JP2004520360A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2004520360A5 JP2004520360A5 JP2002557390A JP2002557390A JP2004520360A5 JP 2004520360 A5 JP2004520360 A5 JP 2004520360A5 JP 2002557390 A JP2002557390 A JP 2002557390A JP 2002557390 A JP2002557390 A JP 2002557390A JP 2004520360 A5 JP2004520360 A5 JP 2004520360A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- alkyl
- piperidin
- methoxy
- ethyl
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims 49
- -1 amino, piperidyl Chemical group 0.000 claims 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 17
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 12
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 12
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims 12
- 125000003277 amino group Chemical group 0.000 claims 12
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 8
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 6
- 125000004414 alkyl thio group Chemical group 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 3
- 125000000229 (C1-C4)alkoxy 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000005035 acylthio group Chemical group 0.000 claims 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 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
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- RBBMMMJYPLTDJJ-VWLOTQADSA-N (1r)-1-(6-methoxyquinolin-4-yl)-2-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-ylmethylamino)piperidin-1-yl]ethanol Chemical compound C1CCNC2=NC(CNC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 RBBMMMJYPLTDJJ-VWLOTQADSA-N 0.000 claims 1
- AKVZCTPKTKXUFZ-QHCPKHFHSA-N (1r)-1-(6-methoxyquinolin-4-yl)-2-[4-[(6-nitro-1,3-benzodioxol-5-yl)methylamino]piperidin-1-yl]ethanol Chemical compound C([C@H](O)C1=CC=NC2=CC=C(C=C21)OC)N(CC1)CCC1NCC(C(=C1)[N+]([O-])=O)=CC2=C1OCO2 AKVZCTPKTKXUFZ-QHCPKHFHSA-N 0.000 claims 1
- YXGCEBKQJZAGQL-QHCPKHFHSA-N (1r)-2-[4-(1,3-benzodioxol-5-ylmethylamino)piperidin-1-yl]-1-(6-methoxyquinolin-4-yl)ethanol Chemical compound C1=C2OCOC2=CC(CNC2CCN(CC2)C[C@H](O)C2=CC=NC3=CC=C(C=C32)OC)=C1 YXGCEBKQJZAGQL-QHCPKHFHSA-N 0.000 claims 1
- WZCJTDWSEDVQNY-DEOSSOPVSA-N (1r)-2-[4-(2,3-dihydro-1,4-benzodioxin-6-ylmethylamino)piperidin-1-yl]-1-(6-methoxyquinolin-4-yl)ethanol Chemical compound O1CCOC2=CC(CNC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 WZCJTDWSEDVQNY-DEOSSOPVSA-N 0.000 claims 1
- CIYIYWQDQTXPMR-DEOSSOPVSA-N (1r)-2-[4-(2,3-dihydro-1h-pyrido[2,3-b][1,4]thiazin-7-ylmethylamino)piperidin-1-yl]-1-(6-methoxyquinolin-4-yl)ethanol Chemical compound S1CCNC2=CC(CNC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(C=C43)OC)=CN=C21 CIYIYWQDQTXPMR-DEOSSOPVSA-N 0.000 claims 1
- IQTIWIZDWUXWDH-QHCPKHFHSA-N (1r)-2-[4-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-ylmethylamino)piperidin-1-yl]-1-(6-methoxyquinolin-4-yl)ethanol Chemical compound O1CCOC2=NC(CNC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 IQTIWIZDWUXWDH-QHCPKHFHSA-N 0.000 claims 1
- OUPJUDPIEJTOPK-FQEVSTJZSA-N (1r)-2-[4-(3,4-dihydro-2h-pyrido[3,2-b][1,4]thiazin-6-ylmethylamino)piperidin-1-yl]-1-(6-methoxy-1,5-naphthyridin-4-yl)ethanol Chemical compound S1CCNC2=NC(CNC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 OUPJUDPIEJTOPK-FQEVSTJZSA-N 0.000 claims 1
- SIUXHCYRZKHSTR-QHCPKHFHSA-N (1r)-2-[4-(3,4-dihydro-2h-pyrido[3,2-b][1,4]thiazin-6-ylmethylamino)piperidin-1-yl]-1-(6-methoxyquinolin-4-yl)ethanol Chemical compound S1CCNC2=NC(CNC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 SIUXHCYRZKHSTR-QHCPKHFHSA-N 0.000 claims 1
- UQKCHSYMXQWFMW-QHCPKHFHSA-N (1r)-2-[4-[(6-chloro-1,3-benzodioxol-5-yl)methylamino]piperidin-1-yl]-1-(6-methoxyquinolin-4-yl)ethanol Chemical compound C([C@H](O)C1=CC=NC2=CC=C(C=C21)OC)N(CC1)CCC1NCC(C(=C1)Cl)=CC2=C1OCO2 UQKCHSYMXQWFMW-QHCPKHFHSA-N 0.000 claims 1
