RU2352568C9 - [1,2,4]оксадиазолы (варианты), способ их получения, фармацевтическая композиция и способ ингибирования активации метаботропных глютаматных рецепторов-5 - Google Patents

Info

Publication number

RU2352568C9

RU2352568C9 RU2005106844/04A RU2005106844A RU2352568C9 RU 2352568 C9 RU2352568 C9 RU 2352568C9 RU 2005106844/04 A RU2005106844/04 A RU 2005106844/04A RU 2005106844 A RU2005106844 A RU 2005106844A RU 2352568 C9 RU2352568 C9 RU 2352568C9

Authority

RU

Russia

Prior art keywords

triazol

ylsulfanylmethyl

oxadiazol

ethyl

oxadiazole

Prior art date

2002-08-09

Links

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims abstract 5
• 230000004913 activation Effects 0.000 title claims abstract 3
• 230000002401 inhibitory effect Effects 0.000 title claims abstract 3
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 3
• BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical class C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 title claims 2
• 102000016193 Metabotropic glutamate receptors Human genes 0.000 title 1
• 108010010914 Metabotropic glutamate receptors Proteins 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract 25
• 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims abstract 5
• 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims abstract 5
• 150000003839 salts Chemical class 0.000 claims abstract 4
• 239000000126 substance Substances 0.000 claims abstract 3
• 230000002265 prevention Effects 0.000 claims abstract 2
• 102000005962 receptors Human genes 0.000 claims abstract 2
• 108020003175 receptors Proteins 0.000 claims abstract 2
• -1 tetrahydrotriazolopyridyl Chemical group 0.000 claims 140
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 49
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 44
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 24
• 125000000217 alkyl group Chemical group 0.000 claims 19
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 11
• 229910052739 hydrogen Inorganic materials 0.000 claims 9
• 239000001257 hydrogen Substances 0.000 claims 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
• 229910052799 carbon Inorganic materials 0.000 claims 7
• 125000002541 furyl group Chemical group 0.000 claims 6
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
• 229910052736 halogen Inorganic materials 0.000 claims 5
• 229910052757 nitrogen Inorganic materials 0.000 claims 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 4
• 150000002367 halogens Chemical class 0.000 claims 4
• 150000002431 hydrogen Chemical class 0.000 claims 4
• TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
• 229910052794 bromium Inorganic materials 0.000 claims 3
• 229910052801 chlorine Inorganic materials 0.000 claims 3
• 239000000460 chlorine Chemical group 0.000 claims 3
• 125000004802 cyanophenyl group Chemical group 0.000 claims 3
• 125000004076 pyridyl group Chemical group 0.000 claims 3
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
• 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 2
• 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 2
• 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 2
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
• 125000004432 carbon atom Chemical group C* 0.000 claims 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
• 125000000335 thiazolyl group Chemical group 0.000 claims 2
• 125000001544 thienyl group Chemical group 0.000 claims 2
• OTTDACCGWJLVEG-SFHVURJKSA-N (1s)-1-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]-2-(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)-n,n-dimethylethanamine Chemical compound C([C@H](N(C)C)C=1ON=C(N=1)C=1C=C(Cl)C=CC=1)C(N1C2CC2)=NN=C1C1=CC=NC=C1 OTTDACCGWJLVEG-SFHVURJKSA-N 0.000 claims 1
• ILTQKUCGOBSWAK-INIZCTEOSA-N (1s)-1-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]-2-(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)ethanamine Chemical compound C([C@H](N)C=1ON=C(N=1)C=1C=C(Cl)C=CC=1)C(N1C2CC2)=NN=C1C1=CC=NC=C1 ILTQKUCGOBSWAK-INIZCTEOSA-N 0.000 claims 1
• 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 1
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
• MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
• VHGWFMVDIQOLMO-UHFFFAOYSA-N 2-(2-fluoro-5-methylphenyl)-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(C)C=2)F)OC=1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 VHGWFMVDIQOLMO-UHFFFAOYSA-N 0.000 claims 1
• WAXKGJSNMDMVSF-UHFFFAOYSA-N 2-(2-fluoro-5-methylphenyl)-5-[1-[[4-methyl-5-(2-methyl-1,3-thiazol-4-yl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C(=CC=C(C)C=2)F)OC=1C(C)SC(N1C)=NN=C1C1=CSC(C)=N1 WAXKGJSNMDMVSF-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• FBIPQZPTASPONC-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3,4-oxadiazole Chemical compound ClC1=CC=CC(C=2OC(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)=NN=2)=C1 FBIPQZPTASPONC-UHFFFAOYSA-N 0.000 claims 1
• WOCLAVMTZUFYNA-UHFFFAOYSA-N 2-(3-chlorophenyl)-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=CC(Cl)=C1 WOCLAVMTZUFYNA-UHFFFAOYSA-N 0.000 claims 1
• KBCVRIFRAIKGPZ-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[1-(3-pyridin-4-yl-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidin-8-yl)ethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=C(Cl)C=CC=2)OC=1C(C)N1CCCN2C1=NN=C2C1=CC=NC=C1 KBCVRIFRAIKGPZ-UHFFFAOYSA-N 0.000 claims 1
• HEWWVGWCMRENAG-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[1-(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)propan-2-yl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=C(Cl)C=CC=2)OC=1C(C)CC(N1C2CC2)=NN=C1C1=CC=NC=C1 HEWWVGWCMRENAG-UHFFFAOYSA-N 0.000 claims 1
• XGYVDPKOEIRQRW-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[1-(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)propan-2-yl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=C(Cl)C=CC=2)OC=1C(C)CC(N1C)=NN=C1C1=CC=NC=C1 XGYVDPKOEIRQRW-UHFFFAOYSA-N 0.000 claims 1
• UDLVGCVDJKONMC-UHFFFAOYSA-N 2-(3-chlorophenyl)-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=C(Cl)C=CC=2)OC=1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 UDLVGCVDJKONMC-UHFFFAOYSA-N 0.000 claims 1
• PVEDUYCSQKJFMC-UHFFFAOYSA-N 2-(3-chlorophenyl)-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=CC(Cl)=C1 PVEDUYCSQKJFMC-UHFFFAOYSA-N 0.000 claims 1
• GMWAOBFOOGYGIO-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[1-[(4-methyl-5-pyridin-3-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=CN=C1 GMWAOBFOOGYGIO-UHFFFAOYSA-N 0.000 claims 1
