JP2011509975A - 抗菌剤として有用なナフチリジン−２（１ｈ）−オン化合物 - Google Patents

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Publication number

JP2011509975A

JP2011509975A JP2010542630A JP2010542630A JP2011509975A JP 2011509975 A JP2011509975 A JP 2011509975A JP 2010542630 A JP2010542630 A JP 2010542630A JP 2010542630 A JP2010542630 A JP 2010542630A JP 2011509975 A JP2011509975 A JP 2011509975A

Authority

JP

Japan

Prior art keywords

methyl

ethyl

piperidinyl

amino

naphthyridin

Prior art date

2008-01-18

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 271
• 239000003242 anti bacterial agent Substances 0.000 title abstract description 4
• 238000000034 method Methods 0.000 claims abstract description 53
• 239000003814 drug Substances 0.000 claims abstract description 24
• 201000008827 tuberculosis Diseases 0.000 claims abstract description 23
• 238000002360 preparation method Methods 0.000 claims abstract description 17
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
• 125000001424 substituent group Chemical group 0.000 claims abstract description 9
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 9
• 125000002541 furyl group Chemical group 0.000 claims abstract description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 7
• 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 7
• 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 5
• 125000005843 halogen group Chemical group 0.000 claims description 69
• -1 chloro, methyl Chemical group 0.000 claims description 66
• 150000003839 salts Chemical class 0.000 claims description 59
• 239000012453 solvate Substances 0.000 claims description 45
• 150000001204 N-oxides Chemical class 0.000 claims description 43
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
• 238000006243 chemical reaction Methods 0.000 claims description 37
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• 125000000217 alkyl group Chemical group 0.000 claims description 30
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 24
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
• 241000124008 Mammalia Species 0.000 claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 241000282412 Homo Species 0.000 claims description 14
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 208000035143 Bacterial infection Diseases 0.000 claims description 11
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 11
• 125000001246 bromo group Chemical group Br* 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 239000003085 diluting agent Substances 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 239000002253 acid Substances 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
• MYLSHHVBOXKZKT-UHFFFAOYSA-N 1-[2-[4-[(3,4-dichlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)C(Cl)=C1 MYLSHHVBOXKZKT-UHFFFAOYSA-N 0.000 claims description 5
