JP2006524686A5 - - Google Patents
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- JP2006524686A5 JP2006524686A5 JP2006508031A JP2006508031A JP2006524686A5 JP 2006524686 A5 JP2006524686 A5 JP 2006524686A5 JP 2006508031 A JP2006508031 A JP 2006508031A JP 2006508031 A JP2006508031 A JP 2006508031A JP 2006524686 A5 JP2006524686 A5 JP 2006524686A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- thione
- triazole
- phenyl
- chlorobenzyl
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000004414 alkyl thio group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- ILUVIMSFVCQFEJ-UHFFFAOYSA-N 3-[(2-chloro-6-fluoro-3-methylphenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=CC=C(F)C(CC=2N(C(=S)NN=2)C=2C=CC=CC=2)=C1Cl ILUVIMSFVCQFEJ-UHFFFAOYSA-N 0.000 claims 3
- -1 NR 8 R 9 Chemical group 0.000 claims 3
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 150000003583 thiosemicarbazides Chemical class 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- FQLPBDOZNFNHGP-UHFFFAOYSA-N 1-[3-[3-[(2-chlorophenyl)methyl]-5-sulfanylidene-1h-1,2,4-triazol-4-yl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(N2C(NN=C2CC=2C(=CC=CC=2)Cl)=S)=C1 FQLPBDOZNFNHGP-UHFFFAOYSA-N 0.000 claims 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- SSVVTNOZSRBIKE-UHFFFAOYSA-N 3-[(2,3-dichlorophenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound ClC1=CC=CC(CC=2N(C(=S)NN=2)C=2C=CC=CC=2)=C1Cl SSVVTNOZSRBIKE-UHFFFAOYSA-N 0.000 claims 2
- NOPYAEFNZPMSJU-UHFFFAOYSA-N 3-[(2,3-dimethoxyphenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=CC(CC=2N(C(=S)NN=2)C=2C=CC=CC=2)=C1OC NOPYAEFNZPMSJU-UHFFFAOYSA-N 0.000 claims 2
- AFZQCRNXYKOEAR-UHFFFAOYSA-N 3-[(2,5-dimethoxyphenyl)methyl]-4-(3,4,5-trimethoxyphenyl)-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=C(OC)C(CC=2N(C(=S)NN=2)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 AFZQCRNXYKOEAR-UHFFFAOYSA-N 0.000 claims 2
- IRDZYSFFLNUIHF-UHFFFAOYSA-N 3-[(2,5-dimethoxyphenyl)methyl]-4-(3-methylsulfanylphenyl)-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=C(OC)C(CC=2N(C(=S)NN=2)C=2C=C(SC)C=CC=2)=C1 IRDZYSFFLNUIHF-UHFFFAOYSA-N 0.000 claims 2
- QPSZUCMUTAIOAF-UHFFFAOYSA-N 3-[(2,5-dimethoxyphenyl)methyl]-4-(4-iodophenyl)-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=C(OC)C(CC=2N(C(=S)NN=2)C=2C=CC(I)=CC=2)=C1 QPSZUCMUTAIOAF-UHFFFAOYSA-N 0.000 claims 2
- XKKGDLHIDGBDPF-UHFFFAOYSA-N 3-[(2,5-dimethoxyphenyl)methyl]-4-(4-piperidin-1-ylsulfonylphenyl)-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=C(OC)C(CC=2N(C(=S)NN=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCCCC2)=C1 XKKGDLHIDGBDPF-UHFFFAOYSA-N 0.000 claims 2
