TW201713641A - 經取代之喹喏啉衍生物 - Google Patents

Info

Publication number

TW201713641A

TW201713641A TW105114781A TW105114781A TW201713641A TW 201713641 A TW201713641 A TW 201713641A TW 105114781 A TW105114781 A TW 105114781A TW 105114781 A TW105114781 A TW 105114781A TW 201713641 A TW201713641 A TW 201713641A

Authority

TW

Taiwan

Prior art keywords

methyl

indol

amine

quinoxaline

pyridin

Prior art date

2015-05-13

Links

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• Global Dossier
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• 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 280
• 238000011282 treatment Methods 0.000 claims abstract description 15
• 230000002265 prevention Effects 0.000 claims abstract description 9
• -1 -OH Chemical group 0.000 claims description 703
• 125000000217 alkyl group Chemical group 0.000 claims description 185
• 125000006413 ring segment Chemical group 0.000 claims description 182
• 125000002947 alkylene group Chemical group 0.000 claims description 150
• 125000005842 heteroatom Chemical group 0.000 claims description 133
• 125000003118 aryl group Chemical group 0.000 claims description 129
• 125000002950 monocyclic group Chemical group 0.000 claims description 106
• 125000004432 carbon atom Chemical group C* 0.000 claims description 100
• 125000004122 cyclic group Chemical group 0.000 claims description 93
• 125000000623 heterocyclic group Chemical group 0.000 claims description 93
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 89
• 239000000203 mixture Substances 0.000 claims description 83
• 238000000034 method Methods 0.000 claims description 82
• 150000003839 salts Chemical class 0.000 claims description 82
• 229910052727 yttrium Inorganic materials 0.000 claims description 79
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 77
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 71
• 125000002619 bicyclic group Chemical group 0.000 claims description 70
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 66
• 229910052799 carbon Inorganic materials 0.000 claims description 62
• 238000006243 chemical reaction Methods 0.000 claims description 62
• 229920006395 saturated elastomer Polymers 0.000 claims description 61
• 150000001721 carbon Chemical group 0.000 claims description 59
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 54
• 239000012453 solvate Substances 0.000 claims description 54
• 229910052757 nitrogen Inorganic materials 0.000 claims description 53
• 229940002612 prodrug Drugs 0.000 claims description 52
• 239000000651 prodrug Substances 0.000 claims description 52
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 47
• 150000001204 N-oxides Chemical class 0.000 claims description 46
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 44
• 238000005859 coupling reaction Methods 0.000 claims description 42
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 41
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 32
• 229910052717 sulfur Inorganic materials 0.000 claims description 32
• 229910052760 oxygen Inorganic materials 0.000 claims description 29
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 28
• 239000004480 active ingredient Substances 0.000 claims description 27
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 24
• 229910052794 bromium Inorganic materials 0.000 claims description 19
• 229910052801 chlorine Inorganic materials 0.000 claims description 19
• 239000002585 base Substances 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 229910052740 iodine Inorganic materials 0.000 claims description 18
• 206010028980 Neoplasm Diseases 0.000 claims description 17
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
• 201000011510 cancer Diseases 0.000 claims description 17
• 150000001412 amines Chemical class 0.000 claims description 16
• 239000003054 catalyst Substances 0.000 claims description 16
