JP2007534678A5 - - Google Patents
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- JP2007534678A5 JP2007534678A5 JP2007508868A JP2007508868A JP2007534678A5 JP 2007534678 A5 JP2007534678 A5 JP 2007534678A5 JP 2007508868 A JP2007508868 A JP 2007508868A JP 2007508868 A JP2007508868 A JP 2007508868A JP 2007534678 A5 JP2007534678 A5 JP 2007534678A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- oxo
- phenyl
- propenyl
- fluoro
- 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.)
- Ceased
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- 150000001875 compounds Chemical class 0.000 claims description 37
- -1 nitro, oxy Chemical group 0.000 claims description 30
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 102100026456 POU domain, class 3, transcription factor 3 Human genes 0.000 claims description 2
- 101710133393 POU domain, class 3, transcription factor 3 Proteins 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- UOWIEOXAKVESDC-WEVVVXLNSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CNCC1CN(CC=1C=CC(F)=CC=1)C2 UOWIEOXAKVESDC-WEVVVXLNSA-N 0.000 claims description 2
- ALAXKIQXADBZFJ-VMPITWQZSA-N n-[5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C)C=C1\C=C\C(=O)N1C2COCC1CN(CC=1C=CC(F)=CC=1)C2 ALAXKIQXADBZFJ-VMPITWQZSA-N 0.000 claims description 2
- NVYLIMJHJUDLKD-QPJJXVBHSA-N n-[5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-pyrazin-2-ylphenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C=2N=CC=NC=2)C=C1\C=C\C(=O)N1C(C2)COCC1CN2CC1=CC=C(F)C=C1 NVYLIMJHJUDLKD-QPJJXVBHSA-N 0.000 claims description 2
- MCHSKFBELRXMHN-JXMROGBWSA-N n-[5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-pyridin-2-ylphenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C=2N=CC=CC=2)C=C1\C=C\C(=O)N1C(C2)COCC1CN2CC1=CC=C(F)C=C1 MCHSKFBELRXMHN-JXMROGBWSA-N 0.000 claims description 2
- SSBNVFBCXVCECX-VMPITWQZSA-N n-[5-chloro-2-[(e)-3-[9-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl]-3-oxoprop-1-enyl]-4-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C)C=C1\C=C\C(=O)N1CC(N2CC=3C=CC(F)=CC=3)COCC2C1 SSBNVFBCXVCECX-VMPITWQZSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 125000001424 substituent group Chemical group 0.000 claims 16
- PSDYQSWHANEKRV-UHFFFAOYSA-N [S]N Chemical compound [S]N PSDYQSWHANEKRV-UHFFFAOYSA-N 0.000 claims 13
- 125000003342 alkenyl group Chemical group 0.000 claims 13
- 125000000304 alkynyl group Chemical group 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000001475 halogen functional group Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 11
- 150000002431 hydrogen Chemical group 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 7
- 125000005549 heteroarylene group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 239000003550 marker Substances 0.000 claims 2
- BNWPUXZSTALSQB-WEVVVXLNSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CNCC1CN(CC=1C=CC(F)=CC=1)C2 BNWPUXZSTALSQB-WEVVVXLNSA-N 0.000 claims 2
- 238000002610 neuroimaging Methods 0.000 claims 2
- ZCFBGYBOYFTJJJ-PCUPJCOWSA-N (5r)-3-[5-chloro-2-[(e)-3-[(5s)-3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-(trifluoromethoxy)phenyl]-5-methylimidazolidine-2,4-dione Chemical compound C([C@@](C1)(N2C(=O)\C=C\C=3C(=CC(Cl)=C(OC(F)(F)F)C=3)N3C([C@@H](C)NC3=O)=O)[H])CC2CN1CC1=CC=C(F)C=C1 ZCFBGYBOYFTJJJ-PCUPJCOWSA-N 0.000 claims 1
- GPNIJIJFLZKGAQ-IZFFEBQESA-N (5r)-3-[5-chloro-2-[(e)-3-[(5s)-3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]-5-methylimidazolidine-2,4-dione Chemical compound C([C@@](C1)(N2C(=O)\C=C\C=3C(=CC(Cl)=C(OC)C=3)N3C([C@@H](C)NC3=O)=O)[H])CC2CN1CC1=CC=C(F)C=C1 GPNIJIJFLZKGAQ-IZFFEBQESA-N 0.000 claims 1
- VWSVNYLTINOUHQ-HAAWTFQLSA-N (E)-3-(2-amino-4-chloro-5-methylphenyl)-1-[3-[(4-fluorophenyl)methyl]-7-methyl-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]prop-2-en-1-one hydrochloride Chemical compound Cl.C1C(N2C(=O)\C=C\C=3C(=CC(Cl)=C(C)C=3)N)CN(C)CC2CN1CC1=CC=C(F)C=C1 VWSVNYLTINOUHQ-HAAWTFQLSA-N 0.000 claims 1
- VNLODBPNDFBDLV-DUXPYHPUSA-N (E)-5-[1-chloro-9-[(4-fluorophenyl)methyl]-7-methyl-3,7,9-triazabicyclo[3.3.1]nonan-3-yl]-5-oxopent-3-enamide Chemical compound C1N(C)CC2CN(C(=O)\C=C\CC(N)=O)CC1(Cl)N2CC1=CC=C(F)C=C1 VNLODBPNDFBDLV-DUXPYHPUSA-N 0.000 claims 1
- CBPQYCHYMFLLNO-RUDMXATFSA-N 1-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-(trifluoromethoxy)phenyl]-3-methylurea Chemical compound CNC(=O)NC1=CC(Cl)=C(OC(F)(F)F)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 CBPQYCHYMFLLNO-RUDMXATFSA-N 0.000 claims 1
- BRLLZEMSQKDJIF-NYYWCZLTSA-N 1-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]-3-cyclopropylurea Chemical compound C1CC1NC(=O)NC=1C=C(Cl)C(OC)=CC=1\C=C\C(=O)N1C(C2)CCC1CN2CC1=CC=C(F)C=C1 BRLLZEMSQKDJIF-NYYWCZLTSA-N 0.000 claims 1
- OEWRLZBZEGABJE-BJMVGYQFSA-N 1-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]-3-methylurea Chemical compound CNC(=O)NC1=CC(Cl)=C(OC)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 OEWRLZBZEGABJE-BJMVGYQFSA-N 0.000 claims 1
