JP2011509975A5 - - Google Patents
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- JP2011509975A5 JP2011509975A5 JP2010542630A JP2010542630A JP2011509975A5 JP 2011509975 A5 JP2011509975 A5 JP 2011509975A5 JP 2010542630 A JP2010542630 A JP 2010542630A JP 2010542630 A JP2010542630 A JP 2010542630A JP 2011509975 A5 JP2011509975 A5 JP 2011509975A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- ethyl
- piperidinyl
- amino
- naphthyridin
- 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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- 150000001875 compounds Chemical class 0.000 claims 28
- 125000005843 halogen group Chemical group 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 15
- 150000001204 N-oxides Chemical class 0.000 claims 13
- 239000012453 solvate Substances 0.000 claims 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 11
- -1 chloro, methyl Chemical group 0.000 claims 11
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 241000124008 Mammalia Species 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 241000282412 Homo Species 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 201000008827 tuberculosis Diseases 0.000 claims 3
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
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- 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 1
- 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 1
- 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 1
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- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
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- 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 1
- 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 1
- 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 1
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- PDQFKDYKTUQRCW-UHFFFAOYSA-N 1-[2-[4-[(5,6-dichloropyridin-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(Cl)C(Cl)=C1 PDQFKDYKTUQRCW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
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- 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 1
- 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 1
- 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 1
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- 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 1
- 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 1
- 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 1
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- 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 1
- 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 1
- IKCKOCOUGKFMNK-UHFFFAOYSA-N 1-[2-[4-[(5-bromothiophen-2-yl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound S1C(Br)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 IKCKOCOUGKFMNK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
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- 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 1
- NXNCVAQPAVCKBK-UHFFFAOYSA-N 1-[2-[4-[(5-chloro-6-methylpyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-7-fluoro-1,5-naphthyridin-2-one Chemical compound C1=C(Cl)C(C)=NC=C1CNC1CCN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CC1 NXNCVAQPAVCKBK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- PALKJRUGHAYNHL-UHFFFAOYSA-N 1-[2-[4-[(6-chloropyrazin-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=CN=CC(Cl)=N1 PALKJRUGHAYNHL-UHFFFAOYSA-N 0.000 claims 1
- HAPFZQMUXSNINF-UHFFFAOYSA-N 1-[2-[4-[[4-(trifluoromethyl)phenyl]methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 HAPFZQMUXSNINF-UHFFFAOYSA-N 0.000 claims 1
