NO792696L - Monokarboksylater av fenylguanidinsyre-estere samt fremgangsmaate til deres fremstilling - Google Patents
Monokarboksylater av fenylguanidinsyre-estere samt fremgangsmaate til deres fremstillingInfo
- Publication number
- NO792696L NO792696L NO792696A NO792696A NO792696L NO 792696 L NO792696 L NO 792696L NO 792696 A NO792696 A NO 792696A NO 792696 A NO792696 A NO 792696A NO 792696 L NO792696 L NO 792696L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- methoxycarbonyl
- phenyl
- guanidine
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 239000002253 acid Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 6
- -1 phenylguanidine sulfonic acid esters Chemical class 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 244000000013 helminth Species 0.000 claims description 3
- 150000002541 isothioureas Chemical class 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- RMAHPRNLQIRHIJ-UHFFFAOYSA-N methyl carbamimidate Chemical class COC(N)=N RMAHPRNLQIRHIJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- 241000545744 Hirudinea Species 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 210000004185 liver Anatomy 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 241000244206 Nematoda Species 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 241000283086 Equidae Species 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000000507 anthelmentic effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- PEOUQUKUHBWKGO-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl] 4-amino-3-nitrobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1S(=O)(=O)OC1=CC=CC(C(F)(F)F)=C1 PEOUQUKUHBWKGO-UHFFFAOYSA-N 0.000 description 2
- DOCSUTOJBMLNFH-UHFFFAOYSA-N [3-[(n-methoxycarbonyl-n'-methylcarbamimidoyl)amino]-4-(propanoylamino)phenyl] benzenesulfonate Chemical compound C1=C(NC(NC(=O)OC)=NC)C(NC(=O)CC)=CC=C1OS(=O)(=O)C1=CC=CC=C1 DOCSUTOJBMLNFH-UHFFFAOYSA-N 0.000 description 2
- MNRWLAGBOWNDOE-UHFFFAOYSA-N [3-[2-(2-methoxyacetyl)hydrazinyl]phenyl] benzenesulfonate Chemical compound COCC(=O)NNC1=CC=CC(OS(=O)(=O)C=2C=CC=CC=2)=C1 MNRWLAGBOWNDOE-UHFFFAOYSA-N 0.000 description 2
- QSHNOLMLGJKXGB-UHFFFAOYSA-N [4-formamido-3-[(n-methoxycarbonyl-n'-methylcarbamimidoyl)amino]phenyl] benzenesulfonate Chemical compound C1=C(NC=O)C(NC(NC(=O)OC)=NC)=CC(OS(=O)(=O)C=2C=CC=CC=2)=C1 QSHNOLMLGJKXGB-UHFFFAOYSA-N 0.000 description 2
- RHDZSFLIWVFNOW-UHFFFAOYSA-N [carbamoyl(methyl)amino] methyl carbonate Chemical compound C(=O)(OC)ON(C(O)=N)C RHDZSFLIWVFNOW-UHFFFAOYSA-N 0.000 description 2
