KR20140006070A - Ｈｓｐ90 활성을 조절하는 트리아졸 화합물 - Google Patents
Ｈｓｐ90 활성을 조절하는 트리아졸 화합물 Download PDFInfo
- Publication number
- KR20140006070A KR20140006070A KR1020137030848A KR20137030848A KR20140006070A KR 20140006070 A KR20140006070 A KR 20140006070A KR 1020137030848 A KR1020137030848 A KR 1020137030848A KR 20137030848 A KR20137030848 A KR 20137030848A KR 20140006070 A KR20140006070 A KR 20140006070A
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- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- triazole
- mercapto
- phenyl
- 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.)
- Ceased
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- -1 Triazole compounds Chemical class 0.000 title claims abstract description 231
- 230000000694 effects Effects 0.000 title abstract description 42
- 101100016370 Danio rerio hsp90a.1 gene Proteins 0.000 title 1
- 101100285708 Dictyostelium discoideum hspD gene Proteins 0.000 title 1
- 101100071627 Schizosaccharomyces pombe (strain 972 / ATCC 24843) swo1 gene Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 398
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 136
- 201000011510 cancer Diseases 0.000 claims abstract description 82
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 79
- 201000010099 disease Diseases 0.000 claims abstract description 66
- 230000002062 proliferating effect Effects 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 64
- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 claims abstract description 58
- 101001016865 Homo sapiens Heat shock protein HSP 90-alpha Proteins 0.000 claims abstract description 58
- 125000001072 heteroaryl group Chemical group 0.000 claims description 146
- 125000000217 alkyl group Chemical group 0.000 claims description 121
- 125000003118 aryl group Chemical group 0.000 claims description 94
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 85
- 125000000623 heterocyclic group Chemical group 0.000 claims description 81
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 76
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 76
- 125000000304 alkynyl group Chemical group 0.000 claims description 70
- 125000003342 alkenyl group Chemical group 0.000 claims description 67
- 229910052757 nitrogen Inorganic materials 0.000 claims description 65
- 229940002612 prodrug Drugs 0.000 claims description 64
- 239000000651 prodrug Substances 0.000 claims description 64
- 150000003839 salts Chemical class 0.000 claims description 64
- 125000001188 haloalkyl group Chemical group 0.000 claims description 57
- 239000012453 solvate Substances 0.000 claims description 55
- 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 claims description 54
- 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 claims description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 43
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 239000008194 pharmaceutical composition Substances 0.000 claims description 36
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 241000124008 Mammalia Species 0.000 claims description 21
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 21
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 18
- 230000015556 catabolic process Effects 0.000 claims description 17
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 16
- 238000006731 degradation reaction Methods 0.000 claims description 16
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 9
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 9
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 4
- ZAVMYGRJGRTKNS-UHFFFAOYSA-N 4-(1,2-dimethylindol-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C=C(C)N(C)C3=CC=2)=C1O ZAVMYGRJGRTKNS-UHFFFAOYSA-N 0.000 claims description 4
