DE69908555T2 - Chinolinderivate als antibakterielles arzneimittel - Google Patents
Chinolinderivate als antibakterielles arzneimittel Download PDFInfo
- Publication number
- DE69908555T2 DE69908555T2 DE69908555T DE69908555T DE69908555T2 DE 69908555 T2 DE69908555 T2 DE 69908555T2 DE 69908555 T DE69908555 T DE 69908555T DE 69908555 T DE69908555 T DE 69908555T DE 69908555 T2 DE69908555 T2 DE 69908555T2
- Authority
- DE
- Germany
- Prior art keywords
- piperidine
- heptyl
- propyl
- methoxy
- quinolin
- 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.)
- Expired - Fee Related
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- 230000000844 anti-bacterial effect Effects 0.000 title description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 3
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 262
- -1 amino, piperidyl Chemical group 0.000 claims description 148
- 238000000034 method Methods 0.000 claims description 102
- 125000000217 alkyl group Chemical group 0.000 claims description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 78
- 230000008569 process Effects 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 29
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 19
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 150000002118 epoxides Chemical class 0.000 claims description 6
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
- 208000035143 Bacterial infection Diseases 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- SCNDCEOTFBJOTD-MMZZDGEESA-N 1-[(3r,4r)-1-heptyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidin-3-yl]ethanol Chemical compound CC(O)[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 SCNDCEOTFBJOTD-MMZZDGEESA-N 0.000 claims description 4
- MGPAAHBYOJOVQI-RSXGOPAZSA-N 2-[(3r,4r)-1-heptyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidin-3-yl]ethyl acetate Chemical compound CC(=O)OCC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 MGPAAHBYOJOVQI-RSXGOPAZSA-N 0.000 claims description 4
- 125000005035 acylthio group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- DFHLBJKUZQIJGE-UHFFFAOYSA-N 4-[(1-heptylpiperidin-4-yl)methoxy]-6-methoxyquinoline Chemical compound C1CN(CCCCCCC)CCC1COC1=CC=NC2=CC=C(OC)C=C12 DFHLBJKUZQIJGE-UHFFFAOYSA-N 0.000 claims description 3
- OWPIVGMZBKGNCQ-FCHUYYIVSA-N 4-[2-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]ethyl]-6-methoxyquinoline Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCC1=CC=NC2=CC=C(OC)C=C12 OWPIVGMZBKGNCQ-FCHUYYIVSA-N 0.000 claims description 3
- QUTCTDGMSAMAQN-XZOQPEGZSA-N 4-[3-[(3r,4r)-3-ethenyl-1-(2-phenoxyethyl)piperidin-4-yl]propyl]-6-methoxyquinoline Chemical compound C([C@H]([C@H](C1)C=C)CCCC2=CC=NC3=CC=C(C=C32)OC)CN1CCOC1=CC=CC=C1 QUTCTDGMSAMAQN-XZOQPEGZSA-N 0.000 claims description 3
- ZLLZBIQCMMMRHB-WUFINQPMSA-N 4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propyl]-6-(piperidin-4-ylmethoxy)quinoline Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC(C1=C2)=CC=NC1=CC=C2OCC1CCNCC1 ZLLZBIQCMMMRHB-WUFINQPMSA-N 0.000 claims description 3