• VWBWLHOSYHGAJS-UHFFFAOYSA-N 1-[2-[4-[(2-bromo-1,3-thiazol-5-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CN=C(Br)S1 VWBWLHOSYHGAJS-UHFFFAOYSA-N 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• DXQCAMNNBNGXOQ-UHFFFAOYSA-N 1-[2-[4-[(2-bromo-1,3-thiazol-5-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one;hydrochloride Chemical compound Cl.C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CN=C(Br)S1 DXQCAMNNBNGXOQ-UHFFFAOYSA-N 0.000 claims description 3
• SEWRZKOQQTYNEI-UHFFFAOYSA-N 1-[2-[4-[(3,4-dichlorophenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 SEWRZKOQQTYNEI-UHFFFAOYSA-N 0.000 claims description 3
• WUNCDVDTPWRKQE-UHFFFAOYSA-N 1-[2-[4-[(3,4-dichlorophenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one;dihydrochloride Chemical compound Cl.Cl.C1=C(Cl)C(Cl)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 WUNCDVDTPWRKQE-UHFFFAOYSA-N 0.000 claims description 3
• KVGSIEKQTSJHLC-UHFFFAOYSA-N 1-[2-[4-[(3,4-dichlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)C(Cl)=C1 KVGSIEKQTSJHLC-UHFFFAOYSA-N 0.000 claims description 3
• SPQBWAXCFFOJBR-UHFFFAOYSA-N 1-[2-[4-[(3,4-dichlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)C(Cl)=C1 SPQBWAXCFFOJBR-UHFFFAOYSA-N 0.000 claims description 3
• VJRBUGCACVKLKH-UHFFFAOYSA-N 1-[2-[4-[(3,4-dichlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one;hydrochloride Chemical compound Cl.C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)C(Cl)=C1 VJRBUGCACVKLKH-UHFFFAOYSA-N 0.000 claims description 3
• HWQSSHHGBPKHJR-UHFFFAOYSA-N 1-[2-[4-[(4,5-dichloro-1,3-thiazol-2-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=NC(Cl)=C(Cl)S1 HWQSSHHGBPKHJR-UHFFFAOYSA-N 0.000 claims description 3
• PTOBVJLDXIDTTM-UHFFFAOYSA-N 1-[2-[4-[(4,5-dimethyl-1,3-thiazol-2-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=NC(C)=C(C)S1 PTOBVJLDXIDTTM-UHFFFAOYSA-N 0.000 claims description 3
• OSDCFFCRUQDCJP-UHFFFAOYSA-N 1-[2-[4-[(4-chlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)C=C1 OSDCFFCRUQDCJP-UHFFFAOYSA-N 0.000 claims description 3
• XLRYHZYRSXOROI-UHFFFAOYSA-N 1-[2-[4-[(4-chlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)C=C1 XLRYHZYRSXOROI-UHFFFAOYSA-N 0.000 claims description 3
• CVJYEOQLTBKVDN-UHFFFAOYSA-N 1-[2-[4-[(4-chlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one;hydrochloride Chemical compound Cl.C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)C=C1 CVJYEOQLTBKVDN-UHFFFAOYSA-N 0.000 claims description 3
• WSFMXVGZKXACKG-UHFFFAOYSA-N 1-[2-[4-[(4-fluoro-3-methylphenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(F)C(C)=C1 WSFMXVGZKXACKG-UHFFFAOYSA-N 0.000 claims description 3
• MIQIBRQZDFLVDY-UHFFFAOYSA-N 1-[2-[4-[(5-bromo-1,2-thiazol-3-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC=1C=C(Br)SN=1 MIQIBRQZDFLVDY-UHFFFAOYSA-N 0.000 claims description 3
• KBCFGPSNULTRPQ-UHFFFAOYSA-N 1-[2-[4-[(5-bromopyridin-2-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Br)C=N1 KBCFGPSNULTRPQ-UHFFFAOYSA-N 0.000 claims description 3
• IRABNOKGHAAKRH-UHFFFAOYSA-N 1-[2-[4-[(6-bromopyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=NC(Br)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 IRABNOKGHAAKRH-UHFFFAOYSA-N 0.000 claims description 3
