CA2318842A1 - Quinoline derivatives as antibacterials - Google Patents

Info

Publication number

CA2318842A1

CA2318842A1 CA002318842A CA2318842A CA2318842A1 CA 2318842 A1 CA2318842 A1 CA 2318842A1 CA 002318842 A CA002318842 A CA 002318842A CA 2318842 A CA2318842 A CA 2318842A CA 2318842 A1 CA2318842 A1 CA 2318842A1

Authority

CA

Canada

Prior art keywords

piperidine

methoxyquinolin

heptyl

propyl

alkyl

Prior art date

1998-01-26

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 230000000844 anti-bacterial effect Effects 0.000 title description 3
• 229940088710 antibiotic agent Drugs 0.000 title description 3
• 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
• 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 111
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
• 241000124008 Mammalia Species 0.000 claims abstract description 11
• 229910020008 S(O) Inorganic materials 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
• 150000003248 quinolines Chemical class 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 7
• 150000001875 compounds Chemical class 0.000 claims description 275
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 196
• -1 amino, piperidyl Chemical group 0.000 claims description 81
• 229910052739 hydrogen Inorganic materials 0.000 claims description 80
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 77
• 125000000217 alkyl group Chemical group 0.000 claims description 75
• 230000008569 process Effects 0.000 claims description 39
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
• 125000003342 alkenyl group Chemical group 0.000 claims description 22
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 18
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 17
• 125000003277 amino group Chemical group 0.000 claims description 16
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 12
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 12
• 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 11
• 125000004414 alkyl thio group Chemical group 0.000 claims description 10
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
• 125000002252 acyl group Chemical group 0.000 claims description 9
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 9
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 9
• 125000001424 substituent group Chemical group 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 125000004423 acyloxy group Chemical group 0.000 claims description 5
• 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
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
• 125000005035 acylthio group Chemical group 0.000 claims description 4
• 229910052796 boron Inorganic materials 0.000 claims description 4
• 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 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
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 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 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
• 125000003282 alkyl amino group Chemical group 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
• 125000004435 hydrogen atom Chemical group [H]* 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
• 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
• 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
• 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
• 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
• 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
• 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 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
• 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
• 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
• 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
• 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
• 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
• 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 description 2
• 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 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
• 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 claims description 2
• 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 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
• 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
• 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 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
• 125000004442 acylamino group Chemical group 0.000 claims description 2
• 125000004391 aryl sulfonyl 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
• 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 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
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 2
• 229940080818 propionamide Drugs 0.000 claims description 2
• 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 claims description 2
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
• 229910052720 vanadium Inorganic materials 0.000 claims description 2
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-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
• 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 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 1
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