TW200406203A - N3 alkylated banzimidazole derivatives as MEK inhibitors - Google Patents

Info

Publication number

TW200406203A

TW200406203A TW092105719A TW92105719A TW200406203A TW 200406203 A TW200406203 A TW 200406203A TW 092105719 A TW092105719 A TW 092105719A TW 92105719 A TW92105719 A TW 92105719A TW 200406203 A TW200406203 A TW 200406203A

Authority

TW

Taiwan

Prior art keywords

heteroaryl

aryl

alkyl

heterocyclyl

nr3r4

Prior art date

2002-03-13

Links

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• 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 title abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 111
• 150000003839 salts Chemical class 0.000 claims abstract description 42
• 238000000034 method Methods 0.000 claims abstract description 37
• 239000000651 prodrug Substances 0.000 claims abstract description 27
• 229940002612 prodrug Drugs 0.000 claims abstract description 27
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 22
• 201000011510 cancer Diseases 0.000 claims abstract description 17
• 241000124008 Mammalia Species 0.000 claims abstract description 16
• -1 cyano, nitro, trifluorofluorenyl Chemical group 0.000 claims description 105
• 125000000623 heterocyclic group Chemical group 0.000 claims description 93
• 125000000217 alkyl group Chemical group 0.000 claims description 91
• 125000003118 aryl group Chemical group 0.000 claims description 90
• 125000001072 heteroaryl group Chemical group 0.000 claims description 88
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 55
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 51
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 48
• 239000002253 acid Substances 0.000 claims description 36
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
• 229910052736 halogen Inorganic materials 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 34
• 150000002367 halogens Chemical class 0.000 claims description 33
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 27
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
• 125000004043 oxo group Chemical group O=* 0.000 claims description 26
• 125000003342 alkenyl group Chemical group 0.000 claims description 22
• 125000000304 alkynyl group Chemical group 0.000 claims description 21
• 239000000203 mixture Substances 0.000 claims description 21
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 20
• 238000006467 substitution reaction Methods 0.000 claims description 20
• 150000001412 amines Chemical class 0.000 claims description 19
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 19
• 125000004429 atom Chemical group 0.000 claims description 18
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 15
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
• BPXYEYJNCXITEY-UHFFFAOYSA-N diazonio(trifluoromethoxy)azanide Chemical compound FC(F)(F)ON=[N+]=[N-] BPXYEYJNCXITEY-UHFFFAOYSA-N 0.000 claims description 13
• 125000002837 carbocyclic group Chemical group 0.000 claims description 12
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 11
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
• 239000012453 solvate Substances 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 230000000694 effects Effects 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 238000007347 radical substitution reaction Methods 0.000 claims description 7
• MYDAOWXYGPEPJT-UHFFFAOYSA-N 2-chloro-4-iodoaniline Chemical compound NC1=CC=C(I)C=C1Cl MYDAOWXYGPEPJT-UHFFFAOYSA-N 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 5
• COYPLDIXZODDDL-UHFFFAOYSA-N 3h-benzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=CNC2=C1 COYPLDIXZODDDL-UHFFFAOYSA-N 0.000 claims description 4
• YFTWRBJBZJQFNY-UHFFFAOYSA-N C1(CC1)COC1=C(C=2CC3=CC=CC=C3C2C=C1)N Chemical compound C1(CC1)COC1=C(C=2CC3=CC=CC=C3C2C=C1)N YFTWRBJBZJQFNY-UHFFFAOYSA-N 0.000 claims description 4
• 150000001540 azides Chemical class 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 125000000524 functional group Chemical group 0.000 claims description 3
• 239000007789 gas Substances 0.000 claims description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000005842 heteroatom Chemical group 0.000 claims description 2
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 10
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 3
• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical group ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
• QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 claims 1
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
• 101150072608 CVC1 gene Chemical group 0.000 claims 1
• IIKYKLLYIPXVHA-UHFFFAOYSA-N FC(F)O[N]OC(F)(F)F Chemical compound FC(F)O[N]OC(F)(F)F IIKYKLLYIPXVHA-UHFFFAOYSA-N 0.000 claims 1
• FJFKYJKLMACIHF-UHFFFAOYSA-N [C].NC1=CC=CC=C1 Chemical compound [C].NC1=CC=CC=C1 FJFKYJKLMACIHF-UHFFFAOYSA-N 0.000 claims 1
• 125000002393 azetidinyl group Chemical group 0.000 claims 1
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• 229960005181 morphine Drugs 0.000 claims 1
• RRHNGIRRWDWWQQ-UHFFFAOYSA-N n-iodoaniline Chemical compound INC1=CC=CC=C1 RRHNGIRRWDWWQQ-UHFFFAOYSA-N 0.000 claims 1
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• 238000006243 chemical reaction Methods 0.000 description 21
• 230000002829 reductive effect Effects 0.000 description 21
• 239000007787 solid Substances 0.000 description 21
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
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• 210000004027 cell Anatomy 0.000 description 19
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
• 239000003112 inhibitor Substances 0.000 description 15
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• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 10
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
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• 238000004293 19F NMR spectroscopy Methods 0.000 description 6
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
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