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- OYPDVIQVLMGVEJ-UHFFFAOYSA-N 2-[5-(2,4-dimethylphenyl)-4-sulfanyltriazol-1-yl]phenol Chemical compound CC1=CC(C)=CC=C1C1=C(S)N=NN1C1=CC=CC=C1O OYPDVIQVLMGVEJ-UHFFFAOYSA-N 0.000 claims description 3
- XAJQRAUKUQZHLM-UHFFFAOYSA-N 4-[5-(2,5-dimethoxyphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound COC1=CC=C(OC)C(C=2N(N=NC=2S)C=2C(=CC(O)=CC=2)O)=C1 XAJQRAUKUQZHLM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005888 tetrahydroindolyl group Chemical group 0.000 claims description 3
- PCKARBFVTAHKLL-UHFFFAOYSA-N 1-[5-[3-(5-ethyl-2,4-dihydroxyphenyl)-5-sulfanylidene-1H-1,2,4-triazol-4-yl]-2,3-dimethylindol-1-yl]ethanone Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C(C)=C(C)N(C(C)=O)C3=CC=2)=C1O PCKARBFVTAHKLL-UHFFFAOYSA-N 0.000 claims description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 2
- MXKIFFBZWXCSSS-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1,3-dimethylindol-5-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)C=2C=C3C(C)=CN(C)C3=CC=2)=C1O MXKIFFBZWXCSSS-UHFFFAOYSA-N 0.000 claims description 2
- UBYWHLVHDACFMM-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1,3-dimethylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C=2C=C3C(C)=CN(C)C3=CC=2)=C1O UBYWHLVHDACFMM-UHFFFAOYSA-N 0.000 claims description 2
- LIRCZXORVKKVOJ-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-ethylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C=1C=C2N(CC)C=CC2=CC=1N1C(S)=NN=C1C1=CC(C(C)C)=C(O)C=C1O LIRCZXORVKKVOJ-UHFFFAOYSA-N 0.000 claims description 2
- LYZLSQLEAHGMQA-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindazol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C=2C=C3C=NN(C)C3=CC=2)=C1O LYZLSQLEAHGMQA-UHFFFAOYSA-N 0.000 claims description 2
- AHXQIXWOSLLMNU-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindazol-6-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C=2C=C3N(C)N=CC3=CC=2)=C1O AHXQIXWOSLLMNU-UHFFFAOYSA-N 0.000 claims description 2
- AWBAVFLOUGHJRJ-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-propan-2-ylindol-4-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)C=2C=3C=CN(C=3C=CC=2)C(C)C)=C1O AWBAVFLOUGHJRJ-UHFFFAOYSA-N 0.000 claims description 2
- STVGXJKUWLHOGD-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-propylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C=1C=C2N(CCC)C=CC2=CC=1N1C(S)=NN=C1C1=CC(C(C)C)=C(O)C=C1O STVGXJKUWLHOGD-UHFFFAOYSA-N 0.000 claims description 2
- BTGVBRHYZUAKCR-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1H-indol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C=2C=C3C=CNC3=CC=2)=C1O BTGVBRHYZUAKCR-UHFFFAOYSA-N 0.000 claims description 2
- NDPQZXRORWTRAB-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(7-methoxy-1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=2C=CN(C(C)C)C=2C(OC)=CC=C1N1C(S)=NN=C1C1=CC(C(C)C)=C(O)C=C1O NDPQZXRORWTRAB-UHFFFAOYSA-N 0.000 claims description 2
- JJGWYOSOCCDKJU-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[1-methyl-2-(trifluoromethyl)benzimidazol-5-yl]-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C=2C=C3N=C(N(C)C3=CC=2)C(F)(F)F)=C1O JJGWYOSOCCDKJU-UHFFFAOYSA-N 0.000 claims description 2
- UIVTZISQSMHJKS-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-(1-ethylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CC)C=CC2=C1N1C(S)=NN=C1C1=CC=C(O)C=C1O UIVTZISQSMHJKS-UHFFFAOYSA-N 0.000 claims description 2
- RKFOLXISFIXXRI-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-(1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(C(C)C)C=CC2=C1N1C(S)=NN=C1C1=CC=C(O)C=C1O RKFOLXISFIXXRI-UHFFFAOYSA-N 0.000 claims description 2
