TW201041514A - Triazole compounds carrying a sulfur substituent II - Google Patents

Info

Publication number

TW201041514A

TW201041514A TW099113195A TW99113195A TW201041514A TW 201041514 A TW201041514 A TW 201041514A TW 099113195 A TW099113195 A TW 099113195A TW 99113195 A TW99113195 A TW 99113195A TW 201041514 A TW201041514 A TW 201041514A

Authority

TW

Taiwan

Prior art keywords

compound

group

formula

alkyl

hydrogen

Prior art date

2009-04-24

Links

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• -1 Triazole compounds Chemical class 0.000 title claims abstract description 342
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title abstract description 23
• 150000001875 compounds Chemical class 0.000 claims abstract description 752
• 239000000203 mixture Substances 0.000 claims abstract description 113
• 238000000034 method Methods 0.000 claims abstract description 58
• 125000000217 alkyl group Chemical group 0.000 claims description 146
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 126
• 229910052739 hydrogen Inorganic materials 0.000 claims description 124
• 239000001257 hydrogen Substances 0.000 claims description 123
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 69
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 66
• 125000003545 alkoxy group Chemical group 0.000 claims description 60
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
• 239000000460 chlorine Substances 0.000 claims description 36
• 239000000463 material Substances 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 36
• 241000233866 Fungi Species 0.000 claims description 35
• 125000001424 substituent group Chemical group 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
• 150000002431 hydrogen Chemical class 0.000 claims description 26
• 125000001188 haloalkyl group Chemical group 0.000 claims description 25
• 239000007789 gas Substances 0.000 claims description 23
• 229910052801 chlorine Inorganic materials 0.000 claims description 21
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
• 229910052751 metal Inorganic materials 0.000 claims description 19
• 239000002184 metal Substances 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 18
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 125000005843 halogen group Chemical group 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 150000002923 oximes Chemical class 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 14
• 230000009931 harmful effect Effects 0.000 claims description 14
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
• 239000007787 solid Substances 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 12
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 12
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 11
• 229910052707 ruthenium Inorganic materials 0.000 claims description 11
• 239000002689 soil Substances 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 10
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 10
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 10
• 150000001768 cations Chemical class 0.000 claims description 10
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 10
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
• 210000003802 sputum Anatomy 0.000 claims description 8
• 206010036790 Productive cough Diseases 0.000 claims description 7
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 7
• 239000007788 liquid Substances 0.000 claims description 7
• 230000001717 pathogenic effect Effects 0.000 claims description 7
• 208000024794 sputum Diseases 0.000 claims description 7
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
• 241001465754 Metazoa Species 0.000 claims description 6
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• 206010028980 Neoplasm Diseases 0.000 claims description 5
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 201000011510 cancer Diseases 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
• 230000002538 fungal effect Effects 0.000 claims description 4
• 244000053095 fungal pathogen Species 0.000 claims description 4
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
• 208000036142 Viral infection Diseases 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 238000006467 substitution reaction Methods 0.000 claims description 3
• 230000009385 viral infection Effects 0.000 claims description 3
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
• 239000003429 antifungal agent Substances 0.000 claims description 2
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 2
• 244000000008 fungal human pathogen Species 0.000 claims description 2
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
• 229910052762 osmium Inorganic materials 0.000 claims description 2
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical group [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims 2
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 1
• 108010081348 HRT1 protein Hairy Proteins 0.000 claims 1
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 1
• 206010021703 Indifference Diseases 0.000 claims 1
• 150000001345 alkine derivatives Chemical class 0.000 claims 1
• 125000005577 anthracene group Chemical group 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
• 239000000417 fungicide Substances 0.000 abstract description 20
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 101
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 86
• 241000196324 Embryophyta Species 0.000 description 84
• 239000002585 base Substances 0.000 description 75
• 239000013543 active substance Substances 0.000 description 50
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 48
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 47
• 201000010099 disease Diseases 0.000 description 46
• 239000002904 solvent Substances 0.000 description 46
• 239000002253 acid Substances 0.000 description 45
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 41
• 241000209140 Triticum Species 0.000 description 38
• 235000021307 Triticum Nutrition 0.000 description 38
• 238000006243 chemical reaction Methods 0.000 description 37
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 35
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 30
• 239000000843 powder Substances 0.000 description 30
• 229910052717 sulfur Inorganic materials 0.000 description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
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• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 27
• 235000005822 corn Nutrition 0.000 description 27
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• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
• BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 24
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• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 21
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• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
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• 125000004434 sulfur atom Chemical group 0.000 description 14
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