JPWO2020052688A5 - - Google Patents
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- Publication number
- JPWO2020052688A5 JPWO2020052688A5 JP2021514039A JP2021514039A JPWO2020052688A5 JP WO2020052688 A5 JPWO2020052688 A5 JP WO2020052688A5 JP 2021514039 A JP2021514039 A JP 2021514039A JP 2021514039 A JP2021514039 A JP 2021514039A JP WO2020052688 A5 JPWO2020052688 A5 JP WO2020052688A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- fluoro
- isopropyl
- imidazo
- dihydro
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 230000008499 blood brain barrier function Effects 0.000 claims description 12
- 210000001218 blood-brain barrier Anatomy 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 238000001959 radiotherapy Methods 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 210000004556 brain Anatomy 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 208000005017 glioblastoma Diseases 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 230000001737 promoting effect Effects 0.000 claims description 4
- 108010006654 Bleomycin Proteins 0.000 claims description 3
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 claims description 3
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 3
- 229930192392 Mitomycin Natural products 0.000 claims description 3
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims description 3
- 229940034982 antineoplastic agent Drugs 0.000 claims description 3
- 239000002246 antineoplastic agent Substances 0.000 claims description 3
- YTKUWDBFDASYHO-UHFFFAOYSA-N bendamustine Chemical compound ClCCN(CCCl)C1=CC=C2N(C)C(CCCC(O)=O)=NC2=C1 YTKUWDBFDASYHO-UHFFFAOYSA-N 0.000 claims description 3
- 229960002707 bendamustine Drugs 0.000 claims description 3
- 229960001561 bleomycin Drugs 0.000 claims description 3
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims description 3
- 229960005243 carmustine Drugs 0.000 claims description 3
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 3
- 229960004630 chlorambucil Drugs 0.000 claims description 3
- 229960004397 cyclophosphamide Drugs 0.000 claims description 3
- 229960004679 doxorubicin Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229960005420 etoposide Drugs 0.000 claims description 3
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 3
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims description 3
- 229960001101 ifosfamide Drugs 0.000 claims description 3
- 229960004768 irinotecan Drugs 0.000 claims description 3
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 3
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims description 3
- 229960001924 melphalan Drugs 0.000 claims description 3
- 229960004857 mitomycin Drugs 0.000 claims description 3
- -1 nitro, hydroxyl Chemical group 0.000 claims description 3
- 229960000303 topotecan Drugs 0.000 claims description 3
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims description 3
- CCPABWZMHLKHOU-UHFFFAOYSA-N 7-fluoro-3-methyl-1-propan-2-yl-8-[6-(2-pyrrolidin-1-ylethoxymethyl)pyridin-3-yl]imidazo[4,5-c]cinnolin-2-one Chemical compound C1(F)=C(C2=CN=C(C=C2)COCCN2CCCC2)C=C2C=3N(C(=O)N(C=3N=NC2=C1)C)C(C)C CCPABWZMHLKHOU-UHFFFAOYSA-N 0.000 claims description 2
