JP2018515612A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018515612A5 JP2018515612A5 JP2018511333A JP2018511333A JP2018515612A5 JP 2018515612 A5 JP2018515612 A5 JP 2018515612A5 JP 2018511333 A JP2018511333 A JP 2018511333A JP 2018511333 A JP2018511333 A JP 2018511333A JP 2018515612 A5 JP2018515612 A5 JP 2018515612A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- quinoxalin
- indol
- amine
- pyridin
- Prior art date
- 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.)
- Pending
Links
- -1 3- (methylamino) -4-methylphenyl Chemical group 0.000 claims 311
- 125000006413 ring segment Chemical group 0.000 claims 84
- 150000001875 compounds Chemical class 0.000 claims 55
- 125000004122 cyclic group Chemical group 0.000 claims 48
- 125000003118 aryl group Chemical group 0.000 claims 45
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 41
- 150000003839 salts Chemical class 0.000 claims 41
- 125000004432 carbon atom Chemical group C* 0.000 claims 40
- 125000002950 monocyclic group Chemical group 0.000 claims 40
- 239000012453 solvate Substances 0.000 claims 40
- 150000001204 N-oxides Chemical class 0.000 claims 39
- 239000000203 mixture Substances 0.000 claims 39
- 229940002612 prodrug Drugs 0.000 claims 39
- 239000000651 prodrug Substances 0.000 claims 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 37
- 125000005842 heteroatom Chemical group 0.000 claims 34
- 125000002619 bicyclic group Chemical group 0.000 claims 33
- 125000002947 alkylene group Chemical group 0.000 claims 27
- 229910052799 carbon Inorganic materials 0.000 claims 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 27
- 150000001721 carbon Chemical group 0.000 claims 26
- MSGRFBKVMUKEGZ-UHFFFAOYSA-N quinoxalin-6-amine Chemical compound N1=CC=NC2=CC(N)=CC=C21 MSGRFBKVMUKEGZ-UHFFFAOYSA-N 0.000 claims 26
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 24
- 125000000623 heterocyclic group Chemical group 0.000 claims 23
- 229910052757 nitrogen Inorganic materials 0.000 claims 23
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 14
- 229910052717 sulfur Inorganic materials 0.000 claims 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 229920006395 saturated elastomer Polymers 0.000 claims 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 12
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 11
- 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 11
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 10
- 238000005859 coupling reaction Methods 0.000 claims 8
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000001627 3 membered heterocyclic group Chemical group 0.000 claims 3
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 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 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- BLRHMMGNCXNXJL-UHFFFAOYSA-N 1-methylindole Chemical compound C1=CC=C2N(C)C=CC2=C1 BLRHMMGNCXNXJL-UHFFFAOYSA-N 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims 2
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 102100022629 Fructose-2,6-bisphosphatase Human genes 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 claims 2
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims 1
- MRILJHDWDOHJBW-LJQANCHMSA-N 1-[(3R)-3-[[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)N[C@H]1CN(CCC1)C(C)=O MRILJHDWDOHJBW-LJQANCHMSA-N 0.000 claims 1
- LJLXIGDGNXYCDV-GOSISDBHSA-N 1-[(3R)-3-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)N[C@H]1CN(CC1)C(C)=O LJLXIGDGNXYCDV-GOSISDBHSA-N 0.000 claims 1
- MRILJHDWDOHJBW-IBGZPJMESA-N 1-[(3S)-3-[[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)N[C@@H]1CN(CCC1)C(C)=O MRILJHDWDOHJBW-IBGZPJMESA-N 0.000 claims 1
- LJLXIGDGNXYCDV-SFHVURJKSA-N 1-[(3S)-3-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CN(CC1)C(C)=O LJLXIGDGNXYCDV-SFHVURJKSA-N 0.000 claims 1
- FBMAOSUUAWXYJE-KRWDZBQOSA-N 1-[(3S)-3-[[8-(4-methyl-2,3-dihydro-1H-quinoxalin-6-yl)quinoxalin-6-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound CN1CCNC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CN(CC1)C(C)=O FBMAOSUUAWXYJE-KRWDZBQOSA-N 0.000 claims 1
- BPRTUEFDZXCPHY-SFHVURJKSA-N 1-[(3S)-3-[[8-(5-methyl-1,2,3,4-tetrahydro-1,5-benzodiazepin-7-yl)quinoxalin-6-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound CN1CCCNC2=C1C=C(C=C2)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CN(CC1)C(C)=O BPRTUEFDZXCPHY-SFHVURJKSA-N 0.000 claims 1
- OMCCXDFEBMMDFF-KRWDZBQOSA-N 1-[(3S)-3-[[8-[3-(dimethylamino)-4-methoxyphenyl]quinoxalin-6-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound CN(C=1C=C(C=CC=1OC)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CN(CC1)C(C)=O)C OMCCXDFEBMMDFF-KRWDZBQOSA-N 0.000 claims 1
- MLIMVZBWJTZDOP-SFHVURJKSA-N 1-[(3S)-3-[[8-[3-(dimethylamino)-4-methylphenyl]quinoxalin-6-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound CN(C=1C=C(C=CC=1C)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CN(CC1)C(C)=O)C MLIMVZBWJTZDOP-SFHVURJKSA-N 0.000 claims 1
- BYDMEFPTGUXFDD-UHFFFAOYSA-N 1-[2-[[[8-(1-methylindol-5-yl)quinoxalin-6-yl]amino]methyl]piperidin-1-yl]ethanone Chemical compound CN1C=CC2=CC(=CC=C12)C=1C=C(C=C2N=CC=NC=12)NCC1N(CCCC1)C(C)=O BYDMEFPTGUXFDD-UHFFFAOYSA-N 0.000 claims 1
- WQDLBJNQHLWHDU-UHFFFAOYSA-N 1-[2-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]methyl]morpholin-4-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1CN(CCO1)C(C)=O WQDLBJNQHLWHDU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- UOBLHNSVJPQDNB-PEFOLFAWSA-N 1-[3-[(R)-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]piperidin-1-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)N[C@H](C1CN(CCC1)C(C)=O)C=1C=NC=CC=1 UOBLHNSVJPQDNB-PEFOLFAWSA-N 0.000 claims 1
- QDOJTJXRICIWRA-UHFFFAOYSA-N 1-[3-[[8-(1-methyl-3,4-dihydro-2H-quinolin-7-yl)quinoxalin-6-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound CN1CCCC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CN(CC1)C(C)=O QDOJTJXRICIWRA-UHFFFAOYSA-N 0.000 claims 1
- FYVAXSUPDZBRHT-UHFFFAOYSA-N 1-[3-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]azetidin-1-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CN(C1)C(C)=O FYVAXSUPDZBRHT-UHFFFAOYSA-N 0.000 claims 1
- BESVKIWYLYJVMZ-UHFFFAOYSA-N 1-[3-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]pyrrolidin-1-yl]propan-1-one Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CN(CC1)C(CC)=O BESVKIWYLYJVMZ-UHFFFAOYSA-N 0.000 claims 1
- CMGJENIKHHAEFV-UHFFFAOYSA-N 1-[3-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]-pyridin-3-ylamino]methyl]piperidin-1-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)N(C=1C=NC=CC=1)CC1CN(CCC1)C(C)=O CMGJENIKHHAEFV-UHFFFAOYSA-N 0.000 claims 1
- IFFYUBMXSZENLM-UHFFFAOYSA-N 1-[3-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]azetidin-1-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C1CN(C1)C(C)=O)C=1C=NC=CC=1 IFFYUBMXSZENLM-UHFFFAOYSA-N 0.000 claims 1
