CA1096873A - Tertiary imidazolyl alcohols, a process for their production and their use as medicaments - Google Patents
Tertiary imidazolyl alcohols, a process for their production and their use as medicamentsInfo
- Publication number
- CA1096873A CA1096873A CA278,773A CA278773A CA1096873A CA 1096873 A CA1096873 A CA 1096873A CA 278773 A CA278773 A CA 278773A CA 1096873 A CA1096873 A CA 1096873A
- Authority
- CA
- Canada
- Prior art keywords
- propan
- imidazol
- dichlorophenyl
- chlorophenyl
- compound
- 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 30
- -1 imidazolyl alcohols Chemical group 0.000 title abstract description 9
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 239000003814 drug Substances 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 239000002253 acid Substances 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 150000007513 acids Chemical class 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 73
- 239000000126 substance Substances 0.000 claims description 16
- 239000011230 binding agent Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- JUOSRJKWNFUIGN-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-(2,4-dichlorophenyl)-3-imidazol-1-ylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Cl)(O)CC1=CC=CC=C1Cl JUOSRJKWNFUIGN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- GZISKBYUAWDLOC-UHFFFAOYSA-N 1,2-bis(2,4-dichlorophenyl)-3-imidazol-1-ylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Cl)(O)CC1=CC=C(Cl)C=C1Cl GZISKBYUAWDLOC-UHFFFAOYSA-N 0.000 claims 2
- KRQZVPBYQGMAMF-UHFFFAOYSA-N 1,2-bis(4-chlorophenyl)-3-imidazol-1-ylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C=CC(Cl)=CC=1)(O)CC1=CC=C(Cl)C=C1 KRQZVPBYQGMAMF-UHFFFAOYSA-N 0.000 claims 2
- VONMUUOEZDAWJV-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-(3,4-dichlorophenyl)-3-imidazol-1-ylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C=C(Cl)C(Cl)=CC=1)(O)CC1=CC=C(Cl)C=C1Cl VONMUUOEZDAWJV-UHFFFAOYSA-N 0.000 claims 2
- XELBHAXLWQLWBT-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-imidazol-1-yl-3-(4-methylphenyl)propan-2-ol Chemical compound C1=CC(C)=CC=C1CC(O)(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 XELBHAXLWQLWBT-UHFFFAOYSA-N 0.000 claims 2
- HOQFEMGTFRJKKV-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-imidazol-1-yl-3-phenylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Cl)(O)CC1=CC=CC=C1 HOQFEMGTFRJKKV-UHFFFAOYSA-N 0.000 claims 2
- HZTDRCTXEMKMGW-UHFFFAOYSA-N 2-(2-bromo-4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-imidazol-1-ylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Br)(O)CC1=CC=C(Cl)C=C1Cl HZTDRCTXEMKMGW-UHFFFAOYSA-N 0.000 claims 2
- XTZYLSPIXCSBGC-UHFFFAOYSA-N 2-(4-chloro-2-methylphenyl)-1-(2-chlorophenyl)-3-imidazol-1-ylpropan-2-ol Chemical compound CC1=CC(Cl)=CC=C1C(O)(CN1C=NC=C1)CC1=CC=CC=C1Cl XTZYLSPIXCSBGC-UHFFFAOYSA-N 0.000 claims 2
- CUMWUKVODSKGHS-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-imidazol-1-yl-3-phenylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C=CC(Cl)=CC=1)(O)CC1=CC=CC=C1 CUMWUKVODSKGHS-UHFFFAOYSA-N 0.000 claims 2