• DAWQZUXLLAMDHR-UHFFFAOYSA-N 1-[2-[4-[(6-bromopyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Br)N=C1 DAWQZUXLLAMDHR-UHFFFAOYSA-N 0.000 claims description 3
• ZXRGGVAVXCVFPP-UHFFFAOYSA-N 7-fluoro-1-[2-[4-[(2-methyl-1h-imidazol-5-yl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C(C)=NC(CNC2CCN(CCN3C(C=CC4=NC=C(F)C=C43)=O)CC2)=C1 ZXRGGVAVXCVFPP-UHFFFAOYSA-N 0.000 claims description 3
• HOTJVUDSBOYLBB-UHFFFAOYSA-N 7-fluoro-1-[2-[4-[(4-fluorophenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=CC(F)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CC1 HOTJVUDSBOYLBB-UHFFFAOYSA-N 0.000 claims description 3
• CKBAKJRKBMLFGZ-UHFFFAOYSA-N 7-fluoro-1-[2-[4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(C(F)(F)F)N=C1 CKBAKJRKBMLFGZ-UHFFFAOYSA-N 0.000 claims description 3
• KZNPZGBBKUCCIA-UHFFFAOYSA-N 7-fluoro-1-[2-[4-methyl-4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1CN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CCC1(C)NCC1=CC=C(C(F)(F)F)N=C1 KZNPZGBBKUCCIA-UHFFFAOYSA-N 0.000 claims description 3
• XKBWXAPOLSODDI-PKOBYXMFSA-N 1-[2-[(3r,4s)-3-hydroxy-4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound N([C@H]1CCN(CCN2C(C=CC3=NC=CC=C32)=O)C[C@H]1O)CC1=CC=C(C(F)(F)F)N=C1 XKBWXAPOLSODDI-PKOBYXMFSA-N 0.000 claims description 2
• IZOGCUKAMJBKHV-AZUAARDMSA-N 1-[2-[(3r,4s)-3-hydroxy-4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound N([C@H]1CCN(C[C@H]1O)CCN1C(=O)C=CC2=NC=C(C=C21)OC)CC1=CC=C(C(F)(F)F)N=C1 IZOGCUKAMJBKHV-AZUAARDMSA-N 0.000 claims description 2
• MCIFHJGRNHEVNT-PZJWPPBQSA-N 1-[2-[(3r,4s)-4-[(3,4-dichlorophenyl)methylamino]-3-hydroxypiperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound N([C@H]1CCN(CCN2C(C=CC3=NC=CC=C32)=O)C[C@H]1O)CC1=CC=C(Cl)C(Cl)=C1 MCIFHJGRNHEVNT-PZJWPPBQSA-N 0.000 claims description 2
• YAKNAQDRBCBEAB-PZJWPPBQSA-N 1-[2-[(3r,4s)-4-[(3,4-dichlorophenyl)methylamino]-3-hydroxypiperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound N([C@H]1CCN(CCN2C(C=CC3=NC=C(F)C=C32)=O)C[C@H]1O)CC1=CC=C(Cl)C(Cl)=C1 YAKNAQDRBCBEAB-PZJWPPBQSA-N 0.000 claims description 2
• JGEBXOKKDVVTCH-RBBKRZOGSA-N 1-[2-[(3r,4s)-4-[(3,4-dichlorophenyl)methylamino]-3-hydroxypiperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound N([C@H]1CCN(C[C@H]1O)CCN1C(=O)C=CC2=NC=C(C=C21)OC)CC1=CC=C(Cl)C(Cl)=C1 JGEBXOKKDVVTCH-RBBKRZOGSA-N 0.000 claims description 2
• JTJQZNDYWHLRMU-PZJWPPBQSA-N 1-[2-[(3r,4s)-4-[(5-bromo-6-methylpyridin-3-yl)methylamino]-3-hydroxypiperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C1=C(Br)C(C)=NC=C1CN[C@@H]1[C@H](O)CN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CC1 JTJQZNDYWHLRMU-PZJWPPBQSA-N 0.000 claims description 2
• FGSFMTUSMVYQOZ-LZAGWAHOSA-N 1-[2-[(3r,4s)-4-[(5-chloro-6-methylpyridin-3-yl)methylamino]-3-hydroxypiperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one;hydrochloride Chemical compound Cl.C1=C(Cl)C(C)=NC=C1CN[C@@H]1[C@H](O)CN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CC1 FGSFMTUSMVYQOZ-LZAGWAHOSA-N 0.000 claims description 2
