ZA200500886B - "1,2,4" Oxadiazoles as modulators of metabotropic glutamate receptor-5 - Google Patents
"1,2,4" Oxadiazoles as modulators of metabotropic glutamate receptor-5 Download PDFInfo
- 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
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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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- 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
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- 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
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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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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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WO2005077345A1 (fr) | 2004-02-03 | 2005-08-25 | Astrazeneca Ab | Composes pour le traitement de la maladie du reflux gastro-oesophagien |
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US7585881B2 (en) * | 2004-02-18 | 2009-09-08 | Astrazeneca Ab | Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
AR058807A1 (es) * | 2005-09-29 | 2008-02-27 | Astrazeneca Ab | 5-(fenilisoxazoletoxi)-triazol-3-il piridinas sustituidas, para el tratamiento de trastornos mediados por el receptor mglur5 |
-
2003
- 2003-08-08 KR KR1020057002101A patent/KR20050033070A/ko not_active Application Discontinuation
- 2003-08-08 AU AU2003259068A patent/AU2003259068B2/en not_active Ceased
- 2003-08-08 CN CN200910208474A patent/CN101723941A/zh active Pending
- 2003-08-08 AR AR20030102891A patent/AR040847A1/es unknown
- 2003-08-08 IL IL16651003A patent/IL166510A0/xx unknown
- 2003-08-08 US US10/637,012 patent/US20040152699A1/en not_active Abandoned
- 2003-08-08 WO PCT/US2003/024846 patent/WO2004014881A2/fr active Application Filing
- 2003-08-08 EP EP03785036A patent/EP1529045A2/fr not_active Withdrawn
- 2003-08-08 UA UAA200501100A patent/UA87653C2/ru unknown
- 2003-08-08 TW TW092121880A patent/TWI341314B/zh not_active IP Right Cessation
- 2003-08-08 MX MXPA05001594A patent/MXPA05001594A/es active IP Right Grant
- 2003-08-08 CN CNA038238454A patent/CN1894241A/zh active Pending
- 2003-08-08 BR BR0313265-0A patent/BR0313265A/pt not_active Application Discontinuation
- 2003-08-08 RU RU2005106844/04A patent/RU2352568C9/ru not_active IP Right Cessation
- 2003-08-08 PL PL03375256A patent/PL375256A1/xx unknown
- 2003-08-08 JP JP2004527872A patent/JP4637578B2/ja not_active Expired - Fee Related
- 2003-08-08 NZ NZ538225A patent/NZ538225A/en not_active IP Right Cessation
- 2003-08-08 CA CA2494987A patent/CA2494987C/fr not_active Expired - Fee Related
-
2005
- 2005-01-31 ZA ZA200500886A patent/ZA200500886B/en unknown
- 2005-03-09 NO NO20051225A patent/NO20051225L/no unknown
- 2005-03-09 IS IS7733A patent/IS7733A/is unknown
- 2005-11-14 US US11/274,611 patent/US7456200B2/en not_active Expired - Fee Related
-
2010
- 2010-06-14 JP JP2010135508A patent/JP2010248214A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
JP2006503009A (ja) | 2006-01-26 |
CA2494987C (fr) | 2012-04-17 |
CN101723941A (zh) | 2010-06-09 |
WO2004014881A3 (fr) | 2004-05-27 |
US20060122397A1 (en) | 2006-06-08 |
JP4637578B2 (ja) | 2011-02-23 |
AR040847A1 (es) | 2005-04-20 |
AU2003259068A1 (en) | 2004-02-25 |
IL166510A0 (en) | 2006-01-15 |
AU2003259068B2 (en) | 2009-07-02 |
IS7733A (is) | 2005-03-09 |
MXPA05001594A (es) | 2005-09-20 |
NO20051225L (no) | 2005-05-09 |
RU2005106844A (ru) | 2005-08-27 |
BR0313265A (pt) | 2005-07-05 |
TWI341314B (en) | 2011-05-01 |
WO2004014881B1 (fr) | 2004-07-15 |
CA2494987A1 (fr) | 2004-02-19 |
TW200413361A (en) | 2004-08-01 |
US20040152699A1 (en) | 2004-08-05 |
RU2352568C2 (ru) | 2009-04-20 |
UA87653C2 (en) | 2009-08-10 |
CN1894241A (zh) | 2007-01-10 |
RU2352568C9 (ru) | 2009-06-27 |
KR20050033070A (ko) | 2005-04-08 |
PL375256A1 (en) | 2005-11-28 |
NZ538225A (en) | 2008-05-30 |
JP2010248214A (ja) | 2010-11-04 |
EP1529045A2 (fr) | 2005-05-11 |
US7456200B2 (en) | 2008-11-25 |
WO2004014881A2 (fr) | 2004-02-19 |
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