- WNBNNBHAEIDYEV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-3-imidazol-1-ylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Cl)(O)CC1=CC=C(Cl)C=C1 WNBNNBHAEIDYEV-UHFFFAOYSA-N 0.000 claims 1
- UHOSCNRXGNIPNM-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-imidazol-1-ylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C=CC(Cl)=CC=1)(O)CC1=CC=C(Cl)C=C1Cl UHOSCNRXGNIPNM-UHFFFAOYSA-N 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 abstract description 7
- 241000233866 Fungi Species 0.000 abstract description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 abstract description 3
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
- 241000124008 Mammalia Species 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- 229910002651 NO3 Inorganic materials 0.000 description 28
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000000875 corresponding effect Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 150000002366 halogen compounds Chemical class 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229910052749 magnesium Inorganic materials 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229960001701 chloroform Drugs 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- RZUCKMKUIWNURF-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-3-imidazol-1-yl-2-phenylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C=CC=CC=1)(O)CC1=CC=C(Cl)C=C1Cl RZUCKMKUIWNURF-UHFFFAOYSA-N 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 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
- 238000001816 cooling Methods 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- KSHYRBMRYIMWJO-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-3-imidazol-1-ylpropan-2-ol;hydrochloride Chemical compound Cl.C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Cl)(O)CC1=CC=C(Cl)C=C1 KSHYRBMRYIMWJO-UHFFFAOYSA-N 0.000 description 2
- YNCPXBIZAPNQIJ-UHFFFAOYSA-N 1h-imidazole;sodium Chemical compound [Na].C1=CNC=N1 YNCPXBIZAPNQIJ-UHFFFAOYSA-N 0.000 description 2
- VYWPPRLJNVHPEU-UHFFFAOYSA-N 2-chloro-1-(2,4-dichlorophenyl)ethanone Chemical compound ClCC(=O)C1=CC=C(Cl)C=C1Cl VYWPPRLJNVHPEU-UHFFFAOYSA-N 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 238000003747 Grignard reaction Methods 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
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- IWZXSUDUGJRCOC-UHFFFAOYSA-N [1-(4-chlorophenyl)-3-imidazol-1-yl-2-phenylpropan-2-yl] nitrate Chemical group C1=CN=CN1CC(C=1C=CC=CC=1)(O[N+](=O)[O-])CC1=CC=C(Cl)C=C1 IWZXSUDUGJRCOC-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229940095731 candida albicans Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 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
- 230000003287 optical effect Effects 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- SSFYNSQLLPRBKE-UHFFFAOYSA-N (1-imidazol-1-yl-2,3-diphenylpropan-2-yl) nitrate Chemical compound C1=CN=CN1CC(C=1C=CC=CC=1)(O[N+](=O)[O-])CC1=CC=CC=C1 SSFYNSQLLPRBKE-UHFFFAOYSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- PIGJTUPPNWISGT-UHFFFAOYSA-N 1,1-bis(4-chlorophenyl)-2-imidazol-1-ylethanol Chemical compound C=1C=C(Cl)C=CC=1C(C=1C=CC(Cl)=CC=1)(O)CN1C=CN=C1 PIGJTUPPNWISGT-UHFFFAOYSA-N 0.000 description 1