- KTQAQBLERVVYCO-UHFFFAOYSA-N 1-[4-[2-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-2-pyridin-3-ylethyl]piperidin-1-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(CC1CCN(CC1)C(C)=O)C=1C=NC=CC=1 KTQAQBLERVVYCO-UHFFFAOYSA-N 0.000 claims 1
- GSFNQJFNMUHXEK-UHFFFAOYSA-N 1-[4-[3-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]methyl]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC=1C=NC=CC=1N1CCN(CC1)C(C)=O GSFNQJFNMUHXEK-UHFFFAOYSA-N 0.000 claims 1
- HGVKRSMRAJQTMC-UHFFFAOYSA-N 1-[4-[[8-(1-benzylindol-5-yl)quinoxalin-6-yl]amino]piperidin-1-yl]ethanone Chemical compound C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C=1C=C(C=C2N=CC=NC=12)NC1CCN(CC1)C(C)=O HGVKRSMRAJQTMC-UHFFFAOYSA-N 0.000 claims 1
- VCAXJSIOLNULLB-UHFFFAOYSA-N 1-[4-[[8-(1-benzylindol-6-yl)quinoxalin-6-yl]amino]piperidin-1-yl]ethanone Chemical compound C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CCN(CC1)C(C)=O VCAXJSIOLNULLB-UHFFFAOYSA-N 0.000 claims 1
- MRNMNQPXVAUKOS-UHFFFAOYSA-N 1-[4-[[8-(1-ethylindol-5-yl)quinoxalin-6-yl]amino]piperidin-1-yl]ethanone Chemical compound C(C)N1C=CC2=CC(=CC=C12)C=1C=C(C=C2N=CC=NC=12)NC1CCN(CC1)C(C)=O MRNMNQPXVAUKOS-UHFFFAOYSA-N 0.000 claims 1
- ZIFYOVOIUPKKSJ-UHFFFAOYSA-N 1-[4-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-3,4-dihydro-2H-quinolin-1-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CCN(C2=CC=CC=C12)C(C)=O ZIFYOVOIUPKKSJ-UHFFFAOYSA-N 0.000 claims 1
- IFMCUHGOEVWJIW-UHFFFAOYSA-N 1-[4-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]azepan-1-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CCN(CCC1)C(C)=O IFMCUHGOEVWJIW-UHFFFAOYSA-N 0.000 claims 1
- CJNAJRMTRBEVPL-UHFFFAOYSA-N 1-[4-[[8-(1-propan-2-ylindol-6-yl)quinoxalin-6-yl]amino]piperidin-1-yl]ethanone Chemical compound CC(C)N1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CCN(CC1)C(C)=O CJNAJRMTRBEVPL-UHFFFAOYSA-N 0.000 claims 1
- BFGGSURJCUHBGH-UHFFFAOYSA-N 1-[4-[[8-(1H-indol-6-yl)quinoxalin-6-yl]amino]piperidin-1-yl]ethanone Chemical compound N1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CCN(CC1)C(C)=O BFGGSURJCUHBGH-UHFFFAOYSA-N 0.000 claims 1
- CBBBRQAVATUXCZ-UHFFFAOYSA-N 1-[4-[[8-(2-methoxypyridin-4-yl)quinoxalin-6-yl]amino]piperidin-1-yl]ethanone Chemical compound COC1=NC=CC(=C1)C=1C=C(C=C2N=CC=NC=12)NC1CCN(CC1)C(C)=O CBBBRQAVATUXCZ-UHFFFAOYSA-N 0.000 claims 1
- FNWOCRSFHQUDOY-UHFFFAOYSA-N 1-[4-[[8-(2-methylindazol-5-yl)quinoxalin-6-yl]amino]piperidin-1-yl]ethanone Chemical compound CN1N=C2C=CC(=CC2=C1)C=1C=C(C=C2N=CC=NC=12)NC1CCN(CC1)C(C)=O FNWOCRSFHQUDOY-UHFFFAOYSA-N 0.000 claims 1
- JRONZJXJSRPZBJ-UHFFFAOYSA-N 1-[4-[[8-(3-methylbenzimidazol-5-yl)quinoxalin-6-yl]amino]piperidin-1-yl]ethanone Chemical compound CN1C=NC2=C1C=C(C=C2)C=1C=C(C=C2N=CC=NC=12)NC1CCN(CC1)C(C)=O JRONZJXJSRPZBJ-UHFFFAOYSA-N 0.000 claims 1
- KVLAVRIDLITVOP-UHFFFAOYSA-N 1-[4-[[8-[3-(dimethylamino)phenyl]quinoxalin-6-yl]amino]piperidin-1-yl]ethanone Chemical compound CN(C=1C=C(C=CC=1)C=1C=C(C=C2N=CC=NC=12)NC1CCN(CC1)C(C)=O)C KVLAVRIDLITVOP-UHFFFAOYSA-N 0.000 claims 1
- MQPSKWIZDVDMQO-UHFFFAOYSA-N 1-[4-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-(4-methylpyridin-3-yl)methyl]piperidin-1-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C1CCN(CC1)C(C)=O)C=1C=NC=CC=1C MQPSKWIZDVDMQO-UHFFFAOYSA-N 0.000 claims 1
- DMKDCHYWUQSHQL-UHFFFAOYSA-N 1-[4-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]piperidin-1-yl]ethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C1CCN(CC1)C(C)=O)C=1C=NC=CC=1 DMKDCHYWUQSHQL-UHFFFAOYSA-N 0.000 claims 1
- HLDRKUJTSDFPEK-UHFFFAOYSA-N 1-[4-[[[8-(2-amino-1,3-benzothiazol-5-yl)quinoxalin-6-yl]amino]-(6-methoxypyridin-3-yl)methyl]piperidin-1-yl]ethanone Chemical compound NC=1SC2=C(N=1)C=C(C=C2)C=1C=C(C=C2N=CC=NC=12)NC(C1CCN(CC1)C(C)=O)C=1C=NC(=CC=1)OC HLDRKUJTSDFPEK-UHFFFAOYSA-N 0.000 claims 1
- HIVZUWNBNOTGHZ-UHFFFAOYSA-N 1-[4-[[[8-(2-amino-1,3-benzothiazol-5-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]piperidin-1-yl]ethanone Chemical compound NC=1SC2=C(N=1)C=C(C=C2)C=1C=C(C=C2N=CC=NC=12)NC(C1CCN(CC1)C(C)=O)C=1C=NC=CC=1 HIVZUWNBNOTGHZ-UHFFFAOYSA-N 0.000 claims 1
- RWQRCGYDKUCYLM-UHFFFAOYSA-N 1-[4-[[[8-(3-methyl-1-benzofuran-5-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]piperidin-1-yl]ethanone Chemical compound CC1=COC2=C1C=C(C=C2)C=1C=C(C=C2N=CC=NC=12)NC(C1CCN(CC1)C(C)=O)C=1C=NC=CC=1 RWQRCGYDKUCYLM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- RKZUMWNCBGMTSO-UHFFFAOYSA-N 1-[5-[7-[(1-acetylpiperidin-4-yl)amino]quinoxalin-5-yl]pyridin-2-yl]ethanone Chemical compound C(C)(=O)N1CCC(CC1)NC1=CC(=C2N=CC=NC2=C1)C=1C=CC(=NC=1)C(C)=O RKZUMWNCBGMTSO-UHFFFAOYSA-N 0.000 claims 1
- XHWOCCQJMWNVQG-UHFFFAOYSA-N 1-[6-[7-(1-pyridin-3-ylethylamino)quinoxalin-5-yl]-2,3-dihydroindol-1-yl]ethanone Chemical compound N1=CC(=CC=C1)C(C)NC1=CC(=C2N=CC=NC2=C1)C1=CC=C2CCN(C2=C1)C(C)=O XHWOCCQJMWNVQG-UHFFFAOYSA-N 0.000 claims 1
- QMNYJYAEONAMIB-UHFFFAOYSA-N 1-methyl-2H-indol-6-one Chemical compound CN1CC=C2C=CC(C=C12)=O QMNYJYAEONAMIB-UHFFFAOYSA-N 0.000 claims 1
- YCIKNOKIRUIRJP-UHFFFAOYSA-N 1-methyl-5-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]pyridin-2-one Chemical compound CN1C(C=CC(=C1)C(C=1C=NC=CC=1)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)=O YCIKNOKIRUIRJP-UHFFFAOYSA-N 0.000 claims 1
- RETKVDIMXPDMHY-OAQYLSRUSA-N 1-methyl-6-[7-[[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]amino]quinoxalin-5-yl]pyrrolo[2,3-c]pyridin-7-one Chemical compound CN1C=CC2=C1C(N(C=C2)C1=C2N=CC=NC2=CC(=C1)N[C@@H]1CCCC2=CC=CC=C12)=O RETKVDIMXPDMHY-OAQYLSRUSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- 125000003287 1H-imidazol-4-ylmethyl group Chemical group [H]N1C([H])=NC(C([H])([H])[*])=C1[H] 0.000 claims 1
- DQRUGTNUWAROJZ-UHFFFAOYSA-N 2-[4-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]piperidin-1-yl]acetonitrile Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C1CCN(CC1)CC#N)C=1C=NC=CC=1 DQRUGTNUWAROJZ-UHFFFAOYSA-N 0.000 claims 1
- DNTNKERXWOVYMN-UHFFFAOYSA-N 2-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-1-pyrrolidin-1-ylpropan-1-one Chemical compound CC(NC1=CC(C2=CC=C3C=CN(C)C3=C2)=C2N=CC=NC2=C1)C(=O)N1CCCC1 DNTNKERXWOVYMN-UHFFFAOYSA-N 0.000 claims 1
- MRBULURLVLMODP-KRWDZBQOSA-N 2-amino-1-[(3S)-3-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound NCC(=O)N1C[C@H](CC1)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C MRBULURLVLMODP-KRWDZBQOSA-N 0.000 claims 1
