AU2010223513B2 - Substituted 2-mercaptoquinoline-3-carboxamides as KCNQ2/3 modulators - Google Patents

Info

Publication number

AU2010223513B2

AU2010223513B2 AU2010223513A AU2010223513A AU2010223513B2 AU 2010223513 B2 AU2010223513 B2 AU 2010223513B2 AU 2010223513 A AU2010223513 A AU 2010223513A AU 2010223513 A AU2010223513 A AU 2010223513A AU 2010223513 B2 AU2010223513 B2 AU 2010223513B2

Authority

AU

Australia

Prior art keywords

alkyl

methyl

carboxamide

quinoline

unsubstituted

Prior art date

2009-03-12

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Links

• Espacenet
• Global Dossier
• Discuss

• CKWKREFECQVBBZ-UHFFFAOYSA-N 2-sulfanylidene-1h-quinoline-3-carboxamide Chemical class C1=CC=C2N=C(S)C(C(=O)N)=CC2=C1 CKWKREFECQVBBZ-UHFFFAOYSA-N 0.000 title claims abstract description 16
• 108010006746 KCNQ2 Potassium Channel Proteins 0.000 title description 19
• 102000005453 KCNQ2 Potassium Channel Human genes 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 53
• 238000000034 method Methods 0.000 claims abstract description 28
• 239000003814 drug Substances 0.000 claims abstract description 27
• 125000000217 alkyl group Chemical group 0.000 claims description 572
• 125000001424 substituent group Chemical group 0.000 claims description 183
• BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 claims description 143
• 229920006395 saturated elastomer Polymers 0.000 claims description 142
• -1 4-methylpiperazinyl Chemical group 0.000 claims description 106
• 150000003857 carboxamides Chemical class 0.000 claims description 102
• 125000000623 heterocyclic group Chemical group 0.000 claims description 100
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 98
• 125000003118 aryl group Chemical group 0.000 claims description 84
• 125000001072 heteroaryl group Chemical group 0.000 claims description 79
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 70
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 58
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 51
• 125000004076 pyridyl group Chemical group 0.000 claims description 51
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 50
• 239000000203 mixture Substances 0.000 claims description 47
• 125000001544 thienyl group Chemical group 0.000 claims description 45
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 41
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 40
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 36
• 208000002193 Pain Diseases 0.000 claims description 34
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 28
• 239000000126 substance Substances 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 27
• 229910052799 carbon Inorganic materials 0.000 claims description 26
• 230000036407 pain Effects 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 20
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 14
• 206010046543 Urinary incontinence Diseases 0.000 claims description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• 238000002360 preparation method Methods 0.000 claims description 13
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• FIKGWBYHTKYKJN-UHFFFAOYSA-N 2-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C1=CC=C2N=C(C(F)(F)F)C(C(=O)N)=CC2=C1 FIKGWBYHTKYKJN-UHFFFAOYSA-N 0.000 claims description 12
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 12
• 206010015037 epilepsy Diseases 0.000 claims description 12
• 125000002757 morpholinyl group Chemical group 0.000 claims description 12
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 238000006467 substitution reaction Methods 0.000 claims description 10
• RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 8
• 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 8
• 208000019901 Anxiety disease Diseases 0.000 claims description 7
• 208000020925 Bipolar disease Diseases 0.000 claims description 7
• 208000012661 Dyskinesia Diseases 0.000 claims description 7
• 206010026749 Mania Diseases 0.000 claims description 7
• 208000019695 Migraine disease Diseases 0.000 claims description 7
• 208000010877 cognitive disease Diseases 0.000 claims description 7
• 206010027599 migraine Diseases 0.000 claims description 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• 208000014094 Dystonic disease Diseases 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 208000010118 dystonia Diseases 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 229910052705 radium Inorganic materials 0.000 claims description 5
• 229910052701 rubidium Inorganic materials 0.000 claims description 5
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
• RBTMWCQEJUGFEI-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C=1C2=CC=CC=C2N=C(SCCS(=O)(=O)C=2C=CC=CC=2)C=1C(=O)NCC1=CC=CS1 RBTMWCQEJUGFEI-UHFFFAOYSA-N 0.000 claims description 4
• YDGBZUQDDHAFFQ-UHFFFAOYSA-N 2-pentylsulfanyl-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound CCCCCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 YDGBZUQDDHAFFQ-UHFFFAOYSA-N 0.000 claims description 4
• 150000007513 acids Chemical class 0.000 claims description 4
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 4
• HJORHBFHJCZBIH-UHFFFAOYSA-N n-benzyl-2-(3-chloro-2-hydroxypropyl)sulfanyl-4-(2,4-dichlorophenyl)quinoline-3-carboxamide Chemical compound C=1C=CC=CC=1CNC(=O)C=1C(SCC(CCl)O)=NC2=CC=CC=C2C=1C1=CC=C(Cl)C=C1Cl HJORHBFHJCZBIH-UHFFFAOYSA-N 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
• QSTRXYDQLKNNRG-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(thiophen-2-ylmethyl)-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C=1C=CSC=1CNC(=O)C1=CC2=CC(C(F)(F)F)=CC=C2N=C1SCCS(=O)(=O)C1=CC=CC=C1 QSTRXYDQLKNNRG-UHFFFAOYSA-N 0.000 claims description 3
• ZTLQZLGRVVKUAU-UHFFFAOYSA-N 2-ethylsulfanyl-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 ZTLQZLGRVVKUAU-UHFFFAOYSA-N 0.000 claims description 3
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 3
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• KGTWXLZUIRMNID-UHFFFAOYSA-N 2-(2-phenylsulfanylethylsulfanyl)-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C=1C2=CC=CC=C2N=C(SCCSC=2C=CC=CC=2)C=1C(=O)NCC1=CC=CS1 KGTWXLZUIRMNID-UHFFFAOYSA-N 0.000 claims description 2
• BRDPCVBAVSHWJG-UHFFFAOYSA-N 2-(3-cyclohexylpropylsulfanyl)-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C=1C2=CC=CC=C2N=C(SCCCC2CCCCC2)C=1C(=O)NCC1=CC=CS1 BRDPCVBAVSHWJG-UHFFFAOYSA-N 0.000 claims description 2
• DCPMSEUNUUZOKE-UHFFFAOYSA-N 2-(3-phenylpropylsulfanyl)-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C=1C2=CC=CC=C2N=C(SCCCC=2C=CC=CC=2)C=1C(=O)NCC1=CC=CS1 DCPMSEUNUUZOKE-UHFFFAOYSA-N 0.000 claims description 2
• LGLZFNXJLHWYLR-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)sulfonylethylsulfanyl]-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)CCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 LGLZFNXJLHWYLR-UHFFFAOYSA-N 0.000 claims description 2
• XNTODQLICDNQKF-UHFFFAOYSA-N 2-[2-(4-methylphenyl)sulfanylethylsulfanyl]-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C1=CC(C)=CC=C1SCCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 XNTODQLICDNQKF-UHFFFAOYSA-N 0.000 claims description 2
