FI60203C - Foerfarande foer framstaellning av saosom maskmedel anvaendbara 2-karbalkoxiamino-5(6)-fenylsulfonyloxibensimidazoler - Google Patents
Foerfarande foer framstaellning av saosom maskmedel anvaendbara 2-karbalkoxiamino-5(6)-fenylsulfonyloxibensimidazoler Download PDFInfo
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- FI60203C FI60203C FI752397A FI752397A FI60203C FI 60203 C FI60203 C FI 60203C FI 752397 A FI752397 A FI 752397A FI 752397 A FI752397 A FI 752397A FI 60203 C FI60203 C FI 60203C
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- Finland
- Prior art keywords
- formula
- acid
- ester
- alkyl
- nitro
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- -1 cyanamide carboxylate Chemical class 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 150000004987 o-phenylenediamines Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 230000000507 anthelmentic effect Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 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 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 1
- IFSGDVQZOBXLRG-UHFFFAOYSA-N dichloromethylideneurea Chemical compound NC(=O)N=C(Cl)Cl IFSGDVQZOBXLRG-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- COAWUHRGJYIVPX-UHFFFAOYSA-N (3,4-diaminophenyl) benzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1OS(=O)(=O)C1=CC=CC=C1 COAWUHRGJYIVPX-UHFFFAOYSA-N 0.000 description 11
- RMQZQBMUDNFKLK-UHFFFAOYSA-N (3,4-diaminophenyl) 3-(trifluoromethyl)benzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1OS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 RMQZQBMUDNFKLK-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- LVMOKIQHDKDNBI-UHFFFAOYSA-N 3-(trifluoromethyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 LVMOKIQHDKDNBI-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- BVJKOVDYRDCLHQ-UHFFFAOYSA-N (4-amino-3-nitrophenyl) 3-(trifluoromethyl)benzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 BVJKOVDYRDCLHQ-UHFFFAOYSA-N 0.000 description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- FGUJEHLUNQOXRC-UHFFFAOYSA-N (4-amino-3-nitrophenyl) benzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OS(=O)(=O)C1=CC=CC=C1 FGUJEHLUNQOXRC-UHFFFAOYSA-N 0.000 description 6
- UPUDSFHDZIXLGD-UHFFFAOYSA-N 4-(4-amino-3-nitrophenoxy)-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OC1=CC=C(N)C([N+]([O-])=O)=C1 UPUDSFHDZIXLGD-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241001494479 Pecora Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229940092714 benzenesulfonic acid Drugs 0.000 description 4
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 4
- YHMFTWZCHPQXRM-UHFFFAOYSA-N dichloromethylidenecarbamic acid Chemical compound OC(=O)N=C(Cl)Cl YHMFTWZCHPQXRM-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- RQBIGPMJQUKYAH-UHFFFAOYSA-N 4-(3,4-diaminophenoxy)benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1OC1=CC=C(N)C(N)=C1 RQBIGPMJQUKYAH-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- BEZZFPOZAYTVHN-UHFFFAOYSA-N oxfendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1S(=O)C1=CC=CC=C1 BEZZFPOZAYTVHN-UHFFFAOYSA-N 0.000 description 3
- 244000045947 parasite Species 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 241000283903 Ovis aries Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000007530 organic bases Chemical group 0.000 description 2
- 229960004454 oxfendazole Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- FCIMQHVQCUQPNZ-UHFFFAOYSA-N (3,4-diaminophenyl) 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S(=O)(=O)OC1=CC=C(N)C(N)=C1 FCIMQHVQCUQPNZ-UHFFFAOYSA-N 0.000 description 1
- FWKPVMFNNMRWNN-UHFFFAOYSA-N (3,4-diaminophenyl) 3,4-dichlorobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 FWKPVMFNNMRWNN-UHFFFAOYSA-N 0.000 description 1
- ZYOLIVUFDMHHDP-UHFFFAOYSA-N (3,4-diaminophenyl) 3,5-dichlorobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1OS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 ZYOLIVUFDMHHDP-UHFFFAOYSA-N 0.000 description 1