- SAXSDOJOUGHKRK-YDUIRMPASA-N 4-[4-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]butan-2-yl]-6-methoxyquinoline Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCC(C)C1=CC=NC2=CC=C(OC)C=C12 SAXSDOJOUGHKRK-YDUIRMPASA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 230000008707 rearrangement Effects 0.000 claims description 3
- MTMVVOSGPKURPD-FIXSFTCYSA-N (2s)-1-[(3r,4s)-3-ethyl-1-heptylpiperidin-4-yl]-3-(6-methoxyquinolin-4-yl)propan-2-ol Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1C[C@H](O)CC1=CC=NC2=CC=C(OC)C=C12 MTMVVOSGPKURPD-FIXSFTCYSA-N 0.000 claims description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- SYQXYPSSIFFSBO-UHFFFAOYSA-N 1-(1-heptylpiperidin-4-yl)-3-(6-methoxyquinolin-4-yl)propan-2-ol Chemical compound C1CN(CCCCCCC)CCC1CC(O)CC1=CC=NC2=CC=C(OC)C=C12 SYQXYPSSIFFSBO-UHFFFAOYSA-N 0.000 claims description 2
- WVTBUPSWLGBABS-IEDSLXKASA-N 1-(6-aminoquinolin-4-yl)-3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propan-1-ol Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCC(O)C1=CC=NC2=CC=C(N)C=C12 WVTBUPSWLGBABS-IEDSLXKASA-N 0.000 claims description 2
- XSFWZXPIJMLEKV-IEDSLXKASA-N 1-(6-azidoquinolin-4-yl)-3-[(3R,4R)-3-ethyl-1-heptylpiperidin-4-yl]propan-1-ol Chemical compound C(C)[C@H]1CN(CC[C@H]1CCC(C1=CC=NC2=CC=C(C=C12)N=[N+]=[N-])O)CCCCCCC XSFWZXPIJMLEKV-IEDSLXKASA-N 0.000 claims description 2
- RCADNRZCMMDLTE-OMQKAAQBSA-N 1-[(3r,4r)-1-heptyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidin-3-yl]propan-2-ol Chemical compound CC(O)C[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 RCADNRZCMMDLTE-OMQKAAQBSA-N 0.000 claims description 2
- UEBNGCLREGPCDZ-ACKJMCFBSA-N 1-[6-(5-aminopentoxy)quinolin-4-yl]-3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propan-1-ol Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCC(O)C1=CC=NC2=CC=C(OCCCCCN)C=C12 UEBNGCLREGPCDZ-ACKJMCFBSA-N 0.000 claims description 2
- NOHZKHZGVCYPTI-UHFFFAOYSA-N 1-heptyl-n-(6-methoxyquinolin-4-yl)piperidine-4-carboxamide Chemical compound C1CN(CCCCCCC)CCC1C(=O)NC1=CC=NC2=CC=C(OC)C=C12 NOHZKHZGVCYPTI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- AFNHEZHAFSXQMB-VWNXMTODSA-N 2-[(3r,4r)-1-heptyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidin-3-yl]ethanol Chemical compound OCC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 AFNHEZHAFSXQMB-VWNXMTODSA-N 0.000 claims description 2
- DGLWHNSPAQNLID-VWNXMTODSA-N 2-[(3r,4r)-1-heptyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidin-3-yl]ethyl carbamate Chemical compound NC(=O)OCC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 DGLWHNSPAQNLID-VWNXMTODSA-N 0.000 claims description 2
- IKQUYBYIZXYCBM-RSXGOPAZSA-N 2-[(3r,4r)-1-heptyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidin-3-yl]ethyl n-ethylcarbamate Chemical compound CCNC(=O)OCC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 IKQUYBYIZXYCBM-RSXGOPAZSA-N 0.000 claims description 2
