KR20230169967A - Kras g12d 억제제 - Google Patents

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Publication number

KR20230169967A

KR20230169967A KR1020237034229A KR20237034229A KR20230169967A KR 20230169967 A KR20230169967 A KR 20230169967A KR 1020237034229 A KR1020237034229 A KR 1020237034229A KR 20237034229 A KR20237034229 A KR 20237034229A KR 20230169967 A KR20230169967 A KR 20230169967A

Authority

KR

South Korea

Prior art keywords

diazabicyclo

chloro

fluoro

methoxy

octan

Prior art date

2021-03-12

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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• 229940126204 KRAS G12D inhibitor Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 226
• 238000000034 method Methods 0.000 claims abstract description 136
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 57
• 201000011510 cancer Diseases 0.000 claims abstract description 38
• -1 aminoC 1 -C 3 alkyl Chemical group 0.000 claims description 166
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 101
• 150000003839 salts Chemical class 0.000 claims description 81
• 239000001257 hydrogen Substances 0.000 claims description 72
• 229910052739 hydrogen Inorganic materials 0.000 claims description 72
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 66
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 66
• 125000005843 halogen group Chemical group 0.000 claims description 50
• 229920006395 saturated elastomer Polymers 0.000 claims description 49
• 229910052757 nitrogen Inorganic materials 0.000 claims description 47
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
• JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 34
• 239000008194 pharmaceutical composition Substances 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 102200006539 rs121913529 Human genes 0.000 claims description 21
• 238000011282 treatment Methods 0.000 claims description 21
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 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 description 14
• 125000002619 bicyclic group Chemical group 0.000 claims description 14
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 14
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• 230000005764 inhibitory process Effects 0.000 claims description 13
• GGCHPSDSCUUMSN-CYCBOSICSA-N OC1=CC2=CC=CC=C2C(C(C(Cl)=CC(C2=N3)=C(N4CC(CC5)NC5C4)N=C3OC[C@](CCC3)(C4)N3C[C@@H]4F)=C2F)=C1 Chemical compound OC1=CC2=CC=CC=C2C(C(C(Cl)=CC(C2=N3)=C(N4CC(CC5)NC5C4)N=C3OC[C@](CCC3)(C4)N3C[C@@H]4F)=C2F)=C1 GGCHPSDSCUUMSN-CYCBOSICSA-N 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 125000001624 naphthyl group Chemical group 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 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 description 10
• 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 description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• YODMLRHFGATDGU-OGBBLICMSA-N CC1=CC(N)=NC(C(C(Cl)=CC(C2=N3)=C(N4CC(CC5)NC5C4)N=C3OC[C@](CCC3)(C4)N3C[C@@H]4F)=C2F)=C1C(F)(F)F Chemical compound CC1=CC(N)=NC(C(C(Cl)=CC(C2=N3)=C(N4CC(CC5)NC5C4)N=C3OC[C@](CCC3)(C4)N3C[C@@H]4F)=C2F)=C1C(F)(F)F YODMLRHFGATDGU-OGBBLICMSA-N 0.000 claims description 9
