JP2013530240A5 - - Google Patents
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- Publication number
- JP2013530240A5 JP2013530240A5 JP2013518740A JP2013518740A JP2013530240A5 JP 2013530240 A5 JP2013530240 A5 JP 2013530240A5 JP 2013518740 A JP2013518740 A JP 2013518740A JP 2013518740 A JP2013518740 A JP 2013518740A JP 2013530240 A5 JP2013530240 A5 JP 2013530240A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopropyl
- carbon atoms
- triazol
- optionally substituted
- pharmaceutically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 56
- -1 4-cyclopropyl-1H-imidazol-1-yl Chemical group 0.000 claims description 50
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000005843 halogen group Chemical group 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- BXWKCDYKCYLKLD-NSHDSACASA-N 4-(4-cyclopropylimidazol-1-yl)-n-[2-[4-[(2s)-1,1,1-trifluoropropan-2-yl]-1,2,4-triazol-3-yl]-1,3-thiazol-4-yl]pyridine-2-carboxamide Chemical compound FC(F)(F)[C@H](C)N1C=NN=C1C1=NC(NC(=O)C=2N=CC=C(C=2)N2C=C(N=C2)C2CC2)=CS1 BXWKCDYKCYLKLD-NSHDSACASA-N 0.000 claims description 2
- NHCMYVVORIJKBE-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[5-(4-cyclopropyl-1,2,4-triazol-3-yl)thiophen-3-yl]-5-methylpyridine-2-carboxamide Chemical compound CC1=CN=C(C(=O)NC=2C=C(SC=2)C=2N(C=NN=2)C2CC2)C=C1N(C=1)C=NC=1C1CC1 NHCMYVVORIJKBE-UHFFFAOYSA-N 0.000 claims description 2
- RQIGKHWWWTYKQA-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[2-(4-cyclopropyl-1,2,4-triazol-3-yl)-1,3-thiazol-4-yl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(N=1)=CSC=1C1=NN=CN1C1CC1 RQIGKHWWWTYKQA-UHFFFAOYSA-N 0.000 claims description 2
- VKWGKBVWKPPWRG-UHFFFAOYSA-N 4-(6-cyclopropylpyridin-3-yl)-n-[5-(4-cyclopropyl-1,2,4-triazol-3-yl)thiophen-3-yl]pyridine-2-carboxamide Chemical compound C=1C(C=2C=NC(=CC=2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CSC=1C1=NN=CN1C1CC1 VKWGKBVWKPPWRG-UHFFFAOYSA-N 0.000 claims description 2
- VPCXPQKTNBQUSD-UHFFFAOYSA-N 5-(4-cyclopropylimidazol-1-yl)-n-[2-(4-cyclopropyl-1,2,4-triazol-3-yl)-1,3-thiazol-4-yl]-2-methoxybenzamide Chemical compound COC1=CC=C(N2C=C(N=C2)C2CC2)C=C1C(=O)NC(N=1)=CSC=1C1=NN=CN1C1CC1 VPCXPQKTNBQUSD-UHFFFAOYSA-N 0.000 claims description 2
- VLQPKPCJTAVPON-UHFFFAOYSA-N 5-(4-cyclopropylimidazol-1-yl)-n-[5-(4-cyclopropyl-1,2,4-triazol-3-yl)thiophen-3-yl]-2-methoxybenzamide Chemical compound COC1=CC=C(N2C=C(N=C2)C2CC2)C=C1C(=O)NC(C=1)=CSC=1C1=NN=CN1C1CC1 VLQPKPCJTAVPON-UHFFFAOYSA-N 0.000 claims description 2
- XQLUBDAVNKCKQD-UHFFFAOYSA-N 5-(6-cyclopropylpyridin-3-yl)-n-[5-(4-cyclopropyl-1,2,4-triazol-3-yl)thiophen-3-yl]-2,4-dimethoxybenzamide Chemical compound COC1=CC(OC)=C(C=2C=NC(=CC=2)C2CC2)C=C1C(=O)NC(C=1)=CSC=1C1=NN=CN1C1CC1 XQLUBDAVNKCKQD-UHFFFAOYSA-N 0.000 claims description 2
- OXBWEFYXJCXFOR-UHFFFAOYSA-N 5-(6-cyclopropylpyridin-3-yl)-n-[5-(4-cyclopropyl-1,2,4-triazol-3-yl)thiophen-3-yl]-2-methoxybenzamide Chemical compound COC1=CC=C(C=2C=NC(=CC=2)C2CC2)C=C1C(=O)NC(C=1)=CSC=1C1=NN=CN1C1CC1 OXBWEFYXJCXFOR-UHFFFAOYSA-N 0.000 claims description 2
