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US 9,868,740 B2Granted
Pyrimidinone compounds which are HNE inhibitors
AssigneeChiesi Farmaceutici S.p.A.
InventorsLilian Alcaraz, Robert Andrew Heald, Jonathan Mark Sutton, Elisabetta Armani, Carmelida Capaldi
Life of this patent
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Abstract
This invention relates to heterocyclic compounds, which are pyrimidinone derivatives having human neutrophil elastase inhibitory properties, and their use in therapy.
Claims13
A compound selected from the group consisting of:
- 1-(2-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3a]pyrimidin-5-yl]-phenyl}-ethyl)-4-methoxy-pyridinium bromide;
- 1-(2-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-ethyl)-3-hydroxy-pyridinium bromide;
- 1-(2-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-ethyl)-2-methyl-pyridinium bromide;
- 1-(2-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-ethyl)-4-hydroxymethyl-pyridinium bromide;
- 1-(2-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-ethyl)-4-isopropyl-pyridinium bromide;
- 1-(2-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-ethyl)-5-hydroxy-2-methyl-pyridinium bromide;
- 1-(2-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-ethyl)-2,4-dimethyl-pyridinium bromide;
- 1-(2-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-ethyl)-3,5-dimethyl-pyridinium bromide;
- 1-(2-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-ethyl)-2-ethyl-pyridinium bromide;
- 1-(2-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-ethyl)-2-(2-hydroxy-ethyl)-pyridinium bromide;
- and
- 1-(2-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-ethyl)-4-ethyl-pyridinium bromide;
- or a pharmaceutically acceptable salt of said compound.
10 more elements
A compound of formula (I)″ or a pharmaceutically acceptable salt thereof:
- wherein the group R is selected from the group consisting of
- 4-methoxy-pyridinyl;
- 3-hydroxy-pyridinyl;
- 2-methyl-pyridinyl;
- 4-hydroxymethyl-pyridinyl;
- 4-isopropyl-pyridinyl;
- 5-hydroxy-2-methyl-pyridinyl;
- 2,4-dimethyl-pyridinyl;
- 3,5-dimethyl-pyridinyl;
- 2-ethyl-pyridinyl;
- 2-(2-hydroxy-ethyl)-pyridinyl;
- and
- 4-ethyl-pyridinyl.
10 more elements
Dependencies are inferred from the claim text.