• CNCLIOUSVRIYNI-RBBKRZOGSA-N 1-[2-[(3r,4s)-4-[(5-chloro-6-methylpyridin-3-yl)methylamino]-3-hydroxypiperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound N([C@H]1CCN(C[C@H]1O)CCN1C(=O)C=CC2=NC=C(C=C21)OC)CC1=CN=C(C)C(Cl)=C1 CNCLIOUSVRIYNI-RBBKRZOGSA-N 0.000 claims description 2
• IZOGCUKAMJBKHV-QUCCMNQESA-N 1-[2-[(3s,4r)-3-hydroxy-4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound N([C@@H]1CCN(C[C@@H]1O)CCN1C(=O)C=CC2=NC=C(C=C21)OC)CC1=CC=C(C(F)(F)F)N=C1 IZOGCUKAMJBKHV-QUCCMNQESA-N 0.000 claims description 2
• JGEBXOKKDVVTCH-IRLDBZIGSA-N 1-[2-[(3s,4r)-4-[(3,4-dichlorophenyl)methylamino]-3-hydroxypiperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound N([C@@H]1CCN(C[C@@H]1O)CCN1C(=O)C=CC2=NC=C(C=C21)OC)CC1=CC=C(Cl)C(Cl)=C1 JGEBXOKKDVVTCH-IRLDBZIGSA-N 0.000 claims description 2
• KBHAEKIRTIPWLC-UHFFFAOYSA-N 1-[2-[4-[(2,4-dichlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)C=C1Cl KBHAEKIRTIPWLC-UHFFFAOYSA-N 0.000 claims description 2
• BOENDXXFMMUORV-UHFFFAOYSA-N 1-[2-[4-[(2,5-dichlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC(Cl)=CC=C1Cl BOENDXXFMMUORV-UHFFFAOYSA-N 0.000 claims description 2
• VSGHQQIETBKBSQ-UHFFFAOYSA-N 1-[2-[4-[(2-bromo-1,3-thiazol-5-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CN=C(Br)S1 VSGHQQIETBKBSQ-UHFFFAOYSA-N 0.000 claims description 2
• JSOIDOONLXIBLQ-UHFFFAOYSA-N 1-[2-[4-[(2-chloro-1,3-thiazol-5-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CN=C(Cl)S1 JSOIDOONLXIBLQ-UHFFFAOYSA-N 0.000 claims description 2
• HQOHRBYXGPDCCO-UHFFFAOYSA-N 1-[2-[4-[(3,4-dibromophenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=C(Br)C(Br)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 HQOHRBYXGPDCCO-UHFFFAOYSA-N 0.000 claims description 2
• ZTVSDXFHBSSIBD-UHFFFAOYSA-N 1-[2-[4-[(3,4-dibromophenyl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Br)C(Br)=C1 ZTVSDXFHBSSIBD-UHFFFAOYSA-N 0.000 claims description 2
• CSTBXBUAABIDNV-UHFFFAOYSA-N 1-[2-[4-[(3,4-dibromophenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Br)C(Br)=C1 CSTBXBUAABIDNV-UHFFFAOYSA-N 0.000 claims description 2
• PZPXSUVXJLBOGM-UHFFFAOYSA-N 1-[2-[4-[(3,4-dichlorophenyl)methylamino]-4-methylpiperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C1CN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CCC1(C)NCC1=CC=C(Cl)C(Cl)=C1 PZPXSUVXJLBOGM-UHFFFAOYSA-N 0.000 claims description 2
• KBLPBVDNBORBGS-UHFFFAOYSA-N 1-[2-[4-[(3,4-dichlorophenyl)methylamino]-4-methylpiperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1(C)NCC1=CC=C(Cl)C(Cl)=C1 KBLPBVDNBORBGS-UHFFFAOYSA-N 0.000 claims description 2
• RLPWPYWBFXXPHU-UHFFFAOYSA-N 1-[2-[4-[(3,4-difluorophenyl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(F)C(F)=C1 RLPWPYWBFXXPHU-UHFFFAOYSA-N 0.000 claims description 2
• UPHCUQHBTRUESI-UHFFFAOYSA-N 1-[2-[4-[(3,4-difluorophenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(F)C(F)=C1 UPHCUQHBTRUESI-UHFFFAOYSA-N 0.000 claims description 2
