DK141287B - Analogifremgangsmåde til fremstilling af 5-nitro-imidazolcarbamater eller syreadditionssalte deraf. - Google Patents
Analogifremgangsmåde til fremstilling af 5-nitro-imidazolcarbamater eller syreadditionssalte deraf. Download PDFInfo
- Publication number
- DK141287B DK141287B DK348866AA DK348866A DK141287B DK 141287 B DK141287 B DK 141287B DK 348866A A DK348866A A DK 348866AA DK 348866 A DK348866 A DK 348866A DK 141287 B DK141287 B DK 141287B
- Authority
- DK
- Denmark
- Prior art keywords
- methyl
- formula
- compound
- above meaning
- nitro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 239000002253 acid Substances 0.000 title claims description 15
- 150000003839 salts Chemical class 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 8
- GEPNZFMLBLNJDW-UHFFFAOYSA-N C(N)(O)=O.[N+](=O)([O-])C1=CN=CN1 Chemical class C(N)(O)=O.[N+](=O)([O-])C1=CN=CN1 GEPNZFMLBLNJDW-UHFFFAOYSA-N 0.000 title claims description 5
- -1 phenylsulfonyloxy Chemical group 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 21
- 229910052736 halogen Chemical group 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- JSAQDPJIVQMBAY-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)methanol Chemical compound CN1C(CO)=NC=C1[N+]([O-])=O JSAQDPJIVQMBAY-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical group NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002024 ethyl acetate extract Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- PNXWREBRHUDCJO-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)methyl thiocyanate Chemical compound CN1C(=NC=C1[N+](=O)[O-])CSC#N PNXWREBRHUDCJO-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 150000002540 isothiocyanates Chemical class 0.000 description 3
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical group CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- PQFRTXSWDXZRRS-UHFFFAOYSA-N ronidazole Chemical compound CN1C(COC(N)=O)=NC=C1[N+]([O-])=O PQFRTXSWDXZRRS-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XWIYNNJPQAWSGT-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)methylcarbamic acid Chemical compound CN1C(CNC(O)=O)=NC=C1[N+]([O-])=O XWIYNNJPQAWSGT-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- NTUBJABVOKHTGZ-UHFFFAOYSA-N CN1C([N+]([O-])=O)=CN=C1CC1=C(NC(O)=O)SC=C1 Chemical compound CN1C([N+]([O-])=O)=CN=C1CC1=C(NC(O)=O)SC=C1 NTUBJABVOKHTGZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 2
- 208000005448 Trichomonas Infections Diseases 0.000 description 2
- 206010044620 Trichomoniasis Diseases 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000002141 anti-parasite Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- IBXPYPUJPLLOIN-UHFFFAOYSA-N dimetridazole Chemical group CC1=NC=C(N(=O)=O)N1C IBXPYPUJPLLOIN-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 229940063190 flagyl Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- ZZKCXCKMFUXNMY-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)methyl N-methylcarbamate Chemical compound CNC(OCC=1N(C(=CN1)[N+](=O)[O-])C)=O ZZKCXCKMFUXNMY-UHFFFAOYSA-N 0.000 description 1
- KZVZTMLHLWGZKW-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)methyl carbonochloridate Chemical compound CN1C(COC(Cl)=O)=NC=C1[N+]([O-])=O KZVZTMLHLWGZKW-UHFFFAOYSA-N 0.000 description 1
- FXPSGWRMAKYTIA-UHFFFAOYSA-N (5-nitro-1H-imidazol-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1(=CC=C(C=C1)S(=O)(=O)OCC=1NC(=CN1)[N+](=O)[O-])C FXPSGWRMAKYTIA-UHFFFAOYSA-N 0.000 description 1
- PDISGXFXQFGQFB-UHFFFAOYSA-N 2-(chloromethyl)-1-methyl-5-nitroimidazole Chemical compound CN1C(CCl)=NC=C1[N+]([O-])=O PDISGXFXQFGQFB-UHFFFAOYSA-N 0.000 description 1
- GOKBPGXXQSCLLS-UHFFFAOYSA-N 2-bromo-5-methyl-4-nitro-1h-imidazole Chemical compound CC=1NC(Br)=NC=1[N+]([O-])=O GOKBPGXXQSCLLS-UHFFFAOYSA-N 0.000 description 1