- UNCGOLKXUDKPKS-UHFFFAOYSA-N 7-fluoro-3-methyl-1-propan-2-yl-8-[6-(3-pyrrolidin-1-ylpropoxy)pyridin-3-yl]imidazo[4,5-c]cinnolin-2-one Chemical compound FC1=C(C2=CN=C(OCCCN3CCCC3)C=C2)C=C2C=3N(C(=O)N(C=3N=NC2=C1)C)C(C)C UNCGOLKXUDKPKS-UHFFFAOYSA-N 0.000 claims description 2
- DCCDYBCUHXTDSC-UHFFFAOYSA-N 7-fluoro-3-methyl-8-[6-(2-morpholin-4-ylethoxymethyl)pyridin-3-yl]-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound FC=1C(=CC=2C3=C(N=NC=2C=1)N(C(N3C(C)C)=O)C)C=1C=NC(=CC=1)COCCN1CCOCC1 DCCDYBCUHXTDSC-UHFFFAOYSA-N 0.000 claims description 2
- TYZAHWGVMYFMBR-UHFFFAOYSA-N 7-fluoro-3-methyl-8-[6-(2-piperazin-1-ylethoxymethyl)pyridin-3-yl]-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound FC=1C(=CC=2C3=C(N=NC=2C=1)N(C(N3C(C)C)=O)C)C=1C=NC(=CC=1)COCCN1CCNCC1 TYZAHWGVMYFMBR-UHFFFAOYSA-N 0.000 claims description 2
- ZEOACOGRBZQJJQ-UHFFFAOYSA-N 7-fluoro-3-methyl-8-[6-(2-piperidin-1-ylethoxymethyl)pyridin-3-yl]-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound FC1=C(C2=CN=C(C=C2)COCCN2CCCCC2)C=C2C=3N(C(=O)N(C=3N=NC2=C1)C)C(C)C ZEOACOGRBZQJJQ-UHFFFAOYSA-N 0.000 claims description 2
- GIUQJDQSFVEXFY-UHFFFAOYSA-N 7-fluoro-3-methyl-8-[6-(3-morpholin-4-ylpropoxy)pyridin-3-yl]-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound FC=1C(=CC=2C3=C(N=NC=2C=1)N(C(N3C(C)C)=O)C)C=1C=NC(=CC=1)OCCCN1CCOCC1 GIUQJDQSFVEXFY-UHFFFAOYSA-N 0.000 claims description 2
- YAKKZOPXKUUTNR-UHFFFAOYSA-N 7-fluoro-3-methyl-8-[6-(3-piperazin-1-ylpropoxy)pyridin-3-yl]-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound FC=1C(=CC=2C3=C(N=NC=2C=1)N(C(N3C(C)C)=O)C)C=1C=NC(=CC=1)OCCCN1CCNCC1 YAKKZOPXKUUTNR-UHFFFAOYSA-N 0.000 claims description 2
- HONSNEDYRQWJPQ-UHFFFAOYSA-N 7-fluoro-3-methyl-8-[6-[2-(2-oxa-6-azaspiro[3.3]heptan-6-yl)ethoxymethyl]pyridin-3-yl]-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C1OCC11CN(C1)CCOCC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C HONSNEDYRQWJPQ-UHFFFAOYSA-N 0.000 claims description 2
- DHZMCFVDHAUXMV-UHFFFAOYSA-N 7-fluoro-3-methyl-8-[6-[2-(4-methylpiperazin-1-yl)ethoxymethyl]pyridin-3-yl]-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound FC=1C(=CC=2C3=C(N=NC=2C=1)N(C(N3C(C)C)=O)C)C=1C=NC(=CC=1)COCCN1CCN(CC1)C DHZMCFVDHAUXMV-UHFFFAOYSA-N 0.000 claims description 2
- PVEAQAXOZICBCB-UHFFFAOYSA-N 7-fluoro-3-methyl-8-[6-[3-(2-oxa-6-azaspiro[3.3]heptan-6-yl)propoxy]pyridin-3-yl]-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C1OCC11CN(C1)CCCOC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C PVEAQAXOZICBCB-UHFFFAOYSA-N 0.000 claims description 2
- SZWAOZFEAGDCSW-UHFFFAOYSA-N 7-fluoro-3-methyl-8-[6-[3-(4-methylpiperazin-1-yl)propoxy]pyridin-3-yl]-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound FC=1C(=CC=2C3=C(N=NC=2C=1)N(C(N3C(C)C)=O)C)C=1C=NC(=CC=1)OCCCN1CCN(CC1)C SZWAOZFEAGDCSW-UHFFFAOYSA-N 0.000 claims description 2
- ODTOPIDGJZLIEA-UHFFFAOYSA-N 7-fluoro-8-[6-[2-(4-fluoropiperidin-1-yl)ethoxymethyl]pyridin-3-yl]-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound FC=1C(=CC=2C3=C(N=NC=2C=1)N(C(N3C(C)C)=O)C)C=1C=NC(=CC=1)COCCN1CCC(CC1)F ODTOPIDGJZLIEA-UHFFFAOYSA-N 0.000 claims description 2
