JP2002501061A5 - - Google Patents
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- Publication number
- JP2002501061A5 JP2002501061A5 JP2000528558A JP2000528558A JP2002501061A5 JP 2002501061 A5 JP2002501061 A5 JP 2002501061A5 JP 2000528558 A JP2000528558 A JP 2000528558A JP 2000528558 A JP2000528558 A JP 2000528558A JP 2002501061 A5 JP2002501061 A5 JP 2002501061A5
- Authority
- JP
- Japan
- Prior art keywords
- piperidine
- heptyl
- methoxyquinolin
- propyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 21
- -1 amino, piperidyl Chemical group 0.000 description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 17
- 125000003342 alkenyl group Chemical group 0.000 description 12
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 7
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 7
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000005137 alkenylsulfonyl group Chemical group 0.000 description 3
- 150000001540 azides Chemical class 0.000 description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- 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 description 2
- 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 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000005035 acylthio group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 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 description 1
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- CLEPDZYETJYMRM-UHFFFAOYSA-N 2-(1-heptylpiperidin-4-yl)-1-(6-methoxyquinolin-4-yl)ethanol Chemical compound C1CN(CCCCCCC)CCC1CC(O)C1=CC=NC2=CC=C(OC)C=C12 CLEPDZYETJYMRM-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- MCUGWDYYTNIZAC-RSXGOPAZSA-N 2-[(3r,4r)-1-heptyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidin-3-yl]ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 MCUGWDYYTNIZAC-RSXGOPAZSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- LLNBTHNJAWYSNQ-WZKMZYQSSA-N 2-[5-[4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]-1-hydroxypropyl]quinolin-6-yl]oxypentyl]isoindole-1,3-dione Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCC(O)C(C1=C2)=CC=NC1=CC=C2OCCCCCN1C(=O)C2=CC=CC=C2C1=O LLNBTHNJAWYSNQ-WZKMZYQSSA-N 0.000 description 1
- BJZAVWGXACGLSX-IOWSJCHKSA-N 2-[5-[4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propyl]quinolin-6-yl]oxypentyl]isoindole-1,3-dione Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC(C1=C2)=CC=NC1=CC=C2OCCCCCN1C(=O)C2=CC=CC=C2C1=O BJZAVWGXACGLSX-IOWSJCHKSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- CTTNZICAQJZWBS-VWNXMTODSA-N 3-[(3r,4r)-1-heptyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidin-3-yl]propanamide Chemical compound NC(=O)CC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 CTTNZICAQJZWBS-VWNXMTODSA-N 0.000 description 1
- NQCUGVKTWQTSJC-SMWUWQHRSA-N 3-[(3r,4r)-3-ethenyl-1-heptylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-amine Chemical compound C=C[C@H]1CN(CCCCCCC)CC[C@H]1CCC(N)C1=CC=NC2=CC=C(OC)C=C12 NQCUGVKTWQTSJC-SMWUWQHRSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- NSTMVRWATNHOBQ-YXVKNGOVSA-N 4-[(2r,3r)-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-YXVKNGOVSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- YZWUSZOVXNFSJZ-UHFFFAOYSA-N 4-[3-(1-heptylpiperidin-4-yl)propyl]-6-methoxyquinoline Chemical compound C1CN(CCCCCCC)CCC1CCCC1=CC=NC2=CC=C(OC)C=C12 YZWUSZOVXNFSJZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- TWNDOZNMWVTTLB-XZOQPEGZSA-N 4-[3-[(3r,4r)-3-ethenyl-1-heptylpiperidin-4-yl]propyl]-6-methoxyquinoline Chemical compound C=C[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 TWNDOZNMWVTTLB-XZOQPEGZSA-N 0.000 description 1
- OMJURHWAGMIZSW-LOSJGSFVSA-N 4-[3-[(3r,4r)-3-ethyl-1-[(4-ethylphenyl)methyl]piperidin-4-yl]propyl]-6-methoxyquinoline Chemical compound C([C@@H]([C@@H](CC1)CCCC=2C3=CC(OC)=CC=C3N=CC=2)CC)N1CC1=CC=C(CC)C=C1 OMJURHWAGMIZSW-LOSJGSFVSA-N 0.000 description 1
- UNFZAXNIOVMCKD-IEDSLXKASA-N 4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]-1-hydroxypropyl]quinolin-6-ol Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCC(O)C1=CC=NC2=CC=C(O)C=C12 UNFZAXNIOVMCKD-IEDSLXKASA-N 0.000 description 1
- 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 description 1
