DE2635665A1 - Antimikrobielle mittel - Google Patents
Antimikrobielle mittelInfo
- Publication number
- DE2635665A1 DE2635665A1 DE19762635665 DE2635665A DE2635665A1 DE 2635665 A1 DE2635665 A1 DE 2635665A1 DE 19762635665 DE19762635665 DE 19762635665 DE 2635665 A DE2635665 A DE 2635665A DE 2635665 A1 DE2635665 A1 DE 2635665A1
- Authority
- DE
- Germany
- Prior art keywords
- butan
- dimethyl
- chlorophenoxy
- optionally substituted
- triazol
- 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.)
- Withdrawn
Links
- 239000004599 antimicrobial Substances 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000000969 carrier Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 229940121375 antifungal agent Drugs 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 3
- 239000003429 antifungal agent Substances 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- -1 acyl radical Chemical class 0.000 description 49
- 239000003921 oil Substances 0.000 description 33
- 235000019198 oils Nutrition 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 239000004480 active ingredient Substances 0.000 description 26
- YXXPNGIZHZHBTQ-UHFFFAOYSA-N butan-2-ol Chemical compound CC[C](C)O YXXPNGIZHZHBTQ-UHFFFAOYSA-N 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 239000000203 mixture Substances 0.000 description 16
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 239000000825 pharmaceutical preparation Substances 0.000 description 9
- QQJIRQMOCFESJB-UHFFFAOYSA-N 1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound CCC(O)CN1C=NC=N1 QQJIRQMOCFESJB-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000000843 anti-fungal effect Effects 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- XTXIOQSXTHUASF-UHFFFAOYSA-N 3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound CC(C)(C)C(O)CN1C=NC=N1 XTXIOQSXTHUASF-UHFFFAOYSA-N 0.000 description 4
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 230000001857 anti-mycotic effect Effects 0.000 description 4
- 239000002543 antimycotic Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241001480043 Arthrodermataceae Species 0.000 description 3
- 241000222122 Candida albicans Species 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 3
- 235000012216 bentonite Nutrition 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 125000000068 chlorophenyl group Chemical group 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
- 230000037304 dermatophytes Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 2
- ONTMEZULVWDYJI-UHFFFAOYSA-N 1-imidazol-1-yl-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CN1C=CN=C1 ONTMEZULVWDYJI-UHFFFAOYSA-N 0.000 description 2
- DSEIATKXRYHZBI-UHFFFAOYSA-N 2-oxobutyl carbamate Chemical compound C(N)(OCC(CC)=O)=O DSEIATKXRYHZBI-UHFFFAOYSA-N 0.000 description 2
- YQEMORVAKMFKLG-UHFFFAOYSA-N 2-stearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 2
- QSHUZBWDCLJHQB-UHFFFAOYSA-N 3,3-dimethyl-1-phenoxy-1-(triazol-1-yl)butan-2-one Chemical class C1=CN=NN1C(C(=O)C(C)(C)C)OC1=CC=CC=C1 QSHUZBWDCLJHQB-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000228212 Aspergillus Species 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 206010007134 Candida infections Diseases 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 208000007163 Dermatomycoses Diseases 0.000 description 2
- 206010012504 Dermatophytosis Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- 241001460074 Microsporum distortum Species 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N Sec-butyl alcohol Natural products CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 208000002474 Tinea Diseases 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 241000223238 Trichophyton Species 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- XJGDGMSHABXLQV-UHFFFAOYSA-N [3-oxo-4-phenoxy-4-(1h-pyrrol-2-yl)butyl] acetate Chemical class C=1C=CNC=1C(C(=O)CCOC(=O)C)OC1=CC=CC=C1 XJGDGMSHABXLQV-UHFFFAOYSA-N 0.000 description 2
