CA1217775A - Substituted tert.-butanol derivatives, processes for their preparation and antimycotic agents containing these compounds - Google Patents
Substituted tert.-butanol derivatives, processes for their preparation and antimycotic agents containing these compoundsInfo
- Publication number
- CA1217775A CA1217775A CA000435743A CA435743A CA1217775A CA 1217775 A CA1217775 A CA 1217775A CA 000435743 A CA000435743 A CA 000435743A CA 435743 A CA435743 A CA 435743A CA 1217775 A CA1217775 A CA 1217775A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- triazol
- alkyl
- case
- methyl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 60
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical class CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 title claims description 70
- 230000008569 process Effects 0.000 title claims description 57
- 238000002360 preparation method Methods 0.000 title claims description 21
- 239000003429 antifungal agent Substances 0.000 title abstract description 3
- -1 phenylacetylenyl Chemical group 0.000 claims abstract description 98
- 239000002253 acid Substances 0.000 claims abstract description 28
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 15
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 15
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000006193 alkinyl group Chemical group 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 103
- 125000004432 carbon atom Chemical group C* 0.000 claims description 83
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000001424 substituent group Chemical group 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims description 15
- 239000011230 binding agent Substances 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 14
- 239000012038 nucleophile Substances 0.000 claims description 14
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- HCPYPLZHFYPWKI-UHFFFAOYSA-N 2,2-bis[(2,4-dichlorophenoxy)methyl]oxirane Chemical compound ClC1=CC(Cl)=CC=C1OCC1(COC=2C(=CC(Cl)=CC=2)Cl)OC1 HCPYPLZHFYPWKI-UHFFFAOYSA-N 0.000 claims description 7
- PCAXFAQKTAIMOR-UHFFFAOYSA-N 2-(chloromethyl)-2-[(2,4-dichlorophenoxy)methyl]oxirane Chemical compound C=1C=C(Cl)C=C(Cl)C=1OCC1(CCl)CO1 PCAXFAQKTAIMOR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 150000002923 oximes Chemical class 0.000 claims description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 4
- 150000002924 oxiranes Chemical class 0.000 claims description 4
- 239000001294 propane Substances 0.000 claims description 4
- GWDZGIBVOWCMMD-UHFFFAOYSA-N 2-(chloromethyl)-2-[(4-chlorophenoxy)methyl]oxirane Chemical compound C=1C=C(Cl)C=CC=1OCC1(CCl)CO1 GWDZGIBVOWCMMD-UHFFFAOYSA-N 0.000 claims description 3
- LJVGHYVQNBMYLY-UHFFFAOYSA-N 2-(chloromethyl)-2-[(4-chlorophenyl)sulfanylmethyl]oxirane Chemical compound C=1C=C(Cl)C=CC=1SCC1(CCl)CO1 LJVGHYVQNBMYLY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 17
- ZCIDECVASLSABQ-UHFFFAOYSA-N 1-(2,4-dichlorophenoxy)-3-(1,2,4-triazol-1-yl)-2-(1,2,4-triazol-1-ylmethyl)propan-2-ol Chemical compound C1=NC=NN1CC(CN1N=CN=C1)(O)COC1=CC=C(Cl)C=C1Cl ZCIDECVASLSABQ-UHFFFAOYSA-N 0.000 claims 2
- XNTJPUQSNYWEDX-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3-(1,2,4-triazol-1-yl)-2-(1,2,4-triazol-1-ylmethyl)propan-2-ol Chemical compound C1=NC=NN1CC(CN1N=CN=C1)(O)COC1=CC=C(Cl)C=C1 XNTJPUQSNYWEDX-UHFFFAOYSA-N 0.000 claims 2
- GBWUOCWASLDOHY-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfanyl-3-(1,2,4-triazol-1-yl)-2-(1,2,4-triazol-1-ylmethyl)propan-2-ol Chemical compound C1=NC=NN1CC(CN1N=CN=C1)(O)CSC1=CC=C(Cl)C=C1 GBWUOCWASLDOHY-UHFFFAOYSA-N 0.000 claims 2
- CATQNWHVWNFOHT-UHFFFAOYSA-N 1-(4-fluorophenoxy)-3-(1,2,4-triazol-1-yl)-2-(1,2,4-triazol-1-ylmethyl)propan-2-ol Chemical compound C1=NC=NN1CC(CN1N=CN=C1)(O)COC1=CC=C(F)C=C1 CATQNWHVWNFOHT-UHFFFAOYSA-N 0.000 claims 2
- JJWIMSXYRXNLKE-UHFFFAOYSA-N 1-(4-phenylphenoxy)-3-(1,2,4-triazol-1-yl)-2-(1,2,4-triazol-1-ylmethyl)propan-2-ol Chemical compound C1=NC=NN1CC(CN1N=CN=C1)(O)COC(C=C1)=CC=C1C1=CC=CC=C1 JJWIMSXYRXNLKE-UHFFFAOYSA-N 0.000 claims 2
- XUBLWHBRZXFQQP-UHFFFAOYSA-N 1-(2,4-dichlorophenoxy)-3-(1,2,4-triazol-4-yl)-2-(1,2,4-triazol-1-ylmethyl)propan-2-ol Chemical compound C1=NN=CN1CC(CN1N=CN=C1)(O)COC1=CC=C(Cl)C=C1Cl XUBLWHBRZXFQQP-UHFFFAOYSA-N 0.000 claims 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 34