- XOJFIXFDWAYHTE-UHFFFAOYSA-N 3,5-dimethyl-4-nitro-1h-imidazole-2-thione Chemical compound CC=1NC(=S)N(C)C=1[N+]([O-])=O XOJFIXFDWAYHTE-UHFFFAOYSA-N 0.000 description 1
- 150000004958 5-nitroimidazoles Chemical class 0.000 description 1
- 208000004881 Amebiasis Diseases 0.000 description 1
- 206010001980 Amoebiasis Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KLPTZEAFVDGAGU-UHFFFAOYSA-N CC(C1=C(NC(=N1)SC#N)[N+](=O)[O-])OC(=O)C Chemical compound CC(C1=C(NC(=N1)SC#N)[N+](=O)[O-])OC(=O)C KLPTZEAFVDGAGU-UHFFFAOYSA-N 0.000 description 1
- MZESOMNSCVOPAB-UHFFFAOYSA-N CNC(=S)OCC1=NC=C(N1C)[N+](=O)[O-] Chemical compound CNC(=S)OCC1=NC=C(N1C)[N+](=O)[O-] MZESOMNSCVOPAB-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000014085 Chronic respiratory disease Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229940126062 Compound A Drugs 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
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000224526 Trichomonas Species 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- 239000003096 antiparasitic agent Substances 0.000 description 1
- 229940125687 antiparasitic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- KDJVUTSOHYQCDQ-UHFFFAOYSA-N carbamic acid;1h-imidazole Chemical class NC([O-])=O.[NH2+]1C=CN=C1 KDJVUTSOHYQCDQ-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002038 ethyl acetate fraction Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 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
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 201000002311 trypanosomiasis Diseases 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
Classifications
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Devices For Checking Fares Or Tickets At Control Points (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47023965A | 1965-07-07 | 1965-07-07 | |
| US47023965 | 1965-07-07 | ||
| US55093266A | 1966-05-18 | 1966-05-18 | |
| US55093266 | 1966-05-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141287B true DK141287B (da) | 1980-02-18 |
| DK141287C DK141287C (enrdf_load_stackoverflow) | 1980-07-07 |
Family
ID=27043018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK348866AA DK141287B (da) | 1965-07-07 | 1966-07-06 | Analogifremgangsmåde til fremstilling af 5-nitro-imidazolcarbamater eller syreadditionssalte deraf. |
Country Status (18)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1280355A (en) * | 1969-06-20 | 1972-07-05 | Rech S Et D Applic Scient Et M | Substituted 5-nitro-imidazoles and their preparation |
| BE758145A (fr) * | 1969-10-29 | 1971-04-28 | Smith Kline French Lab | Iso-thio-urees et derives |
| US3678066A (en) * | 1970-03-06 | 1972-07-18 | Squibb & Sons Inc | Thiocyanic acid esters |
| US3968228A (en) * | 1973-11-13 | 1976-07-06 | Merck & Co., Inc. | 4-Nitro-5-cyanoimidazoles as coccidiostats |
| JPH02254965A (ja) * | 1989-03-28 | 1990-10-15 | Chiyoudendou Hatsuden Kanren Kiki Zairyo Gijutsu Kenkyu Kumiai | 超電導回転電機の回転子 |
| JP2018516237A (ja) | 2015-04-02 | 2018-06-21 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 新規な５−置換イミダゾール誘導体 |
| BR112019006445A2 (pt) | 2016-09-29 | 2019-10-01 | Bayer Ag | novos derivados de 5-imidazolilmetil substituídos |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5149436B2 (enrdf_load_stackoverflow) * | 1971-11-15 | 1976-12-27 |
-
1966
- 1966-06-08 IL IL25931A patent/IL25931A/en unknown
- 1966-07-04 GB GB29846/66A patent/GB1153347A/en not_active Expired
- 1966-07-04 GB GB35039/68A patent/GB1155529A/en not_active Expired
- 1966-07-04 GB GB35033/68A patent/GB1154290A/en not_active Expired
- 1966-07-04 GB GB38884/68A patent/GB1155530A/en not_active Expired
- 1966-07-04 GB GB32952/68A patent/GB1155528A/en not_active Expired
- 1966-07-05 AT AT559269A patent/AT291989B/de not_active IP Right Cessation
- 1966-07-05 AT AT545669A patent/AT294487B/de not_active IP Right Cessation
- 1966-07-05 AT AT559369A patent/AT291990B/de not_active IP Right Cessation
