IP Library › Granted Patent US 12,195,427
Granted Patent B2
US 12,195,427 · App. 18/060,456 · Granted Jan 14, 2025

MASP-2 inhibitors and methods of use

Inventors: Neil S. Cutshall (Snohomish, WA); Jennifer Lynn Gage (Kenmore, WA); Franz A. Gruswitz (Bellevue, WA); Juhienah Khalaf (Hamilton, MT); Thomas L. Little (Seattle, WA); Markus Metz (Bellevue, WA); Jeremiah H. Nguyen (Kent, WA); Peter Kurt Nollert von Specht (Bainbridge Island, WA); Jennifer Tsoung (Seattle, WA); Michael Cicirelli (Kirkland, WA); Sara Rebecca Goldstein (Seattle, WA); Santosh Kumar Keshipeddy (Bellevue, WA); Do Yeon Kwon (Seattle, WA); Robert Huerta Lemus (Seattle, WA); Sudheer Babu Vaddela (Bellevue, WA)
Assignee: Omeros Corporation
C07D205/04C07C235/88C07C251/24C07D207/16C07D207/24C07D207/36C07D211/60C07D213/73C07D213/81C07D217/14C07D231/44C07D233/64C07D235/30C07D239/94C07D239/96C07D249/08C07D257/04C07D277/56C07D295/033C07D295/135C07D295/26C07D401/06C07D401/12C07D401/14C07D403/06C07D403/12C07D409/10C07D409/14C07D413/12C07D413/14C07D417/12C07D417/14C07D471/04C07D471/06C07D495/04
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Quick Facts
Patent No.
US 12,195,427
App. No.
18/060,456
Granted
Jan 14, 2025
Kind
B2
Abstract

The present disclosure provides, inter alia, compounds with MASP-2 inhibitory activity, compositions of such compounds and methods of making and using such compounds.

Claims (47)

1. A compound of Formula (I-4):

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

Cy 1A is unsubstituted or substituted 5-10 membered heteroaryl; wherein the ring atoms of the 5-10 membered heteroaryl forming Cy 1A consist of carbon atoms and 1, 2, or 3 heteroatoms selected from O, N and S; wherein the substituted 5-10 membered heteroaryl forming Cy 1A is substituted with 1, 2, 3, 4 or 5 substituents each independently selected from R Cy1A , halogen, C 1-6 haloalkyl, CN, OR a11 , SR a11 , C(O)R b11 , C(O)NR c11 R d11 , C(O)OR a11 , OC(O)R b11 , OC(O)NR c11 R d11 , NR c11 R d11 , NR c11 C(O)R b11 , NR c11 C(O)NR c11 R d11 , NR c11 C(O)OR a11 , C(═NR e11 ) NR c11 R d11 , C(═NOR a11 )NR c11 R d11 , C(═NOC(O)R b11 ) NR c11 R d11 , NR c11 C(═NR e11 )NR c11 R d11 , S(O)R b11 , S(O)NR c11 R d11 , S(O) 2 R b11 , NR c11 S(O) 2 R b11 , S(O) 2 NR c11 R d11 and oxo;

