JPWO2022192794A5 - - Google Patents
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- Publication number
- JPWO2022192794A5 JPWO2022192794A5 JP2023555666A JP2023555666A JPWO2022192794A5 JP WO2022192794 A5 JPWO2022192794 A5 JP WO2022192794A5 JP 2023555666 A JP2023555666 A JP 2023555666A JP 2023555666 A JP2023555666 A JP 2023555666A JP WO2022192794 A5 JPWO2022192794 A5 JP WO2022192794A5
- Authority
- JP
- Japan
- Prior art keywords
- diazabicyclo
- chloro
- methoxy
- octan
- fluoro
- 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 57
- 150000003839 salts Chemical class 0.000 claims 37
- 150000001875 compounds Chemical class 0.000 claims 33
- -1 haloC 1 -C 3 alkyl Chemical group 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 27
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- DRQDAKVHDPXOLC-ACBHZAAOSA-N CN1[C@H](COC(N=C(C2=CC(Cl)=C3C4=CC(O)=CC5=CC=CC(F)=C45)N4CC(CC5)NC5C4)=NC2=C3F)CCC1 Chemical compound CN1[C@H](COC(N=C(C2=CC(Cl)=C3C4=CC(O)=CC5=CC=CC(F)=C45)N4CC(CC5)NC5C4)=NC2=C3F)CCC1 DRQDAKVHDPXOLC-ACBHZAAOSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- KMAWEIDPDPCVGB-SLTAFYQDSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2C(C3)CNC3C2)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(F)=C(C(C(N2C(C3)CNC3C2)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F KMAWEIDPDPCVGB-SLTAFYQDSA-N 0.000 claims 4
- RRUGMGPXABIABE-UHFFFAOYSA-N CN1C(CCC2)C2(COC(N=C(C2=CC(Cl)=C3C4=CC(O)=CC5=CC=CC=C45)N4CC(CC5)NC5C4)=NC2=C3F)CCC1 Chemical compound CN1C(CCC2)C2(COC(N=C(C2=CC(Cl)=C3C4=CC(O)=CC5=CC=CC=C45)N4CC(CC5)NC5C4)=NC2=C3F)CCC1 RRUGMGPXABIABE-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- RQNGXLRURAEBSY-GPANFISMSA-N CC1=CC(N)=NC(C(C(Cl)=CC(C2=N3)=C(N4CC(CC5)NC5C4)N=C3OC[C@H]3N(C)CCC3)=C2F)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(Cl)=CC(C2=N3)=C(N4CC(CC5)NC5C4)N=C3OC[C@H]3N(C)CCC3)=C2F)=C1C(F)(F)F RQNGXLRURAEBSY-GPANFISMSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- LKPJZPYLQOKZOH-UHFFFAOYSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OCC2(CN(CCC4)CC4C(F)(F)F)CC2)=C3Cl)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OCC2(CN(CCC4)CC4C(F)(F)F)CC2)=C3Cl)=C1C(F)(F)F LKPJZPYLQOKZOH-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 102200006539 rs121913529 Human genes 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- UACBBBIZGYQMMT-XBMUEBEBSA-N 4-[6-chloro-4-(2,5-diazabicyclo[2.2.1]heptan-2-yl)-8-fluoro-2-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]quinazolin-7-yl]naphthalen-2-ol Chemical compound CN1[C@H](COC2=NC(N3C(C4)CNC4C3)=C(C=C(C(C3=CC(O)=CC4=C3C=CC=C4)=C3F)Cl)C3=N2)CCC1 UACBBBIZGYQMMT-XBMUEBEBSA-N 0.000 claims 1
- CESQHARCORSXSH-ACBHZAAOSA-N 4-[6-chloro-4-(3,6-diazabicyclo[3.1.1]heptan-3-yl)-8-fluoro-2-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]quinazolin-7-yl]naphthalen-2-ol Chemical compound CN1[C@H](COC2=NC(N3CC(C4)NC4C3)=C(C=C(C(C3=CC(O)=CC4=CC=CC=C34)=C3F)Cl)C3=N2)CCC1 CESQHARCORSXSH-ACBHZAAOSA-N 0.000 claims 1
