TW202208349A - 雜環化合物 - Google Patents

Info

Publication number

TW202208349A

TW202208349A TW110118331A TW110118331A TW202208349A TW 202208349 A TW202208349 A TW 202208349A TW 110118331 A TW110118331 A TW 110118331A TW 110118331 A TW110118331 A TW 110118331A TW 202208349 A TW202208349 A TW 202208349A

Authority

TW

Taiwan

Prior art keywords

methyl

dihydro

ethyl

pyrazol

imidazol

Prior art date

2020-05-22

Links

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• 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 356
• 150000003839 salts Chemical class 0.000 claims abstract description 140
• 238000000034 method Methods 0.000 claims abstract description 66
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 46
• 201000000980 schizophrenia Diseases 0.000 claims abstract description 28
• 208000011117 substance-related disease Diseases 0.000 claims abstract description 24
• 201000010099 disease Diseases 0.000 claims abstract description 21
• 206010013663 drug dependence Diseases 0.000 claims abstract description 19
• 208000019116 sleep disease Diseases 0.000 claims abstract description 19
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 18
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims abstract description 18
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims abstract description 17
• 208000027520 Somatoform disease Diseases 0.000 claims abstract description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims abstract description 16
• 208000027753 pain disease Diseases 0.000 claims abstract description 16
• -1 hexahydropyridyl Chemical group 0.000 claims description 373
• 125000005843 halogen group Chemical group 0.000 claims description 196
• 125000000217 alkyl group Chemical group 0.000 claims description 169
• 125000001424 substituent group Chemical group 0.000 claims description 144
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 139
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 112
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 74
• 125000003118 aryl group Chemical group 0.000 claims description 68
• 125000003545 alkoxy group Chemical group 0.000 claims description 66
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 57
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 55
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 43
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 35
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 34
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 31
• 229940000425 combination drug Drugs 0.000 claims description 27
• 208000035475 disorder Diseases 0.000 claims description 25
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 18
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• 125000002757 morpholinyl group Chemical group 0.000 claims description 14
• 125000002883 imidazolyl group Chemical group 0.000 claims description 11
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