- PFBXTQRUUAMZBT-UHFFFAOYSA-N 3-[(2,6-dimethylphenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=CC=CC(C)=C1CC1=NNC(=S)N1C1=CC=CC=C1 PFBXTQRUUAMZBT-UHFFFAOYSA-N 0.000 claims 2
- PFJUYXTUUIGGDO-UHFFFAOYSA-N 3-[(2-bromo-5-methylphenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=CC=C(Br)C(CC=2N(C(=S)NN=2)C=2C=CC=CC=2)=C1 PFJUYXTUUIGGDO-UHFFFAOYSA-N 0.000 claims 2
- DOPNNIJPDROHOB-UHFFFAOYSA-N 3-[(2-bromophenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound BrC1=CC=CC=C1CC1=NNC(=S)N1C1=CC=CC=C1 DOPNNIJPDROHOB-UHFFFAOYSA-N 0.000 claims 2
- LCVYZHJOKKFBDH-UHFFFAOYSA-N 3-[(2-butoxyphenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCOC1=CC=CC=C1CC1=NNC(=S)N1C1=CC=CC=C1 LCVYZHJOKKFBDH-UHFFFAOYSA-N 0.000 claims 2
- RDUOCWCXSJWWQI-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-(2-ethoxyphenyl)-1h-1,2,4-triazole-5-thione Chemical compound CCOC1=CC=CC=C1N1C(=S)NN=C1CC1=CC=CC=C1Cl RDUOCWCXSJWWQI-UHFFFAOYSA-N 0.000 claims 2
- ARVGOXXQWHHIEV-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-(2-methoxy-5-methylphenyl)-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=C(C)C=C1N1C(=S)NN=C1CC1=CC=CC=C1Cl ARVGOXXQWHHIEV-UHFFFAOYSA-N 0.000 claims 2
- BZAXXDFKWPOPKQ-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-(2-methoxyphenyl)-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=CC=C1N1C(=S)NN=C1CC1=CC=CC=C1Cl BZAXXDFKWPOPKQ-UHFFFAOYSA-N 0.000 claims 2
- ARAGFPWJUWXPFP-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-(2-methylphenyl)-1h-1,2,4-triazole-5-thione Chemical compound CC1=CC=CC=C1N1C(=S)NN=C1CC1=CC=CC=C1Cl ARAGFPWJUWXPFP-UHFFFAOYSA-N 0.000 claims 2
- ZUXPBKANVDWKKY-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-(3-methoxyphenyl)-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=CC(N2C(NN=C2CC=2C(=CC=CC=2)Cl)=S)=C1 ZUXPBKANVDWKKY-UHFFFAOYSA-N 0.000 claims 2
- ILECFXMUJYCDAH-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-(3-methylphenyl)-1h-1,2,4-triazole-5-thione Chemical compound CC1=CC=CC(N2C(NN=C2CC=2C(=CC=CC=2)Cl)=S)=C1 ILECFXMUJYCDAH-UHFFFAOYSA-N 0.000 claims 2
- RHJSVFTUOAWVHH-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-(4-fluorophenyl)-1h-1,2,4-triazole-5-thione Chemical compound C1=CC(F)=CC=C1N1C(=S)NN=C1CC1=CC=CC=C1Cl RHJSVFTUOAWVHH-UHFFFAOYSA-N 0.000 claims 2
- XKZKTFSXESQQNG-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-(4-methylphenyl)-1h-1,2,4-triazole-5-thione Chemical compound C1=CC(C)=CC=C1N1C(=S)NN=C1CC1=CC=CC=C1Cl XKZKTFSXESQQNG-UHFFFAOYSA-N 0.000 claims 2
