JP2005519981A5 - - Google Patents
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- Publication number
- JP2005519981A5 JP2005519981A5 JP2003584054A JP2003584054A JP2005519981A5 JP 2005519981 A5 JP2005519981 A5 JP 2005519981A5 JP 2003584054 A JP2003584054 A JP 2003584054A JP 2003584054 A JP2003584054 A JP 2003584054A JP 2005519981 A5 JP2005519981 A5 JP 2005519981A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- alkyl
- amide
- ylmethyl
- methoxy
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 109
- -1 amino, piperidyl Chemical group 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 24
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 24
- 125000003277 amino group Chemical group 0.000 claims description 23
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 22
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 13
- 229910005965 SO 2 Inorganic materials 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
- LASPDBMDWYKLQC-IYARVYRRSA-N COC1=CC2=C(C=C1)N=CC=C2NC(=O)[C@H]1CC[C@@H](CC1)NCC1=CC=C2SCC(=O)NC2=C1 Chemical compound COC1=CC2=C(C=C1)N=CC=C2NC(=O)[C@H]1CC[C@@H](CC1)NCC1=CC=C2SCC(=O)NC2=C1 LASPDBMDWYKLQC-IYARVYRRSA-N 0.000 claims description 2
- VQDYYIZWEXWVDX-QAQDUYKDSA-N COC1=CC2=C(N=CC=C2NC(=O)[C@H]2CC[C@@H](CC2)NCC2=CC=C3SCC(=O)NC3=C2)C(F)=C1 Chemical compound COC1=CC2=C(N=CC=C2NC(=O)[C@H]2CC[C@@H](CC2)NCC2=CC=C3SCC(=O)NC3=C2)C(F)=C1 VQDYYIZWEXWVDX-QAQDUYKDSA-N 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- VUHCPMIDSUGHNO-UHFFFAOYSA-N 6-methoxy-1,5-naphthyridin-4-amine Chemical compound N1=CC=C(N)C2=NC(OC)=CC=C21 VUHCPMIDSUGHNO-UHFFFAOYSA-N 0.000 claims 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 19
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 16
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 16
- 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 8
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 8
- 150000001408 amides Chemical class 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000006413 ring segment Chemical group 0.000 claims 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- OIBGVZXCQRBLSA-ZXYWRSMDSA-N (1r,3r,4r)-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)-4-[(2-oxo-1h-pyrido[3,4-b][1,4]thiazin-7-yl)methylamino]cyclohexane-1-carboxamide Chemical compound N1C(=O)CSC(C=N2)=C1C=C2CN[C@@H]([C@H](O)C1)CC[C@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 OIBGVZXCQRBLSA-ZXYWRSMDSA-N 0.000 claims 2
- KLDOCEWRXGXRDS-DDUZABMNSA-N (1r,3r,4r)-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)-4-[(3-oxo-4h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]cyclohexane-1-carboxamide Chemical compound S1CC(=O)NC2=NC(CN[C@@H]3CC[C@H](C[C@H]3O)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 KLDOCEWRXGXRDS-DDUZABMNSA-N 0.000 claims 2
- KLDOCEWRXGXRDS-YEWWUXTCSA-N (1s,3s,4s)-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)-4-[(3-oxo-4h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]cyclohexane-1-carboxamide Chemical compound S1CC(=O)NC2=NC(CN[C@H]3CC[C@@H](C[C@@H]3O)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 KLDOCEWRXGXRDS-YEWWUXTCSA-N 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000005035 acylthio group Chemical group 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- BOPUCGGDXLOLLU-ZXYWRSMDSA-N (1r,3r,4r)-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)-4-[(2-oxo-1h-pyrido[3,4-b][1,4]oxazin-7-yl)methylamino]cyclohexane-1-carboxamide Chemical compound N1C(=O)COC(C=N2)=C1C=C2CN[C@@H]([C@H](O)C1)CC[C@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 BOPUCGGDXLOLLU-ZXYWRSMDSA-N 0.000 claims 1