- WCVPIIKWQGFVKT-IPEYFGQDSA-N 2-[(3r,4s)-3-ethenyl-1-heptylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)ethanol Chemical compound C=C[C@H]1CN(CCCCCCC)CC[C@H]1CC(O)C1=CC=NC2=CC=C(OC)C=C12 WCVPIIKWQGFVKT-IPEYFGQDSA-N 0.000 claims description 2
- FGNWTBNQJHEIEF-LOSJGSFVSA-N 2-[3-[4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propyl]quinolin-6-yl]oxypropyl]guanidine Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OCCCN=C(N)N)C=C12 FGNWTBNQJHEIEF-LOSJGSFVSA-N 0.000 claims description 2
- UUGIVZNWPDJGDF-BJKOFHAPSA-N 2-[4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propyl]quinolin-6-yl]oxyethanamine Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OCCN)C=C12 UUGIVZNWPDJGDF-BJKOFHAPSA-N 0.000 claims description 2
- PLXLUAHBZPUHDR-BJKOFHAPSA-N 2-[4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propyl]quinolin-6-yl]oxyethanol Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OCCO)C=C12 PLXLUAHBZPUHDR-BJKOFHAPSA-N 0.000 claims description 2
- JLOPKNLHBOJOAN-FEMHNBHWSA-N 3-[(3R,4R)-3-ethyl-1-(3-phenylprop-2-enyl)piperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-ol Chemical compound C(C)[C@H]1CN(CC[C@H]1CCC(C1=CC=NC2=CC=C(C=C12)OC)O)CC=CC1=CC=CC=C1 JLOPKNLHBOJOAN-FEMHNBHWSA-N 0.000 claims description 2
- KXTMVVOLTUHORR-BWOOIXMFSA-N 3-[(3r,4r)-1-decyl-3-ethylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-ol Chemical compound CC[C@H]1CN(CCCCCCCCCC)CC[C@H]1CCC(O)C1=CC=NC2=CC=C(OC)C=C12 KXTMVVOLTUHORR-BWOOIXMFSA-N 0.000 claims description 2
- HQMFEJWCGYLQKF-LOSJGSFVSA-N 3-[(3r,4r)-1-decyl-3-ethylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-one Chemical compound CC[C@H]1CN(CCCCCCCCCC)CC[C@H]1CCC(=O)C1=CC=NC2=CC=C(OC)C=C12 HQMFEJWCGYLQKF-LOSJGSFVSA-N 0.000 claims description 2
- JNZZZQCLAKXJTF-YEOOOGFDSA-N 3-[(3r,4r)-1-dodecyl-3-ethylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-ol Chemical compound CC[C@H]1CN(CCCCCCCCCCCC)CC[C@H]1CCC(O)C1=CC=NC2=CC=C(OC)C=C12 JNZZZQCLAKXJTF-YEOOOGFDSA-N 0.000 claims description 2
- PXDPKSBTBVJFLQ-RRPNLBNLSA-N 3-[(3r,4r)-1-dodecyl-3-ethylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-one Chemical compound CC[C@H]1CN(CCCCCCCCCCCC)CC[C@H]1CCC(=O)C1=CC=NC2=CC=C(OC)C=C12 PXDPKSBTBVJFLQ-RRPNLBNLSA-N 0.000 claims description 2
- RMQNNPGEGPCOET-OCTGXNKJSA-N 3-[(3r,4r)-1-heptyl-3-(2-hydroxyethyl)piperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-ol Chemical compound OCC[C@H]1CN(CCCCCCC)CC[C@H]1CCC(O)C1=CC=NC2=CC=C(OC)C=C12 RMQNNPGEGPCOET-OCTGXNKJSA-N 0.000 claims description 2
- UTBHPELDVZYPKL-NOZRDPDXSA-N 3-[(3r,4r)-1-heptyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidin-3-yl]propan-1-ol Chemical compound OCCC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 UTBHPELDVZYPKL-NOZRDPDXSA-N 0.000 claims description 2
- AAHZJSGGQIDHES-QNWUEUMSSA-N 3-[(3r,4r)-3-ethenyl-1-heptylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-ol Chemical compound C=C[C@H]1CN(CCCCCCC)CC[C@H]1CCC(O)C1=CC=NC2=CC=C(OC)C=C12 AAHZJSGGQIDHES-QNWUEUMSSA-N 0.000 claims description 2
