JP2006515862A - キノリン類およびそれらの窒素化誘導体ならびにそれらの抗菌剤としての使用 - Google Patents
キノリン類およびそれらの窒素化誘導体ならびにそれらの抗菌剤としての使用 Download PDFInfo
- Publication number
- JP2006515862A JP2006515862A JP2004571000A JP2004571000A JP2006515862A JP 2006515862 A JP2006515862 A JP 2006515862A JP 2004571000 A JP2004571000 A JP 2004571000A JP 2004571000 A JP2004571000 A JP 2004571000A JP 2006515862 A JP2006515862 A JP 2006515862A
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- JP
- Japan
- Prior art keywords
- oxo
- methoxy
- oxazolidine
- alkyl
- propyl
- 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.)
- Ceased
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- 239000003242 anti bacterial agent Substances 0.000 title description 5
- 229940111121 antirheumatic drug quinolines Drugs 0.000 title 1
- 150000003248 quinolines Chemical class 0.000 title 1
- 241000124008 Mammalia Species 0.000 claims abstract description 9
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 8
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 8
- -1 amino, piperidyl Chemical group 0.000 claims description 108
- 125000000217 alkyl group Chemical group 0.000 claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 22
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 22
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 10
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- AEAOMQAWGDKZCV-VWLOTQADSA-N (5r)-3-[3-[1h-indol-2-ylmethyl(methyl)amino]propyl]-5-(6-methoxyquinolin-4-yl)-1,3-oxazolidin-2-one Chemical compound C1=CC=C2NC(CN(C)CCCN3C[C@H](OC3=O)C3=CC=NC4=CC=C(C=C43)OC)=CC2=C1 AEAOMQAWGDKZCV-VWLOTQADSA-N 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000005035 acylthio group Chemical group 0.000 claims description 4
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- XIPZURGTTRZAMC-SFHVURJKSA-N n-[3-[(5r)-5-(6-methoxy-1,5-naphthyridin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propyl]-3-oxo-4h-1,4-benzothiazine-6-sulfonamide Chemical compound S1CC(=O)NC2=CC(S(=O)(=O)NCCCN3C[C@H](OC3=O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 XIPZURGTTRZAMC-SFHVURJKSA-N 0.000 claims description 4
- TZCLLMAQSGBIIS-NRFANRHFSA-N n-[3-[(5r)-5-(6-methoxyquinolin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propyl]-3-oxo-4h-1,4-benzothiazine-6-sulfonamide Chemical compound S1CC(=O)NC2=CC(S(=O)(=O)NCCCN3C[C@H](OC3=O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 TZCLLMAQSGBIIS-NRFANRHFSA-N 0.000 claims description 4
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 4
- HYUZXYZZPRBVBQ-PBHICJAKSA-N (5r)-3-[(2r)-2-hydroxy-3-[(3-oxo-4h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]propyl]-5-(6-methoxy-1,5-naphthyridin-4-yl)-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=NC(CNC[C@@H](O)CN3C[C@H](OC3=O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 HYUZXYZZPRBVBQ-PBHICJAKSA-N 0.000 claims description 3
- AQOIKSICNYLNIQ-DEOSSOPVSA-N (5r)-3-[3-(1h-indol-2-ylmethylamino)propyl]-5-(6-methoxyquinolin-4-yl)-1,3-oxazolidin-2-one Chemical compound C1=CC=C2NC(CNCCCN3C[C@H](OC3=O)C3=CC=NC4=CC=C(C=C43)OC)=CC2=C1 AQOIKSICNYLNIQ-DEOSSOPVSA-N 0.000 claims description 3
- JMVHENCOUMSVSV-QFIPXVFZSA-N (5r)-3-[3-(2,1,3-benzothiadiazol-5-ylmethylamino)propyl]-5-(6-methoxyquinolin-4-yl)-1,3-oxazolidin-2-one Chemical compound C1=CC2=NSN=C2C=C1CNCCCN(C(=O)O1)C[C@H]1C1=CC=NC2=CC=C(OC)C=C21 JMVHENCOUMSVSV-QFIPXVFZSA-N 0.000 claims description 3