- PAGBTVXBVDPORE-NYYWCZLTSA-N 1-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methylphenyl]-3-cyclopropylurea Chemical compound C1CC1NC(=O)NC=1C=C(Cl)C(C)=CC=1\C=C\C(=O)N1C(C2)CCC1CN2CC1=CC=C(F)C=C1 PAGBTVXBVDPORE-NYYWCZLTSA-N 0.000 claims 1
- BMKRVNUKPVZLPR-BJMVGYQFSA-N 1-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methylphenyl]-3-methylurea Chemical compound CNC(=O)NC1=CC(Cl)=C(C)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 BMKRVNUKPVZLPR-BJMVGYQFSA-N 0.000 claims 1
- CLLQAXBEKRTEME-ONNFQVAWSA-N 1-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]-3-(oxan-4-yl)urea Chemical compound C1=CC(F)=CC=C1CN1CC(N2C(=O)\C=C\C=3C(=CC(Cl)=CC=3)NC(=O)NC3CCOCC3)CCC2C1 CLLQAXBEKRTEME-ONNFQVAWSA-N 0.000 claims 1
- UWKYVRJCWCFUOI-UUILKARUSA-N 1-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]-3-cyclopropylurea Chemical compound C1=CC(F)=CC=C1CN1CC(N2C(=O)\C=C\C=3C(=CC(Cl)=CC=3)NC(=O)NC3CC3)CCC2C1 UWKYVRJCWCFUOI-UUILKARUSA-N 0.000 claims 1
- YLAQWEJDXXBQGI-WUXMJOGZSA-N 1-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]-3-ethylurea Chemical compound CCNC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 YLAQWEJDXXBQGI-WUXMJOGZSA-N 0.000 claims 1
- LWPIZYDAXJWXRV-VZUCSPMQSA-N 1-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]-3-methylurea Chemical compound CNC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 LWPIZYDAXJWXRV-VZUCSPMQSA-N 0.000 claims 1
- ROHUDTKBKCYECP-WUXMJOGZSA-N 1-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 ROHUDTKBKCYECP-WUXMJOGZSA-N 0.000 claims 1
- WKCFFCBKSSUABJ-WUXMJOGZSA-N 1-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]-3-propylurea Chemical compound CCCNC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 WKCFFCBKSSUABJ-WUXMJOGZSA-N 0.000 claims 1
- GTHLQEAGFSFWJB-QPJJXVBHSA-N 1-[5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-(trifluoromethoxy)phenyl]-3-methylurea Chemical compound CNC(=O)NC1=CC(Cl)=C(OC(F)(F)F)C=C1\C=C\C(=O)N1C2COCC1CN(CC=1C=CC(F)=CC=1)C2 GTHLQEAGFSFWJB-QPJJXVBHSA-N 0.000 claims 1
- CFNOLVOGGAQVSV-RUDMXATFSA-N 1-[5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]-3-cyclopropylurea Chemical compound C1CC1NC(=O)NC=1C=C(Cl)C(OC)=CC=1\C=C\C(=O)N1C(C2)COCC1CN2CC1=CC=C(F)C=C1 CFNOLVOGGAQVSV-RUDMXATFSA-N 0.000 claims 1
- VGEAVTCRYVDVGT-VMPITWQZSA-N 1-[5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]-3-methylurea Chemical compound CNC(=O)NC1=CC(Cl)=C(OC)C=C1\C=C\C(=O)N1C2COCC1CN(CC=1C=CC(F)=CC=1)C2 VGEAVTCRYVDVGT-VMPITWQZSA-N 0.000 claims 1
- ZIHBBCWNZUEJDE-WUXMJOGZSA-N 1-[5-chloro-2-[(e)-3-[8-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-3-yl]-3-oxoprop-1-enyl]phenyl]-3-ethylurea Chemical compound CCNC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1CC(N2CC=3C=CC(F)=CC=3)CCC2C1 ZIHBBCWNZUEJDE-WUXMJOGZSA-N 0.000 claims 1
- MWAMSZYFJCSGCY-VZUCSPMQSA-N 1-[5-chloro-2-[(e)-3-[8-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-3-yl]-3-oxoprop-1-enyl]phenyl]-3-methylurea Chemical compound CNC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1CC(N2CC=3C=CC(F)=CC=3)CCC2C1 MWAMSZYFJCSGCY-VZUCSPMQSA-N 0.000 claims 1
- NSWDFZVKCGMQNK-KPKJPENVSA-N 1-tert-butylsulfonyl-1-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methylphenyl]urea Chemical compound C1=C(Cl)C(C)=CC(\C=C\C(=O)N2C3CCC2CN(CC=2C=CC(F)=CC=2)C3)=C1N(C(N)=O)S(=O)(=O)C(C)(C)C NSWDFZVKCGMQNK-KPKJPENVSA-N 0.000 claims 1
- NYVMYYZWYNUUSM-SWSRPJROSA-N 2-[5-chloro-2-[(E)-3-[3-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methylphenyl]-2-(dimethylamino)acetamide dihydrochloride Chemical compound Cl.Cl.CN(C)C(C(N)=O)C1=CC(Cl)=C(C)C=C1\C=C\C(=O)N1C2CNCC1CN(CC=1C=CC(F)=CC=1)C2 NYVMYYZWYNUUSM-SWSRPJROSA-N 0.000 claims 1
- FQEYNBGNPWZWHX-KQGICBIGSA-N 2-[5-chloro-2-[(E)-3-[3-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methylphenyl]acetamide hydrochloride Chemical compound Cl.C1=C(Cl)C(C)=CC(\C=C\C(=O)N2C3CNCC2CN(CC=2C=CC(F)=CC=2)C3)=C1CC(N)=O FQEYNBGNPWZWHX-KQGICBIGSA-N 0.000 claims 1
- ZOSSCUBSVCMKKI-UHFFFAOYSA-N 2-[5-chloro-2-[3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]-1-cyanoguanidine Chemical compound C1=CC(F)=CC=C1CN1CC(N2C(=O)C=CC=3C(=CC(Cl)=CC=3)NC(=N)NC#N)CCC2C1 ZOSSCUBSVCMKKI-UHFFFAOYSA-N 0.000 claims 1
- JQGCTAAHBMFDJB-UHFFFAOYSA-N 2-[5-chloro-2-[3-[3-[(4-fluorophenyl)methyl]-3,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]-1-cyanoguanidine Chemical compound C1=CC(F)=CC=C1CN1CC(N2C(=O)C=CC=3C(=CC(Cl)=CC=3)NC(=N)NC#N)CCCC2C1 JQGCTAAHBMFDJB-UHFFFAOYSA-N 0.000 claims 1
- LYNUQRDHRUZTBF-UHFFFAOYSA-N 2-[5-chloro-2-[3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]-1-cyanoguanidine Chemical compound C1=CC(F)=CC=C1CN1CC(N2C(=O)C=CC=3C(=CC(Cl)=CC=3)NC(=N)NC#N)COCC2C1 LYNUQRDHRUZTBF-UHFFFAOYSA-N 0.000 claims 1
- ZDBLLKMVFVTGAI-BJMVGYQFSA-N 3-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-(trifluoromethoxy)phenyl]-1,1-bis(methylsulfonyl)urea Chemical compound CS(=O)(=O)N(S(C)(=O)=O)C(=O)NC1=CC(Cl)=C(OC(F)(F)F)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 ZDBLLKMVFVTGAI-BJMVGYQFSA-N 0.000 claims 1
