JPS6334875B2 - - Google Patents
Info
- Publication number
- JPS6334875B2 JPS6334875B2 JP17552580A JP17552580A JPS6334875B2 JP S6334875 B2 JPS6334875 B2 JP S6334875B2 JP 17552580 A JP17552580 A JP 17552580A JP 17552580 A JP17552580 A JP 17552580A JP S6334875 B2 JPS6334875 B2 JP S6334875B2
- Authority
- JP
- Japan
- Prior art keywords
- trans
- spectrum
- imidazole
- group
- 60mhz
- 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.)
- Expired
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 150000007980 azole derivatives Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 125000003545 alkoxy 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
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 63
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 55
- 238000002329 infrared spectrum Methods 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 43
- 150000001875 compounds Chemical class 0.000 description 43
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 24
- 239000000203 mixture Substances 0.000 description 21
- -1 n -butyl Chemical group 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 14
- 239000012312 sodium hydride Substances 0.000 description 14
- 229910000104 sodium hydride Inorganic materials 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- 239000012230 colorless oil Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 235000009518 sodium iodide Nutrition 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- VZTICRGNQHVZHU-UHFFFAOYSA-N 3,4-dihydro-2h-pyran-2-ylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC=CCC1 VZTICRGNQHVZHU-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- LFDHVZYCGXBNHO-FOIQADDNSA-N [(2r,6r)-6-[(2,6-dichlorophenyl)methoxy]oxan-2-yl]methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC[C@@H]1O[C@@H](OCC=2C(=CC=CC=2Cl)Cl)CCC1 LFDHVZYCGXBNHO-FOIQADDNSA-N 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 230000000842 anti-protozoal effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 150000003527 tetrahydropyrans Chemical group 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- UXJBOJKIQKMCNC-UKRRQHHQSA-N 1-[[(2r,6r)-6-[(2,4-dichlorophenyl)methoxy]oxan-2-yl]methyl]-1,2,4-triazole Chemical compound ClC1=CC(Cl)=CC=C1CO[C@@H]1O[C@@H](CN2N=CN=C2)CCC1 UXJBOJKIQKMCNC-UKRRQHHQSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- KGYDYYQXZDBAQM-YLJYHZDGSA-N [(2r,6r)-6-[(2,4-dichlorophenyl)methoxy]oxan-2-yl]methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC[C@@H]1O[C@@H](OCC=2C(=CC(Cl)=CC=2)Cl)CCC1 KGYDYYQXZDBAQM-YLJYHZDGSA-N 0.000 description 2
- MDTFDWPEBSHZTJ-UYAOXDASSA-N [(2r,6r)-6-[(4-chlorophenyl)methoxy]oxan-2-yl]methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC[C@@H]1O[C@@H](OCC=2C=CC(Cl)=CC=2)CCC1 MDTFDWPEBSHZTJ-UYAOXDASSA-N 0.000 description 2