- ZYFTYUQUQNEEGK-SYDXZMBCSA-N 3-[(3r,4r)-3-ethyl-1-(2-phenylethyl)piperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-ol Chemical compound C([C@@H]([C@@H](CC1)CCC(O)C=2C3=CC(OC)=CC=C3N=CC=2)CC)N1CCC1=CC=CC=C1 ZYFTYUQUQNEEGK-SYDXZMBCSA-N 0.000 claims description 2
- MBZUZSCPUDFFPZ-FEMHNBHWSA-N 3-[(3r,4r)-3-ethyl-1-(3-phenylpropyl)piperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-ol Chemical compound C([C@@H]([C@@H](CC1)CCC(O)C=2C3=CC(OC)=CC=C3N=CC=2)CC)N1CCCC1=CC=CC=C1 MBZUZSCPUDFFPZ-FEMHNBHWSA-N 0.000 claims description 2
- FCAYEFXDXWWJKZ-SMWUWQHRSA-N 3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-amine Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCC(N)C1=CC=NC2=CC=C(OC)C=C12 FCAYEFXDXWWJKZ-SMWUWQHRSA-N 0.000 claims description 2
- GCXXQAWDVDJDTD-QNWUEUMSSA-N 3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-ol Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCC(O)C1=CC=NC2=CC=C(OC)C=C12 GCXXQAWDVDJDTD-QNWUEUMSSA-N 0.000 claims description 2
- RQSYUMQOOCUXON-FCHUYYIVSA-N 3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-one Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCC(=O)C1=CC=NC2=CC=C(OC)C=C12 RQSYUMQOOCUXON-FCHUYYIVSA-N 0.000 claims description 2
- XIOSYABBIYIWTR-IEDSLXKASA-N 3-[(3r,4r)-3-ethyl-1-hexylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-ol Chemical compound CC[C@H]1CN(CCCCCC)CC[C@H]1CCC(O)C1=CC=NC2=CC=C(OC)C=C12 XIOSYABBIYIWTR-IEDSLXKASA-N 0.000 claims description 2
- XLUQBTFHSJZSAV-LEWJYISDSA-N 3-[(3r,4r)-3-ethyl-1-hexylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-one Chemical compound CC[C@H]1CN(CCCCCC)CC[C@H]1CCC(=O)C1=CC=NC2=CC=C(OC)C=C12 XLUQBTFHSJZSAV-LEWJYISDSA-N 0.000 claims description 2
- WIULLPVKMWXFRE-SYDXZMBCSA-N 3-[(3r,4r)-3-ethyl-1-octylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-ol Chemical compound CC[C@H]1CN(CCCCCCCC)CC[C@H]1CCC(O)C1=CC=NC2=CC=C(OC)C=C12 WIULLPVKMWXFRE-SYDXZMBCSA-N 0.000 claims description 2
- AVVAFHIOFVUREY-XZOQPEGZSA-N 3-[(3r,4r)-3-ethyl-1-octylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-one Chemical compound CC[C@H]1CN(CCCCCCCC)CC[C@H]1CCC(=O)C1=CC=NC2=CC=C(OC)C=C12 AVVAFHIOFVUREY-XZOQPEGZSA-N 0.000 claims description 2
- FQYQJNKDYWBQLD-LOSJGSFVSA-N 3-[4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propyl]quinolin-6-yl]oxypropan-1-amine Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OCCCN)C=C12 FQYQJNKDYWBQLD-LOSJGSFVSA-N 0.000 claims description 2
- NSTMVRWATNHOBQ-YDNHHRFVSA-N 4-[(2s,3s)-3-[[(3r,4s)-3-ethenyl-1-heptylpiperidin-4-yl]methyl]oxiran-2-yl]-6-methoxyquinoline Chemical compound C=C[C@H]1CN(CCCCCCC)CC[C@H]1C[C@H]1[C@H](C=2C3=CC(OC)=CC=C3N=CC=2)O1 NSTMVRWATNHOBQ-YDNHHRFVSA-N 0.000 claims description 2
- BNOLGGLYOFCTDK-SYDXZMBCSA-N 4-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]-2-(6-methoxyquinolin-4-yl)butan-2-ol Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCC(C)(O)C1=CC=NC2=CC=C(OC)C=C12 BNOLGGLYOFCTDK-SYDXZMBCSA-N 0.000 claims description 2