- 1966-07-05 AT AT551669A patent/AT291988B/de not_active IP Right Cessation
- 1966-07-05 AT AT643566A patent/AT284114B/de not_active IP Right Cessation
- 1966-07-05 IT IT6615338A patent/IT1061026B/it active
- 1966-07-05 ES ES0329085A patent/ES329085A1/es not_active Expired
- 1966-07-06 BR BR181050/66A patent/BR6681050D0/pt unknown
- 1966-07-06 NO NO163800A patent/NO122186B/no unknown
- 1966-07-06 DK DK348866AA patent/DK141287B/da unknown
- 1966-07-06 FI FI661807A patent/FI46961C/fi active
- 1966-07-06 FR FR68482A patent/FR1502699A/fr not_active Expired
- 1966-07-06 SE SE9274/66A patent/SE343578B/xx unknown
- 1966-07-06 DE DE1966M0070135 patent/DE1620018B2/de active Granted
- 1966-07-07 CH CH988566A patent/CH562806A5/xx not_active IP Right Cessation
- 1966-07-07 CH CH991771A patent/CH565769A5/xx not_active IP Right Cessation
- 1966-07-07 BE BE683796D patent/BE683796A/xx not_active IP Right Cessation
- 1966-07-07 NL NL666609552A patent/NL149793B/xx not_active IP Right Cessation
- 1966-07-07 CH CH988566A patent/CH522651A/de not_active IP Right Cessation
- 1966-07-07 JP JP41043868A patent/JPS5010865B1/ja active Pending
- 1966-10-05 FR FR78932A patent/FR5890M/fr not_active Expired
-
1970
- 1970-11-09 JP JP45097971A patent/JPS4843909B1/ja active Pending
- 1970-11-09 CY CY56570A patent/CY565A/xx unknown
- 1970-11-27 IL IL35748A patent/IL35748A0/xx unknown
-
1971
- 1971-12-31 MY MY197155A patent/MY7100055A/xx unknown
-
1974
- 1974-11-29 JP JP49136394A patent/JPS5138718B1/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1574019A (en) | Therapeutically useful 3,4,5-trimethoxybenzene derivatives | |
| US3062827A (en) | 5-(3', 5'-dialkylphenoxymethyl)-2-oxazolidones | |
| FI59991B (fi) | Foerfarande foer framstaellning av 2-arylamino-2-imidazolin-derivat och deras salter | |
| DK141287B (da) | Analogifremgangsmåde til fremstilling af 5-nitro-imidazolcarbamater eller syreadditionssalte deraf. | |
| SU557758A3 (ru) | Способ получени 4-азабензимидазолов или их солей | |
| US3790592A (en) | 1-substituted-5-nitroimidazol-2-ylalkyl-(n-substituted)-carbamates | |
| SU1091852A3 (ru) | Способ получени производных 2-аминометил-4,6-дигалоидфенола или их солей | |
| SU950188A3 (ru) | Способ получени производных 4(5)-меркаптометилимидазолов | |
| US4268511A (en) | 3-Amino(1H,3H)quinazoline-2,4-dione derivatives and their therapeutic applications | |
| US4159380A (en) | Imidazolylethoxy derivatives of pyrazolo[3,4-b]pyridine-5-methanols | |
| US3398155A (en) | 2, 6-dichloro-isonicotinamide derivatives and a method for their preparation | |
| SU1227111A3 (ru) | Способ получени производных гуанидина или их таутомерных соединений или их солей | |
| US3773781A (en) | 1-substituted-5-nitroimidazol-2-ylalkyl-(n-substituted)-carbamates | |
| US3184460A (en) | 1-(alkoxyphenylalkyl)-2-imidazolinones, -2-imidazolidinones and -2-pyrimidinones | |
| NO119593B (enrdf_load_stackoverflow) | ||
| US2865925A (en) | Process for preparing n-(2-hydroxyethyl)-n-(lower-alkyl)-9-aminomethylanthracenes and intermediates therein | |
| US3334115A (en) | Basically substituted ureas and salts thereof | |
| US5395945A (en) | Synthesis of 3,3-dinitroazetidine | |
| US3461131A (en) | Process for preparing 2-substituted cycloheptimidazole derivatives | |
| SE441923B (sv) | 1-acyl-2-imidazolin till anvendning som mellanprodukt vid framstellning av 1-osubstituerad-2-imidazolin samt forfarande for dess framstellning | |
| US3860586A (en) | Derivatives of 4-(2-aminophenyl)-3-thioallophanic acid | |
| US3803165A (en) | N-(2-(2-nitro-1-imidazolyl)ethyl)-2',2',2'-trichloroethyl carbamate | |
| US3184452A (en) | New aminoalkoxy compounds and process for theik manufacture | |
| US3654299A (en) | Nitroimidazolyl antimicrobial agents | |
| US3761491A (en) | 1-substituted-5-nitroimidazol-2-ylalkyl-(n-substituted)-carbamates |