• HJXIESFCFQISSC-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[1-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)oxy]ethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=C(Cl)C=CC=2)OC=1C(C)OC(N1C)=NN=C1C1=CC=NC=C1 HJXIESFCFQISSC-UHFFFAOYSA-N 0.000 claims 1
• SXRQLINHFLFNKF-UHFFFAOYSA-N 2-(3-chlorophenyl)-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=C(Cl)C=CC=2)OC=1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 SXRQLINHFLFNKF-UHFFFAOYSA-N 0.000 claims 1
• NGAWNSDTIGKJEA-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[1-[[4-(cyclopropylmethyl)-5-pyridin-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(N1CC2CC2)=NN=C1C1=CC=NC=C1 NGAWNSDTIGKJEA-UHFFFAOYSA-N 0.000 claims 1
• VWGMJYLWLVFMEE-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[1-[[4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-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=CC(Cl)=C1 VWGMJYLWLVFMEE-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• PBVVTBFCKFAIBN-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[1-[[4-methyl-5-(2-methyl-1,3-thiazol-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=CSC(C)=N1 PBVVTBFCKFAIBN-UHFFFAOYSA-N 0.000 claims 1
• 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
• WPEJKDSVNNGUEX-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[2-[4-cyclopropyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]ethyl]-1,3,4-oxadiazole Chemical compound ClC1=CC=CC(C=2OC(CCC=3N(C(C=4OC=CC=4)=NN=3)C3CC3)=NN=2)=C1 WPEJKDSVNNGUEX-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• TYAMBRBEDYPBNI-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(O1)=NN=C1C1=CC=CC(Cl)=C1 TYAMBRBEDYPBNI-UHFFFAOYSA-N 0.000 claims 1
• 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
• 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 1
• 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 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
• VRTZOSBFGAMKPD-UHFFFAOYSA-N 2-(3-hydroxypyridin-2-yl)oxypyridin-3-ol Chemical group OC1=CC=CN=C1OC1=NC=CC=C1O VRTZOSBFGAMKPD-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
• 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 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
• 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
• VZBRMXKPWHWTMP-UHFFFAOYSA-N 2-(5-chloro-2-fluorophenyl)-5-[1-[[4-methyl-5-(2-methyl-1,3-thiazol-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=CSC(C)=N1 VZBRMXKPWHWTMP-UHFFFAOYSA-N 0.000 claims 1
• OBOZRSWQXNRAGF-UHFFFAOYSA-N 2-(5-chloro-2-fluorophenyl)-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(Cl)=CC=C1F OBOZRSWQXNRAGF-UHFFFAOYSA-N 0.000 claims 1
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
• SPLYAOBFRFVFNW-UHFFFAOYSA-N 2-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,3,4-oxadiazole Chemical compound CC1=CC=C(F)C(C=2OC(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)=NN=2)=C1 SPLYAOBFRFVFNW-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
• QPCBPSAXDXGGBB-UHFFFAOYSA-N 2-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-methylphenyl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(O1)=NN=C1C1=CC=CC(C)=C1 QPCBPSAXDXGGBB-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
• NTIGTDMCCDACSD-UHFFFAOYSA-N 2-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-5-(2-fluoro-5-methylphenyl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C(=CC=C(C)C=2)F)OC=1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 NTIGTDMCCDACSD-UHFFFAOYSA-N 0.000 claims 1
• LCTZJECYXXQETD-UHFFFAOYSA-N 2-[1-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-5-(2-fluoro-5-methylphenyl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SC(C)C(O1)=NN=C1C1=CC(C)=CC=C1F LCTZJECYXXQETD-UHFFFAOYSA-N 0.000 claims 1
• WVPVRWWYWFLQGI-UHFFFAOYSA-N 2-[1-[[4-(cyclopropylmethyl)-5-pyridin-4-yl-1,2,4-triazol-3-yl]sulfanyl]ethyl]-5-(2-fluoro-5-methylphenyl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C(=CC=C(C)C=2)F)OC=1C(C)SC(N1CC2CC2)=NN=C1C1=CC=NC=C1 WVPVRWWYWFLQGI-UHFFFAOYSA-N 0.000 claims 1
• JGAHBTZYXPSUQZ-UHFFFAOYSA-N 2-[3-[[5-(2-fluoro-5-methylphenyl)-1,2,4-oxadiazol-3-yl]methylsulfanyl]-5-thiophen-2-yl-1,2,4-triazol-4-yl]ethanol Chemical compound CC1=CC=C(F)C(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)CCO)N=2)=C1 JGAHBTZYXPSUQZ-UHFFFAOYSA-N 0.000 claims 1
• BZYDMKFOJCIZET-UHFFFAOYSA-N 2-[[4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC(O1)=NN=C1C1=CC(C)=CC=C1F BZYDMKFOJCIZET-UHFFFAOYSA-N 0.000 claims 1
• MQRDWRRONQXYAR-UHFFFAOYSA-N 2-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(O1)=NN=C1C1=CC(C)=CC=C1F MQRDWRRONQXYAR-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• AQGQZHXNWYNUEI-UHFFFAOYSA-N 2-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-nitrophenyl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(O1)=NN=C1C1=CC=CC([N+]([O-])=O)=C1 AQGQZHXNWYNUEI-UHFFFAOYSA-N 0.000 claims 1
• OKEHURCMYKPVFW-UHFFFAOYSA-N 2-methoxythiophene Chemical compound COC1=CC=CS1 OKEHURCMYKPVFW-UHFFFAOYSA-N 0.000 claims 1
• XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 claims 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
• 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 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
• KGYHLQAOKQELFE-UHFFFAOYSA-N 3-(2,5-difluorophenyl)-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(F)=CC=C1F KGYHLQAOKQELFE-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
• 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 1
• 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 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
• HCWSVWNFTXWRBB-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(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(ON=1)=NC=1C1=CC=CC(Cl)=C1 HCWSVWNFTXWRBB-UHFFFAOYSA-N 0.000 claims 1
• CDJDIKBSKHLGNM-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(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(ON=1)=CC=1C1=CC=CC(Cl)=C1 CDJDIKBSKHLGNM-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
• IOVFWWMMWXRANZ-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(4-methyl-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(C)C=1SCC(ON=1)=CC=1C1=CC=CC(Cl)=C1 IOVFWWMMWXRANZ-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• 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
