NO752577L - - Google Patents
Info
- Publication number
- NO752577L NO752577L NO752577A NO752577A NO752577L NO 752577 L NO752577 L NO 752577L NO 752577 A NO752577 A NO 752577A NO 752577 A NO752577 A NO 752577A NO 752577 L NO752577 L NO 752577L
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- carbon atoms
- oxadiazol
- alkyl
- substituted
- Prior art date
Links
- -1 N-methylpyrryl Chemical group 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- JQGZIZMUKZVIJX-UHFFFAOYSA-N I[N] Chemical compound I[N] JQGZIZMUKZVIJX-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000507 anthelmentic effect Effects 0.000 description 6
- SRNSBDNIAKCXGI-UHFFFAOYSA-N n'-hydroxy-4-nitrobenzenecarboximidamide Chemical compound ON=C(N)C1=CC=C([N+]([O-])=O)C=C1 SRNSBDNIAKCXGI-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- KGUZRMOXECFUGA-UHFFFAOYSA-N 4-(1,2,4-oxadiazol-3-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=NOC=N1 KGUZRMOXECFUGA-UHFFFAOYSA-N 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 208000031888 Mycoses Diseases 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000000921 anthelmintic agent Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YPBQULUMQROUSN-UHFFFAOYSA-N 3-(4-nitrophenyl)-5-phenyl-1,2,4-oxadiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NOC(C=2C=CC=CC=2)=N1 YPBQULUMQROUSN-UHFFFAOYSA-N 0.000 description 3
- PYIMPFSWJKTGJQ-UHFFFAOYSA-N 3-(4-nitrophenyl)-5-pyridin-2-yl-1,2,4-oxadiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NOC(C=2N=CC=CC=2)=N1 PYIMPFSWJKTGJQ-UHFFFAOYSA-N 0.000 description 3
- XPTIIOBBBMJBKM-UHFFFAOYSA-N 4-(5-phenyl-1,2,4-oxadiazol-3-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=NOC(C=2C=CC=CC=2)=N1 XPTIIOBBBMJBKM-UHFFFAOYSA-N 0.000 description 3
- DCQBJSZPYNKQBT-UHFFFAOYSA-N 4-(5-pyridin-2-yl-1,2,4-oxadiazol-3-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=NOC(C=2N=CC=CC=2)=N1 DCQBJSZPYNKQBT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 229940124339 anthelmintic agent Drugs 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical class SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- ISVMGWXEUNXBBK-UHFFFAOYSA-N methyl n-[4-(1,2,4-oxadiazol-3-yl)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C1=NOC=N1 ISVMGWXEUNXBBK-UHFFFAOYSA-N 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- 239000013589 supplement Substances 0.000 description 3
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 2
- KWOHXJCKLMGBFD-UHFFFAOYSA-N 3-(4-nitrophenyl)-1,2,4-oxadiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NOC=N1 KWOHXJCKLMGBFD-UHFFFAOYSA-N 0.000 description 2
- NKJIFDNZPGLLSH-UHFFFAOYSA-N 4-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C=C1 NKJIFDNZPGLLSH-UHFFFAOYSA-N 0.000 description 2
- NGKANUCFHANCOY-UHFFFAOYSA-N 4-phenyloxadiazol-5-amine Chemical compound O1N=NC(C=2C=CC=CC=2)=C1N NGKANUCFHANCOY-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical class ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 description 2
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000004615 ingredient 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- IWBVVKMRLNSDNC-UHFFFAOYSA-N (2,5-dichlorophenyl) carbonochloridate Chemical compound ClC(=O)OC1=CC(Cl)=CC=C1Cl IWBVVKMRLNSDNC-UHFFFAOYSA-N 0.000 description 1
