JP2018515612A5 - - Google Patents
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- 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
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- -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
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| CN109689647B (zh) * | 2016-07-14 | 2023-01-20 | 百时美施贵宝公司 | 二环杂芳基取代的化合物 |
| US20190256499A1 (en) | 2016-11-08 | 2019-08-22 | Merck Patent Gmbh | Substituted quinoxaline derivatives as inhibitors of pfkfb |
| GB201705263D0 (en) * | 2017-03-31 | 2017-05-17 | Probiodrug Ag | Novel inhibitors |
| WO2019065516A1 (ja) * | 2017-09-26 | 2019-04-04 | 日本曹達株式会社 | キノリン化合物および農園芸用殺菌剤 |
| EP3737680A1 (en) | 2018-01-08 | 2020-11-18 | F. Hoffmann-La Roche AG | Octahydropyrido[1,2-alpha]pyrazines as magl inhibitors |
| HRP20230388T1 (hr) | 2018-03-22 | 2023-06-23 | F. Hoffmann - La Roche Ag | Inhibitori oksazin monoacilglicerol lipaze (magl) |
| WO2019236884A1 (en) | 2018-06-07 | 2019-12-12 | Disarm Therapeutics, Inc. | Inhibitors of sarm1 |
| EP3837263B1 (en) | 2018-08-13 | 2024-07-03 | F. Hoffmann-La Roche AG | New heterocyclic compounds as monoacylglycerol lipase inhibitors |
| EP3867226A4 (en) * | 2018-10-15 | 2022-11-23 | Gero Pte. Ltd. | PFKFB3 INHIBITORS AND THEIR USES |
| EP3883936B1 (en) | 2018-11-22 | 2023-07-12 | F. Hoffmann-La Roche AG | New heterocyclic compounds |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CA3123215C (en) | 2018-12-19 | 2024-04-02 | Disarm Therapeutics, Inc. | Inhibitors of sarm1 in combination with neuroprotective agents |
| WO2021026245A1 (en) * | 2019-08-06 | 2021-02-11 | The University Of North Carolina At Chapel Hill | Rna-targeting ligands, compositions thereof, and methods of making and using the same |
| 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 |
| US11814375B2 (en) | 2019-09-12 | 2023-11-14 | Hoffmann-La Roche Inc. | Heterocyclic compounds |
| MX2022003023A (es) | 2019-09-23 | 2022-04-07 | Hoffmann La Roche | Compuestos heterociclicos. |
| US20240317753A9 (en) * | 2020-05-08 | 2024-09-26 | Merck Patent Gmbh | Tricyclic heterocycles |
| IL300048A (en) * | 2020-07-23 | 2023-03-01 | Merck Patent Gmbh | Heterocyclic compounds with three rings, their preparation and use |
| 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. |
| US20220169654A1 (en) | 2020-11-25 | 2022-06-02 | Servier Pharmaceuticals Llc | New Organic Compounds |
| PH12023553248A1 (en) * | 2021-06-02 | 2024-03-25 | Univ North Carolina Chapel Hill | Rna-targeting ligands, compositions thereof, and methods of making and using the same |
| EP4543870A1 (en) | 2022-06-24 | 2025-04-30 | F. Hoffmann-La Roche AG | New heterocyclic-carbonyl-cyclic compounds as magl inhibitors |
| WO2025084787A1 (ko) * | 2023-10-17 | 2025-04-24 | 가천대학교 산학협력단 | 신규 퀴녹살린 화합물, 이의 제조방법 및 이의 용도 |
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| 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 |
| WO2011103557A1 (en) * | 2010-02-22 | 2011-08-25 | 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 |
| CA2868787A1 (en) * | 2012-03-29 | 2013-10-03 | Advanced Cancer Therapeutics, Llc | Pfkfb3 inhibitor and methods of use as an anti-cancer therapeutic |
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- 2016-05-12 AU AU2016261031A patent/AU2016261031A1/en not_active Abandoned
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2017
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