CA2886885C - Pde9i with imidazo pyrazinone backbone - Google Patents

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Publication number

CA2886885C

CA2886885C CA2886885A CA2886885A CA2886885C CA 2886885 C CA2886885 C CA 2886885C CA 2886885 A CA2886885 A CA 2886885A CA 2886885 A CA2886885 A CA 2886885A CA 2886885 C CA2886885 C CA 2886885C

Authority

CA

Canada

Prior art keywords

imidazo

pyrazin

compound

pharmaceutically acceptable

acid addition

Prior art date

2011-10-10

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.)

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• MPWOBEOETVOESI-UHFFFAOYSA-N imidazo[4,5-b]pyrazin-2-one Chemical group N1=CC=NC2=NC(=O)N=C21 MPWOBEOETVOESI-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 236
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 239000003937 drug carrier Substances 0.000 claims abstract description 9
• 238000002360 preparation method Methods 0.000 claims abstract description 8
• 150000003839 salts Chemical class 0.000 claims description 146
• 239000002253 acid Substances 0.000 claims description 140
• -1 branched C3-C6 alkyl Chemical group 0.000 claims description 94
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
• 239000000203 mixture Substances 0.000 claims description 27
• 229910052731 fluorine Inorganic materials 0.000 claims description 23
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
• 208000024827 Alzheimer disease Diseases 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
• ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 208000011963 Substance-induced psychotic disease Diseases 0.000 claims description 12
• 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims description 12
• 239000003085 diluting agent Substances 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 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
• 238000007363 ring formation reaction Methods 0.000 claims description 10
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 9
• 230000007000 age related cognitive decline Effects 0.000 claims description 9
• 125000004104 aryloxy group Chemical group 0.000 claims description 9
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 7
• 241000218236 Cannabis Species 0.000 claims description 7
• 208000036626 Mental retardation Diseases 0.000 claims description 7
• 208000028017 Psychotic disease Diseases 0.000 claims description 7
• 229940025084 amphetamine Drugs 0.000 claims description 7
• 229960003920 cocaine Drugs 0.000 claims description 7
• 239000000380 hallucinogen Substances 0.000 claims description 7
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
• 229940005483 opioid analgesics Drugs 0.000 claims description 7
• JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims description 7
• 229950010883 phencyclidine Drugs 0.000 claims description 7
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 239000001257 hydrogen Substances 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 229910052757 nitrogen Inorganic materials 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• FQTKUALMFWAFOT-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[(3-pyrimidin-2-ylazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)C=3N=CC=CN=3)=CN12 FQTKUALMFWAFOT-UHFFFAOYSA-N 0.000 claims description 2
