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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| JP7058256B2 (ja) * | 2016-07-14 | 2022-04-21 | ブリストル－マイヤーズ スクイブ カンパニー | 二環式ヘテロアリール置換化合物 |
| JP2019532998A (ja) | 2016-11-08 | 2019-11-14 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Ｐｆｋｆｂ阻害剤としての置換キノキサリン誘導体 |
| 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 |
| WO2019180185A1 (en) | 2018-03-22 | 2019-09-26 | F. Hoffmann-La Roche Ag | Oxazine monoacylglycerol lipase (magl) inhibitors |
| US12448374B2 (en) | 2018-06-07 | 2025-10-21 | Disarm Therapeutics, Inc. | Inhibitors of SARM1 |
| PE20211089A1 (es) | 2018-08-13 | 2021-06-14 | Hoffmann La Roche | Nuevos compuestos heterociclicos como inhibidores de la monoacilglicerol lipasa |
| BR112021007101A2 (pt) * | 2018-10-15 | 2021-07-27 | Gero Discovery Limited Liability Company | composto, composto para uso como neuroprotetor, sal de adição de ácido farmaceuticamente aceitável, derivado, n-óxido, solvato, tautômero, estereoisômero, racemato, sal fisiologicamente aceitável, composição farmacêutica, composições farmacêuticas neuroprotetiva e antienvelhecimento, meio tangível, agente de deleção, diminuição, ligação, inibição ou degradação de pfkfb3, inibidores de pfkfb3, de pfkfb3 para uso em neuroproteção, de atividade de quinase de pfkfb3 de molécula pequena, de atividade de quinase de pfkfb3, de molécula pequena de pfkfb3 e de molécula pequena de atividade de quinase de pfkfb3, kits para tratamento de um quadro mediado por pfkfb3 e/ou pfkfb4, de um câncer, para tratamento antienvelhecimento e para neuroproteção, métodos de imunossupressão e para tratamento de um câncer, de tumor sólido, de um câncer hematológico, de um câncer ósseo, de osteosarcoma, de doença, de isquemia cerebral, de derrame isquêmico neonatal, de insulto neurológico, de derrame isquêmico, de envelhecimento acelerado de sobrevivente de câncer, de envelhecimento acelerado de indivíduo sofrendo de hiv, de uma lesão traumática no cérebro, de um indivíduo humano após lesão no sistema nervoso central aguda, para o tratamento de um transtorno associado à modulação de níveis f-2,6-p2 em um mamífero, para tratamento ou prevenção de um transtorno ou doença relacionada à idade ou outro tratamento antienvelhecimento e para prevenção ou tratamento de consequências da quimioterapia e da radioterapia, para tratamento ou profilaxia de doença ou quadro no qual a inibição de glicólise tem efeito benéfico, de doença neurodegenerativa ou quadro no qual a inibição de glicólise tem efeito benéfico e de doença neurodegenerativa ou quadro neurodegenerativo, para intensificar o efeito de tratamento de câncer por radiação, o efeito de tratamento de câncer ósseo por radiação e o efeito de tratamento de osteosarcoma por radiação, para reduzir a capacidade de as células cancerosas repararem seu dna e reduzir inflamação aterosclerótica e/ou pelo menos uma de suas consequências clínicas, para sensibilizar a célula cancerosa para a terapia citostática e/ou de radiação, e, métodos para neuroproteção, para fabricação de uma medicação, para fabricação de uma medicação de neuroproteção, para aumento de capacidade antioxidante de célula, para reduzir uma absorção glicolítica no neurônio, para prevenção de morte apoptótica do neurônio, para reduzir uma absorção glicolítica no astrócito, para inibição reativa à proliferação de astrócito, para proteção de um neurônio contra a excitotoxicidade, para proteção de um neurônio entérico contra a excitotoxicidade, para atenuação ou prevenção de dano neuronal em um indivíduo humano, para prevenção ou tratamento de doença relacionada ao envelhecimento, para melhoria de um parâmetro, para rejuvenescimento, para radioproteção, para a mudança de biomarcador ou biomarcadores de mortalidade, para a mudança de biomarcador ou biomarcadores de longevidade ou |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| EP3897670A4 (en) | 2018-12-19 | 2022-09-07 | Disarm Therapeutics, Inc. | MRSA1 INHIBITORS IN COMBINATION WITH NEUROPROTECTIVE AGENTS |
| CN121045142A (zh) * | 2019-08-06 | 2025-12-02 | 北卡罗来纳查佩尔山大学 | Rna靶向配体、其组合物以及其制备和使用方法 |
| 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 |
| MX2022002311A (es) | 2019-09-12 | 2022-03-25 | Hoffmann La Roche | Compuestos de 4,4a,5,7,8,8a-hexapirido[4,3-b][1,4]oxazin-3-ona como inhibidores de monoacilglicerol lipasa (magl). |
| 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 |
| EP4185564A1 (en) * | 2020-07-23 | 2023-05-31 | Merck Patent GmbH | Tricyclic heterocycles |
| CN116096723A (zh) | 2020-08-26 | 2023-05-09 | 豪夫迈·罗氏有限公司 | 用作magl抑制剂的杂环化合物 |
| WO2022049134A1 (en) | 2020-09-03 | 2022-03-10 | F. Hoffmann-La Roche Ag | Heterocyclic compounds |
| TW202237610A (zh) | 2020-11-25 | 2022-10-01 | 法商施維雅藥廠 | 新穎有機化合物 |
| IL308879A (en) * | 2021-06-02 | 2024-01-01 | Univ North Carolina Chapel Hill | RNA-directing ligands, their compositions, and methods for their production and use |
| WO2023247670A1 (en) | 2022-06-24 | 2023-12-28 | 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 CA CA2979302A patent/CA2979302A1/en not_active Abandoned
- 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 US US15/572,470 patent/US20180148429A1/en not_active Abandoned
- 2016-05-12 TW TW105114781A patent/TW201713641A/zh unknown
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2017
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