• JJDSFSBPIIKLKB-UHFFFAOYSA-N 1-[2-[4-[(3,4-dimethylphenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=C(C)C(C)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 JJDSFSBPIIKLKB-UHFFFAOYSA-N 0.000 claims description 2
• LKIFBPPGDNTNAJ-UHFFFAOYSA-N 1-[2-[4-[(3,4-dimethylphenyl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C1=C(C)C(C)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CC1 LKIFBPPGDNTNAJ-UHFFFAOYSA-N 0.000 claims description 2
• MMXOJPDJBNDJNG-UHFFFAOYSA-N 1-[2-[4-[(3,4-dimethylphenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(C)C(C)=C1 MMXOJPDJBNDJNG-UHFFFAOYSA-N 0.000 claims description 2
• ZJXBMFMRVAMFSK-UHFFFAOYSA-N 1-[2-[4-[(3,5-dichlorophenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound ClC1=CC(Cl)=CC(CNC2CCN(CCN3C(C=CC4=NC=CC=C43)=O)CC2)=C1 ZJXBMFMRVAMFSK-UHFFFAOYSA-N 0.000 claims description 2
• RPTKHHSOOHODTJ-UHFFFAOYSA-N 1-[2-[4-[(3,5-dichlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC(Cl)=CC(Cl)=C1 RPTKHHSOOHODTJ-UHFFFAOYSA-N 0.000 claims description 2
• YEUJSVGJJYFGOR-UHFFFAOYSA-N 1-[2-[4-[(3,5-dichlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC(Cl)=CC(Cl)=C1 YEUJSVGJJYFGOR-UHFFFAOYSA-N 0.000 claims description 2
• DKRZYTRWBFGYIC-UHFFFAOYSA-N 1-[2-[4-[(3,5-dimethylphenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC(C)=CC(C)=C1 DKRZYTRWBFGYIC-UHFFFAOYSA-N 0.000 claims description 2
• HYQVJBXXNIBTKB-UHFFFAOYSA-N 1-[2-[4-[(3-chloro-4-methoxyphenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 HYQVJBXXNIBTKB-UHFFFAOYSA-N 0.000 claims description 2
• SUKJUMUVJWYBFF-UHFFFAOYSA-N 1-[2-[4-[(3-chloro-4-methylphenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=C(Cl)C(C)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 SUKJUMUVJWYBFF-UHFFFAOYSA-N 0.000 claims description 2
• PDASBUJZBAILIN-UHFFFAOYSA-N 1-[2-[4-[(3-chloro-4-methylphenyl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C1=C(Cl)C(C)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CC1 PDASBUJZBAILIN-UHFFFAOYSA-N 0.000 claims description 2
• YHDZSOCSAIOGJM-UHFFFAOYSA-N 1-[2-[4-[(3-chloro-4-methylphenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(C)C(Cl)=C1 YHDZSOCSAIOGJM-UHFFFAOYSA-N 0.000 claims description 2
• GAQQBZSXAKTXIR-UHFFFAOYSA-N 1-[2-[4-[(3-chlorophenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound ClC1=CC=CC(CNC2CCN(CCN3C(C=CC4=NC=CC=C43)=O)CC2)=C1 GAQQBZSXAKTXIR-UHFFFAOYSA-N 0.000 claims description 2
• ONTZXJXFUWWLDK-UHFFFAOYSA-N 1-[2-[4-[(3-chlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=CC(Cl)=C1 ONTZXJXFUWWLDK-UHFFFAOYSA-N 0.000 claims description 2
• OVVZXKLXEBNDDD-UHFFFAOYSA-N 1-[2-[4-[(3-chlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=CC(Cl)=C1 OVVZXKLXEBNDDD-UHFFFAOYSA-N 0.000 claims description 2
• MNDCBQLPWCTNKI-UHFFFAOYSA-N 1-[2-[4-[(3-fluoro-4-methylphenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=C(F)C(C)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 MNDCBQLPWCTNKI-UHFFFAOYSA-N 0.000 claims description 2
