NO128571B - - Google Patents
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- Publication number
- NO128571B NO128571B NO93170A NO93170A NO128571B NO 128571 B NO128571 B NO 128571B NO 93170 A NO93170 A NO 93170A NO 93170 A NO93170 A NO 93170A NO 128571 B NO128571 B NO 128571B
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- denotes
- diphenyl
- imidazolyl
- acetic acid
- Prior art date
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- -1 phenyl-imidazolyl Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 150000002460 imidazoles Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
- 238000002844 melting Methods 0.000 description 33
- 230000008018 melting Effects 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
- 239000013078 crystal Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- OMLSYNQYPRJYAR-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=NC=CN1 OMLSYNQYPRJYAR-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 230000000843 anti-fungal effect Effects 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- BMEHATQTULZMSC-UHFFFAOYSA-N methyl 2,2-bis(4-chlorophenyl)-2-(1h-imidazol-2-yl)acetate Chemical compound C=1C=C(Cl)C=CC=1C(C=1C=CC(Cl)=CC=1)(C(=O)OC)C1=NC=CN1 BMEHATQTULZMSC-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- IZPXHZWRFDQWLT-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1-morpholin-4-yl-2,2-diphenylethanone Chemical compound N=1C=CNC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C(=O)N1CCOCC1 IZPXHZWRFDQWLT-UHFFFAOYSA-N 0.000 description 3
- 241001480043 Arthrodermataceae Species 0.000 description 3
- 241000222122 Candida albicans Species 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 125000005521 carbonamide group Chemical group 0.000 description 3
- 239000000969 carrier 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
- 230000037304 dermatophytes Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IQDLKFJCEIJFGN-UHFFFAOYSA-N ethyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCC)C1=NC=CN1 IQDLKFJCEIJFGN-UHFFFAOYSA-N 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- PRRHXUDAIBCCOD-UHFFFAOYSA-N propyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCCC)C1=NC=CN1 PRRHXUDAIBCCOD-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XQYVDDAXTYTKDB-UHFFFAOYSA-N 2-chloro-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)N)C1=CC=CC=C1 XQYVDDAXTYTKDB-UHFFFAOYSA-N 0.000 description 2
- NFHKZAUDRWRXMZ-UHFFFAOYSA-N 2-chloro-2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)Cl)C1=CC=CC=C1 NFHKZAUDRWRXMZ-UHFFFAOYSA-N 0.000 description 2
- RQCVNIVJMBXZRT-UHFFFAOYSA-N 2-methylpropyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCC(C)C)C1=NC=CN1 RQCVNIVJMBXZRT-UHFFFAOYSA-N 0.000 description 2
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 208000007163 Dermatomycoses Diseases 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 2
- 229960003942 amphotericin b Drugs 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229940095731 candida albicans Drugs 0.000 description 2
- 201000003984 candidiasis Diseases 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 2
- 229960002327 chloral hydrate Drugs 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- YCMAVBIZWABQFF-UHFFFAOYSA-N methyl 2,2-bis(4-bromophenyl)-2-(1h-imidazol-2-yl)acetate Chemical compound C=1C=C(Br)C=CC=1C(C=1C=CC(Br)=CC=1)(C(=O)OC)C1=NC=CN1 YCMAVBIZWABQFF-UHFFFAOYSA-N 0.000 description 2
- KQPURLPHEFAXQG-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-bis(4-methoxyphenyl)acetate Chemical compound C=1C=C(OC)C=CC=1C(C=1C=CC(OC)=CC=1)(C(=O)OC)C1=NC=CN1 KQPURLPHEFAXQG-UHFFFAOYSA-N 0.000 description 2
- ILVSUJHMWHCKOI-UHFFFAOYSA-N methyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OC)C1=CC=CC=C1 ILVSUJHMWHCKOI-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder 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
- 241000894007 species Species 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- UIMCHVXWEUZKGZ-UHFFFAOYSA-N 2-(1H-imidazol-2-yl)-2,2-diphenyl-1-piperidin-1-ylethanone Chemical compound N=1C=CNC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C(=O)N1CCCCC1 UIMCHVXWEUZKGZ-UHFFFAOYSA-N 0.000 description 1