- ACBHEGPKUJLJQG-BJMVGYQFSA-N 3-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-(trifluoromethoxy)phenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC(Cl)=C(OC(F)(F)F)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 ACBHEGPKUJLJQG-BJMVGYQFSA-N 0.000 claims 1
- WXYUMBFYYOWTDI-IZZDOVSWSA-N 3-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]-1,1-dimethylurea Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(=O)N(C)C WXYUMBFYYOWTDI-IZZDOVSWSA-N 0.000 claims 1
- CWBZDEATHNQGLA-IZZDOVSWSA-N 3-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methylphenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC(Cl)=C(C)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 CWBZDEATHNQGLA-IZZDOVSWSA-N 0.000 claims 1
- OWLXPIJOBFYBNG-WUXMJOGZSA-N 3-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 OWLXPIJOBFYBNG-WUXMJOGZSA-N 0.000 claims 1
- CUYVIMOCUCZAEE-WUXMJOGZSA-N 3-[5-chloro-2-[(e)-3-[8-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-3-yl]-3-oxoprop-1-enyl]phenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1CC(N2CC=3C=CC(F)=CC=3)CCC2C1 CUYVIMOCUCZAEE-WUXMJOGZSA-N 0.000 claims 1
- FCMSYZZMRJEKLZ-IZZDOVSWSA-N 5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methoxy-n,n-dimethylbenzenesulfonamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CCC2CN(CC=2C=CC(F)=CC=2)C3)=C1S(=O)(=O)N(C)C FCMSYZZMRJEKLZ-IZZDOVSWSA-N 0.000 claims 1
- BVRNXOAEGFHCRX-IZZDOVSWSA-N 5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-n,n,4-trimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC(Cl)=C(C)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 BVRNXOAEGFHCRX-IZZDOVSWSA-N 0.000 claims 1
- JUIWTXOXWOYYGH-BJMVGYQFSA-N 5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-n,n-dimethyl-4-(trifluoromethoxy)benzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC(Cl)=C(OC(F)(F)F)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 JUIWTXOXWOYYGH-BJMVGYQFSA-N 0.000 claims 1
- MBJVOIBNOKYVGA-RMKNXTFCSA-N 5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-methylsulfonyl-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-n,n-dimethyl-4-(trifluoromethoxy)benzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC(Cl)=C(OC(F)(F)F)C=C1\C=C\C(=O)N1C2CN(CC=3C=CC(F)=CC=3)CC1CN(S(C)(=O)=O)C2 MBJVOIBNOKYVGA-RMKNXTFCSA-N 0.000 claims 1
- WRASPMSGEFWYEA-RMKNXTFCSA-N 5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methoxy-n,n-dimethylbenzenesulfonamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3COCC2CN(CC=2C=CC(F)=CC=2)C3)=C1S(=O)(=O)N(C)C WRASPMSGEFWYEA-RMKNXTFCSA-N 0.000 claims 1
- HVQCXSGCXKXCKT-VMPITWQZSA-N 5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-n,n-dimethyl-4-(trifluoromethoxy)benzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC(Cl)=C(OC(F)(F)F)C=C1\C=C\C(=O)N1C2COCC1CN(CC=1C=CC(F)=CC=1)C2 HVQCXSGCXKXCKT-VMPITWQZSA-N 0.000 claims 1
- JSWHDHBXIHEXAL-FPYGCLRLSA-N 6-[5-chloro-4-fluoro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]-4,6-diazaspiro[2.4]heptane-5,7-dione Chemical compound C1=CC(F)=CC=C1CN1CC(N2C(=O)\C=C\C=3C(=CC(Cl)=C(F)C=3)N3C(C4(CC4)NC3=O)=O)CCC2C1 JSWHDHBXIHEXAL-FPYGCLRLSA-N 0.000 claims 1
- WGDHXEFFOPSBLZ-JXMROGBWSA-N 9-[(e)-3-(2-acetamido-4-chloro-5-methoxyphenyl)prop-2-enoyl]-7-[(4-fluorophenyl)methyl]-n,n-dimethyl-3,7,9-triazabicyclo[3.3.1]nonane-3-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CN(CC=4C=CC(F)=CC=4)CC2CN(C3)C(=O)N(C)C)=C1NC(C)=O WGDHXEFFOPSBLZ-JXMROGBWSA-N 0.000 claims 1
- JQBLBDFZKFUEQR-RMKNXTFCSA-N 9-[(e)-3-(2-acetamido-4-chloro-5-methoxyphenyl)prop-2-enoyl]-7-[(4-fluorophenyl)methyl]-n-methyl-3,7,9-triazabicyclo[3.3.1]nonane-3-carboxamide Chemical compound C1C(N2C(=O)\C=C\C=3C(=CC(Cl)=C(OC)C=3)NC(C)=O)CN(C(=O)NC)CC2CN1CC1=CC=C(F)C=C1 JQBLBDFZKFUEQR-RMKNXTFCSA-N 0.000 claims 1
- 241000270666 Testudines Species 0.000 claims 1
- LQHSFGGIIZYBKO-KQGICBIGSA-N [5-chloro-2-[(E)-3-[3-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methylphenyl]methanesulfonamide hydrochloride Chemical compound Cl.C1=C(Cl)C(C)=CC(\C=C\C(=O)N2C3CNCC2CN(CC=2C=CC(F)=CC=2)C3)=C1CS(N)(=O)=O LQHSFGGIIZYBKO-KQGICBIGSA-N 0.000 claims 1
- DVSVALJWXIYKFD-KQGICBIGSA-N [5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]urea;hydrochloride Chemical compound Cl.C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CNCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(N)=O DVSVALJWXIYKFD-KQGICBIGSA-N 0.000 claims 1
- HGUDESYCNAZDBE-KQGICBIGSA-N [5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methylphenyl]urea;hydrochloride Chemical compound Cl.C1=C(Cl)C(C)=CC(\C=C\C(=O)N2C3CNCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(N)=O HGUDESYCNAZDBE-KQGICBIGSA-N 0.000 claims 1
- HJRQAXMMLGYIJE-ZFXMFRGYSA-N [5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]urea;hydrochloride Chemical compound Cl.NC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CNCC1CN(CC=1C=CC(F)=CC=1)C2 HJRQAXMMLGYIJE-ZFXMFRGYSA-N 0.000 claims 1
