JP5728683B2 - チロシンスレオニンキナーゼ阻害剤としての置換アミノキノキサリン - Google Patents

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Publication number

JP5728683B2

JP5728683B2 JP2012527219A JP2012527219A JP5728683B2 JP 5728683 B2 JP5728683 B2 JP 5728683B2 JP 2012527219 A JP2012527219 A JP 2012527219A JP 2012527219 A JP2012527219 A JP 2012527219A JP 5728683 B2 JP5728683 B2 JP 5728683B2

Authority

JP

Japan

Prior art keywords

quinoxalin

phenyl

piperazin

alkyl

pyridin

Prior art date

2009-09-04

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.)

Expired - Fee Related

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• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 title description 2
• 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 title description 2
• 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 title description 2
• 229940043355 kinase inhibitor Drugs 0.000 title description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
• YOWAEZWWQFSEJD-UHFFFAOYSA-N quinoxalin-2-amine Chemical class C1=CC=CC2=NC(N)=CN=C21 YOWAEZWWQFSEJD-UHFFFAOYSA-N 0.000 title description 2
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 title description 2
• -1 hydroxyl- Chemical group 0.000 claims description 517
• 150000001875 compounds Chemical class 0.000 claims description 203
• 125000005843 halogen group Chemical group 0.000 claims description 97
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 96
• 125000001424 substituent group Chemical group 0.000 claims description 76
• 239000000203 mixture Substances 0.000 claims description 70
• 125000003118 aryl group Chemical group 0.000 claims description 68
• 125000001072 heteroaryl group Chemical group 0.000 claims description 61
• 238000000034 method Methods 0.000 claims description 61
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 58
• 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 48
• 238000002360 preparation method Methods 0.000 claims description 45
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 44
• 150000003839 salts Chemical class 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 38
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 229910052757 nitrogen Inorganic materials 0.000 claims description 37
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
• 206010028980 Neoplasm Diseases 0.000 claims description 32
• 201000010099 disease Diseases 0.000 claims description 30
• 238000011282 treatment Methods 0.000 claims description 30
• 239000002904 solvent Substances 0.000 claims description 26
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 238000006243 chemical reaction Methods 0.000 claims description 23
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 21
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 19
• 125000005842 heteroatom Chemical group 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 17
• 230000004663 cell proliferation Effects 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• 230000004083 survival effect Effects 0.000 claims description 17
• 239000012453 solvate Substances 0.000 claims description 16
• 206010027476 Metastases Diseases 0.000 claims description 15
• 230000010261 cell growth Effects 0.000 claims description 15
• 230000001413 cellular effect Effects 0.000 claims description 15
• 230000028709 inflammatory response Effects 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
• 239000000126 substance Substances 0.000 claims description 14
• 230000024932 T cell mediated immunity Effects 0.000 claims description 13
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
• 208000032839 leukemia Diseases 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 230000002265 prevention Effects 0.000 claims description 8
• 125000006413 ring segment Chemical group 0.000 claims description 8
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• 150000001204 N-oxides Chemical class 0.000 claims description 7
