NZ584311A - Phenyl and pyridyl substituted tetrazole c-met protein kinase inhibitors - Google Patents

Info

Publication number

NZ584311A

NZ584311A NZ584311A NZ58431108A NZ584311A NZ 584311 A NZ584311 A NZ 584311A NZ 584311 A NZ584311 A NZ 584311A NZ 58431108 A NZ58431108 A NZ 58431108A NZ 584311 A NZ584311 A NZ 584311A

Authority

NZ

New Zealand

Prior art keywords

compound

mmol

aliphatic

pharmaceutically acceptable

reaction

Prior art date

2007-10-03

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• 108010089836 Proto-Oncogene Proteins c-met Proteins 0.000 title claims abstract description 5
• 102000008022 Proto-Oncogene Proteins c-met Human genes 0.000 title claims abstract description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title description 16
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
• 239000003909 protein kinase inhibitor Substances 0.000 title description 2
• 125000004076 pyridyl group Chemical group 0.000 title description 2
• 150000003536 tetrazoles Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 339
• 150000003839 salts Chemical class 0.000 claims abstract description 32
• 238000000034 method Methods 0.000 claims abstract description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
• 238000002360 preparation method Methods 0.000 claims abstract description 17
• 208000035475 disorder Diseases 0.000 claims abstract description 16
• 230000000694 effects Effects 0.000 claims abstract description 13
• 239000012472 biological sample Substances 0.000 claims abstract description 10
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• 230000002062 proliferating effect Effects 0.000 claims abstract description 9
• 150000001721 carbon Chemical class 0.000 claims abstract description 7
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
• 206010017758 gastric cancer Diseases 0.000 claims abstract description 7
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• 208000003174 Brain Neoplasms Diseases 0.000 claims abstract description 6
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 6
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• 125000001931 aliphatic group Chemical group 0.000 claims description 59
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• 125000004429 atom Chemical group 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
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• 150000002431 hydrogen Chemical class 0.000 claims description 9
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• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
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• 125000001118 alkylidene group Chemical group 0.000 claims description 3
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
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• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims 1
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• 238000012986 modification Methods 0.000 claims 1
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• -1 tetrazole compounds Chemical class 0.000 abstract description 108
• 230000003247 decreasing effect Effects 0.000 abstract 1
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 93
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 58
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• 229910001868 water Inorganic materials 0.000 description 55
• 239000007787 solid Substances 0.000 description 50
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 49
• 238000005481 NMR spectroscopy Methods 0.000 description 48
• 239000011541 reaction mixture Substances 0.000 description 44
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• 235000019198 oils Nutrition 0.000 description 41
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
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• 230000002829 reductive effect Effects 0.000 description 32
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical group NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 31
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 28
• 125000001424 substituent group Chemical group 0.000 description 28
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• 101150041968 CDC13 gene Proteins 0.000 description 27
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