TW201103429A - Triazole compounds carrying a sulfur substituent XI - Google Patents

Info

Publication number

TW201103429A

TW201103429A TW099120000A TW99120000A TW201103429A TW 201103429 A TW201103429 A TW 201103429A TW 099120000 A TW099120000 A TW 099120000A TW 99120000 A TW99120000 A TW 99120000A TW 201103429 A TW201103429 A TW 201103429A

Authority

TW

Taiwan

Prior art keywords

het

group

compound

alkyl

formula

Prior art date

2009-06-18

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• -1 Triazole compounds Chemical class 0.000 title claims abstract description 479
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title abstract description 14
• 150000001875 compounds Chemical class 0.000 claims abstract description 953
• 239000000203 mixture Substances 0.000 claims abstract description 117
• 238000000034 method Methods 0.000 claims abstract description 48
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 177
• 125000000217 alkyl group Chemical group 0.000 claims description 158
• 125000003545 alkoxy group Chemical group 0.000 claims description 78
• 239000002585 base Substances 0.000 claims description 68
• 125000001424 substituent group Chemical group 0.000 claims description 66
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 239000001257 hydrogen Substances 0.000 claims description 50
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 45
• 241000233866 Fungi Species 0.000 claims description 41
• 239000007789 gas Substances 0.000 claims description 40
• 239000000463 material Substances 0.000 claims description 40
• 125000000623 heterocyclic group Chemical group 0.000 claims description 37
• 125000005842 heteroatom Chemical group 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 33
• 229910052731 fluorine Inorganic materials 0.000 claims description 31
• 239000011737 fluorine Substances 0.000 claims description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
• 150000002431 hydrogen Chemical group 0.000 claims description 29
• 125000000304 alkynyl group Chemical group 0.000 claims description 28
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 28
• 229910052794 bromium Inorganic materials 0.000 claims description 27
• 229920006395 saturated elastomer Polymers 0.000 claims description 27
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
• 229910052717 sulfur Inorganic materials 0.000 claims description 25
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
• 125000003342 alkenyl group Chemical group 0.000 claims description 20
• 125000001188 haloalkyl group Chemical group 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
• 150000002923 oximes Chemical class 0.000 claims description 15
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 14
• 150000002367 halogens Chemical group 0.000 claims description 14
• 229910052751 metal Inorganic materials 0.000 claims description 14
• 239000002184 metal Substances 0.000 claims description 14
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 14
• 229910052707 ruthenium Inorganic materials 0.000 claims description 14
• 241001465754 Metazoa Species 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 150000001768 cations Chemical class 0.000 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 11
• 125000004414 alkyl thio group Chemical group 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 11
• 125000002837 carbocyclic group Chemical group 0.000 claims description 11
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 239000002689 soil Substances 0.000 claims description 11
• 239000007787 solid Substances 0.000 claims description 11
• 125000001931 aliphatic group Chemical group 0.000 claims description 10
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 10
• 125000006612 decyloxy group Chemical group 0.000 claims description 10
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 10
• 125000001072 heteroaryl group Chemical group 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
• 206010028980 Neoplasm Diseases 0.000 claims description 9
• 229910052783 alkali metal Inorganic materials 0.000 claims description 9
• 201000011510 cancer Diseases 0.000 claims description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 150000001721 carbon Chemical group 0.000 claims description 8
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
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• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
• 125000004149 thio group Chemical group *S* 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 7
• 150000003254 radicals Chemical class 0.000 claims description 7
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
• 230000009385 viral infection Effects 0.000 claims description 6
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
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• 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 239000000126 substance Substances 0.000 claims description 5
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
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• 239000003814 drug Substances 0.000 claims description 4
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• 230000001717 pathogenic effect Effects 0.000 claims description 4
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000006413 ring segment Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 3
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 3
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
• 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 3
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
• 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 claims description 3
• 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 claims description 3
• 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 claims description 3
• 239000003429 antifungal agent Substances 0.000 claims description 3
• 229940121375 antifungal agent Drugs 0.000 claims description 3
• 101150111293 cor-1 gene Proteins 0.000 claims description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 229910052762 osmium Inorganic materials 0.000 claims description 3
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical group [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 238000006467 substitution reaction Methods 0.000 claims description 3
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
• 125000001425 triazolyl group Chemical group 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 2
• 244000000008 fungal human pathogen Species 0.000 claims description 2
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
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• 125000001544 thienyl group Chemical group 0.000 claims description 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
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