- 230000001857 anti-mycotic effect Effects 0.000 abstract description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract description 2
- 125000003943 azolyl group Chemical group 0.000 abstract 1
- 235000013350 formula milk Nutrition 0.000 description 74
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 44
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 239000000243 solution Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 239000000546 pharmaceutical excipient Substances 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 229940093956 potassium carbonate Drugs 0.000 description 10
- 235000011181 potassium carbonates Nutrition 0.000 description 10
- 241000894007 species Species 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound 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
- 235000002639 sodium chloride Nutrition 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- VXJMTPXHQUAFDY-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfanyl-3-(1,2,4-triazol-4-yl)-2-(1,2,4-triazol-1-ylmethyl)propan-2-ol Chemical compound C1=NN=CN1CC(CN1N=CN=C1)(O)CSC1=CC=C(Cl)C=C1 VXJMTPXHQUAFDY-UHFFFAOYSA-N 0.000 description 4
- QYMBUGYOVSCZTI-UHFFFAOYSA-N 2,2-bis(chloromethyl)oxirane Chemical compound ClCC1(CCl)CO1 QYMBUGYOVSCZTI-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000008298 dragée Substances 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XJFZOSUFGSANIF-UHFFFAOYSA-N 3-chloro-2-(chloromethyl)prop-1-ene Chemical compound ClCC(=C)CCl XJFZOSUFGSANIF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000012216 bentonite Nutrition 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229960004756 ethanol Drugs 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- 229960000443 hydrochloric acid Drugs 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- FIKLIMREFOSVIQ-UHFFFAOYSA-N 1-(4-chlorophenoxy)-2-(imidazol-1-ylmethyl)-3,3-dimethylbutan-2-ol Chemical compound C1=CN=CN1CC(O)(C(C)(C)C)COC1=CC=C(Cl)C=C1 FIKLIMREFOSVIQ-UHFFFAOYSA-N 0.000 description 2
- UWGRGRPXQZKCHU-UHFFFAOYSA-N 1-chloro-4-[2-(chloromethyl)prop-2-enoxy]benzene Chemical compound ClCC(=C)COC1=CC=C(Cl)C=C1 UWGRGRPXQZKCHU-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 101100132433 Arabidopsis thaliana VIII-1 gene Proteins 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 241000335423 Blastomyces Species 0.000 description 2
- 208000007163 Dermatomycoses Diseases 0.000 description 2
- 241001480036 Epidermophyton floccosum Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241000206672 Gelidium Species 0.000 description 2
- 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 2
- 208000031888 Mycoses Diseases 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 241000223238 Trichophyton Species 0.000 description 2
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 239000002543 antimycotic Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 201000003984 candidiasis Diseases 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/34—Compounds containing oxirane rings with hydrocarbon radicals, substituted by sulphur, selenium or tellurium atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823232647 DE3232647A1 (de) | 1982-09-02 | 1982-09-02 | Substituierte tert.-butanol-derivate, verfahren zu ihrer herstellung und diese enthaltende antimykotische mittel |
| DEP3232647.5 | 1982-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1217775A true CA1217775A (en) | 1987-02-10 |
Family
ID=6172310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000435743A Expired CA1217775A (en) | 1982-09-02 | 1983-08-31 | Substituted tert.-butanol derivatives, processes for their preparation and antimycotic agents containing these compounds |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4621095A (en]) |
| EP (1) | EP0105166B1 (en]) |
| JP (1) | JPS5965030A (en]) |
| KR (1) | KR840006220A (en]) |
| AT (1) | ATE26710T1 (en]) |
| CA (1) | CA1217775A (en]) |
| DE (2) | DE3232647A1 (en]) |
| DK (1) | DK398483A (en]) |
| ES (1) | ES525297A0 (en]) |
| FI (1) | FI833101A7 (en]) |
| GR (1) | GR79628B (en]) |
| IL (1) | IL69599A (en]) |
| PH (1) | PH22053A (en]) |
| PT (1) | PT77238B (en]) |