- CQNDIWWWNPBUPJ-QNWUEUMSSA-N 4-[1-azido-3-[(3R,4R)-3-ethenyl-1-heptylpiperidin-4-yl]propyl]-6-methoxyquinoline Chemical compound C(=C)[C@H]1CN(CC[C@H]1CCC(C1=CC=NC2=CC=C(C=C12)OC)N=[N+]=[N-])CCCCCCC CQNDIWWWNPBUPJ-QNWUEUMSSA-N 0.000 claims description 2
- KGPTXDWZFCHYIZ-FCHUYYIVSA-N 4-[2-[(3r,4r)-3-ethenyl-1-heptylpiperidin-4-yl]ethyl]-6-methoxyquinoline Chemical compound C=C[C@H]1CN(CCCCCCC)CC[C@H]1CCC1=CC=NC2=CC=C(OC)C=C12 KGPTXDWZFCHYIZ-FCHUYYIVSA-N 0.000 claims description 2
- OQAJOUSJSWKJMV-VXKWHMMOSA-N 4-[2-[(3r,4s)-3-ethenyl-1-heptylpiperidin-4-yl]ethoxy]-6-methoxyquinoline Chemical compound C=C[C@H]1CN(CCCCCCC)CC[C@H]1CCOC1=CC=NC2=CC=C(OC)C=C12 OQAJOUSJSWKJMV-VXKWHMMOSA-N 0.000 claims description 2
- KGPTXDWZFCHYIZ-FGZHOGPDSA-N 4-[2-[(3s,4r)-3-ethenyl-1-heptylpiperidin-4-yl]ethyl]-6-methoxyquinoline Chemical compound C=C[C@@H]1CN(CCCCCCC)CC[C@H]1CCC1=CC=NC2=CC=C(OC)C=C12 KGPTXDWZFCHYIZ-FGZHOGPDSA-N 0.000 claims description 2
- GMCXHKKOCRFGAG-UHFFFAOYSA-N 4-[3-(1-heptylpiperidin-4-yl)prop-1-enyl]-6-methoxyquinoline Chemical compound C1CN(CCCCCCC)CCC1CC=CC1=CC=NC2=CC=C(OC)C=C12 GMCXHKKOCRFGAG-UHFFFAOYSA-N 0.000 claims description 2
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- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003462 sulfoxides 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
- BXWDGHCIFCFASL-CTNGQTDRSA-N tert-butyl (3r,4r)-3-(2-cyanoethyl)-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidine-1-carboxylate Chemical compound C12=CC(OC)=CC=C2N=CC=C1CCC[C@@H]1CCN(C(=O)OC(C)(C)C)C[C@@H]1CCC#N BXWDGHCIFCFASL-CTNGQTDRSA-N 0.000 description 1
- JZSPBWCDZXBEQO-HOTGVXAUSA-N tert-butyl (3r,4r)-3-ethenyl-4-[(2-trimethylsilylethoxycarbonylamino)methyl]piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](CNC(=O)OCC[Si](C)(C)C)[C@@H](C=C)C1 JZSPBWCDZXBEQO-HOTGVXAUSA-N 0.000 description 1
- BGMGXODQCUITKM-IRXDYDNUSA-N tert-butyl (3r,4r)-3-ethenyl-4-[[(6-methoxyquinoline-4-carbonyl)amino]methyl]piperidine-1-carboxylate Chemical compound C12=CC(OC)=CC=C2N=CC=C1C(=O)NC[C@@H]1CCN(C(=O)OC(C)(C)C)C[C@@H]1C=C BGMGXODQCUITKM-IRXDYDNUSA-N 0.000 description 1
- ZMYMNKYFQVVYPX-QWRGUYRKSA-N tert-butyl (3r,4r)-3-ethyl-4-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC[C@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1CO ZMYMNKYFQVVYPX-QWRGUYRKSA-N 0.000 description 1
- SWLFYLJHEMTSME-ROUUACIJSA-N tert-butyl (3r,4r)-3-ethyl-4-[(6-methoxyquinolin-4-yl)methylsulfanylmethyl]piperidine-1-carboxylate Chemical compound CC[C@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1CSCC1=CC=NC2=CC=C(OC)C=C12 SWLFYLJHEMTSME-ROUUACIJSA-N 0.000 description 1
- PBNBZDWHNRZZGB-STQMWFEESA-N tert-butyl (3r,4r)-4-(acetyloxymethyl)-3-ethylpiperidine-1-carboxylate Chemical compound CC[C@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1COC(C)=O PBNBZDWHNRZZGB-STQMWFEESA-N 0.000 description 1