- MNKXJFVVVTZNTR-UHFFFAOYSA-N 1-[2-[4-[[4-chloro-3-(trifluoromethyl)phenyl]methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(CNC2CCN(CCN3C(C=CC4=NC=CC=C43)=O)CC2)=C1 MNKXJFVVVTZNTR-UHFFFAOYSA-N 0.000 claims 1
- HISCWACCMOALJC-UHFFFAOYSA-N 1-[2-[4-[[4-chloro-3-(trifluoromethyl)phenyl]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(F)(F)F)=C1 HISCWACCMOALJC-UHFFFAOYSA-N 0.000 claims 1
- FXZKWMBMEYSUAR-UHFFFAOYSA-N 1-[2-[4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=NC(C(F)(F)F)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=CC=C32)=O)CC1 FXZKWMBMEYSUAR-UHFFFAOYSA-N 0.000 claims 1
- FSUBRKHXGMFDKW-UHFFFAOYSA-N 2-fluoro-5-[[[1-[2-(7-fluoro-2-oxo-1,5-naphthyridin-1-yl)ethyl]piperidin-4-yl]amino]methyl]benzonitrile Chemical compound C12=CC(F)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(F)C(C#N)=C1 FSUBRKHXGMFDKW-UHFFFAOYSA-N 0.000 claims 1
- PSNFNJBEEBXFLJ-UHFFFAOYSA-N 2-fluoro-5-[[[1-[2-(7-methoxy-2-oxo-1,5-naphthyridin-1-yl)ethyl]piperidin-4-yl]amino]methyl]benzonitrile Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(F)C(C#N)=C1 PSNFNJBEEBXFLJ-UHFFFAOYSA-N 0.000 claims 1
- BZKZMSQQDADCCA-UHFFFAOYSA-N 4-[[[1-[2-(7-methoxy-2-oxo-1,5-naphthyridin-1-yl)ethyl]piperidin-4-yl]amino]methyl]benzonitrile Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(C#N)C=C1 BZKZMSQQDADCCA-UHFFFAOYSA-N 0.000 claims 1
- JHCZNEKEQWZHQX-UHFFFAOYSA-N 7-ethoxy-1-[2-[4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C12=CC(OCC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(C(F)(F)F)N=C1 JHCZNEKEQWZHQX-UHFFFAOYSA-N 0.000 claims 1
- WJBINUIFMLUKEM-PKOBYXMFSA-N 7-fluoro-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=C(F)C=C32)=O)C[C@H]1O)CC1=CC=C(C(F)(F)F)N=C1 WJBINUIFMLUKEM-PKOBYXMFSA-N 0.000 claims 1
- OHFMDPBWONBOLU-PZJWPPBQSA-N 7-fluoro-1-[2-[(3r,4s)-4-[(5-fluoro-6-methylpyridin-3-yl)methylamino]-3-hydroxypiperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=C(F)C(C)=NC=C1CN[C@@H]1[C@H](O)CN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CC1 OHFMDPBWONBOLU-PZJWPPBQSA-N 0.000 claims 1
- 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 1
- 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 1
- VCNILKQVSIXFAO-UHFFFAOYSA-N 7-fluoro-1-[2-[4-[(4-methyl-3-nitrophenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1CNC1CCN(CCN2C(C=CC3=NC=C(F)C=C32)=O)CC1 VCNILKQVSIXFAO-UHFFFAOYSA-N 0.000 claims 1
- HDZUHMZHVNBWTQ-UHFFFAOYSA-N 7-fluoro-1-[2-[4-[(6-fluoro-5-methylpyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound N1=C(F)C(C)=CC(CNC2CCN(CCN3C(C=CC4=NC=C(F)C=C43)=O)CC2)=C1 HDZUHMZHVNBWTQ-UHFFFAOYSA-N 0.000 claims 1
- JRSUIEXWGMZFFT-UHFFFAOYSA-N 7-fluoro-1-[2-[4-[[4-(trifluoromethyl)phenyl]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)C=C1 JRSUIEXWGMZFFT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- LFSLPVAIHCSEMO-UHFFFAOYSA-N 7-methoxy-1-[2-[4-[(4-nitrophenyl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C([N+]([O-])=O)C=C1 LFSLPVAIHCSEMO-UHFFFAOYSA-N 0.000 claims 1
- UDCUYJUOAPONBU-UHFFFAOYSA-N 7-methoxy-1-[2-[4-[(5-methoxy-6-nitropyridin-2-yl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(OC)C([N+]([O-])=O)=N1 UDCUYJUOAPONBU-UHFFFAOYSA-N 0.000 claims 1
- WUMYAHGYGYPGIN-UHFFFAOYSA-N 7-methoxy-1-[2-[4-[(6-methoxypyridin-3-yl)methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(OC)N=C1 WUMYAHGYGYPGIN-UHFFFAOYSA-N 0.000 claims 1
- LUVFDJACUWPMFN-UHFFFAOYSA-N 7-methoxy-1-[2-[4-[[4-(trifluoromethyl)phenyl]methylamino]piperidin-1-yl]ethyl]-1,5-naphthyridin-2-one Chemical compound C12=CC(OC)=CN=C2C=CC(=O)N1CCN(CC1)CCC1NCC1=CC=C(C(F)(F)F)C=C1 LUVFDJACUWPMFN-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08382002A EP2080761A1 (en) | 2008-01-18 | 2008-01-18 | Compounds |
| PCT/EP2009/050436 WO2009090222A1 (en) | 2008-01-18 | 2009-01-15 | Naphthyridin-2(1h) -one compounds useful as antibacterials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011509975A JP2011509975A (ja) | 2011-03-31 |