• UIIQLHYXQBZHDU-UHFFFAOYSA-N 3-phenyl-6-[(3-phenylazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1CN(C1)CC1C1=CC=CC=C1 UIIQLHYXQBZHDU-UHFFFAOYSA-N 0.000 claims description 2
• OZWPMNOQMHSJRL-UHFFFAOYSA-N 3-phenyl-6-[(3-quinoxalin-2-yloxyazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound N=1C=C2C(=O)NC(CN3CC(C3)OC=3N=C4C=CC=CC4=NC=3)=CN2C=1C1=CC=CC=C1 OZWPMNOQMHSJRL-UHFFFAOYSA-N 0.000 claims description 2
• MNFIXJUASSBZOW-UHFFFAOYSA-N 6-[1-(3-methoxyazetidin-1-yl)ethyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(OC)CN1C(C)C(NC1=O)=CN2C1=CN=C2C1=CC=CC=C1 MNFIXJUASSBZOW-UHFFFAOYSA-N 0.000 claims description 2
• DELBVJNCJUYZPV-UHFFFAOYSA-N 6-[[3-(4-fluorophenoxy)azetidin-1-yl]methyl]-3-(oxolan-3-yl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1OC1CN(CC=2NC(=O)C3=CN=C(N3C=2)C2COCC2)C1 DELBVJNCJUYZPV-UHFFFAOYSA-N 0.000 claims description 2
• INLJMCZLCRCGTA-UHFFFAOYSA-N CC(NCC1CCCCC1)c1cn2c(ncc2c(=O)[nH]1)-c1ccccc1 Chemical compound CC(NCC1CCCCC1)c1cn2c(ncc2c(=O)[nH]1)-c1ccccc1 INLJMCZLCRCGTA-UHFFFAOYSA-N 0.000 claims description 2
• BTIGOENJJYHKRQ-UHFFFAOYSA-N CC1CN(Cc2ccccn2)CC1c1cn2c(ncc2c(=O)[nH]1)C1CCOCC1 Chemical compound CC1CN(Cc2ccccn2)CC1c1cn2c(ncc2c(=O)[nH]1)C1CCOCC1 BTIGOENJJYHKRQ-UHFFFAOYSA-N 0.000 claims description 2
• RKEQVUHWOFALPN-UHFFFAOYSA-N O=c1[nH]c(CN2CCC(C2)Oc2ncccn2)cn2c(ncc12)C1CCOCC1 Chemical compound O=c1[nH]c(CN2CCC(C2)Oc2ncccn2)cn2c(ncc12)C1CCOCC1 RKEQVUHWOFALPN-UHFFFAOYSA-N 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• FKZBSXUJAGAAGL-UHFFFAOYSA-N 1-bromo-3-(4-chlorophenyl)-6-[1-[(4-fluorophenyl)methyl]-4-methylpyrrolidin-3-yl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(C=2NC(=O)C3=C(Br)N=C(N3C=2)C=2C=CC(Cl)=CC=2)C(C)CN1CC1=CC=C(F)C=C1 FKZBSXUJAGAAGL-UHFFFAOYSA-N 0.000 claims 1
• LYDLONHBBHMLKV-UHFFFAOYSA-N 1-bromo-3-(4-fluorophenyl)-6-[1-[(4-fluorophenyl)methyl]-4-methylpyrrolidin-3-yl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(C=2NC(=O)C3=C(Br)N=C(N3C=2)C=2C=CC(F)=CC=2)C(C)CN1CC1=CC=C(F)C=C1 LYDLONHBBHMLKV-UHFFFAOYSA-N 0.000 claims 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
• WZEBNPXEWQABBM-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-6-[[3-(4-methoxyphenyl)azetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(OC)=CC=C1C1CN(CC=2NC(=O)C3=CN=C(N3C=2)C=2C=C(F)C=C(F)C=2)C1 WZEBNPXEWQABBM-UHFFFAOYSA-N 0.000 claims 1
• QWXPAEULRAXJME-UHFFFAOYSA-N 3-(4,4-difluorocyclohexyl)-6-[(3-methoxyazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(OC)CN1CC(NC1=O)=CN2C1=CN=C2C1CCC(F)(F)CC1 QWXPAEULRAXJME-UHFFFAOYSA-N 0.000 claims 1
• XEVNPWFTIMDURN-UHFFFAOYSA-N 3-(4,4-difluorocyclohexyl)-6-[[3-(4-methoxyphenyl)azetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(OC)=CC=C1C1CN(CC=2NC(=O)C3=CN=C(N3C=2)C2CCC(F)(F)CC2)C1 XEVNPWFTIMDURN-UHFFFAOYSA-N 0.000 claims 1
• QUVZKCAAXZEUKT-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-[1-[(4-fluorophenyl)methyl]-4-methylpyrrolidin-3-yl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(C=2NC(=O)C3=CN=C(N3C=2)C=2C=CC(Cl)=CC=2)C(C)CN1CC1=CC=C(F)C=C1 QUVZKCAAXZEUKT-UHFFFAOYSA-N 0.000 claims 1