- GIMDPFBLSKQRNP-UHFFFAOYSA-N 1,1-diphenylethanol Chemical compound C=1C=CC=CC=1C(O)(C)C1=CC=CC=C1 GIMDPFBLSKQRNP-UHFFFAOYSA-N 0.000 description 1
- AIPJZPPOFWCJRC-UHFFFAOYSA-N 1,2-dichloro-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Cl)=C1Cl AIPJZPPOFWCJRC-UHFFFAOYSA-N 0.000 description 1
- LBOBESSDSGODDD-UHFFFAOYSA-N 1,3-dichloro-2-(chloromethyl)benzene Chemical compound ClCC1=C(Cl)C=CC=C1Cl LBOBESSDSGODDD-UHFFFAOYSA-N 0.000 description 1
- UOOGZHIUDVOJRC-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-imidazol-1-yl-2-phenylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C=CC=CC=1)(O)CC1=CC=CC=C1Cl UOOGZHIUDVOJRC-UHFFFAOYSA-N 0.000 description 1
- OSPDMLTUAKJKSI-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-imidazol-1-yl-2-phenylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C=CC=CC=1)(O)CC1=CC=C(Cl)C=C1 OSPDMLTUAKJKSI-UHFFFAOYSA-N 0.000 description 1
- PVASIGJRAODVPY-UHFFFAOYSA-N 1-[3-(2,6-dichlorophenyl)-2-phenylpropyl]imidazole Chemical compound ClC1=C(C(=CC=C1)Cl)CC(CN1C=NC=C1)C1=CC=CC=C1 PVASIGJRAODVPY-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- HEEAGMIMVCGCRV-UHFFFAOYSA-N 1-chloro-2-(2,4-dichlorophenyl)-3-(2,6-dichlorophenyl)propan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCl)(O)CC1=C(Cl)C=CC=C1Cl HEEAGMIMVCGCRV-UHFFFAOYSA-N 0.000 description 1
- BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 description 1
- WCDFMPVITAWTGR-UHFFFAOYSA-N 1-imidazol-1-ylpropan-2-ol Chemical compound CC(O)CN1C=CN=C1 WCDFMPVITAWTGR-UHFFFAOYSA-N 0.000 description 1
- QSWSKDXFOIOXKW-UHFFFAOYSA-N 1h-imidazole;nitric acid Chemical compound O[N+]([O-])=O.C1=CNC=N1 QSWSKDXFOIOXKW-UHFFFAOYSA-N 0.000 description 1
- OAMHTTBNEJBIKA-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanone Chemical compound ClC(Cl)(Cl)C(=O)C1=CC=CC=C1 OAMHTTBNEJBIKA-UHFFFAOYSA-N 0.000 description 1
- IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 description 1
- DOFHQRKXZIVLCI-UHFFFAOYSA-N 2-(2-bromo-4-chlorophenyl)-1-(2-chlorophenyl)-3-imidazol-1-ylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Br)(O)CC1=CC=CC=C1Cl DOFHQRKXZIVLCI-UHFFFAOYSA-N 0.000 description 1
- OWKBZANFLAHNFV-UHFFFAOYSA-N 2-(2-bromo-4-chlorophenyl)-1-(3,4-dichlorophenyl)-3-imidazol-1-ylpropan-2-ol Chemical compound C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Br)(O)CC1=CC=C(Cl)C(Cl)=C1 OWKBZANFLAHNFV-UHFFFAOYSA-N 0.000 description 1
- SOGLGKRIVMZMSK-UHFFFAOYSA-N 2-chloro-1-(2-chlorophenyl)ethanone Chemical compound ClCC(=O)C1=CC=CC=C1Cl SOGLGKRIVMZMSK-UHFFFAOYSA-N 0.000 description 1
- MCRINSAETDOKDE-UHFFFAOYSA-N 2-chloro-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CCl)C=C1 MCRINSAETDOKDE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 206010017533 Fungal infection Diseases 0.000 description 1
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- CQQWACINDSICNY-UHFFFAOYSA-N [1,2-bis(2,4-dichlorophenyl)-3-imidazol-1-ylpropan-2-yl] nitrate Chemical compound C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Cl)(O[N+](=O)[O-])CC1=CC=C(Cl)C=C1Cl CQQWACINDSICNY-UHFFFAOYSA-N 0.000 description 1