- LHIXMHUMAYGYCI-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-[3-(hydroxymethyl)phenyl]-1h-1,2,4-triazole-5-thione Chemical compound OCC1=CC=CC(N2C(NN=C2CC=2C(=CC=CC=2)Cl)=S)=C1 LHIXMHUMAYGYCI-UHFFFAOYSA-N 0.000 claims 2
- FGBWZHZMDZYANY-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound ClC1=CC=CC=C1CC1=NNC(=S)N1C1=CC=CC=C1 FGBWZHZMDZYANY-UHFFFAOYSA-N 0.000 claims 2
- GISGOKKFTWBOHA-UHFFFAOYSA-N 3-[(2-fluorophenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound FC1=CC=CC=C1CC1=NNC(=S)N1C1=CC=CC=C1 GISGOKKFTWBOHA-UHFFFAOYSA-N 0.000 claims 2
- RIICDYWUQHGKID-UHFFFAOYSA-N 3-[(2-methoxyphenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=CC=C1CC1=NNC(=S)N1C1=CC=CC=C1 RIICDYWUQHGKID-UHFFFAOYSA-N 0.000 claims 2
- HHFBHYFKFCXLPI-UHFFFAOYSA-N 3-[(2-methylphenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=CC=CC=C1CC1=NNC(=S)N1C1=CC=CC=C1 HHFBHYFKFCXLPI-UHFFFAOYSA-N 0.000 claims 2
- BWOFOFNNUSUDDC-UHFFFAOYSA-N 4-(2-chlorophenyl)-3-[(2-chlorophenyl)methyl]-1h-1,2,4-triazole-5-thione Chemical compound ClC1=CC=CC=C1CC1=NNC(=S)N1C1=CC=CC=C1Cl BWOFOFNNUSUDDC-UHFFFAOYSA-N 0.000 claims 2
- KQRYTFGTIWXPQL-UHFFFAOYSA-N 4-(2-methoxyphenyl)-3-[(2-methylphenyl)methyl]-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=CC=C1N1C(=S)NN=C1CC1=CC=CC=C1C KQRYTFGTIWXPQL-UHFFFAOYSA-N 0.000 claims 2
- MUOPEVOOHPTDEF-UHFFFAOYSA-N 4-(3-chlorophenyl)-3-[(2-chlorophenyl)methyl]-1h-1,2,4-triazole-5-thione Chemical compound ClC1=CC=CC(N2C(NN=C2CC=2C(=CC=CC=2)Cl)=S)=C1 MUOPEVOOHPTDEF-UHFFFAOYSA-N 0.000 claims 2
- BSVQOJXDBTVQCN-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-[(2-chlorophenyl)methyl]-1h-1,2,4-triazole-5-thione Chemical compound C1=CC(Cl)=CC=C1N1C(=S)NN=C1CC1=CC=CC=C1Cl BSVQOJXDBTVQCN-UHFFFAOYSA-N 0.000 claims 2
- DIYYMZBMFGPMFP-UHFFFAOYSA-N 4-[2-chloro-5-(trifluoromethyl)phenyl]-3-[(2,5-dimethoxyphenyl)methyl]-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=C(OC)C(CC=2N(C(=S)NN=2)C=2C(=CC=C(C=2)C(F)(F)F)Cl)=C1 DIYYMZBMFGPMFP-UHFFFAOYSA-N 0.000 claims 2
- ZHJHEODCLCILNC-UHFFFAOYSA-N 4-[3-[(2-bromophenyl)methyl]-5-sulfanylidene-1h-1,2,4-triazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(=S)NN=C1CC1=CC=CC=C1Br ZHJHEODCLCILNC-UHFFFAOYSA-N 0.000 claims 2
- KOGIVIWZHBKZEE-UHFFFAOYSA-N 4-[5-sulfanylidene-3-[(2,4,6-trimethylphenyl)methyl]-1h-1,2,4-triazol-4-yl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1CC1=NNC(=S)N1C1=CC=C(S(N)(=O)=O)C=C1 KOGIVIWZHBKZEE-UHFFFAOYSA-N 0.000 claims 2
- PPLVOPZFVJSNHO-UHFFFAOYSA-N 4-[5-sulfanylidene-3-[(2,4,6-trimethylphenyl)methyl]-1h-1,2,4-triazol-4-yl]benzoic acid Chemical compound CC1=CC(C)=CC(C)=C1CC1=NNC(=S)N1C1=CC=C(C(O)=O)C=C1 PPLVOPZFVJSNHO-UHFFFAOYSA-N 0.000 claims 2