- MSBGPEACXKBQSX-UHFFFAOYSA-N (4-fluorophenyl) carbonochloridate Chemical compound FC1=CC=C(OC(Cl)=O)C=C1 MSBGPEACXKBQSX-UHFFFAOYSA-N 0.000 description 1
- XOFZPIYYMJUNRG-UHFFFAOYSA-N (4-methylphenyl) carbonochloridate Chemical compound CC1=CC=C(OC(Cl)=O)C=C1 XOFZPIYYMJUNRG-UHFFFAOYSA-N 0.000 description 1
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
- FTECMELMYALUQZ-UHFFFAOYSA-N 1,3-thiazole-4-carbonyl chloride Chemical compound ClC(=O)C1=CSC=N1 FTECMELMYALUQZ-UHFFFAOYSA-N 0.000 description 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- JOYDZQJINHJNPM-UHFFFAOYSA-N 1-methylpyrrole-2-carbonyl chloride Chemical compound CN1C=CC=C1C(Cl)=O JOYDZQJINHJNPM-UHFFFAOYSA-N 0.000 description 1
- XYKIRLSGVFMELA-UHFFFAOYSA-N 1-methylpyrrole-3-carbonyl chloride Chemical compound CN1C=CC(C(Cl)=O)=C1 XYKIRLSGVFMELA-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
- NZCKTGCKFJDGFD-UHFFFAOYSA-N 2-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Br NZCKTGCKFJDGFD-UHFFFAOYSA-N 0.000 description 1
- AGZYMTWFJLEBIJ-UHFFFAOYSA-N 2-chloro-3-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=CC(C#N)=C1Cl AGZYMTWFJLEBIJ-UHFFFAOYSA-N 0.000 description 1
- HNKYOWFREPLBBR-UHFFFAOYSA-N 2-chloro-n'-hydroxy-3-nitrobenzenecarboximidamide Chemical compound ON=C(N)C1=CC=CC([N+]([O-])=O)=C1Cl HNKYOWFREPLBBR-UHFFFAOYSA-N 0.000 description 1
- RWXNPKHTHFLAAN-UHFFFAOYSA-N 2-ethoxy-4-nitrobenzonitrile Chemical compound CCOC1=CC([N+]([O-])=O)=CC=C1C#N RWXNPKHTHFLAAN-UHFFFAOYSA-N 0.000 description 1
- QJBKLDKRNSWRQI-UHFFFAOYSA-N 2-ethoxy-n'-hydroxy-4-nitrobenzenecarboximidamide Chemical compound CCOC1=CC([N+]([O-])=O)=CC=C1C(N)=NO QJBKLDKRNSWRQI-UHFFFAOYSA-N 0.000 description 1
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- KKNACFPZDAAOLL-UHFFFAOYSA-N 2-nitro-4-phenoxybenzonitrile Chemical compound C1=C(C#N)C([N+](=O)[O-])=CC(OC=2C=CC=CC=2)=C1 KKNACFPZDAAOLL-UHFFFAOYSA-N 0.000 description 1
- UIHQCBLHBPUMPN-UHFFFAOYSA-N 2-nitro-4-phenylbenzonitrile Chemical compound C1=C(C#N)C([N+](=O)[O-])=CC(C=2C=CC=CC=2)=C1 UIHQCBLHBPUMPN-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- MIDHYAOVUFWYPU-UHFFFAOYSA-N 3-methyl-2-nitrobenzonitrile Chemical compound CC1=CC=CC(C#N)=C1[N+]([O-])=O MIDHYAOVUFWYPU-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WLBZNBJVMSNGQC-UHFFFAOYSA-N 4-(dimethylamino)-2-nitrobenzonitrile Chemical compound CN(C)C1=CC=C(C#N)C([N+]([O-])=O)=C1 WLBZNBJVMSNGQC-UHFFFAOYSA-N 0.000 description 1
- UIGVODRSVNCNRA-UHFFFAOYSA-N 4-(dimethylamino)-n'-hydroxy-2-nitrobenzenecarboximidamide Chemical compound CN(C)C1=CC=C(C(N)=NO)C([N+]([O-])=O)=C1 UIGVODRSVNCNRA-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- AVSDRULQBQMLES-UHFFFAOYSA-N 4-nitro-3-(trifluoromethyl)benzonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C=C1C(F)(F)F AVSDRULQBQMLES-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
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- WYCHDDNJOHQHTG-UHFFFAOYSA-N [4-(1,2,4-oxadiazol-3-yl)phenyl]carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1C1=NOC=N1 WYCHDDNJOHQHTG-UHFFFAOYSA-N 0.000 description 1
- FDBCFYYYFYTMBA-UHFFFAOYSA-N [4-[5-(4-chlorophenyl)-1,2,4-oxadiazol-3-yl]phenyl]carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1C1=NOC(C=2C=CC(Cl)=CC=2)=N1 FDBCFYYYFYTMBA-UHFFFAOYSA-N 0.000 description 1
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- 235000019253 formic acid Nutrition 0.000 description 1