- KNGOWEHLTMIMCP-QWRGUYRKSA-N tert-butyl (3r,4r)-4-(bromomethyl)-3-ethylpiperidine-1-carboxylate Chemical compound CC[C@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1CBr KNGOWEHLTMIMCP-QWRGUYRKSA-N 0.000 description 1
- ONEFUGJPKIYPSR-RSXGOPAZSA-N tert-butyl (3r,4r)-4-[3-(6-methoxyquinolin-4-yl)propyl]-3-[2-(4-methylphenyl)sulfonyloxyethyl]piperidine-1-carboxylate Chemical compound C([C@H]1CN(CC[C@H]1CCCC1=CC=NC2=CC=C(C=C21)OC)C(=O)OC(C)(C)C)COS(=O)(=O)C1=CC=C(C)C=C1 ONEFUGJPKIYPSR-RSXGOPAZSA-N 0.000 description 1
- DSVLZTRRVVHYMB-IZZNHLLZSA-N tert-butyl 2-[4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propyl]quinolin-6-yl]oxyacetate Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OCC(=O)OC(C)(C)C)C=C12 DSVLZTRRVVHYMB-IZZNHLLZSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- RUDXNALMPUXCJY-UHFFFAOYSA-N tert-butyl N-carbamoyl-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound C(C)(C)(C)OC(=O)N(C(=O)N)C(=O)OC(C)(C)C RUDXNALMPUXCJY-UHFFFAOYSA-N 0.000 description 1
- PRJVMUFHASYVLZ-UHFFFAOYSA-N tert-butyl [4-(2-hydroxyethyl)piperidin-1-yl] carbonate Chemical compound CC(C)(C)OC(=O)ON1CCC(CCO)CC1 PRJVMUFHASYVLZ-UHFFFAOYSA-N 0.000 description 1
- SJZZAAUAHSUVFW-LEWJYISDSA-N tert-butyl n-[2-[(3r,4r)-3-ethenyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidin-1-yl]ethyl]carbamate Chemical compound C12=CC(OC)=CC=C2N=CC=C1CCC[C@@H]1CCN(CCNC(=O)OC(C)(C)C)C[C@@H]1C=C SJZZAAUAHSUVFW-LEWJYISDSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 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
- PGAJYUDRKAPMPA-UHFFFAOYSA-N trimethylsilyl n-ethylcarbamate Chemical compound CCNC(=O)O[Si](C)(C)C PGAJYUDRKAPMPA-UHFFFAOYSA-N 0.000 description 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
- XFXANHWIBFMEOY-JKSUJKDBSA-N viqualine Chemical compound C12=CC(OC)=CC=C2N=CC=C1CCC[C@@H]1CCNC[C@@H]1C=C XFXANHWIBFMEOY-JKSUJKDBSA-N 0.000 description 1
- DKRSEIPLAZTSFD-LSDHHAIUSA-N viquidil Chemical compound C12=CC(OC)=CC=C2N=CC=C1C(=O)CC[C@@H]1CCNC[C@@H]1C=C DKRSEIPLAZTSFD-LSDHHAIUSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9801630 | 1998-01-26 | ||
| GBGB9801630.6A GB9801630D0 (en) | 1998-01-26 | 1998-01-26 | Novel compounds |
| GBGB9821072.7A GB9821072D0 (en) | 1998-09-29 | 1998-09-29 | Medicaments |
| GB9821072 | 1998-09-29 | ||
| PCT/EP1999/000333 WO1999037635A1 (en) | 1998-01-26 | 1999-01-21 | Quinoline derivatives as antibacterials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69908555D1 DE69908555D1 (de) | 2003-07-10 |
| DE69908555T2 true DE69908555T2 (de) | 2004-05-06 |
Family
ID=26313018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69908555T Expired - Fee Related DE69908555T2 (de) | 1998-01-26 | 1999-01-21 | Chinolinderivate als antibakterielles arzneimittel |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1051413B1 (https=) |
| JP (1) | JP2002501061A (https=) |
| AR (1) | AR018042A1 (https=) |
| AU (1) | AU2717899A (https=) |
| CA (1) | CA2318842A1 (https=) |
| DE (1) | DE69908555T2 (https=) |
