JP2003510359A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2003510359A5 JP2003510359A5 JP2001527795A JP2001527795A JP2003510359A5 JP 2003510359 A5 JP2003510359 A5 JP 2003510359A5 JP 2001527795 A JP2001527795 A JP 2001527795A JP 2001527795 A JP2001527795 A JP 2001527795A JP 2003510359 A5 JP2003510359 A5 JP 2003510359A5
- Authority
- JP
- Japan
- Prior art keywords
- anilino
- triazole
- methyl
- benzylthio
- ylthio
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 description 29
- -1 4-methyl-anilino Chemical group 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 7
- 239000012453 solvate Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 5
- SSVJBYATJWWGDE-UHFFFAOYSA-N n-(4-methylphenyl)-3-(5-methylthiophen-2-yl)sulfanyl-1h-1,2,4-triazol-5-amine Chemical compound S1C(C)=CC=C1SC1=NNC(NC=2C=CC(C)=CC=2)=N1 SSVJBYATJWWGDE-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- YKODAWJGNWGCCV-UHFFFAOYSA-N 3-(3-chlorothiophen-2-yl)sulfanyl-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NC(SC2=C(C=CS2)Cl)=NN1 YKODAWJGNWGCCV-UHFFFAOYSA-N 0.000 description 3
- DHFXQZHZFCRGHS-UHFFFAOYSA-N 3-(3-methylthiophen-2-yl)sulfanyl-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NC(SC2=C(C=CS2)C)=NN1 DHFXQZHZFCRGHS-UHFFFAOYSA-N 0.000 description 3
- JPZYMONDMULCCK-UHFFFAOYSA-N 3-(5-bromothiophen-2-yl)sulfanyl-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound S1C(Br)=CC=C1SC1=NNC(NC=2C=CC=CC=2)=N1 JPZYMONDMULCCK-UHFFFAOYSA-N 0.000 description 3
- SXXLJBWSUTZQIT-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)sulfanyl-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NC(SC=2SC(Cl)=CC=2)=NN1 SXXLJBWSUTZQIT-UHFFFAOYSA-N 0.000 description 3
- OIATTZYGFPYFAQ-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)sulfanyl-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NC(SC=2SC(Cl)=CC=2)=NN1 OIATTZYGFPYFAQ-UHFFFAOYSA-N 0.000 description 3
- PXZUQHKCRDCAAE-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)sulfanyl-n-(4-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC(SC=2SC(Cl)=CC=2)=NN1 PXZUQHKCRDCAAE-UHFFFAOYSA-N 0.000 description 3
- PGDTXMNNIGGIQT-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)sulfanyl-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound S1C(Cl)=CC=C1SC1=NNC(NC=2C=CC=CC=2)=N1 PGDTXMNNIGGIQT-UHFFFAOYSA-N 0.000 description 3
- SNUJIKUEACLIOB-UHFFFAOYSA-N 3-(5-methylthiophen-2-yl)sulfanyl-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NC(SC=2SC(C)=CC=2)=NN1 SNUJIKUEACLIOB-UHFFFAOYSA-N 0.000 description 3
- SWNFXXFBTTZKJP-UHFFFAOYSA-N 3-(5-methylthiophen-2-yl)sulfanyl-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound S1C(C)=CC=C1SC1=NNC(NC=2C=CC=CC=2)=N1 SWNFXXFBTTZKJP-UHFFFAOYSA-N 0.000 description 3
- KFLGMQPKPRSNTG-UHFFFAOYSA-N 3-(furan-2-ylsulfanyl)-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2NN=C(SC=3OC=CC=3)N=2)=C1 KFLGMQPKPRSNTG-UHFFFAOYSA-N 0.000 description 3
- FAMZRVODLPRKNL-UHFFFAOYSA-N 3-(furan-2-ylsulfanyl)-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(SC=2OC=CC=2)=NN1 FAMZRVODLPRKNL-UHFFFAOYSA-N 0.000 description 3
- HYKJHMOWGREVRW-UHFFFAOYSA-N 3-(furan-2-ylsulfanyl)-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound C=1C=CC=CC=1NC(NN=1)=NC=1SC1=CC=CO1 HYKJHMOWGREVRW-UHFFFAOYSA-N 0.000 description 3
- RDQVJTIXBDRSQR-UHFFFAOYSA-N 3-(furan-3-ylsulfanyl)-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2NN=C(SC3=COC=C3)N=2)=C1 RDQVJTIXBDRSQR-UHFFFAOYSA-N 0.000 description 3
- NQKGTBWWTLSAHY-UHFFFAOYSA-N 3-(furan-3-ylsulfanyl)-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(SC2=COC=C2)=NN1 NQKGTBWWTLSAHY-UHFFFAOYSA-N 0.000 description 3
- XUVZBKHPSIVLBK-UHFFFAOYSA-N 3-(furan-3-ylsulfanyl)-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound C=1C=CC=CC=1NC(NN=1)=NC=1SC=1C=COC=1 XUVZBKHPSIVLBK-UHFFFAOYSA-N 0.000 description 3
- HSTMOEDERLQUGN-UHFFFAOYSA-N 3-benzylsulfanyl-n-(2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 HSTMOEDERLQUGN-UHFFFAOYSA-N 0.000 description 3
- JVESHYAZMYQQGG-UHFFFAOYSA-N 3-benzylsulfanyl-n-(4-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 JVESHYAZMYQQGG-UHFFFAOYSA-N 0.000 description 3
- VCSAYSMYYHLQSP-UHFFFAOYSA-N CC(C)c1ccccc1Nc1n[nH]c(Sc2ccco2)n1 Chemical compound CC(C)c1ccccc1Nc1n[nH]c(Sc2ccco2)n1 VCSAYSMYYHLQSP-UHFFFAOYSA-N 0.000 description 3
- CUQBEBOKLIGHEG-UHFFFAOYSA-N CC(C)c1ccccc1Nc1n[nH]c(Sc2ccoc2)n1 Chemical compound CC(C)c1ccccc1Nc1n[nH]c(Sc2ccoc2)n1 CUQBEBOKLIGHEG-UHFFFAOYSA-N 0.000 description 3
- DOYJEQSIVADNPC-UHFFFAOYSA-N CC(C)c1ccccc1Nc1n[nH]c(Sc2ccsc2)n1 Chemical compound CC(C)c1ccccc1Nc1n[nH]c(Sc2ccsc2)n1 DOYJEQSIVADNPC-UHFFFAOYSA-N 0.000 description 3
- HFZFNVMFRCEUKL-UHFFFAOYSA-N COc1ccccc1Nc1n[nH]c(Sc2sccc2Cl)n1 Chemical compound COc1ccccc1Nc1n[nH]c(Sc2sccc2Cl)n1 HFZFNVMFRCEUKL-UHFFFAOYSA-N 0.000 description 3
- DEASZYJQDZAWHG-UHFFFAOYSA-N Cc1ccccc1Nc1n[nH]c(Sc2ccco2)n1 Chemical compound Cc1ccccc1Nc1n[nH]c(Sc2ccco2)n1 DEASZYJQDZAWHG-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- COUGHWORWINHFG-UHFFFAOYSA-N ethyl 5-[[5-(2-propan-2-ylanilino)-1h-1,2,4-triazol-3-yl]sulfanylmethyl]furan-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC=C1CSC(N1)=NN=C1NC1=CC=CC=C1C(C)C COUGHWORWINHFG-UHFFFAOYSA-N 0.000 description 3
- UZPAVLYUTWNUSX-UHFFFAOYSA-N methyl 4-[(3-benzylsulfanyl-1h-1,2,4-triazol-5-yl)amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 UZPAVLYUTWNUSX-UHFFFAOYSA-N 0.000 description 3
- ZFZNSIGGHKANSR-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-(3-methylthiophen-2-yl)sulfanyl-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NC(SC2=C(C=CS2)C)=NN1 ZFZNSIGGHKANSR-UHFFFAOYSA-N 0.000 description 3
- UIDVAHJHCAALOW-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-(5-methylthiophen-2-yl)sulfanyl-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NC(SC=2SC(C)=CC=2)=NN1 UIDVAHJHCAALOW-UHFFFAOYSA-N 0.000 description 3
- XYVXLHYAPXUTFD-UHFFFAOYSA-N n-(3-methylphenyl)-3-thiophen-3-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2NN=C(SC3=CSC=C3)N=2)=C1 XYVXLHYAPXUTFD-UHFFFAOYSA-N 0.000 description 3
- HOQOTPFYKDHPPO-UHFFFAOYSA-N n-(3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-yl)pyridin-3-amine Chemical compound C=1C=CN=CC=1NC(N=1)=NNC=1SC1=CC=CS1 HOQOTPFYKDHPPO-UHFFFAOYSA-N 0.000 description 3
- KOLIQRWULWBTRO-UHFFFAOYSA-N n-(4-chlorophenyl)-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NC(SC=2SC=CC=2)=NN1 KOLIQRWULWBTRO-UHFFFAOYSA-N 0.000 description 3
- PJHSVELYXUUXPI-UHFFFAOYSA-N n-(4-methylphenyl)-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(SC=2SC=CC=2)=NN1 PJHSVELYXUUXPI-UHFFFAOYSA-N 0.000 description 3
- OITROJOEWSTWIW-UHFFFAOYSA-N n-(4-methylphenyl)-3-thiophen-3-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(SC2=CSC=C2)=NN1 OITROJOEWSTWIW-UHFFFAOYSA-N 0.000 description 3
- VBSSVYJFFVJXDJ-UHFFFAOYSA-N n-phenyl-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C=1C=CC=CC=1NC(NN=1)=NC=1SC1=CC=CS1 VBSSVYJFFVJXDJ-UHFFFAOYSA-N 0.000 description 3
- CSOPOFJNZYJZJH-UHFFFAOYSA-N n-phenyl-3-thiophen-3-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C=1C=CC=CC=1NC(NN=1)=NC=1SC=1C=CSC=1 CSOPOFJNZYJZJH-UHFFFAOYSA-N 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- PWXLEAVSSVXZGL-UHFFFAOYSA-N 3-(3-chlorothiophen-2-yl)sulfanyl-n-(2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1NC1=NC(SC2=C(C=CS2)Cl)=NN1 PWXLEAVSSVXZGL-UHFFFAOYSA-N 0.000 description 2
- CQUIZEMQWMKVMY-UHFFFAOYSA-N 3-(3-chlorothiophen-2-yl)sulfanyl-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2NN=C(SC3=C(C=CS3)Cl)N=2)=C1 CQUIZEMQWMKVMY-UHFFFAOYSA-N 0.000 description 2
- CWCKONMZORSQQK-UHFFFAOYSA-N 3-(3-chlorothiophen-2-yl)sulfanyl-n-(4-fluorophenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(F)=CC=C1NC1=NC(SC2=C(C=CS2)Cl)=NN1 CWCKONMZORSQQK-UHFFFAOYSA-N 0.000 description 2
- WRHMZDXBDXXIGK-UHFFFAOYSA-N 3-(3-chlorothiophen-2-yl)sulfanyl-n-(4-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC(SC2=C(C=CS2)Cl)=NN1 WRHMZDXBDXXIGK-UHFFFAOYSA-N 0.000 description 2
- DABRIDCJWJCDLJ-UHFFFAOYSA-N 3-(3-chlorothiophen-2-yl)sulfanyl-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(SC2=C(C=CS2)Cl)=NN1 DABRIDCJWJCDLJ-UHFFFAOYSA-N 0.000 description 2
- AMVHNDJLVTVGAU-UHFFFAOYSA-N 3-(3-chlorothiophen-2-yl)sulfanyl-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CSC(SC=2N=C(NC=3C=CC=CC=3)NN=2)=C1Cl AMVHNDJLVTVGAU-UHFFFAOYSA-N 0.000 description 2
- DHHDNUXVQYYLPA-UHFFFAOYSA-N 3-(3-methylthiophen-2-yl)sulfanyl-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CSC(SC=2N=C(NC=3C=CC=CC=3)NN=2)=C1C DHHDNUXVQYYLPA-UHFFFAOYSA-N 0.000 description 2
