ZA200500886B - "1,2,4" Oxadiazoles as modulators of metabotropic glutamate receptor-5 - Google Patents

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Publication number

ZA200500886B

ZA200500886B ZA200500886A ZA200500886A ZA200500886B ZA 200500886 B ZA200500886 B ZA 200500886B ZA 200500886 A ZA200500886 A ZA 200500886A ZA 200500886 A ZA200500886 A ZA 200500886A ZA 200500886 B ZA200500886 B ZA 200500886B

Authority

ZA

South Africa

Prior art keywords

triazol

phenyl

methyl

chloro

ylsulfanylmethyl

Prior art date

2002-08-09

Links

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• 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 title claims description 4
• 102100038357 Metabotropic glutamate receptor 5 Human genes 0.000 title description 2
• 150000004866 oxadiazoles Chemical class 0.000 title 1
• -1 Cy.¢alkylcyano Chemical group 0.000 claims description 151
• 229910052799 carbon Inorganic materials 0.000 claims description 72
• 229910052757 nitrogen Inorganic materials 0.000 claims description 71
• 150000001875 compounds Chemical class 0.000 claims description 70
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 229910052760 oxygen Inorganic materials 0.000 claims description 60
• 229910052717 sulfur Inorganic materials 0.000 claims description 52
• 125000004429 atom Chemical group 0.000 claims description 49
• 229910052739 hydrogen Inorganic materials 0.000 claims description 46
• 239000001257 hydrogen Substances 0.000 claims description 46
• 125000005843 halogen group Chemical group 0.000 claims description 38
• 150000002431 hydrogen Chemical class 0.000 claims description 38
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
• 102000016193 Metabotropic glutamate receptors Human genes 0.000 claims description 28
• 108010010914 Metabotropic glutamate receptors Proteins 0.000 claims description 28
• 102000005962 receptors Human genes 0.000 claims description 22
• 108020003175 receptors Proteins 0.000 claims description 22
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 16
• 230000004913 activation Effects 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
• 208000035475 disorder Diseases 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
• 208000002193 Pain Diseases 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 230000001404 mediated effect Effects 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 238000000034 method Methods 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 10
• OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000002883 imidazolyl group Chemical group 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
• 125000005494 pyridonyl group Chemical group 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 8
• 125000000335 thiazolyl group Chemical group 0.000 claims description 8
• 229930192474 thiophene Natural products 0.000 claims description 8
• 125000001425 triazolyl group Chemical group 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000005872 benzooxazolyl group Chemical group 0.000 claims description 6
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
• 125000005945 imidazopyridyl group Chemical group 0.000 claims description 6
• 238000001783 near-resonance Rayleigh scattering spectroscopy Methods 0.000 claims description 6
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 6
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 6
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
• 208000000094 Chronic Pain Diseases 0.000 claims description 5
• 208000012902 Nervous system disease Diseases 0.000 claims description 5
• 208000025966 Neurological disease Diseases 0.000 claims description 5
• 208000005298 acute pain Diseases 0.000 claims description 5
• 125000004043 oxo group Chemical group O=* 0.000 claims description 5
• 208000020016 psychiatric disease Diseases 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
• 230000001684 chronic effect Effects 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• 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 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000001424 substituent group Chemical group 0.000 claims description 3
• YOXQYPMPVOTYNO-UHFFFAOYSA-N 2-[5-(4-bromophenyl)furan-2-yl]-5-[2-[5-[5-(4-bromophenyl)furan-2-yl]-1,3,4-oxadiazol-2-yl]ethyl]-1,3,4-oxadiazole Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=2OC(CCC=3OC(=NN=3)C=3OC(=CC=3)C=3C=CC(Br)=CC=3)=NN=2)O1 YOXQYPMPVOTYNO-UHFFFAOYSA-N 0.000 claims description 2
• OCOWVEJKROOBDS-UHFFFAOYSA-N 5-[(4-methyl-1,2,4-triazol-3-yl)sulfanylmethyl]-3-thiophen-3-yl-1,2,4-oxadiazole Chemical compound CN1C=NN=C1SCC1=NC(C2=CSC=C2)=NO1 OCOWVEJKROOBDS-UHFFFAOYSA-N 0.000 claims description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 222
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 125
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 33
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 28
• 230000002265 prevention Effects 0.000 claims 16
• BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 12
• BSKHPKMHTQYZBB-UHFFFAOYSA-N alpha-methylpyridine Natural products CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 7
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 5
• 125000002877 alkyl aryl group Chemical group 0.000 claims 5
• ZNABSHLRJQDSCG-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[2-(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)propyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(C2CC2)C=1C(C)CC(ON=1)=NC=1C1=CC=CC(Cl)=C1 ZNABSHLRJQDSCG-UHFFFAOYSA-N 0.000 claims 4
• KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 4
• TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims 4
• 150000003852 triazoles Chemical class 0.000 claims 4
• HBFYWPRDLRYEPE-UHFFFAOYSA-N 2-[2-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]propyl]-5-pyridin-4-yl-1,3,4-oxadiazole Chemical compound N=1C(C=2C=C(Cl)C=CC=2)=NOC=1C(C)CC(O1)=NN=C1C1=CC=NC=C1 HBFYWPRDLRYEPE-UHFFFAOYSA-N 0.000 claims 3
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 3
• OUSRSXCQBDMDGQ-UHFFFAOYSA-N (2-chlorophenyl)-[5-[[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]methylsulfanyl]-4-(2-methylpropyl)-1,2,4-triazol-3-yl]methanol Chemical compound N=1N=C(C(O)C=2C(=CC=CC=2)Cl)N(CC(C)C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 OUSRSXCQBDMDGQ-UHFFFAOYSA-N 0.000 claims 2
• NTSVMXNABGFNSI-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3-oxazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1SCC(N=1)=COC=1C1=CC=CC(Cl)=C1 NTSVMXNABGFNSI-UHFFFAOYSA-N 0.000 claims 2
• WMRWZYRJDGFQOS-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(O1)=NN=C1C1=CC=CC(Cl)=C1 WMRWZYRJDGFQOS-UHFFFAOYSA-N 0.000 claims 2
• BXJXMGITDPAWOO-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[1-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SC(C)C(O1)=NN=C1C1=CC=CC(Cl)=C1 BXJXMGITDPAWOO-UHFFFAOYSA-N 0.000 claims 2
• HTKNGHQKKORTCR-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[2-[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]ethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1CCC(O1)=NN=C1C1=CC=CC(Cl)=C1 HTKNGHQKKORTCR-UHFFFAOYSA-N 0.000 claims 2
• YZBRMLUGMHIBRW-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[2-[5-(furan-2-yl)-4-methyl-1,2,4-triazol-3-yl]ethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(C)C=1CCC(O1)=NN=C1C1=CC=CC(Cl)=C1 YZBRMLUGMHIBRW-UHFFFAOYSA-N 0.000 claims 2
• KZURXYAMJYZOBO-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[[4-cyclopropyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,3,4-oxadiazole Chemical compound ClC1=CC=CC(C=2OC(CSC=3N(C(C=4OC=CC=4)=NN=3)C3CC3)=NN=2)=C1 KZURXYAMJYZOBO-UHFFFAOYSA-N 0.000 claims 2
• ULWHKXNKMVUFEE-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[[4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC(O1)=NN=C1C1=CC=CC(Cl)=C1 ULWHKXNKMVUFEE-UHFFFAOYSA-N 0.000 claims 2
• KUUCPQZYDHJKPG-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[[4-methyl-5-(1,3-thiazol-4-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2N=CSC=2)N(C)C=1SCC(O1)=NN=C1C1=CC=CC(Cl)=C1 KUUCPQZYDHJKPG-UHFFFAOYSA-N 0.000 claims 2