each R Cy1A is independently selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, 5-10 membered heteroaryl, C 3-10 cycloalkyl and 4-10 membered heterocycloalkyl, wherein the ring atoms of the 5-10 membered heteroaryl or 4-10-membered heterocycloalkyl forming R Cy1A consist of carbon atoms and 1, 2, 3 or 4 heteroatoms selected from O, N and S, wherein each C 1-6 alkyl, C 2-6 alkenyl, or C 2-6 alkynyl forming R Cy1A is independently unsubstituted or substituted with 1, 2 or 3 substituents independently selected from halogen, CN, OR a11 , SR a11 , C(O)R b11 , C(O)NR c11 R d11 , C(O)OR a11 , OC(O)R b11 , OC(O)NR c11 R d11 , NR c11 R d11 , NR c11 C(O)R b11 , S(O)R b11 , S(O)NR c11 R d11 , S(O) 2 R b11 , NR c11 S(O) 2 R b11 , S(O) 2 NR c11 R d11 and oxo, and wherein each C 6-10 aryl, 5-10 membered heteroaryl, C 3-10 cycloalkyl and 4-10 membered heterocycloalkyl forming R Cy1A is independently unsubstituted or substituted with 1, 2 or 3 substituents independently selected from halogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, CN, OR a11 , SR a11 , C(O)R b11 , C(O)NR c11 R d11 , C(O)OR a11 , OC(O)R b11 , OC(O)NR c11 R d11 , NR c11 R d11 , NR c11 C(O)R b11 , NR c11 C(O) NR c11 R d11 , NR c11 C(O)OR a11 , C(═NR e11 )NR c11 R d11 , NR c11 C(═NR e11 ) NR c11 R d11 , S(O)R b11 , S(O)NR c11 R d11 , S(O) 2 R b11 , NR c11 S(O) 2 R b11 , S(O) 2 NR c11 R d11 and oxo;

R 11 is H or C 1-6 alkyl, C 6-10 aryl-C 1-6 alkyl or 5-10 membered heteroaryl-C 1-6 alkyl, wherein the C 1-6 alkyl forming R 11 is unsubstituted or substituted by 1, 2 or 3 substituents independently selected from halogen, CN, OR a11 , SR a11 , C(O)R b11 , C(O)NR c11 R d11 , C(O)OR c11 , OC(O)R b11 , OC(O)NR c11 R d11 , NR c11 R d11 , NR c11 C(O)R b11 , NR c11 C(O)NR c11 R d11 , NR c11 C(O)OR a11 , NR c11 C(═NR e11 )NR c11 R d11 , S(O)R b11 , S(O)NR c11 R d11 , S(O) 2 R b11 , NR c11 S(O) 2 R b11 , S(O) 2 NR c11 R d11 and oxo, and wherein the C 6-10 aryl-C 1-6 alkyl or 5-10 membered heteroaryl-C 1-6 alkyl forming R 11 is unsubstituted or substituted by 1, 2 or 3 substituents independently selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, CN, OR a11 , SR a11 , C(O)R b11 , C(O)NR c11 R d11 , C(O)OR a11 , OC(O)R b11 , OC(O)NR c11 R d11 , NR c11 R d11 , NR c11 C(O)R b11 , NR c11 C(O)NR c11 R d11 , NR c11 C(O)OR a11 , C(═NR e11 )NR c11 R d11 , NR c11 C(═NR e11 ) NR c11 R d11 S(O)R b11 , S(O)NR c11 R d11 , S(O) 2 R b11 , NR c11 S(O) 2 R b11 , S(O) 2 NR c11 R d11 and oxo;

R 12 is H or C 1-6 alkyl;

each R 13 is independently Cy 1B , (CR 13A R 13B ) n3 Cy 1B , (C 1-6 alkylene)Cy 1B , (C 2-6 alkenylene) Cy 1B , (C 2-6 alkynylene) Cy 1B or OCy 1B , wherein the C 1-6 alkylene, C 2-6 alkenylene, or C 2-6 alkynylene component of R 13 is unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents each independently selected from the group consisting of halogen, CN, OR a11 , SR a11 , C(O)R b11 , C(O)NR c11 R d11 , C(O)OR a11 , OC(O)R b11 , OC(O)NR c11 R d11 , NR c11 R d11 , NR c11 C(O)R b11 , NR c11 C(O)NR c11 R d11 , NR c11 C(O)OR a11 , C(═NR e11 ) NR c11 R d11 , NR c11 C(═NR e11 ) NR c11 R d11 , S(O)R b11 , S(O)NR c11 R d11 , S(O) 2 R b11 , NR c11 S(O) 2 R b11 , S(O) 2 NR c11 R d11 and oxo;

each R 14 is independently selected from H and C 1-6 alkyl;