- UBBWIIUNTKWYMN-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-(1H-indol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound OC1=CC(O)=CC=C1C1=NN=C(S)N1C1=CC=CC2=C1C=CN2 UBBWIIUNTKWYMN-UHFFFAOYSA-N 0.000 claims description 2
- LQKKAHUTPJMJET-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-[2-(1-methoxyethyl)-1H-indol-4-yl]-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2NC(C(C)OC)=CC2=C1N1C(S)=NN=C1C1=CC=C(O)C=C1O LQKKAHUTPJMJET-UHFFFAOYSA-N 0.000 claims description 2
- CXYAPZNVLMXJNT-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-(1-methylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C=1C=C2N(C)C=CC2=CC=1N1C(S)=NN=C1C(C(=CC=1O)O)=CC=1C1CC1 CXYAPZNVLMXJNT-UHFFFAOYSA-N 0.000 claims description 2
- REUUXTDHNKRGOI-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-(7-methoxy-1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=2C=CN(C(C)C)C=2C(OC)=CC=C1N1C(S)=NN=C1C(C(=CC=1O)O)=CC=1C1CC1 REUUXTDHNKRGOI-UHFFFAOYSA-N 0.000 claims description 2
- UATPOJPGMXSVGQ-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-(7-methoxy-1-propylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC(OC)=C2N(CCC)C=CC2=C1N1C(S)=NN=C1C(C(=CC=1O)O)=CC=1C1CC1 UATPOJPGMXSVGQ-UHFFFAOYSA-N 0.000 claims description 2
- VDODPAGJCVTEJQ-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-[1-(1-methylcyclopropyl)indol-4-yl]-1H-1,2,4-triazole-5-thione Chemical compound C1=CC2=C(N3C(=NN=C3S)C=3C(=CC(O)=C(C4CC4)C=3)O)C=CC=C2N1C1(C)CC1 VDODPAGJCVTEJQ-UHFFFAOYSA-N 0.000 claims description 2
- STLUOXMEJVFZCP-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1,2,3-trimethylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C(C)=C(C)N(C)C3=CC=2)=C1O STLUOXMEJVFZCP-UHFFFAOYSA-N 0.000 claims description 2
- FODKQXTYMMCSPC-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-ethyl-2-methylbenzimidazol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3N=C(C)N(CC)C3=CC=2)=C1O FODKQXTYMMCSPC-UHFFFAOYSA-N 0.000 claims description 2
- YUZVSLHCEHKSQJ-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-hexylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CCCCCC)C=CC2=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O YUZVSLHCEHKSQJ-UHFFFAOYSA-N 0.000 claims description 2
- INSPZFPAIAETMI-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-methylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O INSPZFPAIAETMI-UHFFFAOYSA-N 0.000 claims description 2
- OLLRLHGHUWXAFP-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-pentylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CCCCC)C=CC2=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O OLLRLHGHUWXAFP-UHFFFAOYSA-N 0.000 claims description 2
- QZCQHJMGZJLICK-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=3C=CN(C=3C=CC=2)C(C)C)=C1O QZCQHJMGZJLICK-UHFFFAOYSA-N 0.000 claims description 2
- LBVJBJFVUWQRLE-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-propylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CCC)C=CC2=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O LBVJBJFVUWQRLE-UHFFFAOYSA-N 0.000 claims description 2
- QSFLGQYOSRZJAQ-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(3-ethyl-1-methylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2C(CC)=CN(C)C2=CC=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O QSFLGQYOSRZJAQ-UHFFFAOYSA-N 0.000 claims description 2
- NZZXFHSCKWJAQF-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(3-ethyl-2-methylbenzimidazol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3N(CC)C(C)=NC3=CC=2)=C1O NZZXFHSCKWJAQF-UHFFFAOYSA-N 0.000 claims description 2