- BTUIFMCWPFMNRG-UHFFFAOYSA-N furan-3-carbonyl chloride Chemical compound ClC(=O)C=1C=COC=1 BTUIFMCWPFMNRG-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
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- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
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- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- FTNDUMGMMCBRIT-UHFFFAOYSA-N n'-hydroxy-2-nitro-4-phenylbenzenecarboximidamide Chemical compound C1=C([N+]([O-])=O)C(C(=NO)N)=CC=C1C1=CC=CC=C1 FTNDUMGMMCBRIT-UHFFFAOYSA-N 0.000 description 1
- YVBOSDURRVSSDD-UHFFFAOYSA-N n'-hydroxy-3-methyl-2-nitrobenzenecarboximidamide Chemical compound CC1=CC=CC(C(N)=NO)=C1[N+]([O-])=O YVBOSDURRVSSDD-UHFFFAOYSA-N 0.000 description 1
- DOZLUDXBGNKHGZ-UHFFFAOYSA-N n'-hydroxy-4-nitro-3-(trifluoromethyl)benzenecarboximidamide Chemical compound ON=C(N)C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 DOZLUDXBGNKHGZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JIBAEWYZMHBYND-UHFFFAOYSA-N o-(2,2,2-trichloroethyl) chloromethanethioate Chemical compound ClC(=S)OCC(Cl)(Cl)Cl JIBAEWYZMHBYND-UHFFFAOYSA-N 0.000 description 1
- HZBXSUFBKXPOAF-UHFFFAOYSA-N o-(4-fluorophenyl) chloromethanethioate Chemical compound FC1=CC=C(OC(Cl)=S)C=C1 HZBXSUFBKXPOAF-UHFFFAOYSA-N 0.000 description 1
- PIAWCPAIZSGTRF-UHFFFAOYSA-N o-(4-methoxyphenyl) chloromethanethioate Chemical compound COC1=CC=C(OC(Cl)=S)C=C1 PIAWCPAIZSGTRF-UHFFFAOYSA-N 0.000 description 1
- HIABEUXOMWGKMC-UHFFFAOYSA-N o-(trifluoromethyl) chloromethanethioate Chemical compound FC(F)(F)OC(Cl)=S HIABEUXOMWGKMC-UHFFFAOYSA-N 0.000 description 1
- UFFYFCIOYMVMDY-UHFFFAOYSA-N o-cyclohexyl chloromethanethioate Chemical compound ClC(=S)OC1CCCCC1 UFFYFCIOYMVMDY-UHFFFAOYSA-N 0.000 description 1
- QQZYYVYHCWSFGK-UHFFFAOYSA-N o-cyclopropyl chloromethanethioate Chemical compound ClC(=S)OC1CC1 QQZYYVYHCWSFGK-UHFFFAOYSA-N 0.000 description 1
- VIVFSUFXLASWTD-UHFFFAOYSA-N o-prop-2-ynyl chloromethanethioate Chemical compound ClC(=S)OCC#C VIVFSUFXLASWTD-UHFFFAOYSA-N 0.000 description 1
- ZRRMJORTCRWSGZ-UHFFFAOYSA-N o-propan-2-yl chloromethanethioate Chemical compound CC(C)OC(Cl)=S ZRRMJORTCRWSGZ-UHFFFAOYSA-N 0.000 description 1
- MEFGPLCNJIQRHY-UHFFFAOYSA-N o-tert-butyl chloromethanethioate Chemical compound CC(C)(C)OC(Cl)=S MEFGPLCNJIQRHY-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 235000020323 palazzo Nutrition 0.000 description 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- JZCQEFSLNPNYMO-UHFFFAOYSA-N phenyl n-[4-(1,2,4-oxadiazol-3-yl)phenyl]carbamate Chemical compound C=1C=CC=CC=1OC(=O)NC(C=C1)=CC=C1C=1N=CON=1 JZCQEFSLNPNYMO-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
- RAMTXCRMKBFPRG-UHFFFAOYSA-N prop-2-ynyl carbonochloridate Chemical compound ClC(=O)OCC#C RAMTXCRMKBFPRG-UHFFFAOYSA-N 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PSAYJRPASWETSH-UHFFFAOYSA-N pyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CC=N1 PSAYJRPASWETSH-UHFFFAOYSA-N 0.000 description 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- HBEFYGYBMKPNSZ-UHFFFAOYSA-N s-phenyl chloromethanethioate Chemical compound ClC(=O)SC1=CC=CC=C1 HBEFYGYBMKPNSZ-UHFFFAOYSA-N 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- LMIRGQMBYXMZGJ-UHFFFAOYSA-N trifluoromethyl carbonochloridate Chemical compound FC(F)(F)OC(Cl)=O LMIRGQMBYXMZGJ-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49064374A | 1974-07-22 | 1974-07-22 | |