- VWINOIYFMDWSSG-UHFFFAOYSA-N [1-(2,4-dichlorophenyl)-2-(3,4-dichlorophenyl)-3-imidazol-1-ylpropan-2-yl] nitrate Chemical compound C1=CN=CN1CC(C=1C=C(Cl)C(Cl)=CC=1)(O[N+](=O)[O-])CC1=CC=C(Cl)C=C1Cl VWINOIYFMDWSSG-UHFFFAOYSA-N 0.000 description 1
- HGCCSFKDSTYIMZ-UHFFFAOYSA-N [1-(2-chlorophenyl)-2-(2,4-dichlorophenyl)-3-imidazol-1-ylpropan-2-yl] nitrate Chemical compound C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Cl)(O[N+](=O)[O-])CC1=CC=CC=C1Cl HGCCSFKDSTYIMZ-UHFFFAOYSA-N 0.000 description 1
- SQIAGPJEPCRNLH-UHFFFAOYSA-N [1-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-2-imidazol-1-ylethyl] nitrate Chemical compound C=1C=C(Cl)C=CC=1C(C=1C(=CC(Cl)=CC=1)Cl)(O[N+](=O)[O-])CN1C=CN=C1 SQIAGPJEPCRNLH-UHFFFAOYSA-N 0.000 description 1
- DQZZWDCVLUHETB-UHFFFAOYSA-N [2-(2-bromo-4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-imidazol-1-ylpropan-2-yl] nitrate Chemical compound C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Br)(O[N+](=O)[O-])CC1=CC=C(Cl)C=C1Cl DQZZWDCVLUHETB-UHFFFAOYSA-N 0.000 description 1
- PJMNPDIHBGROIC-UHFFFAOYSA-N [2-(2-bromo-4-chlorophenyl)-1-(2-chlorophenyl)-3-imidazol-1-ylpropan-2-yl] nitrate Chemical compound C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Br)(O[N+](=O)[O-])CC1=CC=CC=C1Cl PJMNPDIHBGROIC-UHFFFAOYSA-N 0.000 description 1
- FNJHPXFUXRCIKW-UHFFFAOYSA-N [2-(2-bromo-4-chlorophenyl)-1-imidazol-1-yl-3-phenylpropan-2-yl] nitrate Chemical compound C1=CN=CN1CC(C=1C(=CC(Cl)=CC=1)Br)(O[N+](=O)[O-])CC1=CC=CC=C1 FNJHPXFUXRCIKW-UHFFFAOYSA-N 0.000 description 1
- FGCJJHJGGWLTPI-UHFFFAOYSA-N [2-(4-chlorophenyl)-1-imidazol-1-yl-3-phenylpropan-2-yl] nitrate Chemical compound C1=CN=CN1CC(C=1C=CC(Cl)=CC=1)(O[N+](=O)[O-])CC1=CC=CC=C1 FGCJJHJGGWLTPI-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- GAPFWGOSHOCNBM-UHFFFAOYSA-N isopropyl nitrate Chemical compound CC(C)O[N+]([O-])=O GAPFWGOSHOCNBM-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- A61P31/10—Antimycotics
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2623129.8 | 1976-05-22 | ||
| DE2623129A DE2623129C3 (de) | 1976-05-22 | 1976-05-22 | U-Diphenyl-3-(imidazol-l-yl) -propan-2-ole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1096873A true CA1096873A (en) | 1981-03-03 |
Family
ID=5978816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA278,773A Expired CA1096873A (en) | 1976-05-22 | 1977-05-19 | Tertiary imidazolyl alcohols, a process for their production and their use as medicaments |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4358458A (en, 2012) |
| JP (1) | JPS52142069A (en, 2012) |
| AT (1) | AT353264B (en, 2012) |
| AU (1) | AU513805B2 (en, 2012) |
| BE (1) | BE854886A (en, 2012) |
| CA (1) | CA1096873A (en, 2012) |
| CH (1) | CH630077A5 (en, 2012) |
| DE (1) | DE2623129C3 (en, 2012) |
| DK (1) | DK145644C (en, 2012) |
| FI (1) | FI771618A7 (en, 2012) |
| FR (1) | FR2351969A1 (en, 2012) |
| GB (1) | GB1532156A (en, 2012) |
| HU (1) | HU175143B (en, 2012) |
| IL (1) | IL52073A (en, 2012) |
| IN (1) | IN146218B (en, 2012) |
| LU (1) | LU77378A1 (en, 2012) |
