IL223556A - Kinase inhibitors regulating apoptosis signal - Google Patents

Info

Publication number

IL223556A

IL223556A IL223556A IL22355612A IL223556A IL 223556 A IL223556 A IL 223556A IL 223556 A IL223556 A IL 223556A IL 22355612 A IL22355612 A IL 22355612A IL 223556 A IL223556 A IL 223556A

Authority

IL

Israel

Prior art keywords

formula

cyclopropyl

alkyl

acid

triazol

Prior art date

2010-07-02

Links

• Espacenet
• Global Dossier
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• 230000006907 apoptotic process Effects 0.000 title description 4
• 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 220
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 27
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 24
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 8
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 2
• 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
• 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
• 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 1
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 92
• -1 heteroaryl amide Chemical class 0.000 description 89
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• 125000001072 heteroaryl group Chemical group 0.000 description 58
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• 125000003118 aryl group Chemical group 0.000 description 54
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
• 125000000753 cycloalkyl group Chemical group 0.000 description 46
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• 125000004432 carbon atom Chemical group C* 0.000 description 44
• 238000000034 method Methods 0.000 description 44
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
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• 125000003545 alkoxy group Chemical group 0.000 description 36
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
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• 125000000623 heterocyclic group Chemical group 0.000 description 31
• 230000002829 reductive effect Effects 0.000 description 31
• 238000005481 NMR spectroscopy Methods 0.000 description 30
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• 229910052739 hydrogen Inorganic materials 0.000 description 28
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
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• 125000004181 carboxyalkyl group Chemical group 0.000 description 19
• 125000005843 halogen group Chemical group 0.000 description 19
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• 125000000304 alkynyl group Chemical group 0.000 description 16
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• 229940124597 therapeutic agent Drugs 0.000 description 16
• 125000004429 atom Chemical group 0.000 description 15
• 210000002216 heart Anatomy 0.000 description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
• 125000000547 substituted alkyl group Chemical group 0.000 description 13
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• 125000002252 acyl group Chemical group 0.000 description 12
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 12
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
• 239000000843 powder Substances 0.000 description 12
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 11
• 125000002947 alkylene group Chemical group 0.000 description 11
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
• 229910052805 deuterium Inorganic materials 0.000 description 11
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 11
• 208000024172 Cardiovascular disease Diseases 0.000 description 10
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• 229960000583 acetic acid Drugs 0.000 description 10
• 239000004480 active ingredient Substances 0.000 description 10
• 125000004104 aryloxy group Chemical group 0.000 description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• 150000003573 thiols Chemical class 0.000 description 10
• 206010019280 Heart failures Diseases 0.000 description 9
• 229930194542 Keto Natural products 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• 125000005553 heteroaryloxy group Chemical group 0.000 description 9
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• 125000000468 ketone group Chemical group 0.000 description 9
• 239000000546 pharmaceutical excipient Substances 0.000 description 9
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 9
• SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 8
• 125000000033 alkoxyamino group Chemical group 0.000 description 8
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• 125000005110 aryl thio group Chemical group 0.000 description 8
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 8
• 230000008901 benefit Effects 0.000 description 8
• 125000004468 heterocyclylthio group Chemical group 0.000 description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
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• 239000008194 pharmaceutical composition Substances 0.000 description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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