• 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 10
• 150000001412 amines Chemical class 0.000 claims description 9
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 150000002367 halogens Chemical class 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 125000003566 oxetanyl group Chemical group 0.000 claims description 8
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 7
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• DBTILJBQGWZREL-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]imidazol-2-one Chemical group ClC1=CC=CC(N2C(N(CC=3OC(=NN=3)C=3C=CC=CC=3)C=C2)=O)=C1 DBTILJBQGWZREL-UHFFFAOYSA-N 0.000 claims description 5
• 241000282414 Homo sapiens Species 0.000 claims description 5
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
• XAXDFJUJDOTOIJ-CQSZACIVSA-N 1-[(1-ethylpyrazol-4-yl)methyl]-3-[2-fluoro-5-[(2R)-2-methylmorpholin-4-yl]-3-(trifluoromethyl)phenyl]imidazol-2-one Chemical compound CCN1N=CC(CN(C=CN2C(C=C(C=C3C(F)(F)F)N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 XAXDFJUJDOTOIJ-CQSZACIVSA-N 0.000 claims description 3
• SJTQFVAPIUAAIK-UHFFFAOYSA-N 1-[(1-ethylpyrazol-4-yl)methyl]-3-[3-(4-fluorophenyl)-5-(trifluoromethyl)phenyl]imidazol-2-one Chemical compound CCN1N=CC(CN(C=CN2C3=CC(C(F)(F)F)=CC(C(C=C4)=CC=C4F)=C3)C2=O)=C1 SJTQFVAPIUAAIK-UHFFFAOYSA-N 0.000 claims description 3
• PTDQOQLOADMZKN-CQSZACIVSA-N 1-[(1-ethylpyrazol-4-yl)methyl]-4,5-dimethyl-3-[6-[(2R)-2-methylmorpholin-4-yl]-4-(trifluoromethyl)pyridin-2-yl]imidazol-2-one Chemical compound CCN1N=CC(CN(C(C)=C(C)N2C3=NC(N4C[C@@H](C)OCC4)=CC(C(F)(F)F)=C3)C2=O)=C1 PTDQOQLOADMZKN-CQSZACIVSA-N 0.000 claims description 3
• QIBFSGGCSRKTQC-CQSZACIVSA-N 2-[2-fluoro-5-[(2R)-2-methylmorpholin-4-yl]-3-(trifluoromethyl)phenyl]-5-methyl-4-[(1-propan-2-ylpyrazol-4-yl)methyl]-1,2,4-triazol-3-one Chemical compound CC(C)N1N=CC(CN(C(C)=NN2C(C=C(C=C3C(F)(F)F)N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 QIBFSGGCSRKTQC-CQSZACIVSA-N 0.000 claims description 3
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 3
• BEZUOXKMILDUCK-CYBMUJFWSA-N CCN1N=CC(CN(C=CN2C3=NC(N4C[C@@H](C)OCC4)=CC(C(F)(F)F)=C3F)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=CN2C3=NC(N4C[C@@H](C)OCC4)=CC(C(F)(F)F)=C3F)C2=O)=C1 BEZUOXKMILDUCK-CYBMUJFWSA-N 0.000 claims description 2
• GPCDGGKVBPVZCT-UHFFFAOYSA-N 1,1-difluorocyclopropane Chemical compound FC1(F)CC1 GPCDGGKVBPVZCT-UHFFFAOYSA-N 0.000 claims 1
• ICJIONQTABLRER-GFCCVEGCSA-N 3-[(1-ethylpyrazol-4-yl)methyl]-1-[3-fluoro-6-[(2R)-2-methylmorpholin-4-yl]-4-(trifluoromethyl)pyridin-2-yl]-4-(trifluoromethyl)imidazol-2-one Chemical compound CCN1N=CC(CN(C(C(F)(F)F)=CN2C3=NC(N4C[C@@H](C)OCC4)=CC(C(F)(F)F)=C3F)C2=O)=C1 ICJIONQTABLRER-GFCCVEGCSA-N 0.000 claims 1
• NXCVXEUNAHTSMO-CQSZACIVSA-N 3-[(1-ethylpyrazol-4-yl)methyl]-1-[3-fluoro-6-[(2R)-2-methylmorpholin-4-yl]-4-(trifluoromethyl)pyridin-2-yl]-4-methylimidazol-2-one Chemical compound CCN1N=CC(CN(C(C)=CN2C3=NC(N4C[C@@H](C)OCC4)=CC(C(F)(F)F)=C3F)C2=O)=C1 NXCVXEUNAHTSMO-CQSZACIVSA-N 0.000 claims 1