- UQPMSQLUONKZOF-DDUZABMNSA-N (1r,3r,4r)-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)-4-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]cyclohexane-1-carboxamide Chemical compound O1CC(=O)NC2=NC(CN[C@@H]3CC[C@H](C[C@H]3O)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 UQPMSQLUONKZOF-DDUZABMNSA-N 0.000 claims 1
- DQAOVLVVHPRDAI-RVZJWNSFSA-N (1r,3r,4r)-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)-4-[(6-oxo-5h-pyridazino[3,4-b][1,4]thiazin-3-yl)methylamino]cyclohexane-1-carboxamide Chemical compound N1C(=O)CSC(N=N2)=C1C=C2CN[C@@H]([C@H](O)C1)CC[C@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 DQAOVLVVHPRDAI-RVZJWNSFSA-N 0.000 claims 1
- TVHALYRBKNFFTC-JXXFODFXSA-N (1r,3r,4r)-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)-4-[(7-methyl-3,4-dihydro-2h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]cyclohexane-1-carboxamide Chemical compound N1CCSC(C=C2C)=C1N=C2CN[C@@H]([C@H](O)C1)CC[C@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 TVHALYRBKNFFTC-JXXFODFXSA-N 0.000 claims 1
- UFKFMBOQSFSOAP-RVZJWNSFSA-N (1r,3r,4r)-4-[(7-chloro-3-oxo-4h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)cyclohexane-1-carboxamide Chemical compound N1C(=O)CSC(C=C2Cl)=C1N=C2CN[C@@H]([C@H](O)C1)CC[C@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 UFKFMBOQSFSOAP-RVZJWNSFSA-N 0.000 claims 1
- CYHZYFWBZFKFHI-RVZJWNSFSA-N (1r,3r,4r)-4-[(7-fluoro-3-oxo-4h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)cyclohexane-1-carboxamide Chemical compound N1C(=O)CSC(C=C2F)=C1N=C2CN[C@@H]([C@H](O)C1)CC[C@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 CYHZYFWBZFKFHI-RVZJWNSFSA-N 0.000 claims 1
- JRCHTIOVCDZDOL-QQGDVQBRSA-N (1r,3r,4r)-n-(6,8-difluoroquinolin-4-yl)-3-hydroxy-4-[(3-oxo-4h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]cyclohexane-1-carboxamide Chemical compound C1=C(F)C=C2C(NC(=O)[C@H]3C[C@H]([C@@H](CC3)NCC=3N=C4NC(=O)CSC4=CC=3)O)=CC=NC2=C1F JRCHTIOVCDZDOL-QQGDVQBRSA-N 0.000 claims 1
- BOPUCGGDXLOLLU-RFUYNDQBSA-N (1s,3s,4s)-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)-4-[(2-oxo-1h-pyrido[3,4-b][1,4]oxazin-7-yl)methylamino]cyclohexane-1-carboxamide Chemical compound N1C(=O)COC(C=N2)=C1C=C2CN[C@H]([C@@H](O)C1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 BOPUCGGDXLOLLU-RFUYNDQBSA-N 0.000 claims 1
- OIBGVZXCQRBLSA-RFUYNDQBSA-N (1s,3s,4s)-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)-4-[(2-oxo-1h-pyrido[3,4-b][1,4]thiazin-7-yl)methylamino]cyclohexane-1-carboxamide Chemical compound N1C(=O)CSC(C=N2)=C1C=C2CN[C@H]([C@@H](O)C1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 OIBGVZXCQRBLSA-RFUYNDQBSA-N 0.000 claims 1
- DQAOVLVVHPRDAI-YEWDVWPNSA-N (1s,3s,4s)-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)-4-[(6-oxo-5h-pyridazino[3,4-b][1,4]thiazin-3-yl)methylamino]cyclohexane-1-carboxamide Chemical compound N1C(=O)CSC(N=N2)=C1C=C2CN[C@H]([C@@H](O)C1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 DQAOVLVVHPRDAI-YEWDVWPNSA-N 0.000 claims 1
- TVHALYRBKNFFTC-FTRWYGJKSA-N (1s,3s,4s)-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)-4-[(7-methyl-3,4-dihydro-2h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]cyclohexane-1-carboxamide Chemical compound N1CCSC(C=C2C)=C1N=C2CN[C@H]([C@@H](O)C1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 TVHALYRBKNFFTC-FTRWYGJKSA-N 0.000 claims 1
