CA2802743C - Apoptosis signal-regulating kinase inhibitors - Google Patents
Apoptosis signal-regulating kinase inhibitors Download PDFInfo
- Publication number
- CA2802743C CA2802743C CA2802743A CA2802743A CA2802743C CA 2802743 C CA2802743 C CA 2802743C CA 2802743 A CA2802743 A CA 2802743A CA 2802743 A CA2802743 A CA 2802743A CA 2802743 C CA2802743 C CA 2802743C
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- CA
- Canada
- Prior art keywords
- carbon atoms
- triazol
- cyclopropyl
- compound
- imidazol
- Prior art date
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- 230000006907 apoptotic process Effects 0.000 title abstract description 5
- 229940043355 kinase inhibitor Drugs 0.000 title description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 266
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
- 201000010099 disease Diseases 0.000 claims abstract description 26
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 8
- 208000017169 kidney disease Diseases 0.000 claims abstract description 8
- 230000001154 acute effect Effects 0.000 claims abstract description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 6
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 5
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims abstract description 5
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims abstract description 5
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 5
- 208000030090 Acute Disease Diseases 0.000 claims abstract description 4
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims abstract description 4
- 206010069351 acute lung injury Diseases 0.000 claims abstract description 4
- 208000033679 diabetic kidney disease Diseases 0.000 claims abstract description 4
- 230000003176 fibrotic effect Effects 0.000 claims abstract description 4
- 208000019423 liver disease Diseases 0.000 claims abstract description 4
- 208000023504 respiratory system disease Diseases 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 145
- 125000000217 alkyl group Chemical group 0.000 claims description 125
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 100
- 125000001424 substituent group Chemical group 0.000 claims description 87
- 125000001072 heteroaryl group Chemical group 0.000 claims description 79
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000003545 alkoxy group Chemical group 0.000 claims description 61
- 125000005843 halogen group Chemical group 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229940127254 ASK1 inhibitor Drugs 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 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
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
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- LICDVWUXDMKGCX-UHFFFAOYSA-N 4-(4-bromoimidazol-1-yl)-n-[5-(4-cyclopropyl-1,2,4-triazol-3-yl)thiophen-3-yl]pyridine-2-carboxamide Chemical compound C1=NC(Br)=CN1C1=CC=NC(C(=O)NC=2C=C(SC=2)C=2N(C=NN=2)C2CC2)=C1 LICDVWUXDMKGCX-UHFFFAOYSA-N 0.000 claims 1
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- BIGLCQNUCFNKKS-LBPRGKRZSA-N 4-(4-cyclopropylimidazol-1-yl)-5-methyl-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(C=2)N2C=C(N=C2)C2CC2)=CS1 BIGLCQNUCFNKKS-LBPRGKRZSA-N 0.000 claims 1
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- UDHHERAISGACMN-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[2-(4-propan-2-yl-1,2,4-triazol-3-yl)-1,3-thiazol-4-yl]pyridine-2-carboxamide Chemical compound CC(C)N1C=NN=C1C1=NC(NC(=O)C=2N=CC=C(C=2)N2C=C(N=C2)C2CC2)=CS1 UDHHERAISGACMN-UHFFFAOYSA-N 0.000 claims 1
- YOAQKSZRGWUPMP-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[2-[4-(4,4,4-trifluoro-3-hydroxybutan-2-yl)-1,2,4-triazol-3-yl]-1,3-thiazol-4-yl]pyridine-2-carboxamide Chemical compound FC(F)(F)C(O)C(C)N1C=NN=C1C1=NC(NC(=O)C=2N=CC=C(C=2)N2C=C(N=C2)C2CC2)=CS1 YOAQKSZRGWUPMP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
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- 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 1
- UFIISISCBYDUTA-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[5-(4-cyclopropyl-1,2,4-triazol-3-yl)thiophen-3-yl]pyridine-2-carboxamide Chemical compound C=1C(N2C=C(N=C2)C2CC2)=CC=NC=1C(=O)NC(C=1)=CSC=1C1=NN=CN1C1CC1 UFIISISCBYDUTA-UHFFFAOYSA-N 0.000 claims 1
