JP2006505575A5 - - Google Patents
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- Publication number
- JP2006505575A5 JP2006505575A5 JP2004545990A JP2004545990A JP2006505575A5 JP 2006505575 A5 JP2006505575 A5 JP 2006505575A5 JP 2004545990 A JP2004545990 A JP 2004545990A JP 2004545990 A JP2004545990 A JP 2004545990A JP 2006505575 A5 JP2006505575 A5 JP 2006505575A5
- Authority
- JP
- Japan
- Prior art keywords
- fluorobenzyl
- chloro
- oxopropenyl
- methylpiperazin
- phenyl
- 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.)
- Pending
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- -1 hydroxy, amino Chemical group 0.000 claims description 26
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 230000008878 coupling Effects 0.000 claims 5
- 238000010168 coupling process Methods 0.000 claims 5
- 238000005859 coupling reaction Methods 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 2
- WZEFFFYJQFGJBZ-QPGLYAHGSA-N 3-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]-1,3-diazaspiro[4.4]nonane-2,4-dione Chemical compound O=C1NC2(CCCC2)C(=O)N1C=1C=C(Cl)C(OC)=CC=1\C=C\C(=O)N([C@@H](C1)C)CCN1CC1=CC=C(F)C=C1 WZEFFFYJQFGJBZ-QPGLYAHGSA-N 0.000 claims 2
- HCBCECIUYUWZEF-PYUISTEWSA-N 3-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1NC(C)(C)C(=O)N1C=1C=C(Cl)C(OC)=CC=1\C=C\C(=O)N([C@@H](C1)C)CCN1CC1=CC=C(F)C=C1 HCBCECIUYUWZEF-PYUISTEWSA-N 0.000 claims 2
- ZBJFUFFNMQPNJA-CDVVCGDMSA-N 3-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]imidazolidine-2,4-dione Chemical compound O=C1CNC(=O)N1C=1C=C(Cl)C(OC)=CC=1\C=C\C(=O)N([C@@H](C1)C)CCN1CC1=CC=C(F)C=C1 ZBJFUFFNMQPNJA-CDVVCGDMSA-N 0.000 claims 2
- IATARYFOTVWRTR-QPGLYAHGSA-N 3-[5-chloro-4-fluoro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]-1,3-diazaspiro[4.5]decane-2,4-dione Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=C(F)C=2)N2C(C3(CCCCC3)NC2=O)=O)C)N1CC1=CC=C(F)C=C1 IATARYFOTVWRTR-QPGLYAHGSA-N 0.000 claims 2
- ODHCTXKNWHHXJC-UHFFFAOYSA-N 5-oxoproline Chemical compound OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims 2
- SOQTZVDCTDWUPS-JHCSKLMMSA-N [5-chloro-2-[(e)-3-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound C([C@@H](C)N(C[C@@H]1C)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(N)=O)N1CC1=CC=C(F)C=C1 SOQTZVDCTDWUPS-JHCSKLMMSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- VYKDORADUDIZTO-RMGWEFQESA-N (2r)-n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]-1-propan-2-ylpyrrolidine-2-carboxamide Chemical compound O=C([C@@H]1N(CCC1)C(C)C)NC=1C=C(Cl)C(OC)=CC=1\C=C\C(=O)N([C@@H](C1)C)CCN1CC1=CC=C(F)C=C1 VYKDORADUDIZTO-RMGWEFQESA-N 0.000 claims 1
- XPDLYCFFLURWIW-FSYQOESSSA-N (2s)-1-acetyl-n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]pyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(CCC1)C(C)=O)NC=1C=C(Cl)C(OC)=CC=1\C=C\C(=O)N([C@@H](C1)C)CCN1CC1=CC=C(F)C=C1 XPDLYCFFLURWIW-FSYQOESSSA-N 0.000 claims 1
- VYKDORADUDIZTO-KLVBPWCTSA-N (2s)-n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]-1-propan-2-ylpyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(CCC1)C(C)C)NC=1C=C(Cl)C(OC)=CC=1\C=C\C(=O)N([C@@H](C1)C)CCN1CC1=CC=C(F)C=C1 VYKDORADUDIZTO-KLVBPWCTSA-N 0.000 claims 1
- CRSNSRGEINTVBH-ONWCSZCQSA-N (2s,4r)-1-acetyl-n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]-4-hydroxypyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(C[C@H](O)C1)C(C)=O)NC=1C=C(Cl)C(OC)=CC=1\C=C\C(=O)N([C@@H](C1)C)CCN1CC1=CC=C(F)C=C1 CRSNSRGEINTVBH-ONWCSZCQSA-N 0.000 claims 1
- OMKWFGOUVCFSCC-BJMVGYQFSA-N 1-[4-chloro-2-[(e)-3-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]-3-cyano-1-methylsulfanylthiourea Chemical compound N#CNC(=S)N(SC)C1=CC=C(Cl)C=C1\C=C\C(=O)N1C(C)CN(CC=2C=CC(F)=CC=2)CC1 OMKWFGOUVCFSCC-BJMVGYQFSA-N 0.000 claims 1