• 125000004076 pyridyl group Chemical group 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• MSGRFBKVMUKEGZ-UHFFFAOYSA-N quinoxalin-6-amine Chemical compound N1=CC=NC2=CC(N)=CC=C21 MSGRFBKVMUKEGZ-UHFFFAOYSA-N 0.000 claims description 15
• 102100022629 Fructose-2,6-bisphosphatase Human genes 0.000 claims description 14
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
• JOCNQSZSFFWVNY-UHFFFAOYSA-N 8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)N JOCNQSZSFFWVNY-UHFFFAOYSA-N 0.000 claims description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
• 101000823463 Homo sapiens Fructose-2,6-bisphosphatase Proteins 0.000 claims description 13
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 13
• 239000003153 chemical reaction reagent Substances 0.000 claims description 13
• 238000010168 coupling process Methods 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 13
• 238000006467 substitution reaction Methods 0.000 claims description 13
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
• 125000004429 atom Chemical group 0.000 claims description 12
• 230000008878 coupling Effects 0.000 claims description 12
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 11
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• 125000003386 piperidinyl group Chemical group 0.000 claims description 10
• 239000000126 substance Substances 0.000 claims description 10
• 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 9
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
• 125000001627 3 membered heterocyclic group Chemical group 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 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 8
• 125000004434 sulfur atom Chemical group 0.000 claims description 8
• 241000156724 Antirhea Species 0.000 claims description 7
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 229910019142 PO4 Inorganic materials 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 230000035479 physiological effects, processes and functions Effects 0.000 claims description 6
• UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
• 108010022678 Phosphofructokinase-2 Proteins 0.000 claims description 5
• 125000006384 methylpyridyl group Chemical group 0.000 claims description 5
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• 239000010452 phosphate Substances 0.000 claims description 5
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 5
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 5
• KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 4
• GHWMOYZSBLZJLB-UHFFFAOYSA-N 8-chloro-N-(dipyridin-3-ylmethyl)quinoxalin-6-amine Chemical compound N1=CC(=CC=C1)C(NC=1C=C2N=CC=NC2=C(C=1)Cl)C=1C=NC=CC=1 GHWMOYZSBLZJLB-UHFFFAOYSA-N 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 4
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
• SCMCRXOFIVZNTP-UHFFFAOYSA-N 4-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]methyl]benzamide Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1=CC=C(C(=O)N)C=C1 SCMCRXOFIVZNTP-UHFFFAOYSA-N 0.000 claims description 3
• 206010005003 Bladder cancer Diseases 0.000 claims description 3
• 229910014033 C-OH Inorganic materials 0.000 claims description 3
• 229910014570 C—OH Inorganic materials 0.000 claims description 3
• 208000032612 Glial tumor Diseases 0.000 claims description 3
• 206010018338 Glioma Diseases 0.000 claims description 3
• RAGOKBLNPWQUEM-UHFFFAOYSA-N N-[(5-bromopyridin-3-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound BrC=1C=C(C=NC=1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C RAGOKBLNPWQUEM-UHFFFAOYSA-N 0.000 claims description 3
• GHPSCZCQGHQCGK-UHFFFAOYSA-N N-methyl-8-(1-methylindol-6-yl)-N-(pyridin-3-ylmethyl)quinoxalin-6-amine Chemical compound CN(C=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)CC=1C=NC=CC=1 GHPSCZCQGHQCGK-UHFFFAOYSA-N 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
• 125000002393 azetidinyl group Chemical group 0.000 claims description 3