- OWQNDGWKMBNZOX-NRFANRHFSA-N (1r)-2-[4-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-7-yl)methylamino]piperidin-1-yl]-1-(6-methoxy-1,5-naphthyridin-4-yl)ethanol Chemical compound O1CCOC(C=C2F)=C1C=C2CNC(CC1)CCN1C[C@H](O)C1=CC=NC2=CC=C(OC)N=C21 OWQNDGWKMBNZOX-NRFANRHFSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- OYYHTHWUDCUBQV-UHFFFAOYSA-N 1,4-thiazin-2-one Chemical compound O=C1C=NC=CS1 OYYHTHWUDCUBQV-UHFFFAOYSA-N 0.000 claims 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical group CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims 1
- SZHYPQDQYNLZJP-UHFFFAOYSA-N 3-oxo-4h-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid Chemical compound S1CC(=O)NC2=NC(C(=O)O)=CC=C21 SZHYPQDQYNLZJP-UHFFFAOYSA-N 0.000 claims 1
- XISPDFMAOWZEQG-UHFFFAOYSA-N 4h-1,4-oxazin-3-one Chemical compound O=C1COC=CN1 XISPDFMAOWZEQG-UHFFFAOYSA-N 0.000 claims 1
- UIRSLBDCOYTZPH-UHFFFAOYSA-N 4h-1,4-thiazin-3-one Chemical compound O=C1CSC=CN1 UIRSLBDCOYTZPH-UHFFFAOYSA-N 0.000 claims 1
- GAGAICHLGQDUTL-UHFFFAOYSA-N 4h-thiazin-3-one Chemical compound O=C1CC=CSN1 GAGAICHLGQDUTL-UHFFFAOYSA-N 0.000 claims 1
- WFPGYFRYIRNCNS-DEOSSOPVSA-N 5-fluoro-6-[[[1-[(2r)-2-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-3-methyl-1,3-benzoxazol-2-one Chemical compound C([C@H](O)C1=CC=NC2=CC=C(C=C21)OC)N(CC1)CCC1NCC(C(=C1)F)=CC2=C1N(C)C(=O)O2 WFPGYFRYIRNCNS-DEOSSOPVSA-N 0.000 claims 1
- OPAAZANXDHQVPI-NRFANRHFSA-N 6-[[[1-[(2r)-2-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-1,4-benzothiazin-3-one Chemical compound S1CC(=O)NC2=CC(CNC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 OPAAZANXDHQVPI-NRFANRHFSA-N 0.000 claims 1
- OHDMXSQSXYADHZ-NRFANRHFSA-N 6-[[[1-[(2r)-2-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(CNC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 OHDMXSQSXYADHZ-NRFANRHFSA-N 0.000 claims 1
- XOJAZZVOEWKCAZ-DEOSSOPVSA-N 6-[[[1-[(2r)-2-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-3-methyl-1,3-benzoxazol-2-one Chemical compound C1=C2N(C)C(=O)OC2=CC(CNC2CCN(CC2)C[C@H](O)C2=CC=NC3=CC=C(C=C32)OC)=C1 XOJAZZVOEWKCAZ-DEOSSOPVSA-N 0.000 claims 1
- GNWHDFGJPRKJTC-DEOSSOPVSA-N 6-[[[1-[(2r)-2-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-3-methyl-1,3-benzoxazole-2-thione Chemical compound C1=C2N(C)C(=S)OC2=CC(CNC2CCN(CC2)C[C@H](O)C2=CC=NC3=CC=C(C=C32)OC)=C1 GNWHDFGJPRKJTC-DEOSSOPVSA-N 0.000 claims 1
- JBXWVEMLTDXSCR-DEOSSOPVSA-N 6-[[[1-[(2r)-2-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-1,4-benzothiazin-3-one Chemical compound S1CC(=O)NC2=CC(CNC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 JBXWVEMLTDXSCR-DEOSSOPVSA-N 0.000 claims 1
- ZSFFWCNXJDGECL-DEOSSOPVSA-N 6-[[[1-[(2r)-2-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(CNC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 ZSFFWCNXJDGECL-DEOSSOPVSA-N 0.000 claims 1
- QDTLTBXLSFBPEM-QFIPXVFZSA-N 6-[[[1-[(2r)-2-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 QDTLTBXLSFBPEM-QFIPXVFZSA-N 0.000 claims 1
- HFDLDPJYCIEXJP-UHFFFAOYSA-N 6-methoxyquinoline Chemical compound N1=CC=CC2=CC(OC)=CC=C21 HFDLDPJYCIEXJP-UHFFFAOYSA-N 0.000 claims 1
- HIXTTZIJAWUHCI-FQEVSTJZSA-N 7-[[[1-[(2r)-2-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-1h-pyrido[2,3-b][1,4]thiazin-2-one Chemical compound S1CC(=O)NC2=CC(CNC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(N=C43)OC)=CN=C21 HIXTTZIJAWUHCI-FQEVSTJZSA-N 0.000 claims 1
- ORRVDYWUNUCTCY-VWLOTQADSA-N 7-[[[1-[(2r)-2-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-3,5-dihydro-2h-1,5-benzothiazepin-4-one Chemical compound S1CCC(=O)NC2=CC(CNC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 ORRVDYWUNUCTCY-VWLOTQADSA-N 0.000 claims 1