R 15 is selected from H, R 13 , C 1-6 alkyl and OH;

n3 is 0, 1 or 2;

each R 13A is independently H or C 1-6 alkyl, and

each R 13B is independently H or C 1-6 alkyl, or

R 13A and R 13B attached to the same carbon atom, and independently of any other R 13A and R 13B groups, together may form —(CH 2 ) 2-5 —, thereby forming a 3-6 membered cycloalkyl ring;

Cy 1B is unsubstituted or substituted C 6-10 aryl, unsubstituted or substituted 5-10 membered heteroaryl, unsubstituted or substituted C 3-10 cycloalkyl, or unsubstituted or substituted 4-10 membered heterocycloalkyl; wherein the ring atoms of the 5-10 membered heteroaryl or 4-10 membered heterocycloalkyl forming Cy 1B consist of carbon atoms and 1, 2 or 3 heteroatoms selected from O, N and S,

wherein the substituted C 6-10 aryl, substituted 5-10 membered heteroaryl, substituted C 3-10 cycloalkyl or substituted 4-10 membered heterocycloalkyl forming Cy 1B are substituted with 1, 2, 3, 4 or 5 substituents each independently selected from R Cy1B , halogen, C 1-6 haloalkyl, CN, OR a11 , SR a11 , C(O)R b11 , C(O)NR c11 R d11 , C(O)OR a11 , OC(O)R b11 , OC(O)NR c11 R d11 , NR c11 R d11 , NR c11 C(O)OR b11 , NR c11 C(O)NR c11 R d11 , NR c11 C(O)OR a11 , C(═NR e11 ) NR c11 R d11 , C(═NOR a11 )NR c11 R d11 , C(═NOC(O)R b11 )NR c11 R d11 , C(═NR e11 )NR c11 C(O)OR a11 , NR c11 C(═NR e11 ) NR c11 R d11 , S(O)R b11 , S(O)NR c11 R d11 , S(O) 2 R b11 , NR c11 S(O) 2 R b11 , S(O) 2 NR c11 R d11 and oxo;

each R Cy1B is independently selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, 5-10 membered heteroaryl, C 3-10 cycloalkyl and 4-10 membered heterocycloalkyl, wherein the ring atoms of the 5-10 membered heteroaryl or 4-10 membered heterocycloalkyl forming R Cy1B consist of carbon atoms and 1, 2 or 3 heteroatoms selected from O, N and S; wherein each C 1-6 alkyl, C 2-6 alkenyl, or C 2-6 alkynyl forming R Cy1B is independently unsubstituted or substituted with 1, 2 or 3 substituents independently selected from halogen, CN, OR a11 , SR a11 , C(O)R b11 , C(O)NR c11 R d11 , C(O)OR a11 , OC(O)R b11 , OC(O)NR c11 R d11 , NR c11 R d11 , NR c11 C(O) Rb11 , NR c11 C(O)NR c11 R d11 , NR c11 C(O) OR a11 , C(═NR e11 )NR c11 R d11 , NR c11 C(═NR e11 )NR c11 R d11 , S(O)R b11 , S(O)NR c11 R d11 , S(O) 2 R b11 , NR c11 S(O) 2 R b11 , S(O) 2 NR c11 R d11 , oxo, and phenyl; and wherein each C 6-10 aryl, 5-10 membered heteroaryl, C 3-10 cycloalkyl and 4-10 membered heterocycloalkyl forming R Cy1B is independently unsubstituted or substituted with 1, 2 or 3 substituents independently selected from halogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, CN, OR a11 , SR a11 , C(O)R b11 , C(O)NR c11 R d11 , C(O)OR a11 , OC(O)R b11 , OC(O)NR c11 R d11 , NR c11 R d11 , NR c11 C(O)R b11 , NR c11 C(O)NR c11 R d11 , NR c11 C(O)OR a11 , C(═NR e11 ) NR c11 R d11 , NR c11 C(═NR e11 ) NR c11 R d11 , S(O)R b11 , S(O)NR c11 R d11 , S(O) 2 R b11 , NR c11 S(O) 2 R b11 , S(O) 2 NR c11 R d11 and oxo;