• DLAVPWKEQZNLKI-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[[5-(4-methoxyphenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,3,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1C(N1C)=NN=C1SCC1=NN=C(C=2C=C(Cl)C=CC=2)O1 DLAVPWKEQZNLKI-UHFFFAOYSA-N 0.000 claims 2
• QKXRKEITNCCVFO-UHFFFAOYSA-N 2-(5-chloro-2-fluorophenyl)-5-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(O1)=NN=C1C1=CC(Cl)=CC=C1F QKXRKEITNCCVFO-UHFFFAOYSA-N 0.000 claims 2
• YXFMOEVKXZGLNU-UHFFFAOYSA-N 2-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(2-methylpyridin-4-yl)-1,3,4-oxadiazole Chemical compound C1=NC(C)=CC(C=2OC(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)=NN=2)=C1 YXFMOEVKXZGLNU-UHFFFAOYSA-N 0.000 claims 2
• DMLDGIMNZIUYFE-UHFFFAOYSA-N 2-[1-[[4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-5-(2-methylpyridin-4-yl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SC(C)C(O1)=NN=C1C1=CC=NC(C)=C1 DMLDGIMNZIUYFE-UHFFFAOYSA-N 0.000 claims 2
• MLGZSMLWWKJDRS-UHFFFAOYSA-N 2-[1-[[5-(furan-2-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]-5-(2-methylpyridin-4-yl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=C(C)N=CC=2)OC=1C(C)SC(N1C)=NN=C1C1=CC=CO1 MLGZSMLWWKJDRS-UHFFFAOYSA-N 0.000 claims 2
• CMGFJVMEUMGONW-UHFFFAOYSA-N 2-[3-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazol-5-yl]-4-methylphenol Chemical compound CC1=CC=C(O)C(C=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=2)=C1 CMGFJVMEUMGONW-UHFFFAOYSA-N 0.000 claims 2
• ILBBYJLQTQJUQN-UHFFFAOYSA-N 2-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-methylphenyl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(O1)=NN=C1C1=CC=CC(C)=C1 ILBBYJLQTQJUQN-UHFFFAOYSA-N 0.000 claims 2
• GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 claims 2
• OKEHURCMYKPVFW-UHFFFAOYSA-N 2-methoxythiophene Chemical compound COC1=CC=CS1 OKEHURCMYKPVFW-UHFFFAOYSA-N 0.000 claims 2
• XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 claims 2
• OQPNEGFPIPPLMT-UHFFFAOYSA-N 3-(1h-benzimidazol-2-ylsulfanylmethyl)-5-(3-methoxyphenyl)-1,2,4-oxadiazole Chemical compound COC1=CC=CC(C=2ON=C(CSC=3NC4=CC=CC=C4N=3)N=2)=C1 OQPNEGFPIPPLMT-UHFFFAOYSA-N 0.000 claims 2
• XFOZJPDZNJSRGN-UHFFFAOYSA-N 3-(1h-benzimidazol-2-ylsulfanylmethyl)-5-(3-methylsulfanylphenyl)-1,2,4-oxadiazole Chemical compound CSC1=CC=CC(C=2ON=C(CSC=3NC4=CC=CC=C4N=3)N=2)=C1 XFOZJPDZNJSRGN-UHFFFAOYSA-N 0.000 claims 2
• GKCXMQKTLIXVNI-UHFFFAOYSA-N 3-(1h-imidazo[4,5-b]pyridin-2-ylsulfanylmethyl)-5-(3-methoxyphenyl)-1,2,4-oxadiazole Chemical compound COC1=CC=CC(C=2ON=C(CSC=3NC4=CC=CN=C4N=3)N=2)=C1 GKCXMQKTLIXVNI-UHFFFAOYSA-N 0.000 claims 2
• ALLSGPSLURSREQ-UHFFFAOYSA-N 3-(2,5-difluorophenyl)-5-[[5-(furan-2-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(C)C=1SCC(ON=1)=NC=1C1=CC(F)=CC=C1F ALLSGPSLURSREQ-UHFFFAOYSA-N 0.000 claims 2
• GZINSWYCDFVOLK-UHFFFAOYSA-N 3-(2-fluoro-5-methylphenyl)-5-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=C(F)C(C=2N=C(CSC=3N(C(C=4C=NC=CC=4)=NN=3)C)ON=2)=C1 GZINSWYCDFVOLK-UHFFFAOYSA-N 0.000 claims 2
• UAMZXDHZDGFYSZ-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(4-methyl-5-pyrimidin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2N=CN=CC=2)N(C)C=1SCC(ON=1)=NC=1C1=CC=CC(Cl)=C1 UAMZXDHZDGFYSZ-UHFFFAOYSA-N 0.000 claims 2
• DGMHSHCJPYYMBR-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[1-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1C(C=2C=C(Cl)C=CC=2)=NOC=1C(C)SC(N1C)=NN=C1C1=CC=CS1 DGMHSHCJPYYMBR-UHFFFAOYSA-N 0.000 claims 2
• RIPPGLFDJGGJAF-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[[4-ethyl-5-(2-methoxyethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CCN1C(CCOC)=NN=C1SCC1=NC(C=2C=C(Cl)C=CC=2)=NO1 RIPPGLFDJGGJAF-UHFFFAOYSA-N 0.000 claims 2
• MNRNEARDLAQMNG-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(ON=1)=NC=1C1=CC=CC(Cl)=C1 MNRNEARDLAQMNG-UHFFFAOYSA-N 0.000 claims 2
• PHVCRIYWGCGBJL-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[[4-ethyl-5-(methoxymethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CCN1C(COC)=NN=C1SCC1=NC(C=2C=C(Cl)C=CC=2)=NO1 PHVCRIYWGCGBJL-UHFFFAOYSA-N 0.000 claims 2
• POOIAPQDQJUGKU-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[[5-(furan-3-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C2=COC=C2)N(C)C=1SCC(ON=1)=NC=1C1=CC=CC(Cl)=C1 POOIAPQDQJUGKU-UHFFFAOYSA-N 0.000 claims 2
• BSSCWAKAOAJZNW-UHFFFAOYSA-N 3-(3-fluorophenyl)-5-[(4-methyl-5-thiophen-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C2=CSC=C2)N(C)C=1SCC(ON=1)=NC=1C1=CC=CC(F)=C1 BSSCWAKAOAJZNW-UHFFFAOYSA-N 0.000 claims 2
• MRLGYRLNPLLMMI-UHFFFAOYSA-N 3-(3-methoxyphenyl)-5-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound COC1=CC=CC(C=2N=C(CSC=3N(C(C=4SC=CC=4)=NN=3)C)ON=2)=C1 MRLGYRLNPLLMMI-UHFFFAOYSA-N 0.000 claims 2
• JXDVYCPGGPJJHX-UHFFFAOYSA-N 3-(5-chloro-2-fluorophenyl)-5-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(ON=1)=NC=1C1=CC(Cl)=CC=C1F JXDVYCPGGPJJHX-UHFFFAOYSA-N 0.000 claims 2
• JDAVULZPYAGASP-UHFFFAOYSA-N 3-[(4-ethyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(C)=C1 JDAVULZPYAGASP-UHFFFAOYSA-N 0.000 claims 2
• CNXAYRIHLXOIBT-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C)=CC=C1F CNXAYRIHLXOIBT-UHFFFAOYSA-N 0.000 claims 2
• COHTWMLCHHQHSA-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(C)=C1 COHTWMLCHHQHSA-UHFFFAOYSA-N 0.000 claims 2
• SEPQUPXZLIWDMG-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C2=CSC=C2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(C)=C1 SEPQUPXZLIWDMG-UHFFFAOYSA-N 0.000 claims 2
• ZEMWXQPZCKUZRM-UHFFFAOYSA-N 3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(1,3-thiazol-4-yl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CSC=N1 ZEMWXQPZCKUZRM-UHFFFAOYSA-N 0.000 claims 2
• VUDUCRTZCYOQHS-UHFFFAOYSA-N 3-[(4-methyl-5-thiophen-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-thiophen-2-yl-1,2,4-oxadiazole Chemical compound N=1N=C(C2=CSC=C2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CS1 VUDUCRTZCYOQHS-UHFFFAOYSA-N 0.000 claims 2
• MLNNQOPIYMHFMZ-UHFFFAOYSA-N 3-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-5-(3-methoxyphenyl)-1,2,4-oxadiazole Chemical compound COC1=CC=CC(C=2ON=C(N=2)C(C)SC=2N(C(C=3C=CN=CC=3)=NN=2)C2CC2)=C1 MLNNQOPIYMHFMZ-UHFFFAOYSA-N 0.000 claims 2
• GTVRFBCWAHCPMG-UHFFFAOYSA-N 3-[1-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-5-(2-fluoro-5-methylphenyl)-1,2-oxazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SC(C)C(=NO1)C=C1C1=CC(C)=CC=C1F GTVRFBCWAHCPMG-UHFFFAOYSA-N 0.000 claims 2
• WMGYQRPMXDUCCX-UHFFFAOYSA-N 3-[1-[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]ethylsulfanyl]-5-pyridin-4-yl-1,2,4-triazol-4-amine Chemical compound N=1N=C(C=2C=C(Cl)C=CC=2)OC=1C(C)SC(N1N)=NN=C1C1=CC=NC=C1 WMGYQRPMXDUCCX-UHFFFAOYSA-N 0.000 claims 2
• YWOWWCALYZWZEP-UHFFFAOYSA-N 3-[3-[1-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound N=1OC(C=2C=C(C=CC=2)C#N)=NC=1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 YWOWWCALYZWZEP-UHFFFAOYSA-N 0.000 claims 2
• MNLLLRRKPYVSAH-UHFFFAOYSA-N 3-[3-[[5-(3-chlorothiophen-2-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound N=1N=C(C2=C(C=CS2)Cl)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(C#N)=C1 MNLLLRRKPYVSAH-UHFFFAOYSA-N 0.000 claims 2
• MNUUTELSCJACCG-UHFFFAOYSA-N 3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,2-oxazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(=NO1)C=C1C1=CC(C)=CC=C1F MNUUTELSCJACCG-UHFFFAOYSA-N 0.000 claims 2
• LUMNYCRVFWVRIY-UHFFFAOYSA-N 3-[[4-ethyl-5-(oxolan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C2OCCC2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(C)=C1 LUMNYCRVFWVRIY-UHFFFAOYSA-N 0.000 claims 2
• PJNUFBUGGIPPPH-UHFFFAOYSA-N 3-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-thiophen-3-yl-1,2,4-oxadiazole Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC=2N=C(ON=2)C2=CSC=C2)=N1 PJNUFBUGGIPPPH-UHFFFAOYSA-N 0.000 claims 2
• KJFXTEQFPJWRER-UHFFFAOYSA-N 3-[[5-(2,6-dichloropyridin-4-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CSC=3N(C(C=4C=C(Cl)N=C(Cl)C=4)=NN=3)C)N=2)=C1 KJFXTEQFPJWRER-UHFFFAOYSA-N 0.000 claims 2
• AJRGDQWFWJDYDP-UHFFFAOYSA-N 3-chloro-1,2-oxazole Chemical compound ClC=1C=CON=1 AJRGDQWFWJDYDP-UHFFFAOYSA-N 0.000 claims 2