- 229960001413 acetanilide Drugs 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- MMBDAJMDNVQFDV-UHFFFAOYSA-N methyl n-[amino(methylsulfanyl)methylidene]carbamate Chemical compound COC(=O)N=C(N)SC MMBDAJMDNVQFDV-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- QGRNOSUTWZYDTP-UHFFFAOYSA-N (2-chlorophenyl) 4-acetamido-3-[(n'-methoxycarbonylcarbamimidoyl)amino]benzenesulfonate Chemical compound C1=C(NC(C)=O)C(NC(=N)NC(=O)OC)=CC(S(=O)(=O)OC=2C(=CC=CC=2)Cl)=C1 QGRNOSUTWZYDTP-UHFFFAOYSA-N 0.000 description 1
- OQLVOYMTVSGURZ-UHFFFAOYSA-N (3-chlorophenyl) 4-acetamido-3-[(n'-methoxycarbonylcarbamimidoyl)amino]benzenesulfonate Chemical compound C1=C(NC(C)=O)C(NC(=N)NC(=O)OC)=CC(S(=O)(=O)OC=2C=C(Cl)C=CC=2)=C1 OQLVOYMTVSGURZ-UHFFFAOYSA-N 0.000 description 1
- ZVYDMTNZGWUXFR-UHFFFAOYSA-N (3-ethoxyphenyl) 3-[[amino-(methoxycarbonylamino)methylidene]amino]-4-[(2-methoxyacetyl)amino]benzenesulfonate Chemical compound CCOC1=CC=CC(OS(=O)(=O)C=2C=C(N\C(N)=N\C(=O)OC)C(NC(=O)COC)=CC=2)=C1 ZVYDMTNZGWUXFR-UHFFFAOYSA-N 0.000 description 1
- BCKMKZCGVQENKO-UHFFFAOYSA-N (4-cyanophenyl) 4-[(2-methoxyacetyl)amino]-3-[[(e)-n'-methoxycarbonylcarbamimidoyl]amino]benzenesulfonate Chemical compound C1=C(N\C(N)=N/C(=O)OC)C(NC(=O)COC)=CC=C1S(=O)(=O)OC1=CC=C(C#N)C=C1 BCKMKZCGVQENKO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KWCPQPFOPUCWPH-UHFFFAOYSA-N 1-(oxomethylidene)guanidine Chemical compound NC(=N)N=C=O KWCPQPFOPUCWPH-UHFFFAOYSA-N 0.000 description 1
- GEGLCBTXYBXOJA-UHFFFAOYSA-N 1-methoxyethanol Chemical compound COC(C)O GEGLCBTXYBXOJA-UHFFFAOYSA-N 0.000 description 1
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 description 1
- BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical class NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 description 1
- SADHVOSOZBAAGL-UHFFFAOYSA-N 3-(trifluoromethoxy)aniline Chemical compound NC1=CC=CC(OC(F)(F)F)=C1 SADHVOSOZBAAGL-UHFFFAOYSA-N 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
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000893172 Chabertia Species 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 241000920462 Heterakis Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- YRWLZFXJFBZBEY-UHFFFAOYSA-N N-(6-butyl-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCCC1=CC=C2N=C(NC(=O)OC)NC2=C1 YRWLZFXJFBZBEY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000510960 Oesophagostomum Species 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000244174 Strongyloides Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- TWELYPUFCLUBML-UHFFFAOYSA-N [3-(2-methylpropoxy)phenyl] 4-[(2-methoxyacetyl)amino]-3-[[(e)-n'-methoxycarbonylcarbamimidoyl]amino]benzenesulfonate Chemical compound C1=C(N\C(N)=N/C(=O)OC)C(NC(=O)COC)=CC=C1S(=O)(=O)OC1=CC=CC(OCC(C)C)=C1 TWELYPUFCLUBML-UHFFFAOYSA-N 0.000 description 1
- AUNRIVCUEICHNU-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl] 4-(butanoylamino)-3-[[(e)-n'-methoxycarbonylcarbamimidoyl]amino]benzenesulfonate Chemical compound C1=C(N\C(N)=N/C(=O)OC)C(NC(=O)CCC)=CC=C1S(=O)(=O)OC1=CC=CC(C(F)(F)F)=C1 AUNRIVCUEICHNU-UHFFFAOYSA-N 0.000 description 1