• 125000002837 carbocyclic group Chemical group 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 3
• 208000032839 leukemia Diseases 0.000 claims description 3
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
• KYPGHSSMJAMJJY-UHFFFAOYSA-N 1-[3-[(8-naphthalen-2-ylquinoxalin-6-yl)amino]pyrrolidin-1-yl]ethanone Chemical compound C1=C(C=CC2=CC=CC=C12)C=1C=C(C=C2N=CC=NC=12)NC1CN(CC1)C(C)=O KYPGHSSMJAMJJY-UHFFFAOYSA-N 0.000 claims description 2
• AZRLWZHSFXTCCN-UHFFFAOYSA-N 1-[4-[[8-(1-methylindol-2-yl)quinoxalin-6-yl]amino]piperidin-1-yl]ethanone Chemical compound CN1C(=CC2=CC=CC=C12)C=1C=C(C=C2N=CC=NC=12)NC1CCN(CC1)C(C)=O AZRLWZHSFXTCCN-UHFFFAOYSA-N 0.000 claims description 2
• WKBNHEPBBRMPMS-UHFFFAOYSA-N 1-[4-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]piperidin-1-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CCN(CC1)C(C)=O WKBNHEPBBRMPMS-UHFFFAOYSA-N 0.000 claims description 2
• GVXMHRWETMLFGH-UHFFFAOYSA-N 1-[4-[[[8-(4-bromophenyl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]piperidin-1-yl]ethanone Chemical compound BrC1=CC=C(C=C1)C=1C=C(C=C2N=CC=NC=12)NC(C1CCN(CC1)C(C)=O)C=1C=NC=CC=1 GVXMHRWETMLFGH-UHFFFAOYSA-N 0.000 claims description 2
• FPCRCXWDVCFANZ-UHFFFAOYSA-N 1-methyl-3,4-dihydropyridin-2-one Chemical compound CN1C=CCCC1=O FPCRCXWDVCFANZ-UHFFFAOYSA-N 0.000 claims description 2
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 2
• VKVGYCQJYFHCIL-JOCHJYFZSA-N 2-methoxy-4-[7-[[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]amino]quinoxalin-5-yl]benzamide Chemical compound COC1=C(C(=O)N)C=CC(=C1)C1=C2N=CC=NC2=CC(=C1)N[C@@H]1CCCC2=CC=CC=C12 VKVGYCQJYFHCIL-JOCHJYFZSA-N 0.000 claims description 2
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
• YZOPHMGNHRRUEQ-UHFFFAOYSA-N 3-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-3-pyridin-3-ylpropanoic acid Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(CC(=O)O)C=1C=NC=CC=1 YZOPHMGNHRRUEQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
• DEVBFXPTCZWTSB-UHFFFAOYSA-N 5-[7-[[(6-methoxypyridin-3-yl)-pyridin-3-ylmethyl]amino]quinoxalin-5-yl]-1,3-benzothiazol-2-amine Chemical compound NC=1SC2=C(N=1)C=C(C=C2)C=1C=C(C=C2N=CC=NC=12)NC(C=1C=NC=CC=1)C=1C=NC(=CC=1)OC DEVBFXPTCZWTSB-UHFFFAOYSA-N 0.000 claims description 2
• MKBWCVPATVDDQB-UHFFFAOYSA-N 5-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]-1H-pyridin-2-one Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C=1C=CC(NC=1)=O)C=1C=NC=CC=1 MKBWCVPATVDDQB-UHFFFAOYSA-N 0.000 claims description 2
• RNFATQCMRQOZTK-UHFFFAOYSA-N 5-[[[8-(3-methyl-1-benzothiophen-5-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]-1H-pyridin-2-one Chemical compound CC1=CSC2=C1C=C(C=C2)C=1C=C(C=C2N=CC=NC=12)NC(C=1C=CC(NC=1)=O)C=1C=NC=CC=1 RNFATQCMRQOZTK-UHFFFAOYSA-N 0.000 claims description 2
• JGPWWEKDZYWEEM-UHFFFAOYSA-N 7-chloro-5-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]quinoxaline Chemical compound ClC1=CC(=C2N=CC=NC2=C1)C1=C(C=C(C(=C1)SCC(F)(F)F)C)F JGPWWEKDZYWEEM-UHFFFAOYSA-N 0.000 claims description 2
• KINUSOGPSIQWAN-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(2-methylsulfonylpyridin-4-yl)-N-(pyridin-3-ylmethyl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=NC=CC(=C1)N(C=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)CC=1C=NC=CC=1 KINUSOGPSIQWAN-UHFFFAOYSA-N 0.000 claims description 2
• LQBUCAIQFUFGRU-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(4-methylsulfonylpyridin-2-yl)-N-(pyridin-3-ylmethyl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=CC(=NC=C1)N(C=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)CC=1C=NC=CC=1 LQBUCAIQFUFGRU-UHFFFAOYSA-N 0.000 claims description 2
• HTNPJFAHLPWLSY-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(4-methylsulfonylpyridin-3-yl)-N-(pyridin-3-ylmethyl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)N(C=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)CC=1C=NC=CC=1 HTNPJFAHLPWLSY-UHFFFAOYSA-N 0.000 claims description 2