| ZA (1) | ZA836480B (en]) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3307217A1 (de) * | 1983-03-02 | 1984-09-06 | Bayer Ag, 5090 Leverkusen | Substituierte 1,3-diazolyl-2-propanole, verfahren zu ihrer herstellung und ihre verwendung als antimykotische mittel |
| DE3311702A1 (de) * | 1983-03-30 | 1984-10-04 | Bayer Ag, 5090 Leverkusen | Fungizide mittel, verfahren zu ihrer herstellung und deren verwendung |
| AU4327585A (en) * | 1984-06-21 | 1986-01-02 | Imperial Chemical Industries Plc | Antifungal azole compounds |
| DE3730871A1 (de) * | 1987-09-15 | 1989-03-23 | Bayer Ag | Bisazolyl-hydroxyalkyl-derivate |
| DE3732384A1 (de) * | 1987-09-25 | 1989-04-06 | Bayer Ag | Bisazolyl-hydroxyalkyl-derivate enthaltende antimykotische mittel |
| US5087620A (en) * | 1990-05-17 | 1992-02-11 | Bristol-Myers Squibb Co. | Controlled dermal penetration enhancement using imidazoles |
| EP0485890A3 (en) * | 1990-11-16 | 1992-07-08 | Hoechst Aktiengesellschaft | Use of 2,3-disubstituate 1-azolyl-propane for inhibiting the pathogenic growth phase of dimorph yeast cell |
| US9668481B2 (en) * | 2013-04-12 | 2017-06-06 | Bayer Cropscience Aktiengesellschaft | Triazole derivatives |
| BR112015025637A2 (pt) * | 2013-04-12 | 2017-07-18 | Bayer Cropscience Ag | novos derivados de triazol |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2851086A1 (de) * | 1978-11-25 | 1980-06-04 | Bayer Ag | Hydroxypropyl-triazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE3011258A1 (de) * | 1980-03-24 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | Fungizide mittel, enthaltend triazolylderivate und verfahren zur bekaempfung von pilzen mit ihnen |
| AU542623B2 (en) * | 1980-05-16 | 1985-02-28 | Bayer Aktiengesellschaft | 1-hydroxyethyl-azole derivatives |
| DE3018866A1 (de) * | 1980-05-16 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | 1-hydroxyethyl-azol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide |
| GB2078719B (en) * | 1980-06-02 | 1984-04-26 | Ici Ltd | Heterocyclic compounds |
| DE3108770A1 (de) * | 1981-03-07 | 1982-09-16 | Bayer Ag, 5090 Leverkusen | Triazolylalkyl-thioether, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide |
| DE3279417D1 (en) * | 1981-03-18 | 1989-03-09 | Ici Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
-
1982
- 1982-09-02 DE DE19823232647 patent/DE3232647A1/de not_active Withdrawn
-
1983
- 1983-08-11 US US06/522,423 patent/US4621095A/en not_active Expired - Fee Related
- 1983-08-22 AT AT83108249T patent/ATE26710T1/de not_active IP Right Cessation
- 1983-08-22 EP EP83108249A patent/EP0105166B1/de not_active Expired
- 1983-08-22 DE DE8383108249T patent/DE3371076D1/de not_active Expired
- 1983-08-23 PT PT77238A patent/PT77238B/pt unknown
- 1983-08-30 IL IL69599A patent/IL69599A/xx unknown
- 1983-08-31 CA CA000435743A patent/CA1217775A/en not_active Expired
- 1983-08-31 FI FI833101A patent/FI833101A7/fi not_active Application Discontinuation
- 1983-08-31 PH PH29475A patent/PH22053A/en unknown
- 1983-08-31 GR GR72345A patent/GR79628B/el unknown
- 1983-09-01 ES ES525297A patent/ES525297A0/es active Granted
- 1983-09-01 JP JP58159130A patent/JPS5965030A/ja active Pending
- 1983-09-01 KR KR1019830004106A patent/KR840006220A/ko not_active Withdrawn
- 1983-09-01 DK DK398483A patent/DK398483A/da unknown
- 1983-09-01 ZA ZA836480A patent/ZA836480B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT77238B (de) | 1986-02-04 |
| EP0105166A1 (de) | 1984-04-11 |
| DK398483A (da) | 1984-03-03 |
| US4621095A (en) | 1986-11-04 |
| IL69599A (en) | 1986-12-31 |
| DK398483D0 (da) | 1983-09-01 |
| FI833101A7 (fi) | 1984-03-03 |
| PH22053A (en) | 1988-05-13 |
| ES8406468A1 (es) | 1984-07-16 |
| IL69599A0 (en) | 1983-11-30 |
| ATE26710T1 (de) | 1987-05-15 |
| EP0105166B1 (de) | 1987-04-22 |
| FI833101A0 (fi) | 1983-08-31 |
| DE3371076D1 (en) | 1987-05-27 |
| JPS5965030A (ja) | 1984-04-13 |
| KR840006220A (ko) | 1984-11-22 |
| GR79628B (en]) | 1984-10-31 |
| ES525297A0 (es) | 1984-07-16 |
| ZA836480B (en) | 1984-05-30 |
| PT77238A (de) | 1983-09-01 |
| DE3232647A1 (de) | 1984-03-08 |
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| Date | Code | Title | Description |
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| MKEX | Expiry |