• PUNQRVADGAPOIG-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[1-[(4-methyl-5-pyridin-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=CC=N1 PUNQRVADGAPOIG-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
• WEYIFMAOJKNSEB-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[1-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2-oxazole Chemical compound C=1C(C=2C=C(Cl)C=CC=2)=NOC=1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 WEYIFMAOJKNSEB-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• TYPRXHGHKFDCCB-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[2-(4-ethyl-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(CC)C=1CCC(ON=1)=NC=1C1=CC=CC(Cl)=C1 TYPRXHGHKFDCCB-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
• 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 1
• 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 1
• 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 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
• OKAJTSQALMTEOT-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[[4-ethyl-5-[2-(4-methoxyphenyl)ethyl]-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=1CCC1=CC=C(OC)C=C1 OKAJTSQALMTEOT-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
• 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 1
• 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 1
• 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 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
• XKZPJZDBTGZNSP-UHFFFAOYSA-N 3-(5-chloro-2-fluorophenyl)-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(Cl)=CC=C1F XKZPJZDBTGZNSP-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
• 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 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
• IFRXMZDYKDOLRV-UHFFFAOYSA-N 3-[(4-butyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-chlorophenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CCCC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 IFRXMZDYKDOLRV-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
• LTZRGEXIPLJLSP-UHFFFAOYSA-N 3-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-fluorophenyl)-1,2,4-oxadiazole Chemical compound FC1=CC=CC(C=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=2)=C1 LTZRGEXIPLJLSP-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
• KWULHINCAPFNAZ-UHFFFAOYSA-N 3-[(4-ethyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C)=CC=C1F KWULHINCAPFNAZ-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• XFYWPSLQKREFBE-UHFFFAOYSA-N 3-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,2-oxazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(=NO1)C=C1C1=CC(C)=CC=C1F XFYWPSLQKREFBE-UHFFFAOYSA-N 0.000 claims 1
• QIIULGGRAKOWMH-UHFFFAOYSA-N 3-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-fluorophenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(F)=C1 QIIULGGRAKOWMH-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
• PCDCYPGAUUFYFE-UHFFFAOYSA-N 3-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(4-methylthiophen-2-yl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C)=CS1 PCDCYPGAUUFYFE-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
• FHWUSJYVINWQNA-UHFFFAOYSA-N 3-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-thiophen-3-yl-1,2-oxazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC(=NO1)C=C1C=1C=CSC=1 FHWUSJYVINWQNA-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
• DDRAIKHIFSZYGL-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(1H-pyrrol-3-yl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C=1C=CNC=1 DDRAIKHIFSZYGL-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• PXRHBPOSEOROTG-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,2-oxazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(=NO1)C=C1C1=CC(C)=CC=C1F PXRHBPOSEOROTG-UHFFFAOYSA-N 0.000 claims 1
• IJQAYWPOIYMIDO-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(2-methyl-1,3-thiazol-4-yl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CSC(C)=N1 IJQAYWPOIYMIDO-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
• 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 1
• UIQMLSOCBAATRH-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(4-fluorophenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=C(F)C=C1 UIQMLSOCBAATRH-UHFFFAOYSA-N 0.000 claims 1
• WSJSRXYLYCLNPK-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(4-methylthiophen-2-yl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C)=CS1 WSJSRXYLYCLNPK-UHFFFAOYSA-N 0.000 claims 1
• QUYRDBIVNMFNCG-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-phenyl-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC=C1 QUYRDBIVNMFNCG-UHFFFAOYSA-N 0.000 claims 1
• IKROGMPWMKMORF-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-phenyl-1,2-oxazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(=NO1)C=C1C1=CC=CC=C1 IKROGMPWMKMORF-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
• CNLKERHNBLBGJM-UHFFFAOYSA-N 3-[(4-ethyl-5-thiophen-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C2=CSC=C2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C)=CC=C1F CNLKERHNBLBGJM-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• MYGMFVVYMHLAHE-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-thiophen-3-yl-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=NC=CC=2)N(C)C=1SCC(N=1)=NOC=1C=1C=CSC=1 MYGMFVVYMHLAHE-UHFFFAOYSA-N 0.000 claims 1
• LZKVQGBCAJXTIS-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-methylsulfanylphenyl)-1,2,4-oxadiazole Chemical compound CSC1=CC=CC(C=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C)N=2)=C1 LZKVQGBCAJXTIS-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
• ULPVHSHEZLYQTD-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-thiophen-2-yl-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CS1 ULPVHSHEZLYQTD-UHFFFAOYSA-N 0.000 claims 1
• HHWZQZYWLLKPHP-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-thiophen-3-yl-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1SCC(N=1)=NOC=1C=1C=CSC=1 HHWZQZYWLLKPHP-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• XVWUMHLMBUMXRX-UHFFFAOYSA-N 3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-[3-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(OC(F)(F)F)=C1 XVWUMHLMBUMXRX-UHFFFAOYSA-N 0.000 claims 1
• JZWNWNGDZGFMAM-UHFFFAOYSA-N 3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(C(F)(F)F)=C1 JZWNWNGDZGFMAM-UHFFFAOYSA-N 0.000 claims 1
• AOKHJLXQMLNGET-UHFFFAOYSA-N 3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-phenyl-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC=C1 AOKHJLXQMLNGET-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