- OORVVDRTOLMZEA-UHFFFAOYSA-N 2-amino-1-[4-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]piperidin-1-yl]propan-1-one Chemical compound NC(C(=O)N1CCC(CC1)C(C=1C=NC=CC=1)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C OORVVDRTOLMZEA-UHFFFAOYSA-N 0.000 claims 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- ZKFBCMGRWXHYBF-UHFFFAOYSA-N 2-methoxy-1-[4-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]piperidin-1-yl]ethanone Chemical compound COCC(=O)N1CCC(CC1)C(C=1C=NC=CC=1)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C ZKFBCMGRWXHYBF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- MHRQIZHNWYYNFA-UHFFFAOYSA-N 2-pyrrolidin-1-yl-1h-pyrimidin-6-one Chemical compound N1C(=O)C=CN=C1N1CCCC1 MHRQIZHNWYYNFA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- HULROZAADIQMAN-UHFFFAOYSA-N 3-[[[8-(1-methylindol-5-yl)quinoxalin-6-yl]amino]methyl]benzonitrile Chemical compound CN1C=CC2=CC(=CC=C12)C=1C=C(C=C2N=CC=NC=12)NCC=1C=C(C#N)C=CC=1 HULROZAADIQMAN-UHFFFAOYSA-N 0.000 claims 1
- ZZVJXRIEJHWZEG-UHFFFAOYSA-N 3-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]methyl]pyridine-4-carbonitrile Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC=1C=NC=CC=1C#N ZZVJXRIEJHWZEG-UHFFFAOYSA-N 0.000 claims 1
- AIGZKTAURBDPHM-UHFFFAOYSA-N 3-amino-1-[4-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]piperidin-1-yl]propan-1-one Chemical compound NCCC(=O)N1CCC(CC1)C(C=1C=NC=CC=1)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C AIGZKTAURBDPHM-UHFFFAOYSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- ONVKPGQOWYBOMP-UHFFFAOYSA-N 3-methyl-8-(1-methylindol-6-yl)-N-(1-pyridin-3-ylethyl)quinoxalin-6-amine Chemical compound CC=1C=NC2=C(C=C(C=C2N=1)NC(C)C=1C=NC=CC=1)C1=CC=C2C=CN(C2=C1)C ONVKPGQOWYBOMP-UHFFFAOYSA-N 0.000 claims 1
- PJRRINVCOFJENP-UHFFFAOYSA-N 4-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]cyclohexan-1-one Chemical compound CN1C=CC2=CC=C(C=C12)C1=C2N=CC=NC2=CC(NC2CCC(=O)CC2)=C1 PJRRINVCOFJENP-UHFFFAOYSA-N 0.000 claims 1
- LKNXVNLLVIBBDM-UHFFFAOYSA-N 4-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]piperidin-2-one Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CC(NCC1)=O LKNXVNLLVIBBDM-UHFFFAOYSA-N 0.000 claims 1
- RXTBJROSMFVKCD-UHFFFAOYSA-N 4-[[[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(C1=CC(NC=C1)=O)C=1C=NC=CC=1 RXTBJROSMFVKCD-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- XQAGIMUCEBYZHM-UHFFFAOYSA-N 5-(1-methylindol-6-yl)-7-(1-pyridin-3-ylethylamino)-1H-quinoxalin-2-one Chemical compound CN1C=CC2=CC=C(C=C12)C1=C2N=CC(=NC2=CC(=C1)NC(C)C=1C=NC=CC=1)O XQAGIMUCEBYZHM-UHFFFAOYSA-N 0.000 claims 1
- KKNAMLZHKMHGKV-UHFFFAOYSA-N 5-(1-methylindol-6-yl)-7-(pyridin-3-ylmethoxy)quinoxaline Chemical compound CN1C=CC2=CC=C(C=C12)C1=C2N=CC=NC2=CC(OCC2=CC=CN=C2)=C1 KKNAMLZHKMHGKV-UHFFFAOYSA-N 0.000 claims 1
- HDDKARVKSRALIK-UHFFFAOYSA-N 5-[7-(1-pyridin-3-ylethylamino)quinoxalin-5-yl]-2,3-dihydroisoindol-1-one Chemical compound N1=CC(=CC=C1)C(C)NC1=CC(=C2N=CC=NC2=C1)C=1C=C2CNC(C2=CC=1)=O HDDKARVKSRALIK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KZLGBUQJVQNTIN-UHFFFAOYSA-N 5-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]piperidin-2-one Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CCC(NC1)=O KZLGBUQJVQNTIN-UHFFFAOYSA-N 0.000 claims 1
- SLAMEEVSYJHYEW-UHFFFAOYSA-N 5-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]methyl]-1H-pyridin-2-one Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC=1C=CC(=NC=1)O SLAMEEVSYJHYEW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CYUINNFZLXKMDH-UHFFFAOYSA-N 6-[(1-acetylpyrrolidin-3-yl)amino]-8-(1-methylindol-6-yl)quinoxaline-2-carbonitrile Chemical compound C(C)(=O)N1CC(CC1)NC=1C=C2N=CC(=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C#N CYUINNFZLXKMDH-UHFFFAOYSA-N 0.000 claims 1
- QHAJOLQECFLUHE-UHFFFAOYSA-N 6-[7-(1-pyridin-3-ylethylamino)quinoxalin-5-yl]chromen-4-one Chemical compound N1=CC(=CC=C1)C(C)NC1=CC(=C2N=CC=NC2=C1)C=1C=C2C(C=COC2=CC=1)=O QHAJOLQECFLUHE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- JCNHTPJHEUOIHK-UHFFFAOYSA-N 7-chloro-5-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]quinoxaline Chemical compound ClC1=CC(=C2N=CC=NC2=C1)C1=C(C=C(C(=C1)S(=O)CC(F)(F)F)C)F JCNHTPJHEUOIHK-UHFFFAOYSA-N 0.000 claims 1
- GVHRDWAAVVIPOZ-OAQYLSRUSA-N 8-(1,3-dimethylpyrazol-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]quinoxalin-6-amine Chemical compound CN1N=C(C(=C1)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CCCC2=CC=CC=C12)C GVHRDWAAVVIPOZ-OAQYLSRUSA-N 0.000 claims 1
- GISCZGQKCQXXOT-UHFFFAOYSA-N 8-(1-methylindol-4-yl)-N-(1-pyridin-3-ylethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=C(C=CC=C12)C=1C=C(C=C2N=CC=NC=12)NC(C)C=1C=NC=CC=1 GISCZGQKCQXXOT-UHFFFAOYSA-N 0.000 claims 1
- YETAPCSHFKKDSJ-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-6-(1-pyridin-3-ylethylamino)-1H-quinoxalin-2-one Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC(=NC=12)O)NC(C)C=1C=NC=CC=1 YETAPCSHFKKDSJ-UHFFFAOYSA-N 0.000 claims 1
- HEEBRASXFNXLKE-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(1,2-oxazol-4-ylmethyl)quinoxalin-6-amine Chemical compound O1N=CC(=C1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C HEEBRASXFNXLKE-UHFFFAOYSA-N 0.000 claims 1
- XBULJVMDJONCLN-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(1,2-thiazol-5-ylmethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1=CC=NS1 XBULJVMDJONCLN-UHFFFAOYSA-N 0.000 claims 1
- ATSMQQHHSSMDHL-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(1,3-thiazol-4-ylmethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC=1N=CSC=1 ATSMQQHHSSMDHL-UHFFFAOYSA-N 0.000 claims 1
- LLSCKDBHKNMUKJ-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(1,3-thiazol-5-ylmethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1=CN=CS1 LLSCKDBHKNMUKJ-UHFFFAOYSA-N 0.000 claims 1
- VCMJLBASQKURAX-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(1-methylsulfonylpyrrolidin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)N1CC(CC1)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C VCMJLBASQKURAX-UHFFFAOYSA-N 0.000 claims 1
- FAXGAUYTOBIMML-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(1-phenylpyrrolidin-3-yl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CN(CC1)C1=CC=CC=C1 FAXGAUYTOBIMML-UHFFFAOYSA-N 0.000 claims 1
- NEZAOVGAVDAYQC-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(1-pyrazin-2-ylethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C)C1=NC=CN=C1 NEZAOVGAVDAYQC-UHFFFAOYSA-N 0.000 claims 1
- RNBQOPNMUZRPPS-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(1-pyridin-3-ylpyrrolidin-3-yl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CN(CC1)C=1C=NC=CC=1 RNBQOPNMUZRPPS-UHFFFAOYSA-N 0.000 claims 1
- XIAGLCIWPFZUTJ-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(1-pyrimidin-2-ylpiperidin-4-yl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1CCN(CC1)C1=NC=CC=N1 XIAGLCIWPFZUTJ-UHFFFAOYSA-N 0.000 claims 1
- NGOSFRZQTIJUKL-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(1H-1,2,4-triazol-5-ylmethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1=NN=CN1 NGOSFRZQTIJUKL-UHFFFAOYSA-N 0.000 claims 1