R 16 is H, Cy 1C , C 1-6 alkyl, C 2-6 alkenyl, or C 2-6 alkynyl, wherein the C 1-6 alkyl, C 2-6 alkenyl, or C 2-6 alkynyl forming R 16 is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents selected from the group consisting of Cy 1C , halogen, CN, OR a11 , SR a11 , C(O)R b11 , C(O)NR c11 R d11 , C(O)OR a11 , OC(O)R b11 , OC(O)NR c11 R d11 , NR c11 R d11 , NR c11 C(O)R b11 , NR c11 C(O)NR c11 R d11 , NR c11 C(O)OR a11 , C(═NR e11 )NR c11 R d11 , NR c11 C(═NR e11 ) NR c11 R d11 , S(O)R b11 , S(O)NR c11 R d11 , S(O) 2 R b11 , NR c11 S(O) 2 R b11 , S(O) 2 NR c11 R d11 and oxo, provided that no more than one of the substituents of R 16 is Cy 1C ;

Cy 1C is unsubstituted or substituted C 6-10 aryl, unsubstituted or substituted 5-10 membered heteroaryl, unsubstituted or substituted C 3-10 cycloalkyl, or unsubstituted or substituted 4-10 membered heterocycloalkyl; wherein the ring atoms of the 5-10 membered heteroaryl or 4-10 membered heterocycloalkyl forming Cy 1C consist of carbon atoms and 1, 2 or 3 heteroatoms selected from O, N and S,

wherein the substituted C 6-10 aryl, substituted 5-10 membered heteroaryl, substituted C 3-10 cycloalkyl or substituted 4-10 membered heterocycloalkyl forming Cy 1C are substituted with 1, 2, 3, 4 or 5 substituents each independently selected from R Cy1C , halogen, C 1-6 haloalkyl, CN, OR a11 , SR a11 , C(O)R b11 , C(O)NR c11 R d11 , C(O)OR a11 , OC(O)R b11 , OC(O)NR c11 R d11 , NR c11 R d11 , NR c11 C(O)R b11 , NR c11 C(O)NR c11 R d11 , C(═NR e11 ) NR c11 R d11 , C(═NOR a11 )NR c11 R d11 , C(═NOC(O)R b11 )NR c11 R d11 , C(═NR e11 )NR c11 C(O)OR a11 , NR c11 C(═NR e11 )NR c11 R d11 , S(O)R b11 , S(O)NR c11 R d11 , S(O) 2 R b11 , NR c11 S(O) 2 R b11 , S(O) 2 NR c11 R d11 and oxo;

each R Cy1C is independently selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, 5-10 membered heteroaryl, C 3-10 cycloalkyl and 4-10 membered heterocycloalkyl, wherein the ring atoms of the 5-10 membered heteroaryl or 4-10 membered heterocycloalkyl forming R Cy1C consist of carbon atoms and 1, 2 or 3 heteroatoms selected from O, N and S; wherein each C 1-6 alkyl, C 2-6 alkenyl, or C 2-6 alkynyl forming R Cy1C is independently unsubstituted or substituted with 1, 2 or 3 substituents independently selected from halogen, CN, OR a11 , SR a11 , C(O)R b11 , C(O)NR c11 R d11 , C(O)OR a11 , OC(O)R b11 , OC(O)NR c11 R d11 , NR c11 R d11 , NR c11 C(O)R b11 , NR c11 C(O)NR c11 R d11 , NR c11 C(O)OR a11 , C(═NR e11 )NR c11 R d11 , NR c11 C(═NR e11 ) NR c11 R d11 , S(O)R b11 , S(O)NR c11 R d11 , S(O) 2 R b11 , NR c11 S(O) 2 R b11 , S(O) 2 NR c11 R d11 and oxo; and wherein each C 6-10 aryl, 5-10 membered heteroaryl, C 3-10 cycloalkyl and 4-10 membered heterocycloalkyl forming R Cy1C is independently unsubstituted or substituted with 1, 2 or 3 substituents independently selected from halogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, CN, OR a11 , SR a11 , C(O)R b11 , C(O)NR c11 R d11 , C(O)OR a11 , OC(O)R b11 , OC(O)NR c11 R d11 , NR c11 R d11 , NR c11 C(O)R b11 , NR c11 C(O)NR c11 R d11 , NR c11 C(O)OR a11 , C(═NR e11 ) NR c11 R d11 , NR c11 C(═NR e11 ) NR c11 R d11 , S(O)R b11 , S(O)NR c11 R d11 , S(O) 2 R b11 , NR c11 S(O) 2 R b11 , S(O) 2 NR c11 R d11 and oxo;