• CRCPCAMRFUWYQD-UHFFFAOYSA-N 1-[2-[4-[(3-fluoro-4-methylphenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(C)C(F)=C1 CRCPCAMRFUWYQD-UHFFFAOYSA-N 0.000 claims description 2
• PZKDFGQVJQUCGQ-UHFFFAOYSA-N 1-[2-[4-[(3-fluoro-5-methylphenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC(C)=CC(F)=C1 PZKDFGQVJQUCGQ-UHFFFAOYSA-N 0.000 claims description 2
• VCUKLFPDLUPKJR-UHFFFAOYSA-N 1-[2-[4-[(4,5-dibromothiophen-2-yl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound S1C(Br)=C(Br)C=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 VCUKLFPDLUPKJR-UHFFFAOYSA-N 0.000 claims description 2
• BCMFQVOFQIYTPI-UHFFFAOYSA-N 1-[2-[4-[(4,5-dibromothiophen-2-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC(Br)=C(Br)S1 BCMFQVOFQIYTPI-UHFFFAOYSA-N 0.000 claims description 2
• DDGLSDSYVUGMKT-UHFFFAOYSA-N 1-[2-[4-[(4,5-dibromothiophen-2-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC(Br)=C(Br)S1 DDGLSDSYVUGMKT-UHFFFAOYSA-N 0.000 claims description 2
• DJRPLKBGCXDIKR-UHFFFAOYSA-N 1-[2-[4-[(4,6-dimethylpyridin-2-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC(C)=CC(C)=N1 DJRPLKBGCXDIKR-UHFFFAOYSA-N 0.000 claims description 2
• LWHZWNIYABVXKW-UHFFFAOYSA-N 1-[2-[4-[(4-bromo-1,3-thiazol-2-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=NC(Br)=CS1 LWHZWNIYABVXKW-UHFFFAOYSA-N 0.000 claims description 2
• LXOUTJFEDZQFMR-UHFFFAOYSA-N 1-[2-[4-[(4-bromo-1,3-thiazol-2-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=NC(Br)=CS1 LXOUTJFEDZQFMR-UHFFFAOYSA-N 0.000 claims description 2
• VAVOOEQEKVFPPG-UHFFFAOYSA-N 1-[2-[4-[(4-bromo-3-methylphenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Br)C(C)=C1 VAVOOEQEKVFPPG-UHFFFAOYSA-N 0.000 claims description 2
• VLJBWYPTGOHMQA-UHFFFAOYSA-N 1-[2-[4-[(4-bromopyridin-2-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC(Br)=CC=N1 VLJBWYPTGOHMQA-UHFFFAOYSA-N 0.000 claims description 2
• GQQRKJSWOMKJDJ-UHFFFAOYSA-N 1-[2-[4-[(4-bromothiophen-2-yl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound BrC1=CSC(CNC2CCN(CCN3C(C=CC4=NC=CC=C43)=O)CC2)=C1 GQQRKJSWOMKJDJ-UHFFFAOYSA-N 0.000 claims description 2
• CTLLWCXQVJIFNT-UHFFFAOYSA-N 1-[2-[4-[(4-bromothiophen-2-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC(Br)=CS1 CTLLWCXQVJIFNT-UHFFFAOYSA-N 0.000 claims description 2
• SMILIJMQTOQWLA-UHFFFAOYSA-N 1-[2-[4-[(4-chloro-3-methylphenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=C(Cl)C(C)=CC(CNC2CCN(CCN3C(C=CC4=NC=CC=C43)=O)CC2)=C1 SMILIJMQTOQWLA-UHFFFAOYSA-N 0.000 claims description 2
• ZKHRGUKLTPQWIJ-UHFFFAOYSA-N 1-[2-[4-[(4-chloro-3-methylphenyl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C1=C(Cl)C(C)=CC(CNC2CCN(CCN3C(C=CC4=NC=C(F)C=C43)=O)CC2)=C1 ZKHRGUKLTPQWIJ-UHFFFAOYSA-N 0.000 claims description 2
• BEZKBGBINVKHGN-UHFFFAOYSA-N 1-[2-[4-[(4-chloro-3-methylphenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)C(C)=C1 BEZKBGBINVKHGN-UHFFFAOYSA-N 0.000 claims description 2
• KIRYBLLGOJPCKC-UHFFFAOYSA-N 1-[2-[4-[(4-chloro-5-fluoropyridin-2-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC(Cl)=C(F)C=N1 KIRYBLLGOJPCKC-UHFFFAOYSA-N 0.000 claims description 2