• WWADJCNLAHLHPZ-UHFFFAOYSA-N 3-[(4-methyl-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(C)C=1SCC(N=1)=NOC=1C=1C=CSC=1 WWADJCNLAHLHPZ-UHFFFAOYSA-N 0.000 claims 1
• MVLCBTCKUCBJCN-UHFFFAOYSA-N 3-[(4-methyl-5-thiophen-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-phenyl-1,2,4-oxadiazole Chemical compound N=1N=C(C2=CSC=C2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC=C1 MVLCBTCKUCBJCN-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
• 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 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
• OEJMUMMEUTUCQA-UHFFFAOYSA-N 3-[(5-cyclopentyl-4-ethyl-1,2,4-triazol-3-yl)sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C2CCCC2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(C)=C1 OEJMUMMEUTUCQA-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
• 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 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
• 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 1
• 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 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
• 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
• XPAVEVSPYDSWOC-UHFFFAOYSA-N 3-[3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazol-5-yl]-4-hydroxybenzonitrile Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C#N)=CC=C1O XPAVEVSPYDSWOC-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
• AENPTRNMFZUFPR-UHFFFAOYSA-N 3-[[4-(furan-2-ylmethyl)-5-thiophen-2-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=4SC=CC=4)=NN=3)CC=3OC=CC=3)N=2)=C1 AENPTRNMFZUFPR-UHFFFAOYSA-N 0.000 claims 1
• OTQOGSMNNBOVAH-UHFFFAOYSA-N 3-[[4-cyclopropyl-5-(furan-2-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=4OC=CC=4)=NN=3)C3CC3)N=2)=C1 OTQOGSMNNBOVAH-UHFFFAOYSA-N 0.000 claims 1
• ZVGGXWGJXOSJPA-UHFFFAOYSA-N 3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC(C)=CC=C1F ZVGGXWGJXOSJPA-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• YZKTZAOIXZZVMU-UHFFFAOYSA-N 3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(C)=C1 YZKTZAOIXZZVMU-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
• ROEQOAMFCILCIH-UHFFFAOYSA-N 3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-phenyl-1,2-oxazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(=NO1)C=C1C1=CC=CC=C1 ROEQOAMFCILCIH-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
• UAHZCZDKCDRSJB-UHFFFAOYSA-N 3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-thiophen-3-yl-1,2-oxazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(=NO1)C=C1C=1C=CSC=1 UAHZCZDKCDRSJB-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
• 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 1
• KHLHLMBFPSXSTR-UHFFFAOYSA-N 3-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(2-fluoro-5-methylphenyl)-1,2,4-oxadiazole Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC=2N=C(ON=2)C=2C(=CC=C(C)C=2)F)=N1 KHLHLMBFPSXSTR-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
• 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 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
• UCPKTKSOCYHCDT-UHFFFAOYSA-N 3-[[4-methyl-5-(2-methyl-1,3-thiazol-4-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound S1C(C)=NC(C=2N(C(SCC=3N=C(ON=3)C=3C=C(C)C=CC=3)=NN=2)C)=C1 UCPKTKSOCYHCDT-UHFFFAOYSA-N 0.000 claims 1
• ZIFVEUPVFTWEMD-UHFFFAOYSA-N 3-[[4-methyl-5-(2-methylpyridin-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=C(C)N=CC=4)=NN=3)C)N=2)=C1 ZIFVEUPVFTWEMD-UHFFFAOYSA-N 0.000 claims 1
• GZHRTJUKCMOOGU-UHFFFAOYSA-N 3-[[4-methyl-5-(4-methylphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound C1=CC(C)=CC=C1C(N1C)=NN=C1SCC1=NOC(C=2C=C(C)C=CC=2)=N1 GZHRTJUKCMOOGU-UHFFFAOYSA-N 0.000 claims 1
• KKEZPYWQLLCKRC-UHFFFAOYSA-N 3-[[4-methyl-5-(5-nitrofuran-2-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=4OC(=CC=4)[N+]([O-])=O)=NN=3)C)N=2)=C1 KKEZPYWQLLCKRC-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
• UKWIJYOQPRRLKZ-UHFFFAOYSA-N 3-[[5-(2,4-dimethyl-1,3-thiazol-5-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-methylphenyl)-1,2,4-oxadiazole Chemical compound S1C(C)=NC(C)=C1C(N1C)=NN=C1SCC1=NOC(C=2C=C(C)C=CC=2)=N1 UKWIJYOQPRRLKZ-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• NTLQESJPLWLPHA-UHFFFAOYSA-N 3-[[5-(4-butoxyphenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-chlorophenyl)-1,2,4-oxadiazole Chemical compound C1=CC(OCCCC)=CC=C1C(N1CC)=NN=C1SCC1=NOC(C=2C=C(Cl)C=CC=2)=N1 NTLQESJPLWLPHA-UHFFFAOYSA-N 0.000 claims 1
• ABARXTKZSFWWCA-UHFFFAOYSA-N 3-[[5-(4-tert-butylphenyl)-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=CC(=CC=4)C(C)(C)C)=NN=3)C)N=2)=C1 ABARXTKZSFWWCA-UHFFFAOYSA-N 0.000 claims 1
• CPKVHKCZJQDHCU-UHFFFAOYSA-N 3-[[5-(5-bromofuran-2-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-5-(3-chlorophenyl)-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC(Br)=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 CPKVHKCZJQDHCU-UHFFFAOYSA-N 0.000 claims 1
• DLVFQTANVDENKH-UHFFFAOYSA-N 3-[[5-(6-chloropyridin-3-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=NC(Cl)=CC=4)=NN=3)C)N=2)=C1 DLVFQTANVDENKH-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
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
• 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 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
• 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 1
• 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 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
• ZUSXQVOXTSIEGA-UHFFFAOYSA-N 4-chloro-5-(3-chlorophenyl)-3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2-oxazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(C=1Cl)=NOC=1C1=CC=CC(Cl)=C1 ZUSXQVOXTSIEGA-UHFFFAOYSA-N 0.000 claims 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
• 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 1
• GZMLPIORLFBNLG-UHFFFAOYSA-N 5-(2,5-dichlorothiophen-3-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=1C=1C=C(Cl)SC=1Cl GZMLPIORLFBNLG-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 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
• OMANTAPHBCGRHO-UHFFFAOYSA-N 5-(2,5-difluorophenyl)-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(F)C=2)F)=NC=1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 OMANTAPHBCGRHO-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 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