• VZFKPENHJUZZDW-UHFFFAOYSA-N 2-[2-(4-methylphenyl)sulfonylethylsulfanyl]-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 VZFKPENHJUZZDW-UHFFFAOYSA-N 0.000 claims description 2
• KNVVYVSPKSXKSE-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(2-cyclohexylethyl)quinoline-3-carboxamide Chemical compound C=1C2=CC=CC=C2N=C(SCCS(=O)(=O)C=2C=CC=CC=2)C=1C(=O)NCCC1CCCCC1 KNVVYVSPKSXKSE-UHFFFAOYSA-N 0.000 claims description 2
• IXAZYBWMTOQTNB-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(3,3-dimethylbutyl)quinoline-3-carboxamide Chemical compound CC(C)(C)CCNC(=O)C1=CC2=CC=CC=C2N=C1SCCS(=O)(=O)C1=CC=CC=C1 IXAZYBWMTOQTNB-UHFFFAOYSA-N 0.000 claims description 2
• ICECDKYGZLCPCK-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(cyclohexylmethyl)quinoline-3-carboxamide Chemical compound C=1C2=CC=CC=C2N=C(SCCS(=O)(=O)C=2C=CC=CC=2)C=1C(=O)NCC1CCCCC1 ICECDKYGZLCPCK-UHFFFAOYSA-N 0.000 claims description 2
• WAUDLZDKCYBPFH-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(thiophen-2-ylmethyl)-5-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C=1C=CSC=1CNC(=O)C=1C=C2C(C(F)(F)F)=CC=CC2=NC=1SCCS(=O)(=O)C1=CC=CC=C1 WAUDLZDKCYBPFH-UHFFFAOYSA-N 0.000 claims description 2
• IDAUDNJJPNYANF-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(thiophen-2-ylmethyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C=1C=CC=CC=1S(=O)(=O)CCSC1=NC2=CC(C(F)(F)F)=CC=C2C=C1C(=O)NCC1=CC=CS1 IDAUDNJJPNYANF-UHFFFAOYSA-N 0.000 claims description 2
• SVTHLGYCZILPPE-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 SVTHLGYCZILPPE-UHFFFAOYSA-N 0.000 claims description 2
• CAMGJASCBPTCFP-UHFFFAOYSA-N 2-[3-(4-methylphenyl)propylsulfanyl]-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C1=CC(C)=CC=C1CCCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 CAMGJASCBPTCFP-UHFFFAOYSA-N 0.000 claims description 2
• INILATDIIGNRRP-UHFFFAOYSA-N 2-ethylsulfanyl-5-fluoro-n-[(4-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=CC(F)=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 INILATDIIGNRRP-UHFFFAOYSA-N 0.000 claims description 2
• KDYVECDQZBNVNN-UHFFFAOYSA-N 2-ethylsulfanyl-6,7-difluoro-n-[(4-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(F)=C(F)C=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 KDYVECDQZBNVNN-UHFFFAOYSA-N 0.000 claims description 2
• NDJCIULEZPSLRB-UHFFFAOYSA-N 2-ethylsulfanyl-8-fluoro-n-[(3-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=C(F)C=CC=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 NDJCIULEZPSLRB-UHFFFAOYSA-N 0.000 claims description 2
• LLQWDECGIBUBSA-UHFFFAOYSA-N 2-ethylsulfanyl-n-(thiophen-2-ylmethyl)-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=C(C(F)(F)F)C=C2C=C1C(=O)NCC1=CC=CS1 LLQWDECGIBUBSA-UHFFFAOYSA-N 0.000 claims description 2
• HWHHEFYPKKESMJ-UHFFFAOYSA-N 2-ethylsulfanyl-n-(thiophen-2-ylmethyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C=C1C(=O)NCC1=CC=CS1 HWHHEFYPKKESMJ-UHFFFAOYSA-N 0.000 claims description 2
• YOWNRDGWKVDGQH-UHFFFAOYSA-N 2-ethylsulfanyl-n-[(3-fluorophenyl)methyl]-8-hydroxy-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=C(O)C=CC=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 YOWNRDGWKVDGQH-UHFFFAOYSA-N 0.000 claims description 2
• SAWIMBMEOKWHTK-UHFFFAOYSA-N 2-ethylsulfanyl-n-[(4-fluorophenyl)methyl]-4-methyl-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=C(C(F)(F)F)C=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 SAWIMBMEOKWHTK-UHFFFAOYSA-N 0.000 claims description 2
• BOQBDAUMFYRBFM-UHFFFAOYSA-N 2-ethylsulfanyl-n-[(4-fluorophenyl)methyl]-4-methyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 BOQBDAUMFYRBFM-UHFFFAOYSA-N 0.000 claims description 2
