Heterocyclic modulators of lipid synthesis
US-2024400552-A1 · Dec 5, 2024 · US
Kinase inhibitors
US9458154B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9458154-B2 |
| Application number | US-201114363556-A |
| Country | US |
| Kind code | B2 |
| Filing date | Dec 9, 2011 |
| Priority date | Dec 9, 2011 |
| Publication date | Oct 4, 2016 |
| Grant date | Oct 4, 2016 |
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Abstract
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Disclosed are compounds having [1,2,4]triazolo[4,3-a]pyridine groups and pharmaceutically acceptable salts thereof. The compounds are p38 MAPK inhibitors, useful as anti-inflammatory agents in the treatment of, inter alia, diseases of the respiratory tract.
First claim
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The invention claimed is: 1. A compound selected from the group consisting of: 1-(5-tert-Butyl-2-phenyl-2H-pyrazol-3-yl)-3-[4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-Cyclopropyl-3-[4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[3-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-ylsulfanyl)-indan-1-yl]-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[4-{3-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy}-1,2,3,4-tetrahydro-naphthalen-1-yl)-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-7-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-{5-tert-Butyl-2-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-2H-pyrazol-3-yl}-3-[4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(5-tert-Butyl-isoxazol-3-yl)-3-[3-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-indan-1-yl]-urea; 1-{5-tert-Butyl-2-[3-(2-dimethylamino-ethoxy)-phenyl]-2H-pyrazol-3-yl}-3-[4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-[5-tert-Butyl-2-(4-hydroxy-phenyl)-2H-pyrazol-3-yl]-3-[4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[4-(3-cyclopentyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-[5-tert-Butyl-2-(3-morpholin-4-ylmethyl-phenyl)-2H-pyrazol-3-yl]-3-[4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[4-(3-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[4-(3-pyridin-2-yl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea; 1-[5-tert-Butyl-2-(3-chloro-4-hydroxy-phenyl)-2H-pyrazol-3-yl]-3-[4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[4-(3-cyclohexyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-[5-tert-Butyl-2-(4-chloro-3-hydroxy-phenyl)-2H-pyrazol-3-yl]-3-[4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(3-Fluoro-5-morpholin-4-yl-phenyl)-3-[4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-{5-tert-Butyl-2-(4-fluoro-3-morpholin-4-ylmethyl-phenyl)-2H-pyrazol-3-yl}-3-[4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-[5-tert-Butyl-2-(3-chloro-4-hydroxy-phenyl)-2H-pyrazol-3-yl]-3-(4-{3-[2-(2-hydroxy-ethylsulfanyl)-phenyl]-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy}-1,2,3,4-tetrahydro-naphthalen-1-yl)-urea; 1-[5-tert-Butyl-2-(3-chloro-4-hydroxy-phenyl)-2H-pyrazol-3-yl]-3-(4-{3-[2-(2-hydroxy-ethylsulfanyl)-phenyl]-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy}-1,2,3,4-tetrahydro-naphthalen-1-yl)-urea; and 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-{4-[3-(2-pyrrolidin-1-yl-pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea, or a pharmaceutically acceptable salt of said compound. 2. A compound, which is selected from the group consisting of: 1-Cyclopropyl-3-[(1S,4S)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; (±)-trans-1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[3-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-ylsulfanyl)-indan-1-yl]-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[(1S,4R)-4-{3-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy}-1,2,3,4-tetrahydro-naphthalen-1-yl)-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[(1S,4R)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-7-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-{5-tert-Butyl-2-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-2H-pyrazol-3-yl}-3-[(1S,4R)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-{(1S,4R)-4-(3-(2-hydroxy-phenyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea; 1-(5-tert-Butyl-isoxazol-3-yl)-3-[(1S,3S)-3-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-indan-1-yl]-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-{(1S,4R)-4-[3-(2-hydroxy-ethylsulfanyl)-phenyl]-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl-urea; 1-{5-tert-Butyl-2-[3-(2-dimethylamino-ethoxy)-phenyl]-2H-pyrazol-3-yl}-3-[(1S,4R)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-[5-tert-Butyl-2-(3-chloro-4-hydroxy-phenyl)-2H-pyrazol-3-yl]-3-[(1S,4R)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-Cyclopropyl-3-[(1S,4R)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(5-tert-Butyl-2-(4-chloro-3-hydroxyphenyl)-2H-pyrazol-3-yl)-3-[(1S,4R)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydronaphthalen-1-yl]-urea; 1-[5-tert-Butyl-2-(4-hydroxy-phenyl)-2H-pyrazol-3-yl]-3-[(1S,4R)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(5-tert-Butyl-isoxazol-3-yl)-3-[(1S,4R)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[(1S,4R)-4-(3-cyclopentyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-[5-tert-Butyl-2-(3-morpholin-4-ylmethyl-phenyl)-2H-pyrazol-3-yl]-3-[(1S,4R)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl-3-{(1S,4R)-4-(3-(2,6-dichloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl-3-yl)-3-[(1S,4R)-4-(3-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl-3-yl)-3-[(1S,4R)-4-(3-pyridin-2-yl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl-3-{(1S,4R)-4-(3-(2-chloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea; 1-{(1S,4R)-4-[3-(2-Benzyloxy-phenyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl}-3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-urea; 1-[5-tert-Butyl-2-(3-chloro-4-hydroxy-phenyl)-2H-pyrazol-3-yl]-3-[(1S,4S)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[(1S,4R)-4-(3-cyclohexyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-[5-tert-Butyl-2-(4-chloro-3-hydroxy-phenyl)-2H-pyrazol-3-yl]-3-[(1S,4S)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(3-Fluoro-5-morpholin-4-yl-phenyl)-3-[(1S,4R)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-(3-Fluoro-5-morpholin-4-yl-phenyl)-3-[(1S,4S)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-{5-tert-Butyl-2-(4-fluoro-3-morpholin-4-ylmethyl-phenyl)-2H-pyrazol-3-yl}-3-[(1S,4R)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea; 1-[5-tert-Butyl-2-(3-chloro-4-hydroxy-phenyl)-2H-pyrazol-3-yl]-3-((1S,4R)-4-{3-[2-(2-hydroxy-ethylsulfanyl)-phenyl]-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy}-1,2,3,4-tetrahydro-naphthalen-1-yl)-urea; 1-[5-tert-Butyl-2-(3-chloro-4-hyd
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Antiasthmatics · CPC title
linked by a chain containing hetero atoms as chain links · CPC title
- C07D471/04Primary
Ortho-condensed systems · CPC title
linked by a chain containing hetero atoms as chain links · CPC title
Pulmonary tract; Aromatherapy · CPC title
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- What does patent US9458154B2 cover?
- Disclosed are compounds having [1,2,4]triazolo[4,3-a]pyridine groups and pharmaceutically acceptable salts thereof. The compounds are p38 MAPK inhibitors, useful as anti-inflammatory agents in the treatment of, inter alia, diseases of the respiratory tract.
- Who is the assignee on this patent?
- Finch Harry, Van Niel Monique Bodil, Woo Chi-Kit, and 1 more
- What technology area does this patent fall under?
- Primary CPC classification C07D471/04. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue Oct 04 2016 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).