• ZUVHBLLISPQAFW-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(5,6,7,8-tetrahydroisoquinolin-8-yl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CCCC=2C=CN=CC1=2 ZUVHBLLISPQAFW-UHFFFAOYSA-N 0.000 claims description 2
• LTWVMYOEEFBPRH-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(1-methylsulfonylpiperidin-4-yl)-pyridin-3-ylmethyl]quinoxalin-6-amine Chemical compound CS(=O)(=O)N1CCC(CC1)C(NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C=1C=NC=CC=1 LTWVMYOEEFBPRH-UHFFFAOYSA-N 0.000 claims description 2
• LPLAHTIXWYCFLA-MRXNPFEDSA-N 8-(1-methylindol-6-yl)-N-[(1R)-1-pyridin-3-ylethyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)N[C@H](C)C=1C=NC=CC=1 LPLAHTIXWYCFLA-MRXNPFEDSA-N 0.000 claims description 2
• GQAMQMWFBQHFPA-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(2-methylpyrazol-3-yl)methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1=CC=NN1C GQAMQMWFBQHFPA-UHFFFAOYSA-N 0.000 claims description 2
• ZRHXPXZBBCFNOH-IBGZPJMESA-N 8-(1-methylindol-6-yl)-N-[(3S)-1-pyrimidin-4-ylpyrrolidin-3-yl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CN(CC1)C1=NC=NC=C1 ZRHXPXZBBCFNOH-IBGZPJMESA-N 0.000 claims description 2
• FDWZLOMRNMUKOJ-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(4-pyrimidin-5-ylmorpholin-2-yl)methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C1=C2N=CC=NC2=CC(NCC2CN(CCO2)C2=CN=CN=C2)=C1 FDWZLOMRNMUKOJ-UHFFFAOYSA-N 0.000 claims description 2
• SZNJXBRXIADVBQ-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[[4-(1-methylpyrazol-4-yl)pyridin-3-yl]methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC=1C=NC=CC=1C=1C=NN(C=1)C SZNJXBRXIADVBQ-UHFFFAOYSA-N 0.000 claims description 2
• KOXQDNSUJQXYAF-JOCHJYFZSA-N 8-(5-amino-6-methylpyridin-3-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]quinoxalin-6-amine Chemical compound NC=1C=C(C=NC=1C)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CCCC2=CC=CC=C12 KOXQDNSUJQXYAF-JOCHJYFZSA-N 0.000 claims description 2
• RRXSYZFVDIRTFB-UHFFFAOYSA-N C[CH]C1=CC=C(OC)C=C1 Chemical group C[CH]C1=CC=C(OC)C=C1 RRXSYZFVDIRTFB-UHFFFAOYSA-N 0.000 claims description 2
• 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
• 206010009944 Colon cancer Diseases 0.000 claims description 2
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
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• MZUHOFZPDUAMNB-AREMUKBSSA-N N-[(R)-(6-methoxypyridin-3-yl)-(3-methyltriazol-4-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound COC1=CC=C(C=N1)[C@@H](NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C1=CN=NN1C MZUHOFZPDUAMNB-AREMUKBSSA-N 0.000 claims 1
• FZDSNKBGDZNFMH-AREMUKBSSA-N N-[(R)-(6-methoxypyridin-3-yl)-(3-methyltriazol-4-yl)methyl]-8-(3-methyl-1-benzothiophen-5-yl)quinoxalin-6-amine Chemical compound COC1=CC=C(C=N1)[C@@H](NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1)C1=CN=NN1C FZDSNKBGDZNFMH-AREMUKBSSA-N 0.000 claims 1
• MZUHOFZPDUAMNB-SANMLTNESA-N N-[(S)-(6-methoxypyridin-3-yl)-(3-methyltriazol-4-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound COC1=CC=C(C=N1)[C@H](NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C1=CN=NN1C MZUHOFZPDUAMNB-SANMLTNESA-N 0.000 claims 1
• 125000003047 N-acetyl group Chemical group 0.000 claims 1
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• IRQCWTBAVPJPAG-UHFFFAOYSA-N S1C=NC2=C1C=C(C=C2)C=2C=C(C=C1N=CC=NC21)NC(C)C=2C=NC=CC2.CN2C=CC1=CC=C(C=C21)C=2C=C(C=C1N=CC=NC21)NCC=2C=NNC2 Chemical compound S1C=NC2=C1C=C(C=C2)C=2C=C(C=C1N=CC=NC21)NC(C)C=2C=NC=CC2.CN2C=CC1=CC=C(C=C21)C=2C=C(C=C1N=CC=NC21)NCC=2C=NNC2 IRQCWTBAVPJPAG-UHFFFAOYSA-N 0.000 claims 1
• KVJISYSHPWXIRM-UHFFFAOYSA-N [5-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]methyl]pyridin-3-yl] 2-[7-(1-pyridin-3-ylethylamino)quinoxalin-5-yl]benzenesulfonate Chemical compound N1=CC(=CC=C1)C(C)NC1=CC(=C2N=CC=NC2=C1)C1=C(C=CC=C1)S(=O)(=O)OC=1C=NC=C(C=1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C KVJISYSHPWXIRM-UHFFFAOYSA-N 0.000 claims 1
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