R a11 and R b11 are each independently selected from H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-7 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-3 alkyl, 5-10 membered heteroaryl-C 1-3 alkyl, C 3-7 cycloalkyl-C 1-3 alkyl and 4-10 membered heterocycloalkyl-C 1-3 alkyl, wherein said C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-7 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-3 alkyl, 5-10 membered heteroaryl-C 1-3 alkyl, C 3-7 cycloalkyl-C 1-3 alkyl and 4-10 membered heterocycloalkyl-C 1-3 alkyl forming R a11 and R b11 are each unsubstituted, or substituted with 1, 2, 3, 4 or 5 substituents independently selected from C 1-6 alkyl, halo, CN, OR a12 , SR a12 , C(O)R b12 , C(O)NR c12 R d12 , C(O)OR a12 , OC(O)R b12 , OC(O)NR c12 R d12 , NR c12 R d12 , NR c12 C(O)R b12 , NR c12 C(O)NR c12 R d12 , NR c12 C(O)OR a12 , C(═NR e12 )NR c12 R d12 , NR c12 C(═NR e12 ) NR c12 R d12 , S(O)R b12 , S(O)NR c12 R d12 , S(O) 2 R b12 , NR c12 S(O) 2 R b12 , S(O) 2 NR c12 R d12 and oxo;

R c11 and R d11 are each independently selected from H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-7 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-3 alkyl, 5-10 membered heteroaryl-C 1-3 alkyl, C 3-7 cycloalkyl-C 1-3 alkyl and 4-10 membered heterocycloalkyl-C 1-3 alkyl, wherein said C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 3-7 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C 6-10 aryl-C 1-3 alkyl, 5-10 membered heteroaryl-C 1-3 alkyl, C 3-7 cycloalkyl-C 1-3 alkyl and 4-10 membered heterocycloalkyl-C 1-3 alkyl forming R c11 and R b11 are each unsubstituted, or substituted with 1, 2, 3, 4 or 5 substituents independently selected from C 1-6 alkyl, halo, CN, OR a12 , SR a12 , C(O)R b12 , C(O)NR c12 R d12 , C(O)OR a12 , OC(O)R b12 , OC(O)NR c12 R d12 , NR c12 R d12 , NR c12 C(O)R b12 , NR c12 C(O)NR c12 R d12 , NR c12 C(O)OR a12 , C(═NR e12 )NR c12 R d12 , NR c12 C(═NR e12 )NR c12 R d12 , S(O)R b12 , S(O)NR c12 R d12 , S(O) 2 R b12 , NR c12 S(O) 2 R b12 , S(O) 2 NR c12 R d12 and oxo, or