- SHVJDPNOVPQBCL-IBGZPJMESA-N 7-bromo-6-[[[1-[(2r)-2-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound N1C(=O)CSC(C=C2Br)=C1N=C2CNC(CC1)CCN1C[C@H](O)C1=CC=NC2=CC=C(OC)N=C21 SHVJDPNOVPQBCL-IBGZPJMESA-N 0.000 claims 1
- DMLZEPCPSMFQRG-KRWDZBQOSA-N 7-bromo-n-[1-[(2r)-2-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]piperidin-4-yl]-3-oxo-4h-pyrido[3,2-b][1,4]thiazine-6-carboxamide Chemical compound N1C(=O)CSC(C=C2Br)=C1N=C2C(=O)NC(CC1)CCN1C[C@H](O)C1=CC=NC2=CC=C(OC)N=C21 DMLZEPCPSMFQRG-KRWDZBQOSA-N 0.000 claims 1
- YPJMANDEZYYSRE-FQEVSTJZSA-N 7-bromo-n-[1-[(2r)-2-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperidin-4-yl]-3-oxo-4h-pyrido[3,2-b][1,4]thiazine-6-carboxamide Chemical compound N1C(=O)CSC(C=C2Br)=C1N=C2C(=O)NC(CC1)CCN1C[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 YPJMANDEZYYSRE-FQEVSTJZSA-N 0.000 claims 1
- YWRKWLVHPFBAJS-NRFANRHFSA-N 7-fluoro-6-[[[1-[(2r)-2-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-1,4-benzothiazin-3-one Chemical compound N1C(=O)CSC(C=C2F)=C1C=C2CNC(CC1)CCN1C[C@H](O)C1=CC=NC2=CC=C(OC)N=C21 YWRKWLVHPFBAJS-NRFANRHFSA-N 0.000 claims 1
- ICNZKASFSKJTIH-DEOSSOPVSA-N 7-fluoro-6-[[[1-[(2r)-2-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-1,4-benzothiazin-3-one Chemical compound N1C(=O)CSC(C=C2F)=C1C=C2CNC(CC1)CCN1C[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ICNZKASFSKJTIH-DEOSSOPVSA-N 0.000 claims 1
- JAJVSMJTXIDLRT-DEOSSOPVSA-N 7-fluoro-6-[[[1-[(2r)-2-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-1,4-benzoxazin-3-one Chemical compound N1C(=O)COC(C=C2F)=C1C=C2CNC(CC1)CCN1C[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 JAJVSMJTXIDLRT-DEOSSOPVSA-N 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000005361 aryl sulfoxide group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 1
- 125000004468 heterocyclylthio group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- CXKQTWYOKDJYCC-SFHVURJKSA-N n-[1-[(2r)-2-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]piperidin-4-yl]-3-oxo-4h-pyrido[3,2-b][1,4]thiazine-6-carboxamide Chemical compound S1CC(=O)NC2=NC(C(=O)NC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 CXKQTWYOKDJYCC-SFHVURJKSA-N 0.000 claims 1
- MWMMKZFAGJCOKL-NRFANRHFSA-N n-[1-[(2r)-2-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]piperidin-4-yl]-4-oxo-3,5-dihydro-2h-1,5-benzothiazepine-7-sulfonamide Chemical compound S1CCC(=O)NC2=CC(S(=O)(=O)NC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 MWMMKZFAGJCOKL-NRFANRHFSA-N 0.000 claims 1
- CBSYFDWHOUSOBP-QHCPKHFHSA-N n-[1-[(2r)-2-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperidin-4-yl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide Chemical compound O1CCOC2=CC(C(=O)NC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 CBSYFDWHOUSOBP-QHCPKHFHSA-N 0.000 claims 1
- UFMASMIVYIHNGW-QHCPKHFHSA-N n-[1-[(2r)-2-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperidin-4-yl]-3-oxo-4h-1,4-benzothiazine-6-sulfonamide Chemical compound S1CC(=O)NC2=CC(S(=O)(=O)NC3CCN(CC3)C[C@H](O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 UFMASMIVYIHNGW-QHCPKHFHSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0101577.5A GB0101577D0 (en) | 2001-01-22 | 2001-01-22 | Compounds |
| PCT/EP2002/000587 WO2002056882A1 (en) | 2001-01-22 | 2002-01-22 | Quinolines and nitrogenated derivaive thereof substituted in 4-position by a piperidine-containing moiety and their use as antibacterial agents |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009251653A Division JP2010024246A (ja) | 2001-01-22 | 2009-11-02 | ４位がピペリジン含有部分によって置換されたキノリンおよびその窒素化誘導体および抗菌薬としてのその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004520360A JP2004520360A (ja) | 2004-07-08 |
| JP2004520360A5 true JP2004520360A5 (https=) | 2005-12-22 |
| JP4472928B2 JP4472928B2 (ja) | 2010-06-02 |
Family
ID=9907232