- JLDQLIPWNVYSKM-UHFFFAOYSA-N 4-phenyl-3-[(2,3,4-trimethoxyphenyl)methyl]-1h-1,2,4-triazole-5-thione Chemical compound COC1=C(OC)C(OC)=CC=C1CC1=NNC(=S)N1C1=CC=CC=C1 JLDQLIPWNVYSKM-UHFFFAOYSA-N 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- PYRFHJUXDGQZPM-UHFFFAOYSA-N 1,2,4-triazole-3-thione Chemical compound S=C1N=CN=N1 PYRFHJUXDGQZPM-UHFFFAOYSA-N 0.000 claims 1
- LZTSCEYDCZBRCJ-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazol-3-one Chemical compound OC=1N=CNN=1 LZTSCEYDCZBRCJ-UHFFFAOYSA-N 0.000 claims 1
- TVKIBQHZJWPJAK-UHFFFAOYSA-N 1-[4-[(4-phenyl-5-sulfanylidene-1h-1,2,4-triazol-3-yl)methoxy]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC1=NNC(=S)N1C1=CC=CC=C1 TVKIBQHZJWPJAK-UHFFFAOYSA-N 0.000 claims 1
- BFCRXVMQMULSPW-UHFFFAOYSA-N 2-(3-benzyl-5-sulfanylidene-1h-1,2,4-triazol-4-yl)benzonitrile Chemical compound C=1C=CC=C(C#N)C=1N1C(=S)NN=C1CC1=CC=CC=C1 BFCRXVMQMULSPW-UHFFFAOYSA-N 0.000 claims 1
- UULDCHIXNUFBDR-UHFFFAOYSA-N 2-methyl-4-phenyl-5-pyridin-3-yl-1,2,4-triazole-3-thione Chemical compound C=1C=CC=CC=1N1C(=S)N(C)N=C1C1=CC=CN=C1 UULDCHIXNUFBDR-UHFFFAOYSA-N 0.000 claims 1
- QDUXIUZPZHKWOL-UHFFFAOYSA-N 3-(1h-indol-3-ylmethyl)-4-(2-methoxyphenyl)-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=CC=C1N1C(=S)NN=C1CC1=CNC2=CC=CC=C12 QDUXIUZPZHKWOL-UHFFFAOYSA-N 0.000 claims 1
- FPVPHGICTUFUBK-UHFFFAOYSA-N 3-(1h-indol-3-ylmethyl)-4-(2-methylphenyl)-1h-1,2,4-triazole-5-thione Chemical compound CC1=CC=CC=C1N1C(=S)NN=C1CC1=CNC2=CC=CC=C12 FPVPHGICTUFUBK-UHFFFAOYSA-N 0.000 claims 1
- PECPXTHRQKFSJM-UHFFFAOYSA-N 3-(2-hydroxy-1-phenylethyl)-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound C=1C=CC=CC=1C(CO)C1=NNC(=S)N1C1=CC=CC=C1 PECPXTHRQKFSJM-UHFFFAOYSA-N 0.000 claims 1
- WVXUWVDHZCIUGV-UHFFFAOYSA-N 3-(2-methylpropyl)-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound CC(C)CC1=NNC(=S)N1C1=CC=CC=C1 WVXUWVDHZCIUGV-UHFFFAOYSA-N 0.000 claims 1
- LVCZUHXVUQFASK-UHFFFAOYSA-N 3-(3,4-dihydro-1h-isochromen-1-yl)-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound S=C1NN=C(C2C3=CC=CC=C3CCO2)N1C1=CC=CC=C1 LVCZUHXVUQFASK-UHFFFAOYSA-N 0.000 claims 1
- TZVPCIGUGQABAX-UHFFFAOYSA-N 3-(4-phenyl-5-sulfanylidene-1h-1,2,4-triazol-3-yl)-2,3-dihydroinden-1-one Chemical compound C12=CC=CC=C2C(=O)CC1C1=NNC(=S)N1C1=CC=CC=C1 TZVPCIGUGQABAX-UHFFFAOYSA-N 0.000 claims 1
- ZXRSDKBVHSZDRH-UHFFFAOYSA-N 3-(cyclopentylmethyl)-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound C=1C=CC=CC=1N1C(=S)NN=C1CC1CCCC1 ZXRSDKBVHSZDRH-UHFFFAOYSA-N 0.000 claims 1