- RBJMDCATORMDAV-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(1H-pyrazol-4-ylmethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC=1C=NNC=1 RBJMDCATORMDAV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QWQWPDNKQJBQDR-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(3-methyltriazol-4-yl)-N-(pyridin-3-ylmethyl)quinoxalin-6-amine Chemical compound CN1N=NC=C1N(C=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)CC=1C=NC=CC=1 QWQWPDNKQJBQDR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YRSGBJDMUAYQSC-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(5,6,7,8-tetrahydroquinolin-5-yl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC1C=2C=CC=NC=2CCC1 YRSGBJDMUAYQSC-UHFFFAOYSA-N 0.000 claims 1
- XSZWTHKUDCJSHP-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(5-methylsulfonylpyridin-3-yl)-N-(pyridin-3-ylmethyl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C=1C=C(C=NC=1)N(C=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)CC=1C=NC=CC=1 XSZWTHKUDCJSHP-UHFFFAOYSA-N 0.000 claims 1
- HPYNWVRWFFLSAI-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(morpholin-2-ylmethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1CNCCO1 HPYNWVRWFFLSAI-UHFFFAOYSA-N 0.000 claims 1
- DEMRFSVCZBJTGR-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(morpholin-3-ylmethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1NCCOC1 DEMRFSVCZBJTGR-UHFFFAOYSA-N 0.000 claims 1
- VXQUDLSNIQUJJE-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(oxan-3-ylmethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1COCCC1 VXQUDLSNIQUJJE-UHFFFAOYSA-N 0.000 claims 1
- UICWSWIYRWOCDM-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(piperidin-2-ylmethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C1=C2N=CC=NC2=CC(NCC2CCCCN2)=C1 UICWSWIYRWOCDM-UHFFFAOYSA-N 0.000 claims 1
- YQHRLIDJOJMGJY-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(piperidin-3-ylmethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1CNCCC1 YQHRLIDJOJMGJY-UHFFFAOYSA-N 0.000 claims 1
- JQAOOMMQXIRZFI-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(pyridazin-3-ylmethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC=1N=NC=CC=1 JQAOOMMQXIRZFI-UHFFFAOYSA-N 0.000 claims 1
- HJRBLQXPOMOPDE-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(pyridazin-4-ylmethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1=CN=NC=C1 HJRBLQXPOMOPDE-UHFFFAOYSA-N 0.000 claims 1
- WKGBUGZFTZIXHP-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-(pyridin-3-ylmethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC=1C=NC=CC=1 WKGBUGZFTZIXHP-UHFFFAOYSA-N 0.000 claims 1
- BEWWEVJARFZVRE-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(1-methylpiperidin-2-yl)methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1N(CCCC1)C BEWWEVJARFZVRE-UHFFFAOYSA-N 0.000 claims 1
- XLPFTOUVZOYIHM-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(1-methylpiperidin-4-yl)-pyridin-3-ylmethyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C=1C=NC=CC=1)C1CCN(CC1)C XLPFTOUVZOYIHM-UHFFFAOYSA-N 0.000 claims 1
- VMDWGJMLUZDNPS-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(1-methylpyrazol-4-yl)methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC=1C=NN(C=1)C VMDWGJMLUZDNPS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- LPLAHTIXWYCFLA-INIZCTEOSA-N 8-(1-methylindol-6-yl)-N-[(1S)-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-INIZCTEOSA-N 0.000 claims 1
- IHKUJFFJLUZEKY-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(2-methyl-1,3-oxazol-5-yl)methyl]quinoxalin-6-amine Chemical compound CC=1OC(=CN=1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C IHKUJFFJLUZEKY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NIJICOOGHZBPAT-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(2-methylsulfonylphenyl)methyl]quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=CC=C1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C NIJICOOGHZBPAT-UHFFFAOYSA-N 0.000 claims 1
- YDQPTWRYAXCBTF-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(3-methyl-1,2-thiazol-5-yl)methyl]quinoxalin-6-amine Chemical compound CC1=NSC(=C1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C YDQPTWRYAXCBTF-UHFFFAOYSA-N 0.000 claims 1
- XNNODUVIAHSAOJ-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(3-methylsulfonylphenyl)methyl]quinoxalin-6-amine Chemical compound CS(=O)(=O)C=1C=C(CNC=2C=C3N=CC=NC3=C(C=2)C2=CC=C3C=CN(C3=C2)C)C=CC=1 XNNODUVIAHSAOJ-UHFFFAOYSA-N 0.000 claims 1
- REYQUODTLKIAMI-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(3-methyltriazol-4-yl)-pyridin-3-ylmethyl]quinoxalin-6-amine Chemical compound CN1N=NC=C1C(NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C=1C=NC=CC=1 REYQUODTLKIAMI-UHFFFAOYSA-N 0.000 claims 1
- XLXYZHVZLPGZQY-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(3-methyltriazol-4-yl)methyl]quinoxalin-6-amine Chemical compound CN1N=NC=C1CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C XLXYZHVZLPGZQY-UHFFFAOYSA-N 0.000 claims 1
- FLISBEPXWRRPNU-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(3-nitrophenyl)methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1=CC(=CC=C1)[N+](=O)[O-] FLISBEPXWRRPNU-UHFFFAOYSA-N 0.000 claims 1
- MVHFCJFIFJKBNW-FQEVSTJZSA-N 8-(1-methylindol-6-yl)-N-[(3S)-1-(2-methylpyrimidin-4-yl)pyrrolidin-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)C MVHFCJFIFJKBNW-FQEVSTJZSA-N 0.000 claims 1
- HIZOLCJPWBCUMD-NRFANRHFSA-N 8-(1-methylindol-6-yl)-N-[(3S)-1-(3-methylpyridin-2-yl)pyrrolidin-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=CC=C1C HIZOLCJPWBCUMD-NRFANRHFSA-N 0.000 claims 1
- MRASFIFKLIERJN-IBGZPJMESA-N 8-(1-methylindol-6-yl)-N-[(3S)-1-pyrazin-2-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=CN=C1 MRASFIFKLIERJN-IBGZPJMESA-N 0.000 claims 1
- ISBGUTKSGBWKNG-FQEVSTJZSA-N 8-(1-methylindol-6-yl)-N-[(3S)-1-pyridin-2-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=CC=C1 ISBGUTKSGBWKNG-FQEVSTJZSA-N 0.000 claims 1
- IGOWKQYORMHRBN-IBGZPJMESA-N 8-(1-methylindol-6-yl)-N-[(3S)-1-pyrimidin-2-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=CC=N1 IGOWKQYORMHRBN-IBGZPJMESA-N 0.000 claims 1
- NDJJPPZBDGTCCD-IBGZPJMESA-N 8-(1-methylindol-6-yl)-N-[(3S)-1-pyrimidin-5-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)C=1C=NC=NC=1 NDJJPPZBDGTCCD-IBGZPJMESA-N 0.000 claims 1
- RNEYHUYURVSUFV-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(4-methyl-1,2,4-triazol-3-yl)methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1=NN=CN1C RNEYHUYURVSUFV-UHFFFAOYSA-N 0.000 claims 1
- NOPCCXKZKGCTNQ-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(4-methylmorpholin-2-yl)methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1CN(CCO1)C NOPCCXKZKGCTNQ-UHFFFAOYSA-N 0.000 claims 1
- DTGMRWOBUUNOFJ-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(4-methylpyridin-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 DTGMRWOBUUNOFJ-UHFFFAOYSA-N 0.000 claims 1
- DWHJDKHFNGTHHF-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(4-methylsulfonylphenyl)methyl]quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=CC=C(C=C1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C DWHJDKHFNGTHHF-UHFFFAOYSA-N 0.000 claims 1