- ORTCWZWYRCLOPO-NMZBPYGDSA-N [(2r,6r)-6-[2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)ethoxy]oxan-2-yl]methyl 4-methylbenzenesulfonate Chemical compound C1=CC(OC)=CC=C1C(O[C@@H]1O[C@@H](COS(=O)(=O)C=2C=CC(C)=CC=2)CCC1)CC1=CC=C(Cl)C=C1Cl ORTCWZWYRCLOPO-NMZBPYGDSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- WKKHCCZLKYKUDN-UHFFFAOYSA-N (2,6-dichlorophenyl)methanol Chemical compound OCC1=C(Cl)C=CC=C1Cl WKKHCCZLKYKUDN-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- LLELCYHOZXLHTP-UHFFFAOYSA-N (4-chlorophenyl)-(2,4-dichlorophenyl)methanol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)C1=CC=C(Cl)C=C1 LLELCYHOZXLHTP-UHFFFAOYSA-N 0.000 description 1
- PTHGDVCPCZKZKR-UHFFFAOYSA-N (4-chlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C=C1 PTHGDVCPCZKZKR-UHFFFAOYSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MQNYRHSNLFTFTQ-PAOFMCMWSA-N 1-[2-(2,4-dichlorophenyl)-2-[[(2r,6r)-6-[(2,4-dichlorophenyl)methoxy]oxan-2-yl]methoxy]ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1CO[C@@H]1O[C@@H](COC(CN2C=NC=C2)C=2C(=CC(Cl)=CC=2)Cl)CCC1 MQNYRHSNLFTFTQ-PAOFMCMWSA-N 0.000 description 1
- DVNKQRGOUINLLY-DORBDNKASA-N 1-[2-(2,4-dichlorophenyl)-2-[[(2r,6r)-6-[(2,6-dichlorophenyl)methoxy]oxan-2-yl]methoxy]ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OC[C@@H]1O[C@@H](OCC=2C(=CC=CC=2Cl)Cl)CCC1)CN1C=NC=C1 DVNKQRGOUINLLY-DORBDNKASA-N 0.000 description 1
- VBXPCGJHXUUWHL-VNDUYKDKSA-N 1-[2-(4-chlorophenyl)-2-[[(2r,6r)-6-[(2,4-dichlorophenyl)methoxy]oxan-2-yl]methoxy]ethyl]imidazole Chemical compound C1=CC(Cl)=CC=C1C(OC[C@@H]1O[C@@H](OCC=2C(=CC(Cl)=CC=2)Cl)CCC1)CN1C=NC=C1 VBXPCGJHXUUWHL-VNDUYKDKSA-N 0.000 description 1
- FBLXKYHUTGXYDD-QQHBYLCDSA-N 1-[2-[[(2r,6r)-6-(2,4-dichlorophenoxy)oxan-2-yl]methoxy]-2-phenylethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1O[C@H]1O[C@@H](COC(CN2C=NC=C2)C=2C=CC=CC=2)CCC1 FBLXKYHUTGXYDD-QQHBYLCDSA-N 0.000 description 1
- QKNMSMIRUFQWJQ-VNDUYKDKSA-N 1-[2-[[(2r,6r)-6-[(2,4-dichlorophenyl)methoxy]oxan-2-yl]methoxy]-2-phenylethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1CO[C@@H]1O[C@@H](COC(CN2C=NC=C2)C=2C=CC=CC=2)CCC1 QKNMSMIRUFQWJQ-VNDUYKDKSA-N 0.000 description 1
- CSGFUVLQLNLCAO-MLGOLLRUSA-N 1-[[(2r,6r)-6-[(2,6-dichlorophenyl)methoxy]oxan-2-yl]methyl]imidazole Chemical compound ClC1=CC=CC(Cl)=C1CO[C@@H]1O[C@@H](CN2C=NC=C2)CCC1 CSGFUVLQLNLCAO-MLGOLLRUSA-N 0.000 description 1
- ZOLDYCDTIVLZQG-LJDIEGPPSA-N 1-[[(2r,6r)-6-[(4-chlorophenyl)-(2,4-dichlorophenyl)methoxy]oxan-2-yl]methyl]imidazole Chemical compound C1=CC(Cl)=CC=C1C(C=1C(=CC(Cl)=CC=1)Cl)O[C@@H]1O[C@@H](CN2C=NC=C2)CCC1 ZOLDYCDTIVLZQG-LJDIEGPPSA-N 0.000 description 1
- IDBROTWTALVQNQ-LJDIEGPPSA-N 1-[[(2r,6r)-6-[(4-chlorophenyl)-(2-nitrophenyl)methoxy]oxan-2-yl]methyl]imidazole Chemical compound [O-][N+](=O)C1=CC=CC=C1C(C=1C=CC(Cl)=CC=1)O[C@@H]1O[C@@H](CN2C=NC=C2)CCC1 IDBROTWTALVQNQ-LJDIEGPPSA-N 0.000 description 1
- OGJZPAMKWUGELB-HZPDHXFCSA-N 1-[[(2r,6r)-6-[(4-chlorophenyl)methoxy]oxan-2-yl]methyl]imidazole Chemical compound C1=CC(Cl)=CC=C1CO[C@@H]1O[C@@H](CN2C=NC=C2)CCC1 OGJZPAMKWUGELB-HZPDHXFCSA-N 0.000 description 1