- XQILLFFLOKQCIG-QGZVFWFLSA-N 7-fluoro-8-[6-[2-[(3R)-3-fluoropyrrolidin-1-yl]ethoxymethyl]pyridin-3-yl]-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound FC=1C(=CC=2C3=C(N=NC=2C=1)N(C(N3C(C)C)=O)C)C=1C=NC(=CC=1)COCCN1C[C@@H](CC1)F XQILLFFLOKQCIG-QGZVFWFLSA-N 0.000 claims description 2
- IAWLWEIRGGUDTG-UHFFFAOYSA-N 7-fluoro-8-[6-[3-(4-fluoropiperidin-1-yl)propoxy]pyridin-3-yl]-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound FC=1C(=CC=2C3=C(N=NC=2C=1)N(C(N3C(C)C)=O)C)C=1C=NC(=CC=1)OCCCN1CCC(CC1)F IAWLWEIRGGUDTG-UHFFFAOYSA-N 0.000 claims description 2
- BTKVAQIEQCVAIF-QGZVFWFLSA-N 7-fluoro-8-[6-[3-[(3R)-3-fluoropyrrolidin-1-yl]propoxy]pyridin-3-yl]-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound FC=1C(=CC=2C3=C(N=NC=2C=1)N(C(N3C(C)C)=O)C)C=1C=NC(=CC=1)OCCCN1C[C@@H](CC1)F BTKVAQIEQCVAIF-QGZVFWFLSA-N 0.000 claims description 2
- BTKVAQIEQCVAIF-KRWDZBQOSA-N 7-fluoro-8-[6-[3-[(3S)-3-fluoropyrrolidin-1-yl]propoxy]pyridin-3-yl]-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound FC=1C(=CC=2C3=C(N=NC=2C=1)N(C(N3C(C)C)=O)C)C=1C=NC(=CC=1)OCCCN1C[C@H](CC1)F BTKVAQIEQCVAIF-KRWDZBQOSA-N 0.000 claims description 2
- FWEGZXVOHJHGBC-UHFFFAOYSA-N 8-[6-[2-(2-azaspiro[3.3]heptan-2-yl)ethoxymethyl]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C1N(CC11CCC1)CCOCC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C FWEGZXVOHJHGBC-UHFFFAOYSA-N 0.000 claims description 2
- LRLFYYXKMQFEMF-UHFFFAOYSA-N 8-[6-[2-(3-azabicyclo[3.1.0]hexan-3-yl)ethoxymethyl]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C12CN(CC2C1)CCOCC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C LRLFYYXKMQFEMF-UHFFFAOYSA-N 0.000 claims description 2
- VSFKZXPUYPRRII-UHFFFAOYSA-N 8-[6-[2-(4-cyclopropylpiperazin-1-yl)ethoxymethyl]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C1(CC1)N1CCN(CC1)CCOCC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C VSFKZXPUYPRRII-UHFFFAOYSA-N 0.000 claims description 2
- IDNUGDIHZPUFNV-UHFFFAOYSA-N 8-[6-[2-(6-azabicyclo[3.2.0]heptan-6-yl)ethoxymethyl]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C12CCCC2N(C1)CCOCC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C IDNUGDIHZPUFNV-UHFFFAOYSA-N 0.000 claims description 2
- SDNSUKXTUQUVEK-UHFFFAOYSA-N 8-[6-[2-(diethylamino)ethoxymethyl]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C(C)N(CCOCC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C)CC SDNSUKXTUQUVEK-UHFFFAOYSA-N 0.000 claims description 2
- QKRLOASRBKEUND-UHFFFAOYSA-N 8-[6-[2-(dimethylamino)ethoxymethyl]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound CN(CCOCC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C)C QKRLOASRBKEUND-UHFFFAOYSA-N 0.000 claims description 2
- BUJMFUGHAASTKK-UHFFFAOYSA-N 8-[6-[2-[ethyl(methyl)amino]ethoxymethyl]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C(C)N(CCOCC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C)C BUJMFUGHAASTKK-UHFFFAOYSA-N 0.000 claims description 2
- VTKIBPPEYRNZRK-UHFFFAOYSA-N 8-[6-[3-(2-azaspiro[3.3]heptan-2-yl)propoxy]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C1N(CC11CCC1)CCCOC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C VTKIBPPEYRNZRK-UHFFFAOYSA-N 0.000 claims description 2
