TWI461197B - 2-mercaptoquinoline-3-carboxamide as a KCNQ2 / 3 modifier - Google Patents

Info

Publication number

TWI461197B

TWI461197B TW099105238A TW99105238A TWI461197B TW I461197 B TWI461197 B TW I461197B TW 099105238 A TW099105238 A TW 099105238A TW 99105238 A TW99105238 A TW 99105238A TW I461197 B TWI461197 B TW I461197B

Authority

TW

Taiwan

Prior art keywords

group

alkyl

substituted

carbon atoms

methyl

Prior art date

2009-03-12

Links

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• CKWKREFECQVBBZ-UHFFFAOYSA-N 2-sulfanylidene-1h-quinoline-3-carboxamide Chemical compound C1=CC=C2N=C(S)C(C(=O)N)=CC2=C1 CKWKREFECQVBBZ-UHFFFAOYSA-N 0.000 title claims description 18
• 108010006746 KCNQ2 Potassium Channel Proteins 0.000 title description 16
• 102000005453 KCNQ2 Potassium Channel Human genes 0.000 title description 16
• 239000003607 modifier Substances 0.000 title 1
• 125000004432 carbon atom Chemical group C* 0.000 claims description 774
• 125000003277 amino group Chemical group 0.000 claims description 508
• -1 trifluoromethyl Methyl Chemical group 0.000 claims description 472
• 125000000217 alkyl group Chemical group 0.000 claims description 426
• 125000001424 substituent group Chemical group 0.000 claims description 210
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 177
• 239000011737 fluorine Substances 0.000 claims description 177
• 229910052731 fluorine Inorganic materials 0.000 claims description 177
• 229910052801 chlorine Inorganic materials 0.000 claims description 175
• 239000000460 chlorine Substances 0.000 claims description 174
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 172
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 172
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 171
• 229910052794 bromium Inorganic materials 0.000 claims description 171
• 125000003545 alkoxy group Chemical group 0.000 claims description 155
• 229920006395 saturated elastomer Polymers 0.000 claims description 154
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 123
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 121
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 119
• 125000002252 acyl group Chemical group 0.000 claims description 102
• 125000000623 heterocyclic group Chemical group 0.000 claims description 102
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 94
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 91
• 125000003118 aryl group Chemical group 0.000 claims description 86
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 85
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 83
• 125000001072 heteroaryl group Chemical group 0.000 claims description 78
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 77
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 77
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 74
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 71
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 67
• 125000004429 atom Chemical group 0.000 claims description 66
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 63
• 125000004414 alkyl thio group Chemical group 0.000 claims description 60
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 57
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 55
• 125000004076 pyridyl group Chemical group 0.000 claims description 53
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 51
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 49
• 208000002193 Pain Diseases 0.000 claims description 47
• 125000001544 thienyl group Chemical group 0.000 claims description 47
• 150000001412 amines Chemical class 0.000 claims description 45
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
• 229910052740 iodine Inorganic materials 0.000 claims description 44
• 125000005842 heteroatom Chemical group 0.000 claims description 42
• 239000011630 iodine Substances 0.000 claims description 41
• 150000001875 compounds Chemical class 0.000 claims description 40
• 125000004043 oxo group Chemical group O=* 0.000 claims description 40
• 229910052799 carbon Inorganic materials 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• 125000000468 ketone group Chemical group 0.000 claims description 37
• 230000036407 pain Effects 0.000 claims description 35
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 33
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• 150000007942 carboxylates Chemical group 0.000 claims description 28
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 27
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 25
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 23
• 125000004494 ethyl ester group Chemical group 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 21
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 21
• 125000004149 thio group Chemical group *S* 0.000 claims description 20
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 19
• 125000003172 aldehyde group Chemical group 0.000 claims description 17
• 239000000203 mixture Substances 0.000 claims description 16
• 238000006467 substitution reaction Methods 0.000 claims description 15
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 14
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 229940100389 Sulfonylurea Drugs 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 13
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 13
• ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
• 125000002757 morpholinyl group Chemical group 0.000 claims description 12
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 11
• 206010046543 Urinary incontinence Diseases 0.000 claims description 11
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 11
• 206010015037 epilepsy Diseases 0.000 claims description 11
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• RZOCKJZXQLKODN-UHFFFAOYSA-N trifluoromethoxycarbamic acid Chemical compound FC(ONC(=O)O)(F)F RZOCKJZXQLKODN-UHFFFAOYSA-N 0.000 claims description 11
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 10
• 239000002671 adjuvant Substances 0.000 claims description 10
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
• 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 9
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 229930194542 Keto Natural products 0.000 claims description 8
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 8
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
• 208000035475 disorder Diseases 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical group OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• ILFIRBGRMCGNOO-UHFFFAOYSA-N 1,1-bis($l^{1}-oxidanyl)ethene Chemical group [O]C([O])=C ILFIRBGRMCGNOO-UHFFFAOYSA-N 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
• 150000002431 hydrogen Chemical class 0.000 claims description 7
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 6
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