- AYHZDLKXCIVTJB-HYMNUWHNSA-N 1-[5-chloro-2-[(e)-3-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]-1-cyanoguanidine Chemical compound C([C@@H](C)N(C[C@@H]1C)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)N(C#N)C(N)=N)N1CC1=CC=C(F)C=C1 AYHZDLKXCIVTJB-HYMNUWHNSA-N 0.000 claims 1
- DBSWOHVHEBJNNB-FTUXVVSKSA-N 1-[[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]methyl]-3-oxa-1-azaspiro[4.4]nonan-2-one Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)CN2C3(CCCC3)COC2=O)C)N1CC1=CC=C(F)C=C1 DBSWOHVHEBJNNB-FTUXVVSKSA-N 0.000 claims 1
- QMFLNKYTVKTBPL-YRNVUSSQSA-N 1-[[5-chloro-2-[(e)-3-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]methyl]pyrrolidin-2-one Chemical compound C1CN(C(=O)\C=C\C=2C(=CC(Cl)=CC=2)CN2C(CCC2)=O)C(C)CN1CC1=CC=C(F)C=C1 QMFLNKYTVKTBPL-YRNVUSSQSA-N 0.000 claims 1
- HBZKXRGNVHYDAW-CLOLKSBNSA-N 1-acetyl-n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]piperidine-4-carboxamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(=O)C2CCN(CC2)C(C)=O)C)N1CC1=CC=C(F)C=C1 HBZKXRGNVHYDAW-CLOLKSBNSA-N 0.000 claims 1
- FGVPZYAYLXTCAB-UFUQCMIWSA-N 1-cyano-2-[3-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]naphthalen-2-yl]guanidine Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC3=CC=CC=C3C=2)NC(=N)NC#N)C)N1CC1=CC=C(F)C=C1 FGVPZYAYLXTCAB-UFUQCMIWSA-N 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- FPQHZVCQEPZNML-OJLWIZQOSA-N 2-(dimethylamino)-n-[7-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]quinolin-6-yl]acetamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC3=CC=CN=C3C=2)NC(=O)CN(C)C)C)N1CC1=CC=C(F)C=C1 FPQHZVCQEPZNML-OJLWIZQOSA-N 0.000 claims 1
- FGWGUTDBNUTFLC-RUDMXATFSA-N 2-[4-chloro-2-[(e)-3-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]-1-cyanoguanidine Chemical compound C1CN(C(=O)\C=C\C=2C(=CC=C(Cl)C=2)NC(=N)NC#N)C(C)CN1CC1=CC=C(F)C=C1 FGWGUTDBNUTFLC-RUDMXATFSA-N 0.000 claims 1
- XRLWQCORWSVYER-DXWDOBMASA-N 2-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]-1-cyanoguanidine Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(=N)NC#N)C)N1CC1=CC=C(F)C=C1 XRLWQCORWSVYER-DXWDOBMASA-N 0.000 claims 1
- HQOFSHQNAJACJB-YXMGTMDOSA-N 3-[5-chloro-4-fluoro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=C(F)C=2)N2C(C(C)(C)NC2=O)=O)C)N1CC1=CC=C(F)C=C1 HQOFSHQNAJACJB-YXMGTMDOSA-N 0.000 claims 1
- LNKPAJBTADDYTN-WGLAMXGCSA-N 3-[[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]methyl]-1-methylimidazolidine-2,4-dione Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)CN2C(N(C)CC2=O)=O)C)N1CC1=CC=C(F)C=C1 LNKPAJBTADDYTN-WGLAMXGCSA-N 0.000 claims 1
- LKEPWEUKYREVHI-JGZYNSJSSA-N 3-[[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]methyl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)CN2C(C(C)(C)NC2=O)=O)C)N1CC1=CC=C(F)C=C1 LKEPWEUKYREVHI-JGZYNSJSSA-N 0.000 claims 1
- MLAQWQMHNDHAEO-YRNVUSSQSA-N 5-chloro-2-[(e)-3-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC(Cl)=CC=C1\C=C\C(=O)N1C(C)CN(CC=2C=CC(F)=CC=2)CC1 MLAQWQMHNDHAEO-YRNVUSSQSA-N 0.000 claims 1
- CPSGOSKGUBWDKR-WEVVVXLNSA-N 5-chloro-2-[(e)-3-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]benzoic acid Chemical compound C1CN(C(=O)\C=C\C=2C(=CC(Cl)=CC=2)C(O)=O)C(C)CN1CC1=CC=C(F)C=C1 CPSGOSKGUBWDKR-WEVVVXLNSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N CH2-hydantoin Natural products O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 1
- 241000257303 Hymenoptera Species 0.000 claims 1
- WSCDKETWDCZPNR-VEGGFIAOSA-N [3-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]naphthalen-2-yl]urea Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC3=CC=CC=C3C=2)NC(N)=O)C)N1CC1=CC=C(F)C=C1 WSCDKETWDCZPNR-VEGGFIAOSA-N 0.000 claims 1
- ITWOCFFVCHJDNR-RUDMXATFSA-N [4-chloro-2-[(e)-3-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]sulfonylurea Chemical compound C1CN(C(=O)\C=C\C=2C(=CC=C(Cl)C=2)S(=O)(=O)NC(N)=O)C(C)CN1CC1=CC=C(F)C=C1 ITWOCFFVCHJDNR-RUDMXATFSA-N 0.000 claims 1
- ZLYQJADBJIMEME-CLOLKSBNSA-N [5-chloro-2-[(e)-3-[(2r)-2-ethyl-4-[(4-fluorophenyl)methyl]piperazin-1-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(N)=O)CC)N1CC1=CC=C(F)C=C1 ZLYQJADBJIMEME-CLOLKSBNSA-N 0.000 claims 1
- ZVONRCNOYWVUHU-BTKRWWFXSA-N [5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-(trifluoromethoxy)phenyl]urea Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=C(OC(F)(F)F)C=2)NC(N)=O)C)N1CC1=CC=C(F)C=C1 ZVONRCNOYWVUHU-BTKRWWFXSA-N 0.000 claims 1
- QAOMRPSMCCPFQL-SBJJXXPASA-N [5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]urea Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2[C@@H](CN(CC=3C=CC(F)=CC=3)CC2)C)=C1NC(N)=O QAOMRPSMCCPFQL-SBJJXXPASA-N 0.000 claims 1
- SMUIBVXQXIDYSQ-FUVBFXSKSA-N [5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(N)=O)C)N1CC1=CC=C(F)C=C1 SMUIBVXQXIDYSQ-FUVBFXSKSA-N 0.000 claims 1
- MSBZLJODPCVFKE-UKTKYZJWSA-N [5-chloro-2-[(e)-3-[(2s)-4-[(4-fluorophenyl)methyl]-2-(hydroxymethyl)piperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]urea Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2[C@@H](CN(CC=3C=CC(F)=CC=3)CC2)CO)=C1NC(N)=O MSBZLJODPCVFKE-UKTKYZJWSA-N 0.000 claims 1
- SMUIBVXQXIDYSQ-BOSPYUDASA-N [5-chloro-2-[(e)-3-[(2s)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound C([C@@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(N)=O)C)N1CC1=CC=C(F)C=C1 SMUIBVXQXIDYSQ-BOSPYUDASA-N 0.000 claims 1
- SOQTZVDCTDWUPS-ZLAMNEIASA-N [5-chloro-2-[(e)-3-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(N)=O)N1CC1=CC=C(F)C=C1 SOQTZVDCTDWUPS-ZLAMNEIASA-N 0.000 claims 1
- BZEZCSINMFCJHB-XBXARRHUSA-N [5-chloro-2-[(e)-3-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound NC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1CCN(CC=2C=CC(F)=CC=2)CC1 BZEZCSINMFCJHB-XBXARRHUSA-N 0.000 claims 1
- NWPBAXBCNUZTJE-YXMGTMDOSA-N [5-chloro-4-ethoxy-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound C1=C(Cl)C(OCC)=CC(\C=C\C(=O)N2[C@@H](CN(CC=3C=CC(F)=CC=3)CC2)C)=C1NC(N)=O NWPBAXBCNUZTJE-YXMGTMDOSA-N 0.000 claims 1
- VDBBMZZUTKNSFN-BTKRWWFXSA-N [5-chloro-4-fluoro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]urea Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=C(F)C=2)NC(N)=O)C)N1CC1=CC=C(F)C=C1 VDBBMZZUTKNSFN-BTKRWWFXSA-N 0.000 claims 1
- OMBMUHZEGOVDIC-RCMYXZNBSA-N [6-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]quinolin-7-yl]urea Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC3=NC=CC=C3C=2)NC(N)=O)C)N1CC1=CC=C(F)C=C1 OMBMUHZEGOVDIC-RCMYXZNBSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- MUSSQFQEEBNWDS-YRNVUSSQSA-N ethyl 4-[[5-chloro-2-[(e)-3-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]benzoyl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC(=O)C1=CC(Cl)=CC=C1\C=C\C(=O)N1C(C)CN(CC=2C=CC(F)=CC=2)CC1 MUSSQFQEEBNWDS-YRNVUSSQSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 239000011021 lapis lazuli Substances 0.000 claims 1
- IYBYDKQYPMIBPG-XFSDTALMSA-N methyl (2s,4r)-1-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]benzoyl]-4-hydroxypyrrolidine-2-carboxylate Chemical compound COC(=O)[C@@H]1C[C@@H](O)CN1C(=O)C1=CC(Cl)=CC=C1\C=C\C(=O)N1[C@H](C)CN(CC=2C=CC(F)=CC=2)CC1 IYBYDKQYPMIBPG-XFSDTALMSA-N 0.000 claims 1
- WJNGLDNTUGTQJT-UXBLZVDNSA-N methyl 2-[5-chloro-2-[(e)-3-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetate Chemical compound COC(=O)CC1=CC(Cl)=CC=C1\C=C\C(=O)N1C(C)CN(CC=2C=CC(F)=CC=2)CC1 WJNGLDNTUGTQJT-UXBLZVDNSA-N 0.000 claims 1
- QTNLSMSKXZFKML-UXBLZVDNSA-N methyl 5-chloro-2-[(e)-3-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]benzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1\C=C\C(=O)N1C(C)CN(CC=2C=CC(F)=CC=2)CC1 QTNLSMSKXZFKML-UXBLZVDNSA-N 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- YCZSPJUKENKJMZ-GXDHUFHOSA-N n-(1-benzylpiperidin-4-yl)-5-chloro-2-[(e)-3-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]benzamide Chemical compound C1CN(C(=O)\C=C\C=2C(=CC(Cl)=CC=2)C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)C(C)CN1CC1=CC=C(F)C=C1 YCZSPJUKENKJMZ-GXDHUFHOSA-N 0.000 claims 1
- MQODCWGPPFRIEF-AEVNEEFTSA-N n-[2-[(e)-3-[(2r)-2-(aminomethyl)-4-[(4-fluorophenyl)methyl]piperazin-1-yl]-3-oxoprop-1-enyl]-5-chlorophenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1[C@H](CN)CN(CC=2C=CC(F)=CC=2)CC1 MQODCWGPPFRIEF-AEVNEEFTSA-N 0.000 claims 1
- INCGOJTXDMDAID-LNLBBOMNSA-N n-[2-[(e)-3-[(2s)-2-acetyl-4-[(4-fluorophenyl)methyl]piperazin-1-yl]-3-oxoprop-1-enyl]-5-chlorophenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1[C@H](C(C)=O)CN(CC=2C=CC(F)=CC=2)CC1 INCGOJTXDMDAID-LNLBBOMNSA-N 0.000 claims 1
- OKPDPHQVVCXCIO-VSRDTVRMSA-N n-[3-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]naphthalen-2-yl]acetamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC3=CC=CC=C3C=2)NC(C)=O)C)N1CC1=CC=C(F)C=C1 OKPDPHQVVCXCIO-VSRDTVRMSA-N 0.000 claims 1
- WMNVCJHUWOKRDG-BJMVGYQFSA-N n-[4-chloro-2-[(e)-3-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C1CN(C(=O)\C=C\C=2C(=CC=C(Cl)C=2)NC(C)=O)C(C)CN1CC1=CC=C(F)C=C1 WMNVCJHUWOKRDG-BJMVGYQFSA-N 0.000 claims 1
- LPZSTSAAMPGUEG-ICKBMGCOSA-N n-[5-chloro-2-[(e)-3-[(2r)-2-ethyl-4-[(4-fluorophenyl)methyl]piperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(C)=O)CC)N1CC1=CC=C(F)C=C1 LPZSTSAAMPGUEG-ICKBMGCOSA-N 0.000 claims 1
- FNPXZIBPFRYOLV-QPGLYAHGSA-N n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-(2-methylpropoxy)phenyl]acetamide Chemical compound C1=C(Cl)C(OCC(C)C)=CC(\C=C\C(=O)N2[C@@H](CN(CC=3C=CC(F)=CC=3)CC2)C)=C1NC(C)=O FNPXZIBPFRYOLV-QPGLYAHGSA-N 0.000 claims 1
- VODYKHASXWEHLJ-SBJJXXPASA-N n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-(trifluoromethoxy)phenyl]acetamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=C(OC(F)(F)F)C=2)NC(C)=O)C)N1CC1=CC=C(F)C=C1 VODYKHASXWEHLJ-SBJJXXPASA-N 0.000 claims 1
- JKAIKDYLOFOXMP-YXMGTMDOSA-N n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2[C@@H](CN(CC=3C=CC(F)=CC=3)CC2)C)=C1NC(C)=O JKAIKDYLOFOXMP-YXMGTMDOSA-N 0.000 claims 1
- MXFQQMJDQHFGCV-MTCRFPMVSA-N n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]morpholine-4-carboxamide Chemical compound C1COCCN1C(=O)NC=1C=C(Cl)C(OC)=CC=1\C=C\C(=O)N([C@@H](C1)C)CCN1CC1=CC=C(F)C=C1 MXFQQMJDQHFGCV-MTCRFPMVSA-N 0.000 claims 1
- GYQIZRVGOBQSGG-QPGLYAHGSA-N n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]pyrrolidine-1-carboxamide Chemical compound C1CCCN1C(=O)NC=1C=C(Cl)C(OC)=CC=1\C=C\C(=O)N([C@@H](C1)C)CCN1CC1=CC=C(F)C=C1 GYQIZRVGOBQSGG-QPGLYAHGSA-N 0.000 claims 1
- AELMJFWYSUOUGF-MTCRFPMVSA-N n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-morpholin-4-ylphenyl]acetamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=C(N3CCOCC3)C=2)NC(C)=O)C)N1CC1=CC=C(F)C=C1 AELMJFWYSUOUGF-MTCRFPMVSA-N 0.000 claims 1
- BRYSQJWKZBDJLI-RUJXFNLJSA-N n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-propan-2-yloxyphenyl]acetamide Chemical compound C1=C(Cl)C(OC(C)C)=CC(\C=C\C(=O)N2[C@@H](CN(CC=3C=CC(F)=CC=3)CC2)C)=C1NC(C)=O BRYSQJWKZBDJLI-RUJXFNLJSA-N 0.000 claims 1
- ZMNMGRMQVMIYTL-WGLAMXGCSA-N n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2N=CN(C)C=2)C)N1CC1=CC=C(F)C=C1 ZMNMGRMQVMIYTL-WGLAMXGCSA-N 0.000 claims 1
- LXIRNICRTOIEAD-HFTQHKIXSA-N n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]-2-oxoimidazolidine-1-carboxamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(=O)N2C(NCC2)=O)C)N1CC1=CC=C(F)C=C1 LXIRNICRTOIEAD-HFTQHKIXSA-N 0.000 claims 1
- DUFKTZBQJIHIAQ-VGZDNEPHSA-N n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(C)=O)C)N1CC1=CC=C(F)C=C1 DUFKTZBQJIHIAQ-VGZDNEPHSA-N 0.000 claims 1
- FQMGPFFTAOXTCV-VGZDNEPHSA-N n-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]methanesulfonamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NS(C)(=O)=O)C)N1CC1=CC=C(F)C=C1 FQMGPFFTAOXTCV-VGZDNEPHSA-N 0.000 claims 1
- TXFDENXEXABBDW-NGXUEJOTSA-N n-[5-chloro-2-[(e)-3-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2[C@@H](CN(CC=3C=CC(F)=CC=3)[C@@H](C)C2)C)=C1NC(C)=O TXFDENXEXABBDW-NGXUEJOTSA-N 0.000 claims 1
- PENYPUDAOPAQLW-NGXUEJOTSA-N n-[5-chloro-2-[(e)-3-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]methanesulfonamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2[C@@H](CN(CC=3C=CC(F)=CC=3)[C@@H](C)C2)C)=C1NS(C)(=O)=O PENYPUDAOPAQLW-NGXUEJOTSA-N 0.000 claims 1
- MDORNLMADCVHFZ-CZPJPAAGSA-N n-[5-chloro-2-[(e)-3-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C([C@@H](C)N(C[C@@H]1C)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(C)=O)N1CC1=CC=C(F)C=C1 MDORNLMADCVHFZ-CZPJPAAGSA-N 0.000 claims 1
- JFDPBVXFIHEZOX-CZPJPAAGSA-N n-[5-chloro-2-[(e)-3-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]methanesulfonamide Chemical compound C([C@@H](C)N(C[C@@H]1C)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NS(C)(=O)=O)N1CC1=CC=C(F)C=C1 JFDPBVXFIHEZOX-CZPJPAAGSA-N 0.000 claims 1
- PEJYMIUOXJMYOR-FKIZTMCRSA-N n-[5-chloro-2-[(e)-3-[(2s)-4-[(4-fluorophenyl)methyl]-2-(hydroxymethyl)piperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2[C@@H](CN(CC=3C=CC(F)=CC=3)CC2)CO)=C1NC(C)=O PEJYMIUOXJMYOR-FKIZTMCRSA-N 0.000 claims 1
- OGAAHLSBWGMDAH-MEQKGCOVSA-N n-[5-chloro-2-[(e)-3-[(2s)-4-[(4-fluorophenyl)methyl]-2-(hydroxymethyl)piperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxyphenyl]methanesulfonamide Chemical compound C1=C(Cl)C(OC)=CC(\C=C\C(=O)N2[C@@H](CN(CC=3C=CC(F)=CC=3)CC2)CO)=C1NS(C)(=O)=O OGAAHLSBWGMDAH-MEQKGCOVSA-N 0.000 claims 1
- LCDYBFVSPXSNHQ-OWLMGLOSSA-N n-[5-chloro-2-[(e)-3-[(2s)-4-[(4-fluorophenyl)methyl]-2-(hydroxymethyl)piperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1[C@H](CO)CN(CC=2C=CC(F)=CC=2)CC1 LCDYBFVSPXSNHQ-OWLMGLOSSA-N 0.000 claims 1
- SKPCBVVMWXFRBX-QNFQYUBJSA-N n-[5-chloro-2-[(e)-3-[(2s)-4-[(4-fluorophenyl)methyl]-2-[(1s)-1-hydroxyethyl]piperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(C)=O)[C@@H](O)C)N1CC1=CC=C(F)C=C1 SKPCBVVMWXFRBX-QNFQYUBJSA-N 0.000 claims 1
- DUFKTZBQJIHIAQ-DHINHOHASA-N n-[5-chloro-2-[(e)-3-[(2s)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C([C@@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(C)=O)C)N1CC1=CC=C(F)C=C1 DUFKTZBQJIHIAQ-DHINHOHASA-N 0.000 claims 1
- MDORNLMADCVHFZ-QZKWLWDQSA-N n-[5-chloro-2-[(e)-3-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(C)=O)N1CC1=CC=C(F)C=C1 MDORNLMADCVHFZ-QZKWLWDQSA-N 0.000 claims 1
- KQRZTSQFPNLYIL-KVKRHKIDSA-N n-[5-chloro-2-[(e)-3-[(2s,5s)-4-[(4-fluorophenyl)methyl]-5-methyl-2-(phenylmethoxymethyl)piperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C([C@H]1N(C[C@@H](N(C1)CC=1C=CC(F)=CC=1)C)C(=O)\C=C\C=1C(=CC(Cl)=CC=1)NC(C)=O)OCC1=CC=CC=C1 KQRZTSQFPNLYIL-KVKRHKIDSA-N 0.000 claims 1
- QJZDTGMQHBUKDO-VMPITWQZSA-N n-[5-chloro-2-[(e)-3-[4-[(2,4-difluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C1CN(C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(C)=O)C(C)CN1CC1=CC=C(F)C=C1F QJZDTGMQHBUKDO-VMPITWQZSA-N 0.000 claims 1
- WDNHYJMPVUCJAS-VQHVLOKHSA-N n-[5-chloro-2-[(e)-3-[4-[(3-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C1CN(C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(C)=O)C(C)CN1CC1=CC=CC(F)=C1 WDNHYJMPVUCJAS-VQHVLOKHSA-N 0.000 claims 1
- IFTAKZIIEOCMPH-UXBLZVDNSA-N n-[5-chloro-2-[(e)-3-[4-[(4-chlorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C1CN(C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(C)=O)C(C)CN1CC1=CC=C(Cl)C=C1 IFTAKZIIEOCMPH-UXBLZVDNSA-N 0.000 claims 1
- HIDICENMVRNHJQ-CSKARUKUSA-N n-[5-chloro-2-[(e)-3-[4-[(4-cyanophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C1CN(C(=O)\C=C\C=2C(=CC(Cl)=CC=2)NC(C)=O)C(C)CN1CC1=CC=C(C#N)C=C1 HIDICENMVRNHJQ-CSKARUKUSA-N 0.000 claims 1
- VRHDKJQVCPDYJB-WEVVVXLNSA-N n-[5-chloro-2-[(e)-3-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1\C=C\C(=O)N1CCN(CC=2C=CC(F)=CC=2)CC1 VRHDKJQVCPDYJB-WEVVVXLNSA-N 0.000 claims 1
- WQEXEUBTAAZZPM-CDVVCGDMSA-N n-[5-chloro-4-cyano-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=C(C#N)C=2)NC(C)=O)C)N1CC1=CC=C(F)C=C1 WQEXEUBTAAZZPM-CDVVCGDMSA-N 0.000 claims 1
- KWSXKISBXGOOGK-QQACWOFXSA-N n-[5-chloro-4-ethoxy-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]-5-oxopyrrolidine-2-carboxamide Chemical compound C1CC(=O)NC1C(=O)NC=1C=C(Cl)C(OCC)=CC=1\C=C\C(=O)N([C@@H](C1)C)CCN1CC1=CC=C(F)C=C1 KWSXKISBXGOOGK-QQACWOFXSA-N 0.000 claims 1
- DFEHALWAKUXBPW-PYUISTEWSA-N n-[5-chloro-4-ethoxy-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C1=C(Cl)C(OCC)=CC(\C=C\C(=O)N2[C@@H](CN(CC=3C=CC(F)=CC=3)CC2)C)=C1NC(C)=O DFEHALWAKUXBPW-PYUISTEWSA-N 0.000 claims 1
- ZMUIRRLZEHRHFC-PYUISTEWSA-N n-[5-chloro-4-ethoxy-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]methanesulfonamide Chemical compound C1=C(Cl)C(OCC)=CC(\C=C\C(=O)N2[C@@H](CN(CC=3C=CC(F)=CC=3)CC2)C)=C1NS(C)(=O)=O ZMUIRRLZEHRHFC-PYUISTEWSA-N 0.000 claims 1
- OZSXZVYEPTYQJL-SBJJXXPASA-N n-[5-chloro-4-fluoro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=C(F)C=2)NC(C)=O)C)N1CC1=CC=C(F)C=C1 OZSXZVYEPTYQJL-SBJJXXPASA-N 0.000 claims 1
- JTFRLPSCLRRZFU-SBJJXXPASA-N n-[5-chloro-4-fluoro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]methanesulfonamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=C(F)C=2)NS(C)(=O)=O)C)N1CC1=CC=C(F)C=C1 JTFRLPSCLRRZFU-SBJJXXPASA-N 0.000 claims 1
- MVIVWOSZVYNMQN-RUJXFNLJSA-N n-[6-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]quinolin-7-yl]acetamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC3=NC=CC=C3C=2)NC(C)=O)C)N1CC1=CC=C(F)C=C1 MVIVWOSZVYNMQN-RUJXFNLJSA-N 0.000 claims 1
- GCVJAGXXZDMXEC-RUJXFNLJSA-N n-[7-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]quinolin-6-yl]acetamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC3=CC=CN=C3C=2)NC(C)=O)C)N1CC1=CC=C(F)C=C1 GCVJAGXXZDMXEC-RUJXFNLJSA-N 0.000 claims 1
- HVXRKIFTIHRJAA-RUJXFNLJSA-N n-[7-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]quinolin-6-yl]methanesulfonamide Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC3=CC=CN=C3C=2)NS(C)(=O)=O)C)N1CC1=CC=C(F)C=C1 HVXRKIFTIHRJAA-RUJXFNLJSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- KUYNVQRFISRMIM-ZXXUSRDYSA-N tert-butyl 4-[2-[5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]phenyl]ethynyl]-4-hydroxypiperidine-1-carboxylate Chemical compound C([C@H](N(CC1)C(=O)\C=C\C=2C(=CC(Cl)=CC=2)C#CC2(O)CCN(CC2)C(=O)OC(C)(C)C)C)N1CC1=CC=C(F)C=C1 KUYNVQRFISRMIM-ZXXUSRDYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- STYGJQSPNBPHNT-ONEGZZNKSA-N methyl (e)-3-[2-amino-4-chloro-5-(2-methoxyethoxy)phenyl]prop-2-enoate Chemical compound COCCOC1=CC(\C=C\C(=O)OC)=C(N)C=C1Cl STYGJQSPNBPHNT-ONEGZZNKSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HSAVKZDJTHYQSR-ONEGZZNKSA-N (e)-3-[2-acetamido-4-chloro-5-(2-methoxyethoxy)phenyl]prop-2-enoic acid Chemical compound COCCOC1=CC(\C=C\C(O)=O)=C(NC(C)=O)C=C1Cl HSAVKZDJTHYQSR-ONEGZZNKSA-N 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- RVSFRTUQNOKXPC-YXMGTMDOSA-N methyl 5-chloro-2-[(e)-3-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-3-oxoprop-1-enyl]-4-methoxybenzoate Chemical compound COC(=O)C1=CC(Cl)=C(OC)C=C1\C=C\C(=O)N1[C@H](C)CN(CC=2C=CC(F)=CC=2)CC1 RVSFRTUQNOKXPC-YXMGTMDOSA-N 0.000 description 1
- LAXDTJRDBCETGC-UHFFFAOYSA-N methyl 5-chloro-2-hydroxy-4-methoxybenzoate Chemical compound COC(=O)C1=CC(Cl)=C(OC)C=C1O LAXDTJRDBCETGC-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0224917.5A GB0224917D0 (en) | 2002-10-25 | 2002-10-25 | Organic compounds |
| PCT/EP2003/011848 WO2004037796A2 (en) | 2002-10-25 | 2003-10-24 | 1-(4-benzyl-piperazin-1-yl)-3-phenyl-propenone derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006505575A JP2006505575A (ja) | 2006-02-16 |
| JP2006505575A5 true JP2006505575A5 (https=) | 2010-10-28 |
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| JP2004545990A Pending JP2006505575A (ja) | 2002-10-25 | 2003-10-24 | １−（４−ベンジルピペラジン−１−イル）−３−フェニルプロペノン誘導体 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7645760B2 (https=) |
| EP (1) | EP1558594A2 (https=) |
| JP (1) | JP2006505575A (https=) |
| KR (1) | KR20050065620A (https=) |
| CN (2) | CN100554257C (https=) |
| AR (1) | AR043055A1 (https=) |
| AU (1) | AU2003296559B2 (https=) |
| BR (1) | BR0315662A (https=) |
| CA (1) | CA2502633C (https=) |
| EC (1) | ECSP055745A (https=) |
| GB (1) | GB0224917D0 (https=) |
| MX (1) | MXPA05004348A (https=) |
| NO (1) | NO20052487L (https=) |
| PE (1) | PE20040779A1 (https=) |
| PL (1) | PL374893A1 (https=) |
| RU (1) | RU2347782C2 (https=) |
| TW (1) | TW200420545A (https=) |
| WO (1) | WO2004037796A2 (https=) |
| ZA (1) | ZA200502700B (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7456184B2 (en) * | 2003-05-01 | 2008-11-25 | Palatin Technologies Inc. | Melanocortin receptor-specific compounds |
| SE0400441D0 (sv) | 2004-02-25 | 2004-02-25 | Active Biotech Ab | Novel Benzofurans and Indols |
| SE0400440D0 (sv) * | 2004-02-25 | 2004-02-25 | Active Biotech Ab | Novel Cinnamic Amides |
| GB0409236D0 (en) * | 2004-04-26 | 2004-05-26 | Novartis Ag | Organic compounds |
| US7777035B2 (en) | 2005-06-22 | 2010-08-17 | Chemocentryx, Inc. | Azaindazole compounds and methods of use |
| CN101007794B (zh) * | 2006-01-26 | 2010-09-01 | 中国科学院上海药物研究所 | N,n'-二取代哌嗪类衍生物及其制备方法、药物组合物和用途 |
| US7601844B2 (en) | 2006-01-27 | 2009-10-13 | Bristol-Myers Squibb Company | Piperidinyl derivatives as modulators of chemokine receptor activity |
| US7615556B2 (en) | 2006-01-27 | 2009-11-10 | Bristol-Myers Squibb Company | Piperazinyl derivatives as modulators of chemokine receptor activity |
| FR2902426B1 (fr) * | 2006-06-19 | 2008-09-05 | Pierre Fabre Medicament Sa | Derives de cinnamoyl-piperazine |
| WO2008090357A2 (en) * | 2007-01-24 | 2008-07-31 | Palatin Technologies, Inc. | N, n; -substituted piperazines binding to melanocortin receptor |
| TWI433838B (zh) | 2008-06-25 | 2014-04-11 | 必治妥美雅史谷比公司 | 作為趨化因子受體活性調節劑之六氫吡啶衍生物 |
| HRP20141190T1 (hr) * | 2010-01-29 | 2015-01-30 | Otsuka Pharmaceutical Co., Ltd. | Disupstituirani derivati piridina kao antikancerogena sredstva |
| US8642622B2 (en) | 2010-06-16 | 2014-02-04 | Bristol-Myers Squibb Company | Piperidinyl compound as a modulator of chemokine receptor activity |