- XHUAZSCCZHQWDW-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(4-nitrophenyl)methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1=CC=C(C=C1)[N+](=O)[O-] XHUAZSCCZHQWDW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- AZRYGNXMLBOFPU-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(4-pyrimidin-5-ylpyridin-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=NC=NC=1 AZRYGNXMLBOFPU-UHFFFAOYSA-N 0.000 claims 1
- JRGQOELMKRKLEM-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC=1OC(=NN=1)C JRGQOELMKRKLEM-UHFFFAOYSA-N 0.000 claims 1
- KJBYVWQUVQHQQR-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(5-morpholin-4-ylpyridin-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=C(C=1)N1CCOCC1 KJBYVWQUVQHQQR-UHFFFAOYSA-N 0.000 claims 1
- UMNCRIMBDHNYBZ-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[(5-pyrimidin-5-ylpyridin-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=C(C=1)C=1C=NC=NC=1 UMNCRIMBDHNYBZ-UHFFFAOYSA-N 0.000 claims 1
- ZUVHBLLISPQAFW-HSZRJFAPSA-N 8-(1-methylindol-6-yl)-N-[(8R)-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)N[C@@H]1CCCC=2C=CN=CC1=2 ZUVHBLLISPQAFW-HSZRJFAPSA-N 0.000 claims 1
- ZUVHBLLISPQAFW-QHCPKHFHSA-N 8-(1-methylindol-6-yl)-N-[(8S)-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)N[C@H]1CCCC=2C=CN=CC1=2 ZUVHBLLISPQAFW-QHCPKHFHSA-N 0.000 claims 1
- BOGCUVRORYUXOE-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[1-[4-(1-methylpyrazol-4-yl)pyridin-3-yl]ethyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C)C=1C=NC=CC=1C=1C=NN(C=1)C BOGCUVRORYUXOE-UHFFFAOYSA-N 0.000 claims 1
- KFWAIJBNSPVRBN-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[1-[4-(4-methylpiperazin-1-yl)pyridin-3-yl]ethyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C)C=1C=NC=CC=1N1CCN(CC1)C KFWAIJBNSPVRBN-UHFFFAOYSA-N 0.000 claims 1
- UBBBVNMHZNZEBO-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[2-(1-methylpyrrolidin-3-yl)-1-pyridin-3-ylethyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(CC1CN(CC1)C)C=1C=NC=CC=1 UBBBVNMHZNZEBO-UHFFFAOYSA-N 0.000 claims 1
- NHENREWNMHRWFE-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[[2-(1-methylpyrazol-4-yl)pyridin-4-yl]methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1=CC(=NC=C1)C=1C=NN(C=1)C NHENREWNMHRWFE-UHFFFAOYSA-N 0.000 claims 1
- FBPLZGIOUOGFMO-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[[4-(1-methylpyrazol-4-yl)pyridin-2-yl]methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1=NC=CC(=C1)C=1C=NN(C=1)C FBPLZGIOUOGFMO-UHFFFAOYSA-N 0.000 claims 1
- QDBLHEZEMQSZQH-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[[5-(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=C(C=1)C=1C=NN(C=1)C QDBLHEZEMQSZQH-UHFFFAOYSA-N 0.000 claims 1
- VNBBQGFMORPCTB-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[[5-(1H-pyrazol-5-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=C(C=1)C1=CC=NN1 VNBBQGFMORPCTB-UHFFFAOYSA-N 0.000 claims 1
- LSYIHGMYRVQUQS-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[piperidin-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)NC(C=1C=NC=CC=1)C1CCNCC1 LSYIHGMYRVQUQS-UHFFFAOYSA-N 0.000 claims 1
- ZPLVIMRKOQYFRO-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[pyridin-3-yl(pyridin-4-yl)methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C1=CC=NC=C1)C=1C=NC=CC=1 ZPLVIMRKOQYFRO-UHFFFAOYSA-N 0.000 claims 1
- IHUYKNWTAGZBHE-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-[pyridin-3-yl(pyrimidin-5-yl)methyl]quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C=1C=NC=NC=1)C=1C=NC=CC=1 IHUYKNWTAGZBHE-UHFFFAOYSA-N 0.000 claims 1
- ATCBQYZPAVHBJH-UHFFFAOYSA-N 8-(1-methylindol-6-yl)-N-piperidin-3-ylquinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C1=C2N=CC=NC2=CC(NC2CCCNC2)=C1 ATCBQYZPAVHBJH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- RXOUSLPYLVPQBS-UHFFFAOYSA-N 8-(1-methylindol-6-yl)quinoxalin-6-ol Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)O RXOUSLPYLVPQBS-UHFFFAOYSA-N 0.000 claims 1
- KZPZHYDIZVGGGP-UHFFFAOYSA-N 8-(1-methylpyrrolo[2,3-b]pyridin-6-yl)-N-(1-pyridin-3-ylethyl)quinoxalin-6-amine Chemical compound CN1C=CC=2C1=NC(=CC=2)C=1C=C(C=C2N=CC=NC=12)NC(C)C=1C=NC=CC=1 KZPZHYDIZVGGGP-UHFFFAOYSA-N 0.000 claims 1
- RZHGOTVPKRNLIR-UHFFFAOYSA-N 8-(1-methylpyrrolo[3,2-b]pyridin-6-yl)-N-(1-pyridin-3-ylethyl)quinoxalin-6-amine Chemical compound CN1C=CC2=NC=C(C=C21)C=1C=C(C=C2N=CC=NC=12)NC(C)C=1C=NC=CC=1 RZHGOTVPKRNLIR-UHFFFAOYSA-N 0.000 claims 1
- IJZMFXUOFNFLBN-UHFFFAOYSA-N 8-(1H-indol-6-yl)-N-(1-pyridin-3-ylethyl)quinoxalin-6-amine Chemical compound CC(NC1=CC(C2=CC=C3C=CNC3=C2)=C2N=CC=NC2=C1)C1=CC=CN=C1 IJZMFXUOFNFLBN-UHFFFAOYSA-N 0.000 claims 1
- XYOPWGZLYDAKPA-JOCHJYFZSA-N 8-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]quinoxalin-6-amine Chemical compound O1CCOC2=C1C=CC(=C2)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CCCC2=CC=CC=C12 XYOPWGZLYDAKPA-JOCHJYFZSA-N 0.000 claims 1
- AWJYYHRGZCZFFR-UHFFFAOYSA-N 8-(3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-N-(1-pyridin-3-ylethyl)quinoxalin-6-amine Chemical compound C1N(CC2C1CCC2)C=1C=C(C=C2N=CC=NC=12)NC(C)C=1C=NC=CC=1 AWJYYHRGZCZFFR-UHFFFAOYSA-N 0.000 claims 1
- IGGAHQHZTCBGJE-JOCHJYFZSA-N 8-(3-amino-4-methoxyphenyl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]quinoxalin-6-amine Chemical compound NC=1C=C(C=CC=1OC)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CCCC2=CC=CC=C12 IGGAHQHZTCBGJE-JOCHJYFZSA-N 0.000 claims 1
- YWSMQJHBVIOTQC-UHFFFAOYSA-N 8-(3-methyl-1-benzofuran-5-yl)-N-(morpholin-2-ylmethyl)quinoxalin-6-amine Chemical compound CC1=COC2=C1C=C(C=C2)C=1C=C(C=C2N=CC=NC=12)NCC1CNCCO1 YWSMQJHBVIOTQC-UHFFFAOYSA-N 0.000 claims 1
- RDHZAZYVVZLMIJ-UHFFFAOYSA-N 8-(3-methyl-1-benzofuran-5-yl)-N-[1-[5-(1-methylpyrazol-4-yl)pyridin-3-yl]ethyl]quinoxalin-6-amine Chemical compound CC1=COC2=C1C=C(C=C2)C=1C=C(C=C2N=CC=NC=12)NC(C)C=1C=NC=C(C=1)C=1C=NN(C=1)C RDHZAZYVVZLMIJ-UHFFFAOYSA-N 0.000 claims 1
- QRFKZFKTKDQUDG-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-[(3-methylimidazol-4-yl)-pyridin-3-ylmethyl]quinoxalin-6-amine Chemical compound CC1=CSC2=C1C=C(C=C2)C=1C=C(C=C2N=CC=NC=12)NC(C=1C=NC=CC=1)C1=CN=CN1C QRFKZFKTKDQUDG-UHFFFAOYSA-N 0.000 claims 1
- RCKUKDQYZCHOHU-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-[piperidin-4-yl(pyridin-3-yl)methyl]quinoxalin-6-amine Chemical compound CC1=CSC2=C1C=C(C=C2)C=1C=C(C=C2N=CC=NC=12)NC(C=1C=NC=CC=1)C1CCNCC1 RCKUKDQYZCHOHU-UHFFFAOYSA-N 0.000 claims 1
- BFMATETWHJQXTO-SFHVURJKSA-N 8-(3-methyl-1H-indol-5-yl)-N-[(3S)-1-pyrimidin-4-ylpyrrolidin-3-yl]quinoxalin-6-amine Chemical compound CC1=CNC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CN(CC1)C1=NC=NC=C1 BFMATETWHJQXTO-SFHVURJKSA-N 0.000 claims 1