- QRLSALSSWXAEJB-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl] 4-[(2-methoxyacetyl)amino]-3-[[(e)-n'-methoxycarbonylcarbamimidoyl]amino]benzenesulfonate Chemical compound C1=C(N\C(N)=N/C(=O)OC)C(NC(=O)COC)=CC=C1S(=O)(=O)OC1=CC=CC(C(F)(F)F)=C1 QRLSALSSWXAEJB-UHFFFAOYSA-N 0.000 description 1
- LJNJJEMEHCBZQQ-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl] 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)OC=2C=C(C=CC=2)C(F)(F)F)=C1 LJNJJEMEHCBZQQ-UHFFFAOYSA-N 0.000 description 1
- GWBSILSTUTUSGM-UHFFFAOYSA-N [3-[(N'-ethyl-N-methoxycarbonylcarbamimidoyl)amino]-4-[(2-methoxyacetyl)amino]phenyl] benzenesulfonate Chemical compound C1=C(NC(=O)COC)C(NC(NC(=O)OC)=NCC)=CC(OS(=O)(=O)C=2C=CC=CC=2)=C1 GWBSILSTUTUSGM-UHFFFAOYSA-N 0.000 description 1
- UPTWTJUIAGWTBP-UHFFFAOYSA-N [3-[(n'-benzyl-n-methoxycarbonylcarbamimidoyl)amino]-4-[(2-methoxyacetyl)amino]phenyl] benzenesulfonate Chemical compound C1=C(NC(NC(=O)OC)=NCC=2C=CC=CC=2)C(NC(=O)COC)=CC=C1OS(=O)(=O)C1=CC=CC=C1 UPTWTJUIAGWTBP-UHFFFAOYSA-N 0.000 description 1
- DYALAEHIWFZFKL-UHFFFAOYSA-N [3-[[(e)-n'-methoxycarbonylcarbamimidoyl]amino]-4-(pentanoylamino)phenyl] benzenesulfonate Chemical compound C1=C(NC(=N)NC(=O)OC)C(NC(=O)CCCC)=CC=C1OS(=O)(=O)C1=CC=CC=C1 DYALAEHIWFZFKL-UHFFFAOYSA-N 0.000 description 1
- QMUPLEHOHBUTHM-UHFFFAOYSA-N [3-[bis(methoxycarbonylamino)methylideneamino]-4-[(2-methoxyacetyl)amino]phenyl] benzenesulfonate Chemical compound C1=C(N\C(NC(=O)OC)=N\C(=O)OC)C(NC(=O)COC)=CC=C1OS(=O)(=O)C1=CC=CC=C1 QMUPLEHOHBUTHM-UHFFFAOYSA-N 0.000 description 1
- FOLKNFXXHSKYJY-UHFFFAOYSA-N [4-(butanoylamino)-3-[(n-methoxycarbonyl-n'-methylcarbamimidoyl)amino]phenyl] benzenesulfonate Chemical compound C1=C(NC(NC(=O)OC)=NC)C(NC(=O)CCC)=CC=C1OS(=O)(=O)C1=CC=CC=C1 FOLKNFXXHSKYJY-UHFFFAOYSA-N 0.000 description 1
- IDFGSVLIZIXOET-UHFFFAOYSA-N [4-(butanoylamino)-3-[[(e)-n'-methoxycarbonylcarbamimidoyl]amino]phenyl] benzenesulfonate Chemical compound C1=C(NC(=N)NC(=O)OC)C(NC(=O)CCC)=CC=C1OS(=O)(=O)C1=CC=CC=C1 IDFGSVLIZIXOET-UHFFFAOYSA-N 0.000 description 1
- ABSAIOOLAAECTK-UHFFFAOYSA-N [4-(hexanoylamino)-3-[[(e)-n'-methoxycarbonylcarbamimidoyl]amino]phenyl] benzenesulfonate Chemical compound C1=C(NC(=N)NC(=O)OC)C(NC(=O)CCCCC)=CC=C1OS(=O)(=O)C1=CC=CC=C1 ABSAIOOLAAECTK-UHFFFAOYSA-N 0.000 description 1
- YUYMYANYNVLLBW-UHFFFAOYSA-N [4-[(2-methoxyacetyl)amino]-3-[(n'-methoxycarbonylcarbamimidoyl)amino]phenyl] benzenesulfonate Chemical compound C1=C(N\C(N)=N/C(=O)OC)C(NC(=O)COC)=CC=C1OS(=O)(=O)C1=CC=CC=C1 YUYMYANYNVLLBW-UHFFFAOYSA-N 0.000 description 1
- LSAQGPKXLWRUGT-UHFFFAOYSA-N [4-[(2-methoxyacetyl)amino]-3-[[(e)-n'-methoxycarbonylcarbamimidoyl]amino]phenyl] 3-(2-methylpropoxy)benzenesulfonate Chemical compound C1=C(N\C(N)=N/C(=O)OC)C(NC(=O)COC)=CC=C1OS(=O)(=O)C1=CC=CC(OCC(C)C)=C1 LSAQGPKXLWRUGT-UHFFFAOYSA-N 0.000 description 1