- CBHCYXSDGUWRPT-NRFANRHFSA-N (5r)-3-[3-[(4-fluoro-1h-benzimidazol-2-yl)methylamino]propyl]-5-(6-methoxyquinolin-4-yl)-1,3-oxazolidin-2-one Chemical compound C1=CC=C2NC(CNCCCN3C[C@H](OC3=O)C3=CC=NC4=CC=C(C=C43)OC)=NC2=C1F CBHCYXSDGUWRPT-NRFANRHFSA-N 0.000 claims description 3
- LUUOFYVQTNURRG-VWLOTQADSA-N (5r)-3-[3-[(8-hydroxyquinolin-2-yl)methyl-methylamino]propyl]-5-(6-methoxyquinolin-4-yl)-1,3-oxazolidin-2-one Chemical compound C1=CC=C(O)C2=NC(CN(C)CCCN3C[C@H](OC3=O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 LUUOFYVQTNURRG-VWLOTQADSA-N 0.000 claims description 3
- WPDCXKPBUWDMJZ-DEOSSOPVSA-N (5r)-3-[3-[(8-hydroxyquinolin-2-yl)methylamino]propyl]-5-(6-methoxyquinolin-4-yl)-1,3-oxazolidin-2-one Chemical compound C1=CC=C(O)C2=NC(CNCCCN3C[C@H](OC3=O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 WPDCXKPBUWDMJZ-DEOSSOPVSA-N 0.000 claims description 3
- JLBIGXJQSKTBPT-UHFFFAOYSA-N 3,6-dimethyl-1,3-benzoxazol-2-one Chemical compound CC1=CC=C2N(C)C(=O)OC2=C1 JLBIGXJQSKTBPT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- UHXYSKUHQCDLJC-IBGZPJMESA-N n-[3-[(5r)-5-(6-methoxy-1,5-naphthyridin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propyl]-3-oxo-4h-1,4-benzoxazine-6-sulfonamide Chemical compound O1CC(=O)NC2=CC(S(=O)(=O)NCCCN3C[C@H](OC3=O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 UHXYSKUHQCDLJC-IBGZPJMESA-N 0.000 claims description 3
- PCMGGFJMXBQOLU-QFIPXVFZSA-N n-[3-[(5r)-5-(6-methoxyquinolin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propyl]-3-oxo-4h-1,4-benzoxazine-6-sulfonamide Chemical compound O1CC(=O)NC2=CC(S(=O)(=O)NCCCN3C[C@H](OC3=O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 PCMGGFJMXBQOLU-QFIPXVFZSA-N 0.000 claims description 3
- CJJGSPROFQEUFV-IBGZPJMESA-N n-[3-[(5r)-5-(6-methoxyquinolin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propyl]-3-oxo-4h-pyrido[3,2-b][1,4]thiazine-6-carboxamide Chemical compound S1CC(=O)NC2=NC(C(=O)NCCCN3C[C@H](OC3=O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 CJJGSPROFQEUFV-IBGZPJMESA-N 0.000 claims description 3
- XIPZURGTTRZAMC-GOSISDBHSA-N n-[3-[(5s)-5-(6-methoxy-1,5-naphthyridin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propyl]-3-oxo-4h-1,4-benzothiazine-6-sulfonamide Chemical compound S1CC(=O)NC2=CC(S(=O)(=O)NCCCN3C[C@@H](OC3=O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 XIPZURGTTRZAMC-GOSISDBHSA-N 0.000 claims description 3
- RAVATXRLPGKJOY-UHFFFAOYSA-N n-[3-[5-(6-methoxy-1,5-naphthyridin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propyl]-2,3-dihydro-1,4-benzodioxine-6-sulfonamide Chemical compound O1CCOC2=CC(S(=O)(=O)NCCCN3CC(OC3=O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 RAVATXRLPGKJOY-UHFFFAOYSA-N 0.000 claims description 3
- UIRSLBDCOYTZPH-UHFFFAOYSA-N 4h-1,4-thiazin-3-one Chemical compound O=C1CSC=CN1 UIRSLBDCOYTZPH-UHFFFAOYSA-N 0.000 claims description 2
- SPALLIDCFHEQEV-UHFFFAOYSA-N 5-(6-methoxy-1,5-naphthyridin-4-yl)-3-[3-[(3-oxo-4h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]propyl]-1,3-oxazolidin-2-one Chemical compound S1CC(=O)NC2=NC(CNCCCN3CC(OC3=O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 SPALLIDCFHEQEV-UHFFFAOYSA-N 0.000 claims description 2