- GSGFQQXUEZBIOU-JOCHJYFZSA-N 8-(3-methylbenzimidazol-5-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]quinoxalin-6-amine Chemical compound CN1C=NC2=C1C=C(C=C2)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CCCC2=CC=CC=C12 GSGFQQXUEZBIOU-JOCHJYFZSA-N 0.000 claims 1
- WWIPLSQRHWUPSK-JOCHJYFZSA-N 8-(4-amino-3-methoxyphenyl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]quinoxalin-6-amine Chemical compound NC1=C(C=C(C=C1)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CCCC2=CC=CC=C12)OC WWIPLSQRHWUPSK-JOCHJYFZSA-N 0.000 claims 1
- JTEUYCRBVGRHHP-OAQYLSRUSA-N 8-(4-methoxy-3-nitrophenyl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]quinoxalin-6-amine Chemical compound COC1=C(C=C(C=C1)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CCCC2=CC=CC=C12)[N+](=O)[O-] JTEUYCRBVGRHHP-OAQYLSRUSA-N 0.000 claims 1
- 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 1
- IBBBPGPHCKQBOC-UHFFFAOYSA-N 8-[1-(2-methoxyethyl)indol-6-yl]-N-(1-pyridin-3-ylethyl)quinoxalin-6-amine Chemical compound COCCN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C)C=1C=NC=CC=1 IBBBPGPHCKQBOC-UHFFFAOYSA-N 0.000 claims 1
- ZAKJADAKAWOLBH-UHFFFAOYSA-N 8-[3-(3-aminoazetidin-1-yl)phenyl]-N-(1-pyridin-3-ylethyl)quinoxalin-6-amine Chemical compound NC1CN(C1)C=1C=C(C=CC=1)C=1C=C(C=C2N=CC=NC=12)NC(C)C=1C=NC=CC=1 ZAKJADAKAWOLBH-UHFFFAOYSA-N 0.000 claims 1
- UQBRCRNNPDTPGL-UHFFFAOYSA-N 8-chloro-N-(1-pyridin-3-ylethyl)quinoxalin-6-amine Chemical compound ClC=1C=C(C=C2N=CC=NC=12)NC(C)C=1C=NC=CC=1 UQBRCRNNPDTPGL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- FILAQLJTWQBXNV-MRXNPFEDSA-N 8-chloro-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]quinoxalin-6-amine Chemical compound ClC=1C=C(C=C2N=CC=NC=12)N[C@@H]1CCCC2=CC=CC=C12 FILAQLJTWQBXNV-MRXNPFEDSA-N 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 229910014033 C-OH Inorganic materials 0.000 claims 1
- IBDAZDDBWJQTPP-LMOVPXPDSA-N CN1N=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC12)N[C@@H]1CN(CC1)C(C)=O.CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC12)NC1CNCC1 Chemical compound CN1N=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC12)N[C@@H]1CN(CC1)C(C)=O.CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC12)NC1CNCC1 IBDAZDDBWJQTPP-LMOVPXPDSA-N 0.000 claims 1
- QYWOUVGWWAZUSD-UHFFFAOYSA-N COC1=CC=C(C=N1)C(C)NC=1C=C2N=CC=NC2=C(C1)C1=CC=C2C=CN(C2=C1)C.NC1=CC=C(C=C1)CNC=1C=C2N=CC=NC2=C(C1)C1=CC=C2C=CN(C2=C1)C Chemical compound COC1=CC=C(C=N1)C(C)NC=1C=C2N=CC=NC2=C(C1)C1=CC=C2C=CN(C2=C1)C.NC1=CC=C(C=C1)CNC=1C=C2N=CC=NC2=C(C1)C1=CC=C2C=CN(C2=C1)C QYWOUVGWWAZUSD-UHFFFAOYSA-N 0.000 claims 1
- HSIBNMCPGKQPHM-UHFFFAOYSA-N COC1=CC=C(C=N1)C(NC=1C=C2N=CC=NC2=C(C1)C1=CC=C2C=CN(C2=C1)C)C=1C=NC(=CC1)OC.NC1CCC(CC1)C(NC=1C=C2N=CC=NC2=C(C1)C1=CC=C2C=CN(C2=C1)C)C=1C=NC=CC1 Chemical compound COC1=CC=C(C=N1)C(NC=1C=C2N=CC=NC2=C(C1)C1=CC=C2C=CN(C2=C1)C)C=1C=NC(=CC1)OC.NC1CCC(CC1)C(NC=1C=C2N=CC=NC2=C(C1)C1=CC=C2C=CN(C2=C1)C)C=1C=NC=CC1 HSIBNMCPGKQPHM-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 229910014570 C—OH Inorganic materials 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 101000823463 Homo sapiens Fructose-2,6-bisphosphatase Proteins 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 claims 1
- AYZHGEDUAIGWHE-UHFFFAOYSA-N N-(2,2-dimethyloxan-4-yl)-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C1=C2N=CC=NC2=CC(NC2CCOC(C)(C)C2)=C1 AYZHGEDUAIGWHE-UHFFFAOYSA-N 0.000 claims 1
- YWZARPDYYWINLC-UHFFFAOYSA-N N-(7-azaspiro[3.5]nonan-3-yl)-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound C1(CCC11CCNCC1)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C YWZARPDYYWINLC-UHFFFAOYSA-N 0.000 claims 1
- BZIOHCLSRARDNV-UHFFFAOYSA-N N-(dipyridin-3-ylmethyl)-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound N1=CC(=CC=C1)C(NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C=1C=NC=CC=1 BZIOHCLSRARDNV-UHFFFAOYSA-N 0.000 claims 1
- TUGYGASPQZQCBL-UHFFFAOYSA-N N-(furan-2-ylmethyl)-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound O1C(=CC=C1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C TUGYGASPQZQCBL-UHFFFAOYSA-N 0.000 claims 1
- OZMXBMAEZGFAHE-UHFFFAOYSA-N N-[(1-methylimidazol-4-yl)-pyridin-3-ylmethyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound CN1C=NC(=C1)C(NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C=1C=NC=CC=1 OZMXBMAEZGFAHE-UHFFFAOYSA-N 0.000 claims 1
- QQVNGDRZTAYSLA-QGZVFWFLSA-N N-[(1R)-1-(3-methoxyphenyl)ethyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound COC=1C=C(C=CC=1)[C@@H](C)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C QQVNGDRZTAYSLA-QGZVFWFLSA-N 0.000 claims 1
- UXVZIAOQBKLUFG-UHFFFAOYSA-N N-[(2-aminopyrimidin-5-yl)methyl]-8-(1-methylindol-5-yl)quinoxalin-6-amine Chemical compound NC1=NC=C(C=N1)CNC=1C=C2N=CC=NC2=C(C=1)C=1C=C2C=CN(C2=CC=1)C UXVZIAOQBKLUFG-UHFFFAOYSA-N 0.000 claims 1
- ILQZKIZELYANSK-UHFFFAOYSA-N N-[(2-bromopyridin-4-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound BrC1=NC=CC(=C1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C ILQZKIZELYANSK-UHFFFAOYSA-N 0.000 claims 1
- NQBHQZGUNTUYQJ-UHFFFAOYSA-N N-[(2-chloropyrimidin-5-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound ClC1=NC=C(C=N1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C NQBHQZGUNTUYQJ-UHFFFAOYSA-N 0.000 claims 1
- YRMFUCVSCZNUBP-UHFFFAOYSA-N N-[(2-methoxypyridin-3-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound COC1=NC=CC=C1CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C YRMFUCVSCZNUBP-UHFFFAOYSA-N 0.000 claims 1
- KVODKETZRXYRFR-UHFFFAOYSA-N N-[(2-methoxypyridin-4-yl)-pyridin-3-ylmethyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound COC1=NC=CC(=C1)C(NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C=1C=NC=CC=1 KVODKETZRXYRFR-UHFFFAOYSA-N 0.000 claims 1
- WBTFBYASEKBAFK-UHFFFAOYSA-N N-[(3-aminophenyl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NCC1=CC(=CC=C1)N WBTFBYASEKBAFK-UHFFFAOYSA-N 0.000 claims 1
- LCRUFZUHJMXYKY-UHFFFAOYSA-N N-[(3-methylimidazol-4-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound CN1C=NC=C1CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C LCRUFZUHJMXYKY-UHFFFAOYSA-N 0.000 claims 1
- GGWDMVUOYBZDOU-FQEVSTJZSA-N N-[(3S)-1-(1H-benzimidazol-2-yl)pyrrolidin-3-yl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound N1C(=NC2=C1C=CC=C2)N1C[C@H](CC1)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C GGWDMVUOYBZDOU-FQEVSTJZSA-N 0.000 claims 1
- RHFVXPGUQIFDDE-UHFFFAOYSA-N N-[(4-aminopyridin-3-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound NC1=C(C=NC=C1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C RHFVXPGUQIFDDE-UHFFFAOYSA-N 0.000 claims 1
- OKCJKHJJTFYFNA-UHFFFAOYSA-N N-[(4-benzylmorpholin-3-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound C(C1=CC=CC=C1)N1C(COCC1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C OKCJKHJJTFYFNA-UHFFFAOYSA-N 0.000 claims 1