• 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 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
• GBAWAQVIENWMAD-UHFFFAOYSA-N 5-(2-fluoro-5-methylphenyl)-3-[(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=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C)N=2)=C1 GBAWAQVIENWMAD-UHFFFAOYSA-N 0.000 claims 1
• UECWYIVGDGWMDC-UHFFFAOYSA-N 5-(2-fluoro-5-methylphenyl)-3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2-oxazole Chemical compound CC1=CC=C(F)C(C=2ON=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C)C=2)=C1 UECWYIVGDGWMDC-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• NBQBCDNOUBHTMA-UHFFFAOYSA-N 5-(2-fluoro-5-methylphenyl)-3-[[5-(furan-2-yl)-4-(2-methoxyethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(CCOC)C=1SCC(N=1)=NOC=1C1=CC(C)=CC=C1F NBQBCDNOUBHTMA-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
• 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 1
• 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 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
• NXWYXIKVKXYDPE-UHFFFAOYSA-N 5-(3-chlorophenyl)-2-[(4-ethyl-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(CC)C=1SCC(O1)=NC=C1C1=CC=CC(Cl)=C1 NXWYXIKVKXYDPE-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 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
• NHMDVEIHROEGHR-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(3-pyridin-4-yl-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidin-8-yl)methyl]-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2ON=C(CN3C=4N(C(=NN=4)C=4C=CN=CC=4)CCC3)N=2)=C1 NHMDVEIHROEGHR-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
• 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
• FUMUDOIBGPCOKG-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-ethyl-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(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 FUMUDOIBGPCOKG-UHFFFAOYSA-N 0.000 claims 1
• SYPUYSSMFKOKHK-UHFFFAOYSA-N 5-(3-chlorophenyl)-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=CC(Cl)=C1 SYPUYSSMFKOKHK-UHFFFAOYSA-N 0.000 claims 1
• LWCYVBWRGPKJNI-UHFFFAOYSA-N 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(=NO1)C=C1C1=CC=CC(Cl)=C1 LWCYVBWRGPKJNI-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
• MEZVCUMAZDIZRD-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)oxymethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1OCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 MEZVCUMAZDIZRD-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• BBQMMLVUCDIDFV-UHFFFAOYSA-N 5-(3-chlorophenyl)-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=CC(Cl)=C1 BBQMMLVUCDIDFV-UHFFFAOYSA-N 0.000 claims 1
• OLOPRNCZPKKCKV-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-hexyl-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(CCCCCC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 OLOPRNCZPKKCKV-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
• OZGHSPUKYJCXBA-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-methyl-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(C)C=1SCC(=NO1)C=C1C1=CC=CC(Cl)=C1 OZGHSPUKYJCXBA-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• FQYXEBULOHXZNV-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2-oxazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(=NO1)C=C1C1=CC=CC(Cl)=C1 FQYXEBULOHXZNV-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
• UDNRYAYKDMOEKJ-UHFFFAOYSA-N 5-(3-chlorophenyl)-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(Cl)=C1 UDNRYAYKDMOEKJ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• XTIKWEBFJZETEW-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-(3-pyridin-4-yl-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidin-8-yl)ethyl]-1,2,4-oxadiazole Chemical compound N=1OC(C=2C=C(Cl)C=CC=2)=NC=1C(C)N1CCCN2C1=NN=C2C1=CC=NC=C1 XTIKWEBFJZETEW-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
• WPDGAVPHRWYSKO-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[(4-ethyl-5-pyrimidin-2-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2N=CC=CN=2)N(CC)C=1SC(C)C(N=1)=NOC=1C1=CC=CC(Cl)=C1 WPDGAVPHRWYSKO-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
• RWDAYHQSKLFZAX-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[[4-ethyl-5-(2-methoxypyridin-4-yl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C(OC)N=CC=2)N(CC)C=1SC(C)C(N=1)=NOC=1C1=CC=CC(Cl)=C1 RWDAYHQSKLFZAX-UHFFFAOYSA-N 0.000 claims 1
• WLXVKCKRIHTHMD-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[[4-ethyl-5-(5-methoxypyridin-2-yl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2N=CC(OC)=CC=2)N(CC)C=1SC(C)C(N=1)=NOC=1C1=CC=CC(Cl)=C1 WLXVKCKRIHTHMD-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
• 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 1
• KFJHAFKCATXJBS-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[[4-ethyl-5-(oxolan-2-yl)-1,2,4-triazol-3-yl]sulfanyl]ethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C2OCCC2)N(CC)C=1SC(C)C(N=1)=NOC=1C1=CC=CC(Cl)=C1 KFJHAFKCATXJBS-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
• 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 1
• MTIWVKOEBCPTOA-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-(2-methoxyethyl)-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(CCOC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 MTIWVKOEBCPTOA-UHFFFAOYSA-N 0.000 claims 1
• VONXISMXLNNAKM-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-(2-methylbutyl)-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)CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 VONXISMXLNNAKM-UHFFFAOYSA-N 0.000 claims 1
• VHZFHKMHJQXVQZ-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-(3-methoxypropyl)-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(CCCOC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 VHZFHKMHJQXVQZ-UHFFFAOYSA-N 0.000 claims 1
• OVSXUQDXWUJTLV-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-(3-methylbutyl)-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(CCC(C)C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 OVSXUQDXWUJTLV-UHFFFAOYSA-N 0.000 claims 1
• NFFPDFPJQQKBCR-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-(3-methylsulfanylpropyl)-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(CCCSC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 NFFPDFPJQQKBCR-UHFFFAOYSA-N 0.000 claims 1