- NKOYNZFOVUKUMY-XZOQPEGZSA-N 4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propyl]-6-methoxyquinoline Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 NKOYNZFOVUKUMY-XZOQPEGZSA-N 0.000 description 1
- YOUAPNABWNMSDF-LOSJGSFVSA-N 4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propyl]-6-propoxyquinoline Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OCCC)C=C12 YOUAPNABWNMSDF-LOSJGSFVSA-N 0.000 description 1
- OSBYHPROZMZLBS-FCHUYYIVSA-N 4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propyl]quinolin-6-ol Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(O)C=C12 OSBYHPROZMZLBS-FCHUYYIVSA-N 0.000 description 1
- TWNDOZNMWVTTLB-DHIUTWEWSA-N 4-[3-[(3s,4r)-3-ethenyl-1-heptylpiperidin-4-yl]propyl]-6-methoxyquinoline Chemical compound C=C[C@@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 TWNDOZNMWVTTLB-DHIUTWEWSA-N 0.000 description 1
- HHBAYVJDZPKXOM-QZXCJWAESA-N 4-[3-[(3z,4r)-3-ethylidene-1-heptylpiperidin-4-yl]propyl]-6-methoxyquinoline Chemical compound C/C=C/1CN(CCCCCCC)CC[C@H]\1CCCC1=CC=NC2=CC=C(OC)C=C12 HHBAYVJDZPKXOM-QZXCJWAESA-N 0.000 description 1
- 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 description 1
- NDWDVDKLTKOBNE-IZZNHLLZSA-N 4-[4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propyl]quinolin-6-yl]oxybutan-1-amine Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OCCCCN)C=C12 NDWDVDKLTKOBNE-IZZNHLLZSA-N 0.000 description 1
- JVPWTRFRXSTJBV-VXKWHMMOSA-N 4-[[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]methylsulfanylmethyl]-6-methoxyquinoline Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CSCC1=CC=NC2=CC=C(OC)C=C12 JVPWTRFRXSTJBV-VXKWHMMOSA-N 0.000 description 1
- MHBAAZDMDVEJCF-RRPNLBNLSA-N 5-[4-[3-[(3r,4r)-3-ethyl-1-heptylpiperidin-4-yl]propyl]quinolin-6-yl]oxypentan-1-amine Chemical compound CC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OCCCCCN)C=C12 MHBAAZDMDVEJCF-RRPNLBNLSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- SMSKYSIBSAPCKG-SYDXZMBCSA-N N-[4-[3-[(3R,4R)-3-ethyl-1-heptylpiperidin-4-yl]-1-hydroxypropyl]quinolin-6-yl]-2-hydroxy-2-methylpropanamide Chemical compound C(C)[C@H]1CN(CC[C@H]1CCC(C1=CC=NC2=CC=C(C=C12)NC(C(C)(C)O)=O)O)CCCCCCC SMSKYSIBSAPCKG-SYDXZMBCSA-N 0.000 description 1
- XLLKSQQUSXSKIU-FYYLOGMGSA-N [(3r,4r)-1-heptyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidin-3-yl]methanol Chemical compound OC[C@H]1CN(CCCCCCC)CC[C@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 XLLKSQQUSXSKIU-FYYLOGMGSA-N 0.000 description 1
- UZPUDUHOISZXOQ-JTHBVZDNSA-N [(3r,4s)-1-heptyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidin-3-yl]methyl carbamate Chemical compound NC(=O)OC[C@H]1CN(CCCCCCC)CC[C@@H]1CCCC1=CC=NC2=CC=C(OC)C=C12 UZPUDUHOISZXOQ-JTHBVZDNSA-N 0.000 description 1
- PGJANJHHABZLDH-QNWUEUMSSA-N [3-[(3r,4r)-3-ethenyl-1-heptylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propyl]urea Chemical compound C=C[C@H]1CN(CCCCCCC)CC[C@H]1CCC(NC(N)=O)C1=CC=NC2=CC=C(OC)C=C12 PGJANJHHABZLDH-QNWUEUMSSA-N 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005360 alkyl sulfoxide group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000005361 aryl sulfoxide group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 1
- 125000004468 heterocyclylthio group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- INXYGYDFRWCCMF-XZOQPEGZSA-N n-[2-[(3r,4s)-3-ethenyl-1-heptylpiperidin-4-yl]ethyl]-6-methoxy-n-methylquinolin-4-amine Chemical compound C=C[C@H]1CN(CCCCCCC)CC[C@H]1CCN(C)C1=CC=NC2=CC=C(OC)C=C12 INXYGYDFRWCCMF-XZOQPEGZSA-N 0.000 description 1
- UOCHGRZSCFALNO-SFTDATJTSA-N n-[[(3r,4r)-3-ethenyl-1-heptylpiperidin-4-yl]methyl]-6-methoxyquinoline-4-carboxamide Chemical compound C=C[C@H]1CN(CCCCCCC)CC[C@H]1CNC(=O)C1=CC=NC2=CC=C(OC)C=C12 UOCHGRZSCFALNO-SFTDATJTSA-N 0.000 description 1
- 239000008194 pharmaceutical composition 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9801630.6A GB9801630D0 (en) | 1998-01-26 | 1998-01-26 | Novel compounds |
| GB9801630.6 | 1998-09-29 | ||
| GB9821072.7 | 1998-09-29 | ||
| GBGB9821072.7A GB9821072D0 (en) | 1998-09-29 | 1998-09-29 | Medicaments |
| PCT/EP1999/000333 WO1999037635A1 (en) | 1998-01-26 | 1999-01-21 | Quinoline derivatives as antibacterials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002501061A JP2002501061A (ja) | 2002-01-15 |