- UFKFMBOQSFSOAP-YEWDVWPNSA-N (1s,3s,4s)-4-[(7-chloro-3-oxo-4h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)cyclohexane-1-carboxamide Chemical compound N1C(=O)CSC(C=C2Cl)=C1N=C2CN[C@H]([C@@H](O)C1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 UFKFMBOQSFSOAP-YEWDVWPNSA-N 0.000 claims 1
- CYHZYFWBZFKFHI-YEWDVWPNSA-N (1s,3s,4s)-4-[(7-fluoro-3-oxo-4h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]-3-hydroxy-n-(6-methoxy-1,5-naphthyridin-4-yl)cyclohexane-1-carboxamide Chemical compound N1C(=O)CSC(C=C2F)=C1N=C2CN[C@H]([C@@H](O)C1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 CYHZYFWBZFKFHI-YEWDVWPNSA-N 0.000 claims 1
- JRCHTIOVCDZDOL-NXXSPTCGSA-N (1s,3s,4s)-n-(6,8-difluoroquinolin-4-yl)-3-hydroxy-4-[(3-oxo-4h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]cyclohexane-1-carboxamide Chemical compound C1=C(F)C=C2C(NC(=O)[C@@H]3C[C@@H]([C@H](CC3)NCC=3N=C4NC(=O)CSC4=CC=3)O)=CC=NC2=C1F JRCHTIOVCDZDOL-NXXSPTCGSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- UDQAHFTWCBMBAL-UHFFFAOYSA-N 6,8-difluoroquinolin-4-amine Chemical compound C1=C(F)C=C2C(N)=CC=NC2=C1F UDQAHFTWCBMBAL-UHFFFAOYSA-N 0.000 claims 1
- XHJAYRSUYPCMGM-UHFFFAOYSA-N 6-(2-methoxyethoxy)-1,5-naphthyridin-4-amine Chemical compound N1=CC=C(N)C2=NC(OCCOC)=CC=C21 XHJAYRSUYPCMGM-UHFFFAOYSA-N 0.000 claims 1
- PMEDPIYDZJCMMZ-UHFFFAOYSA-N 6-[[[4-hydroxy-4-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]cyclohexyl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC3CCC(CC3)(O)CCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 PMEDPIYDZJCMMZ-UHFFFAOYSA-N 0.000 claims 1
- PHGNGVYUHOARGF-UHFFFAOYSA-N 6-methoxyquinolin-4-amine Chemical compound N1=CC=C(N)C2=CC(OC)=CC=C21 PHGNGVYUHOARGF-UHFFFAOYSA-N 0.000 claims 1
- OJLZRYSTMRWWQM-UHFFFAOYSA-N 8-fluoro-6-methoxyquinolin-4-amine Chemical compound N1=CC=C(N)C2=CC(OC)=CC(F)=C21 OJLZRYSTMRWWQM-UHFFFAOYSA-N 0.000 claims 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical compound [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- YAIJZMMUWSFXQD-QAQDUYKDSA-N C1=CC2=NSN=C2C=C1CN[C@H](CC1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)C=C21 Chemical compound C1=CC2=NSN=C2C=C1CN[C@H](CC1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)C=C21 YAIJZMMUWSFXQD-QAQDUYKDSA-N 0.000 claims 1
- WTLYHEBGJJAVMZ-WKILWMFISA-N C1=CC2=NSN=C2C=C1CN[C@H](CC1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 Chemical compound C1=CC2=NSN=C2C=C1CN[C@H](CC1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)N=C21 WTLYHEBGJJAVMZ-WKILWMFISA-N 0.000 claims 1
- QRVMGGYMIJHDPY-IYARVYRRSA-N C1=CC=C(O)C2=NC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 Chemical compound C1=CC=C(O)C2=NC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 QRVMGGYMIJHDPY-IYARVYRRSA-N 0.000 claims 1
- CFBZHYHIGXNJHA-JCNLHEQBSA-N C1=CN=C2NC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC2=C1 Chemical compound C1=CN=C2NC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC2=C1 CFBZHYHIGXNJHA-JCNLHEQBSA-N 0.000 claims 1
- DXDKEXZTHQYVLH-HOMQSWHASA-N C1C[C@@H](C(=O)O)CC[C@@H]1NCC(C(=C1)F)=CC2=C1OCC(=O)N2 Chemical compound C1C[C@@H](C(=O)O)CC[C@@H]1NCC(C(=C1)F)=CC2=C1OCC(=O)N2 DXDKEXZTHQYVLH-HOMQSWHASA-N 0.000 claims 1
- RONNYFTVWCSTTR-WKILWMFISA-N COC=1N=C2C(=CC=NC2=CC1)NC(=O)[C@@H]1CC[C@H](CC1)NCC=1C=CC2=C(N=NS2)C1 Chemical compound COC=1N=C2C(=CC=NC2=CC1)NC(=O)[C@@H]1CC[C@H](CC1)NCC=1C=CC2=C(N=NS2)C1 RONNYFTVWCSTTR-WKILWMFISA-N 0.000 claims 1
