KR20060006064A - 효소 미엘로퍼옥시다제(mpo)의 저해제로서2,4-디하이드로-[1,2,4]트리아졸-3-티온 유도체의 용도 - Google Patents
효소 미엘로퍼옥시다제(mpo)의 저해제로서2,4-디하이드로-[1,2,4]트리아졸-3-티온 유도체의 용도 Download PDFInfo
- Publication number
- KR20060006064A KR20060006064A KR1020057020226A KR20057020226A KR20060006064A KR 20060006064 A KR20060006064 A KR 20060006064A KR 1020057020226 A KR1020057020226 A KR 1020057020226A KR 20057020226 A KR20057020226 A KR 20057020226A KR 20060006064 A KR20060006064 A KR 20060006064A
- Authority
- KR
- South Korea
- Prior art keywords
- dihydro
- triazole
- thione
- 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.)
- Withdrawn
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- 102000003896 Myeloperoxidases Human genes 0.000 title abstract description 33
- 108090000235 Myeloperoxidases Proteins 0.000 title abstract description 33
- 239000003112 inhibitor Substances 0.000 title abstract description 6
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical class SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 233
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
- 201000010099 disease Diseases 0.000 claims abstract description 15
- 230000002265 prevention Effects 0.000 claims abstract description 9
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 8
- 230000009286 beneficial effect Effects 0.000 claims abstract description 7
- 230000005764 inhibitory process Effects 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 56
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 24
- -1 NR 8 R 9 Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 229910052760 oxygen Chemical group 0.000 claims description 19
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- 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 description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 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 description 8
- 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 description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- GZODEUOARIIRIG-UHFFFAOYSA-N 3-[(3-butoxyphenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCOC1=CC=CC(CC=2N(C(=S)NN=2)C=2C=CC=CC=2)=C1 GZODEUOARIIRIG-UHFFFAOYSA-N 0.000 claims description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- AIFHYGAIPROJHU-UHFFFAOYSA-N n-methyl-3-[(4-phenyl-5-sulfanylidene-1h-1,2,4-triazol-3-yl)methyl]benzamide Chemical compound CNC(=O)C1=CC=CC(CC=2N(C(=S)NN=2)C=2C=CC=CC=2)=C1 AIFHYGAIPROJHU-UHFFFAOYSA-N 0.000 claims description 7
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- PTGCVRCZBFUXJJ-UHFFFAOYSA-N 3-[(3,5-dimethylphenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=CC(C)=CC(CC=2N(C(=S)NN=2)C=2C=CC=CC=2)=C1 PTGCVRCZBFUXJJ-UHFFFAOYSA-N 0.000 claims description 6
- PGDUNEOUCOKJAL-UHFFFAOYSA-N 3-[(3-chlorophenyl)methyl]-4-(2-methoxyphenyl)-1h-1,2,4-triazole-5-thione Chemical compound COC1=CC=CC=C1N1C(=S)NN=C1CC1=CC=CC(Cl)=C1 PGDUNEOUCOKJAL-UHFFFAOYSA-N 0.000 claims description 6
- QVCQUURNLKSLDL-UHFFFAOYSA-N 3-[(3-chlorophenyl)methyl]-4-(2-methylphenyl)-1h-1,2,4-triazole-5-thione Chemical compound CC1=CC=CC=C1N1C(=S)NN=C1CC1=CC=CC(Cl)=C1 QVCQUURNLKSLDL-UHFFFAOYSA-N 0.000 claims description 6
- YHWNRQSWAVIQNU-UHFFFAOYSA-N 3-[(3-methoxyphenyl)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)=C1 YHWNRQSWAVIQNU-UHFFFAOYSA-N 0.000 claims description 6