• AOSCUNSWHZTZAH-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-(cyclopropylmethyl)-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)CC3CC3)N=2)=C1 AOSCUNSWHZTZAH-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
• JQIBWMDZHJOPFQ-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-(furan-2-ylmethyl)-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)CC=3OC=CC=3)N=2)=C1 JQIBWMDZHJOPFQ-UHFFFAOYSA-N 0.000 claims 1
• NQBFHLQSNFCCFJ-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-(oxolan-2-ylmethyl)-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)CC3OCCC3)N=2)=C1 NQBFHLQSNFCCFJ-UHFFFAOYSA-N 0.000 claims 1
• UQJNLCQFVDWKDL-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-[(2-fluorophenyl)methyl]-5-thiophen-2-yl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound FC1=CC=CC=C1CN1C(C=2SC=CC=2)=NN=C1SCC1=NOC(C=2C=C(Cl)C=CC=2)=N1 UQJNLCQFVDWKDL-UHFFFAOYSA-N 0.000 claims 1
• TXNQZEUXDKBVQP-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-[(3-fluorophenyl)methyl]-5-thiophen-2-yl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound FC1=CC=CC(CN2C(=NN=C2SCC=2N=C(ON=2)C=2C=C(Cl)C=CC=2)C=2SC=CC=2)=C1 TXNQZEUXDKBVQP-UHFFFAOYSA-N 0.000 claims 1
• SUKWOODDSKGZOD-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-[(3-methylphenyl)methyl]-5-thiophen-2-yl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=CC(CN2C(=NN=C2SCC=2N=C(ON=2)C=2C=C(Cl)C=CC=2)C=2SC=CC=2)=C1 SUKWOODDSKGZOD-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
• SVYVUZLILFSIKY-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(1-methylimidazol-4-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2N=CN(C)C=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 SVYVUZLILFSIKY-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
• PRBVMEPAPNHGEH-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(3-methoxythiophen-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C2=C(C=CS2)OC)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 PRBVMEPAPNHGEH-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
• XEJRLJIVWGEJQH-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(3-methylthiophen-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C2=C(C=CS2)C)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 XEJRLJIVWGEJQH-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
• 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 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
• 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 1
• MHHGJVGTMDSNLI-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(4-methylphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CC(C)=CC=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 MHHGJVGTMDSNLI-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
• CVVGRFYNJCJBES-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-4-methyl-1,2-oxazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(C=1C)=NOC=1C1=CC=CC(Cl)=C1 CVVGRFYNJCJBES-UHFFFAOYSA-N 0.000 claims 1
• QQZQLVQIIIKQGA-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-(methoxymethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CCN1C(COC)=NN=C1SCC1=NOC(C=2C=C(Cl)C=CC=2)=N1 QQZQLVQIIIKQGA-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
• 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 1
• 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 1
• LRNOSYCBYWOHRY-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-ethyl-5-[(4-methylphenoxy)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(C)C=C1 LRNOSYCBYWOHRY-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• YVIYQMUETXGILS-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-methyl-5-(2-methylpyridin-4-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound C1=NC(C)=CC(C=2N(C(SCC=3N=C(ON=3)C=3C=C(Cl)C=CC=3)=NN=2)C)=C1 YVIYQMUETXGILS-UHFFFAOYSA-N 0.000 claims 1
• SOSVNULSJVBHEY-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(2,5-difluorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C(=CC=C(F)C=2)F)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 SOSVNULSJVBHEY-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
• OBERCCWQFQSKEO-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(3,5-dichlorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C(Cl)C=C(Cl)C=2)N(CC)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 OBERCCWQFQSKEO-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
• VTNHDBVBFIEKJJ-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(3-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=C(Cl)C=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 VTNHDBVBFIEKJJ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• LOCMWEAYMRCNKC-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(3-methoxyphenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound COC1=CC=CC(C=2N(C(SCC=3N=C(ON=3)C=3C=C(Cl)C=CC=3)=NN=2)C)=C1 LOCMWEAYMRCNKC-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
• XFZYLJQNTBVTDI-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(4-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(C)C=1SCC(N=1)=NOC=1C1=CC=CC(Cl)=C1 XFZYLJQNTBVTDI-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
• IPRWNFCZLIZOFS-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(4-methoxyphenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1C(N1C)=NN=C1SCC1=NOC(C=2C=C(Cl)C=CC=2)=N1 IPRWNFCZLIZOFS-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
• KQQWLMQXBOFLCP-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-(furan-2-yl)-4-methyl-1,2,4-triazol-3-yl]methyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2OC=CC=2)N(C)C=1CC(N=1)=NOC=1C1=CC=CC(Cl)=C1 KQQWLMQXBOFLCP-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
• ABUFNPJIRZLRRE-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-[(4-methoxyphenoxy)methyl]-4-(oxolan-2-ylmethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1OCC(N1CC2OCCC2)=NN=C1SCC1=NOC(C=2C=C(Cl)C=CC=2)=N1 ABUFNPJIRZLRRE-UHFFFAOYSA-N 0.000 claims 1
• AFYDWXOKTJQUCE-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[5-thiophen-2-yl-4-(thiophen-2-ylmethyl)-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)CC=3SC=CC=3)N=2)=C1 AFYDWXOKTJQUCE-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
• FJDUBBUSPPFLRH-UHFFFAOYSA-N 5-(3-ethylphenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CCC1=CC=CC(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)C)N=2)=C1 FJDUBBUSPPFLRH-UHFFFAOYSA-N 0.000 claims 1
• GJPVLZNEXHASHY-UHFFFAOYSA-N 5-(3-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(F)=CC(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)C)N=2)=C1 GJPVLZNEXHASHY-UHFFFAOYSA-N 0.000 claims 1