- HDDJDZDOKRLEPS-UHFFFAOYSA-N 3-(5-bromothiophen-2-yl)sulfanyl-n-(2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1NC1=NC(SC=2SC(Br)=CC=2)=NN1 HDDJDZDOKRLEPS-UHFFFAOYSA-N 0.000 description 2
- GKLBIFMCIQKIDU-UHFFFAOYSA-N 3-(5-bromothiophen-2-yl)sulfanyl-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2NN=C(SC=3SC(Br)=CC=3)N=2)=C1 GKLBIFMCIQKIDU-UHFFFAOYSA-N 0.000 description 2
- XOLYXWLLWMSDIJ-UHFFFAOYSA-N 3-(5-bromothiophen-2-yl)sulfanyl-n-(4-fluorophenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(F)=CC=C1NC1=NC(SC=2SC(Br)=CC=2)=NN1 XOLYXWLLWMSDIJ-UHFFFAOYSA-N 0.000 description 2
- CWAAIZHOPULLPV-UHFFFAOYSA-N 3-(5-bromothiophen-2-yl)sulfanyl-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(SC=2SC(Br)=CC=2)=NN1 CWAAIZHOPULLPV-UHFFFAOYSA-N 0.000 description 2
- IYHOHLKHYHPVSM-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)sulfanyl-n-(2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1NC1=NC(SC=2SC(Cl)=CC=2)=NN1 IYHOHLKHYHPVSM-UHFFFAOYSA-N 0.000 description 2
- UEKXWPIQOLHYDC-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)sulfanyl-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2NN=C(SC=3SC(Cl)=CC=3)N=2)=C1 UEKXWPIQOLHYDC-UHFFFAOYSA-N 0.000 description 2
- DDPXOOBFZFRAKM-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)sulfanyl-n-(4-fluorophenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(F)=CC=C1NC1=NC(SC=2SC(Cl)=CC=2)=NN1 DDPXOOBFZFRAKM-UHFFFAOYSA-N 0.000 description 2
- VDWMFPWXQFRLSC-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)sulfanyl-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(SC=2SC(Cl)=CC=2)=NN1 VDWMFPWXQFRLSC-UHFFFAOYSA-N 0.000 description 2
- ZGYUDXYEKJBWGQ-UHFFFAOYSA-N 3-(furan-2-ylsulfanyl)-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NC(SC=2OC=CC=2)=NN1 ZGYUDXYEKJBWGQ-UHFFFAOYSA-N 0.000 description 2
- SMQLCSMMAKTBSJ-UHFFFAOYSA-N 3-(furan-3-ylsulfanyl)-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NC(SC2=COC=C2)=NN1 SMQLCSMMAKTBSJ-UHFFFAOYSA-N 0.000 description 2
- NAFJUZKFEUUDKV-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 NAFJUZKFEUUDKV-UHFFFAOYSA-N 0.000 description 2
- NXBLUWQGGLQYQM-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2N=C(SCC=3C(=CC=CC=3)F)NN=2)=C1 NXBLUWQGGLQYQM-UHFFFAOYSA-N 0.000 description 2
- GDZHHXOYXPKDLO-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-n-(4-methoxy-2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 GDZHHXOYXPKDLO-UHFFFAOYSA-N 0.000 description 2
- UBZUXVQIHHRQHG-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-n-(4-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 UBZUXVQIHHRQHG-UHFFFAOYSA-N 0.000 description 2
- YYIJNRPVYDYLRE-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 YYIJNRPVYDYLRE-UHFFFAOYSA-N 0.000 description 2
- PPUFZAUHFAXGBM-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(2,4-dimethoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 PPUFZAUHFAXGBM-UHFFFAOYSA-N 0.000 description 2
- CNWQUDKZKSKAST-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(2,6-dimethylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(C)=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 CNWQUDKZKSKAST-UHFFFAOYSA-N 0.000 description 2
- FFIDUOXKZSOIBZ-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(2-ethylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 FFIDUOXKZSOIBZ-UHFFFAOYSA-N 0.000 description 2
- LCGRNWJSKOHUBU-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 LCGRNWJSKOHUBU-UHFFFAOYSA-N 0.000 description 2
- AQBIMSLMBXMPSV-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 AQBIMSLMBXMPSV-UHFFFAOYSA-N 0.000 description 2
- ZEHXHMKMTHWBQY-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(3,4-dimethoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 ZEHXHMKMTHWBQY-UHFFFAOYSA-N 0.000 description 2
- OIYTXJVMQLCGKD-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2N=C(SCC=3C=C(F)C(F)=CC=3)NN=2)=C1 OIYTXJVMQLCGKD-UHFFFAOYSA-N 0.000 description 2
- CQFAERVRCDLGBQ-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(4-methoxy-2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 CQFAERVRCDLGBQ-UHFFFAOYSA-N 0.000 description 2
- JCCLYBLQSDKYDK-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 JCCLYBLQSDKYDK-UHFFFAOYSA-N 0.000 description 2
- KTWYUXALXXVYQE-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound C1=C(F)C(F)=CC=C1CSC1=NC(NC=2C=CC=CC=2)=NN1 KTWYUXALXXVYQE-UHFFFAOYSA-N 0.000 description 2
- MKZCDFBGFBYCCQ-UHFFFAOYSA-N 3-[(4-fluorophenyl)methylsulfanyl]-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 MKZCDFBGFBYCCQ-UHFFFAOYSA-N 0.000 description 2
- MWNYEANTJBPRNF-UHFFFAOYSA-N 3-[(4-fluorophenyl)methylsulfanyl]-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2N=C(SCC=3C=CC(F)=CC=3)NN=2)=C1 MWNYEANTJBPRNF-UHFFFAOYSA-N 0.000 description 2
- CVZWCPNYLAZZKB-UHFFFAOYSA-N 3-[(4-fluorophenyl)methylsulfanyl]-n-(4-methoxy-2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 CVZWCPNYLAZZKB-UHFFFAOYSA-N 0.000 description 2
- CIEKRWSHGJRMTI-UHFFFAOYSA-N 3-benzylsulfanyl-n-(2,4-dimethoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 CIEKRWSHGJRMTI-UHFFFAOYSA-N 0.000 description 2
- HYWHAJUTCOADOO-UHFFFAOYSA-N 3-benzylsulfanyl-n-(2,6-dimethylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(C)=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 HYWHAJUTCOADOO-UHFFFAOYSA-N 0.000 description 2
- WAXBOCRNJSPCTC-UHFFFAOYSA-N 3-benzylsulfanyl-n-(2-ethylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 WAXBOCRNJSPCTC-UHFFFAOYSA-N 0.000 description 2
- OFJZILFQGXSVMM-UHFFFAOYSA-N 3-benzylsulfanyl-n-(3,4-dimethoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 OFJZILFQGXSVMM-UHFFFAOYSA-N 0.000 description 2
- VBNUTJNQBYAABU-UHFFFAOYSA-N 3-benzylsulfanyl-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2N=C(SCC=3C=CC=CC=3)NN=2)=C1 VBNUTJNQBYAABU-UHFFFAOYSA-N 0.000 description 2
- CLFNJJAUZYKYCJ-UHFFFAOYSA-N 3-benzylsulfanyl-n-(4-chlorophenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 CLFNJJAUZYKYCJ-UHFFFAOYSA-N 0.000 description 2
- JZJFXCKLZBMUKY-UHFFFAOYSA-N 3-benzylsulfanyl-n-(4-methoxy-2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 JZJFXCKLZBMUKY-UHFFFAOYSA-N 0.000 description 2
- MSCIKZGQDUGLMX-UHFFFAOYSA-N 3-benzylsulfanyl-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 MSCIKZGQDUGLMX-UHFFFAOYSA-N 0.000 description 2
- QBUZLNWDECJZMT-UHFFFAOYSA-N 3-benzylsulfanyl-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound C=1C=CC=CC=1CSC(NN=1)=NC=1NC1=CC=CC=C1 QBUZLNWDECJZMT-UHFFFAOYSA-N 0.000 description 2
- FHIPHLQUMZUIKM-UHFFFAOYSA-N 5-[(5-anilino-1h-1,2,4-triazol-3-yl)sulfanylmethyl]furan-2-carbaldehyde Chemical compound O1C(C=O)=CC=C1CSC(N1)=NN=C1NC1=CC=CC=C1 FHIPHLQUMZUIKM-UHFFFAOYSA-N 0.000 description 2
- RFMCIVZPIQKMMO-UHFFFAOYSA-N 5-[[5-(2-methylanilino)-1h-1,2,4-triazol-3-yl]sulfanylmethyl]furan-2-carbaldehyde Chemical compound CC1=CC=CC=C1NC(N1)=NN=C1SCC1=CC=C(C=O)O1 RFMCIVZPIQKMMO-UHFFFAOYSA-N 0.000 description 2
- VPUAEVACUKCMCW-UHFFFAOYSA-N 5-[[5-(3-methylanilino)-1h-1,2,4-triazol-3-yl]sulfanylmethyl]furan-2-carbaldehyde Chemical compound CC1=CC=CC(NC=2NC(SCC=3OC(C=O)=CC=3)=NN=2)=C1 VPUAEVACUKCMCW-UHFFFAOYSA-N 0.000 description 2
- USQQHLGLOVLGTK-UHFFFAOYSA-N 5-[[5-(4-fluoroanilino)-1h-1,2,4-triazol-3-yl]sulfanylmethyl]furan-2-carbaldehyde Chemical compound C1=CC(F)=CC=C1NC(N1)=NN=C1SCC1=CC=C(C=O)O1 USQQHLGLOVLGTK-UHFFFAOYSA-N 0.000 description 2
- XHLYZZMNXILNMW-UHFFFAOYSA-N 5-[[5-(4-methylanilino)-1h-1,2,4-triazol-3-yl]sulfanylmethyl]furan-2-carbaldehyde Chemical compound C1=CC(C)=CC=C1NC(N1)=NN=C1SCC1=CC=C(C=O)O1 XHLYZZMNXILNMW-UHFFFAOYSA-N 0.000 description 2
- KCAHISAOWMHACF-UHFFFAOYSA-N 5-benzylsulfanyl-3-ethyl-n-phenyl-1,2,4-triazol-3-amine Chemical compound N1=NC(SCC=2C=CC=CC=2)=NC1(CC)NC1=CC=CC=C1 KCAHISAOWMHACF-UHFFFAOYSA-N 0.000 description 2
- WADOXIZPNRBDQF-UHFFFAOYSA-N 5-benzylsulfanyl-n-phenyl-3-propyl-1,2,4-triazol-3-amine Chemical compound N1=NC(SCC=2C=CC=CC=2)=NC1(CCC)NC1=CC=CC=C1 WADOXIZPNRBDQF-UHFFFAOYSA-N 0.000 description 2
- WQOYRTXJUNAJKA-UHFFFAOYSA-N CCc1ccccc1Nc1n[nH]c(Sc2cccs2)n1 Chemical compound CCc1ccccc1Nc1n[nH]c(Sc2cccs2)n1 WQOYRTXJUNAJKA-UHFFFAOYSA-N 0.000 description 2
- AUPSHFREBQUIDS-UHFFFAOYSA-N Cc1cccc(Nc2n[nH]c(Sc3cccs3)n2)c1 Chemical compound Cc1cccc(Nc2n[nH]c(Sc3cccs3)n2)c1 AUPSHFREBQUIDS-UHFFFAOYSA-N 0.000 description 2
- ISTWVJVSILOJBB-UHFFFAOYSA-N Cc1ccccc1Nc1n[nH]c(Sc2cccs2)n1 Chemical compound Cc1ccccc1Nc1n[nH]c(Sc2cccs2)n1 ISTWVJVSILOJBB-UHFFFAOYSA-N 0.000 description 2