- BXLIPBMFJHQUAZ-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(7-hydroxy-1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=3C=CN(C=3C(O)=CC=2)C(C)C)=C1O BXLIPBMFJHQUAZ-UHFFFAOYSA-N 0.000 claims description 2
- ZBXXGZDCLQEVEQ-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(7-methoxy-1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=3C=CN(C=3C(OC)=CC=2)C(C)C)=C1O ZBXXGZDCLQEVEQ-UHFFFAOYSA-N 0.000 claims description 2
- QYVIZOQFOBGAHW-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(7-methoxy-2-methyl-1-benzofuran-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=3C=C(C)OC=3C(OC)=CC=2)=C1O QYVIZOQFOBGAHW-UHFFFAOYSA-N 0.000 claims description 2
- ARFPAOWQRMCLCC-UHFFFAOYSA-N 4-(1,3-dimethylindol-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(CC)=CC(C=2N(C(O)=NN=2)C=2C=C3C(C)=CN(C)C3=CC=2)=C1O ARFPAOWQRMCLCC-UHFFFAOYSA-N 0.000 claims description 2
- PCYXGRPZGRZCMY-UHFFFAOYSA-N 4-(1,3-dimethylindol-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C(C)=CN(C)C3=CC=2)=C1O PCYXGRPZGRZCMY-UHFFFAOYSA-N 0.000 claims description 2
- CXWAUYMEDCGIRL-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C=COC3=CC=2)=C1O CXWAUYMEDCGIRL-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001475 halogen functional group Chemical group 0.000 claims 26
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- NLHLYUFHTZQGLQ-UHFFFAOYSA-N 4-[5-(2,3-dimethyl-1H-indol-4-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C=12C(C)=C(C)NC2=CC=CC=1C1=C(S)N=NN1C1=CC=C(O)C=C1O NLHLYUFHTZQGLQ-UHFFFAOYSA-N 0.000 claims 1
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- LAYGIGZQEPOADS-UHFFFAOYSA-N 4-[5-(2,3-dimethylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CC1=CC=CC(C=2N(N=NC=2S)C=2C(=CC(O)=CC=2)O)=C1C LAYGIGZQEPOADS-UHFFFAOYSA-N 0.000 claims 1
- SKUHKFMIHMMXBR-UHFFFAOYSA-N 4-[5-(2,4-dimethylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CC1=CC(C)=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O SKUHKFMIHMMXBR-UHFFFAOYSA-N 0.000 claims 1
- JTODPTADEPPHBY-UHFFFAOYSA-N 4-[5-(2,6-diethylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CCC1=CC=CC(CC)=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O JTODPTADEPPHBY-UHFFFAOYSA-N 0.000 claims 1
- UDWQTWCDZDMCQV-UHFFFAOYSA-N 4-[5-(2-chlorophenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1N1C(C=2C(=CC=CC=2)Cl)=C(S)N=N1 UDWQTWCDZDMCQV-UHFFFAOYSA-N 0.000 claims 1
- QXUTWAVVVCEISA-UHFFFAOYSA-N 4-[5-(2-ethylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CCC1=CC=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O QXUTWAVVVCEISA-UHFFFAOYSA-N 0.000 claims 1
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- BEXDOQZVKJBYCF-UHFFFAOYSA-N 4-[5-(2-methylsulfanylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CSC1=CC=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O BEXDOQZVKJBYCF-UHFFFAOYSA-N 0.000 claims 1
- WVGFMPBFGBVGGH-UHFFFAOYSA-N 4-[5-(2-phenylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1N1C(C=2C(=CC=CC=2)C=2C=CC=CC=2)=C(S)N=N1 WVGFMPBFGBVGGH-UHFFFAOYSA-N 0.000 claims 1
- RMMQOLPSKHIUBO-UHFFFAOYSA-N 4-[5-(3,5-dimethoxyphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound COC1=CC(OC)=CC(C=2N(N=NC=2S)C=2C(=CC(O)=CC=2)O)=C1 RMMQOLPSKHIUBO-UHFFFAOYSA-N 0.000 claims 1
- XQKTWAQABRVKTF-UHFFFAOYSA-N 4-[5-(3,5-ditert-butylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C=2N(N=NC=2S)C=2C(=CC(O)=CC=2)O)=C1 XQKTWAQABRVKTF-UHFFFAOYSA-N 0.000 claims 1
- FBBWMYKMWMRPFK-UHFFFAOYSA-N 4-[5-(3-chloro-2-methoxyphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound COC1=C(Cl)C=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O FBBWMYKMWMRPFK-UHFFFAOYSA-N 0.000 claims 1