- ZAKWFUKOHGBXKM-UHFFFAOYSA-N 8-[6-[3-(2-azaspiro[3.4]octan-2-yl)propoxy]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C1N(CC11CCCC1)CCCOC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C ZAKWFUKOHGBXKM-UHFFFAOYSA-N 0.000 claims description 2
- SSPRJXNUFWSIDY-UHFFFAOYSA-N 8-[6-[3-(3-azabicyclo[3.1.0]hexan-3-yl)propoxy]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C12CN(CC2C1)CCCOC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C SSPRJXNUFWSIDY-UHFFFAOYSA-N 0.000 claims description 2
- ZVDAUYGPQLIGSS-UHFFFAOYSA-N 8-[6-[3-(4-cyclopropylpiperazin-1-yl)propoxy]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C1(CC1)N1CCN(CC1)CCCOC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C ZVDAUYGPQLIGSS-UHFFFAOYSA-N 0.000 claims description 2
- URUWFSJGHRSZRG-UHFFFAOYSA-N 8-[6-[3-(6-azabicyclo[3.2.0]heptan-6-yl)propoxy]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C12CCCC2N(C1)CCCOC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C URUWFSJGHRSZRG-UHFFFAOYSA-N 0.000 claims description 2
- IOTYLGDBUWBMMT-UHFFFAOYSA-N 8-[6-[3-(diethylamino)propoxy]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C(C)N(CCCOC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C)CC IOTYLGDBUWBMMT-UHFFFAOYSA-N 0.000 claims description 2
- DZJKYNYWKOYGFY-UHFFFAOYSA-N 8-[6-[3-(dimethylamino)propoxy]-2-fluoropyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound CN(CCCOC1=CC=C(C(=N1)F)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C)C DZJKYNYWKOYGFY-UHFFFAOYSA-N 0.000 claims description 2
- AMVIOMPGDDKABN-UHFFFAOYSA-N 8-[6-[3-[(dimethylamino)methyl]pyrrolidin-1-yl]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound CN(C)CC1CN(CC1)C1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C AMVIOMPGDDKABN-UHFFFAOYSA-N 0.000 claims description 2
- VNKMOFIWPQLROW-UHFFFAOYSA-N 8-[6-[3-[ethyl(methyl)amino]propoxy]pyridin-3-yl]-7-fluoro-3-methyl-1-propan-2-ylimidazo[4,5-c]cinnolin-2-one Chemical compound C(C)N(CCCOC1=CC=C(C=N1)C1=CC=2C3=C(N=NC=2C=C1F)N(C(N3C(C)C)=O)C)C VNKMOFIWPQLROW-UHFFFAOYSA-N 0.000 claims description 2
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| JP2024017316A JP2024054247A (ja) | 2018-09-14 | 2024-02-07 | 毛細血管拡張性運動失調症変異（ＡＴＭ）キナーゼの選択的調節物質としての１－イソプロピル－３－メチル－８－（ピリジン－３－イル）－１，３－ジヒドロ－２Ｈ－イミダゾ［４，５－ｃ］シンノリン－２－オンおよびその使用 |
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| GB202114704D0 (en) * | 2021-10-14 | 2021-12-01 | Univ Birmingham | ATM inhibition |
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| GB201519406D0 (en) | 2015-11-03 | 2015-12-16 | Astrazeneca Ab | Imidazo[4,5-c]quinolin-2-one compounds and their use in treating cancer |
| GB201519568D0 (en) | 2015-11-05 | 2015-12-23 | Astrazeneca Ab | Imidazo[4,5-c]quinolin-2-one compounds and their use in treating cancer |
| CN108884084A (zh) * | 2016-03-21 | 2018-11-23 | 阿斯利康(瑞典)有限公司 | 噌啉-4-胺化合物及其在治疗癌症中的用途 |
| GB201608227D0 (en) | 2016-05-11 | 2016-06-22 | Astrazeneca Ab | Imidazo[4,5-c]quinolin-2-one compounds and their use in treating cancer |
| CN111344293A (zh) * | 2017-09-20 | 2020-06-26 | 阿斯利康(瑞典)有限公司 | 1，3-二氢咪唑并[4，5-c]噌啉-2-酮化合物及其在治疗癌症中的用途 |
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