- XEZZSIVYLCTXPO-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N)C1=NC=CN1 XEZZSIVYLCTXPO-UHFFFAOYSA-N 0.000 description 1
- PTKAGHMFWYFHBU-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C#N)C1=NC=CN1 PTKAGHMFWYFHBU-UHFFFAOYSA-N 0.000 description 1
- SEHVKRKEBXXVIB-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-n,n-dimethyl-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N(C)C)C1=NC=CN1 SEHVKRKEBXXVIB-UHFFFAOYSA-N 0.000 description 1
- FGOQDFWSJWDDSH-UHFFFAOYSA-N 2-chloro-1-morpholin-4-yl-2,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C(=O)N1CCOCC1 FGOQDFWSJWDDSH-UHFFFAOYSA-N 0.000 description 1
- PECMDNFVBBZHDH-UHFFFAOYSA-N 2-chloro-2,2-diphenyl-1-piperidin-1-ylethanone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C(=O)N1CCCCC1 PECMDNFVBBZHDH-UHFFFAOYSA-N 0.000 description 1
- WHWDUAPSUGLGSD-UHFFFAOYSA-N 2-chloro-n,n-dimethyl-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)N(C)C)C1=CC=CC=C1 WHWDUAPSUGLGSD-UHFFFAOYSA-N 0.000 description 1
- OHAXWRDDNKBCCD-UHFFFAOYSA-N 2-chloro-n-methyl-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)NC)C1=CC=CC=C1 OHAXWRDDNKBCCD-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- CGJVFUZUKVZYOB-UHFFFAOYSA-N 2-methylpropyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OCC(C)C)C1=CC=CC=C1 CGJVFUZUKVZYOB-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
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- 241000894006 Bacteria Species 0.000 description 1
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- 241000700199 Cavia porcellus Species 0.000 description 1
- CDEMHJCJMMOFMB-UHFFFAOYSA-M ClC1=CC=C([Mg]Br)C=C1 Chemical compound ClC1=CC=C([Mg]Br)C=C1 CDEMHJCJMMOFMB-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
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- 241000224432 Entamoeba histolytica Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 1
- 201000002563 Histoplasmosis Diseases 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
- 241001502500 Trichomonadida Species 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- ZRJNGFJIBZKXTP-UHFFFAOYSA-M [Br-].CC1=CC=C([Mg+])C=C1 Chemical compound [Br-].CC1=CC=C([Mg+])C=C1 ZRJNGFJIBZKXTP-UHFFFAOYSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- CFGHWLWBJBVEJC-UHFFFAOYSA-N benzyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C(=O)OCC1=CC=CC=C1 CFGHWLWBJBVEJC-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007853 buffer solution 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940007078 entamoeba histolytica Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- SLRLUHKUYPGESO-UHFFFAOYSA-N ethyl 2-(1h-imidazol-2-yl)-2-methyl-3-phenylpentanoate Chemical compound N=1C=CNC=1C(C)(C(=O)OCC)C(CC)C1=CC=CC=C1 SLRLUHKUYPGESO-UHFFFAOYSA-N 0.000 description 1
- JMZZTLWBBMADOK-UHFFFAOYSA-N ethyl 2-(1h-imidazol-2-yl)-3-methyl-2-phenylbutanoate Chemical compound C=1C=CC=CC=1C(C(C)C)(C(=O)OCC)C1=NC=CN1 JMZZTLWBBMADOK-UHFFFAOYSA-N 0.000 description 1
- MCGGQYKHZGQEGN-UHFFFAOYSA-N ethyl 2-(4-chlorophenyl)-2-(1h-imidazol-2-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC(Cl)=CC=1)(C(=O)OCC)C1=NC=CN1 MCGGQYKHZGQEGN-UHFFFAOYSA-N 0.000 description 1
- DRNQRIRVMLZTTF-UHFFFAOYSA-N ethyl 2-benzyl-2-(1h-imidazol-2-yl)-3-methylbutanoate Chemical compound N=1C=CNC=1C(C(=O)OCC)(C(C)C)CC1=CC=CC=C1 DRNQRIRVMLZTTF-UHFFFAOYSA-N 0.000 description 1
- MSBGLMWCKRSNHW-UHFFFAOYSA-N ethyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OCC)C1=CC=CC=C1 MSBGLMWCKRSNHW-UHFFFAOYSA-N 0.000 description 1
- PDWBYRLVGPMRGN-UHFFFAOYSA-N ethyl 2-chloro-2-(4-chlorophenyl)-2-phenylacetate Chemical compound C=1C=C(Cl)C=CC=1C(Cl)(C(=O)OCC)C1=CC=CC=C1 PDWBYRLVGPMRGN-UHFFFAOYSA-N 0.000 description 1
- XJCMYFYVAGRANC-UHFFFAOYSA-N ethyl 2-chloro-3-methyl-2-phenylbutanoate Chemical compound CCOC(=O)C(Cl)(C(C)C)C1=CC=CC=C1 XJCMYFYVAGRANC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- QKLCQKPAECHXCQ-UHFFFAOYSA-N ethyl phenylglyoxylate Chemical compound CCOC(=O)C(=O)C1=CC=CC=C1 QKLCQKPAECHXCQ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 1