- MUOXUYBHSBJHGM-UHFFFAOYSA-N N-[(4-bromopyridin-2-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound BrC1=CC(=NC=C1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C MUOXUYBHSBJHGM-UHFFFAOYSA-N 0.000 claims 1
- ZVFFRRMGEBGLNM-UHFFFAOYSA-N N-[(4-fluoropyridin-3-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C1=C2N=CC=NC2=CC(NCC2=C(F)C=CN=C2)=C1 ZVFFRRMGEBGLNM-UHFFFAOYSA-N 0.000 claims 1
- MKIDHTKIYYHRHM-UHFFFAOYSA-N N-[(5-aminopyridin-3-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound NC=1C=C(C=NC=1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C MKIDHTKIYYHRHM-UHFFFAOYSA-N 0.000 claims 1
- SBPMAMVIRIABTD-UHFFFAOYSA-N N-[(5-bromopyridin-3-yl)methyl]-8-(1-methylindazol-6-yl)quinoxalin-6-amine Chemical compound BrC=1C=C(C=NC=1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=NN(C2=C1)C SBPMAMVIRIABTD-UHFFFAOYSA-N 0.000 claims 1
- JCDSLJPZTDBZCI-UHFFFAOYSA-N N-[(6-aminopyridin-3-yl)-pyridin-3-ylmethyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound NC1=CC=C(C=N1)C(NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C=1C=NC=CC=1 JCDSLJPZTDBZCI-UHFFFAOYSA-N 0.000 claims 1
- MTSRIZXTQTWECY-UHFFFAOYSA-N N-[(6-methoxypyridin-3-yl)-(1,2-thiazol-5-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound COC1=CC=C(C=N1)C(NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C1=CC=NS1 MTSRIZXTQTWECY-UHFFFAOYSA-N 0.000 claims 1
- QQWGNTITMUSOJO-UHFFFAOYSA-N N-[(6-methoxypyridin-3-yl)-(3-methylimidazol-4-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound COC1=CC=C(C=N1)C(NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C1=CN=CN1C QQWGNTITMUSOJO-UHFFFAOYSA-N 0.000 claims 1
- BIDLROYHTMGTHG-UHFFFAOYSA-N N-[(6-methoxypyridin-3-yl)-(3-methylimidazol-4-yl)methyl]-8-(3-methyl-1-benzothiophen-5-yl)quinoxalin-6-amine Chemical compound COC1=CC=C(C=N1)C(NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1)C1=CN=CN1C BIDLROYHTMGTHG-UHFFFAOYSA-N 0.000 claims 1
- MZUHOFZPDUAMNB-UHFFFAOYSA-N N-[(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(C=1N(N=NC=1)C)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C MZUHOFZPDUAMNB-UHFFFAOYSA-N 0.000 claims 1
- IVIMXANDLGGZIV-UHFFFAOYSA-N N-[(6-methoxypyridin-3-yl)-(3-methyltriazol-4-yl)methyl]-8-(3-methyl-1-benzofuran-5-yl)quinoxalin-6-amine Chemical compound COC1=CC=C(C=N1)C(NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CO2)C)C=1)C1=CN=NN1C IVIMXANDLGGZIV-UHFFFAOYSA-N 0.000 claims 1
- XBBUJUUODZDTIM-UHFFFAOYSA-N N-[(6-methoxypyridin-3-yl)-pyridin-3-ylmethyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound COC1=CC=C(C=N1)C(NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C=1C=NC=CC=1 XBBUJUUODZDTIM-UHFFFAOYSA-N 0.000 claims 1
- SMFHUIUVOAOIGI-UHFFFAOYSA-N N-[(6-methoxypyridin-3-yl)-pyridin-3-ylmethyl]-N-methyl-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound COC1=CC=C(C=N1)C(N(C=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C)C)C=1C=NC=CC=1 SMFHUIUVOAOIGI-UHFFFAOYSA-N 0.000 claims 1
- QFCWVDQHAVTYQZ-UHFFFAOYSA-N N-[(6-methoxypyridin-3-yl)methyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound COC1=CC=C(C=N1)CNC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C QFCWVDQHAVTYQZ-UHFFFAOYSA-N 0.000 claims 1
- LUSWPNMUIOFCSE-UHFFFAOYSA-N N-[(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-pyridin-3-ylmethyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C=1C=NC=CC=1)C1CC2CCC(C1)N2C LUSWPNMUIOFCSE-UHFFFAOYSA-N 0.000 claims 1
- 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
- XBBUJUUODZDTIM-MUUNZHRXSA-N N-[(R)-(6-methoxypyridin-3-yl)-pyridin-3-ylmethyl]-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)C=1C=NC=CC=1 XBBUJUUODZDTIM-MUUNZHRXSA-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
- FZDSNKBGDZNFMH-SANMLTNESA-N N-[(S)-(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-SANMLTNESA-N 0.000 claims 1
- XBBUJUUODZDTIM-NDEPHWFRSA-N N-[(S)-(6-methoxypyridin-3-yl)-pyridin-3-ylmethyl]-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)C=1C=NC=CC=1 XBBUJUUODZDTIM-NDEPHWFRSA-N 0.000 claims 1
- FXWHTSYWSMIHKR-UHFFFAOYSA-N N-[1-(4-methoxyphenyl)ethyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound COC1=CC=C(C=C1)C(C)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C FXWHTSYWSMIHKR-UHFFFAOYSA-N 0.000 claims 1
- WVMUIYDRKJHQFV-UHFFFAOYSA-N N-[4-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]cyclohexyl]acetamide Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C1CCC(CC1)NC(C)=O)C=1C=NC=CC=1 WVMUIYDRKJHQFV-UHFFFAOYSA-N 0.000 claims 1
- TVRNGCQYKCLFBW-UHFFFAOYSA-N N-[5-[[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]-pyridin-3-ylmethyl]pyridin-2-yl]acetamide Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C=1C=CC(=NC=1)NC(C)=O)C=1C=NC=CC=1 TVRNGCQYKCLFBW-UHFFFAOYSA-N 0.000 claims 1
- MEWLKSWIIPXHDC-UHFFFAOYSA-N N-[8-(1-methylindol-6-yl)quinoxalin-6-yl]-3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-amine Chemical compound O1CCC(C2=NC=CC=C21)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C MEWLKSWIIPXHDC-UHFFFAOYSA-N 0.000 claims 1
- TYXCMWPULXKEAH-UHFFFAOYSA-N N-[[2-(methylamino)pyridin-4-yl]-pyridin-3-ylmethyl]-8-(1-methylindol-6-yl)quinoxalin-6-amine Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)NC(C=1C=NC=CC=1)C1=CC(=NC=C1)NC TYXCMWPULXKEAH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 108010022678 Phosphofructokinase-2 Proteins 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000016624 Retinal neoplasm Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- GTVOPAJWFDLIEK-FQEVSTJZSA-N [(3S)-3-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]pyrrolidin-1-yl]-pyridin-2-ylmethanone Chemical compound CN1C=CC2=CC=C(C=C12)C=1C=C(C=C2N=CC=NC=12)N[C@@H]1CN(CC1)C(=O)C1=NC=CC=C1 GTVOPAJWFDLIEK-FQEVSTJZSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000003725 azepanyl group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 claims 1
- PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 claims 1
- 201000007455 central nervous system cancer Diseases 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 125000006390 chloropyrimidinyl group Chemical group 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 201000010918 connective tissue cancer Diseases 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims 1
- YZSMJZPWNCOODD-UHFFFAOYSA-N cyclopropyl-[3-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]pyrrolidin-1-yl]methanone Chemical compound C1(CC1)C(=O)N1CC(CC1)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C YZSMJZPWNCOODD-UHFFFAOYSA-N 0.000 claims 1
- UHWPJNZGGJTYSY-UHFFFAOYSA-N cyclopropyl-[4-[[8-(1-methylindol-6-yl)quinoxalin-6-yl]amino]azepan-1-yl]methanone Chemical compound C1(CC1)C(=O)N1CCC(CCC1)NC=1C=C2N=CC=NC2=C(C=1)C1=CC=C2C=CN(C2=C1)C UHWPJNZGGJTYSY-UHFFFAOYSA-N 0.000 claims 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N delta-valerolactam Natural products O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 1
