ZA200508623B - Use of derivatives of 2,4-dihydro-[1,2,4]triazole-3-thione as inhibitors of the enzyme myeloperoxidase (MPO) - Google Patents
Use of derivatives of 2,4-dihydro-[1,2,4]triazole-3-thione as inhibitors of the enzyme myeloperoxidase (MPO) Download PDFInfo
- Publication number
- ZA200508623B ZA200508623B ZA200508623A ZA200508623A ZA200508623B ZA 200508623 B ZA200508623 B ZA 200508623B ZA 200508623 A ZA200508623 A ZA 200508623A ZA 200508623 A ZA200508623 A ZA 200508623A ZA 200508623 B ZA200508623 B ZA 200508623B
- Authority
- ZA
- South Africa
- Prior art keywords
- thione
- dihydro
- triazole
- phenyl
- chlorobenzyl
- Prior art date
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- 102000003896 Myeloperoxidases Human genes 0.000 title description 24
- 108090000235 Myeloperoxidases Proteins 0.000 title description 24
- 239000003112 inhibitor Substances 0.000 title description 5
- 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 3
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 19
- 241001061127 Thione Species 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- -1 NRER® Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
- 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 5
- 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 5
- 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 5
- 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 5
- 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 5
- 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 5
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 5
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- UIWJPXQEUUJZFB-UHFFFAOYSA-N 3-[(4-hydroxyphenyl)methyl]-4-(4-piperidin-1-ylsulfonylphenyl)-1h-1,2,4-triazole-5-thione Chemical compound C1=CC(O)=CC=C1CC1=NNC(=S)N1C1=CC=C(S(=O)(=O)N2CCCCC2)C=C1 UIWJPXQEUUJZFB-UHFFFAOYSA-N 0.000 claims description 4
- JGSIAOZAXBWRFO-UHFFFAOYSA-N 3-methylsulfanyl-1-phenyl-4,5-dihydrobenzo[g]indazole Chemical compound C1CC2=CC=CC=C2C2=C1C(SC)=NN2C1=CC=CC=C1 JGSIAOZAXBWRFO-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 4
- 239000002671 adjuvant Substances 0.000 claims description 4
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- 239000003085 diluting agent Substances 0.000 claims description 4
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 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 3
- 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 description 3
- 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 description 3
- 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 3
- 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 3
- 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 3
- 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 3
- WGNZVXDWZCELOY-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-4-pyridin-3-yl-1h-1,2,4-triazole-5-thione Chemical compound ClC1=CC=CC=C1CC1=NNC(=S)N1C1=CC=CN=C1 WGNZVXDWZCELOY-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- DOKKSJAWUZPXJW-UHFFFAOYSA-N 3-[(3-butoxyphenoxy)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCOC1=CC=CC(OCC=2N(C(=S)NN=2)C=2C=CC=CC=2)=C1 DOKKSJAWUZPXJW-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- XQZAUEBTIPOWJP-UHFFFAOYSA-N 3-[(3-methylphenyl)methyl]-4-phenyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=CC=CC(CC=2N(C(=S)NN=2)C=2C=CC=CC=2)=C1 XQZAUEBTIPOWJP-UHFFFAOYSA-N 0.000 claims description 3