| JP2002501061A5 true JP2002501061A5 (enExample) | 2006-01-19 |
Family
ID=26313018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000528558A Pending JP2002501061A (ja) | 1998-01-26 | 1999-01-21 | 抗菌剤用キノリン誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1051413B1 (enExample) |
| JP (1) | JP2002501061A (enExample) |
| AR (1) | AR018042A1 (enExample) |
| AU (1) | AU2717899A (enExample) |
| CA (1) | CA2318842A1 (enExample) |
| DE (1) | DE69908555T2 (enExample) |
| ES (1) | ES2201674T3 (enExample) |
| WO (1) | WO1999037635A1 (enExample) |
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 |
| 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 |
| GB9917408D0 (en) | 1999-07-23 | 1999-09-22 | Smithkline Beecham Plc | Compounds |
| GB9917406D0 (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 |
| 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 |
| 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 |
| 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 |
| GB0112834D0 (en) | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| GB0112836D0 (en) | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| AU2003239302A1 (en) * | 2002-01-29 | 2003-09-02 | Glaxo Group Limited | Aminopiperidine compounds, process for their preparation, and pharmaceutical compositions containing them |
| EP1470125A1 (en) | 2002-01-29 | 2004-10-27 | Glaxo Group Limited | Aminopiperidine derivatives |
| 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 |
| TW200409637A (en) | 2002-06-26 | 2004-06-16 | Glaxo Group Ltd | Compounds |
| 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 |
| GB0217294D0 (en) * | 2002-07-25 | 2002-09-04 | Glaxo Group Ltd | Medicaments |
| NZ538391A (en) * | 2002-07-25 | 2005-10-28 | Janssen Pharmaceutica Nv | Quinoline derivatives and their use as mycobacterial inhibitors |
| 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. |
| US7491714B2 (en) | 2002-12-04 | 2009-02-17 | Glaxo Group Limited | Quinolines and nitrogenated derivatives thereof and their use as antibacterial agents |
| CN1795177A (zh) * | 2003-03-28 | 2006-06-28 | 辉瑞产品公司 | 作为治疗动脉粥样硬化和肥胖症的cetp抑制剂的 1 , 2 , 4 , －取代的1，2，3，4，－四氢－和1，2二氢－喹啉以及1， 2 , 3 ， 4－四氢－喹喔啉衍生物 |
| JP2007501854A (ja) * | 2003-05-27 | 2007-02-01 | ファイザー・プロダクツ・インク | 受容体型チロシンキナーゼ阻害薬としてのキナゾリン類およびピリド［３，４−ｄ］ピリミジン類 |
| 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 |
| AU2005210036B2 (en) * | 2004-01-29 | 2010-12-23 | Janssen Pharmaceutica N.V. | Quinoline derivatives for use as mycobacterial inhibitors |
| WO2006081178A2 (en) * | 2005-01-25 | 2006-08-03 | Glaxo Group Limited | Antibacterial agents |
| US7709472B2 (en) | 2005-01-25 | 2010-05-04 | Glaxo Group Limited | Antibacterial agents |
| JP2008528604A (ja) | 2005-01-25 | 2008-07-31 | グラクソ グループ リミテッド | 抗菌剤 |
| US7592334B2 (en) | 2005-01-25 | 2009-09-22 | Glaxo Group Limited | Antibacterial agents |
| WO2006081264A1 (en) | 2005-01-25 | 2006-08-03 | Glaxo Group Limited | Antibacterial agents |
| 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 |
| ES2376488T3 (es) | 2006-01-26 | 2012-03-14 | Actelion Pharmaceuticals Ltd. | Antibióticos de tetrahidropirano. |
| JP2009532504A (ja) | 2006-04-06 | 2009-09-10 | グラクソ グループ リミテッド | 抗菌薬 |
| EP2085383A4 (en) * | 2006-11-16 | 2010-09-22 | Astellas Pharma Inc | Piperidin derivatives or salts thereof |
| MX2009012117A (es) | 2007-05-09 | 2009-11-23 | Pfizer | Composiciones y derivados heterociclicos sustituidos y su uso farmaceutico como antibacterianos. |
| WO2016008381A1 (zh) * | 2014-07-14 | 2016-01-21 | 辰欣药业股份有限公司 | 吡啶衍生物及其作为抗分支杆菌的应用 |
| 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 WO PCT/EP1999/000333 patent/WO1999037635A1/en not_active Ceased
- 1999-01-21 AU AU27178/99A patent/AU2717899A/en not_active Abandoned
- 1999-01-21 ES ES99907388T patent/ES2201674T3/es not_active Expired - Lifetime
- 1999-01-21 DE DE69908555T patent/DE69908555T2/de not_active Expired - Fee Related
- 1999-01-21 EP EP99907388A patent/EP1051413B1/en not_active Expired - Lifetime
- 1999-01-21 JP JP2000528558A patent/JP2002501061A/ja active Pending
- 1999-01-21 CA CA002318842A patent/CA2318842A1/en not_active Abandoned
- 1999-01-26 AR ARP990100304A patent/AR018042A1/es unknown
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