherein 3-6 membered heterocycloalkyl is independently optionally oxidized and independently optionally substituted by C 1-6 alkyl; and the nitrogen atom of NH(C 1-6 alkyl), N(C 1-6 alkyl)(C 1-6 haloalkyl), NH(C 1-6 haloalkyl), N(C 1-6 alkyl) 2 , and N(C 1-6 haloalkyl) 2 is optionally oxidized and one or more carbon atoms of the alkyl groups on the nitrogen atom are optionally substituted with 1-6 deuterium atoms or C 1-6 alkoxy;

alternatively, R 2 and R 3 , together with the atom to which they are attached, form a ring selected from the group consisting of C 3-7 cycloalkyl and 3-7 membered heterocycloalkyl, both of which are substituted by OH, C 1-6 alkoxy, or C 1-4 alkylene-O—C 1-4 alkyl;

each R 4 is independently selected from the group consisting of C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, halo, OH, OR 6 , NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , C 1-6 alkylene-NHCOR 6 , NHCOR 6 , CN, C 1-6 haloalkyl, C 3-7 cycloalkyl, 3-7 membered heterocycloalkyl, and COR 6 ;

alternatively, two R 4 , together with the atoms to which they are attached, form a ring selected from the group consisting of phenyl, 5-6 membered heteroaryl, C 4-6 cycloalkyl, and 4-6 membered heterocycloalkyl all of which are optionally substituted with one, two, or three R 7 ;

each R 5 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 haloalkyl, halo, OH, OR 6 , NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , NHCOR 6 , CN, C 3-7 cycloalkyl, 3-7 membered heterocycloalkyl, COR 6 , and SO 2 R 6 ;

alternatively, two R 5 , together with the atoms to which they are attached, form a ring selected from the group consisting of phenyl, 5-6 membered heteroaryl, C 4-6 cycloalkyl, and 4-6 membered heterocycloalkyl all of which are optionally substituted with one, two, or three R 7 ;

each R 6 is independently selected from the group consisting of C 1-6 alkyl, C 2-6 alkenyl, C 0-6 alkylene-C 6-10 aryl, C 0-6 alkylene-5-10 membered heteroaryl, C 1-6 alkoxy, C 3-6 cycloalkyl, 3-6 membered heterocycloalkyl, halo, NH 2 , NH(C 1-6 alkyl), and N(C 1-6 alkyl) 2 ;

each R 7 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 haloalkyl, halo, OH, C 1-6 alkoxy, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , CN, COR 8 , and SO 2 R 8 ;

each R 8 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, halo, NH 2 , NH(C 1-6 alkyl), and N(C 1-6 alkyl) 2 ;

each R 9 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkyl-OH, halo, CN, OH, SO 2 R 6 , NH 2 , NH(C 1-6 alkyl), and N(C 1-6 alkyl) 2 ;

m is 0, 1, 2, or 3;

n is 0, 1, 2, or 3; and

p is 0, 1, 2, or 3.

2 . The compound of claim 1 , wherein

Ring A is C 6-10 aryl;

Ring B is C 6-10 aryl;

R 1 is C 1-6 alkyl;

R 2 is H;

R 3 is selected from the group consisting of C 1-6 alkyl, C 3-6 cycloalkyl, and 3-6 membered heterocycloalkyl, all of which are substituted by OH, C 1-6 alkoxy, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , halo, SO 2 R 6 , or C 1-3 alkylene-5-10 membered heteroaryl;

each R 9 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkyl-OH, SO 2 R 6 , and halo;

m is 0, 1, 2, or 3;

n is 0, 1, 2, or 3; and

p is 0, 1, 2, or 3.