- JYJIUYQEWYKGRK-UHFFFAOYSA-N 3-(furan-2-ylmethyl)-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound C=1C=CC=CC=1N1C(=S)NN=C1CC1=CC=CO1 JYJIUYQEWYKGRK-UHFFFAOYSA-N 0.000 claims 1
- XHPJKRPKYODQFN-UHFFFAOYSA-N 3-(oxolan-2-ylmethyl)-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound C=1C=CC=CC=1N1C(=S)NN=C1CC1CCCO1 XHPJKRPKYODQFN-UHFFFAOYSA-N 0.000 claims 1
- ARALFOQPPPSZGA-UHFFFAOYSA-N 3-[(2,5-dimethyl-1,3-thiazol-4-yl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound S1C(C)=NC(CC=2N(C(=S)NN=2)C=2C=CC=CC=2)=C1C ARALFOQPPPSZGA-UHFFFAOYSA-N 0.000 claims 1
- MWGQAMNHTMXRBR-UHFFFAOYSA-N 3-[(2-butoxyphenoxy)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCOC1=CC=CC=C1OCC1=NNC(=S)N1C1=CC=CC=C1 MWGQAMNHTMXRBR-UHFFFAOYSA-N 0.000 claims 1
- XUXKLLUPTARGCC-UHFFFAOYSA-N 3-[(2-chloro-5-methoxyphenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=C(Cl)C(CC=2N(C(=S)NN=2)C=2C=CC=CC=2)=C1 XUXKLLUPTARGCC-UHFFFAOYSA-N 0.000 claims 1
- ZXAMRELGZWFWAU-UHFFFAOYSA-N 3-[(2-chloro-6-fluorophenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound FC1=CC=CC(Cl)=C1CC1=NNC(=S)N1C1=CC=CC=C1 ZXAMRELGZWFWAU-UHFFFAOYSA-N 0.000 claims 1
- YYMOHTMGONXGFB-UHFFFAOYSA-N 3-[(2-chlorophenyl)-hydroxymethyl]-4-(2,2-dimethoxyethyl)-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CC(OC)OC)C(C(O)C=2C(=CC=CC=2)Cl)=N1 YYMOHTMGONXGFB-UHFFFAOYSA-N 0.000 claims 1
- LZECVARMEUVYJI-UHFFFAOYSA-N 3-[(2-chlorophenyl)-hydroxymethyl]-4-(2-methylbutyl)-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CC(C)CC)C(C(O)C=2C(=CC=CC=2)Cl)=N1 LZECVARMEUVYJI-UHFFFAOYSA-N 0.000 claims 1
- XGIGFURMUCHZRO-UHFFFAOYSA-N 3-[(2-chlorophenyl)-hydroxymethyl]-4-(2-methylpropyl)-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CC(C)C)C(C(O)C=2C(=CC=CC=2)Cl)=N1 XGIGFURMUCHZRO-UHFFFAOYSA-N 0.000 claims 1
- OKOLJPYTLVYODL-UHFFFAOYSA-N 3-[(2-chlorophenyl)-hydroxymethyl]-4-(3-methoxypropyl)-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CCCOC)C(C(O)C=2C(=CC=CC=2)Cl)=N1 OKOLJPYTLVYODL-UHFFFAOYSA-N 0.000 claims 1
- SYXPELCYNMSPJK-UHFFFAOYSA-N 3-[(2-chlorophenyl)-hydroxymethyl]-4-(4-nitrophenyl)-1h-1,2,4-triazole-5-thione Chemical compound C=1C=CC=C(Cl)C=1C(O)C1=NNC(=S)N1C1=CC=C([N+]([O-])=O)C=C1 SYXPELCYNMSPJK-UHFFFAOYSA-N 0.000 claims 1
- CEPUMNSIGOZXMX-UHFFFAOYSA-N 3-[(2-chlorophenyl)-hydroxymethyl]-4-cyclohexyl-1h-1,2,4-triazole-5-thione Chemical compound C=1C=CC=C(Cl)C=1C(O)C1=NNC(=S)N1C1CCCCC1 CEPUMNSIGOZXMX-UHFFFAOYSA-N 0.000 claims 1
- MAZCWWLDDYYJJE-UHFFFAOYSA-N 3-[(2-chlorophenyl)-hydroxymethyl]-4-cyclooctyl-1h-1,2,4-triazole-5-thione Chemical compound C=1C=CC=C(Cl)C=1C(O)C1=NNC(=S)N1C1CCCCCCC1 MAZCWWLDDYYJJE-UHFFFAOYSA-N 0.000 claims 1