- NBLHJSVWAMXADC-APBNVXTGSA-N 1-[[(2r,6r)-6-[1,2-bis(2,4-dichlorophenyl)ethoxy]oxan-2-yl]methyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1CC(C=1C(=CC(Cl)=CC=1)Cl)O[C@@H]1O[C@@H](CN2C=NC=C2)CCC1 NBLHJSVWAMXADC-APBNVXTGSA-N 0.000 description 1
- OVSBCRCCECTNEX-FQXDTITESA-N 1-[[(2r,6r)-6-[1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)ethoxy]oxan-2-yl]methyl]imidazole Chemical compound C1=CC(Cl)=CC=C1C(O[C@@H]1O[C@@H](CN2C=NC=C2)CCC1)CC1=CC=C(Cl)C=C1Cl OVSBCRCCECTNEX-FQXDTITESA-N 0.000 description 1
- TWADRAXGHCPCGM-UCLFCPHBSA-N 1-[[(2r,6r)-6-[2-(2,4-dichlorophenyl)-1-(2,6-dichlorophenyl)ethoxy]oxan-2-yl]methyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1CC(C=1C(=CC=CC=1Cl)Cl)O[C@@H]1O[C@@H](CN2C=NC=C2)CCC1 TWADRAXGHCPCGM-UCLFCPHBSA-N 0.000 description 1
- AMNMQQQMJZSJOF-NUEBVZBTSA-N 1-[[(2r,6r)-6-[2-(2,4-dichlorophenyl)-1-(2-methoxyphenyl)ethoxy]oxan-2-yl]methyl]imidazole Chemical compound COC1=CC=CC=C1C(O[C@@H]1O[C@@H](CN2C=NC=C2)CCC1)CC1=CC=C(Cl)C=C1Cl AMNMQQQMJZSJOF-NUEBVZBTSA-N 0.000 description 1
- XNEHSBYBRVMZKV-HZPDHXFCSA-N 1-[[(2r,6r)-6-phenylmethoxyoxan-2-yl]methyl]imidazole Chemical compound C([C@H]1CCC[C@@H](O1)OCC=1C=CC=CC=1)N1C=CN=C1 XNEHSBYBRVMZKV-HZPDHXFCSA-N 0.000 description 1
- CWXDCDUMMOIGDT-VXGBXAGGSA-N 1-[[(2r,6r)-6-prop-2-ynoxyoxan-2-yl]methyl]imidazole Chemical compound O1[C@@H](OCC#C)CCC[C@@H]1CN1C=NC=C1 CWXDCDUMMOIGDT-VXGBXAGGSA-N 0.000 description 1
- TWOXOAFHUDIFAU-NEPJUHHUSA-N 1-[[(2r,6s)-6-[(2-methylpropan-2-yl)oxy]oxan-2-yl]methyl]imidazole Chemical compound O1[C@@H](OC(C)(C)C)CCC[C@@H]1CN1C=NC=C1 TWOXOAFHUDIFAU-NEPJUHHUSA-N 0.000 description 1
- HIGKGJOKIARKOK-INMVSHNGSA-N 1-[[(2r,6s)-6-[2-(2,4-dichlorophenyl)-1-thiophen-2-ylethoxy]oxan-2-yl]methyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1CC(C=1SC=CC=1)O[C@@H]1O[C@@H](CN2C=NC=C2)CCC1 HIGKGJOKIARKOK-INMVSHNGSA-N 0.000 description 1
- QMWNOAAXZXQNGJ-HUUCEWRRSA-N 1-[[(2r,6s)-6-phenoxyoxan-2-yl]methyl]imidazole Chemical compound O([C@H]1CCC[C@@H](O1)CN1C=NC=C1)C1=CC=CC=C1 QMWNOAAXZXQNGJ-HUUCEWRRSA-N 0.000 description 1
- YNCPXBIZAPNQIJ-UHFFFAOYSA-N 1h-imidazole;sodium Chemical compound [Na].C1=CNC=N1 YNCPXBIZAPNQIJ-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- NTWZHQAXJSJOIB-UHFFFAOYSA-N 2-imidazol-1-yl-1-phenylethanol Chemical compound C=1C=CC=CC=1C(O)CN1C=CN=C1 NTWZHQAXJSJOIB-UHFFFAOYSA-N 0.000 description 1
- CVJNXVLQSKPUGP-UHFFFAOYSA-N 2-imidazol-1-yl-1-phenylethanone Chemical compound C=1C=CC=CC=1C(=O)CN1C=CN=C1 CVJNXVLQSKPUGP-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- YBDQLHBVNXARAU-UHFFFAOYSA-N 2-methyloxane Chemical compound CC1CCCCO1 YBDQLHBVNXARAU-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000131314 Aspergillus candidus Species 0.000 description 1
- 241001225321 Aspergillus fumigatus Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000222178 Candida tropicalis Species 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 201000007336 Cryptococcosis Diseases 0.000 description 1
