PT2588475E - Inibidores de cinase reguladora dos sinais da apoptose - Google Patents

Info

Publication number

PT2588475E

PT2588475E PT117342204T PT11734220T PT2588475E PT 2588475 E PT2588475 E PT 2588475E PT 117342204 T PT117342204 T PT 117342204T PT 11734220 T PT11734220 T PT 11734220T PT 2588475 E PT2588475 E PT 2588475E

Authority

PT

Portugal

Prior art keywords

cyclopropyl

triazol

alkyl

carbon atoms

compound

Prior art date

2010-07-02

Links

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• 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 description 236
• -1 5- (4-cyclopropyl-4H-1,2,4-triazol-3-yl) thiophen-3-yl Chemical group 0.000 claims description 178
• 125000000217 alkyl group Chemical group 0.000 claims description 99
• 125000004432 carbon atom Chemical group C* 0.000 claims description 79
• 125000001424 substituent group Chemical group 0.000 claims description 74
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 69
• 125000001072 heteroaryl group Chemical group 0.000 claims description 56
• 125000003118 aryl group Chemical group 0.000 claims description 50
• 125000003545 alkoxy group Chemical group 0.000 claims description 45
• 238000000034 method Methods 0.000 claims description 44
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
• 125000000623 heterocyclic group Chemical group 0.000 claims description 38
• 125000005843 halogen group Chemical group 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 239000001257 hydrogen Substances 0.000 claims description 36
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 26
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
• 201000010099 disease Diseases 0.000 claims description 20
• 125000004429 atom Chemical group 0.000 claims description 19
• 238000011282 treatment Methods 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 15
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 13
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000004043 oxo group Chemical group O=* 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 9
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• 206010012601 diabetes mellitus Diseases 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 7
• 230000001154 acute effect Effects 0.000 claims description 6
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• 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 4
• 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 4
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• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• 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 3
• 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 3
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• 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 3
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• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
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• 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 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
• 125000001475 halogen functional group Chemical group 0.000 claims 1
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