- UPMFSPLIDSVINY-NRFANRHFSA-N 6-[[3-[(5r)-5-(6-methoxyquinolin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propylamino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNCCCN3C[C@H](OC3=O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 UPMFSPLIDSVINY-NRFANRHFSA-N 0.000 claims description 2
- ICGMENBORXRJLF-FQEVSTJZSA-N 6-[[3-[(5r)-5-(8-fluoro-6-methoxyquinolin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propylamino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNCCCN3C[C@H](OC3=O)C3=CC=NC4=C(F)C=C(C=C43)OC)=CC=C21 ICGMENBORXRJLF-FQEVSTJZSA-N 0.000 claims description 2
- AJVKFKOLEHQSPO-UHFFFAOYSA-N 6-[[3-[5-(6-methoxy-1,5-naphthyridin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propylamino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNCCCN3CC(OC3=O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 AJVKFKOLEHQSPO-UHFFFAOYSA-N 0.000 claims description 2
- IIDSPOLGDKEOSC-FQEVSTJZSA-N 7-chloro-n-[3-[(5r)-5-(6-methoxyquinolin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propyl]-3-oxo-4h-1,4-benzothiazine-6-sulfonamide Chemical compound N1C(=O)CSC(C=C2Cl)=C1C=C2S(=O)(=O)NCCCN(C(=O)O1)C[C@H]1C1=CC=NC2=CC=C(OC)C=C21 IIDSPOLGDKEOSC-FQEVSTJZSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005361 aryl sulfoxide group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 2
- AWVYLJPUCRPLPE-UGSOOPFHSA-N n-[(2r)-2-hydroxy-3-[(5r)-5-(6-methoxy-1,5-naphthyridin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propyl]-3-oxo-4h-1,4-benzothiazine-6-sulfonamide Chemical compound S1CC(=O)NC2=CC(S(=O)(=O)NC[C@H](O)CN3C[C@H](OC3=O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 AWVYLJPUCRPLPE-UGSOOPFHSA-N 0.000 claims description 2
- AWVYLJPUCRPLPE-ACJLOTCBSA-N n-[(2s)-2-hydroxy-3-[(5r)-5-(6-methoxy-1,5-naphthyridin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propyl]-3-oxo-4h-1,4-benzothiazine-6-sulfonamide Chemical compound S1CC(=O)NC2=CC(S(=O)(=O)NC[C@@H](O)CN3C[C@H](OC3=O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 AWVYLJPUCRPLPE-ACJLOTCBSA-N 0.000 claims description 2
- POPOHMGVBQBRKI-IBGZPJMESA-N n-[3-[(5r)-5-(6-methoxy-1,5-naphthyridin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]-2,2-dimethylpropyl]-3-oxo-4h-1,4-benzothiazine-6-sulfonamide Chemical compound S1CC(=O)NC2=CC(S(=O)(=O)NCC(C)(C)CN3C[C@H](OC3=O)C3=CC=NC4=CC=C(N=C43)OC)=CC=C21 POPOHMGVBQBRKI-IBGZPJMESA-N 0.000 claims description 2
- BYSDKCNZAZCMBE-QFIPXVFZSA-N n-[3-[(5r)-5-(6-methoxyquinolin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propyl]-4-oxo-3,5-dihydro-2h-1,5-benzothiazepine-7-sulfonamide Chemical compound S1CCC(=O)NC2=CC(S(=O)(=O)NCCCN3C[C@H](OC3=O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 BYSDKCNZAZCMBE-QFIPXVFZSA-N 0.000 claims description 2
- IBPIFONELNHGBT-FQEVSTJZSA-N n-[3-[(5r)-5-(8-fluoro-6-methoxyquinolin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propyl]-3-oxo-4h-1,4-benzothiazine-6-sulfonamide Chemical compound S1CC(=O)NC2=CC(S(=O)(=O)NCCCN3C[C@H](OC3=O)C3=CC=NC4=C(F)C=C(C=C43)OC)=CC=C21 IBPIFONELNHGBT-FQEVSTJZSA-N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract description 4
- 150000005054 naphthyridines Chemical class 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
- 238000005481 NMR spectroscopy Methods 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 47
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 44