- IAICOIQLCDFTCS-UHFFFAOYSA-N (3,4-diaminophenyl) 3-bromobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1OS(=O)(=O)C1=CC=CC(Br)=C1 IAICOIQLCDFTCS-UHFFFAOYSA-N 0.000 description 1
- SCEZQKVLURSOMD-UHFFFAOYSA-N (3,4-diaminophenyl) 3-chlorobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1OS(=O)(=O)C1=CC=CC(Cl)=C1 SCEZQKVLURSOMD-UHFFFAOYSA-N 0.000 description 1
- BQCZKCXCSYRZOT-UHFFFAOYSA-N (3,4-diaminophenyl) 3-cyanobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1OS(=O)(=O)C1=CC=CC(C#N)=C1 BQCZKCXCSYRZOT-UHFFFAOYSA-N 0.000 description 1
- XJZDPPUAESRHGO-UHFFFAOYSA-N (3,4-diaminophenyl) 3-methylbenzenesulfonate Chemical compound CC1=CC=CC(S(=O)(=O)OC=2C=C(N)C(N)=CC=2)=C1 XJZDPPUAESRHGO-UHFFFAOYSA-N 0.000 description 1
- RXABABWUGSSNJH-UHFFFAOYSA-N (3,4-diaminophenyl) 4-chlorobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RXABABWUGSSNJH-UHFFFAOYSA-N 0.000 description 1
- KZKSYXCDLMUCLX-UHFFFAOYSA-N (3,4-diaminophenyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=C(N)C(N)=C1 KZKSYXCDLMUCLX-UHFFFAOYSA-N 0.000 description 1
- HFJQRIIFZLQNGT-UHFFFAOYSA-N (3,4-diaminophenyl) 4-propan-2-ylbenzenesulfonate Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)OC1=CC=C(N)C(N)=C1 HFJQRIIFZLQNGT-UHFFFAOYSA-N 0.000 description 1
- IRFCVFVFMDCIEC-UHFFFAOYSA-N (3,4-diaminophenyl) 4-tert-butylbenzenesulfonate Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)OC1=CC=C(N)C(N)=C1 IRFCVFVFMDCIEC-UHFFFAOYSA-N 0.000 description 1
- MWXKHNVEMYGSAU-UHFFFAOYSA-N (4-amino-3-nitrophenyl) 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S(=O)(=O)OC1=CC=C(N)C([N+]([O-])=O)=C1 MWXKHNVEMYGSAU-UHFFFAOYSA-N 0.000 description 1
- CJLVYVIRROZUDT-UHFFFAOYSA-N (4-amino-3-nitrophenyl) 3,4-dichlorobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 CJLVYVIRROZUDT-UHFFFAOYSA-N 0.000 description 1
- TVGNDHVZRJIZOD-UHFFFAOYSA-N (4-amino-3-nitrophenyl) 3,5-dichlorobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 TVGNDHVZRJIZOD-UHFFFAOYSA-N 0.000 description 1
- FEBMTEPYYOQOEZ-UHFFFAOYSA-N (4-amino-3-nitrophenyl) 3-bromobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OS(=O)(=O)C1=CC=CC(Br)=C1 FEBMTEPYYOQOEZ-UHFFFAOYSA-N 0.000 description 1
- IUEMAZKNZCEOIB-UHFFFAOYSA-N (4-amino-3-nitrophenyl) 3-chlorobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OS(=O)(=O)C1=CC=CC(Cl)=C1 IUEMAZKNZCEOIB-UHFFFAOYSA-N 0.000 description 1
- FCQOHDIBJXQLQJ-UHFFFAOYSA-N (4-amino-3-nitrophenyl) 3-cyanobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OS(=O)(=O)C1=CC=CC(C#N)=C1 FCQOHDIBJXQLQJ-UHFFFAOYSA-N 0.000 description 1
- BLXYPMRZLGQNTF-UHFFFAOYSA-N (4-amino-3-nitrophenyl) 3-methylbenzenesulfonate Chemical compound CC1=CC=CC(S(=O)(=O)OC=2C=C(C(N)=CC=2)[N+]([O-])=O)=C1 BLXYPMRZLGQNTF-UHFFFAOYSA-N 0.000 description 1
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- NZODFOPVQYWMLJ-UHFFFAOYSA-N 1h-benzimidazol-2-yl 4-chlorobenzenesulfonate Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)OC1=NC2=CC=CC=C2N1 NZODFOPVQYWMLJ-UHFFFAOYSA-N 0.000 description 1
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NLURCCKGOCJMIV-UHFFFAOYSA-N NC=1C=C(C=CC1N)OS(=O)(=O)C1=C(C=CC(=C1)C(C)C)C Chemical compound NC=1C=C(C=CC1N)OS(=O)(=O)C1=C(C=CC(=C1)C(C)C)C NLURCCKGOCJMIV-UHFFFAOYSA-N 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- 241000243796 Trichostrongylus colubriformis Species 0.000 description 1
- NUWHYLCGFBLCOZ-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC1N)OS(=O)(=O)C1=C(C=CC(=C1)C(C)C)C Chemical compound [N+](=O)([O-])C=1C=C(C=CC1N)OS(=O)(=O)C1=C(C=CC(=C1)C(C)C)C NUWHYLCGFBLCOZ-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001556 benzimidazoles Chemical class 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
- 239000000872 buffer Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- IKYMJBKVGYKTMX-UHFFFAOYSA-N carbamic acid;ethene Chemical compound C=C.NC(O)=O IKYMJBKVGYKTMX-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- INBDPOJZYZJUDA-UHFFFAOYSA-N methanedithiol Chemical compound SCS INBDPOJZYZJUDA-UHFFFAOYSA-N 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- IUROBCDXAGBTOV-UHFFFAOYSA-N methyl n-(dichloromethylidene)carbamate Chemical compound COC(=O)N=C(Cl)Cl IUROBCDXAGBTOV-UHFFFAOYSA-N 0.000 description 1