• FXDZYGQOMMBTKL-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[(3-phenoxyazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)OC=3C=CC=CC=3)=CN12 FXDZYGQOMMBTKL-UHFFFAOYSA-N 0.000 claims 1
• YRNHKKWWMGNSJH-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[(3-phenylmethoxyazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)OCC=3C=CC=CC=3)=CN12 YRNHKKWWMGNSJH-UHFFFAOYSA-N 0.000 claims 1
• BJRLUBFRQQIWDK-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[(3-pyrazin-2-yloxyazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)OC=3N=CC=NC=3)=CN12 BJRLUBFRQQIWDK-UHFFFAOYSA-N 0.000 claims 1
• OPPJESMUQLKXLM-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[(3-pyridin-4-yloxyazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)OC=3C=CN=CC=3)=CN12 OPPJESMUQLKXLM-UHFFFAOYSA-N 0.000 claims 1
• KZXQDNGEOOWVOT-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[1-(3-methoxyazetidin-1-yl)ethyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(OC)CN1C(C)C(NC1=O)=CN2C1=CN=C2C1=CC=C(F)C=C1 KZXQDNGEOOWVOT-UHFFFAOYSA-N 0.000 claims 1
• VURKBBXXUCMNNY-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[1-(3-propan-2-yloxyazetidin-1-yl)ethyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(OC(C)C)CN1C(C)C(NC1=O)=CN2C1=CN=C2C1=CC=C(F)C=C1 VURKBBXXUCMNNY-UHFFFAOYSA-N 0.000 claims 1
• IXXFEEXROAIYKE-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[1-[(4-fluorophenyl)methyl]-4-methylpyrrolidin-3-yl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(C=2NC(=O)C3=CN=C(N3C=2)C=2C=CC(F)=CC=2)C(C)CN1CC1=CC=C(F)C=C1 IXXFEEXROAIYKE-UHFFFAOYSA-N 0.000 claims 1
• DECWKGNPLGHKNM-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[1-[3-(4-methoxyphenyl)azetidin-1-yl]ethyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(OC)=CC=C1C1CN(C(C)C=2NC(=O)C3=CN=C(N3C=2)C=2C=CC(F)=CC=2)C1 DECWKGNPLGHKNM-UHFFFAOYSA-N 0.000 claims 1
• QAWRXXWLFINXRI-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[1-[3-[4-(trifluoromethoxy)phenoxy]azetidin-1-yl]ethyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC(F)=CC=3)=NC=C2C(=O)NC=1C(C)N(C1)CC1OC1=CC=C(OC(F)(F)F)C=C1 QAWRXXWLFINXRI-UHFFFAOYSA-N 0.000 claims 1
• KQUHRFKFEIWQQX-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[4-methyl-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(C=2NC(=O)C3=CN=C(N3C=2)C=2C=CC(F)=CC=2)C(C)CN1CC1=CC=CC=N1 KQUHRFKFEIWQQX-UHFFFAOYSA-N 0.000 claims 1
• RQTYTKFUFIQXRT-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[[3-(4-methoxyphenyl)azetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(OC)=CC=C1C1CN(CC=2NC(=O)C3=CN=C(N3C=2)C=2C=CC(F)=CC=2)C1 RQTYTKFUFIQXRT-UHFFFAOYSA-N 0.000 claims 1
• SNADRBGYEUKACC-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[[3-(6-fluoropyridin-2-yl)oxyazetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)OC=3N=C(F)C=CC=3)=CN12 SNADRBGYEUKACC-UHFFFAOYSA-N 0.000 claims 1
• HSTTWGXLTCSUAV-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[[3-[(4-methylphenyl)methoxy]azetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(C)=CC=C1COC1CN(CC=2NC(=O)C3=CN=C(N3C=2)C=2C=CC(F)=CC=2)C1 HSTTWGXLTCSUAV-UHFFFAOYSA-N 0.000 claims 1
• OQOLKOFSTBTOOE-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[[3-[3-(trifluoromethyl)phenoxy]azetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)OC=3C=C(C=CC=3)C(F)(F)F)=CN12 OQOLKOFSTBTOOE-UHFFFAOYSA-N 0.000 claims 1