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002557390A Expired - Lifetime JP4472928B2 (ja) | 2001-01-22 | 2002-01-22 | ４位がピペリジン含有部分によって置換されたキノリンおよびその窒素化誘導体および抗菌薬としてのその使用 |
| JP2009251653A Pending JP2010024246A (ja) | 2001-01-22 | 2009-11-02 | ４位がピペリジン含有部分によって置換されたキノリンおよびその窒素化誘導体および抗菌薬としてのその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009251653A Pending JP2010024246A (ja) | 2001-01-22 | 2009-11-02 | ４位がピペリジン含有部分によって置換されたキノリンおよびその窒素化誘導体および抗菌薬としてのその使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7205408B2 (https=) |
| EP (1) | EP1359908B1 (https=) |
| JP (2) | JP4472928B2 (https=) |
| AT (1) | ATE370731T1 (https=) |
| DE (1) | DE60221969T2 (https=) |
| ES (1) | ES2292716T3 (https=) |
| GB (1) | GB0101577D0 (https=) |
| WO (1) | WO2002056882A1 (https=) |
Families Citing this family (96)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6803369B1 (en) | 2000-07-25 | 2004-10-12 | Smithkline Beecham Corporation | Compounds and methods for the treatment of neoplastic disease |
| EP1305308B1 (en) | 2000-07-26 | 2006-12-20 | Smithkline Beecham Plc | Aminopiperidine quinolines and their azaisosteric analogues with antibacterial activity |
| WO2002024684A1 (en) * | 2000-09-21 | 2002-03-28 | Smithkline Beecham P.L.C. | Quinoline derivatives as antibacterials |
| GB0031086D0 (en) * | 2000-12-20 | 2001-01-31 | Smithkline Beecham Plc | Medicaments |
| GB0031088D0 (en) * | 2000-12-20 | 2001-01-31 | Smithkline Beecham Plc | Medicaments |
| 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 |
| EP1470131A2 (en) | 2002-01-29 | 2004-10-27 | Glaxo Group Limited | Aminopiperidine compounds, process for their preparation, and pharmaceutical compositions containing them |
| US7312212B2 (en) * | 2002-01-29 | 2007-12-25 | Glaxo Group Limited | Aminopiperidine derivatives |
| US6924285B2 (en) | 2002-03-30 | 2005-08-02 | Boehringer Ingelheim Pharma Gmbh & Co. | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| GB0209244D0 (en) * | 2002-04-23 | 2002-06-05 | Glaxo Group Ltd | Compounds |
| 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 |
| EP1551829B1 (de) * | 2002-10-10 | 2010-04-07 | Morphochem Aktiengesellschaft Für Kombinatorische Chemie | Neue verbindungen mit antibakterieller aktivität |
| DE10256405A1 (de) * | 2002-12-02 | 2004-06-17 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Neue Verbindungen, die Topoisomerase IV inhibieren |
| EP1560488B1 (en) | 2002-11-05 | 2010-09-01 | Glaxo Group Limited | Antibacterial agents |
| US7232832B2 (en) | 2002-11-05 | 2007-06-19 | Smithkline Beecham Corporation | Antibacterial agents |
| WO2004050036A2 (en) | 2002-12-04 | 2004-06-17 | Glaxo Group Limited | Quinolines and nitrogenated derivatives thereof and their use as antibacterial agents |
| AR042486A1 (es) * | 2002-12-18 | 2005-06-22 | Glaxo Group Ltd | Compuesto de quinolina y naftiridina halosustituido en la posicion 3, procedimiento para preparar el compuesto, composicion farmaceutica que lo comprende y su uso para preparar dicha composicion . |
| DK1603570T5 (da) | 2003-02-26 | 2013-12-09 | Sugen Inc | Aminoheteroarylforbindelser som proteinkinaseinhibitorer |
| TW200507841A (en) * | 2003-03-27 | 2005-03-01 | Glaxo Group Ltd | Antibacterial agents |
| US7160888B2 (en) | 2003-08-22 | 2007-01-09 | Warner Lambert Company Llc | [1,8]naphthyridin-2-ones and related compounds for the treatment of schizophrenia |
| WO2005028467A1 (en) * | 2003-09-15 | 2005-03-31 | Anadys Pharmaceuticals, Inc. | Antibacterial 3,5-diaminopiperidine-substitute aromatic and heteroaromatic compounds |
| ATE395346T1 (de) | 2003-09-16 | 2008-05-15 | Astrazeneca Ab | Chinazolinderivate als tyrosinkinaseinhibitoren |
| GB0322409D0 (en) | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| EA011277B1 (ru) | 2004-01-23 | 2009-02-27 | Янссен Фармацевтика Н.В. | Производные хинолина и их применение в качестве ингибиторов микобактерий |