• CUMCMYMKECWGHO-UHFFFAOYSA-N 3-methyl-1,2-oxazole Chemical compound CC=1C=CON=1 CUMCMYMKECWGHO-UHFFFAOYSA-N 0.000 claims 2
• LTVREEOZCOPBRN-UHFFFAOYSA-N 4-[[5-[[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]methoxy]phenol Chemical compound N=1N=C(SCC=2N=C(ON=2)C=2C=C(Cl)C=CC=2)N(CC)C=1COC1=CC=C(O)C=C1 LTVREEOZCOPBRN-UHFFFAOYSA-N 0.000 claims 2
• WMXVMYBJSRMVTK-UHFFFAOYSA-N 4-benzyl-2-[4-methyl-5-[[5-(3-methylphenyl)-1,2,4-oxadiazol-3-yl]methylsulfanyl]-1,2,4-triazol-3-yl]morpholine Chemical compound CC1=CC=CC(C=2ON=C(CSC=3N(C(C4OCCN(CC=5C=CC=CC=5)C4)=NN=3)C)N=2)=C1 WMXVMYBJSRMVTK-UHFFFAOYSA-N 0.000 claims 2
• DWQMVWMNLWYLCE-UHFFFAOYSA-N 5-(2,5-dichlorophenyl)-3-[(4-ethyl-5-thiophen-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C2=CSC=C2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(Cl)=CC=C1Cl DWQMVWMNLWYLCE-UHFFFAOYSA-N 0.000 claims 2
• GRNDAPWRNZWJDN-UHFFFAOYSA-N 5-(2,5-difluorophenyl)-3-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(F)=CC=C1F GRNDAPWRNZWJDN-UHFFFAOYSA-N 0.000 claims 2
• AFPGSICNGIINDI-UHFFFAOYSA-N 5-(2,5-difluorophenyl)-3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(F)=CC=C1F AFPGSICNGIINDI-UHFFFAOYSA-N 0.000 claims 2
• UCHDIIADCUAHRS-UHFFFAOYSA-N 5-(2,5-difluorophenyl)-3-[(4-ethyl-5-thiophen-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C2=CSC=C2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(F)=CC=C1F UCHDIIADCUAHRS-UHFFFAOYSA-N 0.000 claims 2
• OAUQQTCROZXFPF-UHFFFAOYSA-N 5-(2,5-difluorophenyl)-3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(F)=CC=C1F OAUQQTCROZXFPF-UHFFFAOYSA-N 0.000 claims 2
• BVNOOFHAASAPDA-UHFFFAOYSA-N 5-(2,5-dimethylphenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=C(C)C(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)C)N=2)=C1 BVNOOFHAASAPDA-UHFFFAOYSA-N 0.000 claims 2
• QKZIOSZGVGFRRM-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC=C1Cl QKZIOSZGVGFRRM-UHFFFAOYSA-N 0.000 claims 2
• FMQXAKIGOZZDAL-UHFFFAOYSA-N 5-(2-chloropyridin-4-yl)-3-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound C1=NC(Cl)=CC(C=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=2)=C1 FMQXAKIGOZZDAL-UHFFFAOYSA-N 0.000 claims 2
• PJXDKKYWNKTKDH-UHFFFAOYSA-N 5-(2-fluoro-5-methylphenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=C(F)C(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)C)N=2)=C1 PJXDKKYWNKTKDH-UHFFFAOYSA-N 0.000 claims 2
• WCPVASMMXJWICK-UHFFFAOYSA-N 5-(2-fluorophenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC=C1F WCPVASMMXJWICK-UHFFFAOYSA-N 0.000 claims 2
• PMVPMCSWEIASMZ-UHFFFAOYSA-N 5-(2-methoxyphenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound COC1=CC=CC=C1C1=NC(CSC=2N(C(C=3SC=CC=3)=NN=2)C)=NO1 PMVPMCSWEIASMZ-UHFFFAOYSA-N 0.000 claims 2
• QDECZUYNVXPYBJ-UHFFFAOYSA-N 5-(2-methylpyridin-4-yl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound C1=NC(C)=CC(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)C)N=2)=C1 QDECZUYNVXPYBJ-UHFFFAOYSA-N 0.000 claims 2
• VNDDCQMEFUVUGP-UHFFFAOYSA-N 5-(3-chlorophenyl)-2-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3-oxazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(O1)=NC=C1C1=CC=CC(Cl)=C1 VNDDCQMEFUVUGP-UHFFFAOYSA-N 0.000 claims 2
• DLRVNGFMSUOVDF-UHFFFAOYSA-N 5-(3-chlorophenyl)-2-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,3-oxazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(O1)=NC=C1C1=CC=CC(Cl)=C1 DLRVNGFMSUOVDF-UHFFFAOYSA-N 0.000 claims 2
• RNNGGRAGEVFIFX-UHFFFAOYSA-N 5-(3-chlorophenyl)-2-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,3-oxazole Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC=2OC(=CN=2)C=2C=C(Cl)C=CC=2)=N1 RNNGGRAGEVFIFX-UHFFFAOYSA-N 0.000 claims 2
• PISVVOOSADIMGE-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 PISVVOOSADIMGE-UHFFFAOYSA-N 0.000 claims 2
• UUALMNKSIQRDJF-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-methyl-5-pyrimidin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2N=CN=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 UUALMNKSIQRDJF-UHFFFAOYSA-N 0.000 claims 2
• LHAVWNNARPYZLN-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-propyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CCC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 LHAVWNNARPYZLN-UHFFFAOYSA-N 0.000 claims 2
• MPAJKCBBDDZNIY-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-1,2-oxazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SC(C)C(=NO1)C=C1C1=CC=CC(Cl)=C1 MPAJKCBBDDZNIY-UHFFFAOYSA-N 0.000 claims 2
• STTVHILXNWIIQL-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[2-(furan-2-yl)-3-methylimidazol-4-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound C=1N=C(C=2OC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 STTVHILXNWIIQL-UHFFFAOYSA-N 0.000 claims 2
• JCMVYEFOOAUPHL-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(4-fluorophenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CC(F)=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 JCMVYEFOOAUPHL-UHFFFAOYSA-N 0.000 claims 2
• NGCOSTLGFWFGCH-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2-oxazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC(=NO1)C=C1C1=CC=CC(Cl)=C1 NGCOSTLGFWFGCH-UHFFFAOYSA-N 0.000 claims 2
• GRGQWHCBZQXYOI-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2-oxazole Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC2=NOC(=C2)C=2C=C(Cl)C=CC=2)=N1 GRGQWHCBZQXYOI-UHFFFAOYSA-N 0.000 claims 2
• PPGCELFTJCIQKO-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-[(4-methoxyphenoxy)methyl]-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(SCC=2N=C(ON=2)C=2C=C(Cl)C=CC=2)N(CC)C=1COC1=CC=C(OC)C=C1 PPGCELFTJCIQKO-UHFFFAOYSA-N 0.000 claims 2
• PCYFPLUJHRZXHP-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-methyl-5-(1-oxidopyridin-1-ium-4-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C[N+]([O-])=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 PCYFPLUJHRZXHP-UHFFFAOYSA-N 0.000 claims 2
• SQLWTJQDLLUPMR-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(2-fluorophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C(=CC=CC=2)F)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 SQLWTJQDLLUPMR-UHFFFAOYSA-N 0.000 claims 2
• NYBOLTGXTOYXDM-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(3-fluorophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C(F)C=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 NYBOLTGXTOYXDM-UHFFFAOYSA-N 0.000 claims 2
• KOKFKFBMUOWJSP-UHFFFAOYSA-N 5-(3-fluorophenyl)-3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(F)=C1 KOKFKFBMUOWJSP-UHFFFAOYSA-N 0.000 claims 2
• SAMSMMJVUFGISH-UHFFFAOYSA-N 5-(3-fluorophenyl)-3-[(4-methyl-5-thiophen-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C2=CSC=C2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(F)=C1 SAMSMMJVUFGISH-UHFFFAOYSA-N 0.000 claims 2
• YQORNKOGZVKMLV-UHFFFAOYSA-N 5-(3-iodophenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(I)=C1 YQORNKOGZVKMLV-UHFFFAOYSA-N 0.000 claims 2
• ATWIRKKUFPRTBY-UHFFFAOYSA-N 5-(3-methylphenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfinylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CS(=O)C=3N(C(C=4SC=CC=4)=NN=3)C)N=2)=C1 ATWIRKKUFPRTBY-UHFFFAOYSA-N 0.000 claims 2
• OQFCQRMIQQRPQU-UHFFFAOYSA-N 5-(3-methylphenyl)-3-[[4-methyl-5-(1,3-thiazol-4-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CSC=3N(C(C=4N=CSC=4)=NN=3)C)N=2)=C1 OQFCQRMIQQRPQU-UHFFFAOYSA-N 0.000 claims 2
• MKPLRZVBULASCK-UHFFFAOYSA-N 5-(3-methylphenyl)-3-[[4-methyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CSC=3N(C(=NN=3)C(F)(F)F)C)N=2)=C1 MKPLRZVBULASCK-UHFFFAOYSA-N 0.000 claims 2
• NOOSFLNXDDIFJE-UHFFFAOYSA-N 5-(4-methoxythiophen-3-yl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound COC1=CSC=C1C1=NC(CSC=2N(C(C=3SC=CC=3)=NN=2)C)=NO1 NOOSFLNXDDIFJE-UHFFFAOYSA-N 0.000 claims 2
• KFPGGZGHKKLMAE-UHFFFAOYSA-N 5-(5-bromo-2-fluorophenyl)-3-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=NC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC(Br)=CC=C1F KFPGGZGHKKLMAE-UHFFFAOYSA-N 0.000 claims 2
• RVUKWCXLYZKTMC-UHFFFAOYSA-N 5-(5-bromo-2-fluorophenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC(Br)=CC=C1F RVUKWCXLYZKTMC-UHFFFAOYSA-N 0.000 claims 2