3 . The compound of claim 1 , wherein

Ring A is C 6-10 aryl;

Ring B is C 6-10 aryl;

R 1 is C 1-6 alkyl;

R 2 is H;

R 3 is selected from the group consisting of C 1-6 alkyl, C 3-6 cycloalkyl, and 3-6 membered heterocycloalkyl, all of which are substituted by OH, NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , or C 1-6 alkoxy;

each R 4 is independently selected from the group consisting of C 1-6 alkyl, halo, OH, C 1-6 alkoxy, OC 3-6 cycloalkyl, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , NHC(O)C 1-6 alkyl, CN, and C 1-6 haloalkyl;

each R 5 is independently selected from the group consisting of C 1-6 alkyl, halo, OH, C 1-6 alkoxy, OC 3-6 cycloalkyl, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , CONH 2 , CONH(C 1-6 alkyl), CN, and C 1-6 haloalkyl;

each R 9 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkyl-OH, halo, CN, OH, NH 2 , NH(C 1-6 alkyl), and N(C 1-6 alkyl) 2 ;

m is 0, 1, or 2;

n is 0, 1, or 2; and

p is 0 or 1.

4 . The compound of claim 1 , wherein the compound of Formula I is a compound of Formula Ia:

or a pharmaceutically acceptable salt thereof.

5 . The compound of claim 1 , wherein R 1 is C 1-6 alkyl;

R 2 is H;

each R 4 is independently selected from the group consisting of halo, C 1-6 alkoxy, OC 3-6 cycloalkyl, and C 1-6 haloalkyl;

each R 5 is independently selected from the group consisting of C 1-6 alkyl, halo, CN, and C(O)NH(C 1-6 alkyl); and

each R 9 is independently selected from the group consisting of C 1-3 alkyl, C 1-6 alkoxy, C 1-3 alkyl-OH, and halo.

6 . The compound of claim 1 , wherein R 3 is C 1-6 alkyl substituted by OH, NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , or C 1-3 alkoxy.

7 . The compound of claim 1 , wherein m is 0, 1, or 2,

n is 1; and

p is 0 or 1.

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

or a pharmaceutically acceptable salt thereof.

9 . A compound of Formula II:

or a pharmaceutically acceptable salt thereof;

wherein

Ring A is selected from the group consisting of C 6-10 aryl, 5-10 membered heteroaryl, C 3-10 cycloalkyl, and 4-10 membered heterocycloalkyl;

Ring B is selected from the group consisting of phenyl, 5-6 membered heteroaryl, C 3-6 cycloalkyl, and 3-6 membered heterocycloalkyl;

alternatively, Ring B and R 5 are absent;

R 1 is selected from the group consisting of C 1-6 alkyl, C 3-6 cycloalkyl, C 0-6 alkylene-C 6-10 aryl, and 3-7 membered heterocycloalkyl, wherein C 1-6 alkyl, C 3-6 cycloalkyl, and C 0-6 alkylene-C 6-10 aryl are substituted with OH, halo, SO 2 R 6 , OC(O)C 1-6 alkyl, C(O)C 1-6 alkyl, 3-6 membered heterocycloalkyl, and N(R a ) 2 , wherein 3-6 membered heterocycloalkyl is optionally substituted by one or two halo;

each R a is independently H, C 1-6 alkyl, C 3-6 cycloalkyl, and C(O)C 1-6 alkyl;

R 2 is H or C 1-6 alkyl;

each R 4 is independently selected from the group consisting of C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, halo, OH, OR 6 , NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , C 1-6 alkyl-NHCOR 6 , NHCOR 6 , CN, C 1-6 haloalkyl, C 3-7 cycloalkyl, 3-7 membered heterocycloalkyl, and COR 6 ;

each R 7 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 haloalkyl, halo, OH, C 1-6 alkoxy, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , CN, COR, and SO 2 R 8 ;

each R 8 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, halo, NH 2 , NH(C 1-6 alkyl), and N(C 1-6 alkyl) 2 ;

each R 9 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkyl-OH, C 1-6 alkyl-NH(C 1-3 alkyl), halo, CN, OH, SO 2 R 6 , NH 2 , NH(C 1-6 alkyl), and N(C 1-6 alkyl) 2 ;

m is 0, 1, 2, or 3;

n is 0, 1, 2, or 3; and

p is 0, 1, 2, or 3.