• KEGRIXZBFZNJTF-UHFFFAOYSA-N 5-(3-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=CC(F)=C1 KEGRIXZBFZNJTF-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• 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 1
• LSXDNRQAIROIGN-UHFFFAOYSA-N 5-(3-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=C(F)C=CC=2)=NC=1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 LSXDNRQAIROIGN-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• YSSUJUDLYTVELX-UHFFFAOYSA-N 5-(3-methoxyphenyl)-3-[(1-methylimidazo[4,5-b]pyridin-2-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound COC1=CC=CC(C=2ON=C(CSC=3N(C4=CC=CN=C4N=3)C)N=2)=C1 YSSUJUDLYTVELX-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
• KEJIGCLBFZAREA-UHFFFAOYSA-N 5-(3-methoxyphenyl)-3-[1-(1-methylimidazo[4,5-b]pyridin-2-yl)sulfanylethyl]-1,2,4-oxadiazole Chemical compound COC1=CC=CC(C=2ON=C(N=2)C(C)SC=2N(C3=CC=CN=C3N=2)C)=C1 KEJIGCLBFZAREA-UHFFFAOYSA-N 0.000 claims 1
• OLLJGHUOJBUUED-UHFFFAOYSA-N 5-(3-methylphenyl)-3-[(4-methyl-5-pyridin-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=4N=CC=CC=4)=NN=3)C)N=2)=C1 OLLJGHUOJBUUED-UHFFFAOYSA-N 0.000 claims 1
• DCKJDNUYSJWBQZ-UHFFFAOYSA-N 5-(3-methylphenyl)-3-[(4-methyl-5-pyridin-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=4C=CN=CC=4)=NN=3)C)N=2)=C1 DCKJDNUYSJWBQZ-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
• 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 1
• VPLDUFNMXAWFMH-UHFFFAOYSA-N 5-(3-methylphenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfonylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CS(=O)(=O)C=3N(C(C=4SC=CC=4)=NN=3)C)N=2)=C1 VPLDUFNMXAWFMH-UHFFFAOYSA-N 0.000 claims 1
• LZYVEFBDBOICTE-UHFFFAOYSA-N 5-(3-methylphenyl)-3-[(4-methyl-5-thiophen-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CSC=3N(C(C4=CSC=C4)=NN=3)C)N=2)=C1 LZYVEFBDBOICTE-UHFFFAOYSA-N 0.000 claims 1
• VZLDANZSZQMFKW-UHFFFAOYSA-N 5-(3-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=C(C)C=CC=2)=NC=1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 VZLDANZSZQMFKW-UHFFFAOYSA-N 0.000 claims 1
• ULAYCILFACEVOO-UHFFFAOYSA-N 5-(3-methylphenyl)-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(C)C=CC=2)=NC=1C(C)SC(N1C)=NN=C1C1=CC=CS1 ULAYCILFACEVOO-UHFFFAOYSA-N 0.000 claims 1
• PAWMLRVRCRGGBZ-UHFFFAOYSA-N 5-(3-methylphenyl)-3-[2-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanyl]propan-2-yl]-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(N=2)C(C)(C)SC=2N(C(C=3SC=CC=3)=NN=2)C)=C1 PAWMLRVRCRGGBZ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• HZMWBWDNNFRJBH-UHFFFAOYSA-N 5-(3-methylsulfanylphenyl)-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CSC1=CC=CC(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)C)N=2)=C1 HZMWBWDNNFRJBH-UHFFFAOYSA-N 0.000 claims 1
• KEFZUEAAGZNOIG-UHFFFAOYSA-N 5-(4-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=C(F)C=C1 KEFZUEAAGZNOIG-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• DLSCCBCZPALTHN-UHFFFAOYSA-N 5-(5-bromo-2-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(Br)=CC=C1F DLSCCBCZPALTHN-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• IFNGRKHGLSYOBK-UHFFFAOYSA-N 5-(5-bromo-2-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(Br)=CC=C1F IFNGRKHGLSYOBK-UHFFFAOYSA-N 0.000 claims 1
• BPPFJZYXXOIXRN-UHFFFAOYSA-N 5-(5-bromo-2-fluorophenyl)-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(Br)=CC=C1F BPPFJZYXXOIXRN-UHFFFAOYSA-N 0.000 claims 1
• VWURPMYVALSHNQ-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-3-[(4-cyclopropyl-5-pyridin-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=3C=CN=CC=3)=NN=2)C2CC2)=NO1 VWURPMYVALSHNQ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• TXHNTJVKTQLLNK-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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=C1F TXHNTJVKTQLLNK-UHFFFAOYSA-N 0.000 claims 1
• LZOUCFFTZXXUKD-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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(=NO1)C=C1C1=CC(Cl)=CC=C1F LZOUCFFTZXXUKD-UHFFFAOYSA-N 0.000 claims 1
• XUQHKLSYADGXDX-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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=C1F XUQHKLSYADGXDX-UHFFFAOYSA-N 0.000 claims 1
• DZPIQQCDPFFWIN-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)oxymethyl]-1,2,4-oxadiazole Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1OCC(N=1)=NOC=1C1=CC(Cl)=CC=C1F DZPIQQCDPFFWIN-UHFFFAOYSA-N 0.000 claims 1
• RUAINULLQLGMJP-UHFFFAOYSA-N 5-(5-chloro-2-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(Cl)=CC=C1F RUAINULLQLGMJP-UHFFFAOYSA-N 0.000 claims 1
• JRMVIKDCCOXLGQ-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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(Cl)=CC=C1F JRMVIKDCCOXLGQ-UHFFFAOYSA-N 0.000 claims 1
• PXGAZMDYHYSWAB-UHFFFAOYSA-N 5-(5-chloro-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(Cl)=CC=C1F PXGAZMDYHYSWAB-UHFFFAOYSA-N 0.000 claims 1
• XYVAORXNBAHGKH-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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(Cl)C=2)F)=NC=1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 XYVAORXNBAHGKH-UHFFFAOYSA-N 0.000 claims 1
• UTHHBMRJHCGEEW-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-3-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]-1,2-oxazole Chemical compound C1=C(C=2C(=CC=C(Cl)C=2)F)ON=C1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 UTHHBMRJHCGEEW-UHFFFAOYSA-N 0.000 claims 1
• CDTYKGCCBRPRLT-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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(Cl)=CC=C1F CDTYKGCCBRPRLT-UHFFFAOYSA-N 0.000 claims 1
• MJYWSVANIUTPEH-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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(Cl)=CC=C1F MJYWSVANIUTPEH-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• BHQYNIIOIZMLOX-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-oxazole Chemical compound C1=C(C=2C(=CC=C(Cl)C=2)F)ON=C1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 BHQYNIIOIZMLOX-UHFFFAOYSA-N 0.000 claims 1
• GXYQIPXYTFIAJY-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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(=CC=C(Cl)C=2)F)=NC=1C(C)SC(N1C)=NN=C1C1=CC=CS1 GXYQIPXYTFIAJY-UHFFFAOYSA-N 0.000 claims 1
• QUZPAUJBNYHMBW-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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(Cl)=CC=C1F QUZPAUJBNYHMBW-UHFFFAOYSA-N 0.000 claims 1