• PSPHYLYWPUZGNO-UHFFFAOYSA-N 1-[2-[4-[(4-chlorophenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=CC(Cl)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 PSPHYLYWPUZGNO-UHFFFAOYSA-N 0.000 claims description 2
• OCIJMSSFMWSVMQ-UHFFFAOYSA-N 1-[2-[4-[(4-chlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-ethoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OCC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)C=C1 OCIJMSSFMWSVMQ-UHFFFAOYSA-N 0.000 claims description 2
• AVMFIXNEPOTXLQ-UHFFFAOYSA-N 1-[2-[4-[(4-chlorophenyl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)C=C1 AVMFIXNEPOTXLQ-UHFFFAOYSA-N 0.000 claims description 2
• BGBLSVCOEJHCBY-UHFFFAOYSA-N 1-[2-[4-[(4-fluorophenyl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(F)C=C1 BGBLSVCOEJHCBY-UHFFFAOYSA-N 0.000 claims description 2
• WPRLOPBZYNRDPO-UHFFFAOYSA-N 1-[2-[4-[(4-tert-butylphenyl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C1=CC(C(C)(C)C)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CC1 WPRLOPBZYNRDPO-UHFFFAOYSA-N 0.000 claims description 2
• PQMINJGXKODELG-UHFFFAOYSA-N 1-[2-[4-[(5,6-dichloropyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CN=C(Cl)C(Cl)=C1 PQMINJGXKODELG-UHFFFAOYSA-N 0.000 claims description 2
• GIVNQECXNIRYHQ-UHFFFAOYSA-N 1-[2-[4-[(5,6-dimethylpyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound N1=C(C)C(C)=CC(CNC2CCN(CCN3C(C=CC4=NC=C(F)C=C43)=O)CC2)=C1 GIVNQECXNIRYHQ-UHFFFAOYSA-N 0.000 claims description 2
• HJJXDHRRQJEOMV-UHFFFAOYSA-N 1-[2-[4-[(5-bromo-4-methyl-1,3-thiazol-2-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound S1C(Br)=C(C)N=C1CNC1CCN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CC1 HJJXDHRRQJEOMV-UHFFFAOYSA-N 0.000 claims description 2
• GJNNMOIRNDBNLN-UHFFFAOYSA-N 1-[2-[4-[(5-bromo-4-methylthiophen-2-yl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound S1C(Br)=C(C)C=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 GJNNMOIRNDBNLN-UHFFFAOYSA-N 0.000 claims description 2
• NUZZRRJJRMWMCL-UHFFFAOYSA-N 1-[2-[4-[(5-bromo-4-methylthiophen-2-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound S1C(Br)=C(C)C=C1CNC1CCN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CC1 NUZZRRJJRMWMCL-UHFFFAOYSA-N 0.000 claims description 2
• IHTQDKDFPRTTOH-UHFFFAOYSA-N 1-[2-[4-[(5-bromo-6-methylpyridin-2-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C1=C(Br)C(C)=NC(CNC2CCN(CCN3C(C=CC4=NC=C(F)C=C43)=O)CC2)=C1 IHTQDKDFPRTTOH-UHFFFAOYSA-N 0.000 claims description 2
• LAFAFVWGCAGRCI-UHFFFAOYSA-N 1-[2-[4-[(5-bromo-6-methylpyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C1=C(Br)C(C)=NC=C1CNC1CCN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CC1 LAFAFVWGCAGRCI-UHFFFAOYSA-N 0.000 claims description 2
• KBKJMQJLEQBIJH-UHFFFAOYSA-N 1-[2-[4-[(5-bromofuran-2-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Br)O1 KBKJMQJLEQBIJH-UHFFFAOYSA-N 0.000 claims description 2