• ZNSXCMJFEQHEIJ-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[[3-[4-(trifluoromethoxy)phenoxy]azetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)OC=3C=CC(OC(F)(F)F)=CC=3)=CN12 ZNSXCMJFEQHEIJ-UHFFFAOYSA-N 0.000 claims 1
• IINBIGHNJSPNJV-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[[3-[4-(trifluoromethyl)phenoxy]azetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)OC=3C=CC(=CC=3)C(F)(F)F)=CN12 IINBIGHNJSPNJV-UHFFFAOYSA-N 0.000 claims 1
• YGPFNFJRJIKVTN-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[[3-[5-(trifluoromethyl)pyridin-2-yl]azetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)C=3N=CC(=CC=3)C(F)(F)F)=CN12 YGPFNFJRJIKVTN-UHFFFAOYSA-N 0.000 claims 1
• QJJXPKQAVYZNFE-UHFFFAOYSA-N 3-(oxan-4-yl)-6-[(3-phenylmethoxyazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C3CCOCC3)=NC=C2C(=O)NC=1CN(C1)CC1OCC1=CC=CC=C1 QJJXPKQAVYZNFE-UHFFFAOYSA-N 0.000 claims 1
• LOPBTZDZPHWJST-UHFFFAOYSA-N 3-(oxan-4-yl)-6-[(3-pyridin-2-ylazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C3CCOCC3)=NC=C2C(=O)NC=1CN(C1)CC1C1=CC=CC=N1 LOPBTZDZPHWJST-UHFFFAOYSA-N 0.000 claims 1
• RXXATJXJQNATOK-UHFFFAOYSA-N 3-(oxan-4-yl)-6-[(3-pyridin-3-yloxyazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C3CCOCC3)=NC=C2C(=O)NC=1CN(C1)CC1OC1=CC=CN=C1 RXXATJXJQNATOK-UHFFFAOYSA-N 0.000 claims 1
• OOGGVHCCYMTPOH-UHFFFAOYSA-N 3-(oxan-4-yl)-6-[(3-pyridin-4-yloxyazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C3CCOCC3)=NC=C2C(=O)NC=1CN(C1)CC1OC1=CC=NC=C1 OOGGVHCCYMTPOH-UHFFFAOYSA-N 0.000 claims 1
• OGRBWYPMXBRPRY-UHFFFAOYSA-N 3-(oxan-4-yl)-6-[(3-pyrimidin-2-ylazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C3CCOCC3)=NC=C2C(=O)NC=1CN(C1)CC1C1=NC=CC=N1 OGRBWYPMXBRPRY-UHFFFAOYSA-N 0.000 claims 1
• CMBSEKRHRWPVPW-UHFFFAOYSA-N 3-(oxan-4-yl)-6-[(3-quinoxalin-2-yloxyazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound N=1C=C2C(=O)NC(CN3CC(C3)OC=3N=C4C=CC=CC4=NC=3)=CN2C=1C1CCOCC1 CMBSEKRHRWPVPW-UHFFFAOYSA-N 0.000 claims 1
• GTTHSYSZPCCJIU-UHFFFAOYSA-N 3-(oxan-4-yl)-6-[1-(3-propan-2-yloxyazetidin-1-yl)ethyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(OC(C)C)CN1C(C)C(NC1=O)=CN2C1=CN=C2C1CCOCC1 GTTHSYSZPCCJIU-UHFFFAOYSA-N 0.000 claims 1
• QZTPIPQMRYBGTO-UHFFFAOYSA-N 3-(oxan-4-yl)-6-[1-(3-pyrimidin-2-ylazetidin-1-yl)ethyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C3CCOCC3)=NC=C2C(=O)NC=1C(C)N(C1)CC1C1=NC=CC=N1 QZTPIPQMRYBGTO-UHFFFAOYSA-N 0.000 claims 1
• OSQDOVRKWAPFHU-UHFFFAOYSA-N 3-(oxan-4-yl)-6-[[3-[4-(trifluoromethoxy)phenoxy]azetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1OC1CN(CC=2NC(=O)C3=CN=C(N3C=2)C2CCOCC2)C1 OSQDOVRKWAPFHU-UHFFFAOYSA-N 0.000 claims 1
• LRZYGSFLGHBHPG-UHFFFAOYSA-N 3-(oxan-4-yl)-6-[[3-[4-(trifluoromethyl)phenoxy]azetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1CN(CC=2NC(=O)C3=CN=C(N3C=2)C2CCOCC2)C1 LRZYGSFLGHBHPG-UHFFFAOYSA-N 0.000 claims 1
• YDQDHZGQPBYEIM-UHFFFAOYSA-N 3-(oxan-4-yl)-6-[[3-[5-(trifluoromethyl)pyridin-2-yl]azetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound N1=CC(C(F)(F)F)=CC=C1C1CN(CC=2NC(=O)C3=CN=C(N3C=2)C2CCOCC2)C1 YDQDHZGQPBYEIM-UHFFFAOYSA-N 0.000 claims 1