| ES (1) | ES2201674T3 (https=) |
| WO (1) | WO1999037635A1 (https=) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| US6603005B2 (en) | 2000-11-15 | 2003-08-05 | Aventis Pharma S.A. | Heterocyclylalkylpiperidine derivatives, their preparation and compositions containing them |
| FR2816618B1 (fr) * | 2000-11-15 | 2002-12-27 | Aventis Pharma Sa | Derives heterocyclylalcoyl piperidine, leur preparation et les compositions qui les contiennent |
| GB0031086D0 (en) * | 2000-12-20 | 2001-01-31 | Smithkline Beecham Plc | Medicaments |
| GB0031088D0 (en) * | 2000-12-20 | 2001-01-31 | Smithkline Beecham Plc | Medicaments |
| GB0101577D0 (en) | 2001-01-22 | 2001-03-07 | Smithkline Beecham Plc | Compounds |
| 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 |
| GB0112836D0 (en) | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| GB0112834D0 (en) | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| US7312212B2 (en) | 2002-01-29 | 2007-12-25 | Glaxo Group Limited | Aminopiperidine derivatives |
| EP1470131A2 (en) | 2002-01-29 | 2004-10-27 | Glaxo Group Limited | Aminopiperidine compounds, process for their preparation, and pharmaceutical compositions containing them |
| TW200406413A (en) | 2002-06-26 | 2004-05-01 | 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 |
| FR2842807A1 (fr) * | 2002-07-23 | 2004-01-30 | Aventis Pharma Sa | Derives de la quinolyl propyl piperidine, procede et intermediaires de preparation et compositions les renfermant |
| DK1527050T3 (da) * | 2002-07-25 | 2010-07-19 | Janssen Pharmaceutica Nv | Quinolin-derivater og deres anvendelse som mycobakterielle inhibitorer |
| 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 |
| 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 |
| JP2006521344A (ja) * | 2003-03-28 | 2006-09-21 | ファイザー・プロダクツ・インク | アテローム性動脈硬化症および肥満の治療のためのｃｅｔｐ阻害剤としての１，２，４−置換１，２，３，４−テトラヒドロ−および１，２−ジヒドロ−キノリンおよび１，２，３，４−テトラヒドロ−キノキサリン誘導体 |
| BRPI0410720A (pt) * | 2003-05-27 | 2006-06-20 | Pfizer Prod Inc | quinazolinas e pirido[3,4-d]pirimidinas como inibidores do receptor de tirosina cinase |
| US7348434B2 (en) | 2003-08-08 | 2008-03-25 | Antony Bigot | 4-substituted quinoline derivatives, method and intermediates for their preparation and pharmaceutical compositions containing them |
| FR2858619B1 (fr) * | 2003-08-08 | 2006-12-22 | Aventis Pharma Sa | Derives de quinoleines-4-substituees, leurs procede et intermediaires de preparation et les compositions pharmaceutiques qui les contiennent |
| EA011572B9 (ru) * | 2004-01-29 | 2018-01-31 | Янссен Фармацевтика Н.В. | Производные хинолина для применения в качестве микобактериальных ингибиторов |
| WO2006081182A2 (en) | 2005-01-25 | 2006-08-03 | Glaxo Group Limited | Antibacterial agents |
| 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 |
| JP2008528586A (ja) * | 2005-01-25 | 2008-07-31 | グラクソ グループ リミテッド | 抗菌剤 |
| CA2528849C (en) | 2005-06-08 | 2014-01-14 | Janssen Pharmaceutica N.V. | Quinoline derivatives as antibacterial agents |