- RYIHOXBGVNYERD-UHFFFAOYSA-N 3-[(2-chlorophenyl)-hydroxymethyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound C=1C=CC=C(Cl)C=1C(O)C1=NNC(=S)N1C1=CC=CC=C1 RYIHOXBGVNYERD-UHFFFAOYSA-N 0.000 claims 1
- CMVGOTPLFMJSSA-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-(2-piperidin-1-ylethyl)-1h-1,2,4-triazole-5-thione Chemical compound ClC1=CC=CC=C1CC1=NNC(=S)N1CCN1CCCCC1 CMVGOTPLFMJSSA-UHFFFAOYSA-N 0.000 claims 1
- RNQFSLCGIUBDGO-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-(3-morpholin-4-ylpropyl)-1h-1,2,4-triazole-5-thione Chemical compound ClC1=CC=CC=C1CC1=NNC(=S)N1CCCN1CCOCC1 RNQFSLCGIUBDGO-UHFFFAOYSA-N 0.000 claims 1
- LZJRLOVTYOMCAG-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-(oxolan-2-ylmethyl)-1h-1,2,4-triazole-5-thione Chemical compound ClC1=CC=CC=C1CC1=NNC(=S)N1CC1OCCC1 LZJRLOVTYOMCAG-UHFFFAOYSA-N 0.000 claims 1
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| US20090053176A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Combination 937 |
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| CA2740366A1 (en) * | 2008-10-21 | 2010-04-29 | Metabolex, Inc. | Aryl gpr120 receptor agonists and uses thereof |
| CN101723909B (zh) * | 2008-10-29 | 2011-12-28 | 天津药物研究院 | 三唑酮类化合物、其制备方法和用途 |
| WO2011133581A1 (en) | 2010-04-19 | 2011-10-27 | General Atomics | Methods and compositions for assaying enzymatic activity of myeloperoxidase in blood samples |
| 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 |
| 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 |
| BR112014011254A2 (pt) * | 2011-11-11 | 2017-05-16 | Pfizer | 2-tiopirimidinonas |
| CA2854188A1 (en) | 2011-11-14 | 2013-05-23 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with braf inhibitors |
| FR2988000A1 (fr) * | 2012-03-16 | 2013-09-20 | Thomas Wandji | Composition pharmaceutique active dans la therapie des affections virales humaines et animales |
| CN111372579B (zh) * | 2017-10-30 | 2023-08-22 | 神经孔疗法股份有限公司 | 取代的苯基磺酰基苯基三唑硫酮和其用途 |
| KR20200083843A (ko) | 2018-12-31 | 2020-07-09 | 공주대학교 산학협력단 | 4-(2-플루오로페닐)-3-(3-메톡시벤질)-1h-1,2,4-트리아졸-5(4h)-온 및 이의 퇴행성 뇌질환 및 대사성 질환 치료제로서의 용도 |
| CN110313401A (zh) * | 2019-07-12 | 2019-10-11 | 华南农业大学 | 一种促进企剑白墨墨兰组织培养过程中芽分化的方法 |
| WO2021226161A1 (en) * | 2020-05-06 | 2021-11-11 | Biohaven Therapeutics Ltd. | Process for the preparation of verdiperstat |