• QJYOBVFCDJDSMK-UHFFFAOYSA-N 3-[4-(2,2-dimethylmorpholin-4-yl)-6-(trifluoromethyl)pyrimidin-2-yl]-1-[(1-ethylpyrazol-4-yl)methyl]-4-methylimidazol-2-one Chemical compound CCN1N=CC(CN(C=C(C)N2C3=NC(C(F)(F)F)=CC(N4CC(C)(C)OCC4)=N3)C2=O)=C1 QJYOBVFCDJDSMK-UHFFFAOYSA-N 0.000 claims 1
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• WQTMWENLHUFFJA-MRXNPFEDSA-N CC(C)N1N=CC(CN(C(C)=CN2C(C=C(C=C3C(F)F)N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 Chemical compound CC(C)N1N=CC(CN(C(C)=CN2C(C=C(C=C3C(F)F)N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 WQTMWENLHUFFJA-MRXNPFEDSA-N 0.000 claims 1
• KZHPDRBUMRTRRD-GOSISDBHSA-N CC(C)N1N=CC(CN(C(C)=CN2C(C=C(C=C3C)N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 Chemical compound CC(C)N1N=CC(CN(C(C)=CN2C(C=C(C=C3C)N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 KZHPDRBUMRTRRD-GOSISDBHSA-N 0.000 claims 1
• RSKFYAYZCFXGGX-OAHLLOKOSA-N CC(C)N1N=CC(CN(C(C)=CN2C3=NC(N4C[C@@H](C)OCC4)=CC(C(F)(F)F)=C3Cl)C2=O)=C1 Chemical compound CC(C)N1N=CC(CN(C(C)=CN2C3=NC(N4C[C@@H](C)OCC4)=CC(C(F)(F)F)=C3Cl)C2=O)=C1 RSKFYAYZCFXGGX-OAHLLOKOSA-N 0.000 claims 1
• IPJLSRQXEUAGME-OAHLLOKOSA-N CC(C)N1N=CC(CN(C(C)=CN2C3=NC(N4C[C@@H](C)OCC4)=CC(C(F)(F)F)=C3F)C2=O)=C1 Chemical compound CC(C)N1N=CC(CN(C(C)=CN2C3=NC(N4C[C@@H](C)OCC4)=CC(C(F)(F)F)=C3F)C2=O)=C1 IPJLSRQXEUAGME-OAHLLOKOSA-N 0.000 claims 1
• QIBFSGGCSRKTQC-AWEZNQCLSA-N CC(C)N1N=CC(CN(C(C)=NN2C(C=C(C=C3C(F)(F)F)N4C[C@H](C)OCC4)=C3F)C2=O)=C1 Chemical compound CC(C)N1N=CC(CN(C(C)=NN2C(C=C(C=C3C(F)(F)F)N4C[C@H](C)OCC4)=C3F)C2=O)=C1 QIBFSGGCSRKTQC-AWEZNQCLSA-N 0.000 claims 1
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• OSLAATJKJDTFSG-QGZVFWFLSA-N CCN1N=CC(CN(C(C)=CN2C(C=C(C=C3C4CC4)N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 Chemical compound CCN1N=CC(CN(C(C)=CN2C(C=C(C=C3C4CC4)N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 OSLAATJKJDTFSG-QGZVFWFLSA-N 0.000 claims 1
• YRNMZVVECOUSFQ-UHFFFAOYSA-N CCN1N=CC(CN(C(C)=CN2C(C=C(C=C3Cl)N4CC(C)(C)OCC4)=C3F)C2=O)=C1 Chemical compound CCN1N=CC(CN(C(C)=CN2C(C=C(C=C3Cl)N4CC(C)(C)OCC4)=C3F)C2=O)=C1 YRNMZVVECOUSFQ-UHFFFAOYSA-N 0.000 claims 1
• SPTCMVWIVPDLNM-OAHLLOKOSA-N CCN1N=CC(CN(C(C)=CN2C(C=C(C=C3Cl)N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 Chemical compound CCN1N=CC(CN(C(C)=CN2C(C=C(C=C3Cl)N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 SPTCMVWIVPDLNM-OAHLLOKOSA-N 0.000 claims 1
• INRKSVUPFDJZTF-MRXNPFEDSA-N CCN1N=CC(CN(C(C)=CN2C(C=C(C=C3OCC(F)(F)F)N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 Chemical compound CCN1N=CC(CN(C(C)=CN2C(C=C(C=C3OCC(F)(F)F)N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 INRKSVUPFDJZTF-MRXNPFEDSA-N 0.000 claims 1
• NUEZCSRJCUOOAY-MRXNPFEDSA-N CCN1N=CC(CN(C(C)=CN2C3=C(C)C(C(F)(F)F)=CC(N4C[C@@H](C)OCC4)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C(C)=CN2C3=C(C)C(C(F)(F)F)=CC(N4C[C@@H](C)OCC4)=C3)C2=O)=C1 NUEZCSRJCUOOAY-MRXNPFEDSA-N 0.000 claims 1