- XKTVLHDHPZMYAB-UHFFFAOYSA-N Cc1ccccc1Nc1n[nH]c(Sc2ccoc2)n1 Chemical compound Cc1ccccc1Nc1n[nH]c(Sc2ccoc2)n1 XKTVLHDHPZMYAB-UHFFFAOYSA-N 0.000 description 2
- NRIPGQLYDKKSSR-UHFFFAOYSA-N Fc1ccc(Nc2n[nH]c(Sc3ccoc3)n2)cc1 Chemical compound Fc1ccc(Nc2n[nH]c(Sc3ccoc3)n2)cc1 NRIPGQLYDKKSSR-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 230000033115 angiogenesis Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- PHVWMPUOSIYORD-UHFFFAOYSA-N ethyl 5-[(5-anilino-1h-1,2,4-triazol-3-yl)sulfanylmethyl]furan-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC=C1CSC(N1)=NN=C1NC1=CC=CC=C1 PHVWMPUOSIYORD-UHFFFAOYSA-N 0.000 description 2
- KWECNHBWXYYVEP-UHFFFAOYSA-N ethyl 5-[[5-(2-methoxyanilino)-1h-1,2,4-triazol-3-yl]sulfanylmethyl]furan-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC=C1CSC(N1)=NN=C1NC1=CC=CC=C1OC KWECNHBWXYYVEP-UHFFFAOYSA-N 0.000 description 2
- VXISNCVIHVIJTI-UHFFFAOYSA-N ethyl 5-[[5-(2-methylanilino)-1h-1,2,4-triazol-3-yl]sulfanylmethyl]furan-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC=C1CSC(N1)=NN=C1NC1=CC=CC=C1C VXISNCVIHVIJTI-UHFFFAOYSA-N 0.000 description 2
- LCSCYHPLINKEBH-UHFFFAOYSA-N ethyl 5-[[5-(4-fluoroanilino)-1h-1,2,4-triazol-3-yl]sulfanylmethyl]furan-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC=C1CSC(N1)=NN=C1NC1=CC=C(F)C=C1 LCSCYHPLINKEBH-UHFFFAOYSA-N 0.000 description 2
- IUVXVZQXZGZLMI-UHFFFAOYSA-N ethyl 5-[[5-(4-methylanilino)-1h-1,2,4-triazol-3-yl]sulfanylmethyl]furan-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC=C1CSC(N1)=NN=C1NC1=CC=C(C)C=C1 IUVXVZQXZGZLMI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BZRABYOGPQHVJS-UHFFFAOYSA-N methyl 4-[[3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)OC)=N1 BZRABYOGPQHVJS-UHFFFAOYSA-N 0.000 description 2
- WJUVOKOQWNBXMR-UHFFFAOYSA-N methyl 4-[[3-[(3,4-difluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 WJUVOKOQWNBXMR-UHFFFAOYSA-N 0.000 description 2
- OWQXMEGPYKVJTE-UHFFFAOYSA-N methyl 4-[[3-[(3-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC=2C=C(OC)C=CC=2)=N1 OWQXMEGPYKVJTE-UHFFFAOYSA-N 0.000 description 2
- QHSDUGQGPSMGLM-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-3-[(2-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 QHSDUGQGPSMGLM-UHFFFAOYSA-N 0.000 description 2
- CWWQVJYPJGUIIE-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-3-[(4-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 CWWQVJYPJGUIIE-UHFFFAOYSA-N 0.000 description 2
- LEFKCFSVZHUESK-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NC(SC=2SC=CC=2)=NN1 LEFKCFSVZHUESK-UHFFFAOYSA-N 0.000 description 2
- NCNIBQLSTUFUFR-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-3-[(2-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(C)=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 NCNIBQLSTUFUFR-UHFFFAOYSA-N 0.000 description 2
- YMRMQAFSXBDKPX-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-3-[(4-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(C)=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 YMRMQAFSXBDKPX-UHFFFAOYSA-N 0.000 description 2
- FUYBXYSTWBSFJO-UHFFFAOYSA-N n-(2-ethylphenyl)-3-[(2-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 FUYBXYSTWBSFJO-UHFFFAOYSA-N 0.000 description 2
- FEKPHPGOKGXZOL-UHFFFAOYSA-N n-(2-ethylphenyl)-3-[(4-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 FEKPHPGOKGXZOL-UHFFFAOYSA-N 0.000 description 2
- XNPZSYHTBLCMEE-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NC(SC=2SC=CC=2)=NN1 XNPZSYHTBLCMEE-UHFFFAOYSA-N 0.000 description 2
- BQOBXXPDLZZRJS-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-thiophen-3-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NC(SC2=CSC=C2)=NN1 BQOBXXPDLZZRJS-UHFFFAOYSA-N 0.000 description 2
- YOQGUKOISWZTFQ-UHFFFAOYSA-N n-(2-methylphenyl)-3-(3-methylthiophen-2-yl)sulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CSC(SC=2N=C(NC=3C(=CC=CC=3)C)NN=2)=C1C YOQGUKOISWZTFQ-UHFFFAOYSA-N 0.000 description 2
- AMSRGYFUPIKPMQ-UHFFFAOYSA-N n-(2-methylphenyl)-3-(5-methylthiophen-2-yl)sulfanyl-1h-1,2,4-triazol-5-amine Chemical compound S1C(C)=CC=C1SC1=NNC(NC=2C(=CC=CC=2)C)=N1 AMSRGYFUPIKPMQ-UHFFFAOYSA-N 0.000 description 2
- BBEIYRRUQXXVHC-UHFFFAOYSA-N n-(2-propan-2-ylphenyl)-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NC(SC=2SC=CC=2)=NN1 BBEIYRRUQXXVHC-UHFFFAOYSA-N 0.000 description 2
- UWPYDBFFBODQBL-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-3-[(2-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 UWPYDBFFBODQBL-UHFFFAOYSA-N 0.000 description 2
- SVBPPCULWIQVTO-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1CSC1=NC(NC=2C=C(OC)C(OC)=CC=2)=NN1 SVBPPCULWIQVTO-UHFFFAOYSA-N 0.000 description 2
- LXPYJMBMOSTEOW-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-3-[(3-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC(CSC=2NN=C(NC=3C=C(OC)C(OC)=CC=3)N=2)=C1 LXPYJMBMOSTEOW-UHFFFAOYSA-N 0.000 description 2
- REEAZBAQKRGCLX-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(SC=2SC=CC=2)=NN1 REEAZBAQKRGCLX-UHFFFAOYSA-N 0.000 description 2
- XEMSNSNJVPHYPA-UHFFFAOYSA-N n-(3-methylphenyl)-3-(3-methylthiophen-2-yl)sulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CSC(SC=2N=C(NC=3C=C(C)C=CC=3)NN=2)=C1C XEMSNSNJVPHYPA-UHFFFAOYSA-N 0.000 description 2
- APGRAKCIIKDKSD-UHFFFAOYSA-N n-(3-methylphenyl)-3-(5-methylthiophen-2-yl)sulfanyl-1h-1,2,4-triazol-5-amine Chemical compound S1C(C)=CC=C1SC1=NNC(NC=2C=C(C)C=CC=2)=N1 APGRAKCIIKDKSD-UHFFFAOYSA-N 0.000 description 2
- PZNGLXREQHSKFW-UHFFFAOYSA-N n-(4-butylphenyl)-3-[(2-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 PZNGLXREQHSKFW-UHFFFAOYSA-N 0.000 description 2
- DHAZWIIKGZEPGW-UHFFFAOYSA-N n-(4-butylphenyl)-3-[(3,4-difluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 DHAZWIIKGZEPGW-UHFFFAOYSA-N 0.000 description 2
- IPTPWKJLWLOGSK-UHFFFAOYSA-N n-(4-butylphenyl)-3-[(4-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 IPTPWKJLWLOGSK-UHFFFAOYSA-N 0.000 description 2
- DWPUAEXAPBLHSW-UHFFFAOYSA-N n-(4-butylphenyl)-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NC(SC=2SC=CC=2)=NN1 DWPUAEXAPBLHSW-UHFFFAOYSA-N 0.000 description 2
- JPWRGMWKHAEHKC-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[(2-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound FC1=CC=CC=C1CSC1=NC(NC=2C=CC(Cl)=CC=2)=NN1 JPWRGMWKHAEHKC-UHFFFAOYSA-N 0.000 description 2
- YJFCWNYTKZVLEA-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[(3,4-difluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=C(F)C(F)=CC=C1CSC1=NC(NC=2C=CC(Cl)=CC=2)=NN1 YJFCWNYTKZVLEA-UHFFFAOYSA-N 0.000 description 2
- DDWHPJQBBGKWLP-UHFFFAOYSA-N n-(4-fluorophenyl)-3-(3-methylthiophen-2-yl)sulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CSC(SC=2N=C(NC=3C=CC(F)=CC=3)NN=2)=C1C DDWHPJQBBGKWLP-UHFFFAOYSA-N 0.000 description 2
- XTWZYRBWKKYCIW-UHFFFAOYSA-N n-(4-fluorophenyl)-3-(5-methylthiophen-2-yl)sulfanyl-1h-1,2,4-triazol-5-amine Chemical compound S1C(C)=CC=C1SC1=NNC(NC=2C=CC(F)=CC=2)=N1 XTWZYRBWKKYCIW-UHFFFAOYSA-N 0.000 description 2
- MMSDGZLDMNHFEJ-UHFFFAOYSA-N n-(4-fluorophenyl)-3-(furan-2-ylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(F)=CC=C1NC1=NC(SC=2OC=CC=2)=NN1 MMSDGZLDMNHFEJ-UHFFFAOYSA-N 0.000 description 2
- YASQUTIKKJKSSL-UHFFFAOYSA-N n-(4-fluorophenyl)-3-thiophen-3-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(F)=CC=C1NC1=NC(SC2=CSC=C2)=NN1 YASQUTIKKJKSSL-UHFFFAOYSA-N 0.000 description 2
- VWEJYKKSAAYXMD-UHFFFAOYSA-N n-(4-methoxy-2-methylphenyl)-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NC(SC=2SC=CC=2)=NN1 VWEJYKKSAAYXMD-UHFFFAOYSA-N 0.000 description 2
- GNKKFOKAICLWIY-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)OC)=N1 GNKKFOKAICLWIY-UHFFFAOYSA-N 0.000 description 2
- IVCQNJJPZXCTQQ-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC(SC=2SC=CC=2)=NN1 IVCQNJJPZXCTQQ-UHFFFAOYSA-N 0.000 description 2
- TWRSNUIWPOALRR-UHFFFAOYSA-N n-(4-methylphenyl)-3-(3-methylthiophen-2-yl)sulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CSC(SC=2N=C(NC=3C=CC(C)=CC=3)NN=2)=C1C TWRSNUIWPOALRR-UHFFFAOYSA-N 0.000 description 2
- XUUJLHGOJDTMAJ-UHFFFAOYSA-N n-[3-[(2-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]pyridin-3-amine Chemical compound FC1=CC=CC=C1CSC1=NC(NC=2C=NC=CC=2)=NN1 XUUJLHGOJDTMAJ-UHFFFAOYSA-N 0.000 description 2
- SWBHUFGZKMHJDT-UHFFFAOYSA-N n-[3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]pyridin-3-amine Chemical compound COC1=CC=CC=C1CSC1=NC(NC=2C=NC=CC=2)=NN1 SWBHUFGZKMHJDT-UHFFFAOYSA-N 0.000 description 2