- SDPFRUQGUODQOX-UHFFFAOYSA-N [4-[(2-methoxyacetyl)amino]-3-[[(e)-n'-methoxycarbonylcarbamimidoyl]amino]phenyl] 3-chloro-4-methylbenzenesulfonate Chemical compound C1=C(N\C(N)=N/C(=O)OC)C(NC(=O)COC)=CC=C1OS(=O)(=O)C1=CC=C(C)C(Cl)=C1 SDPFRUQGUODQOX-UHFFFAOYSA-N 0.000 description 1
- IOARJLPLSGAIGG-UHFFFAOYSA-N [4-[(2-methoxyacetyl)amino]-3-[[(e)-n'-methoxycarbonylcarbamimidoyl]amino]phenyl] 3-methoxybenzenesulfonate Chemical compound C1=C(N\C(N)=N/C(=O)OC)C(NC(=O)COC)=CC=C1OS(=O)(=O)C1=CC=CC(OC)=C1 IOARJLPLSGAIGG-UHFFFAOYSA-N 0.000 description 1
- KLJCYFNEAWWWFY-UHFFFAOYSA-N [4-[(2-methoxyacetyl)amino]-3-[[(e)-n'-methoxycarbonylcarbamimidoyl]amino]phenyl] 3-propan-2-yloxybenzenesulfonate Chemical compound C1=C(N\C(N)=N/C(=O)OC)C(NC(=O)COC)=CC=C1OS(=O)(=O)C1=CC=CC(OC(C)C)=C1 KLJCYFNEAWWWFY-UHFFFAOYSA-N 0.000 description 1
- WRXCMINGXAVONE-UHFFFAOYSA-N [4-[(2-methoxyacetyl)amino]-3-[[(e)-n'-methoxycarbonylcarbamimidoyl]amino]phenyl] 3-propoxybenzenesulfonate Chemical compound CCCOC1=CC=CC(S(=O)(=O)OC=2C=C(N\C(N)=N/C(=O)OC)C(NC(=O)COC)=CC=2)=C1 WRXCMINGXAVONE-UHFFFAOYSA-N 0.000 description 1
- PSEVLPBSVNCJCN-UHFFFAOYSA-N [4-acetamido-3-[(n-methoxycarbonyl-n'-methylcarbamimidoyl)amino]phenyl] benzenesulfonate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)OC)=NC)=CC(OS(=O)(=O)C=2C=CC=CC=2)=C1 PSEVLPBSVNCJCN-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229960005473 fenbendazole Drugs 0.000 description 1
- IRHZVMHXVHSMKB-UHFFFAOYSA-N fenbendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1SC1=CC=CC=C1 IRHZVMHXVHSMKB-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 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
- 239000008187 granular material Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- BAXLBXFAUKGCDY-UHFFFAOYSA-N mebendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CC=C1 BAXLBXFAUKGCDY-UHFFFAOYSA-N 0.000 description 1
- 229960003439 mebendazole Drugs 0.000 description 1
- BPQPMIVFFHJAMW-UHFFFAOYSA-N methyl (ne)-n-[amino-[2-[(2-methoxyacetyl)amino]-5-phenoxyanilino]methylidene]carbamate Chemical compound C1=C(NC(N)=NC(=O)OC)C(NC(=O)COC)=CC=C1OC1=CC=CC=C1 BPQPMIVFFHJAMW-UHFFFAOYSA-N 0.000 description 1
- CTTQZMFVWLLLCK-UHFFFAOYSA-N methyl N-(N'-methylcarbamimidoyl)carbamate Chemical compound COC(=O)NC(N)=NC CTTQZMFVWLLLCK-UHFFFAOYSA-N 0.000 description 1
- PYYOLLJLOKSVNW-UHFFFAOYSA-N methyl N-[C-methylsulfanyl-N-(1-phenylethyl)carbonimidoyl]carbamate Chemical compound COC(=O)NC(SC)=NC(C)C1=CC=CC=C1 PYYOLLJLOKSVNW-UHFFFAOYSA-N 0.000 description 1
- PAVDBWFMFPEZIE-UHFFFAOYSA-N methyl n-(diaminomethylidene)carbamate Chemical compound COC(=O)NC(N)=N PAVDBWFMFPEZIE-UHFFFAOYSA-N 0.000 description 1