| NL (1) | NL7705584A (en, 2012) |
| NO (1) | NO146394C (en, 2012) |
| PL (1) | PL104273B1 (en, 2012) |
| SE (1) | SE434640B (en, 2012) |
| ZA (1) | ZA772984B (en, 2012) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2736122A1 (de) * | 1977-08-11 | 1979-02-22 | Basf Ag | Fungizide |
| JPS5823442Y2 (ja) * | 1977-11-26 | 1983-05-19 | 日立造船株式会社 | 圧延用ミルのウェブガイド調整装置 |
| US4246274A (en) * | 1978-05-10 | 1981-01-20 | Bayer Aktiengesellschaft | Antimycotic hydroxypropyl-imidazoles |
| DE2851143A1 (de) * | 1978-11-25 | 1980-06-04 | Bayer Ag | Fluorenyl-azolylmethyl-carbinole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2851086A1 (de) * | 1978-11-25 | 1980-06-04 | Bayer Ag | Hydroxypropyl-triazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2851116A1 (de) * | 1978-11-25 | 1980-06-12 | Bayer Ag | Hydroxyethyl-azole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4654332A (en) | 1979-03-07 | 1987-03-31 | Imperial Chemical Industries Plc | Heterocyclic compounds |
| BR8001317A (pt) * | 1979-03-07 | 1980-11-04 | Ici Ltd | Composto fungicida, processo para preparar um composto, sal ou complexo de metal e composicao fungicida |
| US4551469A (en) * | 1979-03-07 | 1985-11-05 | Imperial Chemical Industries Plc | Antifungal triazole ethanol derivatives |
| US4927839A (en) * | 1979-03-07 | 1990-05-22 | Imperial Chemical Industries Plc | Method of preventing fungal attack on wood, hides, leather or paint films using a triazole |
| DE2912288A1 (de) * | 1979-03-28 | 1980-10-09 | Bayer Ag | Verfahren zur herstellung von hydroxyethyl-azolen |
| JPS5828083Y2 (ja) * | 1979-04-25 | 1983-06-18 | ナショナル住宅産業株式会社 | 垂直パネルと水平パネルの連結金具 |
| DE2946956A1 (de) * | 1979-11-21 | 1981-06-19 | Bayer Ag, 5090 Leverkusen | Hydroxybutyl-imidazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE2946957A1 (de) * | 1979-11-21 | 1981-06-04 | Bayer Ag, 5090 Leverkusen | Antimikrobielle mittel |
| DE3003933A1 (de) * | 1980-02-04 | 1981-08-13 | Basf Ag, 6700 Ludwigshafen | (beta) -imidazolylalkohole, verfahren zu ihrer herstellung, diese enthaltende fungizide und verfahren zur bekaempfung von pilzen mit ihnen |
| DE3018865A1 (de) * | 1980-05-16 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | Antimikrobielle mittel |
| AU542623B2 (en) * | 1980-05-16 | 1985-02-28 | Bayer Aktiengesellschaft | 1-hydroxyethyl-azole derivatives |
| EP0065814B1 (en) * | 1981-05-12 | 1985-08-14 | Imperial Chemical Industries Plc | 1,1-bis phenylalkan-1-ols and processes for their preparation |
| JPS57188533A (en) * | 1981-05-12 | 1982-11-19 | Ici Ltd | Manufacture of halohydrin and halohydrin compounds |
| US4435399A (en) | 1981-07-18 | 1984-03-06 | Pfizer Inc. | 2-Aryl-1-(imidazol-1-yl)-8-(4-piperazin-1-ylphenoxy) octan-2-ol antifungal agents |
| GB8306351D0 (en) * | 1983-03-08 | 1983-04-13 | Ici Plc | Azole fungicides |
| DE3579347D1 (de) * | 1984-04-05 | 1990-10-04 | Ici Plc | Azolylpropanole. |
| US4766140A (en) * | 1984-06-18 | 1988-08-23 | Eli Lilly And Company | Method of inhibiting aromatase |
| DE3427844A1 (de) * | 1984-07-27 | 1986-02-06 | Bayer Ag, 5090 Leverkusen | Substituierte hydroxyalkyl-azole, verfahren zu ihrer herstellung sowie diese enthaltende antimykotische mittel |