- ZGEALGCPGNZXFN-MHJFOBGBSA-N 4-[6-chloro-4-(3,8-diazabicyclo[3.2.1]octan-3-yl)-8-fluoro-2-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]quinazolin-7-yl]naphthalen-2-ol Chemical compound CN1[C@H](COC2=NC(N3CC(CC4)NC4C3)=C(C=C(C(C3=CC(O)=CC4=CC=CC=C34)=C3F)Cl)C3=N2)CCC1 ZGEALGCPGNZXFN-MHJFOBGBSA-N 0.000 claims 1
- UACBBBIZGYQMMT-CEXWTWQISA-N 4-[6-chloro-4-[(1R,4R)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-8-fluoro-2-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]quinazolin-7-yl]naphthalen-2-ol Chemical compound CN1[C@H](COC2=NC(N3[C@H](C4)CN[C@H]4C3)=C(C=C(C(C3=C(C=CC=C4)C4=CC(O)=C3)=C3F)Cl)C3=N2)CCC1 UACBBBIZGYQMMT-CEXWTWQISA-N 0.000 claims 1
- ARMCUZCDCGQSRN-DDRJZQQSSA-N C#CC(C(C(C1=CC=C2C(N3CC(CC4)NC4C3)=NC(OCC3(CN(CC4)C[C@@H]4F)CC3)=NC2=C1F)=C1)=C(C=C2)C=C1O)=C2F Chemical compound C#CC(C(C(C1=CC=C2C(N3CC(CC4)NC4C3)=NC(OCC3(CN(CC4)C[C@@H]4F)CC3)=NC2=C1F)=C1)=C(C=C2)C=C1O)=C2F ARMCUZCDCGQSRN-DDRJZQQSSA-N 0.000 claims 1
- WTSCGGZQQZUWKO-ABHNRTSZSA-N CC(C=CC1=C2C=NN1)=C2C(C(Cl)=CC(C1=N2)=C(N3CC(CC4)NC4C3)N=C2OC[C@H]2N(C)CCC2)=C1F Chemical compound CC(C=CC1=C2C=NN1)=C2C(C(Cl)=CC(C1=N2)=C(N3CC(CC4)NC4C3)N=C2OC[C@H]2N(C)CCC2)=C1F WTSCGGZQQZUWKO-ABHNRTSZSA-N 0.000 claims 1
- HUBBLMXNOWRLOD-HRTMPFAESA-N CC(C=CC1=CC=CC=C11)=C1C(C(F)=C(C(C(N1CC(CC2)NC2C1)=N1)=C2)N=C1OC[C@H]1N(C)CCC1)=C2Cl Chemical compound CC(C=CC1=CC=CC=C11)=C1C(C(F)=C(C(C(N1CC(CC2)NC2C1)=N1)=C2)N=C1OC[C@H]1N(C)CCC1)=C2Cl HUBBLMXNOWRLOD-HRTMPFAESA-N 0.000 claims 1
- CEUFYDIQHTVTIS-GPANFISMSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2C(CC3)CNC3C2)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(F)=C(C(C(N2C(CC3)CNC3C2)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F CEUFYDIQHTVTIS-GPANFISMSA-N 0.000 claims 1
- OPJRQDMBFBXEJJ-NFOMZHRRSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2C3CNCC2C3)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(F)=C(C(C(N2C3CNCC2C3)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F OPJRQDMBFBXEJJ-NFOMZHRRSA-N 0.000 claims 1
- FVKNBMYAVMTCHR-GPANFISMSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2C3CNCC2CC3)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(F)=C(C(C(N2C3CNCC2CC3)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F FVKNBMYAVMTCHR-GPANFISMSA-N 0.000 claims 1
- MESGWJLPYGQMBQ-JCYILVPMSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2C3CNCC2CCC3)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(F)=C(C(C(N2C3CNCC2CCC3)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F MESGWJLPYGQMBQ-JCYILVPMSA-N 0.000 claims 1
- PBQRAHWOIDUWHW-NRXISQOPSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(C3)NC3C2)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(C3)NC3C2)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F PBQRAHWOIDUWHW-NRXISQOPSA-N 0.000 claims 1
- YHYOKWRICMLNNL-JCYILVPMSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)N(C)C3C2)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)N(C)C3C2)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F YHYOKWRICMLNNL-JCYILVPMSA-N 0.000 claims 1