• MPUAMENIGDRSCH-UHFFFAOYSA-N 2-ethylsulfanyl-n-[(4-fluorophenyl)methyl]-5-methoxy-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=CC(OC)=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 MPUAMENIGDRSCH-UHFFFAOYSA-N 0.000 claims description 2
• ZYTRDNHAJLVSMB-UHFFFAOYSA-N 2-ethylsulfanyl-n-[(4-fluorophenyl)methyl]-6-methoxy-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=C(OC)C=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 ZYTRDNHAJLVSMB-UHFFFAOYSA-N 0.000 claims description 2
• ODOGGYIXTMHZTB-UHFFFAOYSA-N 2-ethylsulfanyl-n-[(4-fluorophenyl)methyl]-8-methoxy-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=C(OC)C=CC=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 ODOGGYIXTMHZTB-UHFFFAOYSA-N 0.000 claims description 2
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
• RGVSETOUKURHPQ-UHFFFAOYSA-N 4-ethyl-2-ethylsulfanyl-n-[(3-fluorophenyl)methyl]-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(CC)=C1C(=O)NCC1=CC=CC(F)=C1 RGVSETOUKURHPQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
• 229910003827 NRaRb Inorganic materials 0.000 claims description 2
• 239000000654 additive Substances 0.000 claims description 2
• 125000006437 ethyl cyclopropyl group Chemical group 0.000 claims description 2
• KSJCXIFGVXTUQS-UHFFFAOYSA-N methyl 3-[3-(thiophen-2-ylmethylcarbamoyl)-6-(trifluoromethyl)quinolin-2-yl]sulfanylpropanoate Chemical compound COC(=O)CCSC1=NC2=CC=C(C(F)(F)F)C=C2C=C1C(=O)NCC1=CC=CS1 KSJCXIFGVXTUQS-UHFFFAOYSA-N 0.000 claims description 2
• NBCYYXBLHMLNDK-UHFFFAOYSA-N methyl 3-[3-(thiophen-2-ylmethylcarbamoyl)quinolin-2-yl]sulfanylpropanoate Chemical compound COC(=O)CCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 NBCYYXBLHMLNDK-UHFFFAOYSA-N 0.000 claims description 2
• 125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 2
• ZVXKQFPIMUKOMT-UHFFFAOYSA-N n-(3,3-dimethylbutyl)-2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound FC(F)(F)C1=CC=C2C(C)=C(C(=O)NCCC(C)(C)C)C(SCC)=NC2=C1 ZVXKQFPIMUKOMT-UHFFFAOYSA-N 0.000 claims description 2
• DREYSSCBZYWDKN-UHFFFAOYSA-N n-(cyclohexylmethyl)-2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1CCCCC1 DREYSSCBZYWDKN-UHFFFAOYSA-N 0.000 claims description 2
• LFPNCEAJPXGNML-UHFFFAOYSA-N n-[(2,4-difluorophenyl)methyl]-2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1F LFPNCEAJPXGNML-UHFFFAOYSA-N 0.000 claims description 2
• JWWSIJYBINTJOV-UHFFFAOYSA-N 2-benzylsulfanyl-n-[(3-fluorophenyl)methyl]-4-methyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C=1C=CC=CC=1CSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 JWWSIJYBINTJOV-UHFFFAOYSA-N 0.000 claims 1
• JEIFVPVLNYRPCS-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)-n-[(3,4,5-trifluorophenyl)methyl]quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC(F)=C(F)C(F)=C1 JEIFVPVLNYRPCS-UHFFFAOYSA-N 0.000 claims 1
• CSFVPXMKBCZQBY-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(3-methylbutyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound FC(F)(F)C1=CC=C2C(C)=C(C(=O)NCCC(C)C)C(SCC)=NC2=C1 CSFVPXMKBCZQBY-UHFFFAOYSA-N 0.000 claims 1
• QWGINHANBPWPEJ-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-pentyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C1=C(C(F)(F)F)C=C2N=C(SCC)C(C(=O)NCCCCC)=C(C)C2=C1 QWGINHANBPWPEJ-UHFFFAOYSA-N 0.000 claims 1
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• FVZVRJDBPYZXNJ-UHFFFAOYSA-N 2-ethylsulfanyl-5-fluoro-n-[(3-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=CC(F)=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 FVZVRJDBPYZXNJ-UHFFFAOYSA-N 0.000 claims 1
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