- WZCORCSXSQTUHE-UHFFFAOYSA-N [4-(4-chlorophenoxy)-2,2-dimethyl-3-oxo-4-(1,2,4-triazol-1-yl)butyl] n-phenylcarbamate Chemical compound C=1C=C(Cl)C=CC=1OC(N1N=CN=C1)C(=O)C(C)(C)COC(=O)NC1=CC=CC=C1 WZCORCSXSQTUHE-UHFFFAOYSA-N 0.000 description 2
- SZBCYVSVOAGWPA-UHFFFAOYSA-N [4-(4-chlorophenoxy)-2,2-dimethyl-3-oxobutyl] acetate Chemical compound CC(=O)OCC(C)(C)C(=O)COC1=CC=C(Cl)C=C1 SZBCYVSVOAGWPA-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 244000052616 bacterial pathogen Species 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
- 239000011230 binding agent Substances 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 201000003984 candidiasis Diseases 0.000 description 2
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 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
- 239000000945 filler Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates 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
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- GRIVKQQQLYWJJJ-UHFFFAOYSA-N (4-bromo-2,2-dimethyl-3-oxobutyl) acetate Chemical compound CC(=O)OCC(C)(C)C(=O)CBr GRIVKQQQLYWJJJ-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- JHQPBCPBIQTMTC-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)C)OC1=CC=C(Cl)C=C1 JHQPBCPBIQTMTC-UHFFFAOYSA-N 0.000 description 1
- GFCHTFPAFCYTAA-UHFFFAOYSA-N 1-(4-chlorophenoxy)-4-hydroxy-1-imidazol-1-yl-3,3-dimethylbutan-2-one Chemical compound C1=CN=CN1C(C(=O)C(C)(CO)C)OC1=CC=C(Cl)C=C1 GFCHTFPAFCYTAA-UHFFFAOYSA-N 0.000 description 1
- KQSUUFBNYDTNRR-UHFFFAOYSA-N 1-(4-chlorophenoxy)-4-hydroxy-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(CO)C)OC1=CC=C(Cl)C=C1 KQSUUFBNYDTNRR-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- PENKATIOMNAMEM-UHFFFAOYSA-N 2-imidazol-1-ylpentan-3-one Chemical compound CCC(=O)C(C)N1C=CN=C1 PENKATIOMNAMEM-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SONDDAUABBDQGR-UHFFFAOYSA-N 3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound CC(C)C(O)CN1C=NC=N1 SONDDAUABBDQGR-UHFFFAOYSA-N 0.000 description 1
- IPCMTMZTSNRXBQ-UHFFFAOYSA-N 3-o-[4-(4-chlorophenoxy)-2,2-dimethyl-3-oxo-4-(1,2,4-triazol-1-yl)butyl] 1-o-ethyl propanedioate Chemical compound C1=NC=NN1C(C(=O)C(C)(C)COC(=O)CC(=O)OCC)OC1=CC=C(Cl)C=C1 IPCMTMZTSNRXBQ-UHFFFAOYSA-N 0.000 description 1
- SQDROHRXKNLDLP-UHFFFAOYSA-N 4-(1h-pyrrol-2-yl)butan-1-ol Chemical class OCCCCC1=CC=CN1 SQDROHRXKNLDLP-UHFFFAOYSA-N 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 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
- 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
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762635665 DE2635665A1 (de) | 1976-08-07 | 1976-08-07 | Antimikrobielle mittel |
| GB32385/77A GB1545682A (en) | 1976-08-07 | 1977-08-02 | Antimicrobial azolyl-4-hydroxy-butane derivatives |
| FR7724264A FR2360309A1 (fr) | 1976-08-07 | 1977-08-05 | Composition anti-microbienne contenant des derives de 1-azolyl-4-hydroxy-butane |
| BE179934A BE857521A (fr) | 1976-08-07 | 1977-08-05 | Composition anti-microbienne contenant des derives de 1-azolyl-4-hydroxy-butane |
| JP9346077A JPS5326329A (en) | 1976-08-07 | 1977-08-05 | Antibiotics |
| US06/021,295 US4215131A (en) | 1976-08-07 | 1979-03-16 | Antimicrobial agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762635665 DE2635665A1 (de) | 1976-08-07 | 1976-08-07 | Antimikrobielle mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2635665A1 true DE2635665A1 (de) | 1978-02-09 |
Family
ID=5984992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762635665 Withdrawn DE2635665A1 (de) | 1976-08-07 | 1976-08-07 | Antimikrobielle mittel |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4215131A (OSRAM) |
| JP (1) | JPS5326329A (OSRAM) |
| BE (1) | BE857521A (OSRAM) |