| ES2682217T3 (es) | 2012-08-08 | 2018-09-19 | Mitsubishi Tanabe Pharma Corporation | Método para producir un compuesto de 1,4-benzoxazina |
| US9993497B2 (en) * | 2012-12-30 | 2018-06-12 | Hadasit Medical Research Services And Development Ltd. | Use of alginate compositions in preventing or reducing liver damage caused by a hepatotoxic agent |
| AP2016009020A0 (en) * | 2013-07-18 | 2016-02-29 | Novartis Ag | Autotaxin inhibitors comprising a heteroaromatic ring-benzyl-amide-cycle core |
| WO2015048570A2 (en) * | 2013-09-26 | 2015-04-02 | Sanford-Burnham Medical Research Institute | Ebi2 modulators |
| WO2016116875A1 (en) * | 2015-01-20 | 2016-07-28 | Novartis Ag | Pet imaging agents |
| EP4065112A4 (en) * | 2019-11-22 | 2023-12-27 | The Regents of the University of California | Taspase1 inhibitors and uses thereof |
| US20230062100A1 (en) | 2019-11-28 | 2023-03-02 | Bayer Aktiengesellschaft | Substituted aminoquinolones as dgkalpha inhibitors for immune activation |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60139646A (ja) * | 1983-12-27 | 1985-07-24 | Otsuka Pharmaceut Factory Inc | ナフタレン誘導体 |
| JPS6219577A (ja) * | 1985-07-16 | 1987-01-28 | Kanebo Ltd | 新規なベンジルピペラジン誘導体および該化合物を有効成分とする医薬組成物 |
| SE8803429D0 (sv) * | 1988-09-28 | 1988-09-28 | Pharmacia Ab | Novel pyridyl- and pyrimidyl derivatives |
| SE9201956D0 (sv) * | 1992-06-25 | 1992-06-25 | Kabi Pharmacia Ab | Novel nicotinicacid esters |
| US5380726A (en) * | 1993-01-15 | 1995-01-10 | Ciba-Geigy Corporation | Substituted dialkylthio ethers |
| FR2725445B1 (fr) * | 1994-10-10 | 1996-10-31 | Adir | Nouveaux derives a structure 1-arylalkenyl 4-aryl alkyl piperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| JP2000086603A (ja) * | 1998-07-15 | 2000-03-28 | Yoshitomi Pharmaceut Ind Ltd | 桂皮酸アミド誘導体および３―フェニルプロピオン酸アミド誘導体 |
| US6110922A (en) * | 1998-12-29 | 2000-08-29 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds |
| OA12670A (en) * | 2001-10-22 | 2006-06-20 | Pfizer Prod Inc | Piperazine derivatives with ccr1 receptor antagonist activity. |
-
2002
- 2002-10-25 GB GBGB0224917.5A patent/GB0224917D0/en not_active Ceased
-
2003
- 2003-10-21 TW TW092129162A patent/TW200420545A/zh unknown
- 2003-10-23 AR ARP030103870A patent/AR043055A1/es not_active Application Discontinuation
- 2003-10-23 PE PE2003001076A patent/PE20040779A1/es not_active Application Discontinuation
- 2003-10-24 CN CNB2003801020110A patent/CN100554257C/zh not_active Expired - Fee Related
- 2003-10-24 CN CNA2009101474324A patent/CN101570517A/zh active Pending
- 2003-10-24 RU RU2005115964/04A patent/RU2347782C2/ru not_active IP Right Cessation
- 2003-10-24 EP EP03809328A patent/EP1558594A2/en not_active Withdrawn
- 2003-10-24 MX MXPA05004348A patent/MXPA05004348A/es active IP Right Grant
- 2003-10-24 KR KR1020057006954A patent/KR20050065620A/ko not_active Abandoned
- 2003-10-24 BR BR0315662-1A patent/BR0315662A/pt not_active IP Right Cessation
- 2003-10-24 AU AU2003296559A patent/AU2003296559B2/en not_active Ceased
- 2003-10-24 US US10/532,331 patent/US7645760B2/en not_active Expired - Fee Related
- 2003-10-24 PL PL03374893A patent/PL374893A1/xx not_active Application Discontinuation
- 2003-10-24 JP JP2004545990A patent/JP2006505575A/ja active Pending
- 2003-10-24 CA CA2502633A patent/CA2502633C/en not_active Expired - Fee Related
- 2003-10-24 WO PCT/EP2003/011848 patent/WO2004037796A2/en not_active Ceased
-
2005
- 2005-04-04 ZA ZA200502700A patent/ZA200502700B/en unknown
- 2005-04-25 EC EC2005005745A patent/ECSP055745A/es unknown
- 2005-05-24 NO NO20052487A patent/NO20052487L/no not_active Application Discontinuation
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