| DE602005010824D1 (de) | 2004-02-03 | 2008-12-18 | Astrazeneca Ab | Chinazolinderivate |
| WO2006002047A2 (en) | 2004-06-15 | 2006-01-05 | Glaxo Group Limited | Antibacterial agents |
| JP2008505920A (ja) * | 2004-07-08 | 2008-02-28 | グラクソ グループ リミテッド | 抗菌剤 |
| WO2006017468A2 (en) | 2004-08-02 | 2006-02-16 | Glaxo Group Limited | Antibacterial agents |
| JP2008509222A (ja) * | 2004-08-09 | 2008-03-27 | グラクソ グループ リミテッド | 抗菌剤 |
| TW200630337A (en) * | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
| DE102004057645A1 (de) * | 2004-11-29 | 2006-06-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Substituierte Pteridine zur Behandlung von entzündlichen Erkrankungen |
| DE102004057595A1 (de) | 2004-11-29 | 2006-06-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Substituierte Pteridine zur Behandlung von entzündlichen Erkrankungen |
| DE102004057594A1 (de) * | 2004-11-29 | 2006-06-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Substitueirte Pteridine zur Behandlung von entzündlichen Erkrankungen |
| DE102004057618A1 (de) * | 2004-11-29 | 2006-06-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Substituierte Pteridine zur Behandlung von entzündlichen Erkrankungen |
| WO2006081182A2 (en) | 2005-01-25 | 2006-08-03 | Glaxo Group Limited | Antibacterial agents |
| JP2008528586A (ja) | 2005-01-25 | 2008-07-31 | グラクソ グループ リミテッド | 抗菌剤 |
| US7511035B2 (en) * | 2005-01-25 | 2009-03-31 | Glaxo Group Limited | Antibacterial agents |
| JP2008528598A (ja) | 2005-01-25 | 2008-07-31 | グラクソ グループ リミテッド | 抗菌剤 |
| EP1845995A4 (en) * | 2005-01-25 | 2010-03-03 | Glaxo Group Ltd | ANTIBACTERIAL AGENTS |
| JP5023054B2 (ja) | 2005-03-31 | 2012-09-12 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 抗バクテリア剤としての二環式ピラゾール化合物 |
| MY150958A (en) | 2005-06-16 | 2014-03-31 | Astrazeneca Ab | Compounds for the treatment of multi-drug resistant bacterial infections |
| EP1900732A4 (en) | 2005-06-24 | 2009-11-18 | Toyama Chemical Co Ltd | NEW NITROGENATED HETEROCYCLIC COMPOUND AND SALT THEREOF |
| JO2837B1 (en) * | 2005-08-03 | 2014-09-15 | جانسن فارمسيتكا ان في | Quinoline derivatives acting as antibacterial agents |
| JO2952B1 (en) * | 2005-08-03 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Quinoline derivatives acting as antibacterial agents |
| ES2340531T3 (es) * | 2005-10-21 | 2010-06-04 | Glaxo Group Limited | Compuestos triciclos peri-condensados utiles como agentes antibacterianos. |
| DK1963302T3 (da) * | 2005-12-05 | 2013-04-02 | Pfizer Prod Inc | Polymorfer af en C-MET/HGFR-inhibitor |
| PL1959955T3 (pl) * | 2005-12-05 | 2011-04-29 | Pfizer Prod Inc | Sposób traktowania nieprawidłowego wzrostu komórek |
| ATE465163T1 (de) * | 2005-12-22 | 2010-05-15 | Glaxo Group Ltd | Heterocyclische verbindungen, ihre herstellung und ihre verwendung als antibakterielle mittel |
| ATE536351T1 (de) | 2006-01-26 | 2011-12-15 | Actelion Pharmaceuticals Ltd | Tetrahydropyran-antibiotika |
| WO2007098214A1 (en) * | 2006-02-21 | 2007-08-30 | Amgen Inc. | Cinnoline derivatives as phosphodiesterase 10 inhibitors |
| WO2007103554A1 (en) * | 2006-03-08 | 2007-09-13 | Amgen Inc. | Quinoline and isoquinoline derivatives as phosphodiesterase 10 inhibitors |
| EP2001478B1 (en) | 2006-03-23 | 2010-06-02 | Actelion Pharmaceuticals Ltd. | Cyclohexyl or piperidinyl carboxamide antibiotic derivatives |
| WO2007110449A1 (en) * | 2006-03-29 | 2007-10-04 | Euro-Celtique S.A. | Benzenesulfonamide compounds and their use |
| EP2001887B1 (en) | 2006-04-06 | 2010-09-15 | Glaxo Group Limited | Pyrrolo-quinoxalinone derivatives as antibacterials |
| WO2007118130A2 (en) | 2006-04-06 | 2007-10-18 | Glaxo Group Limited | Antibacterial agents |
