JP2010511018A - 変性疾患及び炎症性疾患の治療に有用なトリアゾロピリジン化合物 - Google Patents
変性疾患及び炎症性疾患の治療に有用なトリアゾロピリジン化合物 Download PDFInfo
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- JP2010511018A JP2010511018A JP2009538725A JP2009538725A JP2010511018A JP 2010511018 A JP2010511018 A JP 2010511018A JP 2009538725 A JP2009538725 A JP 2009538725A JP 2009538725 A JP2009538725 A JP 2009538725A JP 2010511018 A JP2010511018 A JP 2010511018A
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- substituted
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- alkyl
- unsubstituted
- triazolo
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- 208000015122 neurodegenerative disease Diseases 0.000 title 1
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- 238000000034 method Methods 0.000 claims description 52
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 50
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- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 20
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- 125000005647 linker group Chemical group 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
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- QAMYLEQHGZODSV-UHFFFAOYSA-N n-[4-(4-cyclobutylpiperazin-1-yl)phenyl]-5-(2-methoxypyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine Chemical compound C1=NC(OC)=CC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCN(CC3)C3CCC3)=CC=2)=C1 QAMYLEQHGZODSV-UHFFFAOYSA-N 0.000 claims description 4
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- QLCMKTBNUHIHDZ-UHFFFAOYSA-N 4-[8-[4-(4-methylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-1h-pyridin-2-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=CC=C1C1=CC(=O)NC=C1 QLCMKTBNUHIHDZ-UHFFFAOYSA-N 0.000 claims description 3
- ZUBNWSYSKJLOTG-UHFFFAOYSA-N 4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-8-yl]amino]-N-(pyridin-3-ylmethyl)benzamide Chemical compound C=1C=C(NC=2C3=NC=NN3C(C3=CNN=C3)=CC=2)C=CC=1C(=O)NCC1=CC=CN=C1 ZUBNWSYSKJLOTG-UHFFFAOYSA-N 0.000 claims description 3
- ZJJHANDRHMZFNS-UHFFFAOYSA-N 5-(2-methoxypyridin-4-yl)-n-[4-(4-pentan-3-ylpiperazin-1-yl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-8-amine Chemical compound C1CN(C(CC)CC)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=CC=C1C1=CC=NC(OC)=C1 ZJJHANDRHMZFNS-UHFFFAOYSA-N 0.000 claims description 3
- PBQXQILSTDCPSF-UHFFFAOYSA-N 5-(2-methoxypyridin-4-yl)-n-[4-[4-(3-methylbutyl)piperazin-1-yl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-8-amine Chemical compound C1=NC(OC)=CC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCN(CCC(C)C)CC3)=CC=2)=C1 PBQXQILSTDCPSF-UHFFFAOYSA-N 0.000 claims description 3
- GUOGNCXMTYLKPA-UHFFFAOYSA-N N-[4-(4-methylpiperazin-1-yl)phenyl]-5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=CC=C1C1=CNN=C1 GUOGNCXMTYLKPA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- BRUHOUSYWYPUFF-UHFFFAOYSA-N n-[4-(4-cyclopropylpiperazin-1-yl)phenyl]-5-(2-methoxypyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine Chemical compound C1=NC(OC)=CC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCN(CC3)C3CC3)=CC=2)=C1 BRUHOUSYWYPUFF-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- KCNZIACBWMIJNK-UHFFFAOYSA-N 4-[8-(4-piperazin-1-ylanilino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-1h-pyridin-2-one Chemical compound C1=CNC(=O)C=C1C(N1N=CN=C11)=CC=C1NC1=CC=C(N2CCNCC2)C=C1 KCNZIACBWMIJNK-UHFFFAOYSA-N 0.000 claims description 2
- JOPGBGHNPPXTLE-IYBDPMFKSA-N 4-[8-[3-fluoro-4-[(3r,5s)-3,4,5-trimethylpiperazin-1-yl]anilino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-1h-pyridin-2-one Chemical compound C1[C@@H](C)N(C)[C@@H](C)CN1C(C(=C1)F)=CC=C1NC(C1=NC=NN11)=CC=C1C1=CC(=O)NC=C1 JOPGBGHNPPXTLE-IYBDPMFKSA-N 0.000 claims description 2
- JBOQOAZRZAOGCB-UHFFFAOYSA-N 4-[8-[4-(4-cyclohexylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-1h-pyridin-2-one Chemical compound C1=CNC(=O)C=C1C(N1N=CN=C11)=CC=C1NC1=CC=C(N2CCN(CC2)C2CCCCC2)C=C1 JBOQOAZRZAOGCB-UHFFFAOYSA-N 0.000 claims description 2
- IPTVVCCQBVOALQ-UHFFFAOYSA-N 4-[8-[4-(4-cyclopropylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-1h-pyridin-2-one Chemical compound C1=CNC(=O)C=C1C(N1N=CN=C11)=CC=C1NC1=CC=C(N2CCN(CC2)C2CC2)C=C1 IPTVVCCQBVOALQ-UHFFFAOYSA-N 0.000 claims description 2