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• 150000004677 hydrates Chemical class 0.000 claims description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
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• 229960001592 paclitaxel Drugs 0.000 claims description 6
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 6
• 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims description 5
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• 206010059282 Metastases to central nervous system Diseases 0.000 claims description 5
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• PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 claims description 4
• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 4
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 4
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 230000001404 mediated effect Effects 0.000 claims description 4
• 229960004641 rituximab Drugs 0.000 claims description 4
• RELDELLUOBLSTB-UHFFFAOYSA-N 2-phenyl-n-[4-[3-(4-pyrazin-2-ylpiperazin-1-yl)quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC2)C=2N=CC=NC=2)C=CC=1NC(=O)CC1=CC=CC=C1 RELDELLUOBLSTB-UHFFFAOYSA-N 0.000 claims description 3
• WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 3
• STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims description 3
• 108010006654 Bleomycin Proteins 0.000 claims description 3
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 3
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 3
• XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 claims description 3
• XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 claims description 3
• JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 3
• VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 3
• 239000004202 carbamide Substances 0.000 claims description 3
• 229960004562 carboplatin Drugs 0.000 claims description 3
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 3
• 229960004316 cisplatin Drugs 0.000 claims description 3
• 229960004397 cyclophosphamide Drugs 0.000 claims description 3
• 229960000684 cytarabine Drugs 0.000 claims description 3
• 229960003668 docetaxel Drugs 0.000 claims description 3
• 229960004679 doxorubicin Drugs 0.000 claims description 3
• 229960005420 etoposide Drugs 0.000 claims description 3
• VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 3
• GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 claims description 3
• 229960002949 fluorouracil Drugs 0.000 claims description 3
• MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 claims description 3
• 229960002074 flutamide Drugs 0.000 claims description 3
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• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims description 3
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• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims description 3
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 3
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• GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims description 2
• GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims description 2
• 229960001561 bleomycin Drugs 0.000 claims description 2
• OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims description 2
• GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims description 2
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• JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 2
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• UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 claims description 2
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• ZIUUDTYYEITUSJ-UHFFFAOYSA-N n-(methylsulfamoyl)-4-(3-morpholin-4-ylquinoxalin-6-yl)aniline Chemical compound C1=CC(NS(=O)(=O)NC)=CC=C1C1=CC=C(N=CC(=N2)N3CCOCC3)C2=C1 ZIUUDTYYEITUSJ-UHFFFAOYSA-N 0.000 claims description 2