| EA010601B1 (ru) * | 2005-06-09 | 2008-10-30 | Янссен Фармацевтика Н.В. | Производные хинолина в качестве антибактериальных агентов |
| ATE536351T1 (de) | 2006-01-26 | 2011-12-15 | Actelion Pharmaceuticals Ltd | Tetrahydropyran-antibiotika |
| WO2007118130A2 (en) | 2006-04-06 | 2007-10-18 | Glaxo Group Limited | Antibacterial agents |
| WO2008059854A1 (en) * | 2006-11-16 | 2008-05-22 | Astellas Pharma Inc. | Piperidine derivatives or salts thereof |
| CN101679357A (zh) | 2007-05-09 | 2010-03-24 | 辉瑞大药厂 | 取代的杂环衍生物及其组合物和作为抗菌剂的药物用途 |
| JP6362235B2 (ja) * | 2014-07-14 | 2018-07-25 | ツーセン ファーマシューティカル カンパニー リミテッド | ピリジン誘導体およびその抗マイコバクテリウムにおける使用 |
| US10301254B2 (en) | 2015-04-23 | 2019-05-28 | Temple University—Of the Commonwealth System of Higher Education | Substituted polycationic multi-quaternary ammonium salts as antimicrobial agents |
| US11111216B2 (en) | 2016-10-26 | 2021-09-07 | Temple University-Of The Commonwealth System Of Higher Education | Polycationic amphiphiles as antimicrobial agents and methods using same |
| WO2020169593A1 (en) | 2019-02-19 | 2020-08-27 | Univerza V Ljubljani | Antibacterials based on monocyclic fragments coupled to aminopiperidine naphthyridine scaffold |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3362875A (en) * | 1965-06-04 | 1968-01-09 | Richardson Merrell Inc | N4, n4'-decamethylene-bis(4-amino)-quinaldine diacetate compositions for controllingtopical infections |
| FR2177511A1 (en) * | 1972-03-28 | 1973-11-09 | Omnium Chimique Sa | Quinolyl pipiridylethyl ketones - with vasodilatory and antispasmodic activity |
| GB1496371A (en) * | 1975-08-18 | 1977-12-30 | Serdex | 4-amino-quinoline derivatives process for their preparation and therapeutic applications thereof |
| NL7908031A (nl) * | 1979-11-01 | 1981-06-01 | Acf Chemiefarma Nv | Nieuwe chinolinederivaten en farmaceutische preparaten die een dergelijke verbinding bevatten, alsmede werk- wijze voor het bereiden van deze verbindingen. |
-
1999
- 1999-01-21 CA CA002318842A patent/CA2318842A1/en not_active Abandoned
- 1999-01-21 JP JP2000528558A patent/JP2002501061A/ja active Pending
- 1999-01-21 AU AU27178/99A patent/AU2717899A/en not_active Abandoned
- 1999-01-21 EP EP99907388A patent/EP1051413B1/en not_active Expired - Lifetime
- 1999-01-21 DE DE69908555T patent/DE69908555T2/de not_active Expired - Fee Related
- 1999-01-21 ES ES99907388T patent/ES2201674T3/es not_active Expired - Lifetime
- 1999-01-21 WO PCT/EP1999/000333 patent/WO1999037635A1/en not_active Ceased
- 1999-01-26 AR ARP990100304A patent/AR018042A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2717899A (en) | 1999-08-09 |
| EP1051413B1 (en) | 2003-06-04 |
| DE69908555D1 (de) | 2003-07-10 |
| ES2201674T3 (es) | 2004-03-16 |
| AR018042A1 (es) | 2001-10-31 |
| JP2002501061A (ja) | 2002-01-15 |
| CA2318842A1 (en) | 1999-07-29 |
| WO1999037635A1 (en) | 1999-07-29 |
| EP1051413A1 (en) | 2000-11-15 |
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