- 239000000243 solution Substances 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 239000000741 silica gel Substances 0.000 description 30
- 229910002027 silica gel Inorganic materials 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- 238000003818 flash chromatography Methods 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001414 amino alcohols Chemical class 0.000 description 6
- 239000013058 crude material Substances 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
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- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 1
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- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- PXWXXFMAUZVENI-QHCPKHFHSA-N n-[3-[(5r)-5-(6-methoxyquinolin-4-yl)-2-oxo-1,3-oxazolidin-3-yl]propyl]-3-oxo-4,5-dihydro-1,5-benzothiazepine-7-sulfonamide Chemical compound S1CC(=O)CNC2=CC(S(=O)(=O)NCCCN3C[C@H](OC3=O)C3=CC=NC4=CC=C(C=C43)OC)=CC=C21 PXWXXFMAUZVENI-QHCPKHFHSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- SMPAPEKFGLKOIC-UHFFFAOYSA-N oxolane;hydrochloride Chemical compound Cl.C1CCOC1 SMPAPEKFGLKOIC-UHFFFAOYSA-N 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- POHWAQLZBIMPRN-UHFFFAOYSA-N tert-butyl n-(3-aminopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCN POHWAQLZBIMPRN-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- JJIHENIPUIXQDM-UHFFFAOYSA-N thiadiazole-5-carbaldehyde Chemical compound O=CC1=CN=NS1 JJIHENIPUIXQDM-UHFFFAOYSA-N 0.000 description 1
- NIBOWJNPZQGNKW-UHFFFAOYSA-N thiazepan-5-one Chemical compound O=C1CCNSCC1 NIBOWJNPZQGNKW-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- HBDDRESWUAFAHY-UHFFFAOYSA-N thiomorpholin-3-one Chemical compound O=C1CSCCN1 HBDDRESWUAFAHY-UHFFFAOYSA-N 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43090802P | 2002-12-04 | 2002-12-04 | |
| US46960203P | 2003-05-07 | 2003-05-07 | |
| PCT/US2003/038444 WO2004050036A2 (en) | 2002-12-04 | 2003-12-03 | Quinolines and nitrogenated derivatives thereof and their use as antibacterial agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006515862A true JP2006515862A (ja) | 2006-06-08 |
| JP2006515862A5 JP2006515862A5 (enExample) | 2006-11-30 |
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| JP2004571000A Ceased JP2006515862A (ja) | 2002-12-04 | 2003-12-03 | キノリン類およびそれらの窒素化誘導体ならびにそれらの抗菌剤としての使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7491714B2 (enExample) |
| EP (1) | EP1567520B1 (enExample) |
| JP (1) | JP2006515862A (enExample) |
| AT (1) | ATE411312T1 (enExample) |
| AU (1) | AU2003294565A1 (enExample) |
| DE (1) | DE60324179D1 (enExample) |
| ES (1) | ES2312839T3 (enExample) |
| WO (1) | WO2004050036A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011506593A (ja) * | 2007-12-18 | 2011-03-03 | アクテリオン ファーマシューティカルズ リミテッド | ５−アミノシクリルメチル−オキサゾリジン−２−オン誘導体 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1470125A1 (en) | 2002-01-29 | 2004-10-27 | Glaxo Group Limited | Aminopiperidine derivatives |
| AU2003239302A1 (en) | 2002-01-29 | 2003-09-02 | Glaxo Group Limited | Aminopiperidine compounds, process for their preparation, and pharmaceutical compositions containing them |
| TW200409637A (en) | 2002-06-26 | 2004-06-16 | Glaxo Group Ltd | Compounds |