- ARJPWOXCGAOYMT-UHFFFAOYSA-N n-[3-[(3,4-difluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]pyridin-3-amine Chemical compound C1=C(F)C(F)=CC=C1CSC1=NC(NC=2C=NC=CC=2)=NN1 ARJPWOXCGAOYMT-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- CVEWJAKXWDVKCP-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-ylmethylsulfanyl)-n-(2,4-dimethoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC=2C=C3OCOC3=CC=2)=N1 CVEWJAKXWDVKCP-UHFFFAOYSA-N 0.000 description 1
- VRLAFIZAIIXUGO-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-ylmethylsulfanyl)-n-(2-ethylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC=2C=C3OCOC3=CC=2)=N1 VRLAFIZAIIXUGO-UHFFFAOYSA-N 0.000 description 1
- PDUZGQKQYSPCTH-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-ylmethylsulfanyl)-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC=2C=C3OCOC3=CC=2)=N1 PDUZGQKQYSPCTH-UHFFFAOYSA-N 0.000 description 1
- GFDSRNCEURBRII-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-ylmethylsulfanyl)-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NNC(SCC=2C=C3OCOC3=CC=2)=N1 GFDSRNCEURBRII-UHFFFAOYSA-N 0.000 description 1
- NTBRNPANYRABIW-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-ylmethylsulfanyl)-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2N=C(SCC=3C=C4OCOC4=CC=3)NN=2)=C1 NTBRNPANYRABIW-UHFFFAOYSA-N 0.000 description 1
- XJPSVDZBPDQXBJ-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-ylmethylsulfanyl)-n-(4-butylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC=2C=C3OCOC3=CC=2)=N1 XJPSVDZBPDQXBJ-UHFFFAOYSA-N 0.000 description 1
- DWLHGNLJHFCJSM-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-ylmethylsulfanyl)-n-(4-methoxy-2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC=2C=C3OCOC3=CC=2)=N1 DWLHGNLJHFCJSM-UHFFFAOYSA-N 0.000 description 1
- FIBYDZALNMUJEQ-UHFFFAOYSA-N 3-(1h-benzimidazol-2-ylmethylsulfanyl)-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound N=1C2=CC=CC=C2NC=1CSC(NN=1)=NC=1NC1=CC=CC=C1 FIBYDZALNMUJEQ-UHFFFAOYSA-N 0.000 description 1
- UYXDEDHNPNKSTC-UHFFFAOYSA-N 3-(2-methylbut-2-enylsulfanyl)-n-(2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound N1C(SCC(C)=CC)=NC(NC=2C(=CC=CC=2)C)=N1 UYXDEDHNPNKSTC-UHFFFAOYSA-N 0.000 description 1
- XIWKNEZUHDCLBK-UHFFFAOYSA-N 3-(2-methylbut-2-enylsulfanyl)-n-(2-phenylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound N1C(SCC(C)=CC)=NC(NC=2C(=CC=CC=2)C=2C=CC=CC=2)=N1 XIWKNEZUHDCLBK-UHFFFAOYSA-N 0.000 description 1
- SXZQKRVNLXGCFR-UHFFFAOYSA-N 3-(2-methylbut-2-enylsulfanyl)-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound N1C(SCC(C)=CC)=NC(NC=2C(=CC=CC=2)C(C)C)=N1 SXZQKRVNLXGCFR-UHFFFAOYSA-N 0.000 description 1
- IQPOCOPYVNYJBH-UHFFFAOYSA-N 3-(2-methylbut-2-enylsulfanyl)-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound N1C(SCC(C)=CC)=NC(NC=2C=C(C)C=CC=2)=N1 IQPOCOPYVNYJBH-UHFFFAOYSA-N 0.000 description 1
- RURMCCWBKBFHJH-UHFFFAOYSA-N 3-(2-methylbut-2-enylsulfanyl)-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound N1C(SCC(C)=CC)=NC(NC=2C=CC(C)=CC=2)=N1 RURMCCWBKBFHJH-UHFFFAOYSA-N 0.000 description 1
- ZTWFBOYRVWAZKD-UHFFFAOYSA-N 3-(2-methylbut-2-enylsulfanyl)-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound N1C(SCC(C)=CC)=NC(NC=2C=CC=CC=2)=N1 ZTWFBOYRVWAZKD-UHFFFAOYSA-N 0.000 description 1
- LQJLFBUGJAZRSE-UHFFFAOYSA-N 3-(2-methylbutylsulfanyl)-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound N1C(SCC(C)CC)=NC(NC=2C=CC=CC=2)=N1 LQJLFBUGJAZRSE-UHFFFAOYSA-N 0.000 description 1
- WEMWOOUTOGIBFN-UHFFFAOYSA-N 3-(2-methylpent-2-enylsulfanyl)-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound N1C(SCC(C)=CCC)=NC(NC=2C=CC=CC=2)=N1 WEMWOOUTOGIBFN-UHFFFAOYSA-N 0.000 description 1
- YIVLZQBGHMUQPM-UHFFFAOYSA-N 3-(3,3-dimethoxypropylsulfanyl)-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound N1C(SCCC(OC)OC)=NC(NC=2C=CC=CC=2)=N1 YIVLZQBGHMUQPM-UHFFFAOYSA-N 0.000 description 1
- KPFFBQFQZGOKLT-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-n-(2,4-dimethoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC2CCCCC2)=N1 KPFFBQFQZGOKLT-UHFFFAOYSA-N 0.000 description 1
- UARCNRZQGUQSDS-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-n-(2,6-dimethylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(C)=C1NC1=NNC(SCC2CCCCC2)=N1 UARCNRZQGUQSDS-UHFFFAOYSA-N 0.000 description 1
- YGUZSEZYQUMCQY-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC2CCCCC2)=N1 YGUZSEZYQUMCQY-UHFFFAOYSA-N 0.000 description 1
- JXLQLHGNQJVACA-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-n-(2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1NC1=NNC(SCC2CCCCC2)=N1 JXLQLHGNQJVACA-UHFFFAOYSA-N 0.000 description 1
- NAUIOAAAANZLAH-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-n-(2-phenylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1CCCCC1CSC(NN=1)=NC=1NC1=CC=CC=C1C1=CC=CC=C1 NAUIOAAAANZLAH-UHFFFAOYSA-N 0.000 description 1
- LVFPEWDJSOCCLD-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NNC(SCC2CCCCC2)=N1 LVFPEWDJSOCCLD-UHFFFAOYSA-N 0.000 description 1
- UTUOVFSYLPFVFY-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-n-(3,4-dimethoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NNC(SCC2CCCCC2)=N1 UTUOVFSYLPFVFY-UHFFFAOYSA-N 0.000 description 1
- CUGKCIBBSUOQSZ-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2N=C(SCC3CCCCC3)NN=2)=C1 CUGKCIBBSUOQSZ-UHFFFAOYSA-N 0.000 description 1
- JFFKAQGHCCFLFV-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-n-(4-methoxy-2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC2CCCCC2)=N1 JFFKAQGHCCFLFV-UHFFFAOYSA-N 0.000 description 1
- QRZAVCKGFCAJMY-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-n-(4-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC2CCCCC2)=N1 QRZAVCKGFCAJMY-UHFFFAOYSA-N 0.000 description 1
- HSCLFMLCXGYQLZ-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NNC(SCC2CCCCC2)=N1 HSCLFMLCXGYQLZ-UHFFFAOYSA-N 0.000 description 1
- KOFYTAHVHHHKQA-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound C1CCCCC1CSC(NN=1)=NC=1NC1=CC=CC=C1 KOFYTAHVHHHKQA-UHFFFAOYSA-N 0.000 description 1
- DVWBBKMOVHXGGD-UHFFFAOYSA-N 3-[(2-chlorophenyl)methylsulfanyl]-n-(2,4-dimethoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)Cl)=N1 DVWBBKMOVHXGGD-UHFFFAOYSA-N 0.000 description 1
- XJQIJNVZSXXCJR-UHFFFAOYSA-N 3-[(2-chlorophenyl)methylsulfanyl]-n-(2,6-dimethylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(C)=C1NC1=NNC(SCC=2C(=CC=CC=2)Cl)=N1 XJQIJNVZSXXCJR-UHFFFAOYSA-N 0.000 description 1
- ULKUYEZKVYMYGJ-UHFFFAOYSA-N 3-[(2-chlorophenyl)methylsulfanyl]-n-(2-ethylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)Cl)=N1 ULKUYEZKVYMYGJ-UHFFFAOYSA-N 0.000 description 1
- GUNHDLZLOGCVSH-UHFFFAOYSA-N 3-[(2-chlorophenyl)methylsulfanyl]-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)Cl)=N1 GUNHDLZLOGCVSH-UHFFFAOYSA-N 0.000 description 1
- IXOCCTYYIJKLIP-UHFFFAOYSA-N 3-[(2-chlorophenyl)methylsulfanyl]-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)Cl)=N1 IXOCCTYYIJKLIP-UHFFFAOYSA-N 0.000 description 1
- CNGBSBQKXYDNKE-UHFFFAOYSA-N 3-[(2-chlorophenyl)methylsulfanyl]-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2N=C(SCC=3C(=CC=CC=3)Cl)NN=2)=C1 CNGBSBQKXYDNKE-UHFFFAOYSA-N 0.000 description 1
- DTDQOIGMJHDVSA-UHFFFAOYSA-N 3-[(2-chlorophenyl)methylsulfanyl]-n-(4-methoxy-2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)Cl)=N1 DTDQOIGMJHDVSA-UHFFFAOYSA-N 0.000 description 1
- WSFROHSHSOLJMP-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-N-(2-methylphenyl)-1H-1,2,4-triazol-5-amine 3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-N-(2-methylphenyl)-1H-1,2,4-triazol-5-amine Chemical compound CC1=C(NC2=NNC(=N2)SCC2=NOC(=C2)C)C=CC=C1.CC1=C(NC2=NNC(=N2)SCC2=C(C=CC=C2)F)C=CC=C1 WSFROHSHSOLJMP-UHFFFAOYSA-N 0.000 description 1
- DCLWRUVNTOSXQM-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-n-(2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 DCLWRUVNTOSXQM-UHFFFAOYSA-N 0.000 description 1
- STRIDWPNAFHBQX-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-n-(2-phenylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound FC1=CC=CC=C1CSC1=NC(NC=2C(=CC=CC=2)C=2C=CC=CC=2)=NN1 STRIDWPNAFHBQX-UHFFFAOYSA-N 0.000 description 1
- XTZXXRCWDQFBSN-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 XTZXXRCWDQFBSN-UHFFFAOYSA-N 0.000 description 1
- INLCXQQDEZOCQH-UHFFFAOYSA-N 3-[(2-methoxyphenyl)methylsulfanyl]-n-(2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1CSC1=NC(NC=2C(=CC=CC=2)C)=NN1 INLCXQQDEZOCQH-UHFFFAOYSA-N 0.000 description 1