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• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 2
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
• 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims 2
• LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims 1
• UCHFYKAEZIDDEO-UHFFFAOYSA-N 1-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperidine-3-carboxamide Chemical compound CC1=C(O)C(C)=CC(C=2C=C3N=C(C=NC3=CC=2)N2CC(CCC2)C(N)=O)=C1 UCHFYKAEZIDDEO-UHFFFAOYSA-N 0.000 claims 1
• RGRFZRNNMYWGJP-UHFFFAOYSA-N 1-[7-(4-hydroxy-3,5-dimethylphenyl)quinoxalin-2-yl]piperidine-4-carbonitrile Chemical compound CC1=C(O)C(C)=CC(C=2C=C3N=C(C=NC3=CC=2)N2CCC(CC2)C#N)=C1 RGRFZRNNMYWGJP-UHFFFAOYSA-N 0.000 claims 1
• DOGMQEFGXZLGMX-UHFFFAOYSA-N 1-[7-(4-hydroxyphenyl)quinoxalin-2-yl]piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C1=CN=C(C=CC(=C2)C=3C=CC(O)=CC=3)C2=N1 DOGMQEFGXZLGMX-UHFFFAOYSA-N 0.000 claims 1
• BCEFWCAEAOWDIB-UHFFFAOYSA-N 1-methyl-n-[4-[3-(4-pyrazin-2-ylpiperazin-1-yl)quinoxalin-6-yl]phenyl]pyrazole-3-carboxamide Chemical compound CN1C=CC(C(=O)NC=2C=CC(=CC=2)C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC2)C=2N=CC=NC=2)=N1 BCEFWCAEAOWDIB-UHFFFAOYSA-N 0.000 claims 1
• HDUDRJHNUNZJII-UHFFFAOYSA-N 1-pyridin-2-yl-3-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]urea Chemical compound C=1C=CC=NC=1NC(=O)NC(C=C1)=CC=C1C(C=C1N=2)=CC=C1N=CC=2N(CC1)CCN1CC1=CC=CN=C1 HDUDRJHNUNZJII-UHFFFAOYSA-N 0.000 claims 1
• IYIZDGJMJKPLMC-UHFFFAOYSA-N 2,4-dioxo-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]-1h-pyrimidine-6-carboxamide Chemical compound C=1C(=O)NC(=O)NC=1C(=O)NC(C=C1)=CC=C1C(C=C1N=2)=CC=C1N=CC=2N(CC1)CCN1CC1=CC=CN=C1 IYIZDGJMJKPLMC-UHFFFAOYSA-N 0.000 claims 1
• AUFATHXTBFEYKK-UHFFFAOYSA-N 2,6-dimethyl-4-(3-morpholin-4-ylquinoxalin-6-yl)phenol Chemical compound CC1=C(O)C(C)=CC(C=2C=C3N=C(C=NC3=CC=2)N2CCOCC2)=C1 AUFATHXTBFEYKK-UHFFFAOYSA-N 0.000 claims 1
• JVNRJBVEGKXHCB-UHFFFAOYSA-N 2,6-dimethyl-4-[3-(3-pyrazol-1-ylazetidin-1-yl)quinoxalin-6-yl]phenol Chemical compound CC1=C(O)C(C)=CC(C=2C=C3N=C(C=NC3=CC=2)N2CC(C2)N2N=CC=C2)=C1 JVNRJBVEGKXHCB-UHFFFAOYSA-N 0.000 claims 1
• LJLLUGBQBQLFNA-UHFFFAOYSA-N 2,6-dimethyl-4-[3-(4-methylsulfonylpiperazin-1-yl)quinoxalin-6-yl]phenol Chemical compound CC1=C(O)C(C)=CC(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC2)S(C)(=O)=O)=C1 LJLLUGBQBQLFNA-UHFFFAOYSA-N 0.000 claims 1
• NRDONJXAHPAFQR-UHFFFAOYSA-N 2,6-dimethyl-4-[3-(4-pyrazin-2-ylpiperazin-1-yl)quinoxalin-6-yl]phenol Chemical compound CC1=C(O)C(C)=CC(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC2)C=2N=CC=NC=2)=C1 NRDONJXAHPAFQR-UHFFFAOYSA-N 0.000 claims 1
• RIOXYGCPNRCJLP-UHFFFAOYSA-N 2-(1,2-benzoxazol-3-yl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound N=1OC2=CC=CC=C2C=1CC(=O)NC(C=C1)=CC=C1C(C=C1N=2)=CC=C1N=CC=2N(CC1)CCN1CC1=CC=CN=C1 RIOXYGCPNRCJLP-UHFFFAOYSA-N 0.000 claims 1
• ZVWOYXKJUNSYAE-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=C2OCOC2=CC=1CC(=O)NC(C=C1)=CC=C1C(C=C1N=2)=CC=C1N=CC=2N(CC1)CCN1CC1=CC=CN=C1 ZVWOYXKJUNSYAE-UHFFFAOYSA-N 0.000 claims 1
• IARILKNHLNCDFT-UHFFFAOYSA-N 2-(1h-indol-3-yl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1NC2=CC=CC=C2C=1CC(=O)NC(C=C1)=CC=C1C(C=C1N=2)=CC=C1N=CC=2N(CC1)CCN1CC1=CC=CN=C1 IARILKNHLNCDFT-UHFFFAOYSA-N 0.000 claims 1
• QKMMFVCMPYEDSE-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound ClC1=CC=CC=C1CC(=O)NC1=CC=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=C1 QKMMFVCMPYEDSE-UHFFFAOYSA-N 0.000 claims 1
• MDFDXMKRGAHAKI-UHFFFAOYSA-N 2-(2-fluorophenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound FC1=CC=CC=C1CC(=O)NC1=CC=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=C1 MDFDXMKRGAHAKI-UHFFFAOYSA-N 0.000 claims 1