- GGEYEWJEDISIBV-UHFFFAOYSA-N 4-[8-[4-(4-ethylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-1h-pyridin-2-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=CC=C1C1=CC(=O)NC=C1 GGEYEWJEDISIBV-UHFFFAOYSA-N 0.000 claims description 2
- ZEPIAQCSIJKAPH-UHFFFAOYSA-N 4-[8-[4-(4-pentan-3-ylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-1h-pyridin-2-one Chemical compound C1CN(C(CC)CC)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=CC=C1C1=CC(=O)NC=C1 ZEPIAQCSIJKAPH-UHFFFAOYSA-N 0.000 claims description 2
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- AOVBUOHANYJDCK-UHFFFAOYSA-N 5-(1h-indol-6-yl)-n-[4-(4-propan-2-ylpiperazin-1-yl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-8-amine Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=CC=C1C1=CC=C(C=CN2)C2=C1 AOVBUOHANYJDCK-UHFFFAOYSA-N 0.000 claims description 2
- FMERASVOLQZDQY-UHFFFAOYSA-N 5-(2,4-dimethoxypyrimidin-5-yl)-n-(4-morpholin-4-ylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine Chemical compound COC1=NC(OC)=NC=C1C(N1N=CN=C11)=CC=C1NC1=CC=C(N2CCOCC2)C=C1 FMERASVOLQZDQY-UHFFFAOYSA-N 0.000 claims description 2
- YHTYWOXRCPKSDZ-UHFFFAOYSA-N 5-(2,4-dimethoxypyrimidin-5-yl)-n-[4-(4-propan-2-ylpiperazin-1-yl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-8-amine Chemical compound COC1=NC(OC)=NC=C1C(N1N=CN=C11)=CC=C1NC1=CC=C(N2CCN(CC2)C(C)C)C=C1 YHTYWOXRCPKSDZ-UHFFFAOYSA-N 0.000 claims description 2
- RPVDBKFNIFENSR-UHFFFAOYSA-N 5-(2-methoxypyridin-4-yl)-n-[4-(4-propylpiperazin-1-yl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-8-amine Chemical compound C1CN(CCC)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=CC=C1C1=CC=NC(OC)=C1 RPVDBKFNIFENSR-UHFFFAOYSA-N 0.000 claims description 2
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- WNBKJMUBFMIEQZ-UHFFFAOYSA-N N-[4-(4-pentan-3-ylpiperazin-1-yl)phenyl]-5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine Chemical compound C1CN(C(CC)CC)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=CC=C1C1=CNN=C1 WNBKJMUBFMIEQZ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
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- DUHODPSCPLLDHA-UHFFFAOYSA-N n-[4-(4-ethylpiperazin-1-yl)phenyl]-5-(2-methoxypyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=CC=C1C1=CC=NC(OC)=C1 DUHODPSCPLLDHA-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Landscapes
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86814406P | 2006-12-01 | 2006-12-01 | |
| PCT/EP2007/063106 WO2008065198A1 (en) | 2006-12-01 | 2007-11-30 | Triazolopyridine compounds useful for the treatment of degenerative & inflammatory diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010511018A true JP2010511018A (ja) | 2010-04-08 |
| JP2010511018A5 JP2010511018A5 (enExample) | 2010-11-25 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009538725A Pending JP2010511018A (ja) | 2006-12-01 | 2007-11-30 | 変性疾患及び炎症性疾患の治療に有用なトリアゾロピリジン化合物 |
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| Country | Link |
|---|---|
| US (1) | US7977352B2 (enExample) |
| EP (1) | EP2086540B8 (enExample) |
| JP (1) | JP2010511018A (enExample) |
| AT (1) | ATE495743T1 (enExample) |
| DE (1) | DE602007012133D1 (enExample) |
| WO (1) | WO2008065198A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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- 2007-11-30 DE DE602007012133T patent/DE602007012133D1/de active Active
- 2007-11-30 WO PCT/EP2007/063106 patent/WO2008065198A1/en not_active Ceased
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011529032A (ja) * | 2008-07-25 | 2011-12-01 | ガラパゴス・ナムローゼ・フェンノートシャップ | 変性及び炎症性疾患の治療に有用な新規化合物 |
| JP2019531289A (ja) * | 2016-09-16 | 2019-10-31 | ヘルムホルツ ツェントゥルム ミュンヘン ドイチェス フォルシュングスツェントゥルム フューア ゲズントハイト ウント ウムヴェルト (ゲーエムベーハー) | Traf6阻害剤 |
| JP7117293B2 (ja) | 2016-09-16 | 2022-08-12 | ヘルムホルツ ツェントゥルム ミュンヘン ドイチェス フォルシュングスツェントゥルム フューア ゲズントハイト ウント ウムヴェルト (ゲーエムベーハー) | Traf6阻害剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| US7977352B2 (en) | 2011-07-12 |
| DE602007012133D1 (de) | 2011-03-03 |
| US20090105242A1 (en) | 2009-04-23 |
| EP2086540B1 (en) | 2011-01-19 |
| WO2008065198A1 (en) | 2008-06-05 |
| ATE495743T1 (de) | 2011-02-15 |
| EP2086540B8 (en) | 2011-03-02 |
| EP2086540A1 (en) | 2009-08-12 |
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