| DE (1) | DE2635665A1 (OSRAM) |
| FR (1) | FR2360309A1 (OSRAM) |
| GB (1) | GB1545682A (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0004303A1 (de) * | 1978-03-18 | 1979-10-03 | Bayer Ag | Acylierte 1-Azolyl-2-hydroxy-butan-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| EP0042980A3 (de) * | 1980-06-07 | 1982-01-27 | Bayer Ag | 4-Substituierte 1-Azolyl-l-phenoxy-3,3-dimethyl-butan-2-one und -ole, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5758671A (en) * | 1980-09-25 | 1982-04-08 | Ishihara Sangyo Kaisha Ltd | Phenoxyalkylazole type compound and agricultural and gardening fungicide comprising it |
| DE3119390A1 (de) * | 1981-05-15 | 1982-12-09 | Bayer Ag, 5090 Leverkusen | 3-substituierte 1-azolyl-3-methyl-1-phenoxy-butan-2-one und -ole, verfahren zu iher herstellung und ihre verwendung als fungizide |
| WO2003009815A2 (en) | 2001-07-25 | 2003-02-06 | Biomarin Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
| US20040191315A1 (en) * | 2003-03-24 | 2004-09-30 | Mike Slattery | Office products containing antimicrobial agent |
| CN101287411B (zh) | 2005-04-28 | 2013-03-06 | 普罗秋斯生物医学公司 | 药物信息系统及其用途 |
| JP2010503710A (ja) | 2006-09-18 | 2010-02-04 | ラプトール ファーマシューティカル インコーポレイテッド | 受容体関連タンパク質（ｒａｐ）結合体の投与による肝障害の処置 |
| US20110305751A1 (en) | 2009-02-20 | 2011-12-15 | To-Bbb Holding B.V. | Glutathione-based drug delivery system |
| KR20180114970A (ko) | 2009-05-06 | 2018-10-19 | 라보라토리 스킨 케어, 인크. | 활성제-칼슘 포스페이트 입자 복합체를 포함하는 피부 전달 조성물 및 이들을 이용하는 방법 |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2041771C3 (de) * | 1970-08-22 | 1979-07-26 | Bayer Ag, 5090 Leverkusen | derivate |
| DE2105490C3 (de) * | 1971-02-05 | 1979-06-13 | Bayer Ag, 5090 Leverkusen | 1 -Imidazolylketonderivate |
| US4038404A (en) * | 1972-09-26 | 1977-07-26 | Bayer Aktiengesellschaft | 1,2,4-triazole antimycotic compositions and use thereof |
| DE2324010C3 (de) * | 1973-05-12 | 1981-10-08 | Bayer Ag, 5090 Leverkusen | 1-Substituierte 2-Triazolyl-2-phenoxyäthanol-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Pilzen |
| DE2423987C2 (de) * | 1974-05-17 | 1986-01-16 | Bayer Ag, 5090 Leverkusen | Metallkomplexe von Azolyläthern, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
| DE2429514A1 (de) * | 1974-06-20 | 1976-01-15 | Bayer Ag | Eckige klammer auf 1-imidazolyl-(1) eckige klammer zu- eckige klammer auf 1-(4'-(4''-chlorphenyl)-phenoxy eckige klammer zu-3,3-dimethyl-butan-2-on und seine salze, ein verfahren zu ihrer herstellung als arzneimittel |
| DE2635666A1 (de) * | 1976-08-07 | 1978-02-09 | Bayer Ag | 1-azolyl-4-hydroxy-butan-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und bakterizide |
-
1976
- 1976-08-07 DE DE19762635665 patent/DE2635665A1/de not_active Withdrawn
-
1977
- 1977-08-02 GB GB32385/77A patent/GB1545682A/en not_active Expired
- 1977-08-05 JP JP9346077A patent/JPS5326329A/ja active Pending
- 1977-08-05 BE BE179934A patent/BE857521A/xx unknown
- 1977-08-05 FR FR7724264A patent/FR2360309A1/fr active Granted
-
1979
- 1979-03-16 US US06/021,295 patent/US4215131A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0004303A1 (de) * | 1978-03-18 | 1979-10-03 | Bayer Ag | Acylierte 1-Azolyl-2-hydroxy-butan-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| EP0042980A3 (de) * | 1980-06-07 | 1982-01-27 | Bayer Ag | 4-Substituierte 1-Azolyl-l-phenoxy-3,3-dimethyl-butan-2-one und -ole, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| US4406909A (en) * | 1980-06-07 | 1983-09-27 | Bayer Aktiengesellschaft | Combating fungi with 4-substituted 1-azolyl-1-phenoxy-3,3-dimethyl-butan-2-ones and -ols |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5326329A (en) | 1978-03-11 |
| GB1545682A (en) | 1979-05-10 |
| BE857521A (fr) | 1978-02-06 |
| FR2360309A1 (fr) | 1978-03-03 |
| FR2360309B1 (OSRAM) | 1980-04-18 |
| US4215131A (en) | 1980-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |