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US 12,577,242 B2Granted
Pyrrolopyridine and imidazopyridine antiviral compounds
AssigneeKatholieke Universiteit Leuven
InventorsEleonora Kiss, Robert Vrancken, Nesya Goris
Life of this patent
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Abstract
The present invention relates to a compound of formula (I) or a stereoisomer, or tautomer, (I) wherein A1, A2, R1 and R2, have the same meaning as that defined in the claims and the description. The present invention also relates to compositions, in particular pharmaceuticals, comprising such compounds, and to uses of such compounds and compositions for the prevention and/or treatment of an infection caused by pestivirus in an animal.
Claims11
A compound of formula (IC) or a stereoisomer, or tautomer thereof,
- wherein,
- R1 is selected from the group consisting of
- wherein the wavy line () indicates the point of attachment to the methylene linker of the main formula (IC);
- t is an integer selected from 0, 1, 2, 3 and 4;
- r is an integer selected from 0, 1, 2, 3 and 4;
- m is an integer selected from 0, 1, 2, 3 and 4;
- W is selected from the group consisting of NR10, S and O;
- Q is selected from the group consisting of CR11 and N;
- Y is selected from the group consisting of N and CR12;
- V is selected from the group consisting of NR13, S and O;
- R2 is selected from the group consisting of biphenylenyl, 1-naphthalenyl, 2-naphthalenyl, 5-tetralinyl, 6-tetralinyl, 1-azulenyl, 2-azulenyl, 3-azulenyl, 4-azulenyl, 5-azulenyl, 6-azulenyl, 7-azulenyl, 8-azulenyl, 4-indenyl, 5-indenyl, 6-indenyl, 7-indenyl, 4-indanyl, 5-indanyl, 5-tetrahydronaphthyl, 6-tetrahydronaphthyl, 7-tetrahydronaphthyl, 8-tetrahydronaphthyl, 1,2,3,4-tetrahydronaphthyl, 1,4-dihydronaphthyl, 1-pyrenyl, 2-pyrenyl, 3-pyrenyl, 4-pyrenyl, 5-pyrenyl pyrazolyl and pyridyl;
- wherein said biphenylenyl, 1-naphthalenyl, 2-naphthalenyl, 5-tetralinyl, 6-tetralinyl, 1-azulenyl, 2-azulenyl, 3-azulenyl, 4-azulenyl, 5-azulenyl, 6-azulenyl, 7-azulenyl, 8-azulenyl, 4-indenyl, 5-indenyl, 6-indenyl, 7-indenyl, 4-indanyl, 5-indanyl, 5-tetrahydronaphthyl, 6-tetrahydronaphthyl, 7-tetrahydronaphthyl, 8-tetrahydronaphthyl, 1,2,3,4-tetrahydronaphthyl, 1,4-dihydronaphthyl, 1-pyrenyl, 2-pyrenyl, 3-pyrenyl, 4-pyrenyl, 5-pyrenyl, pyrazolyl or pyridyl are optionally substituted with one or more Z1;
- each R3 is independently selected from the group consisting of halo, trifluoromethyl, difluoromethyl, C1-6alkoxy, trifluoromethoxy, difluoromethoxy, hydroxyl, C1-6alkyl, —CH2OH, amino, —N(CH3)2, —CH2N(CH3)2, —O(CH2)2OH, —O(CH2)2OCH3, cyano, nitro and —COOH;
- R4 is selected from the group consisting of hydrogen, halo, C1-6alkyl, aryl, trifluoromethyl, difluoromethyl, C1-6alkoxy, trifluoromethoxy, difluoromethoxy, hydroxyl, pyrazolyl, pyridyl and thiophenyl;
- wherein said aryl, pyrazolyl, pyridyl, or thiophenyl are optionally substituted with one or more Z2;
- R5 is selected from the group consisting of hydrogen, halo, C1-6alkyl, aryl, trifluoromethyl, difluoromethyl, C1-6alkoxy, trifluoromethoxy, difluoromethoxy, hydroxyl, pyrazolyl, pyridyl and thiophenyl;