- 241000221204 Cryptococcus neoformans Species 0.000 description 1
- 241000223233 Cutaneotrichosporon cutaneum Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000122864 Fonsecaea pedrosoi Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000168141 Geotrichum candidum Species 0.000 description 1
- 235000017388 Geotrichum candidum Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241001443590 Naganishia albida Species 0.000 description 1
- 241000893976 Nannizzia gypsea Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000187678 Nocardia asteroides Species 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 241001531356 Phialophora verrucosa Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 241000223253 Rhodotorula glutinis Species 0.000 description 1
- 239000006159 Sabouraud's agar Substances 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000233667 Saprolegnia Species 0.000 description 1
- 241001149963 Sporothrix schenckii Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- 241001459572 Trichophyton interdigitale Species 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 241001058196 Tritrichomonas foetus Species 0.000 description 1
- PHZWEWZUDJCDFJ-IDERCBEYSA-N [(2r,6r)-6-[2-(2,4-dichlorophenyl)-1-phenylethoxy]oxan-2-yl]methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC[C@@H]1O[C@@H](OC(CC=2C(=CC(Cl)=CC=2)Cl)C=2C=CC=CC=2)CCC1 PHZWEWZUDJCDFJ-IDERCBEYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 244000037640 animal pathogen Species 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- MZJUGRUTVANEDW-UHFFFAOYSA-N bromine fluoride Chemical compound BrF MZJUGRUTVANEDW-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 229960004698 dichlorobenzyl alcohol Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019249 food preservative Nutrition 0.000 description 1
- 239000005452 food preservative Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 244000052637 human pathogen Species 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- GVZMYROGYRWDEM-UHFFFAOYSA-M magnesium;2,4-dichloro-1-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=C(Cl)C=C1Cl GVZMYROGYRWDEM-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 239000012449 sabouraud dextrose agar Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical class [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17552580A JPS5799585A (en) | 1980-12-12 | 1980-12-12 | Novel triazole derivative, its preparation, and antimicrobial agent comprising it |
| US06/329,995 US4421758A (en) | 1980-12-12 | 1981-12-11 | Anti-microbial diazole derivatives |
| EP81305846A EP0055059B1 (en) | 1980-12-12 | 1981-12-11 | Diazole and triazole derivatives, processes for their preparation and anti-microbial compositions containing them |
| DE8181305846T DE3169611D1 (en) | 1980-12-12 | 1981-12-11 | Diazole and triazole derivatives, processes for their preparation and anti-microbial compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17552580A JPS5799585A (en) | 1980-12-12 | 1980-12-12 | Novel triazole derivative, its preparation, and antimicrobial agent comprising it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5799585A JPS5799585A (en) | 1982-06-21 |