• JLTUWGVEVCFBPL-UHFFFAOYSA-N 3-[1-[[3-(oxan-4-yl)-8-oxo-7h-imidazo[1,5-a]pyrazin-6-yl]methyl]azetidin-3-yl]benzonitrile Chemical compound C=1N2C(C3CCOCC3)=NC=C2C(=O)NC=1CN(C1)CC1C1=CC=CC(C#N)=C1 JLTUWGVEVCFBPL-UHFFFAOYSA-N 0.000 claims 1
• AZESOYDETIJHEG-UHFFFAOYSA-N 3-[1-[[3-(oxan-4-yl)-8-oxo-7h-imidazo[1,5-a]pyrazin-6-yl]methyl]azetidin-3-yl]oxybenzonitrile Chemical compound C=1N2C(C3CCOCC3)=NC=C2C(=O)NC=1CN(C1)CC1OC1=CC=CC(C#N)=C1 AZESOYDETIJHEG-UHFFFAOYSA-N 0.000 claims 1
• WZABYEZKNDXDDU-UHFFFAOYSA-N 3-cyclopentyl-1,5-difluoro-6-[(3-phenylazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound N12C(F)=C(CN3CC(C3)C=3C=CC=CC=3)NC(=O)C2=C(F)N=C1C1CCCC1 WZABYEZKNDXDDU-UHFFFAOYSA-N 0.000 claims 1
• ZAGPQEJVMNDNLB-UHFFFAOYSA-N 3-cyclopentyl-6-[(3-propan-2-yloxyazetidin-1-yl)methyl]-7H-imidazo[1,5-a]pyrazin-8-one Chemical compound CC(C)OC1CN(Cc2cn3c(ncc3c(=O)[nH]2)C2CCCC2)C1 ZAGPQEJVMNDNLB-UHFFFAOYSA-N 0.000 claims 1
• PHAFRDVDJABRRW-UHFFFAOYSA-N 3-cyclopentyl-6-[(3-pyrimidin-2-yloxyazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C3CCCC3)=NC=C2C(=O)NC=1CN(C1)CC1OC1=NC=CC=N1 PHAFRDVDJABRRW-UHFFFAOYSA-N 0.000 claims 1
• HKLDRFWBNHLUBD-UHFFFAOYSA-N 3-cyclopentyl-6-[1-[3-(2-fluorophenoxy)azetidin-1-yl]ethyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C3CCCC3)=NC=C2C(=O)NC=1C(C)N(C1)CC1OC1=CC=CC=C1F HKLDRFWBNHLUBD-UHFFFAOYSA-N 0.000 claims 1
• VNOSHKVXVILZCY-UHFFFAOYSA-N 3-cyclopentyl-6-[1-[3-(4-fluorophenoxy)azetidin-1-yl]ethyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C3CCCC3)=NC=C2C(=O)NC=1C(C)N(C1)CC1OC1=CC=C(F)C=C1 VNOSHKVXVILZCY-UHFFFAOYSA-N 0.000 claims 1
• XXQMDDBSEINMNW-UHFFFAOYSA-N 3-cyclopentyl-6-[1-[3-[4-(dimethylamino)phenyl]azetidin-1-yl]ethyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C3CCCC3)=NC=C2C(=O)NC=1C(C)N(C1)CC1C1=CC=C(N(C)C)C=C1 XXQMDDBSEINMNW-UHFFFAOYSA-N 0.000 claims 1
• WNHFJGLSGWEZST-UHFFFAOYSA-N 3-cyclopentyl-6-[[3-(4-methoxyphenyl)azetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(OC)=CC=C1C1CN(CC=2NC(=O)C3=CN=C(N3C=2)C2CCCC2)C1 WNHFJGLSGWEZST-UHFFFAOYSA-N 0.000 claims 1
• RRPPYCHNHQRJHT-UHFFFAOYSA-N 3-phenyl-6-[(3-pyridin-2-ylazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1CN(C1)CC1C1=CC=CC=N1 RRPPYCHNHQRJHT-UHFFFAOYSA-N 0.000 claims 1
• UJWXNBFXBBWNBN-UHFFFAOYSA-N 3-phenyl-6-[(3-pyrimidin-2-yloxyazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1CN(C1)CC1OC1=NC=CC=N1 UJWXNBFXBBWNBN-UHFFFAOYSA-N 0.000 claims 1
• OLZQZZXWANRKEL-UHFFFAOYSA-N 3-phenyl-6-[1-(3-phenylazetidin-1-yl)ethyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1C(C)N(C1)CC1C1=CC=CC=C1 OLZQZZXWANRKEL-UHFFFAOYSA-N 0.000 claims 1
• OVZDVODUHKIUOZ-UHFFFAOYSA-N 3-phenyl-6-[1-(3-pyrazin-2-yloxyazetidin-1-yl)ethyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1C(C)N(C1)CC1OC1=CN=CC=N1 OVZDVODUHKIUOZ-UHFFFAOYSA-N 0.000 claims 1
• DWJFOZLYWSESSK-UHFFFAOYSA-N 3-phenyl-6-[1-(3-pyrimidin-2-yloxyazetidin-1-yl)ethyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1C(C)N(C1)CC1OC1=NC=CC=N1 DWJFOZLYWSESSK-UHFFFAOYSA-N 0.000 claims 1
• ULUMXHQAJCHOKG-UHFFFAOYSA-N 4-[1-[(8-oxo-3-phenyl-7h-imidazo[1,5-a]pyrazin-6-yl)methyl]azetidin-3-yl]benzonitrile Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1CN(C1)CC1C1=CC=C(C#N)C=C1 ULUMXHQAJCHOKG-UHFFFAOYSA-N 0.000 claims 1