| PL444904A1 (pl) * | 2023-05-15 | 2024-11-18 | Uniwersytet Medyczny Im. Piastów Śląskich We Wrocławiu | Nowe pochodne 4,6-dimetylo-2-sulfanylopirydyny sprzężone z pierścieniem 1,2,4-triazolu, sposób syntezy pochodnych oraz zastosowanie pochodnych |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI93954C (fi) * | 1988-11-29 | 1995-06-26 | Warner Lambert Co | Menetelmä lääkeaineina käyttökelpoisten 3,5-di-tert-butyyli-4-hydroksifenyylisubstituoitujen 1,2,4- ja 1,3,4-tiadiatsolien sekä oksadiatsolien ja triatsolien valmistamiseksi |
| US5100906A (en) * | 1990-04-19 | 1992-03-31 | Merrell Dow Pharmaceuticals Inc. | 5-aryl-4-alkyl-3h-1,2,4-triazole-3-thiones useful as memory enhancers |
| US5498720A (en) * | 1993-08-26 | 1996-03-12 | Lee; An-Rong | Certain triazole compounds and their pharmaceutical uses |
| US5489598A (en) * | 1994-06-08 | 1996-02-06 | Warner-Lambert Company | Cytoprotection utilizing aryltriazol-3-thiones |
| JPH10147568A (ja) * | 1996-11-19 | 1998-06-02 | Mitsui Chem Inc | ナフタレン誘導体およびそれを有効成分として含有する医薬品 |
| JPH10175970A (ja) * | 1996-12-19 | 1998-06-30 | Mitsui Chem Inc | ベンゾチオフェン誘導体およびそれを有効成分として含有する医薬品 |
| WO2001053331A2 (en) * | 2000-01-24 | 2001-07-26 | Adherex Technologies, Inc. | Peptidomimetic modulators of cell adhesion |
| GB2362101A (en) * | 2000-05-12 | 2001-11-14 | Astrazeneca Ab | Treatment of chronic obstructive pulmonary disease |
| WO2002066447A1 (en) * | 2001-02-21 | 2002-08-29 | Ono Pharmaceutical Co., Ltd. | 4h-1,2,4-triazole-3(2h)-thione deratives as sphingomyelinase inhibitors |
| US6727241B2 (en) * | 2002-06-12 | 2004-04-27 | Chemocentryx | Anti-inflammatory compositions and methods of use |
| WO2004089415A2 (en) * | 2003-04-11 | 2004-10-21 | Novo Nordisk A/S | COMBINATIONS OF AN 11β-HYDROXYSTEROID DEHYDROGENASE TYPE 1 INHIBITOR AND A GLUCOCORTICOID RECEPTOR AGONIST |
-
2003
- 2003-04-25 SE SE0301232A patent/SE0301232D0/xx unknown
-
2004
- 2004-04-22 AU AU2004234320A patent/AU2004234320A1/en not_active Abandoned
- 2004-04-22 MX MXPA05011207A patent/MXPA05011207A/es unknown
- 2004-04-22 CN CNA2004800111102A patent/CN1780822A/zh active Pending
- 2004-04-22 CA CA002523020A patent/CA2523020A1/en not_active Abandoned
- 2004-04-22 JP JP2006508031A patent/JP2006524686A/ja active Pending
- 2004-04-22 KR KR1020057020226A patent/KR20060006064A/ko not_active Withdrawn
- 2004-04-22 EP EP04729000A patent/EP1620410A1/en not_active Withdrawn
- 2004-04-22 BR BRPI0409498-0A patent/BRPI0409498A/pt not_active IP Right Cessation
- 2004-04-22 US US10/554,659 patent/US20070093483A1/en not_active Abandoned
- 2004-04-22 WO PCT/SE2004/000618 patent/WO2004096781A1/en not_active Ceased
-
2005
- 2005-10-24 ZA ZA200508623A patent/ZA200508623B/en unknown
- 2005-11-24 NO NO20055565A patent/NO20055565L/no not_active Application Discontinuation
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