JP2015531401A - イミダゾピラジノン骨格を有するｐｄｅ９ｉ - Google Patents

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Publication number

JP2015531401A

JP2015531401A JP2015535994A JP2015535994A JP2015531401A JP 2015531401 A JP2015531401 A JP 2015531401A JP 2015535994 A JP2015535994 A JP 2015535994A JP 2015535994 A JP2015535994 A JP 2015535994A JP 2015531401 A JP2015531401 A JP 2015531401A

Authority

JP

Japan

Prior art keywords

imidazo

pyrazin

methyl

azetidin

fluorophenyl

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.)

Pending

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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 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 96
• 238000000034 method Methods 0.000 claims abstract description 19
• 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
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 6
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 6
• -1 8-oxo-3-phenyl-7H-imidazo [1,5-A] pyrazin-6-yl Chemical group 0.000 claims description 65
• 229910052801 chlorine Inorganic materials 0.000 claims description 25
• 229910052731 fluorine Inorganic materials 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 18
• 208000024827 Alzheimer disease Diseases 0.000 claims description 15
• 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
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 13
• 239000003085 diluting agent Substances 0.000 claims description 12
• 201000010099 disease Diseases 0.000 claims description 12
• 238000007363 ring formation reaction Methods 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 208000028017 Psychotic disease Diseases 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 7
• 241000218236 Cannabis Species 0.000 claims description 7
• 208000036626 Mental retardation Diseases 0.000 claims description 7
• 230000007000 age related cognitive decline Effects 0.000 claims description 7
• 208000015802 attention deficit-hyperactivity disease Diseases 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
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 6
• 229940025084 amphetamine Drugs 0.000 claims description 6
• 229940005483 opioid analgesics Drugs 0.000 claims description 6
• JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims description 6
• 229950010883 phencyclidine Drugs 0.000 claims description 6
• 208000011963 Substance-induced psychotic disease Diseases 0.000 claims description 5
• 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 239000001257 hydrogen Substances 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• 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
• ZLOQDIDEFDRYEQ-UHFFFAOYSA-N 3-phenyl-6-[(3-pyrazin-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=CN=CC=N1 ZLOQDIDEFDRYEQ-UHFFFAOYSA-N 0.000 claims description 2
• 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 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
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 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
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• MAKIYAKALMRMOD-UHFFFAOYSA-N 6-[[3-(6-fluoropyridin-2-yl)oxyazetidin-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)=N1 MAKIYAKALMRMOD-UHFFFAOYSA-N 0.000 claims description 2
• DMIUQICEZBGJHR-UHFFFAOYSA-N methyl 1-benzyl-4-(8-oxo-3-phenyl-7h-imidazo[1,5-a]pyrazin-6-yl)pyrrolidine-3-carboxylate Chemical compound C1C(C=2NC(=O)C3=CN=C(N3C=2)C=2C=CC=CC=2)C(C(=O)OC)CN1CC1=CC=CC=C1 DMIUQICEZBGJHR-UHFFFAOYSA-N 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 2
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 3
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
• 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
• 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
• FGZIMOPQPLAICG-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-[(3-phenoxypyrrolidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1=CC(F)=CC=C1C1=NC=C2C(=O)NC(CN3CC(CC3)OC=3C=CC=CC=3)=CN12 FGZIMOPQPLAICG-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
• 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 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
• 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
• MKUDSUOZOCBROM-UHFFFAOYSA-N 3-cyclopentyl-6-[(3-phenylmethoxyazetidin-1-yl)methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1N2C(C3CCCC3)=NC=C2C(=O)NC=1CN(C1)CC1OCC1=CC=CC=C1 MKUDSUOZOCBROM-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
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• GRNZCEOQTGFSIB-UHFFFAOYSA-N 3-cyclopentyl-6-[[3-(2-methylpropoxy)azetidin-1-yl]methyl]-7h-imidazo[1,5-a]pyrazin-8-one Chemical compound C1C(OCC(C)C)CN1CC(NC1=O)=CN2C1=CN=C2C1CCCC1 GRNZCEOQTGFSIB-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
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• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
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• 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
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• 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
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• 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
• 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
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