- 208000030090 Acute Disease Diseases 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 2
- 208000004852 Lung Injury Diseases 0.000 claims description 2
- 206010069363 Traumatic lung injury Diseases 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 2
- 230000003176 fibrotic effect Effects 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 2
- 208000017169 kidney disease Diseases 0.000 claims description 2
- 208000019423 liver disease Diseases 0.000 claims description 2
- 231100000515 lung injury Toxicity 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- LKFHDVNDOWOQLU-UHFFFAOYSA-N n-[2-(4-cyclopropyl-1,2,4-triazol-3-yl)-1,3-thiazol-4-yl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound C=1C(C=2C=NC=CC=2)=CC=NC=1C(=O)NC(N=1)=CSC=1C1=NN=CN1C1CC1 LKFHDVNDOWOQLU-UHFFFAOYSA-N 0.000 claims description 2
- HDDBDWDCDKNSCS-UHFFFAOYSA-N n-[4-(4-cyclopropyl-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound C=1C(C=2C=NC=CC=2)=CC=NC=1C(=O)NC(SC=1)=NC=1C1=NN=CN1C1CC1 HDDBDWDCDKNSCS-UHFFFAOYSA-N 0.000 claims description 2
- SQTMEYNQSUNPLG-UHFFFAOYSA-N n-[5-(4-cyclopropyl-1,2,4-triazol-3-yl)thiophen-3-yl]-4-pyridin-3-ylpyridine-2-carboxamide Chemical compound C=1C(C=2C=NC=CC=2)=CC=NC=1C(=O)NC(C=1)=CSC=1C1=NN=CN1C1CC1 SQTMEYNQSUNPLG-UHFFFAOYSA-N 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 208000023504 respiratory system disease Diseases 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- SAFMUWNMQDZETL-UHFFFAOYSA-N 4-cyclopropyl-3-thiophen-2-yl-1,2,4-triazole Chemical compound C1CC1N1C(C=2SC=CC=2)=NN=C1 SAFMUWNMQDZETL-UHFFFAOYSA-N 0.000 claims 1
- 101001018196 Homo sapiens Mitogen-activated protein kinase kinase kinase 5 Proteins 0.000 claims 1
- 102100033127 Mitogen-activated protein kinase kinase kinase 5 Human genes 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 3
- BOQNUOWAVFCKKS-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[2-(4-cyclopropyl-1,2,4-triazol-3-yl)-1,3-thiazol-4-yl]-5-methylpyridine-2-carboxamide Chemical compound CC1=CN=C(C(=O)NC=2N=C(SC=2)C=2N(C=NN=2)C2CC2)C=C1N(C=1)C=NC=1C1CC1 BOQNUOWAVFCKKS-UHFFFAOYSA-N 0.000 description 1
- IMLYDRHZHDRSMD-UHFFFAOYSA-N 5-(4-cyclopropylimidazol-1-yl)-n-[2-(4-cyclopropyl-1,2,4-triazol-3-yl)-1,3-thiazol-4-yl]-2-fluorobenzamide Chemical compound FC1=CC=C(N2C=C(N=C2)C2CC2)C=C1C(=O)NC(N=1)=CSC=1C1=NN=CN1C1CC1 IMLYDRHZHDRSMD-UHFFFAOYSA-N 0.000 description 1
- BKXLKDCLRVCQTO-UHFFFAOYSA-N 5-(4-cyclopropylimidazol-1-yl)-n-[5-(4-cyclopropyl-1,2,4-triazol-3-yl)thiophen-3-yl]-2-fluorobenzamide Chemical compound FC1=CC=C(N2C=C(N=C2)C2CC2)C=C1C(=O)NC(C=1)=CSC=1C1=NN=CN1C1CC1 BKXLKDCLRVCQTO-UHFFFAOYSA-N 0.000 description 1
- 229940127254 ASK1 inhibitor Drugs 0.000 description 1