R c11 and R d11 attached to the same N atom, together with the N atom to which they are both attached, form a 4-, 5-, 6- or 7-membered heterocycloalkyl group or 5-membered heteroaryl group, each unsubstituted, or substituted with 1, 2 or 3 substituents independently selected from C 1-6 alkyl, halo, CN, OR a12 , SR a12 , C(O)R b12 , C(O)NR c12 R d12 , C(O)OR a12 , OC(O)R b12 , OC(O)NR c12 R d12 , NR c12 R d12 , NR c12 C(O)R b12 , NR c12 C(O)NR c12 R d12 , NR c12 C(O)OR a12 , C(═NR e12 )NR c12 R d12 , NR c12 C(═NR e12 )NR c12 R d12 , S(O)R b12 , S(O)NR c12 R d12 , S(O) 2 R b12 , NR c12 S(O) 2 R b12 , S(O) 2 NR c12 R d12 and oxo;

R a12 and R b12 are each independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, phenyl, C 3-7 cycloalkyl, 5-6 membered heteroaryl, 4-7 membered heterocycloalkyl, phenyl-C 1-3 alkyl, 5-6 membered heteroaryl-C 1-3 alkyl, C 3-7 cycloalkyl-C 1-3 alkyl and 4-7 membered heterocycloalkyl-C 1-3 alkyl, wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, phenyl, C 3-7 cycloalkyl, 5-6 membered heteroaryl, 4-7 membered heterocycloalkyl, phenyl-C 1-3 alkyl, 5-6 membered heteroaryl-C 1-3 alkyl, C 3-7 cycloalkyl-C 1-3 alkyl and 4-7 membered heterocycloalkyl-C 1-3 alkyl forming R a12 and R b12 are each unsubstituted, or substituted with 1, 2 or 3 substituents independently selected from OH, CN, amino, NH(C 1-6 alkyl), N(C 1-6 alkyl) 2, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 haloalkyl, C 1-6 haloalkoxy and oxo;

R c12 and R d12 are each independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, phenyl, C 3-7 cycloalkyl, 5-6 membered heteroaryl, 4-7 membered heterocycloalkyl, phenyl-C 1-3 alkyl, 5-6 membered heteroaryl-C 1-3 alkyl, C 3-7 cycloalkyl-C 1-3 alkyl and 4-7 membered heterocycloalkyl-C 1-3 alkyl, wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, phenyl, C 3-7 cycloalkyl, 5-6 membered heteroaryl, 4-7 membered heterocycloalkyl, phenyl-C 1-3 alkyl, 5-6 membered heteroaryl-C 1-3 alkyl, C 3-7 cycloalkyl-C 1-3 alkyl and 4-7 membered heterocycloalkyl-C 1-3 alkyl forming R c12 and R d12 are each unsubstituted, or substituted with 1, 2 or 3 substituents independently selected from OH, CN, amino, NH(C 1-6 alkyl), N(C 1-6 alkyl) 2, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 haloalkyl, C 1-6 haloalkoxy and oxo, or

R c12 and R d12 attached to the same N atom, together with the N atom to which they are both attached, form a 4-, 5-, 6- or 7-membered heterocycloalkyl group or 5-membered heteroaryl group, each of which is unsubstituted or substituted with 1, 2 or 3 substituents independently selected from OH, CN, amino, NH(C 1-6 alkyl), N(C 1-6 alkyl) 2, halo, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 haloalkyl, C 1-6 haloalkoxy and oxo; and

R e11 and R e12 are each, independently, H, CN or NO 2 .

2. The compound or salt thereof of claim 1 , wherein Cy 1A is substituted with at least one OR a11 , C(═NR e11 ) NR c11 R d11 , C(═NOR a11 ) NR c11 R d11 , C(═NOC(O)R b11 ) NR c11 R d11 , or C(═NR e11 )NR c11 C(O)OR a11 .

3. The compound or salt thereof of claim 1 , wherein Cy 1A is unsubstituted or substituted pyridin-3-yl, 1H-pyrrolo[2,3-b]pyridine-5-yl, or 1H-benzo[d]imidazol-6-yl.

4. The compound or salt thereof of claim 1 , wherein Cy 1A is of any one of the following formulae:

wherein each R Cy1A attached to a carbon atom is independently C 1-6 alkyl, halogen, or amino, and each R Cy1A attached to a nitrogen atom is H or C 1-6 alkyl.

