Granted Patent B2

US 12,559,508 · App. 19/076,644 · Granted Feb 24, 2026

Inventors: Michael H Reutershan (Acton, MA); Laurie B Schenkel (Belmont, MA); Meredeth A Mcgowan (Bedford, MA); Timothy J Guzi (Sudbury, MA); John R Butler (Thousand Oaks, CA); Haoxuan Wang (Somerville, MA); Cen Gao (Carmel, IN); Yonghong Bai (Lexington, MA)

Assignee: MOMA Therapeutics, Inc.

C07D513/04A61K31/444A61K31/497A61K31/501A61K31/506C07D417/14C07D519/00

Abstract

Claims (32)

1 . A compound of Formula (I-F):

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

X 1 is N and X 2 is S, or X 1 is S and X 2 is N;

each R a independently is oxo, halo, cyano, —OR a1 , —N(R a1 ) 2 , —C(O)R a1 , —C(O)N(R a1 ) 2 , —C(O)OR a1 , —S(O) 2 N(R a1 ) 2 , —S(O) 2 (R a1 ), C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 10 cycloalkyl, C 6 -C 10 aryl, 5- to 10-membered heteroaryl, or 3- to 10-membered heterocycloalkyl, wherein the C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 10 cycloalkyl, C 6 -C 10 aryl, 5- to 10-membered heteroaryl, or 3- to 10-membered heterocycloalkyl is optionally substituted with one or more R a1 ;

p is 0 to 4;

each R a1 independently is H, oxo, halo, cyano, —OH, —NH 2 , —C(O)(C 1 -C 6 alkyl), —C(O)(C 3 -C 10 cycloalkyl), C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 3 -C 10 cycloalkyl, 3- to 10-membered heterocycloalkyl, C 6 -C 10 aryl, or 5- to 10-membered heteroaryl, wherein the —C(O)(C 3 -C 10 cycloalkyl), C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 3 -C 10 cycloalkyl, 3- to 10-membered heterocycloalkyl, C 6 -C 10 aryl, or 5- to 10-membered heteroaryl is optionally substituted with one or more R a2 ;

each R a2 independently is oxo, halo, cyano, —OH, —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , C 1 -C 6 alkyl optionally substituted with C 1 -C 6 alkoxy or —OH, C 3 -C 10 cycloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, 3- to 10-membered heterocycloalkyl optionally substituted with oxo, or 5- to 10-membered heteroaryl;

R 3 is C 6 -C 10 aryl or 5- to 10-membered heteroaryl, wherein the C 6 -C 10 aryl or 5- to 10-membered heteroaryl is substituted with one or more R 3a ;

each R 3a independently is halo, cyano, —OH, —NH 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 10 cycloalkyl, 3- to 10-membered heterocycloalkyl, C 6 -C 10 aryl, or 5- to 10-membered heteroaryl, wherein the C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 10 cycloalkyl, 3- to 10-membered heterocycloalkyl, C 6 -C 10 aryl, or 5- to 10-membered heteroaryl is optionally substituted with one or more R 3a1 ; and

each R 3a1 independently is oxo, halo, cyano, —OH, —C(O)(C 1 -C 6 alkyl), —C(O)(O—(C 1 -C 6 alkyl)), C 1 -C 6 alkyl optionally substituted with C 3 -C 10 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxy, —O(C 1 -C 6 haloalkyl), C 3 -C 10 cycloalkyl, C 6 -C 10 aryl, or 5- to 10-membered heteroaryl.

2 . The compound of claim 1 , wherein R 3 is 5- to 6-membered heteroaryl substituted with one or more R 3a .

3 . The compound of claim 1 , wherein each R 3a independently is C 1 -C 6 alkyl or 5- to 10-membered heteroaryl, wherein the C 1 -C 6 alkyl or 5- to 10-membered heteroaryl is optionally substituted with one or more R 3a1 .

4 . The compound of claim 1 , wherein each R 3a1 independently is halo or C 1 -C 6 alkoxy.

5 . The compound of claim 1 , wherein R 3 is

6 . The compound of claim 1 , wherein each R a independently is —C(O)R a1 .

7 . The compound of claim 1 , wherein each R a1 is 5- to 6-membered heteroaryl substituted with one or more R a2 .

8 . The compound of claim 1 , wherein each R a2 independently is C 1 -C 6 haloalkyl or C 1 -C 6 alkoxy.

9 . The compound of claim 1 , wherein p is 0.

10 . The compound of claim 1 , wherein the compound is of Formula (I-Fa), (I-Fb), (I-Fb′), (I-Fc), or (I-Fc′):

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

11 . The compound of claim 1 , wherein the compound is selected from:

or a pharmaceutically acceptable salt thereof.

12 . The compound of claim 1 , wherein the compound is selected from:

or a pharmaceutically acceptable salt thereof.

13 . A pharmaceutical composition comprising the compound of claim 1 , or a pharmaceutically acceptable salt thereof, and one or more of a diluent, a carrier, an excipient, an adjuvant, and a binder.

14 . A pharmaceutical composition comprising the compound of claim 11 , or a pharmaceutically acceptable salt thereof, and one or more of a diluent, a carrier, an excipient, an adjuvant, and a binder.

15 . A pharmaceutical composition comprising the compound of claim 12 , or a pharmaceutically acceptable salt thereof, and one or more of a diluent, a carrier, an excipient, an adjuvant, and a binder.

16 . The compound of claim 1 , wherein each R a1 independently is 5- to 6-membered heteroaryl optionally substituted with one or more R a2 .

17 . The compound of claim 1 , wherein each R a2 independently is —OCH 3 or —CF 3 .

18 . The compound of claim 1 , wherein each R a independently is

19 . The compound of claim 1 , wherein each R 3a independently is methyl or 5- to 6-membered heteroaryl substituted with one or more R 3a1 .

20 . The compound of claim 1 , wherein each R 3a1 independently is —Cl or —OCH 3 .

Assignments (1)

Continuity (4)

References Cited (167)