| JP2011509975A5 true JP2011509975A5 (https=) | 2012-03-01 |
Family
ID=39539553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010542630A Pending JP2011509975A (ja) | 2008-01-18 | 2009-01-15 | 抗菌剤として有用なナフチリジン−２（１ｈ）−オン化合物 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20110319424A1 (https=) |
| EP (2) | EP2080761A1 (https=) |
| JP (1) | JP2011509975A (https=) |
| WO (1) | WO2009090222A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2561631T3 (es) * | 2009-01-15 | 2016-02-29 | Glaxo Group Limited | Compuestos de naftiridin-2(1H)-ona útiles como agentes antibacterianos |
| AR089929A1 (es) * | 2012-02-10 | 2014-10-01 | Actelion Pharmaceuticals Ltd | Proceso para manufacturar un derivado de naftiridina |
| AR090844A1 (es) * | 2012-04-27 | 2014-12-10 | Actelion Pharmaceuticals Ltd | Proceso para elaborar derivados de naftiridina |
| JP6112724B2 (ja) * | 2013-10-31 | 2017-04-12 | 日本化薬株式会社 | １，５−ナフチリジン誘導体およびそれを有効成分として含んでなる殺虫剤 |
| CN110981792B (zh) * | 2019-12-26 | 2022-04-05 | 阿里生物新材料（常州）有限公司 | 一种[(3-溴-6-二氟甲基)吡啶-2-基]甲醇的合成方法 |
| CA3244639A1 (en) | 2021-12-28 | 2025-06-13 | Nippon Shinyaku Co., Ltd. | Indazole compound and pharmaceutical |
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| FR2798656B1 (fr) | 1999-09-17 | 2004-12-17 | Aventis Pharma Sa | Derives de la quinolyl propyl piperidine, leur preparation et les compositions qui les contiennent |
| DE60025048D1 (de) | 2000-07-21 | 2006-01-26 | Ljudmila Petrovna Maljuk | Teller für stehempfänge |
| CZ2003243A3 (cs) | 2000-07-26 | 2003-09-17 | Smithkline Beecham P. L. C. | Aminopiperidinové chinoliny a jejich azaisosterické analogy s antibakteriální aktivitou |
| FR2816618B1 (fr) | 2000-11-15 | 2002-12-27 | Aventis Pharma Sa | Derives heterocyclylalcoyl piperidine, leur preparation et les compositions qui les contiennent |
| GB0031088D0 (en) | 2000-12-20 | 2001-01-31 | Smithkline Beecham Plc | Medicaments |
| EP1345903A1 (en) | 2000-12-21 | 2003-09-24 | Ciba SC Holding AG | Crystalline forms of cerivastatin sodium |
| GB0101577D0 (en) | 2001-01-22 | 2001-03-07 | Smithkline Beecham Plc | Compounds |
| GB0112836D0 (en) | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| GB0112834D0 (en) | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| GB0118238D0 (en) | 2001-07-26 | 2001-09-19 | Smithkline Beecham Plc | Medicaments |
| WO2003064431A2 (en) | 2002-01-29 | 2003-08-07 | Glaxo Group Limited | Aminopiperidine compounds, process for their preparation, and pharmaceutical compositions containing them |
| EP1470125A1 (en) | 2002-01-29 | 2004-10-27 | Glaxo Group Limited | Aminopiperidine derivatives |
| AR040336A1 (es) | 2002-06-26 | 2005-03-30 | Glaxo Group Ltd | Compuesto de piperidina, uso del mismo para la fabricacion de un medicamento, composicion farmaceutica que lo comprende y procedimiento para preparar dicho compuesto |
| TW200406413A (en) | 2002-06-26 | 2004-05-01 | Glaxo Group Ltd | Compounds |
| GB0217294D0 (en) | 2002-07-25 | 2002-09-04 | Glaxo Group Ltd | Medicaments |
| FR2844270B1 (fr) | 2002-09-11 | 2006-05-19 | Aventis Pharma Sa | Derives de la quinolyl propyl piperidine, leur procede et intermediaires de preparation et les compositions qui les contiennent |
| FR2844268B1 (fr) | 2002-09-11 | 2004-10-22 | Aventis Pharma Sa | Derives de la quinolyl propyl piperidine, leurs procedes et intermediaires de preparation et les compositions qui les contiennent |
| WO2004035569A2 (de) | 2002-10-10 | 2004-04-29 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Neue verbindungen mit antibakterieller aktivität |
| ATE479683T1 (de) | 2002-11-05 | 2010-09-15 | Glaxo Group Ltd | Antibakterielle mittel |