- ZVQWOWXQCUFSCA-UHFFFAOYSA-N methyl n-(n-butyl-c-methylsulfanylcarbonimidoyl)carbamate Chemical compound CCCCN=C(SC)NC(=O)OC ZVQWOWXQCUFSCA-UHFFFAOYSA-N 0.000 description 1
- YOHHRGBAXFZGRV-UHFFFAOYSA-N methyl n-(n-ethyl-c-methylsulfanylcarbonimidoyl)carbamate Chemical compound CCN=C(SC)NC(=O)OC YOHHRGBAXFZGRV-UHFFFAOYSA-N 0.000 description 1
- MVLWYBBNGYTKJB-UHFFFAOYSA-N methyl n-[n-(cyclohexylmethyl)-c-methylsulfanylcarbonimidoyl]carbamate Chemical compound COC(=O)NC(SC)=NCC1CCCCC1 MVLWYBBNGYTKJB-UHFFFAOYSA-N 0.000 description 1
- MZGCLZOJWGVQGX-UHFFFAOYSA-N methyl n-carbamimidoyl-n-phenylcarbamate Chemical class COC(=O)N(C(N)=N)C1=CC=CC=C1 MZGCLZOJWGVQGX-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 229950007337 parbendazole Drugs 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- HIYSRSZBCNBQSY-UHFFFAOYSA-N phenyl 3-[(n'-butyl-n-methoxycarbonylcarbamimidoyl)amino]-4-[(2-methoxyacetyl)amino]benzenesulfonate Chemical compound C1=C(NC(=O)COC)C(NC(NC(=O)OC)=NCCCC)=CC(S(=O)(=O)OC=2C=CC=CC=2)=C1 HIYSRSZBCNBQSY-UHFFFAOYSA-N 0.000 description 1
- LAZBFXGTLDXAJE-UHFFFAOYSA-N phenyl 4-(hexanoylamino)-3-[[(e)-n'-methoxycarbonylcarbamimidoyl]amino]benzenesulfonate Chemical compound C1=C(NC(=N)NC(=O)OC)C(NC(=O)CCCCC)=CC=C1S(=O)(=O)OC1=CC=CC=C1 LAZBFXGTLDXAJE-UHFFFAOYSA-N 0.000 description 1
- HDRHWXNZPUTFLK-UHFFFAOYSA-N phenyl 4-[(2-methoxyacetyl)amino]-3-[(n-methoxycarbonyl-n'-methylcarbamimidoyl)amino]benzenesulfonate Chemical compound C1=C(NC(NC(=O)OC)=NC)C(NC(=O)COC)=CC=C1S(=O)(=O)OC1=CC=CC=C1 HDRHWXNZPUTFLK-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/75—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782836385 DE2836385A1 (de) | 1978-08-19 | 1978-08-19 | Monocarboxylate von phenylguanidinsulfonsaeureestern, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO792696L true NO792696L (no) | 1979-02-20 |
Family
ID=6047464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO792696A NO792696L (no) | 1978-08-19 | 1979-08-17 | Monokarboksylater av fenylguanidinsyre-estere samt fremgangsmaate til deres fremstilling |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4254143A (xx) |
| EP (1) | EP0008438A1 (xx) |
| JP (1) | JPS5531083A (xx) |
| AU (1) | AU5003679A (xx) |
| DE (1) | DE2836385A1 (xx) |
| DK (1) | DK344379A (xx) |
| ES (2) | ES483350A1 (xx) |
| FI (1) | FI792548A (xx) |
| IL (1) | IL58066A0 (xx) |
| NO (1) | NO792696L (xx) |
| NZ (1) | NZ191336A (xx) |
| PT (1) | PT70076A (xx) |
| ZA (1) | ZA794355B (xx) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4348406A (en) | 1980-10-20 | 1982-09-07 | Schering Corporation | Novel guanidine derivatives |