- MGAZRBVNNFEALV-UHFFFAOYSA-N 4-[5-(3-chlorophenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1N1C(C=2C=C(Cl)C=CC=2)=C(S)N=N1 MGAZRBVNNFEALV-UHFFFAOYSA-N 0.000 claims 1
- IEQNGPBBEOUZJB-UHFFFAOYSA-N 4-[5-(3-fluorophenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1N1C(C=2C=C(F)C=CC=2)=C(S)N=N1 IEQNGPBBEOUZJB-UHFFFAOYSA-N 0.000 claims 1
- IOMQEKVQBSWHCU-UHFFFAOYSA-N 4-[5-(3-methoxyphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound COC1=CC=CC(C=2N(N=NC=2S)C=2C(=CC(O)=CC=2)O)=C1 IOMQEKVQBSWHCU-UHFFFAOYSA-N 0.000 claims 1
- KGYRPCNKAODAAO-UHFFFAOYSA-N 4-[5-(3-methylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CC1=CC=CC(C=2N(N=NC=2S)C=2C(=CC(O)=CC=2)O)=C1 KGYRPCNKAODAAO-UHFFFAOYSA-N 0.000 claims 1
- DNIKXDFMZZPLLP-UHFFFAOYSA-N 4-[5-(3-phenylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1N1C(C=2C=C(C=CC=2)C=2C=CC=CC=2)=C(S)N=N1 DNIKXDFMZZPLLP-UHFFFAOYSA-N 0.000 claims 1
- XWGFZOWEULZHON-UHFFFAOYSA-N 4-[5-(3-tert-butyl-4-methoxyphenyl)-4-sulfanyltriazol-1-yl]-6-ethylbenzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(N2C(=C(S)N=N2)C=2C=C(C(OC)=CC=2)C(C)(C)C)=C1O XWGFZOWEULZHON-UHFFFAOYSA-N 0.000 claims 1
- CFEVGPLCJGLNTR-UHFFFAOYSA-N 4-[5-(4-bromo-2-methylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CC1=CC(Br)=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O CFEVGPLCJGLNTR-UHFFFAOYSA-N 0.000 claims 1
- WBIAOWDZWHOQLR-UHFFFAOYSA-N 4-[5-(4-butyl-2-methylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CC1=CC(CCCC)=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O WBIAOWDZWHOQLR-UHFFFAOYSA-N 0.000 claims 1
- BORCHZNOBITQAC-UHFFFAOYSA-N 4-[5-(4-chloronaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1N1C(C=2C3=CC=CC=C3C(Cl)=CC=2)=C(S)N=N1 BORCHZNOBITQAC-UHFFFAOYSA-N 0.000 claims 1
- DYUCEMVHADUUHX-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=C(S)N=N1 DYUCEMVHADUUHX-UHFFFAOYSA-N 0.000 claims 1
- UATJXGDPDCSCQW-UHFFFAOYSA-N 4-[5-(4-fluoro-2-methylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CC1=CC(F)=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O UATJXGDPDCSCQW-UHFFFAOYSA-N 0.000 claims 1
- MYBVWYRIMYLOCV-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1N1C(C=2C=CC(F)=CC=2)=C(S)N=N1 MYBVWYRIMYLOCV-UHFFFAOYSA-N 0.000 claims 1
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- MJULUTAPKWSYCL-UHFFFAOYSA-N 4-[5-(4-methylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C1=CC(C)=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O MJULUTAPKWSYCL-UHFFFAOYSA-N 0.000 claims 1
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- MSKPLRAWJKDVMF-UHFFFAOYSA-N 4-[5-(4-pentoxyphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C1=CC(OCCCCC)=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O MSKPLRAWJKDVMF-UHFFFAOYSA-N 0.000 claims 1
- HCKOIBRUVHWONE-UHFFFAOYSA-N 4-[5-(4-propan-2-yloxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C12=CC=CC=C2C(OC(C)C)=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O HCKOIBRUVHWONE-UHFFFAOYSA-N 0.000 claims 1
- PQMIPBAOVWAVPP-UHFFFAOYSA-N 4-[5-(4-propoxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C12=CC=CC=C2C(OCCC)=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O PQMIPBAOVWAVPP-UHFFFAOYSA-N 0.000 claims 1
- WSHPTVJCZQTQFG-UHFFFAOYSA-N 4-[5-(5-propan-2-yloxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C1=CC=C2C(OC(C)C)=CC=CC2=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O WSHPTVJCZQTQFG-UHFFFAOYSA-N 0.000 claims 1
- KKQMXQYSXVEDGZ-UHFFFAOYSA-N 4-[5-(5-propoxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C1=CC=C2C(OCCC)=CC=CC2=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O KKQMXQYSXVEDGZ-UHFFFAOYSA-N 0.000 claims 1