• YBTREHJSDIAZGA-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-3-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2-oxazole Chemical compound FC1=CC=C(Cl)C=C1C1=CC(CSC=2N(C(C=3C=CN=CC=3)=NN=2)C2CC2)=NO1 YBTREHJSDIAZGA-UHFFFAOYSA-N 0.000 claims 2
• DLXNDJPBHJMKKT-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-3-[(4-cyclopropyl-5-pyrimidin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound FC1=CC=C(Cl)C=C1C1=NC(CSC=2N(C(C=3N=CN=CC=3)=NN=2)C2CC2)=NO1 DLXNDJPBHJMKKT-UHFFFAOYSA-N 0.000 claims 2
• WJDDDFDGKQYEIA-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-3-[1-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1OC(C=2C(=CC=C(Cl)C=2)F)=NC=1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 WJDDDFDGKQYEIA-UHFFFAOYSA-N 0.000 claims 2
• HHFMMESDZHCQAJ-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-3-[[4-(2-fluoroethyl)-5-thiophen-2-yl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CCF)C=1SCC(N=1)=NOC=1C1=CC(Cl)=CC=C1F HHFMMESDZHCQAJ-UHFFFAOYSA-N 0.000 claims 2
• QQRHWDAJHUONHR-UHFFFAOYSA-N 5-(5-chlorothiophen-2-yl)-3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=C(Cl)S1 QQRHWDAJHUONHR-UHFFFAOYSA-N 0.000 claims 2
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• HMPRNAWUOORIAA-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[1-[[4-methyl-5-(2-methylpyridin-4-yl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=C(Cl)C=CC=2)OC=1C(C)SC(N1C)=NN=C1C1=CC=NC(C)=C1 HMPRNAWUOORIAA-UHFFFAOYSA-N 0.000 claims 1
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• YJRMEWCVLKPBTR-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,3,4-oxadiazole Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC=2OC(=NN=2)C=2C=C(Cl)C=CC=2)=N1 YJRMEWCVLKPBTR-UHFFFAOYSA-N 0.000 claims 1
• LJQPFOILFKBCSR-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[[5-(furan-2-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(C)C=1SCC(O1)=NN=C1C1=CC=CC(Cl)=C1 LJQPFOILFKBCSR-UHFFFAOYSA-N 0.000 claims 1
• IJJNQTFUAXXXCS-UHFFFAOYSA-N 2-(3-methylphenyl)-5-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3,4-oxadiazole Chemical compound CC1=CC=CC(C=2OC(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C)=NN=2)=C1 IJJNQTFUAXXXCS-UHFFFAOYSA-N 0.000 claims 1
• KSTGNASRKIUJCU-UHFFFAOYSA-N 2-(5-chloro-2-fluorophenyl)-5-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3,4-oxadiazole Chemical compound FC1=CC=C(Cl)C=C1C(O1)=NN=C1CSC(N1C2CC2)=NN=C1C1=CC=NC=C1 KSTGNASRKIUJCU-UHFFFAOYSA-N 0.000 claims 1
• UELSNOKJLLTGPU-UHFFFAOYSA-N 2-(5-chloro-2-fluorophenyl)-5-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1SCC(O1)=NN=C1C1=CC(Cl)=CC=C1F UELSNOKJLLTGPU-UHFFFAOYSA-N 0.000 claims 1
• KUMOBSCBPBTFQL-UHFFFAOYSA-N 2-(5-chloro-2-fluorophenyl)-5-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C(=CC=C(Cl)C=2)F)OC=1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 KUMOBSCBPBTFQL-UHFFFAOYSA-N 0.000 claims 1
• UKIPZEGXADMCFP-UHFFFAOYSA-N 2-(5-chloro-2-fluorophenyl)-5-[1-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SC(C)C(O1)=NN=C1C1=CC(Cl)=CC=C1F UKIPZEGXADMCFP-UHFFFAOYSA-N 0.000 claims 1
• BOHIAMNRXPRDQH-UHFFFAOYSA-N 2-(5-chloro-2-fluorophenyl)-5-[1-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C(=CC=C(Cl)C=2)F)OC=1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 BOHIAMNRXPRDQH-UHFFFAOYSA-N 0.000 claims 1
• FXXMHIIFFKJSOE-UHFFFAOYSA-N 2-(5-chloro-2-fluorophenyl)-5-[1-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SC(C)C(O1)=NN=C1C1=CC(Cl)=CC=C1F FXXMHIIFFKJSOE-UHFFFAOYSA-N 0.000 claims 1
• IDNLAZRWSIDOAH-UHFFFAOYSA-N 2-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(O1)=NN=C1C1=CC(C)=CC=C1F IDNLAZRWSIDOAH-UHFFFAOYSA-N 0.000 claims 1
• GICJXFMWFZVMFF-UHFFFAOYSA-N 2-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-nitrophenyl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(O1)=NN=C1C1=CC=CC([N+]([O-])=O)=C1 GICJXFMWFZVMFF-UHFFFAOYSA-N 0.000 claims 1
• NHLRJWHMULKPEG-UHFFFAOYSA-N 2-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-5-(2-methylpyridin-4-yl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=C(C)N=CC=2)OC=1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 NHLRJWHMULKPEG-UHFFFAOYSA-N 0.000 claims 1
• HUVYFWDAHBIMRN-UHFFFAOYSA-N 2-[1-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]-2-methylpropan-2-yl]-5-pyridin-4-yl-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)OC=1C(C)(C)CC(ON=1)=NC=1C1=CC=CC(Cl)=C1 HUVYFWDAHBIMRN-UHFFFAOYSA-N 0.000 claims 1
• HJKDGITWOQICHW-UHFFFAOYSA-N 2-[1-[[5-(3-fluorophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]-5-(2-methylpyridin-4-yl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=C(C)N=CC=2)OC=1C(C)SC(N1C)=NN=C1C1=CC=CC(F)=C1 HJKDGITWOQICHW-UHFFFAOYSA-N 0.000 claims 1
• BRNPQSMFSBIADD-UHFFFAOYSA-N 2-[1-[[5-(4-methoxyphenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]-5-(2-methylpyridin-4-yl)-1,3,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1C(N1C)=NN=C1SC(C)C1=NN=C(C=2C=C(C)N=CC=2)O1 BRNPQSMFSBIADD-UHFFFAOYSA-N 0.000 claims 1
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• VQMFCMDRYLAJTR-UHFFFAOYSA-N 2-[[5-(3-methylphenyl)-1,2,4-oxadiazol-3-yl]methylsulfanyl]-5-(2-methyl-1,3-thiazol-4-yl)-1,3,4-oxadiazole Chemical compound S1C(C)=NC(C=2OC(SCC=3N=C(ON=3)C=3C=C(C)C=CC=3)=NN=2)=C1 VQMFCMDRYLAJTR-UHFFFAOYSA-N 0.000 claims 1
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• JDIGJDHRJKIHND-UHFFFAOYSA-N 3-(1h-benzimidazol-2-ylsulfanylmethyl)-5-(3-iodophenyl)-1,2,4-oxadiazole Chemical compound IC1=CC=CC(C=2ON=C(CSC=3NC4=CC=CC=C4N=3)N=2)=C1 JDIGJDHRJKIHND-UHFFFAOYSA-N 0.000 claims 1
• XCFRLZNSQHJQTF-UHFFFAOYSA-N 3-(1h-benzimidazol-2-ylsulfanylmethyl)-5-[3-(methoxymethyl)phenyl]-1,2,4-oxadiazole Chemical compound COCC1=CC=CC(C=2ON=C(CSC=3NC4=CC=CC=C4N=3)N=2)=C1 XCFRLZNSQHJQTF-UHFFFAOYSA-N 0.000 claims 1
• PQJRLGVEHBARMI-UHFFFAOYSA-N 3-(2,5-difluorophenyl)-5-[(4-ethyl-5-pyrimidin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2N=CN=CC=2)N(CC)C=1SCC(ON=1)=NC=1C1=CC(F)=CC=C1F PQJRLGVEHBARMI-UHFFFAOYSA-N 0.000 claims 1
• SOBVQBQYECNUMJ-UHFFFAOYSA-N 3-(2,5-difluorophenyl)-5-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(ON=1)=NC=1C1=CC(F)=CC=C1F SOBVQBQYECNUMJ-UHFFFAOYSA-N 0.000 claims 1
• RIJNQCHNXCZMKB-UHFFFAOYSA-N 3-(2-fluoro-5-methylphenyl)-5-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=C(F)C(C=2N=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C)ON=2)=C1 RIJNQCHNXCZMKB-UHFFFAOYSA-N 0.000 claims 1
• GUNNUISZJWGLPH-UHFFFAOYSA-N 3-(2-methylphenyl)-5-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=CC=C1C1=NOC(CSC=2N(C(C=3SC=CC=3)=NN=2)C)=N1 GUNNUISZJWGLPH-UHFFFAOYSA-N 0.000 claims 1
• JZRPLPJPWQASHV-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2N=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)ON=2)=C1 JZRPLPJPWQASHV-UHFFFAOYSA-N 0.000 claims 1
• UXFFNAMXSRIODG-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(ON=1)=NC=1C1=CC=CC(Cl)=C1 UXFFNAMXSRIODG-UHFFFAOYSA-N 0.000 claims 1
• FNLOIGQULBNMQP-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2-oxazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(ON=1)=CC=1C1=CC=CC(Cl)=C1 FNLOIGQULBNMQP-UHFFFAOYSA-N 0.000 claims 1
• QFTBNUNXKAXLBR-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1SCC(ON=1)=NC=1C1=CC=CC(Cl)=C1 QFTBNUNXKAXLBR-UHFFFAOYSA-N 0.000 claims 1
• BZBIEHOOZOUBAR-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(ON=1)=NC=1C1=CC=CC(Cl)=C1 BZBIEHOOZOUBAR-UHFFFAOYSA-N 0.000 claims 1
• WSPTYMZKDVUCBU-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[1-(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)-2-methylpropan-2-yl]-1,2,4-oxadiazole Chemical compound N=1C(C=2C=C(Cl)C=CC=2)=NOC=1C(C)(C)CC(N1C2CC2)=NN=C1C1=CC=NC=C1 WSPTYMZKDVUCBU-UHFFFAOYSA-N 0.000 claims 1
• KUYCYNUMZRIFDV-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[1-(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)propan-2-yl]-1,2,4-oxadiazole Chemical compound N=1C(C=2C=C(Cl)C=CC=2)=NOC=1C(C)CC(N1C2CC2)=NN=C1C1=CC=NC=C1 KUYCYNUMZRIFDV-UHFFFAOYSA-N 0.000 claims 1
• ZJIMPQCIJQCMQE-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[1-(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)propan-2-yl]-1,2,4-oxadiazole Chemical compound N=1C(C=2C=C(Cl)C=CC=2)=NOC=1C(C)CC(N1C)=NN=C1C1=CC=NC=C1 ZJIMPQCIJQCMQE-UHFFFAOYSA-N 0.000 claims 1