| US05/566,595 US4003909A (en) | 1974-07-22 | 1975-04-09 | [(1,2,4-Oxadiazol-3-yl)phenyl]carbamic or thiocarbamic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO752577L true NO752577L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-01-23 |
Family
ID=27050123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO752577A NO752577L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-07-22 | 1975-07-21 |
Country Status (7)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES456483A0 (es) * | 1976-03-09 | 1978-02-16 | Hoechst Ag | Procedimiento para la preparacion de compuestos de estilbeno. |
| DE2801509A1 (de) * | 1978-01-12 | 1979-07-19 | Schering Ag | 1,2,4-oxadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
| US4871753A (en) * | 1986-12-12 | 1989-10-03 | Ciba-Geigy Corporation | 3-Phenyl-5-trifluoromethyl-1,2,4-oxadiazole compounds which are useful pesticides |
| DE19643037A1 (de) * | 1996-10-18 | 1998-04-23 | Boehringer Ingelheim Kg | Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| EP1582519A3 (en) * | 1999-08-19 | 2005-12-21 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| CA2381975A1 (en) * | 1999-08-19 | 2001-02-22 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| US6660753B2 (en) * | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| AU2001231202A1 (en) * | 2000-01-28 | 2001-08-07 | Akkadix Corporation | Methods for killing nematodes and nematode eggs using 4-phenoxy-6-aminopyrimidine derivatives |
| US20030181488A1 (en) | 2002-03-07 | 2003-09-25 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Administration form for the oral application of 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionic acid ethyl ester and the salts thereof |
| US20060189661A1 (en) * | 2003-11-03 | 2006-08-24 | Wagenen Bradford V | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| JP4587202B2 (ja) * | 2004-05-27 | 2010-11-24 | 田岡化学工業株式会社 | フェニルオキサジアゾール類の製造法 |
| CA2672616A1 (en) * | 2006-12-15 | 2008-06-26 | Abbott Laboratories | Novel oxadiazole compounds |
| US20110207704A1 (en) * | 2006-12-15 | 2011-08-25 | Abbott Laboratories | Novel Oxadiazole Compounds |
| CN108484522A (zh) * | 2018-04-25 | 2018-09-04 | 山东百诺医药股份有限公司 | 4-(1,2,4-噁二唑-3-基)苯胺的制备方法 |
| CN114478428A (zh) * | 2022-01-26 | 2022-05-13 | 西安医学院 | 1,2,4-噁唑类化合物及其制备方法和应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3270028A (en) * | 1963-05-08 | 1966-08-30 | Acraf | Certain 3-aryl-1, 2, 4-oxadiazoles |
-
1975
- 1975-04-09 US US05/566,595 patent/US4003909A/en not_active Expired - Lifetime
- 1975-05-29 AU AU81676/75A patent/AU8167675A/en not_active Expired
- 1975-07-03 NL NL7507927A patent/NL7507927A/xx unknown
- 1975-07-21 NO NO752577A patent/NO752577L/no unknown
- 1975-07-22 DE DE19752532742 patent/DE2532742A1/de active Pending
- 1975-07-22 SE SE7508345A patent/SE7508345L/xx unknown
- 1975-07-22 JP JP50090022A patent/JPS51105067A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7507927A (nl) | 1976-01-26 |
| US4003909A (en) | 1977-01-18 |
| AU8167675A (en) | 1976-12-02 |
| JPS51105067A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-17 |
| DE2532742A1 (de) | 1976-02-12 |
| SE7508345L (sv) | 1976-01-23 |
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