- PKYTZOABMZKOPC-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]-4-[3,5-bis(trifluoromethyl)phenyl]-1h-1,2,4-triazole-5-thione Chemical compound C1=CC(N)=CC=C1CC1=NNC(=S)N1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 PKYTZOABMZKOPC-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- JSIWGCJLWKNQCW-UHFFFAOYSA-N 4-hexyl-3-[(4-methoxyanilino)methyl]-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CCCCCC)C(CNC=2C=CC(OC)=CC=2)=N1 JSIWGCJLWKNQCW-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- CMRPESBSFDJNCZ-UHFFFAOYSA-N n-methyl-2-[(4-phenyl-5-sulfanylidene-1h-1,2,4-triazol-3-yl)methoxy]benzamide Chemical compound CNC(=O)C1=CC=CC=C1OCC1=NNC(=S)N1C1=CC=CC=C1 CMRPESBSFDJNCZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 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 2
- 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 description 2
- 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 description 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 description 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 description 2
- 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 description 2
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- 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 2
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- PIVKSKRTISDEIO-UHFFFAOYSA-N 3-[(4-methoxyphenoxy)methyl]-4-(3-methoxypropyl)-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CCCOC)C(COC=2C=CC(OC)=CC=2)=N1 PIVKSKRTISDEIO-UHFFFAOYSA-N 0.000 claims description 2
- YZAFNZQTXMUHAN-UHFFFAOYSA-N 3-[(4-methoxyphenoxy)methyl]-4-(3-morpholin-4-ylpropyl)-1h-1,2,4-triazole-5-thione Chemical compound C1=CC(OC)=CC=C1OCC1=NNC(=S)N1CCCN1CCOCC1 YZAFNZQTXMUHAN-UHFFFAOYSA-N 0.000 claims description 2
- SHBUSYVVXUPRBS-UHFFFAOYSA-N 3-benzyl-4-(2-thiophen-2-ylethyl)-1h-1,2,4-triazole-5-thione Chemical compound C=1C=CSC=1CCN1C(=S)NN=C1CC1=CC=CC=C1 SHBUSYVVXUPRBS-UHFFFAOYSA-N 0.000 claims description 2
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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SE0301232A SE0301232D0 (sv) | 2003-04-25 | 2003-04-25 | Novel use |
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ZA200508623B true ZA200508623B (en) | 2007-07-25 |
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ZA200508623A ZA200508623B (en) | 2003-04-25 | 2005-10-24 | Use of derivatives of 2,4-dihydro-[1,2,4]triazole-3-thione as inhibitors of the enzyme myeloperoxidase (MPO) |
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US (1) | US20070093483A1 (pt) |
EP (1) | EP1620410A1 (pt) |
JP (1) | JP2006524686A (pt) |
KR (1) | KR20060006064A (pt) |
CN (1) | CN1780822A (pt) |
AU (1) | AU2004234320A1 (pt) |
BR (1) | BRPI0409498A (pt) |
CA (1) | CA2523020A1 (pt) |
MX (1) | MXPA05011207A (pt) |
NO (1) | NO20055565L (pt) |
SE (1) | SE0301232D0 (pt) |
WO (1) | WO2004096781A1 (pt) |
ZA (1) | ZA200508623B (pt) |
Families Citing this family (24)
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AR039385A1 (es) | 2002-04-19 | 2005-02-16 | Astrazeneca Ab | Derivados de tioxantina como inhibidores de la mieloperoxidasa |
SE0302756D0 (sv) * | 2003-10-17 | 2003-10-17 | Astrazeneca Ab | Novel Compounds |
SE0402591D0 (sv) * | 2004-10-25 | 2004-10-25 | Astrazeneca Ab | Novel use |
KR101374553B1 (ko) | 2004-11-18 | 2014-03-17 | 신타 파마슈티칼스 코프. | Hsp90 활성을 조절하는 트리아졸 화합물 |
MY140748A (en) | 2004-12-06 | 2010-01-15 | Astrazeneca Ab | Novel pyrrolo [3,2-d] pyrimidin-4-one derivatives and their use in therapy |
TW200804383A (en) | 2006-06-05 | 2008-01-16 | Astrazeneca Ab | New compounds |