- VUWIHBMHDCCKDK-KESTWPANSA-N COc1ccc2nccc(C(=O)C[C@H]3CC[C@@H](CC3)NCc3ccc4OCCOc4c3)c2c1 Chemical compound COc1ccc2nccc(C(=O)C[C@H]3CC[C@@H](CC3)NCc3ccc4OCCOc4c3)c2c1 VUWIHBMHDCCKDK-KESTWPANSA-N 0.000 claims 1
- KXTMYJBJTDOVIC-NUDRXGSASA-N COc1ccc2nccc(C(O)C[C@H]3CC[C@@H](CC3)NCc3ccc4OCCOc4c3)c2c1 Chemical compound COc1ccc2nccc(C(O)C[C@H]3CC[C@@H](CC3)NCc3ccc4OCCOc4c3)c2c1 KXTMYJBJTDOVIC-NUDRXGSASA-N 0.000 claims 1
- AAEQFPGZGKQMJG-KOMQPUFPSA-N COc1ccc2nccc(NC(=O)[C@H]3CC[C@@H](CC3)NCc3cc4OCOc4cc3N)c2n1 Chemical compound COc1ccc2nccc(NC(=O)[C@H]3CC[C@@H](CC3)NCc3cc4OCOc4cc3N)c2n1 AAEQFPGZGKQMJG-KOMQPUFPSA-N 0.000 claims 1
- CVGDZQMKRYTPRE-QAQDUYKDSA-N COc1ccc2nccc(NC(=O)[C@H]3CC[C@@H](CC3)NCc3ccc4scnc4c3)c2n1 Chemical compound COc1ccc2nccc(NC(=O)[C@H]3CC[C@@H](CC3)NCc3ccc4scnc4c3)c2n1 CVGDZQMKRYTPRE-QAQDUYKDSA-N 0.000 claims 1
- PSPLWQAGYAUAGS-HAQNSBGRSA-N Cn1c2ccc(CN[C@H]3CC[C@@H](CC3)C(O)=O)cc2oc1=O Chemical compound Cn1c2ccc(CN[C@H]3CC[C@@H](CC3)C(O)=O)cc2oc1=O PSPLWQAGYAUAGS-HAQNSBGRSA-N 0.000 claims 1
- WESVMUHKPRCJHK-KOMQPUFPSA-N N([C@H]1CC[C@@H](CC1)C(=O)NC1=CC=NC2=CC=C(N=C21)OC)CC(C(=C1)[N+]([O-])=O)=CC2=C1OCO2 Chemical compound N([C@H]1CC[C@@H](CC1)C(=O)NC1=CC=NC2=CC=C(N=C21)OC)CC(C(=C1)[N+]([O-])=O)=CC2=C1OCO2 WESVMUHKPRCJHK-KOMQPUFPSA-N 0.000 claims 1
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- LXMYTYOWYIYDRP-UHFFFAOYSA-N N1=CC=C(N)C2=NC(C)=CC=C21 Chemical compound N1=CC=C(N)C2=NC(C)=CC=C21 LXMYTYOWYIYDRP-UHFFFAOYSA-N 0.000 claims 1
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2001
- 2001-05-25 GB GBGB0112834.7A patent/GB0112834D0/en not_active Ceased
-
2002
- 2002-05-23 AR ARP020101914A patent/AR038172A1/es not_active Application Discontinuation
- 2002-05-23 TW TW091110839A patent/TWI232219B/zh not_active IP Right Cessation
- 2002-05-24 HU HU0400017A patent/HUP0400017A2/hu unknown
- 2002-05-24 MX MXPA03010790A patent/MXPA03010790A/es unknown
- 2002-05-24 AT AT02807202T patent/ATE380812T1/de not_active IP Right Cessation
- 2002-05-24 CZ CZ20033202A patent/CZ20033202A3/cs unknown
- 2002-05-24 BR BR0210016-9A patent/BR0210016A/pt not_active IP Right Cessation
- 2002-05-24 CN CNA028146689A patent/CN1535272A/zh active Pending
- 2002-05-24 EP EP02807202A patent/EP1399443B1/en not_active Expired - Lifetime
- 2002-05-24 IL IL15886902A patent/IL158869A0/xx unknown
- 2002-05-24 DE DE60224039T patent/DE60224039T2/de not_active Expired - Lifetime
- 2002-05-24 CA CA002448525A patent/CA2448525A1/en not_active Abandoned
- 2002-05-24 JP JP2003584054A patent/JP4463565B2/ja not_active Expired - Fee Related
- 2002-05-24 US US10/478,154 patent/US7141564B2/en not_active Expired - Fee Related
- 2002-05-24 WO PCT/EP2002/005708 patent/WO2003087098A1/en not_active Ceased
- 2002-05-24 ES ES02807202T patent/ES2298439T3/es not_active Expired - Lifetime
- 2002-05-24 KR KR10-2003-7015379A patent/KR20040010654A/ko not_active Withdrawn
- 2002-05-24 AU AU2002367697A patent/AU2002367697A1/en not_active Abandoned
- 2002-05-24 PL PL02367079A patent/PL367079A1/xx not_active Application Discontinuation
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2003
- 2003-11-07 ZA ZA200308696A patent/ZA200308696B/en unknown
- 2003-11-18 CO CO03101671A patent/CO5540344A2/es not_active Application Discontinuation
- 2003-11-21 NO NO20035190A patent/NO20035190D0/no not_active Application Discontinuation
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2006
- 2006-11-22 US US11/604,045 patent/US20070135422A1/en not_active Abandoned
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2009
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