JP2002501061A - 抗菌剤用キノリン誘導体 - Google Patents
抗菌剤用キノリン誘導体Info
- Publication number
- JP2002501061A JP2002501061A JP2000528558A JP2000528558A JP2002501061A JP 2002501061 A JP2002501061 A JP 2002501061A JP 2000528558 A JP2000528558 A JP 2000528558A JP 2000528558 A JP2000528558 A JP 2000528558A JP 2002501061 A JP2002501061 A JP 2002501061A
- 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
Links
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims description 3
- 239000003242 anti bacterial agent Substances 0.000 title description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 372
- 238000000034 method Methods 0.000 claims abstract description 112
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 241000124008 Mammalia Species 0.000 claims abstract description 11
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 8
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 amino, piperidyl Chemical group 0.000 claims description 130
- 125000000217 alkyl group Chemical group 0.000 claims description 109
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 230000008569 process Effects 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 230000002829 reductive effect Effects 0.000 claims description 22
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 16
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 15
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 150000002367 halogens Chemical class 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
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 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 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
- 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
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000005936 piperidyl group Chemical group 0.000 claims description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 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
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- 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 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
- 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
- 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 claims description 2
- DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000005035 acylthio group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy 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
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 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
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 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 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 1
- 150000002924 oxiranes Chemical class 0.000 claims 1
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 229
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 222
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 168
- 239000000203 mixture Substances 0.000 description 139
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 96
- 239000003921 oil Substances 0.000 description 96
- 235000019198 oils Nutrition 0.000 description 96
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 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
- 239000012264 purified product Substances 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 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
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- 229940032753 sodium iodate Drugs 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
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 241000894007 species Species 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 class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004354 sulfur functional group 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
- 235000002906 tartaric acid Nutrition 0.000 description 1
- ILAGBDRNTTWBTH-QUCCMNQESA-N tert-butyl (3r,4r)-3-(2-hydroxyethyl)-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]1CCO ILAGBDRNTTWBTH-QUCCMNQESA-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
- 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
- ZEXGTLAFLQHAJV-VQTJNVASSA-N tert-butyl n-[2-[(3r,4r)-3-ethenyl-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidin-1-yl]-2-oxoethyl]carbamate Chemical compound C12=CC(OC)=CC=C2N=CC=C1CCC[C@@H]1CCN(C(=O)CNC(=O)OC(C)(C)C)C[C@@H]1C=C ZEXGTLAFLQHAJV-VQTJNVASSA-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
- GCMMHBRAPKXXJF-UHFFFAOYSA-N tert-butyl n-carbamothioyl-n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound CC(C)(C)OC(=O)N(C(N)=S)C(=O)OC(C)(C)C GCMMHBRAPKXXJF-UHFFFAOYSA-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
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 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
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 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
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 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
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 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 |
|---|---|---|---|
| GBGB9801630.6A GB9801630D0 (en) | 1998-01-26 | 1998-01-26 | Novel compounds |
| GB9801630.6 | 1998-01-26 | ||
| 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 true JP2002501061A (ja) | 2002-01-15 |
| JP2002501061A5 JP2002501061A5 (https=) | 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 (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=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006504658A (ja) * | 2002-07-25 | 2006-02-09 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | キノリン誘導体およびミコバクテリア抑制剤としてのそれらの使用 |
| JP2007519687A (ja) * | 2004-01-29 | 2007-07-19 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | マイコバクテリア抑制剤としての使用のためのキノリン誘導体 |
| JP2008528586A (ja) * | 2005-01-25 | 2008-07-31 | グラクソ グループ リミテッド | 抗菌剤 |
Families Citing this family (47)
| 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 |
| 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 |
| 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 |
| 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
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006504658A (ja) * | 2002-07-25 | 2006-02-09 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | キノリン誘導体およびミコバクテリア抑制剤としてのそれらの使用 |
| JP2007519687A (ja) * | 2004-01-29 | 2007-07-19 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | マイコバクテリア抑制剤としての使用のためのキノリン誘導体 |
| JP4919810B2 (ja) * | 2004-01-29 | 2012-04-18 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | マイコバクテリア抑制剤としての使用のためのキノリン誘導体 |
| JP2008528586A (ja) * | 2005-01-25 | 2008-07-31 | グラクソ グループ リミテッド | 抗菌剤 |
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 |
| CA2318842A1 (en) | 1999-07-29 |
| WO1999037635A1 (en) | 1999-07-29 |
| DE69908555T2 (de) | 2004-05-06 |
| EP1051413A1 (en) | 2000-11-15 |
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