| US8791264B2 (en) * | 2006-04-13 | 2014-07-29 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use as blockers of calcium channels |
| WO2007118854A1 (en) * | 2006-04-13 | 2007-10-25 | Euro-Celtique S.A. | Benzenesulfonamide compounds and the use thereof |
| GB0608263D0 (en) * | 2006-04-26 | 2006-06-07 | Glaxo Group Ltd | Compounds |
| AU2007268749B2 (en) | 2006-05-26 | 2012-07-26 | Taisho Pharmaceutical Co., Ltd. | Novel heterocyclic compound or salt thereof and intermediate thereof |
| GB0613208D0 (en) | 2006-07-03 | 2006-08-09 | Glaxo Group Ltd | Compounds |
| EP1992628A1 (en) | 2007-05-18 | 2008-11-19 | Glaxo Group Limited | Derivatives and analogs of N-ethylquinolones and N-ethylazaquinolones |
| EP1921070A1 (de) | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstelllung |
| WO2008071964A1 (en) * | 2006-12-15 | 2008-06-19 | Astrazeneca Ab | Naphthyridine bactericides |
| AU2008212999A1 (en) | 2007-02-06 | 2008-08-14 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles, drugs containing said compounds, use thereof, and method for production thereof |
| WO2008124118A1 (en) * | 2007-04-09 | 2008-10-16 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use therof |
| AU2008240764C1 (en) * | 2007-04-20 | 2011-10-20 | Glaxo Group Limited | Tricyclic nitrogen containing compounds as antibacterial agents |
| WO2009040659A2 (en) * | 2007-09-28 | 2009-04-02 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| CN101874032B (zh) | 2007-11-26 | 2013-02-06 | 富山化学工业株式会社 | 二氮杂萘衍生物一水合物及其制备方法 |
| GB0800367D0 (en) * | 2008-01-09 | 2008-02-20 | Glaxo Group Ltd | Compounds |
| EP2080761A1 (en) | 2008-01-18 | 2009-07-22 | Glaxo Group Limited | Compounds |
| US8497369B2 (en) | 2008-02-07 | 2013-07-30 | Boehringer Ingelheim International Gmbh | Spirocyclic heterocycles medicaments containing said compounds, use thereof and method for their production |
| KR101592046B1 (ko) | 2008-02-22 | 2016-02-05 | 액테리온 파마슈티칼 리미티드 | 옥사졸리디논 유도체 |
| TW200944529A (en) | 2008-04-15 | 2009-11-01 | Actelion Pharmaceuticals Ltd | Tricyclic antibiotics |
| JP5739802B2 (ja) | 2008-05-13 | 2015-06-24 | アストラゼネカ アクチボラグ | ４−（３−クロロ−２−フルオロアニリノ）−７−メトキシ−６−｛［１−（ｎ−メチルカルバモイルメチル）ピペリジン−４−イル］オキシ｝キナゾリンのフマル酸塩 |
| MX2010012855A (es) | 2008-06-03 | 2010-12-21 | Actelion Pharmaceuticals Ltd | Derivados de [4-(1-amino-etil)-ciclohexil]-metil-amina y [6-(1-amino-etil)-tetrahidro-piran-3-il]-metil-amina como antibacterianos. |
| EP2313397B1 (de) | 2008-08-08 | 2016-04-20 | Boehringer Ingelheim International GmbH | Cyclohexyloxy-substituierte heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| EP2352734A1 (en) | 2008-10-17 | 2011-08-10 | Glaxo Group Limited | Tricyclic nitrogen compounds used as antibacterials |
| AU2009325902B2 (en) | 2008-12-12 | 2015-01-29 | Idorsia Pharmaceuticals Ltd | 5-amino-2-(1-hydroxy-ethyl)-tetrahydropyran derivatives |
| US8318940B2 (en) | 2009-01-15 | 2012-11-27 | Glaxo Group Limited | Naphthyridin-2 (1 H)-one compounds useful as antibacterials |
| EP2332939A1 (en) | 2009-11-26 | 2011-06-15 | Æterna Zentaris GmbH | Novel Naphthyridine derivatives and the use thereof as kinase inhibitors |
| TW201326180A (zh) | 2011-11-30 | 2013-07-01 | Actelion Pharmaceuticals Ltd | ３，７－二取代八氫－２Ｈ－吡啶并［４，３－ｅ］［１，３］□嗪－２－酮抗生素 |
| AR089929A1 (es) | 2012-02-10 | 2014-10-01 | Actelion Pharmaceuticals Ltd | Proceso para manufacturar un derivado de naftiridina |
| CA2887375C (en) * | 2012-10-10 | 2022-07-05 | Vitas Pharma Research Pvt Ltd | Inhibitors of dna gyrase for the treatment of bacterial infections |
| TW201429972A (zh) | 2013-01-09 | 2014-08-01 | Actelion Pharmaceuticals Ltd | 抗菌噁唑酮衍生物 |
| AR096135A1 (es) * | 2013-05-02 | 2015-12-09 | Actelion Pharmaceuticals Ltd | Derivados de la quinolona |