- AGIGIYOJBUVMCA-UHFFFAOYSA-N 4-[5-(6-ethoxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,2-diol Chemical compound C=1C=CC2=CC(OCC)=CC=C2C=1C1=C(S)N=NN1C1=CC=C(O)C(O)=C1 AGIGIYOJBUVMCA-UHFFFAOYSA-N 0.000 claims 1
- NMRQPWDQZAQXAX-UHFFFAOYSA-N 4-[5-(6-methoxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,2-diol Chemical compound C=1C=CC2=CC(OC)=CC=C2C=1C1=C(S)N=NN1C1=CC=C(O)C(O)=C1 NMRQPWDQZAQXAX-UHFFFAOYSA-N 0.000 claims 1
- WKJJKBIVZAEMLW-UHFFFAOYSA-N 4-[5-(6-propan-2-yloxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,2-diol Chemical compound C=1C=CC2=CC(OC(C)C)=CC=C2C=1C1=C(S)N=NN1C1=CC=C(O)C(O)=C1 WKJJKBIVZAEMLW-UHFFFAOYSA-N 0.000 claims 1
- ONQHVMVORXLSLJ-UHFFFAOYSA-N 4-[5-(6-propoxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,2-diol Chemical compound C=1C=CC2=CC(OCCC)=CC=C2C=1C1=C(S)N=NN1C1=CC=C(O)C(O)=C1 ONQHVMVORXLSLJ-UHFFFAOYSA-N 0.000 claims 1
- LHDPWURQUIYLBA-UHFFFAOYSA-N 4-[5-(7-ethoxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C12=CC(OCC)=CC=C2C=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O LHDPWURQUIYLBA-UHFFFAOYSA-N 0.000 claims 1
- XGQZFVLUAZHCHS-UHFFFAOYSA-N 4-[5-(7-methoxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C12=CC(OC)=CC=C2C=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O XGQZFVLUAZHCHS-UHFFFAOYSA-N 0.000 claims 1
- AUYJAMQXNYJNLX-UHFFFAOYSA-N 4-[5-(7-propan-2-yloxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C12=CC(OC(C)C)=CC=C2C=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O AUYJAMQXNYJNLX-UHFFFAOYSA-N 0.000 claims 1
- NVRGGYIKLGTMAI-UHFFFAOYSA-N 4-[5-(7-propoxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C12=CC(OCCC)=CC=C2C=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O NVRGGYIKLGTMAI-UHFFFAOYSA-N 0.000 claims 1
- MQDJHKNSGMPXII-UHFFFAOYSA-N 4-[5-(naphthalen-1-ylmethyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1N1C(CC=2C3=CC=CC=C3C=CC=2)=C(S)N=N1 MQDJHKNSGMPXII-UHFFFAOYSA-N 0.000 claims 1
- KGBBGIKBWYHOML-UHFFFAOYSA-N 4-[5-[1-(2-methoxyethoxy)indol-4-yl]-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C1=CC=C2N(OCCOC)C=CC2=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O KGBBGIKBWYHOML-UHFFFAOYSA-N 0.000 claims 1
- PWPJYZRIWWTTQQ-UHFFFAOYSA-N 4-[5-[2,6-di(propan-2-yl)phenyl]-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O PWPJYZRIWWTTQQ-UHFFFAOYSA-N 0.000 claims 1
- XRCMYUBITUDKBQ-UHFFFAOYSA-N 4-[5-[4-(2-methoxyethoxy)naphthalen-1-yl]-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C12=CC=CC=C2C(OCCOC)=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O XRCMYUBITUDKBQ-UHFFFAOYSA-N 0.000 claims 1
- ZSZIANUMRDXGDW-UHFFFAOYSA-N 4-[5-[5-(hydroxymethyl)-2-methylphenyl]-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CC1=CC=C(CO)C=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O ZSZIANUMRDXGDW-UHFFFAOYSA-N 0.000 claims 1
- YWKQOFDNFNMVMV-UHFFFAOYSA-N 4-[5-[7-(2-methoxyethoxy)naphthalen-1-yl]-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C12=CC(OCCOC)=CC=C2C=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O YWKQOFDNFNMVMV-UHFFFAOYSA-N 0.000 claims 1
- IZQAGJHUNRYXAO-UHFFFAOYSA-N 4-cyclopropyl-6-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)benzene-1,3-diol Chemical compound OC1=CC(O)=C(N2C(=C(S)N=N2)C=2C3=CC=CC=C3C=CC=2)C=C1C1CC1 IZQAGJHUNRYXAO-UHFFFAOYSA-N 0.000 claims 1
- SIBYHFAABFDSGD-UHFFFAOYSA-N 4-ethyl-2-methyl-6-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)benzene-1,3-diol Chemical compound CC1=C(O)C(CC)=CC(N2C(=C(S)N=N2)C=2C3=CC=CC=C3C=CC=2)=C1O SIBYHFAABFDSGD-UHFFFAOYSA-N 0.000 claims 1
- BRBCWSPPBKTMFO-UHFFFAOYSA-N 4-ethyl-6-(4-hydroxy-5-naphthalen-1-yltriazol-1-yl)benzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(N2C(=C(O)N=N2)C=2C3=CC=CC=C3C=CC=2)=C1O BRBCWSPPBKTMFO-UHFFFAOYSA-N 0.000 claims 1