| DE3232959A1 (de) * | 1982-09-04 | 1984-03-08 | Hoechst Ag, 6230 Frankfurt | Substituierte benzolsulfonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3412939A1 (de) * | 1984-04-06 | 1985-10-17 | Behringwerke Ag, 3550 Marburg | Substrate fuer hydrolasen, verfahren zu ihrer herstellung und ihre verwendung |
| JPH0825731B2 (ja) * | 1990-09-20 | 1996-03-13 | 信越化学工業株式会社 | 希土類リン酸塩の製造方法 |
| CN103848761B (zh) * | 2014-03-19 | 2016-03-23 | 连云港市亚晖医药化工有限公司 | O-甲基异脲甲酸甲酯的制备 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4024176A (en) * | 1974-05-15 | 1977-05-17 | Bayer Aktiengesellschaft | Substituted phenylguanidines and processes for their preparation and use |
| US4088780A (en) * | 1974-05-15 | 1978-05-09 | Bayer Aktiengesellschaft | Substituted phenylguanidines and processes for their preparation and use |
| DE2441201C2 (de) * | 1974-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Anthelminthisch wirksame 2-Carbalkoxyamino-5(6)-phenyl-sulfonyloxy-benzimidazole und Verfahren zu ihrer Herstellung |
| DE2441202C2 (de) * | 1974-08-28 | 1986-05-28 | Hoechst Ag, 6230 Frankfurt | 2-Carbalkoxyamino-benzimidazolyl-5(6)-sulfonsäure-phenylester, Verfahren zu ihrer Herstellung und diese enthaltende anthelmintische Mittel |
| DE2608238A1 (de) * | 1976-02-28 | 1977-09-08 | Hoechst Ag | Substituierte phenylguanidine und verfahren zu ihrer herstellung |
| DE2609994A1 (de) * | 1976-03-10 | 1977-09-15 | Bayer Ag | 2-formylamino-phenylguanidine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
1978
- 1978-08-19 DE DE19782836385 patent/DE2836385A1/de not_active Withdrawn
-
1979
- 1979-08-13 ES ES483350A patent/ES483350A1/es not_active Expired
- 1979-08-13 ES ES483349A patent/ES483349A1/es not_active Expired
- 1979-08-16 US US06/068,532 patent/US4254143A/en not_active Expired - Lifetime
- 1979-08-16 FI FI792548A patent/FI792548A/fi not_active Application Discontinuation
- 1979-08-16 EP EP79102980A patent/EP0008438A1/de not_active Withdrawn
- 1979-08-17 IL IL58066A patent/IL58066A0/xx unknown
- 1979-08-17 NO NO792696A patent/NO792696L/no unknown
- 1979-08-17 PT PT70076A patent/PT70076A/pt unknown
- 1979-08-17 DK DK344379A patent/DK344379A/da unknown
- 1979-08-17 AU AU50036/79A patent/AU5003679A/en not_active Abandoned
- 1979-08-17 NZ NZ191336A patent/NZ191336A/xx unknown
- 1979-08-17 ZA ZA00794355A patent/ZA794355B/xx unknown
- 1979-08-18 JP JP10453679A patent/JPS5531083A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FI792548A (fi) | 1980-02-20 |
| NZ191336A (en) | 1981-01-23 |
| ES483350A1 (es) | 1980-04-16 |
| IL58066A0 (en) | 1979-12-30 |
| EP0008438A1 (de) | 1980-03-05 |
| ES483349A1 (es) | 1980-04-16 |
| DE2836385A1 (de) | 1980-03-06 |
| US4254143A (en) | 1981-03-03 |
| JPS5531083A (en) | 1980-03-05 |
| ZA794355B (en) | 1980-08-27 |
| PT70076A (de) | 1979-09-01 |
| AU5003679A (en) | 1980-02-28 |
| DK344379A (da) | 1980-02-20 |
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