- wherein said aryl, pyrazolyl, pyridyl, or thiophenyl are optionally substituted with one or more Z3;
- R6 is selected from the group consisting of hydrogen, halo, C1-6alkyl, aryl, trifluoromethyl, difluoromethyl, C1-6alkoxy, trifluoromethoxy, difluoromethoxy, hydroxyl, pyrazolyl, pyridyl and thiophenyl;
- wherein said aryl, pyrazolyl, pyridyl, or thiophenyl are optionally substituted with one or more Z4;
- R7 is selected from the group consisting of hydrogen, halo, C1-6alkyl, aryl, trifluoromethyl, difluoromethyl, C1-6alkoxy, trifluoromethoxy, difluoromethoxy, hydroxyl, pyrazolyl, pyridyl and thiophenyl;
- wherein said aryl, pyrazolyl, pyridyl, or thiophenyl are optionally substituted with one or more Z5;
- each R8 is independently selected from the group consisting of halo, trifluoromethyl, difluoromethyl, C1-6alkoxy, trifluoromethoxy, difluoromethoxy, hydroxyl, C1-6alkyl, —CH2OH, amino, —N(CH3)2, —CH2N(CH3)2, —O(CH2)2OH, —O(CH2)2OCH3, cyano, nitro and —COOH;
- each R9 is independently selected from the group consisting of halo, trifluoromethyl, difluoromethyl, C1-6alkoxy, trifluoromethoxy, difluoromethoxy, hydroxyl, C1-6alkyl, —CH2OH, amino, —N(CH3)2, —CH2N(CH3)2, —O(CH2)2OH, —O(CH2)2OCH3, cyano, nitro and —COOH;
- R10 is selected from the group consisting of hydrogen, C1-6alkyl and C3-8cycloalkyl;
- R11 is selected from the group consisting of hydrogen, C1-6alkyl and C3-8cycloalkyl;
- R12 is selected from the group consisting of hydrogen, C1-6alkyl and C3-8cycloalkyl;
- R13 is selected from the group consisting of hydrogen, C1-6alkyl and C3-8cycloalkyl;
- each Z1 is independently selected from the group consisting of halo, trifluoromethyl, difluoromethyl, C1-6alkoxy, trifluoromethoxy, difluoromethoxy, hydroxyl, C1-6alkyl, —CH2OH, amino, —N(CH3)2, —CH2N(CH3)2, —O(CH2)2OH, —O(CH2)2OCH3, cyano, nitro and —COOH;
- each Z2 is independently selected from the group consisting of halo, trifluoromethyl, difluoromethyl, C1-6alkoxy, trifluoromethoxy, difluoromethoxy, hydroxyl, C1-6alkyl, —CH2OH, amino, —N(CH3)2, —CH2N(CH3)2, —O(CH2)2OH, —O(CH2)2OCH3, cyano, nitro and —COOH;
- each Z3 is independently selected from the group consisting of halo, trifluoromethyl, difluoromethyl, C1-6alkoxy, trifluoromethoxy, difluoromethoxy, hydroxyl, C1-6alkyl, —CH2OH, amino, —N(CH3)2, —CH2N(CH3)2, —O(CH2)2OH, —O(CH2)2OCH3, cyano, nitro and —COOH;
- each Z4 is independently selected from the group consisting of halo, trifluoromethyl, difluoromethyl, C1-6alkoxy, trifluoromethoxy, difluoromethoxy, hydroxyl, C1-6alkyl, —CH2OH, amino, —N(CH3)2, —CH2N(CH3)2, —O(CH2)2OH, —O(CH2)2OCH3, cyano, nitro and —COOH;
- each Z5 is independently selected from the group consisting of halo, trifluoromethyl, difluoromethyl, C1-6alkoxy, trifluoromethoxy, difluoromethoxy, hydroxyl, C1-6alkyl, —CH2OH, amino, —N(CH3)2, —CH2N(CH3)2, —O(CH2)2OH, —O(CH2)2OCH3, cyano, nitro and —COOH;
- or a solvate, hydrate, salt or prodrug thereof.
30 more elements
Dependencies are inferred from the claim text.