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• CEDLBOXOYVHYPY-CQSZACIVSA-N CCN1N=CC(CN(C(C)=CN2C3=NC(N4C[C@@H](C)OCC4)=CC(C(F)(F)F)=C3Cl)C2=O)=C1 Chemical compound CCN1N=CC(CN(C(C)=CN2C3=NC(N4C[C@@H](C)OCC4)=CC(C(F)(F)F)=C3Cl)C2=O)=C1 CEDLBOXOYVHYPY-CQSZACIVSA-N 0.000 claims 1
• DTTSIRUOKRIZHM-UHFFFAOYSA-N CCN1N=CC(CN(C(C)=NN2C(C=C(C=C3C(F)(F)F)N(C)C4CCOCC4)=C3F)C2=O)=C1 Chemical compound CCN1N=CC(CN(C(C)=NN2C(C=C(C=C3C(F)(F)F)N(C)C4CCOCC4)=C3F)C2=O)=C1 DTTSIRUOKRIZHM-UHFFFAOYSA-N 0.000 claims 1
• NXBSURRSYNBRLB-UHFFFAOYSA-N CCN1N=CC(CN(C(C)=NN2C(C=C(C=C3C(F)(F)F)N(CC4)CCC4(F)F)=C3F)C2=O)=C1 Chemical compound CCN1N=CC(CN(C(C)=NN2C(C=C(C=C3C(F)(F)F)N(CC4)CCC4(F)F)=C3F)C2=O)=C1 NXBSURRSYNBRLB-UHFFFAOYSA-N 0.000 claims 1
• ALWIFUUDYZQGNX-UHFFFAOYSA-N CCN1N=CC(CN(C(C)=NN2C(C=C(C=C3C(F)(F)F)N4CC(C)(C)OCC4)=C3F)C2=O)=C1 Chemical compound CCN1N=CC(CN(C(C)=NN2C(C=C(C=C3C(F)(F)F)N4CC(C)(C)OCC4)=C3F)C2=O)=C1 ALWIFUUDYZQGNX-UHFFFAOYSA-N 0.000 claims 1
• GFCGCFULVPUXED-UHFFFAOYSA-N CCN1N=CC(CN(C(C)=NN2C(C=C3C(F)(F)F)=NC(N(CC4)CCC4(F)F)=C3F)C2=O)=C1 Chemical compound CCN1N=CC(CN(C(C)=NN2C(C=C3C(F)(F)F)=NC(N(CC4)CCC4(F)F)=C3F)C2=O)=C1 GFCGCFULVPUXED-UHFFFAOYSA-N 0.000 claims 1
• IZMXKUOMTGERJG-UHFFFAOYSA-N CCN1N=CC(CN(C(C)=NN2C3=C(C)C(C(F)(F)F)=CC(N(CC4)CCC4(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C(C)=NN2C3=C(C)C(C(F)(F)F)=CC(N(CC4)CCC4(F)F)=C3)C2=O)=C1 IZMXKUOMTGERJG-UHFFFAOYSA-N 0.000 claims 1
• LNKSXVVRBPVDAX-UHFFFAOYSA-N CCN1N=CC(CN(C(C)=NN2C3=NC(N(CC4)CCC4(F)F)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C(C)=NN2C3=NC(N(CC4)CCC4(F)F)=CC(C(F)(F)F)=C3)C2=O)=C1 LNKSXVVRBPVDAX-UHFFFAOYSA-N 0.000 claims 1
• SAPCWPBGRAGVJA-GFCCVEGCSA-N CCN1N=CC(CN(C2=O)C(Cl)=NN2C(C=C(C=C2C(F)(F)F)N3C[C@@H](C)OCC3)=C2F)=C1 Chemical compound CCN1N=CC(CN(C2=O)C(Cl)=NN2C(C=C(C=C2C(F)(F)F)N3C[C@@H](C)OCC3)=C2F)=C1 SAPCWPBGRAGVJA-GFCCVEGCSA-N 0.000 claims 1
• YSXNLMJENREXGK-OAHLLOKOSA-N CCN1N=CC(CN(C=C(C)N2C(C=C(C=C3C(F)(F)F)N4C[C@@H](C)OCC4)=C3Cl)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C(C=C(C=C3C(F)(F)F)N4C[C@@H](C)OCC4)=C3Cl)C2=O)=C1 YSXNLMJENREXGK-OAHLLOKOSA-N 0.000 claims 1
• VIUGKFGAJINJPN-INIZCTEOSA-N CCN1N=CC(CN(C=C(C)N2C(C=C(C=C3C(F)(F)F)OC[C@H]4OCCC4)=C3F)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C(C=C(C=C3C(F)(F)F)OC[C@H]4OCCC4)=C3F)C2=O)=C1 VIUGKFGAJINJPN-INIZCTEOSA-N 0.000 claims 1
• HKZHQYOXZWTIMH-CQSZACIVSA-N CCN1N=CC(CN(C=C(C)N2C(C=C3C(F)(F)F)=NC(N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C(C=C3C(F)(F)F)=NC(N4C[C@@H](C)OCC4)=C3F)C2=O)=C1 HKZHQYOXZWTIMH-CQSZACIVSA-N 0.000 claims 1
• DCNJGVNAZXUKCR-QGZVFWFLSA-N CCN1N=CC(CN(C=C(C)N2C(C=C3N4C[C@@H](C)OCC4)=CC(C4CC4)=C3F)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C(C=C3N4C[C@@H](C)OCC4)=CC(C4CC4)=C3F)C2=O)=C1 DCNJGVNAZXUKCR-QGZVFWFLSA-N 0.000 claims 1