• NOJWPQNURDKXMO-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[1-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)oxy]ethyl]-1,2-oxazole Chemical compound C=1C(C=2C=C(Cl)C=CC=2)=NOC=1C(C)OC(N1C)=NN=C1C1=CC=NC=C1 NOJWPQNURDKXMO-UHFFFAOYSA-N 0.000 claims 1
• HTWHUFJONAEYKY-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[1-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1C(C=2C=C(Cl)C=CC=2)=NOC=1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 HTWHUFJONAEYKY-UHFFFAOYSA-N 0.000 claims 1
• LCTIMOQCBMOIAW-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[2-(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)cyclopropyl]-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2N=C(ON=2)C2C(C2)C=2N(C(C=3C=CN=CC=3)=NN=2)C2CC2)=C1 LCTIMOQCBMOIAW-UHFFFAOYSA-N 0.000 claims 1
• IFMMDQRNCVFTLK-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[2-(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)ethyl]-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2N=C(CCC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)ON=2)=C1 IFMMDQRNCVFTLK-UHFFFAOYSA-N 0.000 claims 1
• NAFIDOLZYHPDSM-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[2-(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1CCC(ON=1)=NC=1C1=CC=CC(Cl)=C1 NAFIDOLZYHPDSM-UHFFFAOYSA-N 0.000 claims 1
• IOUHUSIUZLAMGF-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[2-(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)cyclopropyl]-1,2,4-oxadiazole Chemical compound CN1C(C2C(C2)C=2ON=C(N=2)C=2C=C(Cl)C=CC=2)=NN=C1C1=CC=NC=C1 IOUHUSIUZLAMGF-UHFFFAOYSA-N 0.000 claims 1
• XYLNZHYOJGDSAC-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[2-(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CCC(ON=1)=NC=1C1=CC=CC(Cl)=C1 XYLNZHYOJGDSAC-UHFFFAOYSA-N 0.000 claims 1
• LFDFYNANDJGZCR-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[2-(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1CCC(ON=1)=NC=1C1=CC=CC(Cl)=C1 LFDFYNANDJGZCR-UHFFFAOYSA-N 0.000 claims 1
• RGMYQYGESKXZBN-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[[4-ethyl-5-(methylsulfanylmethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CCN1C(CSC)=NN=C1SCC1=NC(C=2C=C(Cl)C=CC=2)=NO1 RGMYQYGESKXZBN-UHFFFAOYSA-N 0.000 claims 1
• RUCVRCTZWPZUTH-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC=2ON=C(N=2)C=2C=C(Cl)C=CC=2)=N1 RUCVRCTZWPZUTH-UHFFFAOYSA-N 0.000 claims 1
• ACVSTHCPAPIYDN-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[[4-ethyl-5-[(4-methoxyphenoxy)methyl]-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(SCC=2ON=C(N=2)C=2C=C(Cl)C=CC=2)N(CC)C=1COC1=CC=C(OC)C=C1 ACVSTHCPAPIYDN-UHFFFAOYSA-N 0.000 claims 1
• ZBFQBILIYJQZOW-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[[5-(ethoxymethyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CCN1C(COCC)=NN=C1SCC1=NC(C=2C=C(Cl)C=CC=2)=NO1 ZBFQBILIYJQZOW-UHFFFAOYSA-N 0.000 claims 1
• WISWIDXXUHKWMX-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[[5-(furan-2-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(C)C=1SCC(ON=1)=NC=1C1=CC=CC(Cl)=C1 WISWIDXXUHKWMX-UHFFFAOYSA-N 0.000 claims 1
• CQXIJJPPNZKAFD-UHFFFAOYSA-N 3-(3-fluorophenyl)-5-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1SCC(ON=1)=NC=1C1=CC=CC(F)=C1 CQXIJJPPNZKAFD-UHFFFAOYSA-N 0.000 claims 1
• GJCVUPPYXAASGG-UHFFFAOYSA-N 3-(3-methylphenyl)-5-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2N=C(CSC=3N(C(C=4SC=CC=4)=NN=3)C)ON=2)=C1 GJCVUPPYXAASGG-UHFFFAOYSA-N 0.000 claims 1
• ZJMVLSWIGSHZHI-UHFFFAOYSA-N 3-(5-chloro-2-fluorophenyl)-5-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(ON=1)=NC=1C1=CC(Cl)=CC=C1F ZJMVLSWIGSHZHI-UHFFFAOYSA-N 0.000 claims 1
• RXYYCGOGFOINBA-UHFFFAOYSA-N 3-(5-chloro-2-fluorophenyl)-5-[[4-(cyclopropylmethyl)-5-thiophen-2-yl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound FC1=CC=C(Cl)C=C1C1=NOC(CSC=2N(C(C=3SC=CC=3)=NN=2)CC2CC2)=N1 RXYYCGOGFOINBA-UHFFFAOYSA-N 0.000 claims 1
• JCBYWLBIPVXKPC-UHFFFAOYSA-N 3-(5-chloro-2-fluorophenyl)-5-[[4-ethyl-5-(methoxymethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CCN1C(COC)=NN=C1SCC1=NC(C=2C(=CC=C(Cl)C=2)F)=NO1 JCBYWLBIPVXKPC-UHFFFAOYSA-N 0.000 claims 1
• SNMDLRDLKAGDNZ-UHFFFAOYSA-N 3-[(4-benzyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-chlorophenyl)-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)CC=3C=CC=CC=3)N=2)=C1 SNMDLRDLKAGDNZ-UHFFFAOYSA-N 0.000 claims 1
• ZYOFGBAKTWEHNT-UHFFFAOYSA-N 3-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(2,5-difluorophenyl)-1,2,4-oxadiazole Chemical compound FC1=CC=C(F)C(C=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=2)=C1 ZYOFGBAKTWEHNT-UHFFFAOYSA-N 0.000 claims 1
• SVAIDTVRJMDBHH-UHFFFAOYSA-N 3-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,2,4-oxadiazole Chemical compound CC1=CC=C(F)C(C=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=2)=C1 SVAIDTVRJMDBHH-UHFFFAOYSA-N 0.000 claims 1
• IHCOSKDYZAGVTK-UHFFFAOYSA-N 3-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=2)=C1 IHCOSKDYZAGVTK-UHFFFAOYSA-N 0.000 claims 1
• LCFYKTWHSMUQFI-UHFFFAOYSA-N 3-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C)=CC=C1F LCFYKTWHSMUQFI-UHFFFAOYSA-N 0.000 claims 1
• LMFGNMOASRUESG-UHFFFAOYSA-N 3-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(C)=C1 LMFGNMOASRUESG-UHFFFAOYSA-N 0.000 claims 1
• HTPRNZYVTWGLBD-UHFFFAOYSA-N 3-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-phenyl-1,2-oxazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(=NO1)C=C1C1=CC=CC=C1 HTPRNZYVTWGLBD-UHFFFAOYSA-N 0.000 claims 1
• DTAQYOBEWOMNDV-UHFFFAOYSA-N 3-[(4-ethyl-5-pyrimidin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2N=CN=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C)=CC=C1F DTAQYOBEWOMNDV-UHFFFAOYSA-N 0.000 claims 1
• PGIFJCVNLPLFAZ-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-fluorophenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(F)=C1 PGIFJCVNLPLFAZ-UHFFFAOYSA-N 0.000 claims 1
• GLLWNYQMXPZTPQ-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-thiophen-2-yl-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CS1 GLLWNYQMXPZTPQ-UHFFFAOYSA-N 0.000 claims 1
• CVXRHUNISRPCFO-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-thiophen-3-yl-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C=1C=CSC=1 CVXRHUNISRPCFO-UHFFFAOYSA-N 0.000 claims 1
• XVTHWPZTJNHYHV-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-phenyl-1,2-oxazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1SCC(=NO1)C=C1C1=CC=CC=C1 XVTHWPZTJNHYHV-UHFFFAOYSA-N 0.000 claims 1
• IUDYUIPBHQIEPN-UHFFFAOYSA-N 3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-nitrophenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC([N+]([O-])=O)=C1 IUDYUIPBHQIEPN-UHFFFAOYSA-N 0.000 claims 1
• MJANABQYSNCKOD-UHFFFAOYSA-N 3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-thiophen-2-yl-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CS1 MJANABQYSNCKOD-UHFFFAOYSA-N 0.000 claims 1
• UYJHUQQPNAGAHP-UHFFFAOYSA-N 3-[(4-methyl-5-thiophen-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-phenyl-1,2-oxazole Chemical compound N=1N=C(C2=CSC=C2)N(C)C=1SCC(=NO1)C=C1C1=CC=CC=C1 UYJHUQQPNAGAHP-UHFFFAOYSA-N 0.000 claims 1
• XJHOPNAINISQFJ-UHFFFAOYSA-N 3-[(4-methyl-5-thiophen-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-thiophen-3-yl-1,2,4-oxadiazole Chemical compound N=1N=C(C2=CSC=C2)N(C)C=1SCC(N=1)=NOC=1C=1C=CSC=1 XJHOPNAINISQFJ-UHFFFAOYSA-N 0.000 claims 1
• JIJJCAHLKXWPIO-UHFFFAOYSA-N 3-[(5-cyclohexyl-4-methyl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CSC=3N(C(C4CCCCC4)=NN=3)C)N=2)=C1 JIJJCAHLKXWPIO-UHFFFAOYSA-N 0.000 claims 1
• MQUMFIKZVRCOQS-UHFFFAOYSA-N 3-[(5-tert-butyl-4-methyl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CSC=3N(C(=NN=3)C(C)(C)C)C)N=2)=C1 MQUMFIKZVRCOQS-UHFFFAOYSA-N 0.000 claims 1
• WAQWXEICNGCCRK-UHFFFAOYSA-N 3-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-5-(2,5-difluorophenyl)-1,2,4-oxadiazole Chemical compound N=1OC(C=2C(=CC=C(F)C=2)F)=NC=1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 WAQWXEICNGCCRK-UHFFFAOYSA-N 0.000 claims 1
