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US 12,134,609 B2Granted
Quinoline cGAS antagonist compounds
AssigneesImmuneSensor Therapeutics, Inc., Board of Regents, The University of Texas System
InventorsJian Qiu, Qi Wei, Matt Tschantz, Heping Shi, Youtong Wu, Huiling Tan, Lijun Sun, Chuo Chen, Zhijian Chen
Life of this patent
Estimating the term…
Abstract
The present disclosure provides compounds that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.
Claims23
A compound, wherein the compound is of formula I*:
- or a pharmaceutically acceptable salt thereof, wherein:
- R1 is an optionally substituted imidazole, pyrazole, pyrrole, furan, or pyridine;
- R2 is —NRR5,
- each R3 is independently halogen, —OMe, —OEt, —NR2, or —SR;
- Ring B1 is substituted phenyl;
- Ring B2 is a 4- to 7-membered saturated or partially unsaturated carbocyclic or heterocyclic ring having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, and sulfur;
- or a 5- to 6-membered heteroaryl ring having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, and sulfur;
- each R is independently hydrogen or an optionally substituted group selected from C1-6 aliphatic;
- benzyl;
- phenyl;
- a 4- to 7-membered saturated or partially unsaturated carbocyclic or heterocyclic ring having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, and sulfur;
- and a 5- to 6-membered heteroaryl ring having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, and sulfur;
- R5 is —(CH2)2-4OH, —(CH2)2-4O(CH2)1-5CO2H, —(CH2)2-4O(CH2)1-5CO2C1-4alkyl, —(CH2)0-3CH(CH2OH)2, —(CH2)2-4OC1-4alkyl, —(CR2)0-5CO2R, —(CR2)0-5CONR2, —(CR2)0-4C(O)NR(CR2)0-4CO2R, —(CR2)0-4C(O)NR(CR2)0-4CONR2, —(CR2)0-4NRC(O)R, —(CR2)0-4SO3R, —(CR2)0-4SO2NR2, —(CR2)0-4 OSO2NR2, —(CR2)0-4NRSO2R, —(CR2)0-4NRSO2OR, —(CR2)0-4OP(OR)2, —(CR2)0-4OP(O)(OR)2, —(CR2)0-4P(O)(OR)2, —(CR2)0-4OP(O)(H)OR;
- each R6 is independently halogen, —CN, —COR, —(CR2)0-4CO2R, —(CR2)0-4CONR2, —OR, —(CR2)1-4OR, —NR2, —(CR2) 1-4NR2, —NRC(O)OR, —NRC(O)R, —NRC(O)NR2, —SR, —SO2R, —S(O)R, —(CR2)0-4SO3R, —(CR2)0-4SO2NR2, —(CR2)0-4OSO2NR2, —(CR2)0-4NRSO2R, —(CR2)0-4NRSO2OR, —(CR2)0-4OP(OR)2, —(CR2)0-4OP(O)(OR)2, —(CR2)0-4P(O)(OR)2, —(CR2)0-4OP(O)(H)OR, —B(OR)2, or RB,
- RB and RC, independently, are an optionally substituted group selected from C1-6 aliphatic;
- phenyl;
- a 4- to 10-membered saturated or partially unsaturated monocyclic or bicyclic carbocyclic or heterocyclic ring having 1 to 3 heteroatoms independently selected from nitrogen, oxygen, and sulfur;
- and a 5- to 6-membered heteroaryl ring having 1 to 4 heteroatoms independently selected from nitrogen, oxygen, and sulfur;
- each Ra is independently H or C1-6alkyl;
- each m is 1, 2, 3, or 4;
- n is 1, 2, 3, or 4;
- q is 0, 1, or 2.
19 more elements
A compound, wherein the compound is selected from:
- or is a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.