| US4859693A (en) * | 1988-08-10 | 1989-08-22 | E. I. Du Pont De Nemours And Company | Antiinflammatory carbinoloimidazoles |
| NZ270418A (en) | 1994-02-07 | 1997-09-22 | Eisai Co Ltd | Polycyclic triazole & imidazole derivatives, antifungal compositions |
| US11058738B2 (en) | 2015-07-09 | 2021-07-13 | Wyzsza Szkola Medyczna W Bialymstoku | Herbal preparation for accelerating wounds and skin inflammations healing, especially for treatment of herpes and acne, and its application |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU557755A3 (ru) * | 1968-08-19 | 1977-05-05 | Янссен Фармасьютика Н.В. (Фирма) | Способ получени производных имидазола |
| US3839574A (en) * | 1968-08-19 | 1974-10-01 | Janssen Pharmaceutica Nv | Antifungal and antibacterial compositions of certain imidazoles and methods of using same |
| US3658813A (en) * | 1970-01-13 | 1972-04-25 | Janssen Pharmaceutica Nv | 1-(beta-aryl-beta-(r-oxy)-ethyl)-imidazoles |
| US3679697A (en) * | 1970-10-08 | 1972-07-25 | Searle & Co | 1-({62 -halophenethyl)imidazoles |
-
1976
- 1976-05-22 DE DE2623129A patent/DE2623129C3/de not_active Expired
-
1977
- 1977-05-06 CH CH569677A patent/CH630077A5/de not_active IP Right Cessation
- 1977-05-12 AT AT341677A patent/AT353264B/de not_active IP Right Cessation
- 1977-05-12 IL IL52073A patent/IL52073A/xx unknown
- 1977-05-12 IN IN714/CAL/77A patent/IN146218B/en unknown
- 1977-05-13 US US05/796,613 patent/US4358458A/en not_active Expired - Lifetime
- 1977-05-16 AU AU25176/77A patent/AU513805B2/en not_active Expired
- 1977-05-18 DK DK220177A patent/DK145644C/da not_active IP Right Cessation
- 1977-05-18 ZA ZA00772984A patent/ZA772984B/xx unknown
- 1977-05-18 FR FR7715321A patent/FR2351969A1/fr active Granted
- 1977-05-19 CA CA278,773A patent/CA1096873A/en not_active Expired
- 1977-05-20 SE SE7705939A patent/SE434640B/xx not_active IP Right Cessation
- 1977-05-20 PL PL1977198268A patent/PL104273B1/pl unknown
- 1977-05-20 LU LU77378A patent/LU77378A1/xx unknown
- 1977-05-20 FI FI771618A patent/FI771618A7/fi not_active Application Discontinuation
- 1977-05-20 HU HU77NO215A patent/HU175143B/hu unknown
- 1977-05-20 NO NO771767A patent/NO146394C/no unknown
- 1977-05-20 GB GB21297/77A patent/GB1532156A/en not_active Expired
- 1977-05-20 NL NL7705584A patent/NL7705584A/xx not_active Application Discontinuation
- 1977-05-21 JP JP5822477A patent/JPS52142069A/ja active Pending
- 1977-05-23 BE BE2055928A patent/BE854886A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI771618A7 (en, 2012) | 1977-11-23 |
| IL52073A0 (en) | 1977-07-31 |
| SE434640B (sv) | 1984-08-06 |
| LU77378A1 (en, 2012) | 1977-08-29 |
| US4358458A (en) | 1982-11-09 |
| AU2517677A (en) | 1978-11-23 |
| DK145644B (da) | 1983-01-10 |
| DE2623129B2 (de) | 1979-08-09 |
| SE7705939L (sv) | 1977-11-23 |
| NO771767L (no) | 1977-11-23 |
| PL104273B1 (pl) | 1979-08-31 |
| DE2623129C3 (de) | 1980-04-10 |
| BE854886A (fr) | 1977-09-16 |
| IN146218B (en, 2012) | 1979-03-24 |
| PL198268A1 (pl) | 1978-04-10 |
| ZA772984B (en) | 1978-05-30 |
