JPWO2020216766A5 - - Google Patents
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- Publication number
- JPWO2020216766A5 JPWO2020216766A5 JP2021562988A JP2021562988A JPWO2020216766A5 JP WO2020216766 A5 JPWO2020216766 A5 JP WO2020216766A5 JP 2021562988 A JP2021562988 A JP 2021562988A JP 2021562988 A JP2021562988 A JP 2021562988A JP WO2020216766 A5 JPWO2020216766 A5 JP WO2020216766A5
- Authority
- JP
- Japan
- Prior art keywords
- acetamide
- chloro
- fluorophenoxy
- piperidin
- oxadiazol
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 49
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 40
- 150000003839 salts Chemical class 0.000 claims 31
- 239000012453 solvate Substances 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 29
- 229910052736 halogen Inorganic materials 0.000 claims 28
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 19
- 150000002367 halogens Chemical class 0.000 claims 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 229910052799 carbon Inorganic materials 0.000 claims 15
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 10
- 150000004677 hydrates Chemical class 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- -1 pyrimidazyl Chemical group 0.000 claims 5
- FQFOMCJEGOBBCJ-UHFFFAOYSA-N 2-(4-chloro-3-fluorophenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(Cl)C(F)=C1 FQFOMCJEGOBBCJ-UHFFFAOYSA-N 0.000 claims 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- NOKKKQZRRPGELH-SJORKVTESA-N C1C[C@H](C(=O)N[C@@H]1C2=NN=C(O2)C3=CC=C(C=C3)Cl)NC(=O)COC4=CC(=C(C=C4)Cl)F Chemical compound C1C[C@H](C(=O)N[C@@H]1C2=NN=C(O2)C3=CC=C(C=C3)Cl)NC(=O)COC4=CC(=C(C=C4)Cl)F NOKKKQZRRPGELH-SJORKVTESA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- WIISPLMHZMXWCP-XVGQJIODSA-N (2R)-2-(4-chlorophenoxy)-N-[(3S,6R)-6-[5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]piperidin-3-yl]propanamide Chemical compound C[C@H](C(N[C@@H](CC1)CN[C@H]1C1=NN=C(C2=CC=C(C(F)(F)F)C=C2)O1)=O)OC(C=C1)=CC=C1Cl WIISPLMHZMXWCP-XVGQJIODSA-N 0.000 claims 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- ALPGFNSRMFDGPW-TVQRCGJNSA-N 2-(3,4,5-trichlorophenoxy)-N-[(3S,6R)-6-[5-(3,3,3-trifluoropropoxy)-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC(C=C1Cl)=CC(Cl)=C1Cl)N[C@@H](CC1)CN[C@H]1C1=NN=C(OCCC(F)(F)F)O1 ALPGFNSRMFDGPW-TVQRCGJNSA-N 0.000 claims 1
- OGNXWZUHHHSLCV-TVQRCGJNSA-N 2-(4-chloro-3-fluorophenoxy)-2,2-difluoro-N-[(3S,6R)-6-[5-(3,3,3-trifluoropropoxy)-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(C(OC(C=C1)=CC(F)=C1Cl)(F)F)N[C@@H](CC1)CN[C@H]1C1=NN=C(OCCC(F)(F)F)O1 OGNXWZUHHHSLCV-TVQRCGJNSA-N 0.000 claims 1
- PULKXFRRROWQNZ-BEFAXECRSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3R,6S)-6-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]-1-methylpiperidin-3-yl]acetamide Chemical compound CN(C[C@@H](CC1)NC(COC(C=C2)=CC(F)=C2Cl)=O)[C@@H]1C1=NN=C(C(C=C2)=CC=C2Cl)O1 PULKXFRRROWQNZ-BEFAXECRSA-N 0.000 claims 1
- WPGMYLIESAIOHF-YGRLFVJLSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3R,6S)-6-[5-[2-(trifluoromethoxy)ethoxy]-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC(C=C1)=CC(F)=C1Cl)N[C@H](CC1)CN[C@@H]1C1=NN=C(OCCOC(F)(F)F)O1 WPGMYLIESAIOHF-YGRLFVJLSA-N 0.000 claims 1
- FSEBBCDJABZDHH-TVQRCGJNSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3S,6R)-6-[5-(2,2,3,3,3-pentafluoropropoxy)-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound ClC1=C(C=C(OCC(=O)N[C@@H]2CN[C@H](CC2)C=2OC(=NN=2)OCC(C(F)(F)F)(F)F)C=C1)F FSEBBCDJABZDHH-TVQRCGJNSA-N 0.000 claims 1
- TWQKTRGPWRFCNJ-SCLBCKFNSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3S,6R)-6-[5-(2-cyclobutyloxyethoxy)-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC(C=C1)=CC(F)=C1Cl)N[C@@H](CC1)CN[C@H]1C1=NN=C(OCCOC2CCC2)O1 TWQKTRGPWRFCNJ-SCLBCKFNSA-N 0.000 claims 1
- KZSHSKRBRWWJHV-XHDPSFHLSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3S,6R)-6-[5-(3,3-difluorobutoxy)-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound CC(CCOC1=NN=C([C@@H](CC2)NC[C@H]2NC(COC(C=C2)=CC(F)=C2Cl)=O)O1)(F)F KZSHSKRBRWWJHV-XHDPSFHLSA-N 0.000 claims 1
- ZSOHWZCOPINDTK-VKCPWKDNSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3S,6R)-6-[5-(3,3-difluorocyclopentyl)oxy-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC(C=C1)=CC(F)=C1Cl)N[C@@H](CC1)CN[C@H]1C1=NN=C(OC(CC2)CC2(F)F)O1 ZSOHWZCOPINDTK-VKCPWKDNSA-N 0.000 claims 1
- XKBLBXWXNVXMIH-KBXCAEBGSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3S,6R)-6-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC(C=C1)=CC(F)=C1Cl)N[C@@H](CC1)CN[C@H]1C1=NN=C(C(C=C2)=CC=C2Cl)O1 XKBLBXWXNVXMIH-KBXCAEBGSA-N 0.000 claims 1
- WGAZXWHIGMPDKU-OZGRPGILSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3S,6R)-6-[5-[(2,2-difluorocyclobutyl)methoxy]-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC(C=C1)=CC(F)=C1Cl)N[C@@H](CC1)CN[C@H]1C1=NN=C(OCC(CC2)C2(F)F)O1 WGAZXWHIGMPDKU-OZGRPGILSA-N 0.000 claims 1
- PIZPYYFBQDYEMQ-DETPVDSQSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3S,6R)-6-[5-[(3S)-3-(trifluoromethoxy)pyrrolidin-1-yl]-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC(C=C1)=CC(F)=C1Cl)N[C@@H](CC1)CN[C@H]1C1=NN=C(N(CC2)C[C@H]2OC(F)(F)F)O1 PIZPYYFBQDYEMQ-DETPVDSQSA-N 0.000 claims 1
- WKDZVBCFLDPTFU-IUIKQTSFSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3S,6R)-6-[5-[2-[(1R)-2,2-difluorocyclopropyl]oxyethoxy]-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC(C=C1)=CC(F)=C1Cl)N[C@@H](CC1)CN[C@H]1C1=NN=C(OCCO[C@H](C2)C2(F)F)O1 WKDZVBCFLDPTFU-IUIKQTSFSA-N 0.000 claims 1
- WKDZVBCFLDPTFU-XZJROXQQSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3S,6R)-6-[5-[2-[(1S)-2,2-difluorocyclopropyl]oxyethoxy]-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC(C=C1)=CC(F)=C1Cl)N[C@@H](CC1)CN[C@H]1C1=NN=C(OCCO[C@@H](C2)C2(F)F)O1 WKDZVBCFLDPTFU-XZJROXQQSA-N 0.000 claims 1
- PIZPYYFBQDYEMQ-VKCPWKDNSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3S,6R)-6-[5-[3-(trifluoromethoxy)pyrrolidin-1-yl]-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC(C=C1)=CC(F)=C1Cl)N[C@@H](CC1)CN[C@H]1C1=NN=C(N(CC2)CC2OC(F)(F)F)O1 PIZPYYFBQDYEMQ-VKCPWKDNSA-N 0.000 claims 1
- PFSAKJSOWFMJPX-XHDPSFHLSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3S,6R)-6-[5-[3-(trifluoromethyl)azetidin-1-yl]-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC(C=C1)=CC(F)=C1Cl)N[C@@H](CC1)CN[C@H]1C1=NN=C(N(C2)CC2C(F)(F)F)O1 PFSAKJSOWFMJPX-XHDPSFHLSA-N 0.000 claims 1
- DXOBLZMPKMCIDW-KBXCAEBGSA-N 2-(4-chloro-3-fluorophenoxy)-N-[(3S,6R)-6-[5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC(C=C1)=CC(F)=C1Cl)N[C@@H](CC1)CN[C@H]1C1=NN=C(C2=CC=C(C(F)(F)F)C=C2)O1 DXOBLZMPKMCIDW-KBXCAEBGSA-N 0.000 claims 1
- IZQQKPVKARCSQM-SWLSCSKDSA-N 2-(4-chloro-3-methylphenoxy)-N-[(3S,6R)-6-[5-[2-(trifluoromethoxy)ethoxy]-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound CC(C=C(C=C1)OCC(N[C@@H](CC2)CN[C@H]2C2=NN=C(OCCOC(F)(F)F)O2)=O)=C1Cl IZQQKPVKARCSQM-SWLSCSKDSA-N 0.000 claims 1
- GLBNTBLOLXXOFK-UHFFFAOYSA-N 2-(4-chlorophenoxy)propanamide Chemical compound NC(=O)C(C)OC1=CC=C(Cl)C=C1 GLBNTBLOLXXOFK-UHFFFAOYSA-N 0.000 claims 1
- DMCRCFXRBCLJMV-GXTWGEPZSA-N 2-[3-(trifluoromethyl)phenoxy]-N-[(3S,6R)-6-[5-(3,3,3-trifluoropropoxy)-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC1=CC(C(F)(F)F)=CC=C1)N[C@@H](CC1)CN[C@H]1C1=NN=C(OCCC(F)(F)F)O1 DMCRCFXRBCLJMV-GXTWGEPZSA-N 0.000 claims 1
- VMJMSEIKSJEVKU-IINYFYTJSA-N 2-[3-chloro-4-(trifluoromethyl)phenoxy]-N-[(3S,6R)-6-[5-(3,3,3-trifluoropropoxy)-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC1=CC(Cl)=C(C(F)(F)F)C=C1)N[C@@H](CC1)CN[C@H]1C1=NN=C(OCCC(F)(F)F)O1 VMJMSEIKSJEVKU-IINYFYTJSA-N 0.000 claims 1
- MHXCSXYIOJUXKP-IINYFYTJSA-N 2-[3-fluoro-4-(trifluoromethyl)phenoxy]-N-[(3S,6R)-6-[5-(3,3,3-trifluoropropoxy)-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound O=C(COC1=CC(F)=C(C(F)(F)F)C=C1)N[C@@H](CC1)CN[C@H]1C1=NN=C(OCCC(F)(F)F)O1 MHXCSXYIOJUXKP-IINYFYTJSA-N 0.000 claims 1
- QVMJRXVVKHMFGG-IINYFYTJSA-N 2-[4-chloro-3-(difluoromethyl)phenoxy]-N-[(3S,6R)-6-[5-[2-(trifluoromethoxy)ethoxy]-1,3,4-oxadiazol-2-yl]piperidin-3-yl]acetamide Chemical compound C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)C(F)F)C3=NN=C(O3)OCCOC(F)(F)F QVMJRXVVKHMFGG-IINYFYTJSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- NOKKKQZRRPGELH-DLBZAZTESA-N C1C[C@@H](C(=O)N[C@H]1C2=NN=C(O2)C3=CC=C(C=C3)Cl)NC(=O)COC4=CC(=C(C=C4)Cl)F Chemical compound C1C[C@@H](C(=O)N[C@H]1C2=NN=C(O2)C3=CC=C(C=C3)Cl)NC(=O)COC4=CC(=C(C=C4)Cl)F NOKKKQZRRPGELH-DLBZAZTESA-N 0.000 claims 1