| JPS6334875B2 true JPS6334875B2 (enrdf_load_stackoverflow) | 1988-07-12 |
Family
ID=15997579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17552580A Granted JPS5799585A (en) | 1980-12-12 | 1980-12-12 | Novel triazole derivative, its preparation, and antimicrobial agent comprising it |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5799585A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0364115U (enrdf_load_stackoverflow) * | 1989-10-27 | 1991-06-21 | ||
| JPH063712U (ja) * | 1992-06-23 | 1994-01-18 | アラコ株式会社 | 自動車の扉構造 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR960031456A (ko) * | 1995-02-07 | 1996-09-17 | 김충환 | 새로운 테트라하이드로피란 유도체 및 그 제조방법 |
-
1980
- 1980-12-12 JP JP17552580A patent/JPS5799585A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0364115U (enrdf_load_stackoverflow) * | 1989-10-27 | 1991-06-21 | ||
| JPH063712U (ja) * | 1992-06-23 | 1994-01-18 | アラコ株式会社 | 自動車の扉構造 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5799585A (en) | 1982-06-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI96859C (fi) | Menetelmä terapeuttisesti käyttökelpoisten fungisidisten triatsoliyhdisteiden valmistamiseksi | |
| US5567817A (en) | Triazole antifungal agents | |
| US5541203A (en) | Triazole antifungal agents | |
| US5962476A (en) | Azolylamine derivative | |
| JP2997947B2 (ja) | トリアゾール化合物およびその用途 | |
| JP3278738B2 (ja) | 抗真菌剤 | |
| EP0237962A2 (de) | 2-Azolylmethyl-2-aryl-1,3-dioxolane und deren Salze, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung | |
| LU85551A1 (fr) | Nouveaux composes azoliques,leur preparation et leur utilisation comme antifongiques et fongicides | |
| JPS638939B2 (enrdf_load_stackoverflow) | ||
| US5011850A (en) | Substituted diazolylalkyl-carbinols, a process for their preparation and their use as antimycotic agents | |
| JPS6258355B2 (enrdf_load_stackoverflow) | ||
| JPS59163374A (ja) | トリアゾ−ル抗真菌剤 | |
| US4894382A (en) | Substituted 1,3-diazolyl-2-propanols and their use as antimycotic agents | |
| EP1474422B1 (en) | R-(-)-1-¬2-(7-CHLOROBENZO-¬B -THIOPHEN-3-Yl-METHOXY)-2-(2,4-DICHLOROPHENYL)ETHYL -1H-IMIDAZOLE | |
| JPH01250356A (ja) | 抗糸菌剤 | |
| JPS6334875B2 (enrdf_load_stackoverflow) | ||
| EP0055059B1 (en) | Diazole and triazole derivatives, processes for their preparation and anti-microbial compositions containing them | |
| JPS6346074B2 (enrdf_load_stackoverflow) | ||
| JPH02172978A (ja) | 置換ビスアゾール、その製造方法およびその医薬としての使用 | |
| JPS6030673B2 (ja) | 抗かび活性を有するエテニルイミダゾ−ル誘導体、その製造法、およびそれを含む製薬組成物その製造に有用な中間物、およびこの中間物の製造法 | |
| JPH06279419A (ja) | 新規トリアゾール誘導体及びこれを有効成分とする抗真菌剤 | |
| US4904682A (en) | Treating mycoses with triazolylalkanols | |
| JPH04356471A (ja) | トリアゾール化合物およびその用途 | |
| JP3437695B2 (ja) | アゾリルアミン誘導体 | |
| US4843089A (en) | Antimycotic agent |