- KFAWWQVSTXZRSJ-UHFFFAOYSA-N 3-[(2-methoxyphenyl)methylsulfanyl]-n-(2-phenylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1CSC1=NC(NC=2C(=CC=CC=2)C=2C=CC=CC=2)=NN1 KFAWWQVSTXZRSJ-UHFFFAOYSA-N 0.000 description 1
- QTCMVLSPHYRBOG-UHFFFAOYSA-N 3-[(2-methoxyphenyl)methylsulfanyl]-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1CSC1=NC(NC=2C(=CC=CC=2)C(C)C)=NN1 QTCMVLSPHYRBOG-UHFFFAOYSA-N 0.000 description 1
- LSESGLXZKXQNHA-UHFFFAOYSA-N 3-[(2-methoxyphenyl)methylsulfanyl]-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1CSC1=NC(NC=2C=C(C)C=CC=2)=NN1 LSESGLXZKXQNHA-UHFFFAOYSA-N 0.000 description 1
- NBAWRRSKESPCRE-UHFFFAOYSA-N 3-[(2-methoxyphenyl)methylsulfanyl]-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1CSC1=NC(NC=2C=CC(C)=CC=2)=NN1 NBAWRRSKESPCRE-UHFFFAOYSA-N 0.000 description 1
- UMJAYCQLSHRPJK-UHFFFAOYSA-N 3-[(2-methyl-1,3-thiazol-4-yl)methylsulfanyl]-n-(2-phenylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound S1C(C)=NC(CSC=2NN=C(NC=3C(=CC=CC=3)C=3C=CC=CC=3)N=2)=C1 UMJAYCQLSHRPJK-UHFFFAOYSA-N 0.000 description 1
- KZFWCWDSJOVPOR-UHFFFAOYSA-N 3-[(2-methyl-1,3-thiazol-4-yl)methylsulfanyl]-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound S1C(C)=NC(CSC=2NN=C(NC=3C=CC=CC=3)N=2)=C1 KZFWCWDSJOVPOR-UHFFFAOYSA-N 0.000 description 1
- MEGHOPIQKPOUER-UHFFFAOYSA-N 3-[(2-methylphenyl)methylsulfanyl]-n-(2-phenylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1CSC1=NC(NC=2C(=CC=CC=2)C=2C=CC=CC=2)=NN1 MEGHOPIQKPOUER-UHFFFAOYSA-N 0.000 description 1
- CTEQOIBOAGPKAH-UHFFFAOYSA-N 3-[(2-methylphenyl)methylsulfanyl]-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)C)=N1 CTEQOIBOAGPKAH-UHFFFAOYSA-N 0.000 description 1
- UWNPKMQGHJRDMV-UHFFFAOYSA-N 3-[(2-methylphenyl)methylsulfanyl]-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1CSC1=NC(NC=2C=CC=CC=2)=NN1 UWNPKMQGHJRDMV-UHFFFAOYSA-N 0.000 description 1
- WQOJCALSHDTKCT-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(2-phenylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=C(F)C(F)=CC=C1CSC1=NC(NC=2C(=CC=CC=2)C=2C=CC=CC=2)=NN1 WQOJCALSHDTKCT-UHFFFAOYSA-N 0.000 description 1
- JTVWXODAZSBHGR-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 JTVWXODAZSBHGR-UHFFFAOYSA-N 0.000 description 1
- SQPPNLAFFBHMTB-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(4-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 SQPPNLAFFBHMTB-UHFFFAOYSA-N 0.000 description 1
- VZJHTKMUUAAJOE-UHFFFAOYSA-N 3-[(3,5-dimethylphenyl)methylsulfanyl]-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(C)=CC(CSC=2NN=C(NC=3C=CC=CC=3)N=2)=C1 VZJHTKMUUAAJOE-UHFFFAOYSA-N 0.000 description 1
- FBZQIZMRKIHQLV-UHFFFAOYSA-N 3-[(3-methoxyphenyl)methylsulfanyl]-n-(2-phenylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC(CSC=2NN=C(NC=3C(=CC=CC=3)C=3C=CC=CC=3)N=2)=C1 FBZQIZMRKIHQLV-UHFFFAOYSA-N 0.000 description 1
- AQTAQBLIEFPQGP-UHFFFAOYSA-N 3-[(4-chlorophenyl)methylsulfanyl]-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(Cl)=CC=C1CSC1=NC(NC=2C=CC=CC=2)=NN1 AQTAQBLIEFPQGP-UHFFFAOYSA-N 0.000 description 1
- BCCCCILCGLSRGI-UHFFFAOYSA-N 3-[(4-fluorophenyl)methylsulfanyl]-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 BCCCCILCGLSRGI-UHFFFAOYSA-N 0.000 description 1
- PPUXAINXZDSWQK-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methylsulfanyl]-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1CSC1=NC(NC=2C(=CC=CC=2)C(C)C)=NN1 PPUXAINXZDSWQK-UHFFFAOYSA-N 0.000 description 1
- IVQAHULLHHQZRP-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methylsulfanyl]-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1CSC1=NC(NC=2C=C(C)C=CC=2)=NN1 IVQAHULLHHQZRP-UHFFFAOYSA-N 0.000 description 1
- BESDVTLBOJMHET-UHFFFAOYSA-N 3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-n-(2-phenylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound O1C(C)=CC(CSC=2NN=C(NC=3C(=CC=CC=3)C=3C=CC=CC=3)N=2)=N1 BESDVTLBOJMHET-UHFFFAOYSA-N 0.000 description 1
- ZGSGKKNNZBPUFR-UHFFFAOYSA-N 3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NNC(SCC2=NOC(C)=C2)=N1 ZGSGKKNNZBPUFR-UHFFFAOYSA-N 0.000 description 1
- YQLPUAIAMXMGIK-UHFFFAOYSA-N 3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound O1C(C)=CC(CSC=2NN=C(NC=3C=C(C)C=CC=3)N=2)=N1 YQLPUAIAMXMGIK-UHFFFAOYSA-N 0.000 description 1
- QWHUCUJGEQGJHL-UHFFFAOYSA-N 3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound O1C(C)=CC(CSC=2NN=C(NC=3C=CC(C)=CC=3)N=2)=N1 QWHUCUJGEQGJHL-UHFFFAOYSA-N 0.000 description 1
- OINGZPXMGXQZTC-UHFFFAOYSA-N 3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound O1C(C)=CC(CSC=2NN=C(NC=3C=CC=CC=3)N=2)=N1 OINGZPXMGXQZTC-UHFFFAOYSA-N 0.000 description 1
- WFJJLUPZWBAOKG-UHFFFAOYSA-N 3-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methylsulfanyl]-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(Cl)=CC=C1C1=NC(CSC=2NN=C(NC=3C=CC=CC=3)N=2)=CS1 WFJJLUPZWBAOKG-UHFFFAOYSA-N 0.000 description 1
- ATBNJWRVIFSORI-UHFFFAOYSA-N 3-benzyl-5-benzylsulfanyl-n-phenyl-1,2,4-triazol-3-amine Chemical compound C=1C=CC=CC=1CSC(N=N1)=NC1(NC=1C=CC=CC=1)CC1=CC=CC=C1 ATBNJWRVIFSORI-UHFFFAOYSA-N 0.000 description 1
- NSQLTDMTLKMKJF-UHFFFAOYSA-N 3-benzylsulfanyl-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 NSQLTDMTLKMKJF-UHFFFAOYSA-N 0.000 description 1
- ADMIGCHPABJGNF-UHFFFAOYSA-N 3-benzylsulfanyl-n-(2-phenylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C=1C=CC=CC=1CSC(NN=1)=NC=1NC1=CC=CC=C1C1=CC=CC=C1 ADMIGCHPABJGNF-UHFFFAOYSA-N 0.000 description 1
- MWDRNNBQZMJOIS-UHFFFAOYSA-N 3-benzylsulfanyl-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 MWDRNNBQZMJOIS-UHFFFAOYSA-N 0.000 description 1
- LCQKBMPCYNJEDX-UHFFFAOYSA-N 3-benzylsulfanyl-n-(4-butylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 LCQKBMPCYNJEDX-UHFFFAOYSA-N 0.000 description 1
- ACLDVKVSJJQBKX-UHFFFAOYSA-N 3-methylsulfanyl-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound N1C(SC)=NC(NC=2C=CC=CC=2)=N1 ACLDVKVSJJQBKX-UHFFFAOYSA-N 0.000 description 1
- AKEJFPPTCBLCNI-UHFFFAOYSA-N 4-[(5-anilino-1h-1,2,4-triazol-3-yl)sulfanyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1SC1=NC(NC=2C=CC=CC=2)=NN1 AKEJFPPTCBLCNI-UHFFFAOYSA-N 0.000 description 1
- HEXCBYUJQOAUPC-UHFFFAOYSA-N 4-[(5-anilino-1h-1,2,4-triazol-3-yl)sulfanylmethyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1CSC1=NC(NC=2C=CC=CC=2)=NN1 HEXCBYUJQOAUPC-UHFFFAOYSA-N 0.000 description 1
- SQGOTOWMDQJEQX-UHFFFAOYSA-N 5-[(3,4-difluorophenyl)methylsulfanyl]-1h-1,2,4-triazole Chemical compound C1=C(F)C(F)=CC=C1CSC1=NC=NN1 SQGOTOWMDQJEQX-UHFFFAOYSA-N 0.000 description 1
- XQJCTYHAHILFMI-UHFFFAOYSA-N 5-benzylsulfanyl-3-butyl-n-phenyl-1,2,4-triazol-3-amine Chemical compound N1=NC(SCC=2C=CC=CC=2)=NC1(CCCC)NC1=CC=CC=C1 XQJCTYHAHILFMI-UHFFFAOYSA-N 0.000 description 1
- BVGOXRXSKKCIMN-UHFFFAOYSA-N 5-benzylsulfanyl-3-methyl-n-phenyl-1,2,4-triazol-3-amine Chemical compound N1=NC(SCC=2C=CC=CC=2)=NC1(C)NC1=CC=CC=C1 BVGOXRXSKKCIMN-UHFFFAOYSA-N 0.000 description 1
- KUNJIRHWTPMYLJ-UHFFFAOYSA-N Cc1ccccc1Nc1n[nH]c(Sc2ccsc2)n1 Chemical compound Cc1ccccc1Nc1n[nH]c(Sc2ccsc2)n1 KUNJIRHWTPMYLJ-UHFFFAOYSA-N 0.000 description 1
- SHFCYUGHKCOUQC-UHFFFAOYSA-N N(c1n[nH]c(Sc2cccs2)n1)c1ccccc1-c1ccccc1 Chemical compound N(c1n[nH]c(Sc2cccs2)n1)c1ccccc1-c1ccccc1 SHFCYUGHKCOUQC-UHFFFAOYSA-N 0.000 description 1
- VQORZPNCMWANLF-UHFFFAOYSA-N N-phenyl-3-[(4-propylphenyl)methylsulfanyl]-1H-1,2,4-triazol-5-amine Chemical compound C1=CC(CCC)=CC=C1CSC1=NC(NC=2C=CC=CC=2)=NN1 VQORZPNCMWANLF-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010029113 Neovascularisation Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010038934 Retinopathy proliferative Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- OTKOJTJNYTWAOA-UHFFFAOYSA-N ethyl 5-[[5-(3-methylanilino)-1h-1,2,4-triazol-3-yl]sulfanylmethyl]furan-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC=C1CSC(N1)=NN=C1NC1=CC=CC(C)=C1 OTKOJTJNYTWAOA-UHFFFAOYSA-N 0.000 description 1
- 201000011066 hemangioma Diseases 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- QTGYDHFEPGNEGU-UHFFFAOYSA-N methyl 4-[[3-(2-methylbut-2-enylsulfanyl)-1h-1,2,4-triazol-5-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC(C)=CC)=N1 QTGYDHFEPGNEGU-UHFFFAOYSA-N 0.000 description 1
- UCZHLSRSQKTIHN-UHFFFAOYSA-N methyl 4-[[3-(cyclohexylmethylsulfanyl)-1h-1,2,4-triazol-5-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC2CCCCC2)=N1 UCZHLSRSQKTIHN-UHFFFAOYSA-N 0.000 description 1
- RRZWCHVEMCYHGB-UHFFFAOYSA-N methyl 4-[[3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC=2N=CC=CC=2)=N1 RRZWCHVEMCYHGB-UHFFFAOYSA-N 0.000 description 1