• YODMLRHFGATDGU-HREASWFFSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@@](CCC2)(C4)N2C[C@@H]4F)=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@@](CCC2)(C4)N2C[C@@H]4F)=C3Cl)=C1C(F)(F)F YODMLRHFGATDGU-HREASWFFSA-N 0.000 claims description 9
• GGCHPSDSCUUMSN-TXHQIJRFSA-N OC1=CC2=CC=CC=C2C(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@@](CCC2)(C4)N2C[C@@H]4F)=C3Cl)=C1 Chemical compound OC1=CC2=CC=CC=C2C(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@@](CCC2)(C4)N2C[C@@H]4F)=C3Cl)=C1 GGCHPSDSCUUMSN-TXHQIJRFSA-N 0.000 claims description 9
• GGCHPSDSCUUMSN-QZMOXNRDSA-N OC1=CC2=CC=CC=C2C(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@@](CCC2)(C4)N2C[C@H]4F)=C3Cl)=C1 Chemical compound OC1=CC2=CC=CC=C2C(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@@](CCC2)(C4)N2C[C@H]4F)=C3Cl)=C1 GGCHPSDSCUUMSN-QZMOXNRDSA-N 0.000 claims description 9
• GGCHPSDSCUUMSN-CQFOMOQISA-N OC1=CC2=CC=CC=C2C(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@](CCC2)(C4)N2C[C@H]4F)=C3Cl)=C1 Chemical compound OC1=CC2=CC=CC=C2C(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@](CCC2)(C4)N2C[C@H]4F)=C3Cl)=C1 GGCHPSDSCUUMSN-CQFOMOQISA-N 0.000 claims description 9
• 230000035772 mutation Effects 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 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 description 8
• YCCCGRFMPVXJLA-UMPSKINLSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@@](CCC2)(C4)N2CC4(F)F)=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@@](CCC2)(C4)N2CC4(F)F)=C3Cl)=C1C(F)(F)F YCCCGRFMPVXJLA-UMPSKINLSA-N 0.000 claims description 8
• MOGDUEAEEYJHFG-ZUSPRZCVSA-N CCC1=C2C(C(C(F)=C(C(C(N3CC(CC4)NC4C3)=N3)=C4)N=C3OC[C@@](CCC3)(C5)N3C[C@@H]5F)=C4Cl)=CC(O)=CC2=CC=C1 Chemical compound CCC1=C2C(C(C(F)=C(C(C(N3CC(CC4)NC4C3)=N3)=C4)N=C3OC[C@@](CCC3)(C5)N3C[C@@H]5F)=C4Cl)=CC(O)=CC2=CC=C1 MOGDUEAEEYJHFG-ZUSPRZCVSA-N 0.000 claims description 8
• ZEKZXEBVDWNFJA-BDVHYWIUSA-N CCC1=C2C(C(C(F)=C(C(C(N3CC(CC4)NC4C3)=N3)=C4)N=C3OC[C@@](CCC3)(C5)N3C[C@@H]5F)=C4Cl)=CC(O)=CC2=CC=C1F Chemical compound CCC1=C2C(C(C(F)=C(C(C(N3CC(CC4)NC4C3)=N3)=C4)N=C3OC[C@@](CCC3)(C5)N3C[C@@H]5F)=C4Cl)=CC(O)=CC2=CC=C1F ZEKZXEBVDWNFJA-BDVHYWIUSA-N 0.000 claims description 8
• 208000020816 lung neoplasm Diseases 0.000 claims description 8
• 125000002950 monocyclic group Chemical group 0.000 claims description 8
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 7
• 206010009944 Colon cancer Diseases 0.000 claims description 7
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 7
• BRNDOPKVFODKSC-ZLJCVCDCSA-N OC1=CC2=CC=CC(F)=C2C(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@@](CCC2)(C4)N2C[C@@H]4F)=C3Cl)=C1 Chemical compound OC1=CC2=CC=CC(F)=C2C(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@@](CCC2)(C4)N2C[C@@H]4F)=C3Cl)=C1 BRNDOPKVFODKSC-ZLJCVCDCSA-N 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 206010017758 gastric cancer Diseases 0.000 claims description 7
• 201000005202 lung cancer Diseases 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• 201000011549 stomach cancer Diseases 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 229910052717 sulfur Chemical group 0.000 claims description 6