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- QYQDJHHVPACBNV-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-4-(4-methylphenyl)-1h-1,2,4-triazole-5-thione Chemical compound C1=CC(C)=CC=C1N1C(=S)NN=C1CC1=CC=C(Cl)C=C1 QYQDJHHVPACBNV-UHFFFAOYSA-N 0.000 claims description 6
- WVVBLYUXAYHNRM-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound C1=CC(Cl)=CC=C1CC1=NNC(=S)N1C1=CC=CC=C1 WVVBLYUXAYHNRM-UHFFFAOYSA-N 0.000 claims description 6
- MYBBWSOOXWBPHV-UHFFFAOYSA-N 3-[(4-hydroxyphenyl)methyl]-4-(2,4,6-trichlorophenyl)-1h-1,2,4-triazole-5-thione Chemical compound C1=CC(O)=CC=C1CC1=NNC(=S)N1C1=C(Cl)C=C(Cl)C=C1Cl MYBBWSOOXWBPHV-UHFFFAOYSA-N 0.000 claims description 6
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- SJWXTTHJTAWUFY-UHFFFAOYSA-N 3-[(4-hydroxyphenyl)methyl]-4-(4-iodophenyl)-1h-1,2,4-triazole-5-thione Chemical compound C1=CC(O)=CC=C1CC1=NNC(=S)N1C1=CC=C(I)C=C1 SJWXTTHJTAWUFY-UHFFFAOYSA-N 0.000 claims description 6
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- JJCBLKIDNIUEEQ-UHFFFAOYSA-N 4-(2,6-dibromo-4-methylphenyl)-3-[(4-hydroxyphenyl)methyl]-1h-1,2,4-triazole-5-thione Chemical compound BrC1=CC(C)=CC(Br)=C1N1C(=S)NN=C1CC1=CC=C(O)C=C1 JJCBLKIDNIUEEQ-UHFFFAOYSA-N 0.000 claims description 6
- QEFJESBYPQLVCP-UHFFFAOYSA-N 4-phenyl-3-[(2-phenylphenyl)methyl]-1h-1,2,4-triazole-5-thione Chemical compound C=1C=CC=CC=1N1C(=S)NN=C1CC1=CC=CC=C1C1=CC=CC=C1 QEFJESBYPQLVCP-UHFFFAOYSA-N 0.000 claims description 6
- AYAYMNNHDDTQDQ-UHFFFAOYSA-N 4-phenyl-3-[[3-(trifluoromethyl)phenyl]methyl]-1h-1,2,4-triazole-5-thione Chemical compound FC(F)(F)C1=CC=CC(CC=2N(C(=S)NN=2)C=2C=CC=CC=2)=C1 AYAYMNNHDDTQDQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 150000003583 thiosemicarbazides Chemical class 0.000 claims description 6
- 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 description 5
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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| US20090053176A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Combination 937 |
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| 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 |
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| 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 |
| 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 |
| JP2014532712A (ja) | 2011-11-02 | 2014-12-08 | シンタ ファーマシューティカルズ コーポレーション | トポイソメラーゼi阻害剤とhsp90阻害剤の組合せを使用する癌療法 |
| WO2013068875A1 (en) * | 2011-11-11 | 2013-05-16 | Pfizer Inc. | 2-thiopyrimidinones |
| AU2012339679A1 (en) | 2011-11-14 | 2014-06-12 | 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 |
| SG11202003879RA (en) | 2017-10-30 | 2020-05-28 | Neuropore Therapies Inc | Substituted phenyl sulfonyl phenyl triazole thiones and uses thereof |
| 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 |
| MX2022013788A (es) * | 2020-05-06 | 2022-11-30 | Biohaven Therapeutics Ltd | Proceso para la preparacion de 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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| ZA200508623B (en) | 2007-07-25 |
| JP2006524686A (ja) | 2006-11-02 |
| SE0301232D0 (sv) | 2003-04-25 |
| US20070093483A1 (en) | 2007-04-26 |
| WO2004096781A1 (en) | 2004-11-11 |
| BRPI0409498A (pt) | 2006-05-02 |
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