• DVDPTDIRIYOADX-UHFFFAOYSA-N 3-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-5-(2-fluoro-5-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1OC(C=2C(=CC=C(C)C=2)F)=NC=1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 DVDPTDIRIYOADX-UHFFFAOYSA-N 0.000 claims 1
• ZQIDMOGLBZEEIM-UHFFFAOYSA-N 3-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-5-(3-fluorophenyl)-1,2,4-oxadiazole Chemical compound N=1OC(C=2C=C(F)C=CC=2)=NC=1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 ZQIDMOGLBZEEIM-UHFFFAOYSA-N 0.000 claims 1
• DQTFPYFZUBMEDT-UHFFFAOYSA-N 3-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1OC(C=2C=C(C)C=CC=2)=NC=1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 DQTFPYFZUBMEDT-UHFFFAOYSA-N 0.000 claims 1
• OGIZMIONSLCTKT-UHFFFAOYSA-N 3-[1-[[4-(cyclopropylmethyl)-5-pyridin-4-yl-1,2,4-triazol-3-yl]sulfanyl]ethyl]-5-(2-fluoro-5-methylphenyl)-1,2-oxazole Chemical compound C1=C(C=2C(=CC=C(C)C=2)F)ON=C1C(C)SC(N1CC2CC2)=NN=C1C1=CC=NC=C1 OGIZMIONSLCTKT-UHFFFAOYSA-N 0.000 claims 1
• SIYIEVRUGAYZHY-UHFFFAOYSA-N 3-[1-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-5-(2-fluoro-5-methylphenyl)-1,2-oxazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SC(C)C(=NO1)C=C1C1=CC(C)=CC=C1F SIYIEVRUGAYZHY-UHFFFAOYSA-N 0.000 claims 1
• PBPPFOCDCUHKMZ-UHFFFAOYSA-N 3-[3-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazol-5-yl]-4-fluorobenzonitrile Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C#N)=CC=C1F PBPPFOCDCUHKMZ-UHFFFAOYSA-N 0.000 claims 1
• VVRIILSXUCXWNR-UHFFFAOYSA-N 3-[3-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound N=1N=C(C=2C=NC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(C#N)=C1 VVRIILSXUCXWNR-UHFFFAOYSA-N 0.000 claims 1
• GEEYWQSZCYHWSK-UHFFFAOYSA-N 3-[3-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound N=1OC(C=2C=C(C=CC=2)C#N)=NC=1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 GEEYWQSZCYHWSK-UHFFFAOYSA-N 0.000 claims 1
• DLUHXUCDPDOJHF-UHFFFAOYSA-N 3-[3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazol-5-yl]-4-fluorobenzonitrile Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C#N)=CC=C1F DLUHXUCDPDOJHF-UHFFFAOYSA-N 0.000 claims 1
• GNTZEZVCXPKVKD-UHFFFAOYSA-N 3-[3-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC=2N=C(ON=2)C=2C=C(C=CC=2)C#N)=N1 GNTZEZVCXPKVKD-UHFFFAOYSA-N 0.000 claims 1
• AZNZAOBELWKZHL-UHFFFAOYSA-N 3-[3-[[4-methyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound N1=C(C(F)(F)F)N(C)C(SCC=2N=C(ON=2)C=2C=C(C=CC=2)C#N)=N1 AZNZAOBELWKZHL-UHFFFAOYSA-N 0.000 claims 1
• STQBZQOSJUYHTL-UHFFFAOYSA-N 3-[5-[(1-methyl-5-thiophen-2-ylimidazol-2-yl)sulfanylmethyl]-1,2,4-oxadiazol-3-yl]benzonitrile Chemical compound N=1C=C(C=2SC=CC=2)N(C)C=1SCC(ON=1)=NC=1C1=CC=CC(C#N)=C1 STQBZQOSJUYHTL-UHFFFAOYSA-N 0.000 claims 1
• CRMGZBRRWORXLV-UHFFFAOYSA-N 3-[5-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3,4-oxadiazol-2-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2OC(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)=NN=2)=C1 CRMGZBRRWORXLV-UHFFFAOYSA-N 0.000 claims 1
• RWZZJCSNTLCCDO-UHFFFAOYSA-N 3-[5-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3,4-oxadiazol-2-yl]benzonitrile Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1SCC(O1)=NN=C1C1=CC=CC(C#N)=C1 RWZZJCSNTLCCDO-UHFFFAOYSA-N 0.000 claims 1
• BFRGHHKUZKLBQA-UHFFFAOYSA-N 3-[5-[2-[5-(3-aminophenyl)-1,3,4-oxadiazol-2-yl]ethyl]-1,3,4-oxadiazol-2-yl]aniline Chemical compound NC1=CC=CC(C=2OC(CCC=3OC(=NN=3)C=3C=C(N)C=CC=3)=NN=2)=C1 BFRGHHKUZKLBQA-UHFFFAOYSA-N 0.000 claims 1
• HWOJYUHKDNSDDO-UHFFFAOYSA-N 3-[5-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazol-3-yl]benzonitrile Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(ON=1)=NC=1C1=CC=CC(C#N)=C1 HWOJYUHKDNSDDO-UHFFFAOYSA-N 0.000 claims 1
• AMNDZVBPKAIDOO-UHFFFAOYSA-N 3-[5-[[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]methylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]benzonitrile Chemical compound N=1N=C(C=2C=C(C=CC=2)C#N)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 AMNDZVBPKAIDOO-UHFFFAOYSA-N 0.000 claims 1
• QHRXUELISNBICD-UHFFFAOYSA-N 3-[[4-ethyl-5-(4-methylphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(2-methylpyridin-4-yl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CC(C)=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=NC(C)=C1 QHRXUELISNBICD-UHFFFAOYSA-N 0.000 claims 1
• PVKPORQZIUVEPY-UHFFFAOYSA-N 3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(4-methylthiophen-2-yl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C)=CS1 PVKPORQZIUVEPY-UHFFFAOYSA-N 0.000 claims 1
• FZTZVZJUZIFHLA-UHFFFAOYSA-N 3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-thiophen-3-yl-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C=1C=CSC=1 FZTZVZJUZIFHLA-UHFFFAOYSA-N 0.000 claims 1
• HPEAXFXUBSWABK-UHFFFAOYSA-N 3-[[4-ethyl-5-(furan-3-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C2=COC=C2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C)=CC=C1F HPEAXFXUBSWABK-UHFFFAOYSA-N 0.000 claims 1
• OREMJJAOKOEIFU-UHFFFAOYSA-N 3-[[4-ethyl-5-(methoxymethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound CCN1C(COC)=NN=C1SCC1=NOC(C=2C=C(C)C=CC=2)=N1 OREMJJAOKOEIFU-UHFFFAOYSA-N 0.000 claims 1
• ARXYFZYKBCCUMR-UHFFFAOYSA-N 3-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-methoxyphenyl)-1,2,4-oxadiazole Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC=2N=C(ON=2)C=2C=C(OC)C=CC=2)=N1 ARXYFZYKBCCUMR-UHFFFAOYSA-N 0.000 claims 1
• DHCHFMGRXAWVOG-UHFFFAOYSA-N 3-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-thiophen-2-yl-1,2,4-oxadiazole Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC=2N=C(ON=2)C=2SC=CC=2)=N1 DHCHFMGRXAWVOG-UHFFFAOYSA-N 0.000 claims 1
• JUGSSLMMDKKBIJ-UHFFFAOYSA-N 3-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-thiophen-3-yl-1,2-oxazole Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC2=NOC(=C2)C2=CSC=C2)=N1 JUGSSLMMDKKBIJ-UHFFFAOYSA-N 0.000 claims 1
• PRVXOHJIVSNPRK-UHFFFAOYSA-N 3-[[5-(1,3-benzodioxol-5-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-chlorophenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 PRVXOHJIVSNPRK-UHFFFAOYSA-N 0.000 claims 1
• BADPRUOGQDHEKU-UHFFFAOYSA-N 3-[[5-(1-benzothiophen-2-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-chlorophenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC3=CC=CC=C3C=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 BADPRUOGQDHEKU-UHFFFAOYSA-N 0.000 claims 1
• FIEJUAQHJUFAMD-UHFFFAOYSA-N 3-[[5-(2-chloro-6-methoxypyridin-4-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-chlorophenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C(OC)N=C(Cl)C=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 FIEJUAQHJUFAMD-UHFFFAOYSA-N 0.000 claims 1
• VQPQVMZZQPQVEG-UHFFFAOYSA-N 3-[[5-(2-chloro-6-methylpyridin-4-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-chlorophenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C(Cl)N=C(C)C=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 VQPQVMZZQPQVEG-UHFFFAOYSA-N 0.000 claims 1
• FBMJLDFTFHPAJZ-UHFFFAOYSA-N 3-[[5-(2-fluoro-5-methylphenyl)-1,2,4-oxadiazol-3-yl]methylsulfanyl]-5-thiophen-2-yl-1,2,4-triazol-4-amine Chemical compound CC1=CC=C(F)C(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)N)N=2)=C1 FBMJLDFTFHPAJZ-UHFFFAOYSA-N 0.000 claims 1
• HYIUYKQLRGVUQH-UHFFFAOYSA-N 3-[[5-(3-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(2-methylpyridin-4-yl)-1,2,4-oxadiazole Chemical compound C1=NC(C)=CC(C=2ON=C(CSC=3N(C(C=4C=C(Cl)C=CC=4)=NN=3)C)N=2)=C1 HYIUYKQLRGVUQH-UHFFFAOYSA-N 0.000 claims 1
• CQNVDDZGEIFOIF-UHFFFAOYSA-N 3-[[5-(3-methylphenyl)-1,2,4-oxadiazol-3-yl]methylsulfanyl]-5-pyridin-4-yl-1,2,4-triazol-4-amine Chemical compound CC1=CC=CC(C=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)N)N=2)=C1 CQNVDDZGEIFOIF-UHFFFAOYSA-N 0.000 claims 1
• VYIOKIZKOCOAPW-UHFFFAOYSA-N 3-[[5-(3-methylphenyl)-1,2,4-oxadiazol-3-yl]methylsulfanyl]-5-thiophen-2-yl-1,2,4-triazol-4-amine Chemical compound CC1=CC=CC(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)N)N=2)=C1 VYIOKIZKOCOAPW-UHFFFAOYSA-N 0.000 claims 1
• FKRGSTYYNOACSK-UHFFFAOYSA-N 3-[[5-(4-methoxyphenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(2-methylpyridin-4-yl)-1,2,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1C(N1C)=NN=C1SCC1=NOC(C=2C=C(C)N=CC=2)=N1 FKRGSTYYNOACSK-UHFFFAOYSA-N 0.000 claims 1