- PTHXUNVPFOFZAM-UHFFFAOYSA-N methyl 4-[[3-(pyridin-4-ylmethylsulfanyl)-1h-1,2,4-triazol-5-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC=2C=CN=CC=2)=N1 PTHXUNVPFOFZAM-UHFFFAOYSA-N 0.000 description 1
- ANVOVFUYYIRLNJ-UHFFFAOYSA-N methyl 4-[[3-[(2-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 ANVOVFUYYIRLNJ-UHFFFAOYSA-N 0.000 description 1
- VZSYRVYVFRPJRK-UHFFFAOYSA-N methyl 4-[[3-[(2-methyl-1,3-thiazol-4-yl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC=2N=C(C)SC=2)=N1 VZSYRVYVFRPJRK-UHFFFAOYSA-N 0.000 description 1
- KZOPEWSVPNZBQH-UHFFFAOYSA-N methyl 4-[[3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)C)=N1 KZOPEWSVPNZBQH-UHFFFAOYSA-N 0.000 description 1
- SNXPIVGONXCXNK-UHFFFAOYSA-N methyl 4-[[3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC2=NOC(C)=C2)=N1 SNXPIVGONXCXNK-UHFFFAOYSA-N 0.000 description 1
- UNLFIYZOCLVBFP-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-3-(2-methylbut-2-enylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC(C)=CC)=N1 UNLFIYZOCLVBFP-UHFFFAOYSA-N 0.000 description 1
- FYKHSYHOUUWSCN-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC=2N=CC=CC=2)=N1 FYKHSYHOUUWSCN-UHFFFAOYSA-N 0.000 description 1
- PLGJJNCKMDKQBB-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)OC)=N1 PLGJJNCKMDKQBB-UHFFFAOYSA-N 0.000 description 1
- IQQZGUVKPVMOEJ-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)C)=N1 IQQZGUVKPVMOEJ-UHFFFAOYSA-N 0.000 description 1
- KYGKRNVLBXEEEJ-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-3-[(4-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1CSC1=NC(NC=2C(=CC(OC)=CC=2)OC)=NN1 KYGKRNVLBXEEEJ-UHFFFAOYSA-N 0.000 description 1
- WAWPKOJXJYYSCS-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC2=NOC(C)=C2)=N1 WAWPKOJXJYYSCS-UHFFFAOYSA-N 0.000 description 1
- ACVRZPZGNXYTBR-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-3-(2-methylbut-2-enylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound N1C(SCC(C)=CC)=NC(NC=2C(=CC=CC=2C)C)=N1 ACVRZPZGNXYTBR-UHFFFAOYSA-N 0.000 description 1
- MLJMDUUZRBPWMK-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1CSC1=NC(NC=2C(=CC=CC=2C)C)=NN1 MLJMDUUZRBPWMK-UHFFFAOYSA-N 0.000 description 1
- CAICCYJPQXUFIO-UHFFFAOYSA-N n-(2-ethylphenyl)-3-(2-methylbut-2-enylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC(C)=CC)=N1 CAICCYJPQXUFIO-UHFFFAOYSA-N 0.000 description 1
- OXIPMRMWDIAJTB-UHFFFAOYSA-N n-(2-ethylphenyl)-3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC=2N=CC=CC=2)=N1 OXIPMRMWDIAJTB-UHFFFAOYSA-N 0.000 description 1
- CFEZTIYNQJZXKC-UHFFFAOYSA-N n-(2-ethylphenyl)-3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)OC)=N1 CFEZTIYNQJZXKC-UHFFFAOYSA-N 0.000 description 1
- VUUPTIGGMVSQHY-UHFFFAOYSA-N n-(2-ethylphenyl)-3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)C)=N1 VUUPTIGGMVSQHY-UHFFFAOYSA-N 0.000 description 1
- RPQRERNKSLNONL-UHFFFAOYSA-N n-(2-ethylphenyl)-3-[(4-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC=2C=CC(OC)=CC=2)=N1 RPQRERNKSLNONL-UHFFFAOYSA-N 0.000 description 1
- FEZUPAJBWMIXCS-UHFFFAOYSA-N n-(2-ethylphenyl)-3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC2=NOC(C)=C2)=N1 FEZUPAJBWMIXCS-UHFFFAOYSA-N 0.000 description 1
- UPOYVUAWABGETB-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-(2-methylbut-2-enylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC(C)=CC)=N1 UPOYVUAWABGETB-UHFFFAOYSA-N 0.000 description 1
- KWWQHSRMAJUYCS-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC=2N=CC=CC=2)=N1 KWWQHSRMAJUYCS-UHFFFAOYSA-N 0.000 description 1
- DBBMBQJYFXMMIA-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1CSC1=NC(NC=2C(=CC=CC=2)OC)=NN1 DBBMBQJYFXMMIA-UHFFFAOYSA-N 0.000 description 1
- LDIWXJMWGRIMOJ-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)C)=N1 LDIWXJMWGRIMOJ-UHFFFAOYSA-N 0.000 description 1
- ZFOVWBSGKDXNDS-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-[(4-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1CSC1=NC(NC=2C(=CC=CC=2)OC)=NN1 ZFOVWBSGKDXNDS-UHFFFAOYSA-N 0.000 description 1
- UPEBCSRNDLPBOF-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC2=NOC(C)=C2)=N1 UPEBCSRNDLPBOF-UHFFFAOYSA-N 0.000 description 1
- UVWHIUPPMUAIDU-UHFFFAOYSA-N n-(2-methylphenyl)-3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1NC1=NNC(SCC=2N=CC=CC=2)=N1 UVWHIUPPMUAIDU-UHFFFAOYSA-N 0.000 description 1
- YVIMUISILVLLLG-UHFFFAOYSA-N n-(2-methylphenyl)-3-(pyridin-4-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1NC1=NNC(SCC=2C=CN=CC=2)=N1 YVIMUISILVLLLG-UHFFFAOYSA-N 0.000 description 1
- SFZZYMYEZZFERE-UHFFFAOYSA-N n-(2-methylphenyl)-3-[(2-methyl-1,3-thiazol-4-yl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound S1C(C)=NC(CSC=2NN=C(NC=3C(=CC=CC=3)C)N=2)=C1 SFZZYMYEZZFERE-UHFFFAOYSA-N 0.000 description 1
- DGNJJUHFOODKOO-UHFFFAOYSA-N n-(2-methylphenyl)-3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1CSC1=NC(NC=2C(=CC=CC=2)C)=NN1 DGNJJUHFOODKOO-UHFFFAOYSA-N 0.000 description 1
- SQILXNVEXGLMHS-UHFFFAOYSA-N n-(2-phenylphenyl)-3-(pyridin-4-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C=1C=NC=CC=1CSC(NN=1)=NC=1NC1=CC=CC=C1C1=CC=CC=C1 SQILXNVEXGLMHS-UHFFFAOYSA-N 0.000 description 1
- GFDVQJXJKRNGII-UHFFFAOYSA-N n-(2-propan-2-ylphenyl)-3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NNC(SCC=2N=CC=CC=2)=N1 GFDVQJXJKRNGII-UHFFFAOYSA-N 0.000 description 1
- KDKMMMBIRZYWHT-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-3-(2-methylbut-2-enylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NNC(SCC(C)=CC)=N1 KDKMMMBIRZYWHT-UHFFFAOYSA-N 0.000 description 1
- XIBHPGXOPSUQJK-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NNC(SCC=2N=CC=CC=2)=N1 XIBHPGXOPSUQJK-UHFFFAOYSA-N 0.000 description 1
- RLCZVJZYWZGSPD-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-3-(pyridin-4-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NNC(SCC=2C=CN=CC=2)=N1 RLCZVJZYWZGSPD-UHFFFAOYSA-N 0.000 description 1
- PXCZJDIODUVODT-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-3-[(2-methyl-1,3-thiazol-4-yl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NNC(SCC=2N=C(C)SC=2)=N1 PXCZJDIODUVODT-UHFFFAOYSA-N 0.000 description 1
- HBVGHXDAASJJML-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)C)=N1 HBVGHXDAASJJML-UHFFFAOYSA-N 0.000 description 1
- CKMXHRNOTVAGKO-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NNC(SCC2=NOC(C)=C2)=N1 CKMXHRNOTVAGKO-UHFFFAOYSA-N 0.000 description 1
- HUPAMMFGBBNTDA-UHFFFAOYSA-N n-(3-benzylsulfanyl-1h-1,2,4-triazol-5-yl)pyridin-3-amine Chemical compound C=1C=CC=CC=1CSC(NN=1)=NC=1NC1=CC=CN=C1 HUPAMMFGBBNTDA-UHFFFAOYSA-N 0.000 description 1
- JRRZDTIMLQRDNU-UHFFFAOYSA-N n-(3-methylphenyl)-3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2N=C(SCC=3N=CC=CC=3)NN=2)=C1 JRRZDTIMLQRDNU-UHFFFAOYSA-N 0.000 description 1
- NODRESNENAQUAW-UHFFFAOYSA-N n-(3-methylphenyl)-3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2N=C(SCC=3C(=CC=CC=3)C)NN=2)=C1 NODRESNENAQUAW-UHFFFAOYSA-N 0.000 description 1
- CZERQPBVKPTFCA-UHFFFAOYSA-N n-(4-butylphenyl)-3-(2-methylbut-2-enylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC(C)=CC)=N1 CZERQPBVKPTFCA-UHFFFAOYSA-N 0.000 description 1
- BGIZLGWWIHEKBN-UHFFFAOYSA-N n-(4-butylphenyl)-3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC=2N=CC=CC=2)=N1 BGIZLGWWIHEKBN-UHFFFAOYSA-N 0.000 description 1
- DWILQQVVCKZQPG-UHFFFAOYSA-N n-(4-butylphenyl)-3-[(2-chlorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)Cl)=N1 DWILQQVVCKZQPG-UHFFFAOYSA-N 0.000 description 1
- HXIORMYCXSONIM-UHFFFAOYSA-N n-(4-butylphenyl)-3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)OC)=N1 HXIORMYCXSONIM-UHFFFAOYSA-N 0.000 description 1
- UDPAGNHXCASARS-UHFFFAOYSA-N n-(4-butylphenyl)-3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)C)=N1 UDPAGNHXCASARS-UHFFFAOYSA-N 0.000 description 1
- GGTMQUNGZYSXNW-UHFFFAOYSA-N n-(4-butylphenyl)-3-[(4-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC=2C=CC(OC)=CC=2)=N1 GGTMQUNGZYSXNW-UHFFFAOYSA-N 0.000 description 1
- BQMVMPBSRPFDEJ-UHFFFAOYSA-N n-(4-butylphenyl)-3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC2=NOC(C)=C2)=N1 BQMVMPBSRPFDEJ-UHFFFAOYSA-N 0.000 description 1
- QYEBURWLDVZQPN-UHFFFAOYSA-N n-(4-chlorophenyl)-3-(2-methylbut-2-enylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound N1C(SCC(C)=CC)=NC(NC=2C=CC(Cl)=CC=2)=N1 QYEBURWLDVZQPN-UHFFFAOYSA-N 0.000 description 1
- IKCWOQMEZGBKOA-UHFFFAOYSA-N n-(4-chlorophenyl)-3-(cyclohexylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NNC(SCC2CCCCC2)=N1 IKCWOQMEZGBKOA-UHFFFAOYSA-N 0.000 description 1