- JQEROOCRTFCUNY-UHFFFAOYSA-N n-[4-(4-cyclopropyl-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]-4-(6-methoxypyridin-3-yl)pyridine-2-carboxamide Chemical compound C1=NC(OC)=CC=C1C1=CC=NC(C(=O)NC=2SC=C(N=2)C=2N(C=NN=2)C2CC2)=C1 JQEROOCRTFCUNY-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36108010P | 2010-07-02 | 2010-07-02 | |
| US61/361,080 | 2010-07-02 | ||
| PCT/US2011/042694 WO2012003387A1 (en) | 2010-07-02 | 2011-06-30 | Apoptosis signal-regulating kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013530240A JP2013530240A (ja) | 2013-07-25 |
| JP2013530240A5 true JP2013530240A5 (enExample) | 2014-06-19 |
| JP5705314B2 JP5705314B2 (ja) | 2015-04-22 |
Family
ID=44318106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013518740A Active JP5705314B2 (ja) | 2010-07-02 | 2011-06-30 | アポトーシスシグナル調節キナーゼ阻害剤 |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US8440665B2 (enExample) |
| EP (1) | EP2588475B1 (enExample) |
| JP (1) | JP5705314B2 (enExample) |
| KR (1) | KR101759759B1 (enExample) |
| CN (1) | CN102985418B (enExample) |
| AU (1) | AU2011272782B2 (enExample) |
| BR (1) | BR112012033715A2 (enExample) |
| CA (1) | CA2802743C (enExample) |
| EA (1) | EA023040B1 (enExample) |
| ES (1) | ES2543428T3 (enExample) |
| IL (2) | IL223556A (enExample) |
| MX (1) | MX2012015105A (enExample) |
| NZ (1) | NZ604831A (enExample) |
| PL (1) | PL2588475T3 (enExample) |
| PT (1) | PT2588475E (enExample) |
| SI (1) | SI2588475T1 (enExample) |
| WO (1) | WO2012003387A1 (enExample) |
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| AU2009279787B2 (en) | 2008-08-04 | 2014-05-29 | Chdi Foundation, Inc. | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
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| EP2528441A4 (en) | 2010-01-25 | 2013-07-10 | Chdi Foundation Inc | CYNURENINE-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND METHOD OF USE THEREOF |
| MX2012015105A (es) * | 2010-07-02 | 2013-05-28 | Gilead Sciences Inc | Inhibidores de cinasa de regulacion mediante señal de apoptosis. |
| EP2598661B1 (en) | 2010-07-26 | 2017-09-27 | Biomatrica, INC. | Compositions for stabilizing dna, rna and proteins in saliva and other biological samples during shipping and storage at ambient temperatures |
| WO2012018638A2 (en) | 2010-07-26 | 2012-02-09 | Biomatrica, Inc. | Compositions for stabilizing dna, rna and proteins in blood and other biological samples during shipping and storage at ambient temperatures |
| JP5927201B2 (ja) | 2010-12-16 | 2016-06-01 | カルチャン リミテッド | Ａｓｋ１阻害ピロロピリミジン誘導体 |
| JP2014525443A (ja) | 2011-08-30 | 2014-09-29 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | キヌレニン−３−モノオキシゲナーゼインヒビター、医薬組成物、およびこれらの使用方法 |
| US9981918B2 (en) | 2011-08-30 | 2018-05-29 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| UY34573A (es) | 2012-01-27 | 2013-06-28 | Gilead Sciences Inc | Inhibidor de la quinasa que regula la señal de la apoptosis |
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| JP6661554B2 (ja) | 2014-06-10 | 2020-03-11 | バイオマトリカ，インク． | 周囲温度における血小板の安定化 |
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