• 208000020925 Bipolar disease Diseases 0.000 claims description 6
• 206010012335 Dependence Diseases 0.000 claims description 6
• 208000019695 Migraine disease Diseases 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 6
• 239000004202 carbamide Substances 0.000 claims description 6
• 208000010877 cognitive disease Diseases 0.000 claims description 6
• 125000000879 imine group Chemical group 0.000 claims description 6
• 206010027599 migraine Diseases 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 239000011593 sulfur Substances 0.000 claims description 6
• 208000019901 Anxiety disease Diseases 0.000 claims description 5
• 208000012661 Dyskinesia Diseases 0.000 claims description 5
• 208000014094 Dystonic disease Diseases 0.000 claims description 5
• 208000015592 Involuntary movements Diseases 0.000 claims description 5
• RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 5
• 125000004442 acylamino group Chemical group 0.000 claims description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
• 125000005427 anthranyl group Chemical class 0.000 claims description 5
• 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
• 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 5
• 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
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 208000010118 dystonia Diseases 0.000 claims description 5
• 230000017311 musculoskeletal movement, spinal reflex action Effects 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 4
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
• 229930195733 hydrocarbon Natural products 0.000 claims description 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
• OTTPWWFPWBCJBS-UHFFFAOYSA-N o-(trifluoromethyl)hydroxylamine Chemical compound NOC(F)(F)F OTTPWWFPWBCJBS-UHFFFAOYSA-N 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical group C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 3
• JHCSBJAEVLXSGL-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)-n-[[4-(trifluoromethylsulfanyl)phenyl]methyl]quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(SC(F)(F)F)C=C1 JHCSBJAEVLXSGL-UHFFFAOYSA-N 0.000 claims description 3
• 239000004215 Carbon black (E152) Substances 0.000 claims description 3
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 3
• 150000001338 aliphatic hydrocarbons Chemical class 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
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 3
• 125000001841 imino group Chemical group [H]N=* 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
• 229960003194 meglumine Drugs 0.000 claims description 3
• PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 3
• 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 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
• SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 3
• 238000002360 preparation method Methods 0.000 claims description 3
• GJZRTERWIGITRR-UHFFFAOYSA-N 2-butylsulfanyl-n-[(3-fluorophenyl)methyl]-4-methyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCCCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 GJZRTERWIGITRR-UHFFFAOYSA-N 0.000 claims description 2
• DJHVPBBAOXXVAQ-UHFFFAOYSA-N 2-cyclohexylsulfanyl-n-[(3-fluorophenyl)methyl]-4-methyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C1CCCCC1SC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 DJHVPBBAOXXVAQ-UHFFFAOYSA-N 0.000 claims description 2
• TWWCMRROISPVRQ-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)-n-[(2,4,5-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=C1F TWWCMRROISPVRQ-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• VGYCCCPKMISTBB-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(1,3,4-oxadiazol-2-ylmethyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=NN=CO1 VGYCCCPKMISTBB-UHFFFAOYSA-N 0.000 claims description 2
• MWGVUZKBKRYEKP-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(4-methylpentyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound FC(F)(F)C1=CC=C2C(C)=C(C(=O)NCCCC(C)C)C(SCC)=NC2=C1 MWGVUZKBKRYEKP-UHFFFAOYSA-N 0.000 claims description 2
• YZELSMCHGJYNQE-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(naphthalen-2-ylmethyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C1=CC=CC2=CC(CNC(=O)C3=C(C)C4=CC=C(C=C4N=C3SCC)C(F)(F)F)=CC=C21 YZELSMCHGJYNQE-UHFFFAOYSA-N 0.000 claims description 2
• JVVRXTXGGYVPAJ-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(oxan-2-ylmethyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1CCCCO1 JVVRXTXGGYVPAJ-UHFFFAOYSA-N 0.000 claims description 2
• BPZASLDQFMWJDE-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-[(5-methylfuran-2-yl)methyl]-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(C)O1 BPZASLDQFMWJDE-UHFFFAOYSA-N 0.000 claims description 2
• BQUSIWROFGNJHZ-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-propyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C1=C(C(F)(F)F)C=C2N=C(SCC)C(C(=O)NCCC)=C(C)C2=C1 BQUSIWROFGNJHZ-UHFFFAOYSA-N 0.000 claims description 2
• 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 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
• LABJBBGATZAEOJ-UHFFFAOYSA-N 2-ethylsulfanyl-6-fluoro-n-[(4-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=C(F)C=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 LABJBBGATZAEOJ-UHFFFAOYSA-N 0.000 claims description 2
• DVPBKUXQKWCOCX-UHFFFAOYSA-N 2-ethylsulfanyl-7-fluoro-n-[(3-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(F)=CC=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 DVPBKUXQKWCOCX-UHFFFAOYSA-N 0.000 claims description 2
• KENKFKUDCKSCJA-UHFFFAOYSA-N 2-ethylsulfanyl-7-fluoro-n-[(4-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 KENKFKUDCKSCJA-UHFFFAOYSA-N 0.000 claims description 2
• OHILXZYXWBTIAZ-UHFFFAOYSA-N 2-ethylsulfanyl-N-[(3-fluorophenyl)methyl]-5-hydroxy-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=CC(O)=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 OHILXZYXWBTIAZ-UHFFFAOYSA-N 0.000 claims description 2
• RSHAXOBQFNTNFZ-UHFFFAOYSA-N 2-ethylsulfanyl-N-[(3-fluorophenyl)methyl]-7-hydroxy-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(O)=CC=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 RSHAXOBQFNTNFZ-UHFFFAOYSA-N 0.000 claims description 2
• JNDKOXNXROGEGL-UHFFFAOYSA-N 2-ethylsulfanyl-n-(furan-2-ylmethyl)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=CO1 JNDKOXNXROGEGL-UHFFFAOYSA-N 0.000 claims description 2
• FLOGQWJVRCMVLX-UHFFFAOYSA-N 2-ethylsulfanyl-n-[(3-fluorophenyl)methyl]-4,7-dimethylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C)=CC=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 FLOGQWJVRCMVLX-UHFFFAOYSA-N 0.000 claims description 2
• MJFLPXIKFLITQN-UHFFFAOYSA-N 2-ethylsulfanyl-n-[(3-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=CC(F)=C1 MJFLPXIKFLITQN-UHFFFAOYSA-N 0.000 claims description 2
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