• YODMLRHFGATDGU-NTUVBDFUSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@@](CCC2)(C4)N2C[C@H]4F)=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@@](CCC2)(C4)N2C[C@H]4F)=C3Cl)=C1C(F)(F)F YODMLRHFGATDGU-NTUVBDFUSA-N 0.000 claims description 5
• XNCXEGSQYWPWIY-JSRJAPPDSA-N C[C@H](CN1CCCCC1)OC(N=C(C1=CC(Cl)=C2C3=CC(O)=CC4=CC=CC=C34)N3CC(CC4)NC4C3)=NC1=C2F Chemical compound C[C@H](CN1CCCCC1)OC(N=C(C1=CC(Cl)=C2C3=CC(O)=CC4=CC=CC=C34)N3CC(CC4)NC4C3)=NC1=C2F XNCXEGSQYWPWIY-JSRJAPPDSA-N 0.000 claims description 5
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 5
• UPBZPOWELYYGEX-ABHNRTSZSA-N OC1=CC2=CC=CC=C2C(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@H](CC2)NC2=O)=C3Cl)=C1 Chemical compound OC1=CC2=CC=CC=C2C(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@H](CC2)NC2=O)=C3Cl)=C1 UPBZPOWELYYGEX-ABHNRTSZSA-N 0.000 claims description 5
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 4
• 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 description 4
• 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 description 4
• YODMLRHFGATDGU-IUPXYIQBSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@](CCC2)(C4)N2C[C@H]4F)=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@](CCC2)(C4)N2C[C@H]4F)=C3Cl)=C1C(F)(F)F YODMLRHFGATDGU-IUPXYIQBSA-N 0.000 claims description 4
• MBBLNXZOCYMWNS-JKTFZKSPSA-N CC1=CC(N)=NC(C(C(F)=C(C(C(N2CC(CC3)NC3C2)=N2)=C3)N=C2OC[C@](CCC2)(C4)N2C[C@H]4OC(F)F)=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@](CCC2)(C4)N2C[C@H]4OC(F)F)=C3Cl)=C1C(F)(F)F MBBLNXZOCYMWNS-JKTFZKSPSA-N 0.000 claims description 4
• 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 description 4
• MOGDUEAEEYJHFG-QNPSEEQMSA-N CCC1=CC=CC2=CC(O)=CC(C(C(Cl)=CC(C3=N4)=C(N5CC(CC6)NC6C5)N=C4OC[C@](CCC4)(C5)N4C[C@@H]5F)=C3F)=C12 Chemical compound CCC1=CC=CC2=CC(O)=CC(C(C(Cl)=CC(C3=N4)=C(N5CC(CC6)NC6C5)N=C4OC[C@](CCC4)(C5)N4C[C@@H]5F)=C3F)=C12 MOGDUEAEEYJHFG-QNPSEEQMSA-N 0.000 claims description 4
• JBXLIGQWOKFXDM-VIQWUECVSA-N CN1[C@H](COC(N=C(C2=CC(Cl)=C3C4=CC(O)=CC5=CC=CC=C45)N4C5CNCC4C5)=NC2=C3F)CCC1 Chemical compound CN1[C@H](COC(N=C(C2=CC(Cl)=C3C4=CC(O)=CC5=CC=CC=C45)N4C5CNCC4C5)=NC2=C3F)CCC1 JBXLIGQWOKFXDM-VIQWUECVSA-N 0.000 claims description 4
• GBIWFIDQBVOWHB-MMWGRWSQSA-N C[C@H](C1)CN(C2)[C@@]1(COC(N=C(C1=CC(Cl)=C3C4=C(C(F)(F)F)C(C)=CC(N)=N4)N4CC(CC5)NC5C4)=NC1=C3F)C[C@H]2F Chemical compound C[C@H](C1)CN(C2)[C@@]1(COC(N=C(C1=CC(Cl)=C3C4=C(C(F)(F)F)C(C)=CC(N)=N4)N4CC(CC5)NC5C4)=NC1=C3F)C[C@H]2F GBIWFIDQBVOWHB-MMWGRWSQSA-N 0.000 claims description 4
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 4
• 201000002528 pancreatic cancer Diseases 0.000 claims description 4
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
• 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 description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 239000011593 sulfur Chemical group 0.000 claims description 3
• SQLHPBJYHIXFHZ-OHAKLNMTSA-N 4-[4-(3,8-diazabicyclo[3.2.1]octan-3-yl)-8-fluoro-2-[[(2R,8S)-2-fluoro-1,2,3,5,6,7-hexahydropyrrolizin-8-yl]methoxy]quinazolin-7-yl]-5-ethynyl-6-fluoronaphthalen-2-ol Chemical compound C#CC(C(C(C(C=CC(C1=N2)=C(N3CC(CC4)NC4C3)N=C2OC[C@](CCC2)(C3)N2C[C@@H]3F)=C1F)=C1)=C(C=C2)C=C1O)=C2F SQLHPBJYHIXFHZ-OHAKLNMTSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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