| AR040335A1 (es) | 2002-06-26 | 2005-03-30 | Glaxo Group Ltd | Compuesto de ciclohexano o ciclohexeno, uso del mismo para preparar un medicamento, composicion farmaceutica que lo comprende, procedimiento y compuestos intermediarios de utilidad para preparar dicho compuesto |
| ES2350977T3 (es) | 2002-11-05 | 2011-01-28 | Glaxo Group Limited | Agentes antibacterianos. |
| DE60331849D1 (de) | 2002-11-05 | 2010-05-06 | Glaxosmithkline Llc | Antibakterielle wirkstoffe |
| 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 . |
| WO2006002047A2 (en) * | 2004-06-15 | 2006-01-05 | Glaxo Group Limited | Antibacterial agents |
| US20070254872A1 (en) * | 2004-07-08 | 2007-11-01 | Glaxo Group Limited | Antibacterial Agents |
| EP1773343A4 (en) * | 2004-07-13 | 2009-05-13 | Glaxo Group Ltd | ANTIBACTERIAL AGENTS |
| CL2008001003A1 (es) * | 2007-04-11 | 2008-10-17 | Actelion Pharmaceuticals Ltd | Compuestos derivados de oxazolidinona; composicion farmaceutica que comprende a dichos compuestos; y su uso para preparar un medicamento para tratar una infeccion bacteriana. |
| CL2008001002A1 (es) * | 2007-04-11 | 2008-10-17 | Actelion Pharmaceuticals Ltd | Compuestos derivados de oxazolidinona; composicion farmaceutica que comprende a dichos compuestos; y su uso para preparar un medicamento para tratar una infeccion bacteriana. |
| JPWO2012108376A1 (ja) | 2011-02-07 | 2014-07-03 | 第一三共株式会社 | アミノ基含有ピロリジノン誘導体 |
| WO2014024056A1 (en) | 2012-08-06 | 2014-02-13 | Daiichi Sankyo Company, Limited | Pyrrolidine derivatives with antibacterial properties |
| CN113735770B (zh) * | 2021-09-30 | 2023-06-06 | 四川大学 | 一种铑催化的4-苯基噁二唑酮与碳酸亚乙烯酯合成1-氨基异喹啉骨架的方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09194478A (ja) * | 1996-01-16 | 1997-07-29 | Bayer Ag | ２−オキソ−および２−チオ−１，２−ジヒドロキノリニル−オキサゾリジノン類 |
| WO2001072723A1 (en) * | 2000-03-28 | 2001-10-04 | Nippon Soda Co.,Ltd. | Oxa(thia)zolidine derivative and anti-inflammatory drug |
| WO2002059116A2 (en) * | 2000-12-21 | 2002-08-01 | Pharmacia & Upjohn Company | Antimicrobial quinolone derivatives and use of the same to treat bacterial infections |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999037635A1 (en) | 1998-01-26 | 1999-07-29 | Smithkline Beecham Plc | 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 |
| AU2437900A (en) | 1999-01-20 | 2000-08-07 | Smithkline Beecham Plc | Piperidinylquinolines as protein tyrosine kinase inhibitors |
| 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 |
| US6403610B1 (en) * | 1999-09-17 | 2002-06-11 | Aventis Pharma S.A. | Quinolylpropylpiperidine derivatives, their preparation and the compositions which comprise them |
| 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 |
| EP1305308B1 (en) | 2000-07-26 | 2006-12-20 | Smithkline Beecham Plc | Aminopiperidine quinolines and their azaisosteric analogues with antibacterial activity |
| ATE327231T1 (de) | 2000-09-21 | 2006-06-15 | Smithkline Beecham Plc | Chinolinderivate als antibakterielle mittel |
| 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 |
| GB0031088D0 (en) | 2000-12-20 | 2001-01-31 | Smithkline Beecham Plc | Medicaments |
| GB0031086D0 (en) | 2000-12-20 | 2001-01-31 | Smithkline Beecham Plc | Medicaments |
| GB0101577D0 (en) | 2001-01-22 | 2001-03-07 | Smithkline Beecham Plc | Compounds |