• WPXUMLUMLZFRME-UHFFFAOYSA-N 2-(2-methoxyphenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound COC1=CC=CC=C1CC(=O)NC1=CC=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=C1 WPXUMLUMLZFRME-UHFFFAOYSA-N 0.000 claims 1
• CGAFBIMGGJRINH-UHFFFAOYSA-N 2-(2-methylphenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound CC1=CC=CC=C1CC(=O)NC1=CC=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=C1 CGAFBIMGGJRINH-UHFFFAOYSA-N 0.000 claims 1
• UMPXHNHJBBMWIZ-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound ClC1=CC=CC(CC(=O)NC=2C=CC(=CC=2)C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)=C1 UMPXHNHJBBMWIZ-UHFFFAOYSA-N 0.000 claims 1
• LYEWCDAFDXWRHT-UHFFFAOYSA-N 2-(3-cyanophenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=CC=1NC(=O)CC1=CC=CC(C#N)=C1 LYEWCDAFDXWRHT-UHFFFAOYSA-N 0.000 claims 1
• LVLXMKIYHHBVPC-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound FC1=CC=CC(CC(=O)NC=2C=CC(=CC=2)C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)=C1 LVLXMKIYHHBVPC-UHFFFAOYSA-N 0.000 claims 1
• YBYAHCDNTOLCNH-UHFFFAOYSA-N 2-(3-methoxyphenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound COC1=CC=CC(CC(=O)NC=2C=CC(=CC=2)C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)=C1 YBYAHCDNTOLCNH-UHFFFAOYSA-N 0.000 claims 1
• LHCKBYXKWWFMGP-UHFFFAOYSA-N 2-(3-methyl-1,2-oxazol-5-yl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound O1N=C(C)C=C1CC(=O)NC1=CC=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=C1 LHCKBYXKWWFMGP-UHFFFAOYSA-N 0.000 claims 1
• DXVMOKNJMRLGNS-UHFFFAOYSA-N 2-(3-methylphenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound CC1=CC=CC(CC(=O)NC=2C=CC(=CC=2)C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)=C1 DXVMOKNJMRLGNS-UHFFFAOYSA-N 0.000 claims 1
• PGCCYYLMNQKRMV-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C1=CC(Cl)=CC=C1CC(=O)NC1=CC=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=C1 PGCCYYLMNQKRMV-UHFFFAOYSA-N 0.000 claims 1
• MOCZSNZLFHLICQ-UHFFFAOYSA-N 2-(4-cyanophenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=CC=1NC(=O)CC1=CC=C(C#N)C=C1 MOCZSNZLFHLICQ-UHFFFAOYSA-N 0.000 claims 1
• WMKBZSXAPKNFGL-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C1=CC(F)=CC=C1CC(=O)NC1=CC=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=C1 WMKBZSXAPKNFGL-UHFFFAOYSA-N 0.000 claims 1
• YXWQACAKMOGGKX-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=C1 YXWQACAKMOGGKX-UHFFFAOYSA-N 0.000 claims 1
• SCXQFVRBOWCVFS-UHFFFAOYSA-N 2-(4-methylphenyl)-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C1=CC(C)=CC=C1CC(=O)NC1=CC=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=C1 SCXQFVRBOWCVFS-UHFFFAOYSA-N 0.000 claims 1
• MCWKEJLYBFQDPM-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C1=CC(N(C)C)=CC=C1CC(=O)NC1=CC=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=C1 MCWKEJLYBFQDPM-UHFFFAOYSA-N 0.000 claims 1
• VOXBZHOHGGBLCQ-UHFFFAOYSA-N 2-amino-3,7-dihydropurine-6-thione;hydrate Chemical compound O.N1C(N)=NC(=S)C2=C1N=CN2.N1C(N)=NC(=S)C2=C1N=CN2 VOXBZHOHGGBLCQ-UHFFFAOYSA-N 0.000 claims 1
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
• YOVOOPJLAREQCW-UHFFFAOYSA-N 2-cyclohexyl-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=CC=1NC(=O)CC1CCCCC1 YOVOOPJLAREQCW-UHFFFAOYSA-N 0.000 claims 1
• ILAKEFHLDQHGQO-UHFFFAOYSA-N 2-cyclopropyl-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=CC=1NC(=O)CC1CC1 ILAKEFHLDQHGQO-UHFFFAOYSA-N 0.000 claims 1
• IWOICBDSACRROY-UHFFFAOYSA-N 2-fluoro-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]benzamide Chemical compound FC1=CC=CC=C1C(=O)NC1=CC=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3C=NC=CC=3)CC2)C=C1 IWOICBDSACRROY-UHFFFAOYSA-N 0.000 claims 1
• ZCASZLBJZOHHQA-UHFFFAOYSA-N 2-hydroxy-2-phenyl-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=CC=CC=1C(O)C(=O)NC(C=C1)=CC=C1C(C=C1N=2)=CC=C1N=CC=2N(CC1)CCN1CC1=CC=CN=C1 ZCASZLBJZOHHQA-UHFFFAOYSA-N 0.000 claims 1