- 229960002867 griseofulvin Drugs 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- WMHPZAWGENFCAS-UHFFFAOYSA-N methyl 2,2-bis(4-fluorophenyl)-2-(1h-imidazol-2-yl)acetate Chemical compound C=1C=C(F)C=CC=1C(C=1C=CC(F)=CC=1)(C(=O)OC)C1=NC=CN1 WMHPZAWGENFCAS-UHFFFAOYSA-N 0.000 description 1
- CLZGROCYYPFPAG-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-bis(4-methylphenyl)acetate Chemical compound C=1C=C(C)C=CC=1C(C=1C=CC(C)=CC=1)(C(=O)OC)C1=NC=CN1 CLZGROCYYPFPAG-UHFFFAOYSA-N 0.000 description 1
- KXAQWOCSDWVABF-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2-(2-methylphenyl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C(=CC=CC=1)C)(C(=O)OC)C1=NC=CN1 KXAQWOCSDWVABF-UHFFFAOYSA-N 0.000 description 1
- RBIZUCWGJMRQKS-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2-(4-methylphenyl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC(C)=CC=1)(C(=O)OC)C1=NC=CN1 RBIZUCWGJMRQKS-UHFFFAOYSA-N 0.000 description 1
- DKQFBMYNBRIZCA-UHFFFAOYSA-N methyl 2-(2-chlorophenyl)-2-(1h-imidazol-2-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C(=CC=CC=1)Cl)(C(=O)OC)C1=NC=CN1 DKQFBMYNBRIZCA-UHFFFAOYSA-N 0.000 description 1
- HZXFRXXRYDAVID-UHFFFAOYSA-N methyl 2-(2-methyl-1h-imidazol-5-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=CN=C(C)N1 HZXFRXXRYDAVID-UHFFFAOYSA-N 0.000 description 1
- FPFJKVGMDIAFJI-UHFFFAOYSA-N methyl 2-(4-chlorophenyl)-2-(1h-imidazol-2-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC(Cl)=CC=1)(C(=O)OC)C1=NC=CN1 FPFJKVGMDIAFJI-UHFFFAOYSA-N 0.000 description 1
- JTCSJNCBUJSRGQ-UHFFFAOYSA-N methyl 2-chloro-2-(2-methylphenyl)-2-phenylacetate Chemical compound C=1C=CC=C(C)C=1C(Cl)(C(=O)OC)C1=CC=CC=C1 JTCSJNCBUJSRGQ-UHFFFAOYSA-N 0.000 description 1
- ZFFYVOGDTWBQSG-UHFFFAOYSA-N methyl 2-chloro-2-(4-methylphenyl)-2-phenylacetate Chemical compound C=1C=C(C)C=CC=1C(Cl)(C(=O)OC)C1=CC=CC=C1 ZFFYVOGDTWBQSG-UHFFFAOYSA-N 0.000 description 1
- BTTBHWMYJRVGNA-UHFFFAOYSA-N methyl 2-chloro-3,3-dimethyl-2-phenylbutanoate Chemical compound COC(=O)C(Cl)(C(C)(C)C)C1=CC=CC=C1 BTTBHWMYJRVGNA-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- CJXUYNZKJHUHLE-UHFFFAOYSA-N octyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCCCCCCCC)C1=NC=CN1 CJXUYNZKJHUHLE-UHFFFAOYSA-N 0.000 description 1
- RYQZDZLSAGLCHR-UHFFFAOYSA-N octyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OCCCCCCCC)C1=CC=CC=C1 RYQZDZLSAGLCHR-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen 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
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- ZKSUJTQPJAGLCM-UHFFFAOYSA-N propyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OCCC)C1=CC=CC=C1 ZKSUJTQPJAGLCM-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 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
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691925994 DE1925994C3 (de) | 1969-05-21 | Phenyl-imidazolyl-fettsäurederivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128571B true NO128571B (pl) | 1973-12-10 |
Family
ID=5734834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO93170A NO128571B (pl) | 1969-05-21 | 1970-05-20 |
Country Status (7)
| Country | Link |
|---|---|
| ES (1) | ES379870A1 (pl) |
| IE (1) | IE34289B1 (pl) |
| IL (1) | IL34516A (pl) |
| NO (1) | NO128571B (pl) |
| PH (1) | PH12184A (pl) |
| PL (1) | PL80851B1 (pl) |
| RO (1) | RO56292A (pl) |
-
1970
- 1970-05-13 IL IL34516A patent/IL34516A/en unknown
- 1970-05-13 IE IE63070A patent/IE34289B1/xx unknown
- 1970-05-19 PH PH11460A patent/PH12184A/en unknown
- 1970-05-20 PL PL14074470A patent/PL80851B1/pl unknown
- 1970-05-20 RO RO6340570A patent/RO56292A/ro unknown
- 1970-05-20 NO NO93170A patent/NO128571B/no unknown
- 1970-05-21 ES ES379870A patent/ES379870A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| PH12184A (en) | 1978-11-21 |
| IL34516A0 (en) | 1970-07-19 |
| IE34289B1 (en) | 1975-04-02 |
| ES379870A1 (es) | 1972-09-16 |
| IL34516A (en) | 1973-01-30 |
| IE34289L (en) | 1970-11-21 |
| RO56292A (pl) | 1974-08-01 |
| PL80851B1 (pl) | 1975-08-30 |
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