5. The compound or salt thereof of claim 1 , wherein R 11 is H or C 1-6 alkyl.

6. The compound or salt thereof of claim 1 , wherein R 11 is methyl.

7. The compound or salt thereof of claim 1 , wherein R 12 is H or C 1-6 alkyl.

8. The compound or salt thereof of claim 1 , wherein the compound is according to Formula (I-8):

9. The compound or salt thereof of claim 1 , wherein the compound is according to any one of the following Formulae (I-8a) to (I-8z):

10. The compound or salt thereof of claim 9 , wherein R 13 is Cy 1B , CH 2 Cy 1B , CH 2 CH 2 Cy 1B , or OCy 1B , and wherein Cy 1B is substituted or unsubstituted C 6-10 aryl or substituted or unsubstituted 5-10 membered heteroaryl.

11. The compound or salt thereof of claim 10 , wherein Cy 1B is substituted with 1, 2, 3, 4 or 5 substituents each independently selected from R Cy1B , halogen, C 1-6 haloalkyl, CN, OR a11 , NR c11 C(O)R b11 , C(O)NR c11 R d11 ;

wherein each R Cy1B is independently selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-10 cycloalkyl, and C 6-10 aryl or 5-10 membered heteroaryl, wherein each C 1-6 alkyl, C 6-10 aryl, or 5-10 membered heteroaryl forming R Cy1B is unsubstituted or substituted with 1, 2 or 3 substituents independently selected from halogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, NR c11 R d11 , CN, C(O)NR c11 R d11 , CH 2 NR c11 R d11 , and haloalkyl.

12. The compound or salt thereof of claim 1 , wherein R 13 is a group selected from:

wherein R Cy1B is H, C 1-6 alkyl or halogen.

13. The compound or salt thereof of claim 1 , wherein each R 14 is hydrogen.

14. The compound or salt thereof of claim 1 , wherein R 15 is hydrogen.

15. The compound or salt thereof of claim 1 , wherein R 16 is hydrogen, unsubstituted or substituted C 1-6 alkyl, unsubstituted or substituted C 2-6 alkenyl, or unsubstituted or substituted C 2-6 alkynyl.

16. The compound of claim 1 , having a structure selected from the group consisting of:

17. A pharmaceutical composition comprising a compound of claim 1 , or a stereoisomer, tautomer, or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or excipient.

18. A method for inhibiting MASP-2 in a subject in need thereof, comprising administering to the subject a compound of claim 1 , or a stereoisomer, tautomer, or pharmaceutically acceptable salt thereof, in an amount effective to inhibit MASP-2.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Nov 25, 2025
From: WILMINGTON SAVINGS FUND SOCIETY, FSB
To: OMEROS CORPORATION
Reel/Frame 073705/0970 →
CORRECTIVE ASSIGNMENT TO CORRECT THE CORRECT THE BOX TITLED"THIS DOCUMENT SERVES AS AN OATH/DECLARATION (37 CFR 1.63)" WAS ERRONEOUSLY CHECKED AND THIS BOX SHOULD NOT HAVE BEEN CHECKED, PREVIOUSLY RECORDED AT REEL: 67607 FRAME: 108. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY INTEREST. Recorded Dec 11, 2024
From: OMEROS CORPORATION
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS COLLATERAL AGENT
Reel/Frame 069715/0719 →
SECURITY INTEREST Recorded Jun 3, 2024
From: OMEROS CORPORATION
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS COLLATERAL AGENT
Reel/Frame 067607/0108 →
Continuity (7)
Continuation 16425791 · May 29, 2019
Continuation PCTUS2019034220 · May 28, 2019
Provisional Application 62677472 · May 29, 2018
Provisional Application 62677538 · May 29, 2018
Provisional Application 62677495 · May 29, 2018
Provisional Application 62677514 · May 29, 2018
Related Publication 20230145071A1 · May 11, 2023
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