• AJKPHEHEXHQYQO-UHFFFAOYSA-N 2-hydroxy-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)CO)=CC=C1C1=CC=C(N=CC(=N2)N3CCN(CC=4C=NC=CC=4)CC3)C2=C1 AJKPHEHEXHQYQO-UHFFFAOYSA-N 0.000 claims 1
• WXQILYZRAXSYFC-UHFFFAOYSA-N 2-hydroxy-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]propanamide Chemical compound C1=CC(NC(=O)C(O)C)=CC=C1C1=CC=C(N=CC(=N2)N3CCN(CC=4C=NC=CC=4)CC3)C2=C1 WXQILYZRAXSYFC-UHFFFAOYSA-N 0.000 claims 1
• ANORWADROQQRFK-UHFFFAOYSA-N 2-methoxy-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)COC)=CC=C1C1=CC=C(N=CC(=N2)N3CCN(CC=4C=NC=CC=4)CC3)C2=C1 ANORWADROQQRFK-UHFFFAOYSA-N 0.000 claims 1
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
• KCHGWYHUOLDURG-UHFFFAOYSA-N 2-methyl-4-(3-piperidin-1-ylquinoxalin-6-yl)aniline Chemical compound C1=C(N)C(C)=CC(C=2C=C3N=C(C=NC3=CC=2)N2CCCCC2)=C1 KCHGWYHUOLDURG-UHFFFAOYSA-N 0.000 claims 1
• HSTWPMMBLPFDQM-UHFFFAOYSA-N 2-methyl-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]butanamide Chemical compound C1=CC(NC(=O)C(C)CC)=CC=C1C1=CC=C(N=CC(=N2)N3CCN(CC=4C=NC=CC=4)CC3)C2=C1 HSTWPMMBLPFDQM-UHFFFAOYSA-N 0.000 claims 1
• MHFVQIBFYGJYTF-UHFFFAOYSA-N 2-phenyl-n-[4-[3-(2-phenylpyrrolidin-1-yl)quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=C(C=NC3=CC=2)N2C(CCC2)C=2C=CC=CC=2)C=CC=1NC(=O)CC1=CC=CC=C1 MHFVQIBFYGJYTF-UHFFFAOYSA-N 0.000 claims 1
• ANLGQBZFGCTOOG-UHFFFAOYSA-N 2-phenyl-n-[4-[3-(4-phenylpiperazin-1-yl)quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC2)C=2C=CC=CC=2)C=CC=1NC(=O)CC1=CC=CC=C1 ANLGQBZFGCTOOG-UHFFFAOYSA-N 0.000 claims 1
• ZPDMTOVAQYYPQM-UHFFFAOYSA-N 2-phenyl-n-[4-[3-(4-phenylpiperidin-1-yl)quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=C(C=NC3=CC=2)N2CCC(CC2)C=2C=CC=CC=2)C=CC=1NC(=O)CC1=CC=CC=C1 ZPDMTOVAQYYPQM-UHFFFAOYSA-N 0.000 claims 1
• WSUYAIXVNHPVDN-UHFFFAOYSA-N 2-phenyl-n-[4-[3-[3-(trifluoromethyl)pyrrolidin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C1C(C(F)(F)F)CCN1C1=CN=C(C=CC(=C2)C=3C=CC(NC(=O)CC=4C=CC=CC=4)=CC=3)C2=N1 WSUYAIXVNHPVDN-UHFFFAOYSA-N 0.000 claims 1
• SJAPHLNNTFWMFD-UHFFFAOYSA-N 2-phenyl-n-[4-[3-[4-(1-phenylethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=CC=CC=1C(C)N(CC1)CCN1C(N=C1C=2)=CN=C1C=CC=2C(C=C1)=CC=C1NC(=O)CC1=CC=CC=C1 SJAPHLNNTFWMFD-UHFFFAOYSA-N 0.000 claims 1
• LJVJNNAZZCDVJG-UHFFFAOYSA-N 2-phenyl-n-[4-[3-[4-(2-phenylethyl)-1,4-diazepan-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CCC=3C=CC=CC=3)CCC2)C=CC=1NC(=O)CC1=CC=CC=C1 LJVJNNAZZCDVJG-UHFFFAOYSA-N 0.000 claims 1
• AOVDNYMWNMIQOX-UHFFFAOYSA-N 2-phenyl-n-[4-[3-[4-(2-phenylethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CCC=3C=CC=CC=3)CC2)C=CC=1NC(=O)CC1=CC=CC=C1 AOVDNYMWNMIQOX-UHFFFAOYSA-N 0.000 claims 1
• JECQQRCISAMGLE-UHFFFAOYSA-N 2-phenyl-n-[4-[3-[4-(3-phenylpropyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CCCC=3C=CC=CC=3)CC2)C=CC=1NC(=O)CC1=CC=CC=C1 JECQQRCISAMGLE-UHFFFAOYSA-N 0.000 claims 1
• JZVIQYKQOONCPC-UHFFFAOYSA-N 2-phenyl-n-[4-[3-[4-(pyridin-2-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=C(C=NC3=CC=2)N2CCN(CC=3N=CC=CC=3)CC2)C=CC=1NC(=O)CC1=CC=CC=C1 JZVIQYKQOONCPC-UHFFFAOYSA-N 0.000 claims 1
• QKYXREYWIOMTOF-UHFFFAOYSA-N 2-phenyl-n-[4-[3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]quinoxalin-6-yl]phenyl]propanamide Chemical compound C=1C=CC=CC=1C(C)C(=O)NC(C=C1)=CC=C1C(C=C1N=2)=CC=C1N=CC=2N(CC1)CCN1CC1=CC=CN=C1 QKYXREYWIOMTOF-UHFFFAOYSA-N 0.000 claims 1
• SVKQSBNUXKNGOF-UHFFFAOYSA-N 2-phenyl-n-[4-[3-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]quinoxalin-6-yl]phenyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCN(C=2N=C3C=C(C=CC3=NC=2)C=2C=CC(NC(=O)CC=3C=CC=CC=3)=CC=2)CC1 SVKQSBNUXKNGOF-UHFFFAOYSA-N 0.000 claims 1
• PYRQLTGDWMLQRI-UHFFFAOYSA-N 3-(3-morpholin-4-ylquinoxalin-6-yl)phenol Chemical compound OC1=CC=CC(C=2C=C3N=C(C=NC3=CC=2)N2CCOCC2)=C1 PYRQLTGDWMLQRI-UHFFFAOYSA-N 0.000 claims 1
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