10 . The compound of claim 9 , wherein

Ring A is C 6-10 aryl;

Ring B is C 6-10 aryl;

R 1 is selected from the group consisting of C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkoxy, OC 3-6 cycloalkyl, O(C 0-6 alkylene-C 6-10 aryl), and C 0-6 alkylene-C 6-10 aryl, all of which are substituted with OH, halo, SO 2 R 6 , OC(O)C 1-6 alkyl, C(O)C 1-6 alkyl, and N(R a ) 2 ;

each R a is independently H, C 1-6 alkyl, C 3-6 cycloalkyl, and C(O)C 1-6 alkyl;

R 2 is H or C 1-6 alkyl;

each R 4 is independently selected from the group consisting of halo, OH, C 1-6 alkoxy, OC 3-6 cycloalkyl, CN, and C 1-6 haloalkyl;

each R 5 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 haloalkyl, halo, CN, CONH 2 , and CONH(C 1-6 alkyl);

each R 9 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkyl-OH, halo, CN, OH, SO 2 R 6 , NH 2 , NH(C 1-6 alkyl), and N(C 1-6 alkyl) 2 ;

m is 0, 1, 2, or 3;

n is 0, 1, 2, or 3; and

p is 0, 1, 2, or 3.

11 . The compound of claim 9 , wherein

Ring A is phenyl;

Ring B is phenyl;

R 1 is selected from the group consisting of C 1-6 alkyl and C 3-6 cycloalkyl, both of which are substituted with OH;

R 2 is H or C 1-6 alkyl;

each R 4 is independently selected from the group consisting of halo, OH, C 1-6 alkoxy, OC 3-6 cycloalkyl, and C 1-6 haloalkyl;

each R 5 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 haloalkyl, halo, CN, CONH 2 , and CONH(C 1-6 alkyl);

each R 9 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkyl-OH, halo, CN, OH, NH 2 , NH(C 1-6 alkyl), and N(C 1-6 alkyl) 2 ;

m is 0, 1, or 2;

n is 0, 1, or 2; and

p is 0 or 1.

12 . The compound of claim 9 , wherein the compound of Formula II is a compound of Formula IIa:

or a pharmaceutically acceptable salt thereof.

13 . The compound of claim 9 , wherein R 1 is C 1-6 alkyl substituted by OH.

14 . The compound of claim 9 , wherein each R 4 is independently selected from the group consisting of C 1-6 alkoxy and OC 3-6 cycloalkyl;

each R 5 is independently selected from the group consisting of halo, CN, CONH 2 , and CONH(C 1-6 alkyl); and

each R 9 is independently selected from the group consisting of C 1-6 alkyl-OH, halo, OH, NH 2 , NH(C 1-6 alkyl), and N(C 1-6 alkyl) 2 .

15 . The compound of claim 9 , wherein m is 0, 1, or 2;

n is 1; and

p is 0 or 1.

16 . The compound of claim 9 , wherein the compound of Formula II is selected from

or a pharmaceutically acceptable salt thereof.

17 . A compound of Formula III:

or a pharmaceutically acceptable salt thereof;

wherein

Ring A is selected from the group consisting of C 6-10 aryl, C 3-10 cycloalkyl, and 4-10 membered heterocycloalkyl;

Ring B is selected from the group consisting of C 6-10 aryl, 5-6 membered heteroaryl, C 3-6 cycloalkyl, and 3-6 membered heterocycloalkyl;

alternatively, Ring B and R 5 are absent;

R 1 is selected from the group consisting of H, C 1-6 alkyl, C 3-6 cycloalkyl, OC 3-6 cycloalkyl, O(C 0-6 alkylene-C 6-10 aryl), and C 0-6 alkylene-C 6-10 aryl, wherein alkyl and cycloalkyl are optionally substituted with OH, OC(O)C 1-6 alkyl, C(O)C 1-6 alkyl, N(R a ) 2 , and halo;

each R a is independently H, C 1-6 alkyl, C 3-6 cycloalkyl, and C(O)C 1-6 alkyl;