- TZPQLCILIDGDDW-UHFFFAOYSA-N 4-ethyl-6-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)benzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(N2C(=C(S)N=N2)C=2C3=CC=CC=C3C=CC=2)=C1O TZPQLCILIDGDDW-UHFFFAOYSA-N 0.000 claims 1
- FZKGQQUXHADZST-UHFFFAOYSA-N 4-ethyl-6-[4-hydroxy-5-(1-propan-2-ylindol-3-yl)triazol-1-yl]benzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(N2C(=C(O)N=N2)C=2C3=CC=CC=C3N(C(C)C)C=2)=C1O FZKGQQUXHADZST-UHFFFAOYSA-N 0.000 claims 1
- QEOMKWZMDMJVIC-UHFFFAOYSA-N 4-ethyl-6-[4-sulfanyl-5-(1,2,3-trimethylindol-5-yl)triazol-1-yl]benzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(N2C(=C(S)N=N2)C=2C=C3C(C)=C(C)N(C)C3=CC=2)=C1O QEOMKWZMDMJVIC-UHFFFAOYSA-N 0.000 claims 1
- CVTVSTQFCASZBT-UHFFFAOYSA-N 4-ethyl-6-[5-(1-propan-2-ylindol-4-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(N2C(=C(S)N=N2)C=2C=3C=CN(C=3C=CC=2)C(C)C)=C1O CVTVSTQFCASZBT-UHFFFAOYSA-N 0.000 claims 1
- ARONUOGNRIHKER-UHFFFAOYSA-N 4-ethyl-6-[5-(4-methoxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(N2C(=C(S)N=N2)C=2C3=CC=CC=C3C(OC)=CC=2)=C1O ARONUOGNRIHKER-UHFFFAOYSA-N 0.000 claims 1
- XKZSAJXABDPACT-UHFFFAOYSA-N 4-ethyl-6-[5-(5-hydroxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(N2C(=C(S)N=N2)C=2C3=CC=CC(O)=C3C=CC=2)=C1O XKZSAJXABDPACT-UHFFFAOYSA-N 0.000 claims 1
- QZFJEEUJORPXSK-UHFFFAOYSA-N 4-ethyl-6-[5-(5-methoxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(N2C(=C(S)N=N2)C=2C3=CC=CC(OC)=C3C=CC=2)=C1O QZFJEEUJORPXSK-UHFFFAOYSA-N 0.000 claims 1
- WKBUWEDWYXRUBC-UHFFFAOYSA-N 4-ethyl-6-[5-(6-methoxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(N2C(=C(S)N=N2)C=2C3=CC=C(OC)C=C3C=CC=2)=C1O WKBUWEDWYXRUBC-UHFFFAOYSA-N 0.000 claims 1
- SYGCUBZSIBCWCY-UHFFFAOYSA-N 4-ethyl-6-[5-(7-methoxy-1-propan-2-ylindol-4-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(N2C(=C(S)N=N2)C=2C=3C=CN(C=3C(OC)=CC=2)C(C)C)=C1O SYGCUBZSIBCWCY-UHFFFAOYSA-N 0.000 claims 1
- MWOXTTWWXHPMFD-UHFFFAOYSA-N 4-hexyl-6-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)benzene-1,3-diol Chemical compound C1=C(O)C(CCCCCC)=CC(N2C(=C(S)N=N2)C=2C3=CC=CC=C3C=CC=2)=C1O MWOXTTWWXHPMFD-UHFFFAOYSA-N 0.000 claims 1
- KDKQKMXAQNXMCH-UHFFFAOYSA-N 4-methoxy-6-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)benzene-1,3-diol Chemical compound C1=C(O)C(OC)=CC(N2C(=C(S)N=N2)C=2C3=CC=CC=C3C=CC=2)=C1O KDKQKMXAQNXMCH-UHFFFAOYSA-N 0.000 claims 1
- OQUKZUYJPMHMOY-UHFFFAOYSA-N 4-methyl-6-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)benzene-1,3-diol Chemical compound C1=C(O)C(C)=CC(N2C(=C(S)N=N2)C=2C3=CC=CC=C3C=CC=2)=C1O OQUKZUYJPMHMOY-UHFFFAOYSA-N 0.000 claims 1
- SQZZKFZAZWVZQA-UHFFFAOYSA-N 4-tert-butyl-6-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)benzene-1,3-diol Chemical compound C1=C(O)C(C(C)(C)C)=CC(N2C(=C(S)N=N2)C=2C3=CC=CC=C3C=CC=2)=C1O SQZZKFZAZWVZQA-UHFFFAOYSA-N 0.000 claims 1
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- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- 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
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- 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
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- 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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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
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| PT1817295E (pt) | 2004-11-18 | 2013-02-18 | Synta Pharmaceuticals Corp | Compostos de triazol que modulam a actividade da hsp90 |
| DE102005007304A1 (de) | 2005-02-17 | 2006-08-24 | Merck Patent Gmbh | Triazolderivate |
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