- XTORCRXTQAEYSA-FPYGCLRLSA-N [5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-(trifluoromethoxy)phenyl]urea Chemical compound NC(=O)NC1=CC(Cl)=C(OC(F)(F)F)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 XTORCRXTQAEYSA-FPYGCLRLSA-N 0.000 claims 1
- UZHFLDHBRPTPST-RUDMXATFSA-N [5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methylphenyl]urea Chemical compound C1=C(Cl)C(C)=CC(\C=C\C(=O)N2C3CCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(N)=O UZHFLDHBRPTPST-RUDMXATFSA-N 0.000 claims 1
- XXQINDOIELYJRD-BJMVGYQFSA-N [5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-pyridin-3-ylphenyl]urea Chemical compound NC(=O)NC1=CC(Cl)=C(C=2C=NC=CC=2)C=C1\C=C\C(=O)N1C(C2)CCC1CN2CC1=CC=C(F)C=C1 XXQINDOIELYJRD-BJMVGYQFSA-N 0.000 claims 1
- UUXLYSOVZWVXTE-ONNFQVAWSA-N [5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound NC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 UUXLYSOVZWVXTE-ONNFQVAWSA-N 0.000 claims 1
- RFLJRKZGUDSBIQ-YRNVUSSQSA-N [5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound NC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CCCC1CN(CC=1C=CC(F)=CC=1)C2 RFLJRKZGUDSBIQ-YRNVUSSQSA-N 0.000 claims 1
- FNRDECOLGDEDAI-VMPITWQZSA-N [5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-7-methyl-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]urea Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CN(C)CC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(N)=O FNRDECOLGDEDAI-VMPITWQZSA-N 0.000 claims 1
- DGJMLIHYOQELDD-HAAWTFQLSA-N [5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-7-methyl-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methylphenyl]urea;hydrochloride Chemical compound Cl.C1C(N2C(=O)\C=C\C=3C(=CC(Cl)=C(C)C=3)NC(N)=O)CN(C)CC2CN1CC1=CC=C(F)C=C1 DGJMLIHYOQELDD-HAAWTFQLSA-N 0.000 claims 1
- CCGILYGVXQDZEW-WEVVVXLNSA-N [5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-7-methyl-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound C1C(N2C(=O)\C=C\C=3C(=CC(Cl)=CC=3)NC(N)=O)CN(C)CC2CN1CC1=CC=C(F)C=C1 CCGILYGVXQDZEW-WEVVVXLNSA-N 0.000 claims 1
- TVPPDGCRGUPQNY-ZZXKWVIFSA-N [5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-(trifluoromethoxy)phenyl]urea Chemical compound NC(=O)NC1=CC(Cl)=C(OC(F)(F)F)C=C1\C=C\C(=O)N1C2COCC1CN(CC=1C=CC(F)=CC=1)C2 TVPPDGCRGUPQNY-ZZXKWVIFSA-N 0.000 claims 1
- ICYHXAZDGFXPBV-XBXARRHUSA-N [5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound NC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2COCC1CN(CC=1C=CC(F)=CC=1)C2 ICYHXAZDGFXPBV-XBXARRHUSA-N 0.000 claims 1
- MVLRXQRLEYZCTJ-ONNFQVAWSA-N [5-chloro-2-[(e)-3-[8-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-3-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound NC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1CC(N2CC=3C=CC(F)=CC=3)CCC2C1 MVLRXQRLEYZCTJ-ONNFQVAWSA-N 0.000 claims 1
- KXGMWAIMWUIYOE-QPJJXVBHSA-N [5-chloro-2-[(e)-3-[9-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]urea Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2CC3COCC(N3CC=3C=CC(F)=CC=3)C2)=C1NC(N)=O KXGMWAIMWUIYOE-QPJJXVBHSA-N 0.000 claims 1
- HHYMBEGYBIIHRX-XBXARRHUSA-N [5-chloro-2-[(e)-3-[9-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound NC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1CC(N2CC=3C=CC(F)=CC=3)COCC2C1 HHYMBEGYBIIHRX-XBXARRHUSA-N 0.000 claims 1
- NBXKHFIRAQQQQY-BJMVGYQFSA-N [5-chloro-4-ethoxy-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound C1=C(Cl)C(OCC)=CC(\C=C\C(=O)N2C3CCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(N)=O NBXKHFIRAQQQQY-BJMVGYQFSA-N 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- NKQVOPNFLDBLJZ-RMKNXTFCSA-N methyl 9-[(e)-3-(2-acetamido-4-chloro-5-methoxyphenyl)prop-2-enoyl]-7-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonane-3-carboxylate Chemical compound C1C(N2C(=O)\C=C\C=3C(=CC(Cl)=C(OC)C=3)NC(C)=O)CN(C(=O)OC)CC2CN1CC1=CC=C(F)C=C1 NKQVOPNFLDBLJZ-RMKNXTFCSA-N 0.000 claims 1
- BLFPVCAJVYOULB-VMPITWQZSA-N n-[2-[(e)-3-[3-acetyl-7-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-5-chloro-4-fluorophenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(F)C=C1\C=C\C(=O)N1C2CN(CC=3C=CC(F)=CC=3)CC1CN(C(C)=O)C2 BLFPVCAJVYOULB-VMPITWQZSA-N 0.000 claims 1
- UAVJYXHPMOEYMC-RMKNXTFCSA-N n-[2-[(e)-3-[3-acetyl-7-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-5-chloro-4-methoxyphenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CN(CC=4C=CC(F)=CC=4)CC2CN(C3)C(C)=O)=C1NC(C)=O UAVJYXHPMOEYMC-RMKNXTFCSA-N 0.000 claims 1
- PXKCWYFRQJCUEH-RMKNXTFCSA-N n-[2-[(e)-3-[3-acetyl-7-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-5-chloro-4-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C)C=C1\C=C\C(=O)N1C2CN(CC=3C=CC(F)=CC=3)CC1CN(C(C)=O)C2 PXKCWYFRQJCUEH-RMKNXTFCSA-N 0.000 claims 1
- BJSZLRDADOCRDR-MDWZMJQESA-N n-[3-[4-acetamido-2-chloro-5-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C(=CC(NC(C)=O)=C(\C=C\C(=O)N3C4CCC3CN(CC=3C=CC(F)=CC=3)C4)C=2)Cl)=C1 BJSZLRDADOCRDR-MDWZMJQESA-N 0.000 claims 1
- ODIUINXYFAWCAN-IZZDOVSWSA-N n-[3-chloro-6-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-2,4-dimethoxyphenyl]acetamide Chemical compound COC1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(C)=O ODIUINXYFAWCAN-IZZDOVSWSA-N 0.000 claims 1
- NOAPPTMGSUTSKV-RMKNXTFCSA-N n-[3-chloro-6-[(e)-3-[9-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl]-3-oxoprop-1-enyl]-2,4-dimethoxyphenyl]acetamide Chemical compound COC1=C(Cl)C(OC)=CC(\C=C\C(=O)N2CC3COCC(N3CC=3C=CC(F)=CC=3)C2)=C1NC(C)=O NOAPPTMGSUTSKV-RMKNXTFCSA-N 0.000 claims 1
- YQCSILINHFPQMK-UXBLZVDNSA-N n-[3-chloro-6-[(e)-3-[9-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl]-3-oxoprop-1-enyl]-2-methoxyphenyl]acetamide Chemical compound COC1=C(Cl)C=CC(\C=C\C(=O)N2CC3COCC(N3CC=3C=CC(F)=CC=3)C2)=C1NC(C)=O YQCSILINHFPQMK-UXBLZVDNSA-N 0.000 claims 1
- CSBMBURIGJBLRR-KPKJPENVSA-N n-[4-(3-aminophenyl)-5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C=2C=C(N)C=CC=2)C=C1\C=C\C(=O)N1C(C2)CCC1CN2CC1=CC=C(F)C=C1 CSBMBURIGJBLRR-KPKJPENVSA-N 0.000 claims 1
- RPNOYURQBSHDAC-KPKJPENVSA-N n-[4-[3-(carbamoylamino)phenyl]-5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C=2C=C(NC(N)=O)C=CC=2)C=C1\C=C\C(=O)N1C(C2)CCC1CN2CC1=CC=C(F)C=C1 RPNOYURQBSHDAC-KPKJPENVSA-N 0.000 claims 1
- AMEAYLFINGJCON-SWSRPJROSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]-2-(dimethylamino)acetamide;dihydrochloride Chemical compound Cl.Cl.C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CNCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(=O)CN(C)C AMEAYLFINGJCON-SWSRPJROSA-N 0.000 claims 1
- NHEUHTIILFBAJO-VMPITWQZSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CNCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(C)=O NHEUHTIILFBAJO-VMPITWQZSA-N 0.000 claims 1
- NZUVKLMWWXVBPD-HAAWTFQLSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]methanesulfonamide;hydrochloride Chemical compound Cl.C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CNCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NS(C)(=O)=O NZUVKLMWWXVBPD-HAAWTFQLSA-N 0.000 claims 1
- NECUVOIMBRGEDI-UXBLZVDNSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]-2-(dimethylamino)acetamide Chemical compound CN(C)CC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CNCC1CN(CC=1C=CC(F)=CC=1)C2 NECUVOIMBRGEDI-UXBLZVDNSA-N 0.000 claims 1
- ZIONMROITBRSNL-IZZDOVSWSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-(2-hydroxypropan-2-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C(C)(C)O)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 ZIONMROITBRSNL-IZZDOVSWSA-N 0.000 claims 1
- AJXYPFDIPQCQHV-RUDMXATFSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-(trifluoromethoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(OC(F)(F)F)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 AJXYPFDIPQCQHV-RUDMXATFSA-N 0.000 claims 1
- KVMVWTUUTDOLFT-IZZDOVSWSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]-2-(dimethylamino)acetamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(=O)CN(C)C KVMVWTUUTDOLFT-IZZDOVSWSA-N 0.000 claims 1
- GRXAAIBPDTYJKW-BJMVGYQFSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(C)=O GRXAAIBPDTYJKW-BJMVGYQFSA-N 0.000 claims 1
- ATGXYHCXARRPGD-BJMVGYQFSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]methanesulfonamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NS(C)(=O)=O ATGXYHCXARRPGD-BJMVGYQFSA-N 0.000 claims 1
- NUDMSUNJGUKNDN-BJMVGYQFSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methylphenyl]-2-methoxyacetamide Chemical compound COCC(=O)NC1=CC(Cl)=C(C)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 NUDMSUNJGUKNDN-BJMVGYQFSA-N 0.000 claims 1
- SRAIDNXIYJWTIG-RUDMXATFSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methylphenyl]-3-oxopiperazine-1-carboxamide Chemical compound C1CNC(=O)CN1C(=O)NC=1C=C(Cl)C(C)=CC=1\C=C\C(=O)N1C(C2)CCC1CN2CC1=CC=C(F)C=C1 SRAIDNXIYJWTIG-RUDMXATFSA-N 0.000 claims 1
- CVPFGDMAYVQBHH-BJMVGYQFSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 CVPFGDMAYVQBHH-BJMVGYQFSA-N 0.000 claims 1
- JKXHTVFFNULCOO-BJMVGYQFSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-methylphenyl]methanesulfonamide Chemical compound C1=C(Cl)C(C)=CC(\C=C\C(=O)N2C3CCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NS(C)(=O)=O JKXHTVFFNULCOO-BJMVGYQFSA-N 0.000 claims 1
- OYQPAWUIEIJVLO-RUDMXATFSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-pyrazin-2-ylphenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C=2N=CC=NC=2)C=C1\C=C\C(=O)N1C(C2)CCC1CN2CC1=CC=C(F)C=C1 OYQPAWUIEIJVLO-RUDMXATFSA-N 0.000 claims 1
- AJFLNTNUZILNBQ-KPKJPENVSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-pyridin-2-ylphenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C=2N=CC=CC=2)C=C1\C=C\C(=O)N1C(C2)CCC1CN2CC1=CC=C(F)C=C1 AJFLNTNUZILNBQ-KPKJPENVSA-N 0.000 claims 1
- XGDMIKUQQXFEIL-IZZDOVSWSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]-4-pyridin-3-ylphenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C=2C=NC=CC=2)C=C1\C=C\C(=O)N1C(C2)CCC1CN2CC1=CC=C(F)C=C1 XGDMIKUQQXFEIL-IZZDOVSWSA-N 0.000 claims 1
- PANTVKZNEGNKCZ-WUXMJOGZSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]-2-(dimethylamino)acetamide Chemical compound CN(C)CC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 PANTVKZNEGNKCZ-WUXMJOGZSA-N 0.000 claims 1
- MXORRQKSYQOAGW-VZUCSPMQSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]-2-methoxyacetamide Chemical compound COCC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 MXORRQKSYQOAGW-VZUCSPMQSA-N 0.000 claims 1
- MQEFGDOFFAKTDW-ONNFQVAWSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]-2-oxo-1,3-oxazolidine-3-sulfonamide Chemical compound C1=CC(F)=CC=C1CN1CC(N2C(=O)\C=C\C=3C(=CC(Cl)=CC=3)NS(=O)(=O)N3C(OCC3)=O)CCC2C1 MQEFGDOFFAKTDW-ONNFQVAWSA-N 0.000 claims 1
- BYINHBQSHPPZOZ-ONNFQVAWSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]-3-oxopiperazine-1-carboxamide Chemical compound C1=CC(F)=CC=C1CN1CC(N2C(=O)\C=C\C=3C(=CC(Cl)=CC=3)NC(=O)N3CC(=O)NCC3)CCC2C1 BYINHBQSHPPZOZ-ONNFQVAWSA-N 0.000 claims 1
- MTOLJUPHQKMSMQ-VZUCSPMQSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 MTOLJUPHQKMSMQ-VZUCSPMQSA-N 0.000 claims 1
- VLHPAVJOAMLQAM-VZUCSPMQSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 VLHPAVJOAMLQAM-VZUCSPMQSA-N 0.000 claims 1
- YMTYSIHCESLJLR-UKTHLTGXSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]-2-(dimethylamino)acetamide Chemical compound CN(C)CC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CCCC1CN(CC=1C=CC(F)=CC=1)C2 YMTYSIHCESLJLR-UKTHLTGXSA-N 0.000 claims 1
- RBOKCYBGTIKYMQ-XYOKQWHBSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2CCCC1CN(CC=1C=CC(F)=CC=1)C2 RBOKCYBGTIKYMQ-XYOKQWHBSA-N 0.000 claims 1
- SSFDQYULGOMSMT-RMKNXTFCSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-7-methyl-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CN(C)CC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(C)=O SSFDQYULGOMSMT-RMKNXTFCSA-N 0.000 claims 1
- DXSNVDIWGSJZFM-RMKNXTFCSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-7-methyl-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]methanesulfonamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3CN(C)CC2CN(CC=2C=CC(F)=CC=2)C3)=C1NS(C)(=O)=O DXSNVDIWGSJZFM-RMKNXTFCSA-N 0.000 claims 1
- NFRKPUTZOHSTKO-RMKNXTFCSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-7-methyl-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methylphenyl]methanesulfonamide Chemical compound C1C(N2C(=O)\C=C\C=3C(=CC(Cl)=C(C)C=3)NS(C)(=O)=O)CN(C)CC2CN1CC1=CC=C(F)C=C1 NFRKPUTZOHSTKO-RMKNXTFCSA-N 0.000 claims 1
- FAGZYDDCOFJCFB-UXBLZVDNSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-7-methyl-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C1C(N2C(=O)\C=C\C=3C(=CC(Cl)=CC=3)NC(C)=O)CN(C)CC2CN1CC1=CC=C(F)C=C1 FAGZYDDCOFJCFB-UXBLZVDNSA-N 0.000 claims 1
- YBQVUSGHJJFTKA-UXBLZVDNSA-N n-[5-chloro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-7-methyl-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]methanesulfonamide Chemical compound C1C(N2C(=O)\C=C\C=3C(=CC(Cl)=CC=3)NS(C)(=O)=O)CN(C)CC2CN1CC1=CC=C(F)C=C1 YBQVUSGHJJFTKA-UXBLZVDNSA-N 0.000 claims 1
- DSBUSUUJWJRFHF-VMPITWQZSA-N n-[5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-(trifluoromethoxy)phenyl]-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=CC(Cl)=C(OC(F)(F)F)C=C1\C=C\C(=O)N1C2COCC1CN(CC=1C=CC(F)=CC=1)C2 DSBUSUUJWJRFHF-VMPITWQZSA-N 0.000 claims 1
- WQGDKRWWQBKRPX-QPJJXVBHSA-N n-[5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-(trifluoromethoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(OC(F)(F)F)C=C1\C=C\C(=O)N1C2COCC1CN(CC=1C=CC(F)=CC=1)C2 WQGDKRWWQBKRPX-QPJJXVBHSA-N 0.000 claims 1
- VUXGCHILBNAYBR-VMPITWQZSA-N n-[5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3COCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(C)=O VUXGCHILBNAYBR-VMPITWQZSA-N 0.000 claims 1
- FBZPOVOXGFWSAU-VMPITWQZSA-N n-[5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]methanesulfonamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2C3COCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NS(C)(=O)=O FBZPOVOXGFWSAU-VMPITWQZSA-N 0.000 claims 1
- MBMRNFVXMXIBFM-WEVVVXLNSA-N n-[5-chloro-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1C2COCC1CN(CC=1C=CC(F)=CC=1)C2 MBMRNFVXMXIBFM-WEVVVXLNSA-N 0.000 claims 1
- CHVHBBZSTJTDIX-VZUCSPMQSA-N n-[5-chloro-2-[(e)-3-[8-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-3-yl]-3-oxoprop-1-enyl]phenyl]-2-methoxyacetamide Chemical compound COCC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1CC(N2CC=3C=CC(F)=CC=3)CCC2C1 CHVHBBZSTJTDIX-VZUCSPMQSA-N 0.000 claims 1
- WVUZZGNQHVFNKJ-VZUCSPMQSA-N n-[5-chloro-2-[(e)-3-[8-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-3-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1CC(N2CC=3C=CC(F)=CC=3)CCC2C1 WVUZZGNQHVFNKJ-VZUCSPMQSA-N 0.000 claims 1