• DFUOHVMREREJCR-UHFFFAOYSA-N 1-[2-[4-[(5-bromofuran-2-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Br)O1 DFUOHVMREREJCR-UHFFFAOYSA-N 0.000 claims description 2
• JLVSZCVXQFRRKZ-UHFFFAOYSA-N 1-[2-[4-[(5-bromopyridin-2-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Br)C=N1 JLVSZCVXQFRRKZ-UHFFFAOYSA-N 0.000 claims description 2
• YYQCMWLIBDTHQK-UHFFFAOYSA-N 1-[2-[4-[(5-bromopyridin-2-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Br)C=N1 YYQCMWLIBDTHQK-UHFFFAOYSA-N 0.000 claims description 2
• UKEMOQMIXKFTSV-UHFFFAOYSA-N 1-[2-[4-[(5-bromopyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CN=CC(Br)=C1 UKEMOQMIXKFTSV-UHFFFAOYSA-N 0.000 claims description 2
• PWCHJCRAARFJCK-UHFFFAOYSA-N 1-[2-[4-[(5-bromopyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CN=CC(Br)=C1 PWCHJCRAARFJCK-UHFFFAOYSA-N 0.000 claims description 2
• AYCDPBAPKCAFGO-UHFFFAOYSA-N 1-[2-[4-[(5-bromothiophen-2-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Br)S1 AYCDPBAPKCAFGO-UHFFFAOYSA-N 0.000 claims description 2
• VOYHBCSAGUPVAO-UHFFFAOYSA-N 1-[2-[4-[(5-bromothiophen-2-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Br)S1 VOYHBCSAGUPVAO-UHFFFAOYSA-N 0.000 claims description 2
• LVFOJVFPXANOLK-UHFFFAOYSA-N 1-[2-[4-[(5-chloro-6-ethylpyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C1=C(Cl)C(CC)=NC=C1CNC1CCN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CC1 LVFOJVFPXANOLK-UHFFFAOYSA-N 0.000 claims description 2
• AKROKOSZPUFRSK-UHFFFAOYSA-N 1-[2-[4-[(5-chloro-6-methoxypyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CN=C(OC)C(Cl)=C1 AKROKOSZPUFRSK-UHFFFAOYSA-N 0.000 claims description 2
• ISDOUMQPUIPUCC-UHFFFAOYSA-N 1-[2-[4-[(5-chloro-6-methylpyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=C(Cl)C(C)=NC=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 ISDOUMQPUIPUCC-UHFFFAOYSA-N 0.000 claims description 2
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• UUJJMROKXMZZRA-UHFFFAOYSA-N 1-[2-[4-[(5-chloropyridin-2-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)C=N1 UUJJMROKXMZZRA-UHFFFAOYSA-N 0.000 claims description 2
• GJHGBVNNOVZZQK-UHFFFAOYSA-N 1-[2-[4-[(5-chloropyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CN=CC(Cl)=C1 GJHGBVNNOVZZQK-UHFFFAOYSA-N 0.000 claims description 2
• CSKZKZDFRFOJOX-UHFFFAOYSA-N 1-[2-[4-[(5-chlorothiophen-2-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)S1 CSKZKZDFRFOJOX-UHFFFAOYSA-N 0.000 claims description 2
• VZSKMIYNGGPZBT-UHFFFAOYSA-N 1-[2-[4-[(5-chlorothiophen-2-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Cl)S1 VZSKMIYNGGPZBT-UHFFFAOYSA-N 0.000 claims description 2
• DUUGZGISQIIHEF-UHFFFAOYSA-N 1-[2-[4-[(5-fluoro-6-methoxypyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CN=C(OC)C(F)=C1 DUUGZGISQIIHEF-UHFFFAOYSA-N 0.000 claims description 2
• WXXDINLCTOXSGZ-UHFFFAOYSA-N 1-[2-[4-[(6-bromopyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-7-methoxy-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(Br)N=C1 WXXDINLCTOXSGZ-UHFFFAOYSA-N 0.000 claims description 2
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