• RKXOELVELJSVAU-UHFFFAOYSA-N 3-[[5-(furan-2-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CSC=3N(C(C=4OC=CC=4)=NN=3)C)N=2)=C1 RKXOELVELJSVAU-UHFFFAOYSA-N 0.000 claims 1
• MVBZWPNNPCWONF-UHFFFAOYSA-N 4-[5-[1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]-1h-pyridin-2-one Chemical compound N=1N=C(C=2C=C(O)N=CC=2)N(CC)C=1SC(C)C(N=1)=NOC=1C1=CC=CC(Cl)=C1 MVBZWPNNPCWONF-UHFFFAOYSA-N 0.000 claims 1
• SJRCCWOQNRYTER-UHFFFAOYSA-N 4-[5-[1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C=CC(O)=CC=2)N(CC)C=1SC(C)C(N=1)=NOC=1C1=CC=CC(Cl)=C1 SJRCCWOQNRYTER-UHFFFAOYSA-N 0.000 claims 1
• RATCIARNOFMTDH-UHFFFAOYSA-N 4-[[5-[[5-(5-chloro-2-fluorophenyl)-1,3,4-oxadiazol-2-yl]methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]methoxy]phenol Chemical compound N=1N=C(SCC=2OC(=NN=2)C=2C(=CC=C(Cl)C=2)F)N(CC)C=1COC1=CC=C(O)C=C1 RATCIARNOFMTDH-UHFFFAOYSA-N 0.000 claims 1
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 1
• RBDPMSWQNRTZMY-UHFFFAOYSA-N 4-chloro-2-[3-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazol-5-yl]phenol Chemical compound OC1=CC=C(Cl)C=C1C1=NC(CSC=2N(C(C=3C=CN=CC=3)=NN=2)C2CC2)=NO1 RBDPMSWQNRTZMY-UHFFFAOYSA-N 0.000 claims 1
• QWSIJYXSIURKJT-UHFFFAOYSA-N 4-chloro-5-(3-chlorophenyl)-3-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2-oxazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(C=1Cl)=NOC=1C1=CC=CC(Cl)=C1 QWSIJYXSIURKJT-UHFFFAOYSA-N 0.000 claims 1
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
• SNDVAXXDGZQBTC-UHFFFAOYSA-N 5-(2,5-dichlorophenyl)-3-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(Cl)=CC=C1Cl SNDVAXXDGZQBTC-UHFFFAOYSA-N 0.000 claims 1
• AHCMYYLLGYTVLO-UHFFFAOYSA-N 5-(2,5-dichlorophenyl)-3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(Cl)=CC=C1Cl AHCMYYLLGYTVLO-UHFFFAOYSA-N 0.000 claims 1
• UXBNBHRSFIXHPY-UHFFFAOYSA-N 5-(2,5-difluorophenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC(F)=CC=C1F UXBNBHRSFIXHPY-UHFFFAOYSA-N 0.000 claims 1
• AREIVJHZVJORNX-UHFFFAOYSA-N 5-(2-chloro-5-methylphenyl)-3-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=C(Cl)C(C=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=2)=C1 AREIVJHZVJORNX-UHFFFAOYSA-N 0.000 claims 1
• ILMKXXLGMPJGRN-UHFFFAOYSA-N 5-(2-chloro-5-methylphenyl)-3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C)=CC=C1Cl ILMKXXLGMPJGRN-UHFFFAOYSA-N 0.000 claims 1
• CHFHZQPWNMXAOU-UHFFFAOYSA-N 5-(2-chloro-5-methylphenyl)-3-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1OC(C=2C(=CC=C(C)C=2)Cl)=NC=1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 CHFHZQPWNMXAOU-UHFFFAOYSA-N 0.000 claims 1
• VSSUYYKDCPRLPT-UHFFFAOYSA-N 5-(2-chloro-5-methylphenyl)-3-[1-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1OC(C=2C(=CC=C(C)C=2)Cl)=NC=1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 VSSUYYKDCPRLPT-UHFFFAOYSA-N 0.000 claims 1
• JWCAHMYPDHKPNA-UHFFFAOYSA-N 5-(2-chloropyridin-4-yl)-3-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=NC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=NC(Cl)=C1 JWCAHMYPDHKPNA-UHFFFAOYSA-N 0.000 claims 1
• QWMBQXKQFQIREI-UHFFFAOYSA-N 5-(2-chloropyridin-4-yl)-3-[[5-(furan-2-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=NC(Cl)=C1 QWMBQXKQFQIREI-UHFFFAOYSA-N 0.000 claims 1
• GINZWEIVRVNTKJ-UHFFFAOYSA-N 5-(2-fluoro-5-methylphenyl)-3-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=C(F)C(C=2ON=C(CSC=3N(C(C=4C=NC=CC=4)=NN=3)C)N=2)=C1 GINZWEIVRVNTKJ-UHFFFAOYSA-N 0.000 claims 1
• LJMFFZPNYPVCPA-UHFFFAOYSA-N 5-(2-fluoro-5-methylphenyl)-3-[(4-propyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CCC)C=1SCC(N=1)=NOC=1C1=CC(C)=CC=C1F LJMFFZPNYPVCPA-UHFFFAOYSA-N 0.000 claims 1
• GYBNGASNFVKVRK-UHFFFAOYSA-N 5-(2-fluoro-5-methylphenyl)-3-[1-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1OC(C=2C(=CC=C(C)C=2)F)=NC=1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 GYBNGASNFVKVRK-UHFFFAOYSA-N 0.000 claims 1
• LMHKLLCITQOYOY-UHFFFAOYSA-N 5-(2-fluoro-5-methylphenyl)-3-[[5-thiophen-2-yl-4-(2,2,2-trifluoroethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=C(F)C(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)CC(F)(F)F)N=2)=C1 LMHKLLCITQOYOY-UHFFFAOYSA-N 0.000 claims 1
• GYHBACOKZTUIAH-UHFFFAOYSA-N 5-(3-bromophenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Br)=C1 GYHBACOKZTUIAH-UHFFFAOYSA-N 0.000 claims 1
• NHUYKHUKVXFOPE-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)methyl]-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2ON=C(CC3C=4N(C(=NN=4)C=4C=CN=CC=4)CCC3)N=2)=C1 NHUYKHUKVXFOPE-UHFFFAOYSA-N 0.000 claims 1
• FNMQZPTVJGZDPQ-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(3-thiophen-2-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)methyl]-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2ON=C(CC3C=4N(C(=NN=4)C=4SC=CC=4)CCC3)N=2)=C1 FNMQZPTVJGZDPQ-UHFFFAOYSA-N 0.000 claims 1
• AOUWEWZXPUGKLU-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=2)=C1 AOUWEWZXPUGKLU-UHFFFAOYSA-N 0.000 claims 1
• OGAVRMARRNBDRE-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2-oxazole Chemical compound ClC1=CC=CC(C=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)C=2)=C1 OGAVRMARRNBDRE-UHFFFAOYSA-N 0.000 claims 1
• HORQHMZJONTVQS-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-cyclopropyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)C3CC3)N=2)=C1 HORQHMZJONTVQS-UHFFFAOYSA-N 0.000 claims 1
• ULMGQSKSIBPAHJ-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-4-methyl-1,2-oxazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(C=1C)=NOC=1C1=CC=CC(Cl)=C1 ULMGQSKSIBPAHJ-UHFFFAOYSA-N 0.000 claims 1
• YLWHPAPFZCREJV-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2-oxazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(=NO1)C=C1C1=CC=CC(Cl)=C1 YLWHPAPFZCREJV-UHFFFAOYSA-N 0.000 claims 1
• QNQHIVAERPTGGU-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=NC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 QNQHIVAERPTGGU-UHFFFAOYSA-N 0.000 claims 1
• PDKOTUJWDUYHBB-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 PDKOTUJWDUYHBB-UHFFFAOYSA-N 0.000 claims 1
• SZUCSNVBBXGZNK-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 SZUCSNVBBXGZNK-UHFFFAOYSA-N 0.000 claims 1
• DFJCTIBOGACAJC-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfinylmethyl]-1,2,4-oxadiazole Chemical compound CN1C(C=2SC=CC=2)=NN=C1S(=O)CC(N=1)=NOC=1C1=CC=CC(Cl)=C1 DFJCTIBOGACAJC-UHFFFAOYSA-N 0.000 claims 1
• CHCUBACSMKMDSF-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfonylmethyl]-1,2,4-oxadiazole Chemical compound CN1C(C=2SC=CC=2)=NN=C1S(=O)(=O)CC(N=1)=NOC=1C1=CC=CC(Cl)=C1 CHCUBACSMKMDSF-UHFFFAOYSA-N 0.000 claims 1
• NLEPIJCFSHIKFA-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)propan-2-yl]-1,2,4-oxadiazole Chemical compound N=1OC(C=2C=C(Cl)C=CC=2)=NC=1C(C)CC(N1C)=NN=C1C1=CC=NC=C1 NLEPIJCFSHIKFA-UHFFFAOYSA-N 0.000 claims 1
• MREUDIQEJJYDBU-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[(4-cyclopropyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)oxy]ethyl]-1,2,4-oxadiazole Chemical compound N=1OC(C=2C=C(Cl)C=CC=2)=NC=1C(C)OC(N1C2CC2)=NN=C1C1=CC=CN=C1 MREUDIQEJJYDBU-UHFFFAOYSA-N 0.000 claims 1
• UMFDBZZEMJYCGY-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[(4-cyclopropyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1OC(C=2C=C(Cl)C=CC=2)=NC=1C(C)SC(N1C2CC2)=NN=C1C1=CC=CN=C1 UMFDBZZEMJYCGY-UHFFFAOYSA-N 0.000 claims 1
• WLKBRYNLHQMHLV-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1OC(C=2C=C(Cl)C=CC=2)=NC=1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 WLKBRYNLHQMHLV-UHFFFAOYSA-N 0.000 claims 1
• NLPRSLMSDZRSRU-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[(4-ethyl-5-pyridazin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=NN=CC=2)N(CC)C=1SC(C)C(N=1)=NOC=1C1=CC=CC(Cl)=C1 NLPRSLMSDZRSRU-UHFFFAOYSA-N 0.000 claims 1
• LBVXPHBWWIWTCB-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SC(C)C(N=1)=NOC=1C1=CC=CC(Cl)=C1 LBVXPHBWWIWTCB-UHFFFAOYSA-N 0.000 claims 1
• AUNHYASFFYNRLA-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2-oxazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SC(C)C(=NO1)C=C1C1=CC=CC(Cl)=C1 AUNHYASFFYNRLA-UHFFFAOYSA-N 0.000 claims 1