- MKLFFLHLFVAODY-UHFFFAOYSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OCC2(CN(CC4)CCC4C(F)(F)F)CC2)=C3Cl)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OCC2(CN(CC4)CCC4C(F)(F)F)CC2)=C3Cl)=C1C(F)(F)F MKLFFLHLFVAODY-UHFFFAOYSA-N 0.000 claims 1
- WQSYEUPAHLEDOE-WWDZGPRUSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OCC2(CN(CC4)C[C@@H]4F)CC2)=C3Cl)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OCC2(CN(CC4)C[C@@H]4F)CC2)=C3Cl)=C1C(F)(F)F WQSYEUPAHLEDOE-WWDZGPRUSA-N 0.000 claims 1
- PZQCFBNFGNAAKP-YVWXJRSOSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@]2(CCC4)[C@@H]4N(C)CCC2)=C3Cl)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@]2(CCC4)[C@@H]4N(C)CCC2)=C3Cl)=C1C(F)(F)F PZQCFBNFGNAAKP-YVWXJRSOSA-N 0.000 claims 1
- FGQRPOCWBWKYIQ-JCYILVPMSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CCC3)NC3C2)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CCC3)NC3C2)=N2)=C3)N=C2OC[C@H]2N(C)CCC2)=C3Cl)=C1C(F)(F)F FGQRPOCWBWKYIQ-JCYILVPMSA-N 0.000 claims 1
- FGSYRIKFPAJSPK-ABHNRTSZSA-N CC1=CC=CC(F)=C1C(C(F)=C(C(C(N1CC(CC2)NC2C1)=N1)=C2)N=C1OC[C@H]1N(C)CCC1)=C2Cl Chemical compound CC1=CC=CC(F)=C1C(C(F)=C(C(C(N1CC(CC2)NC2C1)=N1)=C2)N=C1OC[C@H]1N(C)CCC1)=C2Cl FGSYRIKFPAJSPK-ABHNRTSZSA-N 0.000 claims 1
- JVHXDBMMZJLCRO-BYNFTBRNSA-N CCC1=C2C(C3=CC=C4C(N5CC(CC6)NC6C5)=NC(OC[C@]5(CCC6)[C@@H]6N(C)CCC5)=NC4=C3F)=CC(O)=CC2=CC=C1 Chemical compound CCC1=C2C(C3=CC=C4C(N5CC(CC6)NC6C5)=NC(OC[C@]5(CCC6)[C@@H]6N(C)CCC5)=NC4=C3F)=CC(O)=CC2=CC=C1 JVHXDBMMZJLCRO-BYNFTBRNSA-N 0.000 claims 1
- AGZNSWXQMUVYOW-PEVXEQIPSA-N CN(C1)[C@H](COC2=NC(N3CC(CC4)NC4C3)=C(C=C(C(C3=C(C=CC=C4)C4=CC(O)=C3)=C3F)Cl)C3=N2)C[C@H]1OC Chemical compound CN(C1)[C@H](COC2=NC(N3CC(CC4)NC4C3)=C(C=C(C(C3=C(C=CC=C4)C4=CC(O)=C3)=C3F)Cl)C3=N2)C[C@H]1OC AGZNSWXQMUVYOW-PEVXEQIPSA-N 0.000 claims 1
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- HAILICLPHJTZPS-UHFFFAOYSA-N CN1C(COC)(COC(N=C(C2=CC(Cl)=C3C4=CC(O)=CC5=CC=CC=C45)N4CC(CC5)NC5C4)=NC2=C3F)CCC1 Chemical compound CN1C(COC)(COC(N=C(C2=CC(Cl)=C3C4=CC(O)=CC5=CC=CC=C45)N4CC(CC5)NC5C4)=NC2=C3F)CCC1 HAILICLPHJTZPS-UHFFFAOYSA-N 0.000 claims 1
- IWCQWXMUEKFECE-GZNCHQMQSA-N CN1C[C@H](COC2=NC(N3CC(CC4)NC4C3)=C(C=C(C(C3=CC(O)=CC4=CC=CC=C34)=C3F)Cl)C3=N2)OCC1 Chemical compound CN1C[C@H](COC2=NC(N3CC(CC4)NC4C3)=C(C=C(C(C3=CC(O)=CC4=CC=CC=C34)=C3F)Cl)C3=N2)OCC1 IWCQWXMUEKFECE-GZNCHQMQSA-N 0.000 claims 1
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- KAQJRXUDHJIWTJ-MHJFOBGBSA-N CN1[C@H](COC(N=C(C2=CC(Cl)=C3C4=C(C5CC5)C=CC=C4)N4CC(CC5)NC5C4)=NC2=C3F)CCC1 Chemical compound CN1[C@H](COC(N=C(C2=CC(Cl)=C3C4=C(C5CC5)C=CC=C4)N4CC(CC5)NC5C4)=NC2=C3F)CCC1 KAQJRXUDHJIWTJ-MHJFOBGBSA-N 0.000 claims 1
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| JP2024517695A (ja) * | 2021-04-29 | 2024-04-23 | アムジエン・インコーポレーテツド | 複素環式化合物及び使用方法 |
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