| DE60331849D1 (de) | 2002-11-05 | 2010-05-06 | Glaxosmithkline Llc | Antibakterielle wirkstoffe |
| TW200427688A (en) | 2002-12-18 | 2004-12-16 | Glaxo Group Ltd | Antibacterial agents |
| TW200507841A (en) | 2003-03-27 | 2005-03-01 | Glaxo Group Ltd | Antibacterial agents |
| FR2852954B1 (fr) | 2003-03-28 | 2006-07-14 | Aventis Pharma Sa | Derives de quinoleines-4-substituees, leurs procede et intermediaires de preparation et les compositions pharmaceutiques qui les contiennent |
| DE10316081A1 (de) | 2003-04-08 | 2004-10-21 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Neue Verbindungen mit antibakterieller Aktivität |
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| FR2858619B1 (fr) | 2003-08-08 | 2006-12-22 | Aventis Pharma Sa | Derives de quinoleines-4-substituees, leurs procede et intermediaires de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2867472B1 (fr) | 2004-03-12 | 2008-07-18 | Aventis Pharma Sa | Derives de quinoleines-4-substituees, leurs procede et intermediaires de preparation et les compositions pharmaceutiques qui les contiennent |
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| FR2872164B1 (fr) | 2004-06-29 | 2006-11-17 | Aventis Pharma Sa | Derives de quinoleines-4-substituees, leur procede et intermediaires de preparation et les compositions pharmaceutiques qui les contiennent |
| US20070254872A1 (en) | 2004-07-08 | 2007-11-01 | Glaxo Group Limited | Antibacterial Agents |
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| US20070270417A1 (en) | 2004-07-22 | 2007-11-22 | Glaxo Group Limited | Antibacterial Agents |
| US7655648B2 (en) | 2004-08-02 | 2010-02-02 | Glaxo Group Limited | Antibacterial agents |
| US20070161627A1 (en) | 2004-08-09 | 2007-07-12 | Miller William H | Antibacterial agents |
| DE102004041163A1 (de) | 2004-08-25 | 2006-03-02 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Neue Verbindungen mit antibakterieller Aktivität |
| CA2580621A1 (en) | 2004-09-24 | 2006-03-30 | Actelion Pharmaceuticals Ltd | New bicyclic antibiotics |
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| EP1846418A4 (en) | 2005-01-25 | 2009-12-23 | Glaxo Group Ltd | ANTIBACTERIAL ACTIVE SUBSTANCES |
| US7648980B2 (en) | 2005-01-25 | 2010-01-19 | Glaxo Group Limited | Antibacterial agents |
| JP2008528604A (ja) | 2005-01-25 | 2008-07-31 | グラクソ グループ リミテッド | 抗菌剤 |
| JP2008528598A (ja) | 2005-01-25 | 2008-07-31 | グラクソ グループ リミテッド | 抗菌剤 |
| WO2006099884A1 (en) | 2005-03-24 | 2006-09-28 | Actelion Percurex Ag | Beta-aminoalcohol antibiotics |
| NZ562034A (en) | 2005-03-31 | 2009-10-30 | Janssen Pharmaceutica Nv | Bicyclic pyrazole compounds as antibacterial agents |
| WO2007016610A2 (en) | 2005-08-02 | 2007-02-08 | Glaxo Group Limited | Antibacterial agents |
| KR20080064173A (ko) | 2005-10-21 | 2008-07-08 | 글락소 그룹 리미티드 | 항균제로서 유용한 페리 축합 트리시클릭 화합물 |
| ATE465163T1 (de) | 2005-12-22 | 2010-05-15 | Glaxo Group Ltd | Heterocyclische verbindungen, ihre herstellung und ihre verwendung als antibakterielle mittel |
| WO2007115947A1 (en) | 2006-04-06 | 2007-10-18 | Glaxo Group Limited | Pyrrolo-quinoxalinone derivatives as antibacterials |
| EP2007377A4 (en) | 2006-04-06 | 2011-08-17 | Glaxo Group Ltd | ANTIBACTERIAL ACTIVE SUBSTANCES |
| GB0608263D0 (en) | 2006-04-26 | 2006-06-07 | Glaxo Group Ltd | Compounds |
| CN101454319B (zh) * | 2006-05-26 | 2012-06-27 | 富山化学工业株式会社 | 新杂环化合物或其盐及其中间体 |
-
2008
- 2008-01-18 EP EP08382002A patent/EP2080761A1/en not_active Ceased
-
2009
- 2009-01-15 WO PCT/EP2009/050436 patent/WO2009090222A1/en not_active Ceased
- 2009-01-15 JP JP2010542630A patent/JP2011509975A/ja active Pending
- 2009-01-15 EP EP09701984A patent/EP2238135A1/en not_active Withdrawn
- 2009-01-15 US US12/863,254 patent/US20110319424A1/en not_active Abandoned
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