JP2010538094A - チロシンキナーゼ阻害剤としてのピラゾロピリジン類 - Google Patents

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Publication number

JP2010538094A

JP2010538094A JP2010524200A JP2010524200A JP2010538094A JP 2010538094 A JP2010538094 A JP 2010538094A JP 2010524200 A JP2010524200 A JP 2010524200A JP 2010524200 A JP2010524200 A JP 2010524200A JP 2010538094 A JP2010538094 A JP 2010538094A

Authority

JP

Japan

Prior art keywords

alkyl

compound

heteroaryl

substituted

aryl

Prior art date

2007-09-06

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.)

Withdrawn

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• 150000005229 pyrazolopyridines Chemical class 0.000 title description 2
• 239000005483 tyrosine kinase inhibitor Substances 0.000 title description 2
• 229940121358 tyrosine kinase inhibitor Drugs 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 268
• 238000000034 method Methods 0.000 claims abstract description 121
• 150000003839 salts Chemical class 0.000 claims abstract description 40
• 238000011282 treatment Methods 0.000 claims abstract description 35
• 102000027426 receptor tyrosine kinases Human genes 0.000 claims abstract description 25
• 108091008598 receptor tyrosine kinases Proteins 0.000 claims abstract description 25
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 201
• -1 carbocycle Chemical group 0.000 claims description 199
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 144
• 239000000203 mixture Substances 0.000 claims description 117
• 125000000217 alkyl group Chemical group 0.000 claims description 109
• 125000001072 heteroaryl group Chemical group 0.000 claims description 101
• 125000003118 aryl group Chemical group 0.000 claims description 92
• 125000000623 heterocyclic group Chemical group 0.000 claims description 91
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 68
• 206010028980 Neoplasm Diseases 0.000 claims description 56
• 125000005842 heteroatom Chemical group 0.000 claims description 54
• 229910052799 carbon Inorganic materials 0.000 claims description 48
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
• 201000011510 cancer Diseases 0.000 claims description 46
• 229910052739 hydrogen Inorganic materials 0.000 claims description 46
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 43
• 229920006395 saturated elastomer Polymers 0.000 claims description 42
• 229910052801 chlorine Inorganic materials 0.000 claims description 40
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
• 208000035475 disorder Diseases 0.000 claims description 36
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 35
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 35
• 229910052731 fluorine Inorganic materials 0.000 claims description 35
• 229910052794 bromium Inorganic materials 0.000 claims description 34
• 229910005965 SO 2 Inorganic materials 0.000 claims description 33
• 125000004429 atom Chemical group 0.000 claims description 33
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• 229910052740 iodine Inorganic materials 0.000 claims description 30
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
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• 230000000694 effects Effects 0.000 claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims description 23
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
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• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
• 125000006413 ring segment Chemical group 0.000 claims description 13
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• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 5
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• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
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• 230000001028 anti-proliverative effect Effects 0.000 claims description 4
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
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• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
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• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 4
• 229910052727 yttrium Inorganic materials 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
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• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
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• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
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• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 2
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• 239000002207 metabolite Substances 0.000 abstract description 26
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• 238000011065 in-situ storage Methods 0.000 abstract 1
• 210000004962 mammalian cell Anatomy 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 148
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 116
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
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• 235000019439 ethyl acetate Nutrition 0.000 description 45
• 238000009472 formulation Methods 0.000 description 42
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
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• 229940002612 prodrug Drugs 0.000 description 37
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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
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• 238000005481 NMR spectroscopy Methods 0.000 description 30
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• 238000003818 flash chromatography Methods 0.000 description 29
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
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• 239000011734 sodium Substances 0.000 description 24
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• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 18
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
• 239000002585 base Substances 0.000 description 18
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• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 17
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 17
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
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