- XKBLBXWXNVXMIH-RDTXWAMCSA-N C1C[C@@H](NC[C@@H]1NC(=O)COC2=CC(=C(C=C2)Cl)F)C3=NN=C(O3)C4=CC=C(C=C4)Cl Chemical compound C1C[C@@H](NC[C@@H]1NC(=O)COC2=CC(=C(C=C2)Cl)F)C3=NN=C(O3)C4=CC=C(C=C4)Cl XKBLBXWXNVXMIH-RDTXWAMCSA-N 0.000 claims 1
- HHKCWYQUTALZKS-GXSJLCMTSA-N C1C[C@@H](NC[C@H]1NC(=O)COC2=C(C(=C(C=C2)Cl)F)F)C3=NN=C(O3)OCCC(F)(F)F Chemical compound C1C[C@@H](NC[C@H]1NC(=O)COC2=C(C(=C(C=C2)Cl)F)F)C3=NN=C(O3)OCCC(F)(F)F HHKCWYQUTALZKS-GXSJLCMTSA-N 0.000 claims 1
- UCEOETVIOHGDBL-TVQRCGJNSA-N C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C(=C2)F)Cl)F)C3=NN=C(O3)OCCC(F)(F)F Chemical compound C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C(=C2)F)Cl)F)C3=NN=C(O3)OCCC(F)(F)F UCEOETVIOHGDBL-TVQRCGJNSA-N 0.000 claims 1
- ROQYVPFPMILBBR-IINYFYTJSA-N C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)C(F)F)Cl)C3=NN=C(O3)OCCOC(F)(F)F Chemical compound C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)C(F)F)Cl)C3=NN=C(O3)OCCOC(F)(F)F ROQYVPFPMILBBR-IINYFYTJSA-N 0.000 claims 1
- QCTKMXZSWWGNJQ-SWLSCSKDSA-N C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)C#N)C3=NN=C(O3)OCCOC(F)(F)F Chemical compound C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)C#N)C3=NN=C(O3)OCCOC(F)(F)F QCTKMXZSWWGNJQ-SWLSCSKDSA-N 0.000 claims 1
- XBBJACHSOVIHIV-IINYFYTJSA-N C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)Cl)C3=NN=C(O3)OCCC(F)(F)F Chemical compound C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)Cl)C3=NN=C(O3)OCCC(F)(F)F XBBJACHSOVIHIV-IINYFYTJSA-N 0.000 claims 1
- ULNPOBOKUAWLSL-YVEFUNNKSA-N C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)Cl)C3=NN=C(O3)OCCOC4CC4 Chemical compound C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)Cl)C3=NN=C(O3)OCCOC4CC4 ULNPOBOKUAWLSL-YVEFUNNKSA-N 0.000 claims 1
- HCQDCRJTPXPCPV-KPZWWZAWSA-N C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)F)C3=NN=C(O3)C4=CC(=C(C=C4)Cl)F Chemical compound C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)F)C3=NN=C(O3)C4=CC(=C(C=C4)Cl)F HCQDCRJTPXPCPV-KPZWWZAWSA-N 0.000 claims 1
- LVAMXBFNHDQITO-BLLLJJGKSA-N C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)F)C3=NN=C(O3)C4=CN=C(C=C4)C(F)(F)F Chemical compound C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)F)C3=NN=C(O3)C4=CN=C(C=C4)C(F)(F)F LVAMXBFNHDQITO-BLLLJJGKSA-N 0.000 claims 1
- XWIUTTKPDFGIFI-QSYLOLMPSA-N C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)F)C3=NN=C(O3)C4CC(C4)OC5CC5 Chemical compound C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)F)C3=NN=C(O3)C4CC(C4)OC5CC5 XWIUTTKPDFGIFI-QSYLOLMPSA-N 0.000 claims 1
- HFKOVTBFVIXOLK-BLLLJJGKSA-N C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)F)C3=NN=C(O3)C4CN(C4)CC(F)(F)F Chemical compound C1C[C@@H](NC[C@H]1NC(=O)COC2=CC(=C(C=C2)Cl)F)C3=NN=C(O3)C4CN(C4)CC(F)(F)F HFKOVTBFVIXOLK-BLLLJJGKSA-N 0.000 claims 1
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