| GB0112834D0 (en) | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| EP1470125A1 (en) * | 2002-01-29 | 2004-10-27 | Glaxo Group Limited | Aminopiperidine derivatives |
| AU2003239302A1 (en) | 2002-01-29 | 2003-09-02 | Glaxo Group Limited | Aminopiperidine compounds, process for their preparation, and pharmaceutical compositions containing them |
| TW200409637A (en) * | 2002-06-26 | 2004-06-16 | Glaxo Group Ltd | Compounds |
| AR040335A1 (es) | 2002-06-26 | 2005-03-30 | Glaxo Group Ltd | Compuesto de ciclohexano o ciclohexeno, uso del mismo para preparar un medicamento, composicion farmaceutica que lo comprende, procedimiento y compuestos intermediarios de utilidad para preparar dicho compuesto |
| GB0217294D0 (en) * | 2002-07-25 | 2002-09-04 | Glaxo Group Ltd | Medicaments |
| ATE463494T1 (de) * | 2002-10-10 | 2010-04-15 | Morphochem Ag Komb Chemie | Neue verbindungen mit antibakterieller aktivität |
| DE60331849D1 (de) | 2002-11-05 | 2010-05-06 | Glaxosmithkline Llc | Antibakterielle wirkstoffe |
| ES2350977T3 (es) * | 2002-11-05 | 2011-01-28 | Glaxo Group Limited | Agentes antibacterianos. |
| 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 . |
| TW200507841A (en) | 2003-03-27 | 2005-03-01 | Glaxo Group Ltd | Antibacterial agents |
| US7232833B2 (en) * | 2003-03-28 | 2007-06-19 | Novexel | 4-substituted quinoline derivatives, method and intermediates for their preparation and pharmaceutical compositions containing them |
| 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 |
-
2003
- 2003-12-03 US US10/537,034 patent/US7491714B2/en not_active Expired - Fee Related
- 2003-12-03 AT AT03787253T patent/ATE411312T1/de not_active IP Right Cessation
- 2003-12-03 WO PCT/US2003/038444 patent/WO2004050036A2/en not_active Ceased
- 2003-12-03 ES ES03787253T patent/ES2312839T3/es not_active Expired - Lifetime
- 2003-12-03 EP EP03787253A patent/EP1567520B1/en not_active Expired - Lifetime
- 2003-12-03 AU AU2003294565A patent/AU2003294565A1/en not_active Abandoned
- 2003-12-03 DE DE60324179T patent/DE60324179D1/de not_active Expired - Lifetime
- 2003-12-03 JP JP2004571000A patent/JP2006515862A/ja not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09194478A (ja) * | 1996-01-16 | 1997-07-29 | Bayer Ag | ２−オキソ−および２−チオ−１，２−ジヒドロキノリニル−オキサゾリジノン類 |
| WO2001072723A1 (en) * | 2000-03-28 | 2001-10-04 | Nippon Soda Co.,Ltd. | Oxa(thia)zolidine derivative and anti-inflammatory drug |
| WO2002059116A2 (en) * | 2000-12-21 | 2002-08-01 | Pharmacia & Upjohn Company | Antimicrobial quinolone derivatives and use of the same to treat bacterial infections |
| JP2004518677A (ja) * | 2000-12-21 | 2004-06-24 | ファルマシア・アンド・アップジョン・カンパニー | 抗菌性キノロン誘導体および細菌感染を治療するためのその使用 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011506593A (ja) * | 2007-12-18 | 2011-03-03 | アクテリオン ファーマシューティカルズ リミテッド | ５−アミノシクリルメチル−オキサゾリジン−２−オン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2312839T3 (es) | 2009-03-01 |
| AU2003294565A8 (en) | 2004-06-23 |
| WO2004050036A3 (en) | 2004-09-02 |
| EP1567520B1 (en) | 2008-10-15 |
| AU2003294565A1 (en) | 2004-06-23 |
| WO2004050036A2 (en) | 2004-06-17 |
| EP1567520A2 (en) | 2005-08-31 |
| ATE411312T1 (de) | 2008-10-15 |
| EP1567520A4 (en) | 2006-08-02 |
| DE60324179D1 (de) | 2008-11-27 |
| US20060116512A1 (en) | 2006-06-01 |
| US7491714B2 (en) | 2009-02-17 |
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