• HROGODRDPFPGMX-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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(=CC=C(Cl)C=2)F)=N1 HROGODRDPFPGMX-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• RGVRMNJDWIZKQM-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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(Cl)=CC=C1F RGVRMNJDWIZKQM-UHFFFAOYSA-N 0.000 claims 1
• IJXPKHNOYKJXBT-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2-oxazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(=NO1)C=C1C1=CC(Cl)=CC=C1F IJXPKHNOYKJXBT-UHFFFAOYSA-N 0.000 claims 1
• ITEQETBMOMLANQ-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-3-[[4-ethyl-5-(methoxymethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CCN1C(COC)=NN=C1SCC1=NOC(C=2C(=CC=C(Cl)C=2)F)=N1 ITEQETBMOMLANQ-UHFFFAOYSA-N 0.000 claims 1
• GTNLJCDYZURCQV-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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(=CC=C(Cl)C=2)F)=N1 GTNLJCDYZURCQV-UHFFFAOYSA-N 0.000 claims 1
• WVHKNISLXRJFNH-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-3-[[4-methyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound N1=C(C(F)(F)F)N(C)C(SCC=2N=C(ON=2)C=2C(=CC=C(Cl)C=2)F)=N1 WVHKNISLXRJFNH-UHFFFAOYSA-N 0.000 claims 1
• FCMIKXTXZXALGJ-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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(Cl)=CC=C1F FCMIKXTXZXALGJ-UHFFFAOYSA-N 0.000 claims 1
• ZTTYHWOAMDGGLI-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-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(Cl)=CC=C1F ZTTYHWOAMDGGLI-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• ACPUGQSSQBEVCO-UHFFFAOYSA-N 5-(5-chlorothiophen-2-yl)-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=C(Cl)S1 ACPUGQSSQBEVCO-UHFFFAOYSA-N 0.000 claims 1
• ZDETWVWDFGVZIX-UHFFFAOYSA-N 5-(5-chlorothiophen-3-yl)-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=CSC(Cl)=C1 ZDETWVWDFGVZIX-UHFFFAOYSA-N 0.000 claims 1
• WMDXRHAMNAJCDK-UHFFFAOYSA-N 5-(5-chlorothiophen-3-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=CSC(Cl)=C1 WMDXRHAMNAJCDK-UHFFFAOYSA-N 0.000 claims 1
• QDZFEHYVVSJAJW-UHFFFAOYSA-N 5-(5-chlorothiophen-3-yl)-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=CSC(Cl)=C1 QDZFEHYVVSJAJW-UHFFFAOYSA-N 0.000 claims 1
• NVBSAASFCDSIIW-UHFFFAOYSA-N 5-(5-chlorothiophen-3-yl)-3-[[4-ethyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2-oxazole Chemical compound N=1N=C(C=2OC=CC=2)N(CC)C=1SCC(=NO1)C=C1C1=CSC(Cl)=C1 NVBSAASFCDSIIW-UHFFFAOYSA-N 0.000 claims 1
• OBMAGGCKSYPNCJ-UHFFFAOYSA-N 5-(5-fluoro-2-methylphenyl)-3-[[4-(furan-2-ylmethyl)-5-thiophen-2-yl-1,2,4-triazol-3-yl]sulfanylmethyl]-1,2,4-oxadiazole Chemical compound CC1=CC=C(F)C=C1C1=NC(CSC=2N(C(C=3SC=CC=3)=NN=2)CC=2OC=CC=2)=NO1 OBMAGGCKSYPNCJ-UHFFFAOYSA-N 0.000 claims 1
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• ZOKCVZDKHOHESK-UHFFFAOYSA-N 5-(furan-3-yl)-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=1C=COC=1 ZOKCVZDKHOHESK-UHFFFAOYSA-N 0.000 claims 1
• GECOSSLMNIMMRT-UHFFFAOYSA-N 5-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-3-thiophen-2-yl-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(ON=1)=NC=1C1=CC=CS1 GECOSSLMNIMMRT-UHFFFAOYSA-N 0.000 claims 1
• FVAHXLCFVRBPTJ-UHFFFAOYSA-N 5-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-3-thiophen-3-yl-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(ON=1)=NC=1C=1C=CSC=1 FVAHXLCFVRBPTJ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
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• ICSCZXJMZHSRIO-UHFFFAOYSA-N 5-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-3-phenyl-1,2,4-oxadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC(ON=1)=NC=1C1=CC=CC=C1 ICSCZXJMZHSRIO-UHFFFAOYSA-N 0.000 claims 1
• MXFCOXNXCAQCDO-UHFFFAOYSA-N 5-[(4-methyl-5-thiophen-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-3-phenyl-1,2,4-oxadiazole Chemical compound N=1N=C(C2=CSC=C2)N(C)C=1SCC(ON=1)=NC=1C1=CC=CC=C1 MXFCOXNXCAQCDO-UHFFFAOYSA-N 0.000 claims 1
• WMGYPIZNFRBQNI-UHFFFAOYSA-N 5-[(4-methyl-5-thiophen-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-3-thiophen-3-yl-1,2,4-oxadiazole Chemical compound N=1N=C(C2=CSC=C2)N(C)C=1SCC(ON=1)=NC=1C=1C=CSC=1 WMGYPIZNFRBQNI-UHFFFAOYSA-N 0.000 claims 1
• YKCAOHODYRHOEV-UHFFFAOYSA-N 5-[(5-bromo-4-methyl-1,2,4-triazol-3-yl)sulfanylmethyl]-3-(3-chlorophenyl)-1,2,4-oxadiazole Chemical compound CN1C(Br)=NN=C1SCC1=NC(C=2C=C(Cl)C=CC=2)=NO1 YKCAOHODYRHOEV-UHFFFAOYSA-N 0.000 claims 1
• GGYHTHVKGJACRO-UHFFFAOYSA-N 5-[3-(difluoromethoxy)phenyl]-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(OC(F)F)=C1 GGYHTHVKGJACRO-UHFFFAOYSA-N 0.000 claims 1
• UWZGWPYARRYJEB-UHFFFAOYSA-N 5-[3-(furan-3-yl)phenyl]-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=1C=1C=COC=1 UWZGWPYARRYJEB-UHFFFAOYSA-N 0.000 claims 1
• KXVRLELRDCWCKH-UHFFFAOYSA-N 5-[3-(methoxymethyl)phenyl]-3-[(4-methyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,2,4-oxadiazole Chemical compound COCC1=CC=CC(C=2ON=C(CSC=3N(C(C=4SC=CC=4)=NN=3)C)N=2)=C1 KXVRLELRDCWCKH-UHFFFAOYSA-N 0.000 claims 1
• BJRIGRMFQWMSJF-UHFFFAOYSA-N 5-[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=NC(O)=CC=2)N(CC)C=1SC(C)C(N=1)=NOC=1C1=CC=CC(Cl)=C1 BJRIGRMFQWMSJF-UHFFFAOYSA-N 0.000 claims 1
• DJGKVBNDRBGOLC-UHFFFAOYSA-N 5-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-3-(3-methoxyphenyl)-1,2,4-oxadiazole Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC=2ON=C(N=2)C=2C=C(OC)C=CC=2)=N1 DJGKVBNDRBGOLC-UHFFFAOYSA-N 0.000 claims 1
• FHZUMSXYPWNPPX-UHFFFAOYSA-N 5-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-3-thiophen-2-yl-1,2,4-oxadiazole Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC=2ON=C(N=2)C=2SC=CC=2)=N1 FHZUMSXYPWNPPX-UHFFFAOYSA-N 0.000 claims 1
• MLDJCKFYLWCFBL-UHFFFAOYSA-N 5-[[4-ethyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]sulfanylmethyl]-3-thiophen-3-yl-1,2,4-oxadiazole Chemical compound N1=C(C(F)(F)F)N(CC)C(SCC=2ON=C(N=2)C2=CSC=C2)=N1 MLDJCKFYLWCFBL-UHFFFAOYSA-N 0.000 claims 1
• FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 1
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
• WWIHYVWCYRQJPX-UHFFFAOYSA-N CN1C(=NN=C1SCC1=NOC(=N1)C=1C=C(C=CC1)C)C=1C=NC=CC1.N1=CC=CC=C1 Chemical compound CN1C(=NN=C1SCC1=NOC(=N1)C=1C=C(C=CC1)C)C=1C=NC=CC1.N1=CC=CC=C1 WWIHYVWCYRQJPX-UHFFFAOYSA-N 0.000 claims 1
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
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