- IKHKTFXDDCKPPU-UHFFFAOYSA-N n-(4-chlorophenyl)-3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NNC(SCC=2N=CC=CC=2)=N1 IKHKTFXDDCKPPU-UHFFFAOYSA-N 0.000 description 1
- JNLUFMFMIAITLU-UHFFFAOYSA-N n-(4-chlorophenyl)-3-(pyridin-4-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NNC(SCC=2C=CN=CC=2)=N1 JNLUFMFMIAITLU-UHFFFAOYSA-N 0.000 description 1
- APMOPWAIYDLBQX-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1CSC1=NC(NC=2C=CC(Cl)=CC=2)=NN1 APMOPWAIYDLBQX-UHFFFAOYSA-N 0.000 description 1
- REUVMANHNAXNOC-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[(2-methyl-1,3-thiazol-4-yl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound S1C(C)=NC(CSC=2NN=C(NC=3C=CC(Cl)=CC=3)N=2)=C1 REUVMANHNAXNOC-UHFFFAOYSA-N 0.000 description 1
- QLRRAOOBBNVNNP-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1CSC1=NC(NC=2C=CC(Cl)=CC=2)=NN1 QLRRAOOBBNVNNP-UHFFFAOYSA-N 0.000 description 1
- HBOYMSMNHPPYJJ-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound O1C(C)=CC(CSC=2NN=C(NC=3C=CC(Cl)=CC=3)N=2)=N1 HBOYMSMNHPPYJJ-UHFFFAOYSA-N 0.000 description 1
- ACWNWGDOJFHQNC-UHFFFAOYSA-N n-(4-methoxy-2-methylphenyl)-3-(2-methylbut-2-enylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC(C)=CC)=N1 ACWNWGDOJFHQNC-UHFFFAOYSA-N 0.000 description 1
- OGIWPPJARRANFC-UHFFFAOYSA-N n-(4-methoxy-2-methylphenyl)-3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC=2N=CC=CC=2)=N1 OGIWPPJARRANFC-UHFFFAOYSA-N 0.000 description 1
- SCYVUPGXYIHIGJ-UHFFFAOYSA-N n-(4-methoxy-2-methylphenyl)-3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)OC)=N1 SCYVUPGXYIHIGJ-UHFFFAOYSA-N 0.000 description 1
- GLETYIBOOALWAS-UHFFFAOYSA-N n-(4-methoxy-2-methylphenyl)-3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)C)=N1 GLETYIBOOALWAS-UHFFFAOYSA-N 0.000 description 1
- JSCMJXUBXRWGKO-UHFFFAOYSA-N n-(4-methoxy-2-methylphenyl)-3-[(4-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1CSC1=NC(NC=2C(=CC(OC)=CC=2)C)=NN1 JSCMJXUBXRWGKO-UHFFFAOYSA-N 0.000 description 1
- JMTVXADJJYDTCO-UHFFFAOYSA-N n-(4-methoxy-2-methylphenyl)-3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC2=NOC(C)=C2)=N1 JMTVXADJJYDTCO-UHFFFAOYSA-N 0.000 description 1
- LOIHQCZHTDBLKQ-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-(2-methylbut-2-enylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC(C)=CC)=N1 LOIHQCZHTDBLKQ-UHFFFAOYSA-N 0.000 description 1
- VBPOLWXUEVAPAM-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC=2N=CC=CC=2)=N1 VBPOLWXUEVAPAM-UHFFFAOYSA-N 0.000 description 1
- XAADYOTWRBKDNL-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-(pyridin-4-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC=2C=CN=CC=2)=N1 XAADYOTWRBKDNL-UHFFFAOYSA-N 0.000 description 1
- ARMNLDVQMJNAOG-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-[(2-methyl-1,3-thiazol-4-yl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC=2N=C(C)SC=2)=N1 ARMNLDVQMJNAOG-UHFFFAOYSA-N 0.000 description 1
- UCYCVBLWWVIWQD-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)C)=N1 UCYCVBLWWVIWQD-UHFFFAOYSA-N 0.000 description 1
- FSBPBGNXLVBZNI-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC2=NOC(C)=C2)=N1 FSBPBGNXLVBZNI-UHFFFAOYSA-N 0.000 description 1
- TZZXUFBSLJVBTR-UHFFFAOYSA-N n-(4-methylphenyl)-3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NNC(SCC=2N=CC=CC=2)=N1 TZZXUFBSLJVBTR-UHFFFAOYSA-N 0.000 description 1
- RBIHDOVUAYCXNR-UHFFFAOYSA-N n-(4-methylphenyl)-3-(pyridin-4-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NNC(SCC=2C=CN=CC=2)=N1 RBIHDOVUAYCXNR-UHFFFAOYSA-N 0.000 description 1
- UOZJYTRYFBCHCN-UHFFFAOYSA-N n-(4-methylphenyl)-3-[(2-methyl-1,3-thiazol-4-yl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound S1C(C)=NC(CSC=2NN=C(NC=3C=CC(C)=CC=3)N=2)=C1 UOZJYTRYFBCHCN-UHFFFAOYSA-N 0.000 description 1
- GSJJLAZCTRDKSS-UHFFFAOYSA-N n-(4-methylphenyl)-3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)C)=N1 GSJJLAZCTRDKSS-UHFFFAOYSA-N 0.000 description 1
- DKBNUXIEDDMITE-UHFFFAOYSA-N n-[3-(2-methylbut-2-enylsulfanyl)-1h-1,2,4-triazol-5-yl]pyridin-3-amine Chemical compound N1C(SCC(C)=CC)=NC(NC=2C=NC=CC=2)=N1 DKBNUXIEDDMITE-UHFFFAOYSA-N 0.000 description 1
- KHNIMEIHBMRLSV-UHFFFAOYSA-N n-[3-(cyclohexylmethylsulfanyl)-1h-1,2,4-triazol-5-yl]pyridin-3-amine Chemical compound C1CCCCC1CSC(NN=1)=NC=1NC1=CC=CN=C1 KHNIMEIHBMRLSV-UHFFFAOYSA-N 0.000 description 1
- LJYQBCYDGPEXAJ-UHFFFAOYSA-N n-[3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-yl]pyridin-3-amine Chemical compound C=1C=CC=NC=1CSC(NN=1)=NC=1NC1=CC=CN=C1 LJYQBCYDGPEXAJ-UHFFFAOYSA-N 0.000 description 1
- SQQSUMIEMWCUGN-UHFFFAOYSA-N n-[3-(pyridin-4-ylmethylsulfanyl)-1h-1,2,4-triazol-5-yl]pyridin-3-amine Chemical compound C=1C=NC=CC=1CSC(NN=1)=NC=1NC1=CC=CN=C1 SQQSUMIEMWCUGN-UHFFFAOYSA-N 0.000 description 1
- QTVZODFEDWSCGZ-UHFFFAOYSA-N n-[3-[(2-methyl-1,3-thiazol-4-yl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]pyridin-3-amine Chemical compound S1C(C)=NC(CSC=2NN=C(NC=3C=NC=CC=3)N=2)=C1 QTVZODFEDWSCGZ-UHFFFAOYSA-N 0.000 description 1
- HJPZWWYALIMYCP-UHFFFAOYSA-N n-[3-[(2-methylphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]pyridin-3-amine Chemical compound CC1=CC=CC=C1CSC1=NC(NC=2C=NC=CC=2)=NN1 HJPZWWYALIMYCP-UHFFFAOYSA-N 0.000 description 1
- AACDUZATGDPUNH-UHFFFAOYSA-N n-[3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]pyridin-3-amine Chemical compound O1C(C)=CC(CSC=2NN=C(NC=3C=NC=CC=3)N=2)=N1 AACDUZATGDPUNH-UHFFFAOYSA-N 0.000 description 1
- RMPZMLWBDBTEMQ-UHFFFAOYSA-N n-[4-[(5-anilino-1h-1,2,4-triazol-3-yl)sulfanylmethyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CSC1=NC(NC=2C=CC=CC=2)=NN1 RMPZMLWBDBTEMQ-UHFFFAOYSA-N 0.000 description 1
- BRXROFPDDHOZMB-UHFFFAOYSA-N n-phenyl-3-(1-phenylethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C=1C=CC=CC=1C(C)SC(NN=1)=NC=1NC1=CC=CC=C1 BRXROFPDDHOZMB-UHFFFAOYSA-N 0.000 description 1
- KLPYJLQTNSIDDN-UHFFFAOYSA-N n-phenyl-3-(2-phenylethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound N=1C(NC=2C=CC=CC=2)=NNC=1SCCC1=CC=CC=C1 KLPYJLQTNSIDDN-UHFFFAOYSA-N 0.000 description 1
- JTWLGXZNCKQFMS-UHFFFAOYSA-N n-phenyl-3-(pyridin-2-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C=1C=CC=NC=1CSC(NN=1)=NC=1NC1=CC=CC=C1 JTWLGXZNCKQFMS-UHFFFAOYSA-N 0.000 description 1
- OOUAOHZMQRNZLU-UHFFFAOYSA-N n-phenyl-3-(pyridin-4-ylmethylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C=1C=NC=CC=1CSC(NN=1)=NC=1NC1=CC=CC=C1 OOUAOHZMQRNZLU-UHFFFAOYSA-N 0.000 description 1
- GBFGPNJGRVHHGX-UHFFFAOYSA-N n-phenyl-3-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1CSC1=NC(NC=2C=CC=CC=2)=NN1 GBFGPNJGRVHHGX-UHFFFAOYSA-N 0.000 description 1
- BYHCYCFRDSXURW-UHFFFAOYSA-N n-phenyl-3-quinolin-8-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound N=1NC(SC=2C3=NC=CC=C3C=CC=2)=NC=1NC1=CC=CC=C1 BYHCYCFRDSXURW-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- NHDZOMNMBJBILW-UHFFFAOYSA-N s-(5-anilino-1h-1,2,4-triazol-3-yl) pentanethioate Chemical compound N1C(SC(=O)CCCC)=NC(NC=2C=CC=CC=2)=N1 NHDZOMNMBJBILW-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15728699P | 1999-10-01 | 1999-10-01 | |
| US60/157,286 | 1999-10-01 | ||
| PCT/US2000/026951 WO2001024796A1 (en) | 1999-10-01 | 2000-09-29 | 1,2,4-triazole derivatives, composition, process of making and methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003510359A JP2003510359A (ja) | 2003-03-18 |
| JP2003510359A5 true JP2003510359A5 (enExample) | 2007-11-22 |
Family
ID=22563095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001527795A Pending JP2003510359A (ja) | 1999-10-01 | 2000-09-29 | 化合物および方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7304082B2 (enExample) |
| EP (1) | EP1223932A4 (enExample) |
| JP (1) | JP2003510359A (enExample) |
| AU (1) | AU7989400A (enExample) |
| WO (1) | WO2001024796A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002078697A1 (en) * | 2001-03-29 | 2002-10-10 | Smithkline Beecham Corporation | Compounds and methods |
| WO2003083068A2 (en) * | 2002-03-27 | 2003-10-09 | Smithkline Beecham Corporation | Compounds and methods |
| AR040847A1 (es) * | 2002-08-09 | 2005-04-20 | Astrazeneca Ab | 1,2,4-oxadiazoles como moduladores de receptores de glutamato metabotropicos, para el tratamiento de desordenes neurologicos y psiquiatricos |
| FR2862060A1 (fr) * | 2003-11-06 | 2005-05-13 | Galderma Res & Dev | Procede de synthese en phase solide de composes de types sulfures de diaryle. |
| AU2007267803B2 (en) * | 2006-05-25 | 2011-08-25 | Synta Pharmaceuticals Corp. | Method for treating non-Hodgkin's lymphoma |
| WO2009003110A2 (en) | 2007-06-26 | 2008-12-31 | Children's Medical Center Corporation | Metap-2 inhibitor polymersomes for therapeutic administration |