• WLDCZJLXYSZZIA-MRXNPFEDSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(Br)=CC(N4C[C@@H](C)OCC4)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(Br)=CC(N4C[C@@H](C)OCC4)=C3)C2=O)=C1 WLDCZJLXYSZZIA-MRXNPFEDSA-N 0.000 claims 1
• DRKCSOUAAVZOCJ-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(Br)=CC(OCC(C4)CC4(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(Br)=CC(OCC(C4)CC4(F)F)=C3)C2=O)=C1 DRKCSOUAAVZOCJ-UHFFFAOYSA-N 0.000 claims 1
• VMSGFTMCFYMLCA-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(C(CC4)CCC4(F)F)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(C(CC4)CCC4(F)F)=CC(C(F)(F)F)=C3)C2=O)=C1 VMSGFTMCFYMLCA-UHFFFAOYSA-N 0.000 claims 1
• SHIBHYQFGJBADY-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(C(F)(F)F)=CC(C(C=C4)=CC=C4F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(C(F)(F)F)=CC(C(C=C4)=CC=C4F)=C3)C2=O)=C1 SHIBHYQFGJBADY-UHFFFAOYSA-N 0.000 claims 1
• FKPXFOSQXXXREP-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(C(F)(F)F)=NN3CCC3CCC3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(C(F)(F)F)=NN3CCC3CCC3)C2=O)=C1 FKPXFOSQXXXREP-UHFFFAOYSA-N 0.000 claims 1
• FWLVHRCJVVCISZ-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(C4CC4)=CC(N4CC(C)(C)OCC4)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(C4CC4)=CC(N4CC(C)(C)OCC4)=C3)C2=O)=C1 FWLVHRCJVVCISZ-UHFFFAOYSA-N 0.000 claims 1
• VVNIVQWMORDCSF-GOSISDBHSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(C4CC4)=CC(N4C[C@@H](C)OCC4)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(C4CC4)=CC(N4C[C@@H](C)OCC4)=C3)C2=O)=C1 VVNIVQWMORDCSF-GOSISDBHSA-N 0.000 claims 1
• GSNHZEQZHNDYDO-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(C4CC4)=CC(OCC(C4)CC4(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(C4CC4)=CC(OCC(C4)CC4(F)F)=C3)C2=O)=C1 GSNHZEQZHNDYDO-UHFFFAOYSA-N 0.000 claims 1
• MJVIMEZHGIPDSP-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(N(C)C4CCOCC4)=CC(OCC(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(N(C)C4CCOCC4)=CC(OCC(F)(F)F)=C3)C2=O)=C1 MJVIMEZHGIPDSP-UHFFFAOYSA-N 0.000 claims 1
• LBNFXYXOYIZCNV-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(N(CC4)CC4(F)F)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(N(CC4)CC4(F)F)=CC(C(F)(F)F)=C3)C2=O)=C1 LBNFXYXOYIZCNV-UHFFFAOYSA-N 0.000 claims 1
• RICPEEAZFOSDJF-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(N(CCO4)CC4(F)F)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(N(CCO4)CC4(F)F)=CC(C(F)(F)F)=C3)C2=O)=C1 RICPEEAZFOSDJF-UHFFFAOYSA-N 0.000 claims 1
• KPVJBZIIVJNHDV-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(N4C=NC(C)=C4)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(N4C=NC(C)=C4)=CC(C(F)(F)F)=C3)C2=O)=C1 KPVJBZIIVJNHDV-UHFFFAOYSA-N 0.000 claims 1
• FWMGDFBYLDXFIK-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(N4CC(C)(C)OCC4)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(N4CC(C)(C)OCC4)=CC(C(F)(F)F)=C3)C2=O)=C1 FWMGDFBYLDXFIK-UHFFFAOYSA-N 0.000 claims 1