| GB1532156A (en) | 1978-11-15 |
| HU175143B (hu) | 1980-05-28 |
| AU513805B2 (en) | 1981-01-08 |
| NO146394C (no) | 1982-09-22 |
| NO146394B (no) | 1982-06-14 |
| DK145644C (da) | 1983-07-04 |
| AT353264B (de) | 1979-11-12 |
| CH630077A5 (de) | 1982-05-28 |
| ATA341677A (de) | 1979-04-15 |
| IL52073A (en) | 1981-02-27 |
| NL7705584A (nl) | 1977-11-24 |
| FR2351969A1 (fr) | 1977-12-16 |
| DK220177A (da) | 1977-11-23 |
| FR2351969B1 (en, 2012) | 1981-01-09 |
| JPS52142069A (en) | 1977-11-26 |
| DE2623129A1 (de) | 1977-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1096873A (en) | Tertiary imidazolyl alcohols, a process for their production and their use as medicaments | |
| US3940414A (en) | 1-Phenoxy-[imidazolyl-(1)]-2-hydroxy-alkanes | |
| CA1212952A (en) | 1-phenyl-2-triazolyl-ethyl ether derivatives and their use as fungicides | |
| HU189143B (en) | Process for preparing 2-/2,4-difluoro-phenyl/-1,3-bis/1h-1,2,4-triazol-1-yl/-propan-2-ol derivatives | |
| US4514412A (en) | Substituted imidazole derivatives and their use as anti-thrombosis agents | |
| CA1123831A (en) | Imidazolyl ethyl oxyalkoxy derivatives and thio analogues thereof | |
| US3940415A (en) | 1-(Imidazolyl-1)-2-aryloxy-3-hydroxy-alkanes | |
| AU600107B2 (en) | 4-(4-(4-((2-(2,4-difluorophenyl)-2-(1h-azolylmethyl)-1,3- dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl) triazolones | |
| US3882142A (en) | 1,2-Dialkyl-3,5-diphenyl pyrazolium salts | |
| IE45462B1 (en) | Novel1-(2-r-ethyl)-1h-1,2,4-triazoles | |
| GB2136801A (en) | Fungicidal N-acyl-1-aryl-2-azolyl-ethylamines | |
| US4264772A (en) | Combating fungi with 1-phenyl-1-oximino-2-(1,2,4-triazol-1-yl)-ethanes | |
| EP0050298A2 (de) | 1-(1,3-Dioxolan-2-ylmethyl)-azole, ihre Salze, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| US3839574A (en) | Antifungal and antibacterial compositions of certain imidazoles and methods of using same | |
| US4960911A (en) | Process for the preparation of oxiranes | |
| HU211515A9 (en) | Optically active triazole derivatives and compositions | |
| US4331675A (en) | Combating fungi with triazolyl-alkenes | |
| NO165104B (no) | Analogifremgangsmaate til fremstilling av terapeutisk aktive 1, 1-disubstituerte cyklopropanderivater. | |
| EP0034276B1 (de) | Phenylpiperazinderivate von 1,3,4-Oxadiazolylphenolen, ihre Herstellung und diese enthaltende therapeutische Mittel | |
| US4831151A (en) | Antimicrobial imidazolium derivatives | |
| US4956470A (en) | 1,3-disubstituted/imidazolium salts | |
| EP0152596A1 (de) | Neue 1,3-Dioxolanylderivate, Verfahren zu ihrer Herstellung, ihre Verwendung und diese Verbindungen enthaltendes Arzneimittel | |
| DE69628597T2 (de) | Verfahren zur herstellung biologisch aktiver derivate des 1,2,4-triazols und in diesem verfahren nuetzliche zwischenprodukte | |
| CA1287634C (en) | Dihydrobenzo¬b|thiophenes and pharmaceutical compositions thereof useful as antifungals | |
| PT86890B (pt) | Processo para a preparacao de 1-(1-aril-2-hidroxi-etil-)-imidazois e dos seus sais e de composicoes farmaceuticas que os contem |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |