IP Library Granted Patent US 10,981,901
Granted Patent B1
US 10,981,901 · App. 16/091,189 · Granted Apr 20, 2021

Heterocyclic amides useful as protein modulators

Inventors: Joseph J. Romano (Collegeville, PA); Jianxing Kang (Collegeville, PA)
Assignee: GlaxoSmithKline Intellectual Property Development Limited
C07D413/14C07D403/14
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Quick Facts
Patent No.
US 10,981,901
App. No.
16/091,189
Granted
Apr 20, 2021
Kind
B1
Abstract

Disclosed are compounds having the formula: wherein q, r, s, A, B, C, R A1 , R A2 , R B1 , R B2 , R C1 , R C2 , R 3 , R 4 , R 5 , R 6 , R 14 , R 15 , R 16 , and R 17 , are as defined herein, or a tautomer thereof, or a salt, particularly a pharmaceutically acceptable salt, thereof.

Claims (27)

1. A compound which is (E)-1-(4-(5-carbamoyl-2-(1-ethyl-3-methyl-1H-pyrazole-5-carboxamido)-1H-benzo[d]imidazol-1-yl)but-2-en-1-yl)-2-(1-ethyl-3-methyl-1H-pyrazole-5-carboxamido)-7-(3-morpholinopropoxy)-1H-benzo[d]imidazole-5-carboxamide

having the structure of

or a tautomer thereof,

or a pharmaceutically acceptable salt thereof,

or a hydrate thereof.

2. The compound according to claim 1 , which is a pharmaceutically acceptable salt of (E)-1-(4-(5-carbamoyl-2-(1-ethyl-3-methyl-1H-pyrazole-5-carboxamido)-1H-benzo[d]imidazol-1-yl)but-2-en-1-yl)-2-(1-ethyl-3-methyl-1H-pyrazole-5-carboxamido)-7-(3-morpholinopropoxy)-1H-benzo[d]imidazole-5-carboxamide, or a tautomer thereof.

3. The compound according to claim 1 , which is (E)-1-(4-(5-carbamoyl-2-(1-ethyl-3-methyl-1H-pyrazole-5-carboxamido)-1H-benzo[d]imidazol-1-yl)but-2-en-1-yl)-2-(1-ethyl-3-methyl-1H-pyrazole-5-carboxamido)-7-(3-morpholinopropoxy)-1H-benzo[d]imidazole-5-carboxamide, or a tautomer thereof.

4. The compound according to claim 1 , which is (E)-1-((E)-4-((E)-5-carbamoyl-2-((1-ethyl-3-methyl-1H-pyrazole-5-carbonyl)imino)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)but-2-en-1-yl)-2-((1-ethyl-3-methyl-1H-pyrazole-5-carbonyl)imino)-7-(3-morpholinopropoxy)-2,3-dihydro-1H-benzo[d]imidazole-5-carboxamide having the structure of

or a pharmaceutically acceptable salt thereof.

5. A pharmaceutical composition comprising a compound which is (E)-1-(4-(5-carbamoyl-2-(1-ethyl-3-methyl-1H-pyrazole-5-carboxamido)-1H-benzo[d]imidazol-1-yl)but-2-en-1-yl)-2-(1-ethyl-3-methyl-1H-pyrazole-5-carboxamido)-7-(3-morpholinopropoxy)-1H-benzo[d]imidazole-5-carboxamide having the structure of

or a tautomer thereof,

or a pharmaceutically acceptable salt thereof,

or a hydrate thereof, and

a pharmaceutically acceptable excipient.

6. The pharmaceutical composition according to claim 5 , wherein the compound is

(E)-1-((E)-4-((E)-5-carbamoyl-2-((1-ethyl-3-methyl-1H-pyrazole-5-carbonyl)imino)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)but-2-en-1-yl)-2-((1-ethyl-3-methyl-1H-pyrazole-5-carbonyl)imino)-7-(3-morpholinopropoxy)-2,3-dihydro-1H-benzo[d]imidazole-5-carboxamide having the structure of

or a pharmaceutically acceptable salt thereof.

7. A method of treating a STING-mediated disease or disorder comprising administering a therapeutically effective amount of a compound which is (E)-1-(4-(5-carbamoyl-2-(1-ethyl-3-methyl-1H-pyrazole-5-carboxamido)-1H-benzo[d]imidazol-1-yl)but-2-en-1-yl)-2-(1-ethyl-3-methyl-1H-pyrazole-5-carboxamido)-7-(3-morpholinopropoxy)-1H-benzo[d]imidazole-5-carboxamide

having the structure of

or a tautomer thereof,

or a pharmaceutically acceptable salt thereof,

or a hydrate thereof,

to a human in need thereof.

8. The method according to claim 7 , wherein the compound is (E)-1-((E)-4-((E)-5-carbamoyl-2-((1-ethyl-3-methyl-1H-pyrazole-5-carbonyl)imino)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)but-2-en-1-yl)-2-((1-ethyl-3-methyl-1H-pyrazole-5-carbonyl)imino)-7-(3-morpholinopropoxy)-2,3-dihydro-1H-benzo[d]imidazole-5-carboxamide having the structure of

or a pharmaceutically acceptable salt thereof.

9. The method according to claim 7 , wherein the STING-mediated disease or disorder is an infectious disease.

10. The method according to claim 9 , wherein the infectious disease is HIV.

Assignments (2)
CHANGE OF ADDRESS Recorded Oct 8, 2025
From: GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED
To: GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED
Reel/Frame 073032/0390 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 4, 2018
From: CHARNLEY, ADAM K.; DONG, XIAOYANG; DODSON, JASON W.; RAMANJULU, JOSHI M.; DARCY, MICHAEL G.; KANG, JIANXING; LEISTER, LARA K.; NEVINS, NEYSA; HUGHES, TERRY V.; MEHLMANN, JOHN F.; ROMANO, JOSEPH J.; LIAN, YIQIAN; LI, YUE; WANG, GREN Z.; YE, GUOSEN; ZHANG, DAOHUA
To: GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED
Reel/Frame 047066/0724 →
Continuity (3)
Provisional Application 62319358 · Apr 7, 2016
Provisional Application 62461301 · Feb 21, 2017
Provisional Application 62461975 · Feb 22, 2017
Cited By (2)
US 12,370,263 US 12,679,849