- 125000004586 dihydrobenzopyranyl group Chemical group O1C(CCC2=C1C=CC=C2)* 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 230000001926 lymphatic effect Effects 0.000 claims 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000006393 methylpyrimidinyl group Chemical group 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 230000035479 physiological effects, processes and functions Effects 0.000 claims 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 1
- 201000008933 retinal cancer Diseases 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15460017.5 | 2015-05-13 | ||
| EP15001451.2 | 2015-05-13 | ||
| EP15001451 | 2015-05-13 | ||
| EP15460017 | 2015-05-14 | ||
| PCT/EP2016/000783 WO2016180536A1 (en) | 2015-05-13 | 2016-05-12 | Substituted quinoxaline derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018515612A JP2018515612A (ja) | 2018-06-14 |
| JP2018515612A5 true JP2018515612A5 (https=) | 2019-06-13 |
Family
ID=56081443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018511333A Pending JP2018515612A (ja) | 2015-05-13 | 2016-05-12 | 置換キノキサリン誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20180148429A1 (https=) |
| EP (1) | EP3294729A1 (https=) |
| JP (1) | JP2018515612A (https=) |
| CN (1) | CN107635986A (https=) |
| AU (1) | AU2016261031A1 (https=) |
| CA (1) | CA2979302A1 (https=) |
| IL (1) | IL254870A0 (https=) |
| TW (1) | TW201713641A (https=) |
| WO (1) | WO2016180536A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20190292176A1 (en) * | 2016-07-14 | 2019-09-26 | Bistol-Myers Squibb Company | Bicyclic heteroaryl substituted compounds |
| CN109890809A (zh) * | 2016-11-08 | 2019-06-14 | 默克专利股份公司 | 作为pfkfb的抑制剂的取代的喹喔啉衍生物 |
| GB201705263D0 (en) * | 2017-03-31 | 2017-05-17 | Probiodrug Ag | Novel inhibitors |
| EP3689866A4 (en) * | 2017-09-26 | 2021-07-07 | Nippon Soda Co., Ltd. | QUINOLINE COMPOUND AND BACTERICIDAL AGENT FOR AGRICULTURE AND HORTICULTURE |
| WO2019134985A1 (en) | 2018-01-08 | 2019-07-11 | F. Hoffmann-La Roche Ag | Octahydropyrido[1,2-alpha]pyrazines as magl inhibitors |
| PE20201185A1 (es) | 2018-03-22 | 2020-11-03 | Hoffmann La Roche | Inhibidores de la oxacina monoacilglicerol lipasa (magl) |
| US12448374B2 (en) | 2018-06-07 | 2025-10-21 | Disarm Therapeutics, Inc. | Inhibitors of SARM1 |
| ES2986417T3 (es) | 2018-08-13 | 2024-11-11 | Hoffmann La Roche | Nuevos compuestos heterocíclicos como inhibidores de la monoacilglicerol lipasa |
| AU2019362747A1 (en) * | 2018-10-15 | 2021-06-03 | Gero Pte. Ltd. | PFKFB3 inhibitors and their uses |
| ES2955037T3 (es) | 2018-11-22 | 2023-11-28 | Hoffmann La Roche | Nuevos compuestos heterocíclicos |
| WO2020113094A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| WO2020132045A1 (en) | 2018-12-19 | 2020-06-25 | Disarm Therapeutics, Inc. | Inhibitors of sarm1 in combination with neuroprotective agents |
| MX2022001548A (es) * | 2019-08-06 | 2022-04-18 | Univ North Carolina Chapel Hill | Ligandos que se dirigen a arn, composiciones de estos y métodos para elaborarlos y utilizarlos. |
| CN110698418B (zh) * | 2019-09-11 | 2022-07-01 | 广西师范大学 | 一种3-芳胺基喹喔啉-2-甲酰胺类衍生物及其制备方法和应用 |
| EP4028403B1 (en) | 2019-09-12 | 2023-11-22 | F. Hoffmann-La Roche AG | 4,4a,5,7,8,8a-hexapyrido[4,3-b][1,4]oxazin-3-one compounds as magl inhibitors |
| PE20221450A1 (es) | 2019-09-23 | 2022-09-21 | Hoffmann La Roche | Compuestos heterociclicos |
| EP4146652A1 (en) * | 2020-05-08 | 2023-03-15 | Merck Patent GmbH | Tricyclic heterocycles useful as tead binders |
| PH12022553233A1 (en) * | 2020-07-23 | 2024-02-12 | Cancer Research Tech Ltd | Tricyclic heterocycles |
| WO2022043284A1 (en) | 2020-08-26 | 2022-03-03 | F. Hoffmann-La Roche Ag | Heterocyclic compounds useful as magl inhibitors |
| MX2023002224A (es) | 2020-09-03 | 2023-03-15 | Hoffmann La Roche | Compuestos heterociclicos. |
| TW202237610A (zh) | 2020-11-25 | 2022-10-01 | 法商施維雅藥廠 | 新穎有機化合物 |
| JP2024522354A (ja) * | 2021-06-02 | 2024-06-18 | ザ ユニバーシティ オブ ノース カロライナ アット チャペル ヒル | Ｒｎａを標的とするリガンド、それらの組成物、及びそれらを作製し使用する方法 |
| JP2025525350A (ja) | 2022-06-24 | 2025-08-05 | エフ． ホフマン－ラ ロシュ アーゲー | Ｍａｇｌ阻害剤としての新規複素環－カルボニル－環式化合物 |
| WO2025084787A1 (ko) * | 2023-10-17 | 2025-04-24 | 가천대학교 산학협력단 | 신규 퀴녹살린 화합물, 이의 제조방법 및 이의 용도 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5633218A (en) * | 1995-05-24 | 1997-05-27 | E. I. Du Pont De Nemours And Company | Herbicidal benzodioxoles and benzodioxanes |
| US20140128392A1 (en) * | 2009-03-19 | 2014-05-08 | Bioenergenix | Heterocyclic compounds for the inhibition of pask |
| US9403769B2 (en) * | 2010-02-22 | 2016-08-02 | Advanced Cancer Therapeutics, Llc | Small molecule inhibitors of PFKFB3 and glycolytic flux and their methods of use as anti-cancer therapeutics |
| TW201311149A (zh) * | 2011-06-24 | 2013-03-16 | Ishihara Sangyo Kaisha | 有害生物防治劑 |
| IN2014DN08886A (https=) * | 2012-03-29 | 2015-05-22 | Advanced Cancer Therapeutics Llc |
-
2016
- 2016-05-12 JP JP2018511333A patent/JP2018515612A/ja active Pending
- 2016-05-12 CA CA2979302A patent/CA2979302A1/en not_active Abandoned
- 2016-05-12 US US15/572,470 patent/US20180148429A1/en not_active Abandoned
- 2016-05-12 TW TW105114781A patent/TW201713641A/zh unknown
- 2016-05-12 CN CN201680027578.3A patent/CN107635986A/zh active Pending
- 2016-05-12 AU AU2016261031A patent/AU2016261031A1/en not_active Abandoned
- 2016-05-12 WO PCT/EP2016/000783 patent/WO2016180536A1/en not_active Ceased
- 2016-05-12 EP EP16725031.5A patent/EP3294729A1/en not_active Withdrawn
-
2017
- 2017-10-03 IL IL254870A patent/IL254870A0/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018515612A5 (https=) | ||
| JP7460593B2 (ja) | サイクリン依存性キナーゼ７（ｃｄｋ７）の阻害剤 | |
| US11130759B1 (en) | 2-oxoquinazoline derivatives as methionine adenosyltransferase 2A inhibitors | |
| JP6117235B2 (ja) | Ｐｉ３ｋの活性または機能の阻害剤の使用 | |
| JP6200520B2 (ja) | 置換２−アミノピリジンプロテインキナーゼ阻害剤 | |
| ES2966457T3 (es) | Derivados de pirazol como inhibidores de MALT1 | |
| TW201713641A (zh) | 經取代之喹喏啉衍生物 | |
| JP2013501002A (ja) | Ｓｙｋキナーゼ阻害剤としての化合物および組成物 | |
| KR20160135283A (ko) | 5-치환된 인다졸-3-카르복스아미드 및 이의 제조 및 용도 | |
| JP2013500972A (ja) | Ｓｙｋキナーゼ阻害剤としての２，７−ナフチリジン−１−オン誘導体 | |
| JP2013525498A5 (https=) | ||
| MX2010008421A (es) | Compuestos y composiciones como inhbidores de cinasa. | |
| KR20130038420A (ko) | 브루톤 티로신 키나아제의 억제제 | |
| CA2798622A1 (en) | Indoles | |
| AU2012318874A1 (en) | 1,3-substituted azetidine PDE10 inhibitors | |
| JP2010538094A (ja) | チロシンキナーゼ阻害剤としてのピラゾロピリジン類 | |
| JP2023526841A (ja) | ピペラジン環状尿素類 | |
| JP2025512957A (ja) | Ｅｇｆｒ阻害剤 | |
| TW202509019A (zh) | Sarm1調節子、其製劑及用途 | |
| CA3245810A1 (en) | PYRIDO[3,2-D]PYRIMIDINS USED AS HPK1 INHIBITORS | |
| CN121586713A (zh) | 用于治疗疾病的喹啉衍生物及其药物组合物 | |
| AU2024284667A1 (en) | Pyrazolo-pyrimidinone compounds for use in methods of inhibiting wee1 a kinase | |
| TW202115087A (zh) | 作為第iii型受體酪胺酸激酶抑制劑之雜環吡唑衍生物 | |
| HK40012363A (en) | Inhibitors of cyclin-dependent kinase 7 (cdk7) |