R 2 is H or C 1-6 alkyl;

R 3 is selected from the group consisting of H, C 1-6 alkyl, C 3-6 cycloalkyl, 3-6 membered heterocycloalkyl, and 5-10 membered heteroaryl, wherein C 1-6 alkyl and C 3-6 cycloalkyl are substituted by OH, C 1-6 alkoxy, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl)(C 1-6 haloalkyl), NH(C 1-6 haloalkyl), N(C 1-6 alkyl) 2 , N(C 1-6 haloalkyl) 2 , halo, SO 2 R 6 , NHCOR 6 , 3-6 membered heterocycloalkyl optionally substituted with one or two halo or OH, or C 0-3 alkylene-5-10 membered heteroaryl, wherein 3-6 membered heterocycloalkyl is independently optionally oxidized and independently optionally substituted by C 1-6 alkyl; and the nitrogen atom of NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl)(C 1-6 haloalkyl), NH(C 1-6 haloalkyl), N(C 1-6 alkyl) 2 , and N(C 1-6 haloalkyl) 2 is optionally oxidized and one or more carbon atoms of the alkyl groups on the nitrogen atom are optionally substituted with 1-6 deuterium atoms or C 1-6 alkoxy;

each R 7 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 haloalkyl, halo, OH, C 1-6 alkoxy, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , CN, COR 8 , and SO 2 R 8 ;

each R 8 is independently selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, halo, NH 2 , NH(C 1-6 alkyl), and N(C 1-6 alkyl) 2 ;

each R 9 is independently selected from the group consisting of C 1-6 alkyl, CN, SO 2 R 6 , NH 2 , NH(C 1-6 alkyl), and N(C 1-6 alkyl) 2 ;

m is 0, 1, 2, or 3;

n is 0, 1, 2, or 3; and

p is 0, 1, 2, or 3.

18 . The compound of claim 17 , wherein the compound of Formula III is a compound selected from

or a pharmaceutically acceptable salt thereof.

19 . The compound of claim 1 wherein the compound binds to one or more amino acids of Y143, R147, F257, Y258, H260, E263, V264, L272, L275, I276, C279, F299, G328, L331, L332, L335, and C514 of a NLRP3 amino acid sequence of SEQ ID NO: 1.

20 . A pharmaceutical composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

21 . A method of inhibiting NLRP3 inflammasome in a subject in need thereof comprising administering to the subject a therapeutically effective amount of a compound according to claim 1 .

22 . A method of treating obesity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

23 . A method of improving lipid metabolism in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

24 . A method of treating an ocular disease in a subject in need thereof comprising administering to the subject a therapeutically effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

25 . A method of treating gout in a subject in need thereof comprising administering to the subject a therapeutically effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

26 . The compound of claim 1 , wherein the compound of Formula I is selected from the group consisting of

or a pharmaceutically acceptable salt thereof.

27 . The compound of claim 1 , wherein the compound of Formula I is

or a pharmaceutically acceptable salt thereof.

28 . The compound of claim 1 , wherein the compound of Formula I is

or a pharmaceutically acceptable salt thereof.

29 . The compound of claim 1 , wherein the compound of Formula I is

or a pharmaceutically acceptable salt thereof.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 20, 2025

From: HARTMAN, GEORGE; WANG, YAN; HUMPHRIES, PAUL; MONTGOMERY, RUSTY; GEYER, MATTHIAS; WILHELMSEN, KEVIN; YAN, SHIJUN

To: BIOAGE LABS, INC.

Reel/Frame 072607/0947 →

Continuity (5)

Provisional Application 63708034 · Oct 16, 2024

Provisional Application 63669006 · Jul 9, 2024

Provisional Application 63656967 · Jun 6, 2024

Provisional Application 63570087 · Mar 26, 2024

Related Publication 20250304581A1 · Oct 2, 2025

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