• FMSUTYVSTWETGQ-MRXNPFEDSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(N4C[C@@H](C)OCC4)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(N4C[C@@H](C)OCC4)=CC(C(F)(F)F)=C3)C2=O)=C1 FMSUTYVSTWETGQ-MRXNPFEDSA-N 0.000 claims 1
• NUXQDBJPOGMOAH-QGZVFWFLSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(N4C[C@@H](C)OCC4)=CC(OCC(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(N4C[C@@H](C)OCC4)=CC(OCC(F)(F)F)=C3)C2=O)=C1 NUXQDBJPOGMOAH-QGZVFWFLSA-N 0.000 claims 1
• FMSUTYVSTWETGQ-INIZCTEOSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(N4C[C@H](C)OCC4)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(N4C[C@H](C)OCC4)=CC(C(F)(F)F)=C3)C2=O)=C1 FMSUTYVSTWETGQ-INIZCTEOSA-N 0.000 claims 1
• GKXIJQSLWRRZRC-CALCHBBNSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(N4C[C@H](C)O[C@H](C)C4)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(N4C[C@H](C)O[C@H](C)C4)=CC(C(F)(F)F)=C3)C2=O)=C1 GKXIJQSLWRRZRC-CALCHBBNSA-N 0.000 claims 1
• WNFIENZXRFBNDD-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(OC(C=C4)=CC=C4F)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(OC(C=C4)=CC=C4F)=CC(C(F)(F)F)=C3)C2=O)=C1 WNFIENZXRFBNDD-UHFFFAOYSA-N 0.000 claims 1
• CGQIDAJXWIOKLP-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(OC4CCOCC4)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(OC4CCOCC4)=CC(C(F)(F)F)=C3)C2=O)=C1 CGQIDAJXWIOKLP-UHFFFAOYSA-N 0.000 claims 1
• ATJCGVOMHGLPMR-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(OCC(C4)CC4(F)F)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(OCC(C4)CC4(F)F)=CC(C(F)(F)F)=C3)C2=O)=C1 ATJCGVOMHGLPMR-UHFFFAOYSA-N 0.000 claims 1
• SMXOUOODTMNNSC-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(OCC(C4)CC4(F)F)=CC(C(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(OCC(C4)CC4(F)F)=CC(C(F)F)=C3)C2=O)=C1 SMXOUOODTMNNSC-UHFFFAOYSA-N 0.000 claims 1
• WGFHYDLOLFCERT-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(OCC4(CC4)F)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(OCC4(CC4)F)=CC(C(F)(F)F)=C3)C2=O)=C1 WGFHYDLOLFCERT-UHFFFAOYSA-N 0.000 claims 1
• OWUBWOFMGQGLOE-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(OCC4CC4)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(OCC4CC4)=CC(C(F)(F)F)=C3)C2=O)=C1 OWUBWOFMGQGLOE-UHFFFAOYSA-N 0.000 claims 1
• VHWBNUDYUJPYBJ-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=CC(OCC4OCC4)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=CC(OCC4OCC4)=CC(C(F)(F)F)=C3)C2=O)=C1 VHWBNUDYUJPYBJ-UHFFFAOYSA-N 0.000 claims 1
• NIGNLQVQYVAREV-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=NC(N(CCO4)CC4(F)F)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=NC(N(CCO4)CC4(F)F)=CC(C(F)(F)F)=C3)C2=O)=C1 NIGNLQVQYVAREV-UHFFFAOYSA-N 0.000 claims 1
• CGHZOZZOCIYMRB-UHFFFAOYSA-N CCN1N=CC(CN(C=C(C)N2C3=NC(N4CC(C)(C)OCC4)=CC(C(F)(F)F)=C3)C2=O)=C1 Chemical compound CCN1N=CC(CN(C=C(C)N2C3=NC(N4CC(C)(C)OCC4)=CC(C(F)(F)F)=C3)C2=O)=C1 CGHZOZZOCIYMRB-UHFFFAOYSA-N 0.000 claims 1
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