PE20110371A1 (es) | 2006-08-15 | 2011-06-24 | Novartis Ag | COMPUESTOS HETEROCICLICOS QUE MODULAN LA ACTIVIDAD DE LA ESTEROIL-CoA-DESATURASA |
EP1921073A1 (en) | 2006-11-10 | 2008-05-14 | Laboratorios del Dr. Esteve S.A. | 1,2,4-Triazole derivatives as sigma receptor inhibitors |
US20090053176A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Combination 937 |
CN101945848A (zh) | 2007-12-20 | 2011-01-12 | 英维沃医药有限公司 | 四取代的苯 |
NZ592603A (en) * | 2008-10-21 | 2013-02-22 | 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 |
EP2773345A1 (en) | 2011-11-02 | 2014-09-10 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of hsp90 inhibitors with topoisomerase i inhibitors |
EP2776025A1 (en) | 2011-11-02 | 2014-09-17 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with platinum-containing agents |
PE20161219A1 (es) * | 2011-11-11 | 2016-11-17 | Pfizer | 2-tiopirimidinonas |
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 |
KR102639231B1 (ko) | 2017-10-30 | 2024-02-22 | 뉴로포레 테라피스, 인코포레이티드 | 치환된 페닐 설폰일 페닐 트리아졸 싸이온 및 이의 용도 |
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 |
JP2023524241A (ja) * | 2020-05-06 | 2023-06-09 | バイオヘイブン・セラピューティクス・リミテッド | ベルジペルスタットの調製のためのプロセス |
US11926602B1 (en) * | 2023-08-23 | 2024-03-12 | King Faisal University | 4-amino-5-(4-fluoro-3-phenoxyphenyl)-4H-1,2,4-triazole-3-thiol derivatives as antifungal agents |
Family Cites Families (11)
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NZ231534A (en) * | 1988-11-29 | 1992-02-25 | Warner Lambert Co | 3,5-di-t-butyl-4-hydroxyphenyl-triazoles, oxadiazoles and thiadiazoles; anti-inflammatory compositions |
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 |
AU2001231154A1 (en) * | 2000-01-24 | 2001-07-31 | 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 |
EP1615667A2 (en) * | 2003-04-11 | 2006-01-18 | Novo Nordisk A/S | Combinations of an 11-beta-hydroxysteroid dehydrogenase type 1 inhibitor and a glucocorticoid receptor agonist |
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2003
- 2003-04-25 SE SE0301232A patent/SE0301232D0/xx unknown
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2004
- 2004-04-22 AU AU2004234320A patent/AU2004234320A1/en not_active Abandoned
- 2004-04-22 MX MXPA05011207A patent/MXPA05011207A/es unknown
- 2004-04-22 JP JP2006508031A patent/JP2006524686A/ja active Pending
- 2004-04-22 CA CA002523020A patent/CA2523020A1/en not_active Abandoned
- 2004-04-22 CN CNA2004800111102A patent/CN1780822A/zh active Pending
- 2004-04-22 WO PCT/SE2004/000618 patent/WO2004096781A1/en active Application Filing
- 2004-04-22 KR KR1020057020226A patent/KR20060006064A/ko not_active Application Discontinuation
- 2004-04-22 BR BRPI0409498-0A patent/BRPI0409498A/pt not_active IP Right Cessation
- 2004-04-22 EP EP04729000A patent/EP1620410A1/en not_active Withdrawn
- 2004-04-22 US US10/554,659 patent/US20070093483A1/en not_active Abandoned
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2005
- 2005-10-24 ZA ZA200508623A patent/ZA200508623B/en unknown
- 2005-11-24 NO NO20055565A patent/NO20055565L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
JP2006524686A (ja) | 2006-11-02 |
SE0301232D0 (sv) | 2003-04-25 |
MXPA05011207A (es) | 2005-12-14 |
CN1780822A (zh) | 2006-05-31 |
CA2523020A1 (en) | 2004-11-11 |
AU2004234320A1 (en) | 2004-11-11 |
BRPI0409498A (pt) | 2006-05-02 |
US20070093483A1 (en) | 2007-04-26 |
KR20060006064A (ko) | 2006-01-18 |
EP1620410A1 (en) | 2006-02-01 |
NO20055565D0 (no) | 2005-11-24 |
WO2004096781A1 (en) | 2004-11-11 |
NO20055565L (no) | 2006-01-25 |
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