• QADIBBWCJYFYGW-UHFFFAOYSA-N 4-[1-[1-(8-oxo-3-phenyl-7h-imidazo[1,5-a]pyrazin-6-yl)ethyl]azetidin-3-yl]benzonitrile Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1C(C)N(C1)CC1C1=CC=C(C#N)C=C1 QADIBBWCJYFYGW-UHFFFAOYSA-N 0.000 claims 1
• IGMGMJKJKDHVGL-UHFFFAOYSA-N 4-[1-[[3-(4-fluorophenyl)-8-oxo-7h-imidazo[1,5-a]pyrazin-6-yl]methyl]azetidin-3-yl]benzonitrile Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)C=3C=CC(=CC=3)C#N)=CN12 IGMGMJKJKDHVGL-UHFFFAOYSA-N 0.000 claims 1
• NFPOVNWFXRDZCJ-UHFFFAOYSA-N 4-[1-[[3-(4-fluorophenyl)-8-oxo-7h-imidazo[1,5-a]pyrazin-6-yl]methyl]azetidin-3-yl]oxybenzonitrile Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)OC=3C=CC(=CC=3)C#N)=CN12 NFPOVNWFXRDZCJ-UHFFFAOYSA-N 0.000 claims 1
• SIPRQDBEAIFDDW-UHFFFAOYSA-N 4-[1-[[3-(oxan-4-yl)-8-oxo-7h-imidazo[1,5-a]pyrazin-6-yl]methyl]azetidin-3-yl]benzonitrile Chemical compound C=1N2C(C3CCOCC3)=NC=C2C(=O)NC=1CN(C1)CC1C1=CC=C(C#N)C=C1 SIPRQDBEAIFDDW-UHFFFAOYSA-N 0.000 claims 1
• ZUGIXRRIANHPHV-UHFFFAOYSA-N 4-[1-[[3-(oxan-4-yl)-8-oxo-7h-imidazo[1,5-a]pyrazin-6-yl]methyl]azetidin-3-yl]oxybenzonitrile Chemical compound C=1N2C(C3CCOCC3)=NC=C2C(=O)NC=1CN(C1)CC1OC1=CC=C(C#N)C=C1 ZUGIXRRIANHPHV-UHFFFAOYSA-N 0.000 claims 1
• ABTJJKXVCBVRJS-UHFFFAOYSA-N 4-[[3-methyl-4-[3-(oxan-4-yl)-8-oxo-7h-imidazo[1,5-a]pyrazin-6-yl]pyrrolidin-1-yl]methyl]benzonitrile Chemical compound C1C(C=2NC(=O)C3=CN=C(N3C=2)C2CCOCC2)C(C)CN1CC1=CC=C(C#N)C=C1 ABTJJKXVCBVRJS-UHFFFAOYSA-N 0.000 claims 1
• YDZCIMPTHKZBJC-UHFFFAOYSA-N 6-(1-benzyl-4-methylpyrrolidin-3-yl)-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(C=2NC(=O)C3=CN=C(N3C=2)C=2C=CC=CC=2)C(C)CN1CC1=CC=CC=C1 YDZCIMPTHKZBJC-UHFFFAOYSA-N 0.000 claims 1
• QVLJPVCBNMVOLX-UHFFFAOYSA-N 6-[(3-anilinopyrrolidin-1-yl)methyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1CN(C1)CCC1NC1=CC=CC=C1 QVLJPVCBNMVOLX-UHFFFAOYSA-N 0.000 claims 1
• SDQZXGDOJXASJK-UHFFFAOYSA-N 6-[(3-methoxyazetidin-1-yl)-phenylmethyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(OC)CN1C(C=1NC(=O)C2=CN=C(N2C=1)C=1C=CC=CC=1)C1=CC=CC=C1 SDQZXGDOJXASJK-UHFFFAOYSA-N 0.000 claims 1
• UWMJSOJFERDASH-UHFFFAOYSA-N 6-[(3-methoxyazetidin-1-yl)methyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(OC)CN1CC(NC1=O)=CN2C1=CN=C2C1=CC=CC=C1 UWMJSOJFERDASH-UHFFFAOYSA-N 0.000 claims 1
• WMIPWRFZOVGSAJ-UHFFFAOYSA-N 6-[1-(3-phenoxyazetidin-1-yl)ethyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1C(C)N(C1)CC1OC1=CC=CC=C1 WMIPWRFZOVGSAJ-UHFFFAOYSA-N 0.000 claims 1
• YETXWOKSBJELRK-UHFFFAOYSA-N 6-[1-[(4-fluorophenyl)methyl]-4-methylpyrrolidin-3-yl]-3-(oxan-4-yl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(C=2NC(=O)C3=CN=C(N3C=2)C2CCOCC2)C(C)CN1CC1=CC=C(F)C=C1 YETXWOKSBJELRK-UHFFFAOYSA-N 0.000 claims 1
• YDHASVMHQLJMHY-UHFFFAOYSA-N 6-[1-[(4-fluorophenyl)methyl]-4-methylpyrrolidin-3-yl]-3-[4-(trifluoromethoxy)phenyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(C=2NC(=O)C3=CN=C(N3C=2)C=2C=CC(OC(F)(F)F)=CC=2)C(C)CN1CC1=CC=C(F)C=C1 YDHASVMHQLJMHY-UHFFFAOYSA-N 0.000 claims 1
• JMKDPYLGMRKJFG-UHFFFAOYSA-N 6-[1-[(6-methoxypyridin-3-yl)methyl]-4-methylpyrrolidin-3-yl]-3-(oxan-4-yl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=NC(OC)=CC=C1CN1CC(C=2NC(=O)C3=CN=C(N3C=2)C2CCOCC2)C(C)C1 JMKDPYLGMRKJFG-UHFFFAOYSA-N 0.000 claims 1