| EP2486004B1 (en) | 2009-10-09 | 2017-05-03 | Zafgen, Inc. | Sulphone compounds for use in the treatment of obesity |
| US8815309B2 (en) | 2010-01-08 | 2014-08-26 | Zafgen, Inc. | Methods of treating a subject with benign prostate hyperplasia |
| US20130023513A1 (en) | 2010-01-12 | 2013-01-24 | Hughes Thomas E | Methods and Compositions for Treating Cardiovascular Disorders |
| WO2011127304A2 (en) | 2010-04-07 | 2011-10-13 | Zafgen Corporation | Methods of treating an overweight subject |
| EP2560640A1 (en) | 2010-04-19 | 2013-02-27 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a hsp90 inhibitory compounds and a egfr inhibitor |
| CN103249735B (zh) * | 2010-07-22 | 2016-04-06 | 扎夫根股份有限公司 | 三环化合物及其制备和使用方法 |
| US20140073691A1 (en) | 2010-11-10 | 2014-03-13 | Zafgen, Inc. | Methods and composition for Treating Thyroid Hormone Related Disorders |
| US20130316994A1 (en) | 2010-11-29 | 2013-11-28 | Zafgen, Inc. | Methods of Reducing Risk of Hepatobiliary Dysfunction During Rapid Weight Loss with METAP-2 Inhibitors |
| US9189078B2 (en) | 2010-12-20 | 2015-11-17 | Apple Inc. | Enhancing keycap legend visibility with optical components |
| KR20140006888A (ko) | 2011-01-26 | 2014-01-16 | 자프겐 인크. | 테트라졸화합물, 그리고, 이를 제조하는 방법 및 이를 이용하는 방법 |
| CA2835261C (en) | 2011-05-06 | 2019-06-04 | Zafgen, Inc. | Partially saturated tricyclic compounds and methods of making and using same |
| AU2012253759B2 (en) | 2011-05-06 | 2016-01-21 | Zafgen Inc. | Tricyclic sulfonamide compounds and methods of making and using same |
| BR112013028666A2 (pt) | 2011-05-06 | 2017-08-08 | Zafgen Inc | compostos de pirazolo sulfonamida tricícilos e métodos para fazer e usar o mesmo |
| EP2763671A2 (en) | 2011-10-03 | 2014-08-13 | Zafgen, Inc. | Methods of treating age related disorders |
| WO2013067162A1 (en) | 2011-11-02 | 2013-05-10 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of hsp90 inhibitors with topoisomerase i inhibitors |
| JP2014534228A (ja) | 2011-11-02 | 2014-12-18 | シンタ ファーマシューティカルズ コーポレーション | 白金含有剤とｈｓｐ９０阻害剤の組合せ療法 |
| EP2780010A1 (en) | 2011-11-14 | 2014-09-24 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with braf inhibitors |
| MX2014008706A (es) | 2012-01-18 | 2015-03-05 | Zafgen Inc | Compuestos tricíclicos de sulfonamida y métodos para elaborarlos y usarlos. |
| JP2015509102A (ja) | 2012-01-18 | 2015-03-26 | ザフゲン，インコーポレイテッド | 三環式スルホン化合物並びにその作製および使用方法 |
| AU2013259617A1 (en) | 2012-05-08 | 2014-11-27 | Zafgen, Inc. | Treating hypothalamic obesity with MetAP2 inhibitors |
| MX356755B (es) | 2012-05-09 | 2018-06-11 | Zafgen Inc | Compuestos de tipo fumagilol y metodos para su elaboración y uso. |
| NZ707773A (en) | 2012-11-05 | 2019-05-31 | Zafgen Inc | Methods of treating liver diseases |
| JP2015536981A (ja) | 2012-11-05 | 2015-12-24 | ザフゲン，インコーポレイテッド | 三環式化合物ならびにその製造および使用方法 |
| BR112015010223A2 (pt) | 2012-11-05 | 2017-07-11 | Zafgen Inc | compostos tricíclicos para o uso no tratamento e/ou controle de obesidade |
| CN105228610A (zh) | 2013-03-14 | 2016-01-06 | 扎夫根股份有限公司 | 治疗肾疾病和其它病症的方法 |
| WO2015089800A1 (en) | 2013-12-19 | 2015-06-25 | Eli Lilly And Company | Fluorophenyl pyrazol compounds |
| EP3154634B1 (en) * | 2014-06-12 | 2021-02-24 | Université de Lille | Imidazol- or 1,2,4-triazol-derivatives and their use |
| CN106432255A (zh) | 2015-08-11 | 2017-02-22 | 扎夫根公司 | 烟曲霉素醇螺环化合物和制备和使用其的方法 |
| AR105671A1 (es) | 2015-08-11 | 2017-10-25 | Zafgen Inc | Compuestos heterocíclicos de fumagillol y sus métodos de elaboración y uso |
| MA52489A (fr) * | 2018-05-04 | 2021-03-10 | Inflazome Ltd | Nouveaux composés |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55120571A (en) * | 1979-03-02 | 1980-09-17 | Glaxo Group Ltd | Heterocyclic derivative |
| CH655104A5 (fr) * | 1980-02-28 | 1986-03-27 | Glaxo Group Ltd | Derives heterocycliques triazoliques, procedes pour leur preparation et compositions pharmaceutiques les comportant. |
| HU191475B (en) * | 1982-09-01 | 1987-02-27 | Gyogyszerkutato Intezet | Process for producing new acylized 1,2,4-triazole derivatives |
| US4760448A (en) * | 1987-05-04 | 1988-07-26 | Sencore, Inc. | Method of measuring amplitude variations of a video carrier and apparatus therefor |
| JPH01160972A (ja) * | 1987-12-18 | 1989-06-23 | Tsumura & Co | １，２，４−トリアゾール誘導体及びそれを有効成分として含有する抗潰瘍剤 |
| DE4142366A1 (de) | 1991-07-15 | 1993-06-24 | Thomae Gmbh Dr K | Phenylalkylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| GB9207396D0 (en) | 1992-04-03 | 1992-05-13 | Merck Sharp & Dohme | Therapeutic agents |
| DE4424787A1 (de) | 1994-07-14 | 1996-01-18 | Bayer Ag | Substituierte Aryliminoheterocyclen |
| DE4425144A1 (de) | 1994-07-15 | 1996-01-18 | Basf Ag | Triazolverbindungen und deren Verwendung |
| WO1996016971A1 (de) * | 1994-11-29 | 1996-06-06 | Lonza Ag | Verfahren zur herstellung optisch aktiver metallocenylphosphine |
| US5798374A (en) * | 1995-06-07 | 1998-08-25 | Sugen Inc. | Methods of inhibiting phosphatase activity and treatment of disorders associated therewith |
| US5760246A (en) * | 1996-12-17 | 1998-06-02 | Biller; Scott A. | Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method |
| US6207704B1 (en) * | 1997-06-09 | 2001-03-27 | Massachusetts Institute Of Technology | Type 2 methionine aminopeptidase [MetAP2] inhibitors and uses thereof |
| DE19922443A1 (de) * | 1999-05-07 | 2000-11-09 | Basf Ag | Verwendung von Dopamin-D3-Rezeptorliganden zur Herstellung von Arzneimittel für die Behandlung von Nierenfunktionsstörungen |
| DE19921567A1 (de) * | 1999-05-11 | 2000-11-16 | Basf Ag | Verwendung von Phthalazine-Derivaten |
| WO2001036404A1 (en) | 1999-11-19 | 2001-05-25 | Smithkline Beecham Corporation | Compounds and methods |
| HN2001000008A (es) * | 2000-01-21 | 2003-12-11 | Inc Agouron Pharmaceuticals | Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo |
| AU2001231154A1 (en) * | 2000-01-24 | 2001-07-31 | Adherex Technologies Inc. | Peptidomimetic modulators of cell adhesion |
| AU2001253418A1 (en) * | 2000-04-12 | 2001-10-30 | Smith Kline Beecham Corporation | Compounds and methods |
| WO2002005804A1 (en) | 2000-07-19 | 2002-01-24 | Smithkline Beecham Corporation | Compounds and methods |
| JP2005506299A (ja) * | 2001-03-29 | 2005-03-03 | スミスクライン・ビーチャム・コーポレイション | 化合物および方法 |
| JP2004525942A (ja) * | 2001-03-29 | 2004-08-26 | スミスクライン・ビーチャム・コーポレイション | 化合物および方法 |
| JP2004535377A (ja) | 2001-04-03 | 2004-11-25 | スミスクライン・ビーチャム・コーポレイション | Ｍｅｔａｐ２を阻害する方法 |
| WO2003031434A1 (en) * | 2001-10-12 | 2003-04-17 | Smith Kline Beecham Corporation | Compounds and methods |
| AU2002359694A1 (en) | 2001-12-14 | 2003-06-30 | Smithkline Beecham Corporation | Compounds and methods |
| JP2003281388A (ja) * | 2002-03-25 | 2003-10-03 | Hitachi Ltd | 自動取引装置 |
| WO2003083068A2 (en) * | 2002-03-27 | 2003-10-09 | Smithkline Beecham Corporation | Compounds and methods |
| US20040116490A1 (en) * | 2002-03-28 | 2004-06-17 | Marino Jr. Joseph P. | Compounds and methods |
-
2000
- 2000-09-29 AU AU79894/00A patent/AU7989400A/en not_active Abandoned
- 2000-09-29 WO PCT/US2000/026951 patent/WO2001024796A1/en not_active Ceased
- 2000-09-29 EP EP00970527A patent/EP1223932A4/en not_active Withdrawn
- 2000-09-29 JP JP2001527795A patent/JP2003510359A/ja active Pending
-
2005
- 2005-07-21 US US11/186,519 patent/US7304082B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2004520292A5 (enExample) | ||
| RU2006127575A (ru) | Соединение триазола и их применение в качестве антагонистов метаботропного рецептора глутамата | |
| JP2019077725A5 (enExample) | ||
| JP2020516671A5 (enExample) | ||
| JP2007523181A5 (enExample) | ||
| JP2005511608A5 (enExample) | ||
| US20090054491A1 (en) | Use | |
| RU2006127572A (ru) | Полигетероциклические соединения и их применение в качестве антагонистов метаботропного рецептора глутамата | |
| JP2010505809A5 (enExample) | ||
| JP2009519965A5 (enExample) | ||
| JP2007523182A5 (enExample) | ||
| RU2004117545A (ru) | Аминопиримидины и пиридины | |
| JP2007511485A5 (enExample) | ||
| JP2006524686A5 (enExample) | ||
| RU2009111113A (ru) | Мидуляторы mglur5 | |
| JP2006506380A5 (enExample) | ||
| JP2006507355A5 (enExample) | ||
| JP2005509632A5 (enExample) | ||
| JP2011527675A5 (enExample) | ||
| JP2002505286A5 (enExample) | ||
| JP2004525184A5 (enExample) | ||
| JP2004524279A5 (enExample) | ||
| JP2009503103A (ja) | アリールピリジン及びその使用方法 | |
| JP2004520424A5 (enExample) | ||
| CA2465757A1 (en) | Triazole derivatives as cyclooxygenase (cox) inhibitors |