- TWKCRNSVEUJXBT-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[5-[4-(3-hydroxybutan-2-yl)-1,2,4-triazol-3-yl]thiophen-3-yl]pyridine-2-carboxamide Chemical compound CC(O)C(C)N1C=NN=C1C1=CC(NC(=O)C=2N=CC=C(C=2)N2C=C(N=C2)C2CC2)=CS1 TWKCRNSVEUJXBT-UHFFFAOYSA-N 0.000 claims 1
- LCBSIYYZKJGRGR-UHFFFAOYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[5-[4-(4,4,4-trifluoro-3-hydroxybutan-2-yl)-1,2,4-triazol-3-yl]thiophen-3-yl]pyridine-2-carboxamide Chemical compound FC(F)(F)C(O)C(C)N1C=NN=C1C1=CC(NC(=O)C=2N=CC=C(C=2)N2C=C(N=C2)C2CC2)=CS1 LCBSIYYZKJGRGR-UHFFFAOYSA-N 0.000 claims 1
- PZSOQKCNGNNXII-HXUWFJFHSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[5-[4-[(1r)-2,2-dimethylcyclopropyl]-1,2,4-triazol-3-yl]thiophen-3-yl]pyridine-2-carboxamide Chemical compound CC1(C)C[C@H]1N1C(C=2SC=C(NC(=O)C=3N=CC=C(C=3)N3C=C(N=C3)C3CC3)C=2)=NN=C1 PZSOQKCNGNNXII-HXUWFJFHSA-N 0.000 claims 1
- XCINCJNUUXZQDM-KRWDZBQOSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[5-[4-[(1s)-1-phenylethyl]-1,2,4-triazol-3-yl]thiophen-3-yl]pyridine-2-carboxamide Chemical compound C1([C@H](C)N2C(=NN=C2)C=2SC=C(NC(=O)C=3N=CC=C(C=3)N3C=C(N=C3)C3CC3)C=2)=CC=CC=C1 XCINCJNUUXZQDM-KRWDZBQOSA-N 0.000 claims 1
- PZSOQKCNGNNXII-FQEVSTJZSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[5-[4-[(1s)-2,2-dimethylcyclopropyl]-1,2,4-triazol-3-yl]thiophen-3-yl]pyridine-2-carboxamide Chemical compound CC1(C)C[C@@H]1N1C(C=2SC=C(NC(=O)C=3N=CC=C(C=3)N3C=C(N=C3)C3CC3)C=2)=NN=C1 PZSOQKCNGNNXII-FQEVSTJZSA-N 0.000 claims 1
- JEGXWDHWZIXBJF-LBPRGKRZSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[5-[4-[(2s)-1,1,1-trifluoropropan-2-yl]-1,2,4-triazol-3-yl]thiophen-3-yl]pyridine-2-carboxamide Chemical compound FC(F)(F)[C@H](C)N1C=NN=C1C1=CC(NC(=O)C=2N=CC=C(C=2)N2C=C(N=C2)C2CC2)=CS1 JEGXWDHWZIXBJF-LBPRGKRZSA-N 0.000 claims 1
- LJBNZKANULVRKJ-HNNXBMFYSA-N 4-(4-cyclopropylimidazol-1-yl)-n-[5-[4-[(2s)-3-methylbutan-2-yl]-1,2,4-triazol-3-yl]thiophen-3-yl]pyridine-2-carboxamide Chemical compound CC(C)[C@H](C)N1C=NN=C1C1=CC(NC(=O)C=2N=CC=C(C=2)N2C=C(N=C2)C2CC2)=CS1 LJBNZKANULVRKJ-HNNXBMFYSA-N 0.000 claims 1
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- UZLGMNLCLWNZJN-UHFFFAOYSA-N 4-(4-tert-butylimidazol-1-yl)-n-[5-(4-cyclopropyl-1,2,4-triazol-3-yl)thiophen-3-yl]pyridine-2-carboxamide Chemical compound C1=NC(C(C)(C)C)=CN1C1=CC=NC(C(=O)NC=2C=C(SC=2)C=2N(C=NN=2)C2CC2)=C1 UZLGMNLCLWNZJN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
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| EP2598660B1 (en) | 2010-07-26 | 2017-03-15 | Biomatrica, INC. | Compositions for stabilizing dna, rna and proteins in blood and other biological samples during shipping and storage at ambient temperatures |
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| EA027451B1 (ru) | 2011-08-30 | 2017-07-31 | Схди Фаундейшн, Инк. | Ингибиторы кинуренин-3-монооксигеназы, фармацевтические композиции и их применение |
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| EP2934572A4 (en) | 2012-12-20 | 2016-11-23 | Biomatrica Inc | FORMULATIONS AND METHODS FOR STABILIZING PCR REAGENTS |
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| KR101759759B1 (ko) | 2017-07-19 |
| PT2588475E (pt) | 2015-09-08 |
| KR20130129890A (ko) | 2013-11-29 |
| EP2588475A1 (en) | 2013-05-08 |
| US8927582B2 (en) | 2015-01-06 |
| SI2588475T1 (sl) | 2015-12-31 |
| IL223556A (en) | 2016-08-31 |
| EA201291273A1 (ru) | 2013-06-28 |
| IL247405A0 (en) | 2016-11-30 |
| AU2011272782A1 (en) | 2013-01-10 |
| JP5705314B2 (ja) | 2015-04-22 |
| USRE48150E1 (en) | 2020-08-11 |
| BR112012033715A2 (pt) | 2016-11-22 |
| US20130203819A1 (en) | 2013-08-08 |
| AU2011272782B2 (en) | 2014-11-27 |
| US8440665B2 (en) | 2013-05-14 |
| ES2543428T3 (es) | 2015-08-19 |
| PL2588475T3 (pl) | 2015-10-30 |
| US20120004267A1 (en) | 2012-01-05 |
| MX2012015105A (es) | 2013-05-28 |
| JP2013530240A (ja) | 2013-07-25 |
| WO2012003387A1 (en) | 2012-01-05 |
| CN102985418B (zh) | 2015-09-09 |
| CN102985418A (zh) | 2013-03-20 |
| NZ604831A (en) | 2014-12-24 |
| CA2802743A1 (en) | 2012-01-05 |
| EA023040B1 (ru) | 2016-04-29 |
| HK1184781A1 (en) | 2014-01-30 |
| EP2588475B1 (en) | 2015-05-20 |
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