• UQAZUBDJPBACCB-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SC(C)C(N=1)=NOC=1C1=CC=CC(Cl)=C1 UQAZUBDJPBACCB-UHFFFAOYSA-N 0.000 claims 1
• ZIWYUFSYSIOIIJ-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1OC(C=2C=C(Cl)C=CC=2)=NC=1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 ZIWYUFSYSIOIIJ-UHFFFAOYSA-N 0.000 claims 1
• MTRXCIBDHOSCBZ-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1OC(C=2C=C(Cl)C=CC=2)=NC=1C(C)SC(N1C)=NN=C1C1=CC=CS1 MTRXCIBDHOSCBZ-UHFFFAOYSA-N 0.000 claims 1
• JCQBSTFDNLGNJD-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[[4-ethyl-5-(5-methoxypyrimidin-2-yl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2N=CC(OC)=CN=2)N(CC)C=1SC(C)C(N=1)=NOC=1C1=CC=CC(Cl)=C1 JCQBSTFDNLGNJD-UHFFFAOYSA-N 0.000 claims 1
• AIUOJNMQGVZQRK-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[[4-ethyl-5-(6-methoxypyridazin-3-yl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2N=NC(OC)=CC=2)N(CC)C=1SC(C)C(N=1)=NOC=1C1=CC=CC(Cl)=C1 AIUOJNMQGVZQRK-UHFFFAOYSA-N 0.000 claims 1
• PZUQKKBDVNOHDA-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[[4-ethyl-5-(6-methoxypyridin-3-yl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=NC(OC)=CC=2)N(CC)C=1SC(C)C(N=1)=NOC=1C1=CC=CC(Cl)=C1 PZUQKKBDVNOHDA-UHFFFAOYSA-N 0.000 claims 1
• BZTHTOLHSIFKKD-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[[4-ethyl-5-(pyridin-4-ylmethyl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(SC(C)C=2N=C(ON=2)C=2C=C(Cl)C=CC=2)N(CC)C=1CC1=CC=NC=C1 BZTHTOLHSIFKKD-UHFFFAOYSA-N 0.000 claims 1
• XYIRWYTVBNVWKW-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[[5-(4-methoxyphenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1C(N1C)=NN=C1SC(C)C1=NOC(C=2C=C(Cl)C=CC=2)=N1 XYIRWYTVBNVWKW-UHFFFAOYSA-N 0.000 claims 1
• CIRNTNBDCRCSLH-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-(furan-2-ylmethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2ON=C(CSC=3N(C=NN=3)CC=3OC=CC=3)N=2)=C1 CIRNTNBDCRCSLH-UHFFFAOYSA-N 0.000 claims 1
• MDJSXQHWRIZADP-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-(furan-2-ylmethyl)-5-pyridin-3-yl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2ON=C(CSC=3N(C(C=4C=NC=CC=4)=NN=3)CC=3OC=CC=3)N=2)=C1 MDJSXQHWRIZADP-UHFFFAOYSA-N 0.000 claims 1
• NTLNUGLBJQDOMN-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-(furan-2-ylmethyl)-5-pyridin-4-yl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)CC=3OC=CC=3)N=2)=C1 NTLNUGLBJQDOMN-UHFFFAOYSA-N 0.000 claims 1
• NQXMGABOPGEKOK-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-cyclopropyl-5-[(4-methoxyphenoxy)methyl]-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1OCC(N1C2CC2)=NN=C1SCC1=NOC(C=2C=C(Cl)C=CC=2)=N1 NQXMGABOPGEKOK-UHFFFAOYSA-N 0.000 claims 1
• KAWIIPXPJCVOJH-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(1-methylimidazol-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2N(C=CN=2)C)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 KAWIIPXPJCVOJH-UHFFFAOYSA-N 0.000 claims 1
• LUUFWSHXKICXOW-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(3-fluorophenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C(F)C=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 LUUFWSHXKICXOW-UHFFFAOYSA-N 0.000 claims 1
• VSNLCUNDVTZKFZ-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(3-methylimidazol-4-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2N(C=NC=2)C)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 VSNLCUNDVTZKFZ-UHFFFAOYSA-N 0.000 claims 1
• IJWYSMUQXXTJBR-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(3-methylphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C(C)C=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 IJWYSMUQXXTJBR-UHFFFAOYSA-N 0.000 claims 1
• XLAILDSOAQVLPD-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(3-nitrophenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C(C=CC=2)[N+]([O-])=O)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 XLAILDSOAQVLPD-UHFFFAOYSA-N 0.000 claims 1
• FZZRQPLRRMSIOP-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 FZZRQPLRRMSIOP-UHFFFAOYSA-N 0.000 claims 1
• ZAIAAFUTZQAARJ-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(5-methylthiophen-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 ZAIAAFUTZQAARJ-UHFFFAOYSA-N 0.000 claims 1
• DRCOBAWAQQHKJT-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 DRCOBAWAQQHKJT-UHFFFAOYSA-N 0.000 claims 1
• ZYDKXNXTAKAFBS-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC=2N=C(ON=2)C=2C=C(Cl)C=CC=2)=N1 ZYDKXNXTAKAFBS-UHFFFAOYSA-N 0.000 claims 1
• UQDZOTGIYXZRSA-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(2,6-difluorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C(=CC=CC=2F)F)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 UQDZOTGIYXZRSA-UHFFFAOYSA-N 0.000 claims 1
• ZXXYMPAIPQZVCN-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(2-chloropyridin-4-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C(Cl)N=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 ZXXYMPAIPQZVCN-UHFFFAOYSA-N 0.000 claims 1
• IETQFCPBHGEOGR-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(2-fluoro-5-methylphenyl)-4-(furan-2-ylmethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=C(F)C(C=2N(C(SCC=3N=C(ON=3)C=3C=C(Cl)C=CC=3)=NN=2)CC=2OC=CC=2)=C1 IETQFCPBHGEOGR-UHFFFAOYSA-N 0.000 claims 1
• JEAQZDWCHHVHRO-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(3,5-difluorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C(F)C=C(F)C=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 JEAQZDWCHHVHRO-UHFFFAOYSA-N 0.000 claims 1
• GAZHEXWZCDVJTL-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(3-chlorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C(Cl)C=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 GAZHEXWZCDVJTL-UHFFFAOYSA-N 0.000 claims 1
• WZYPJCJLMOBROL-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(4-chlorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 WZYPJCJLMOBROL-UHFFFAOYSA-N 0.000 claims 1
• PDKBAGLNXMCSMC-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(4-fluorophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CC(F)=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 PDKBAGLNXMCSMC-UHFFFAOYSA-N 0.000 claims 1
• MASGDNDSEABKTH-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(furan-2-yl)-4-(2-methylpropyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC(C)C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 MASGDNDSEABKTH-UHFFFAOYSA-N 0.000 claims 1
• MJHHAVHSBVGCTR-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(furan-2-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 MJHHAVHSBVGCTR-UHFFFAOYSA-N 0.000 claims 1
• LFSQXUARUANUES-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(furan-3-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C2=COC=C2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 LFSQXUARUANUES-UHFFFAOYSA-N 0.000 claims 1
• BYGFCZMTCNZWJT-UHFFFAOYSA-N 5-(3-cyclopropylphenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C(C=1)=CC=CC=1C1CC1 BYGFCZMTCNZWJT-UHFFFAOYSA-N 0.000 claims 1
• ULBMGQBDSKGLJX-UHFFFAOYSA-N 5-(3-ethenylphenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(C=C)=C1 ULBMGQBDSKGLJX-UHFFFAOYSA-N 0.000 claims 1
• XFDLCNGPBBBHHZ-UHFFFAOYSA-N 5-(3-fluorophenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(F)=C1 XFDLCNGPBBBHHZ-UHFFFAOYSA-N 0.000 claims 1
• MKVMIOFGKYGFCO-UHFFFAOYSA-N 5-(3-methoxyphenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound COC1=CC=CC(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)C)N=2)=C1 MKVMIOFGKYGFCO-UHFFFAOYSA-N 0.000 claims 1
• FRVMWBUVCOGVLE-UHFFFAOYSA-N 5-(3-methoxyphenyl)-3-[1-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound COC1=CC=CC(C=2ON=C(N=2)C(C)SC=2N(C(C=3C=CN=CC=3)=NN=2)C)=C1 FRVMWBUVCOGVLE-UHFFFAOYSA-N 0.000 claims 1
• FGRXAEWNMKMBKB-UHFFFAOYSA-N 5-(3-methylphenyl)-3-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CSC=3N(C(C=4C=NC=CC=4)=NN=3)C)N=2)=C1 FGRXAEWNMKMBKB-UHFFFAOYSA-N 0.000 claims 1
• VAGLSMGLUAQQBZ-UHFFFAOYSA-N 5-(3-methylphenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)C)N=2)=C1 VAGLSMGLUAQQBZ-UHFFFAOYSA-N 0.000 claims 1
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