| US10702521B2 (en) | 2014-08-22 | 2020-07-07 | Glaxosmithkline Intellectual Property Development Limited | Methods for treating neisseria gonorrhoeae infection with substituted 1,2-dihydro-2A,5,8A-triazaacenaphthylene-3,8-diones |
| TW201722965A (zh) | 2015-08-16 | 2017-07-01 | 葛蘭素史密斯克藍智慧財產發展有限公司 | 用於抗菌應用之化合物 |
| US12479816B2 (en) | 2019-02-08 | 2025-11-25 | University of Pittsburgh—of the Commonwealth System of Higher Education | 20-HETE formation inhibitors |
| WO2020169593A1 (en) | 2019-02-19 | 2020-08-27 | Univerza V Ljubljani | Antibacterials based on monocyclic fragments coupled to aminopiperidine naphthyridine scaffold |
| KR20220087497A (ko) | 2019-10-18 | 2022-06-24 | 더 리전츠 오브 더 유니버시티 오브 캘리포니아 | 병원성 혈관을 표적화하기 위한 화합물 및 방법 |
| US12590298B2 (en) | 2019-10-18 | 2026-03-31 | The Regents Of The University Of California | Ex vivo tumor angiogenesis model |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1345872A (en) | 1970-09-03 | 1974-02-06 | Wyeth John & Brother Ltd | Amino-and acylamino-pyridine and hydropyridine derivatives |
| GB1537867A (en) | 1977-07-04 | 1979-01-04 | Wyeth John & Brother Ltd | Process for preparing 4-acylamino-piperidine derivatives |
| US4925877A (en) | 1986-02-25 | 1990-05-15 | Zaidanhojin Biseibutsu Kagaku Kenkyukai | Physiologically active erbstatin analogue compounds and compositions |
| US4971996A (en) | 1987-03-11 | 1990-11-20 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Hydroxystyrene compounds which are useful as tyrosine kinase inhibitors |
| ZA899436B (en) | 1988-12-12 | 1990-08-29 | Ciba Geigy | Piperidine derivatives |
| MY110227A (en) * | 1991-08-12 | 1998-03-31 | Ciba Geigy Ag | 1-acylpiperindine compounds. |
| EP0541486A1 (de) * | 1991-11-07 | 1993-05-12 | Ciba-Geigy Ag | Polycyclische Konjugate |
| PT672041E (pt) | 1993-10-01 | 2002-04-29 | Novartis Ag | Derivados da piridina farmacologicamente activos e processos para a sua preparacao |
| JPH07179407A (ja) | 1993-11-12 | 1995-07-18 | Green Cross Corp:The | 新規縮合環系化合物またはその塩、およびその医薬用途 |
| PL181893B1 (pl) | 1994-11-14 | 2001-10-31 | Warner Lambert Co | Zwiazki bedace pochodnymi pirymidyny i naftyrydyny oraz preparat farmaceutyczny zawierajacy je PL PL PL |
| ES2149468T3 (es) | 1995-04-26 | 2000-11-01 | Kyowa Hakko Kogyo Kk | Derivados de radicicol. |
| US5620997A (en) | 1995-05-31 | 1997-04-15 | Warner-Lambert Company | Isothiazolones |
| GB9514265D0 (en) | 1995-07-13 | 1995-09-13 | Wellcome Found | Hetrocyclic compounds |
| US6077857A (en) | 1995-11-13 | 2000-06-20 | Smithkline Beecham Corporation | Hemoregulatory compounds |
| US5707990A (en) | 1996-01-30 | 1998-01-13 | Ortho Pharmaceutical Corporation | 2-substituted amino and thio alkyl benzoxazine antimicrobial agents |
| AU2898297A (en) | 1996-05-24 | 1998-01-05 | Novartis Ag | Use of substance p antagonists for treating social phobia |
| HRP970371A2 (en) | 1996-07-13 | 1998-08-31 | Kathryn Jane Smith | Heterocyclic compounds |
| CA2318842A1 (en) | 1998-01-26 | 1999-07-29 | Julie Dorothy Warrack | Quinoline derivatives as antibacterials |
| GB9822450D0 (en) * | 1998-10-14 | 1998-12-09 | Smithkline Beecham Plc | Medicaments |
| GB9822440D0 (en) | 1998-10-14 | 1998-12-09 | Smithkline Beecham Plc | Medicaments |
| JP2002535323A (ja) | 1999-01-20 | 2002-10-22 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | プロテインキナーゼ阻害剤としてのピペリジニルキノリン |
| GB9914486D0 (en) * | 1999-06-21 | 1999-08-18 | Smithkline Beecham Plc | Medicaments |
| GB9917406D0 (en) | 1999-07-23 | 1999-09-22 | Smithkline Beecham Plc | Compounds |
| GB9917408D0 (en) * | 1999-07-23 | 1999-09-22 | Smithkline Beecham Plc | Compounds |
| 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 |
| US6403610B1 (en) * | 1999-09-17 | 2002-06-11 | Aventis Pharma S.A. | Quinolylpropylpiperidine derivatives, their preparation and the compositions which comprise them |