- WPQPDYADSMRAJW-VZUCSPMQSA-N n-[5-chloro-2-[(e)-3-[8-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-3-yl]-3-oxoprop-1-enyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1CC(N2CC=3C=CC(F)=CC=3)CCC2C1 WPQPDYADSMRAJW-VZUCSPMQSA-N 0.000 claims 1
- XKLXSHKFDPEOPK-VMPITWQZSA-N n-[5-chloro-2-[(e)-3-[9-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2CC3COCC(N3CC=3C=CC(F)=CC=3)C2)=C1NC(C)=O XKLXSHKFDPEOPK-VMPITWQZSA-N 0.000 claims 1
- DLTBLNKGEFXDKX-RMKNXTFCSA-N n-[5-chloro-2-[(e)-3-[9-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]cyclopropanecarboxamide Chemical compound C1CC1C(=O)NC=1C=C(Cl)C(OC)=CC=1\C=C\C(=O)N(C1)CC2COCC1N2CC1=CC=C(F)C=C1 DLTBLNKGEFXDKX-RMKNXTFCSA-N 0.000 claims 1
- UEHWRIMPCKMLPT-VMPITWQZSA-N n-[5-chloro-2-[(e)-3-[9-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]methanesulfonamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2CC3COCC(N3CC=3C=CC(F)=CC=3)C2)=C1NS(C)(=O)=O UEHWRIMPCKMLPT-VMPITWQZSA-N 0.000 claims 1
- XDBJLDLESZNRBA-QPJJXVBHSA-N n-[5-chloro-2-[(e)-3-[9-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl]-3-oxoprop-1-enyl]-4-pyrazin-2-ylphenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C=2N=CC=NC=2)C=C1\C=C\C(=O)N(C1)CC2COCC1N2CC1=CC=C(F)C=C1 XDBJLDLESZNRBA-QPJJXVBHSA-N 0.000 claims 1
- SXRZRBPNJLQQNH-JXMROGBWSA-N n-[5-chloro-2-[(e)-3-[9-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl]-3-oxoprop-1-enyl]-4-pyridin-2-ylphenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(C=2N=CC=CC=2)C=C1\C=C\C(=O)N(C1)CC2COCC1N2CC1=CC=C(F)C=C1 SXRZRBPNJLQQNH-JXMROGBWSA-N 0.000 claims 1
- AXPWVWCKQMKJRM-WEVVVXLNSA-N n-[5-chloro-2-[(e)-3-[9-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1CC(N2CC=3C=CC(F)=CC=3)COCC2C1 AXPWVWCKQMKJRM-WEVVVXLNSA-N 0.000 claims 1
- HYNXCKYSHPLVFT-RMKNXTFCSA-N n-[5-chloro-2-[(e)-3-[9-[(4-fluorophenyl)methyl]-7-methyl-3,7,9-triazabicyclo[3.3.1]nonan-3-yl]-3-oxoprop-1-enyl]-4-methylphenyl]methanesulfonamide Chemical compound C1N(C)CC2CN(C(=O)\C=C\C=3C(=CC(Cl)=C(C)C=3)NS(C)(=O)=O)CC1N2CC1=CC=C(F)C=C1 HYNXCKYSHPLVFT-RMKNXTFCSA-N 0.000 claims 1
- BBFBEPUPJCNGMQ-UHFFFAOYSA-N n-[5-chloro-2-[2-[3-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-2-oxoethoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1OCC(=O)N1C2CNCC1CN(CC=1C=CC(F)=CC=1)C2 BBFBEPUPJCNGMQ-UHFFFAOYSA-N 0.000 claims 1
- GSTPQUPZCKNPSI-UHFFFAOYSA-N n-[5-chloro-2-[2-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-2-oxoethoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1OCC(=O)N1C2COCC1CN(CC=1C=CC(F)=CC=1)C2 GSTPQUPZCKNPSI-UHFFFAOYSA-N 0.000 claims 1
- KCGPVSZXLIIQKV-UHFFFAOYSA-N n-[5-chloro-2-[2-[9-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonan-3-yl]-2-oxoethoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1OCC(=O)N1CC(N2CC=3C=CC(F)=CC=3)CNCC2C1 KCGPVSZXLIIQKV-UHFFFAOYSA-N 0.000 claims 1
- DYIARAXPMGPHCD-UHFFFAOYSA-N n-[5-chloro-2-[2-[9-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl]-2-oxoethoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1OCC(=O)N1CC(N2CC=3C=CC(F)=CC=3)COCC2C1 DYIARAXPMGPHCD-UHFFFAOYSA-N 0.000 claims 1
- CXFMHQODQQYCFB-UHFFFAOYSA-N n-[5-chloro-2-[3-[7-[(4-fluorophenyl)methyl]-3-methylsulfonyl-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(C=CC(=O)N2C3CN(CC=4C=CC(F)=CC=4)CC2CN(C3)S(C)(=O)=O)=C1NC(C)=O CXFMHQODQQYCFB-UHFFFAOYSA-N 0.000 claims 1
- JDBAQOZZZQVAMY-RMKNXTFCSA-N n-[5-chloro-4-(cyclopropylmethoxy)-2-[(e)-3-[7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C1=C(\C=C\C(=O)N2C3COCC2CN(CC=2C=CC(F)=CC=2)C3)C(NC(=O)C)=CC(Cl)=C1OCC1CC1 JDBAQOZZZQVAMY-RMKNXTFCSA-N 0.000 claims 1
- NUYLKDSKMMDXMT-IZZDOVSWSA-N n-[5-chloro-4-ethoxy-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C1=C(Cl)C(OCC)=CC(\C=C\C(=O)N2C3CCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NC(C)=O NUYLKDSKMMDXMT-IZZDOVSWSA-N 0.000 claims 1
- PYRKRHZMDKNYGZ-IZZDOVSWSA-N n-[5-chloro-4-ethoxy-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]methanesulfonamide Chemical compound C1=C(Cl)C(OCC)=CC(\C=C\C(=O)N2C3CCC2CN(CC=2C=CC(F)=CC=2)C3)=C1NS(C)(=O)=O PYRKRHZMDKNYGZ-IZZDOVSWSA-N 0.000 claims 1
- JKFSRYXCSMNBTB-RUDMXATFSA-N n-[5-chloro-4-fluoro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=C(F)C=C1\C=C\C(=O)N1C2CCC1CN(CC=1C=CC(F)=CC=1)C2 JKFSRYXCSMNBTB-RUDMXATFSA-N 0.000 claims 1
- OJNVVUCXMWLEHS-VMPITWQZSA-N n-[5-chloro-4-fluoro-2-[(e)-3-[3-[(4-fluorophenyl)methyl]-7-methyl-3,7,9-triazabicyclo[3.3.1]nonan-9-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C1C(N2C(=O)\C=C\C=3C(=CC(Cl)=C(F)C=3)NC(C)=O)CN(C)CC2CN1CC1=CC=C(F)C=C1 OJNVVUCXMWLEHS-VMPITWQZSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000002285 radioactive effect Effects 0.000 claims 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 1
- VEMVTHSYRUSLKJ-UHFFFAOYSA-N tert-butyl 7-[2-(2-acetamido-4-chlorophenoxy)acetyl]-9-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonane-3-carboxylate Chemical compound CC(=O)NC1=CC(Cl)=CC=C1OCC(=O)N1CC(N2CC=3C=CC(F)=CC=3)CN(C(=O)OC(C)(C)C)CC2C1 VEMVTHSYRUSLKJ-UHFFFAOYSA-N 0.000 claims 1