• KYRKGOCWXBDKBD-UHFFFAOYSA-N 6-[1-[3-(2-fluorophenoxy)azetidin-1-yl]ethyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1C(C)N(C1)CC1OC1=CC=CC=C1F KYRKGOCWXBDKBD-UHFFFAOYSA-N 0.000 claims 1
• YMFXDBVYLGTEJF-UHFFFAOYSA-N 6-[1-[3-(3-fluorophenoxy)azetidin-1-yl]ethyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1C(C)N(C1)CC1OC1=CC=CC(F)=C1 YMFXDBVYLGTEJF-UHFFFAOYSA-N 0.000 claims 1
• BYUYQURHJNXKRJ-UHFFFAOYSA-N 6-[1-[3-(4-ethylphenyl)azetidin-1-yl]ethyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(CC)=CC=C1C1CN(C(C)C=2NC(=O)C3=CN=C(N3C=2)C=2C=CC=CC=2)C1 BYUYQURHJNXKRJ-UHFFFAOYSA-N 0.000 claims 1
• BGGBTQOCEKKJHN-UHFFFAOYSA-N 6-[1-[3-(4-fluorophenoxy)azetidin-1-yl]ethyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1C(C)N(C1)CC1OC1=CC=C(F)C=C1 BGGBTQOCEKKJHN-UHFFFAOYSA-N 0.000 claims 1
• FKKWWRNYEOOBSX-UHFFFAOYSA-N 6-[1-[3-(4-fluorophenyl)azetidin-1-yl]ethyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1C(C)N(C1)CC1C1=CC=C(F)C=C1 FKKWWRNYEOOBSX-UHFFFAOYSA-N 0.000 claims 1
• WDONDXOUHDYLIG-UHFFFAOYSA-N 6-[1-[3-(4-fluorophenyl)azetidin-1-yl]propyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1C(CC)N(C1)CC1C1=CC=C(F)C=C1 WDONDXOUHDYLIG-UHFFFAOYSA-N 0.000 claims 1
• QQVRDHHMDLSEQM-UHFFFAOYSA-N 6-[1-[3-(4-methoxyphenyl)azetidin-1-yl]ethyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(OC)=CC=C1C1CN(C(C)C=2NC(=O)C3=CN=C(N3C=2)C=2C=CC=CC=2)C1 QQVRDHHMDLSEQM-UHFFFAOYSA-N 0.000 claims 1
• BOPIZTALPMZROL-UHFFFAOYSA-N 6-[1-[3-(6-fluoropyridin-2-yl)oxyazetidin-1-yl]ethyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C=3C=CC=CC=3)=NC=C2C(=O)NC=1C(C)N(C1)CC1OC1=CC=CC(F)=N1 BOPIZTALPMZROL-UHFFFAOYSA-N 0.000 claims 1
• PTYLHUJTFPIXHE-UHFFFAOYSA-N 6-[4-methyl-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(C=2NC(=O)C3=CN=C(N3C=2)C=2C=CC=CC=2)C(C)CN1CC1=CC=CC=N1 PTYLHUJTFPIXHE-UHFFFAOYSA-N 0.000 claims 1
• GWGNPYYVGANHRJ-UHFFFAOYSA-N 6-[4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-3-(oxan-4-yl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(C=2NC(=O)C3=CN=C(N3C=2)C2CCOCC2)C(C)CN1CC1=NC=CC=N1 GWGNPYYVGANHRJ-UHFFFAOYSA-N 0.000 claims 1
• PYOQDZOTVWIWHL-UHFFFAOYSA-N 6-[4-methyl-1-[(5-methylpyrazin-2-yl)methyl]pyrrolidin-3-yl]-3-(oxan-4-yl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(C=2NC(=O)C3=CN=C(N3C=2)C2CCOCC2)C(C)CN1CC1=CN=C(C)C=N1 PYOQDZOTVWIWHL-UHFFFAOYSA-N 0.000 claims 1
• PXARLARXUHGFMV-UHFFFAOYSA-N 6-[4-methyl-1-[[6-(trifluoromethyl)pyridin-3-yl]methyl]pyrrolidin-3-yl]-3-(oxan-4-yl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(C=2NC(=O)C3=CN=C(N3C=2)C2CCOCC2)C(C)CN1CC1=CC=C(C(F)(F)F)N=C1 PXARLARXUHGFMV-UHFFFAOYSA-N 0.000 claims 1
• JLEBAJSWVUDUBD-UHFFFAOYSA-N 6-[[3-(2-fluorophenoxy)azetidin-1-yl]methyl]-3-(4-fluorophenyl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)OC=3C(=CC=CC=3)F)=CN12 JLEBAJSWVUDUBD-UHFFFAOYSA-N 0.000 claims 1
• UJEUNNLUDXEEGX-UHFFFAOYSA-N 6-[[3-(2-fluorophenoxy)azetidin-1-yl]methyl]-3-(oxan-4-yl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound FC1=CC=CC=C1OC1CN(CC=2NC(=O)C3=CN=C(N3C=2)C2CCOCC2)C1 UJEUNNLUDXEEGX-UHFFFAOYSA-N 0.000 claims 1