| GB0011838D0 (en) | 2000-05-17 | 2000-07-05 | Astrazeneca Ab | Chemical compounds |
| US6803369B1 (en) * | 2000-07-25 | 2004-10-12 | Smithkline Beecham Corporation | Compounds and methods for the treatment of neoplastic disease |
| EP1305308B1 (en) * | 2000-07-26 | 2006-12-20 | Smithkline Beecham Plc | Aminopiperidine quinolines and their azaisosteric analogues with antibacterial activity |
| WO2002024684A1 (en) | 2000-09-21 | 2002-03-28 | Smithkline Beecham P.L.C. | Quinoline derivatives as antibacterials |
| FR2816618B1 (fr) | 2000-11-15 | 2002-12-27 | Aventis Pharma Sa | Derives heterocyclylalcoyl piperidine, leur preparation et les compositions qui les contiennent |
| US6603005B2 (en) * | 2000-11-15 | 2003-08-05 | Aventis Pharma S.A. | Heterocyclylalkylpiperidine derivatives, their preparation and compositions containing them |
| GB0031086D0 (en) | 2000-12-20 | 2001-01-31 | Smithkline Beecham Plc | Medicaments |
| GB0031088D0 (en) * | 2000-12-20 | 2001-01-31 | Smithkline Beecham Plc | Medicaments |
| FR2822154B1 (fr) | 2001-03-13 | 2005-10-21 | Aventis Pharma Sa | Derives de la quinolyl propyl piperidine, leur preparation et les compositions qui les contiennent |
| US6602884B2 (en) * | 2001-03-13 | 2003-08-05 | Aventis Pharma S.A. | Quinolylpropylpiperidine derivatives, their preparation, and compositions containing them |
| GB0112834D0 (en) * | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| GB0112836D0 (en) | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| US20030203917A1 (en) * | 2001-07-25 | 2003-10-30 | Smithkline Beecham Corporation And Smithkline Beecham P.L.C. | Compounds and methods for the treatment of neoplastic disease |
| GB0118238D0 (en) | 2001-07-26 | 2001-09-19 | Smithkline Beecham Plc | Medicaments |
-
2001
- 2001-01-22 GB GBGB0101577.5A patent/GB0101577D0/en not_active Ceased
-
2002
- 2002-01-22 EP EP02702296A patent/EP1359908B1/en not_active Expired - Lifetime
- 2002-01-22 AT AT02702296T patent/ATE370731T1/de not_active IP Right Cessation
- 2002-01-22 US US10/466,394 patent/US7205408B2/en not_active Expired - Fee Related
- 2002-01-22 WO PCT/EP2002/000587 patent/WO2002056882A1/en not_active Ceased
- 2002-01-22 JP JP2002557390A patent/JP4472928B2/ja not_active Expired - Lifetime
- 2002-01-22 DE DE60221969T patent/DE60221969T2/de not_active Expired - Lifetime
- 2002-01-22 ES ES02702296T patent/ES2292716T3/es not_active Expired - Lifetime
-
2009
- 2009-11-02 JP JP2009251653A patent/JP2010024246A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2004520360A5 (https=) | ||
| ES2292716T3 (es) | Quinolinas y derivados nitrogenados de las mismas sustituidos en posicion 4 con un resto que contiene piperidina y su uso como agentes antibacterianos. | |
| JP2005525324A5 (https=) | ||
| JP2005504747A5 (https=) | ||
| JP2004534780A5 (https=) | ||
| ES2275006T3 (es) | Derivados heterociclicos biciclicos que contienen nitrogeno para usar como antibacterianos. | |
| JP2006505505A5 (https=) | ||
| JP2005519922A5 (https=) | ||
| JP4445753B2 (ja) | アミノピペリジン誘導体 | |
| DE60215951T2 (de) | Piperidinderivate als antibakterielle mittel | |
| JP2005519981A5 (https=) | ||
| ES2269301T3 (es) | Derivados de piperazina para tratamiento de infecciones bacterianas. | |
| JP4522262B2 (ja) | 化合物 | |
| ES2278778T3 (es) | Aminopiperidin quinolinas y sus analogos azaisostericos con actividad antibacteriana. | |
| US7498326B2 (en) | Compounds | |
| JP2005539087A5 (https=) | ||
| EP0378255B1 (en) | 2-Aminopyrimidinone derivatives | |
| JP2008502689A5 (https=) | ||
| JP2005538125A5 (https=) | ||
| JP2006511622A (ja) | 抗菌剤 | |
| JP2010524884A5 (https=) | ||
| CN1535272A (zh) | 用于抗菌剂的二环含氮杂环 | |
| JP2008505920A5 (https=) | ||
| JPWO2009078481A1 (ja) | 二環性へテロ環誘導体 | |
| KR970001158B1 (ko) | N-(4-피페리디닐) 2환 축합 2-이미다졸아민 유도체 |