- HPNWKORERFGQGI-UHFFFAOYSA-N tert-butyl 9-[2-(2-acetamido-4-chlorophenoxy)acetyl]-7-[(4-fluorophenyl)methyl]-3,7,9-triazabicyclo[3.3.1]nonane-3-carboxylate Chemical compound CC(=O)NC1=CC(Cl)=CC=C1OCC(=O)N1C2CN(CC=3C=CC(F)=CC=3)CC1CN(C(=O)OC(C)(C)C)C2 HPNWKORERFGQGI-UHFFFAOYSA-N 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
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- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012981 Hank's balanced salt solution Substances 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- 0 C*(C(C1CCC2*c3ccc(*)cc3)N3C(CCl)=O)C2[C@]13I Chemical compound C*(C(C1CCC2*c3ccc(*)cc3)N3C(CCl)=O)C2[C@]13I 0.000 description 1
- ICPUJELHXWTDFQ-UHFFFAOYSA-N CCCCCC(CC)NC1=CC=C(C=C1)F Chemical compound CCCCCC(CC)NC1=CC=C(C=C1)F ICPUJELHXWTDFQ-UHFFFAOYSA-N 0.000 description 1
- 108700012434 CCL3 Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- OUVXYXNWSVIOSJ-UHFFFAOYSA-N Fluo-4 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C2=C3C=C(F)C(=O)C=C3OC3=CC(O)=C(F)C=C32)N(CC(O)=O)CC(O)=O)=C1 OUVXYXNWSVIOSJ-UHFFFAOYSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000001275 ca(2+)-mobilization Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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| Application Number | Priority Date | Filing Date | Title |
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| GBGB0409236.7A GB0409236D0 (en) | 2004-04-26 | 2004-04-26 | Organic compounds |
| PCT/EP2005/004422 WO2005103054A2 (en) | 2004-04-26 | 2005-04-25 | Bridged piperazine and piperidine derivatives as ccri antagonists |
Publications (2)
| Publication Number | Publication Date |
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| JP2007534678A JP2007534678A (ja) | 2007-11-29 |
| JP2007534678A5 true JP2007534678A5 (https=) | 2010-08-05 |
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| EP (1) | EP1794164A2 (https=) |
| JP (1) | JP2007534678A (https=) |
| KR (2) | KR100845356B1 (https=) |
| CN (1) | CN101238131A (https=) |
| AR (1) | AR052397A1 (https=) |
| AU (1) | AU2005235724B2 (https=) |
| BR (1) | BRPI0510313A (https=) |
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| RU (1) | RU2383548C2 (https=) |
| TW (1) | TW200603805A (https=) |
| WO (1) | WO2005103054A2 (https=) |
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| ES2712211T3 (es) | 2013-06-20 | 2019-05-09 | Bayer Cropscience Ag | Derivados de arilsulfuro y arilsulfóxido acaricidas e insecticidas |
| MX368059B (es) | 2013-07-18 | 2019-09-18 | Novartis Ag | Inhibidores de autotaxina que comprenden un núcleo de anillo heteroaromático de bencil-amida cíclica. |
| CN115286637B (zh) * | 2022-08-11 | 2024-03-22 | 成都金博汇康医药科技有限公司 | 三氮杂桥环化合物及其中间体化合物、制备方法和应用 |
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| US6207665B1 (en) * | 1997-06-12 | 2001-03-27 | Schering Aktiengesellschaft | Piperazine derivatives and their use as anti-inflammatory agents |
| US6818643B1 (en) * | 1999-12-08 | 2004-11-16 | Bristol-Myers Squibb Company | Neurotrophic bicyclic diamides |
| AU2001292160A1 (en) * | 2000-10-19 | 2002-04-29 | Pfizer Products Inc. | Bridged piperazine derivatives |
| UY27003A1 (es) * | 2000-11-06 | 2002-07-31 | Schering Ag | Productos radiofarmacéuticos para el diagnóstico de la enfermedad de alzheimer |
| JPWO2002100833A1 (ja) * | 2001-06-12 | 2004-09-24 | 住友製薬株式会社 | Ｒｈｏキナーゼ阻害剤 |
| AP2005003196A0 (en) * | 2002-07-18 | 2005-03-31 | Pfizer Prod Inc | Bicyclic piperidine derivatives as antagonists of the CCR1 chemokine receptor. |
| GB0224917D0 (en) * | 2002-10-25 | 2002-12-04 | Novartis Ag | Organic compounds |
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2004
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2005
- 2005-04-25 CA CA002559917A patent/CA2559917A1/en not_active Abandoned
- 2005-04-25 WO PCT/EP2005/004422 patent/WO2005103054A2/en not_active Ceased
- 2005-04-25 CN CNA2005800132391A patent/CN101238131A/zh active Pending
- 2005-04-25 JP JP2007508868A patent/JP2007534678A/ja not_active Ceased
- 2005-04-25 KR KR1020067022181A patent/KR100845356B1/ko not_active Expired - Fee Related
- 2005-04-25 BR BRPI0510313-4A patent/BRPI0510313A/pt not_active IP Right Cessation
- 2005-04-25 EP EP05737794A patent/EP1794164A2/en not_active Withdrawn
- 2005-04-25 RU RU2006141702/04A patent/RU2383548C2/ru not_active IP Right Cessation
- 2005-04-25 AU AU2005235724A patent/AU2005235724B2/en not_active Ceased
- 2005-04-25 MX MXPA06012380A patent/MXPA06012380A/es not_active Application Discontinuation
- 2005-04-25 US US10/599,819 patent/US20070196270A1/en not_active Abandoned
- 2005-04-25 KR KR1020087002184A patent/KR20080015151A/ko not_active Ceased
- 2005-04-25 AR ARP050101623A patent/AR052397A1/es unknown
- 2005-04-25 TW TW094113108A patent/TW200603805A/zh unknown
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