• DXOVFJHHONEJOL-UHFFFAOYSA-N 6-[[3-(2-fluorophenoxy)azetidin-1-yl]methyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound FC1=CC=CC=C1OC1CN(CC=2NC(=O)C3=CN=C(N3C=2)C=2C=CC=CC=2)C1 DXOVFJHHONEJOL-UHFFFAOYSA-N 0.000 claims 1
• CBPZGUASFAPVKJ-UHFFFAOYSA-N 6-[[3-(3-fluorophenoxy)azetidin-1-yl]methyl]-3-(oxan-4-yl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound FC1=CC=CC(OC2CN(CC=3NC(=O)C4=CN=C(N4C=3)C3CCOCC3)C2)=C1 CBPZGUASFAPVKJ-UHFFFAOYSA-N 0.000 claims 1
• OMKMXPNRMOBLJW-UHFFFAOYSA-N 6-[[3-(3-fluorophenoxy)azetidin-1-yl]methyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound FC1=CC=CC(OC2CN(CC=3NC(=O)C4=CN=C(N4C=3)C=3C=CC=CC=3)C2)=C1 OMKMXPNRMOBLJW-UHFFFAOYSA-N 0.000 claims 1
• BCFBUHSRTSXNFB-UHFFFAOYSA-N 6-[[3-(4,6-dimethylpyrimidin-2-yl)oxyazetidin-1-yl]methyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound CC1=CC(C)=NC(OC2CN(CC=3NC(=O)C4=CN=C(N4C=3)C=3C=CC=CC=3)C2)=N1 BCFBUHSRTSXNFB-UHFFFAOYSA-N 0.000 claims 1
• MUKPBRXUGLLODQ-UHFFFAOYSA-N 6-[[3-(4-chlorophenoxy)azetidin-1-yl]methyl]-3-(4-fluorophenyl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)OC=3C=CC(Cl)=CC=3)=CN12 MUKPBRXUGLLODQ-UHFFFAOYSA-N 0.000 claims 1
• AITFNJPPLKQSLN-UHFFFAOYSA-N 6-[[3-(4-ethylphenyl)azetidin-1-yl]methyl]-3-(oxan-4-yl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(CC)=CC=C1C1CN(CC=2NC(=O)C3=CN=C(N3C=2)C2CCOCC2)C1 AITFNJPPLKQSLN-UHFFFAOYSA-N 0.000 claims 1
• OAMBWTBJNZOALP-UHFFFAOYSA-N 6-[[3-(4-ethylphenyl)azetidin-1-yl]methyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(CC)=CC=C1C1CN(CC=2NC(=O)C3=CN=C(N3C=2)C=2C=CC=CC=2)C1 OAMBWTBJNZOALP-UHFFFAOYSA-N 0.000 claims 1
• BLLWHEAFKONTLA-UHFFFAOYSA-N 6-[[3-(4-fluorophenoxy)azetidin-1-yl]methyl]-3-(4-fluorophenyl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1OC1CN(CC=2NC(=O)C3=CN=C(N3C=2)C=2C=CC(F)=CC=2)C1 BLLWHEAFKONTLA-UHFFFAOYSA-N 0.000 claims 1
• CPWSTVGPJSYNMA-UHFFFAOYSA-N 6-[[3-(4-fluorophenoxy)azetidin-1-yl]methyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1OC1CN(CC=2NC(=O)C3=CN=C(N3C=2)C=2C=CC=CC=2)C1 CPWSTVGPJSYNMA-UHFFFAOYSA-N 0.000 claims 1
• HZPADRFSJWFOFB-UHFFFAOYSA-N 6-[[3-(4-fluorophenyl)azetidin-1-yl]methyl]-3-(oxan-4-yl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1CN(CC=2NC(=O)C3=CN=C(N3C=2)C2CCOCC2)C1 HZPADRFSJWFOFB-UHFFFAOYSA-N 0.000 claims 1
• ZFKNXGNEVVKRER-UHFFFAOYSA-N 6-[[3-(4-fluorophenyl)azetidin-1-yl]methyl]-3-phenyl-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1CN(CC=2NC(=O)C3=CN=C(N3C=2)C=2C=CC=CC=2)C1 ZFKNXGNEVVKRER-UHFFFAOYSA-N 0.000 claims 1
• IMFVOVRGCNJMFI-UHFFFAOYSA-N 6-[[3-(4-methoxyphenyl)azetidin-1-yl]methyl]-3-(oxan-4-yl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(OC)=CC=C1C1CN(CC=2NC(=O)C3=CN=C(N3C=2)C2CCOCC2)C1 IMFVOVRGCNJMFI-UHFFFAOYSA-N 0.000 claims 1
• XFKYBBAASXSWEX-UHFFFAOYSA-N 6-[[3-[(4-chlorophenyl)methoxy]azetidin-1-yl]methyl]-3-(4-fluorophenyl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(C3)OCC=3C=CC(Cl)=CC=3)=CN12 XFKYBBAASXSWEX-UHFFFAOYSA-N 0.000 claims 1
• PSXDFVPKFJOWOJ-UHFFFAOYSA-N 6-[[3-[4-(dimethylamino)phenyl]azetidin-1-yl]methyl]-3-(4-fluorophenyl)-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(N(C)C)=CC=C1C1CN(CC=2NC(=O)C3=CN=C(N3C=2)C=2C=CC(F)=CC=2)C1 PSXDFVPKFJOWOJ-UHFFFAOYSA-N 0.000 claims 1
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