- LCBJJCQPMXGINF-UHFFFAOYSA-N methyl n-[bis(methylsulfanyl)methylidene]carbamate Chemical compound COC(=O)N=C(SC)SC LCBJJCQPMXGINF-UHFFFAOYSA-N 0.000 description 1
- ZMDGICHYDVYQDX-UHFFFAOYSA-N methylidenecarbamic acid Chemical compound OC(=O)N=C ZMDGICHYDVYQDX-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000546 pharmaceutical excipient 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
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000000843 powder Substances 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
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2441201 | 1974-08-28 | ||
| DE2441201A DE2441201C2 (de) | 1974-08-28 | 1974-08-28 | Anthelminthisch wirksame 2-Carbalkoxyamino-5(6)-phenyl-sulfonyloxy-benzimidazole und Verfahren zu ihrer Herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI752397A7 FI752397A7 (cs) | 1976-02-29 |
| FI60203B FI60203B (fi) | 1981-08-31 |
| FI60203C true FI60203C (fi) | 1981-12-10 |
Family
ID=5924287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI752397A FI60203C (fi) | 1974-08-28 | 1975-08-26 | Foerfarande foer framstaellning av saosom maskmedel anvaendbara 2-karbalkoxiamino-5(6)-fenylsulfonyloxibensimidazoler |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US3996368A (cs) |
| JP (1) | JPS5910350B2 (cs) |
| AT (1) | AT347935B (cs) |
| BE (1) | BE832859A (cs) |
| BG (3) | BG27234A3 (cs) |
| CA (1) | CA1059135A (cs) |
| CH (1) | CH613195A5 (cs) |
| CS (1) | CS196278B2 (cs) |
| DD (1) | DD124978A5 (cs) |
| DE (1) | DE2441201C2 (cs) |
| DK (1) | DK136188C (cs) |
| ES (1) | ES440386A1 (cs) |
| FI (1) | FI60203C (cs) |
| FR (1) | FR2282881A1 (cs) |
| GB (1) | GB1472718A (cs) |
| HU (1) | HU171120B (cs) |
| IE (1) | IE41521B1 (cs) |
| IL (1) | IL47997A (cs) |
| IT (1) | IT1041926B (cs) |
| KE (1) | KE3070A (cs) |
| LU (1) | LU73255A1 (cs) |
| MY (1) | MY8100147A (cs) |
| NL (1) | NL187208C (cs) |
| NO (1) | NO140591C (cs) |
| SE (1) | SE417509B (cs) |
| SU (3) | SU576044A3 (cs) |
| ZA (1) | ZA755486B (cs) |
| ZM (1) | ZM12575A1 (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3132167A1 (de) * | 1981-08-14 | 1983-03-03 | Hoechst Ag, 6000 Frankfurt | "5(6)-phenylsulfonyloxy-benzimidazolderivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung gegen leberegel" |
| DE2608238A1 (de) * | 1976-02-28 | 1977-09-08 | Hoechst Ag | Substituierte phenylguanidine und verfahren zu ihrer herstellung |
| DE2653766A1 (de) * | 1976-11-26 | 1978-06-01 | Bayer Ag | Substituierte benzolsulfonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2836385A1 (de) * | 1978-08-19 | 1980-03-06 | Hoechst Ag | Monocarboxylate von phenylguanidinsulfonsaeureestern, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3232959A1 (de) * | 1982-09-04 | 1984-03-08 | Hoechst Ag, 6230 Frankfurt | Substituierte benzolsulfonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3247615A1 (de) * | 1982-12-23 | 1984-07-05 | Hoechst Ag, 6230 Frankfurt | Substituierte phenylsulfonyloxybenzimidazolcarbaminate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3705227A1 (de) * | 1987-02-19 | 1988-09-01 | Bayer Ag | Anthelminthische wirkstoffkombinationen |
| EP1298125A1 (en) * | 2001-09-26 | 2003-04-02 | Aventis Pharma S.A. | Substituted benzimidazole compounds and their use for the treatment of cancer |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE666795A (cs) * | 1964-08-04 | 1966-01-13 | ||
| US3562290A (en) * | 1967-11-07 | 1971-02-09 | Du Pont | Process for making 2-benzimidazolecarbamic acid alkyl esters |
| DE1932297C3 (de) * | 1969-06-26 | 1974-09-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Benzimidazol -2-carbaminsäureestern |
| BE793358A (fr) * | 1971-12-27 | 1973-06-27 | Hoechst Ag | Nouveaux derives de 2-carbalcoxy-amino-benzimidazole presentantune activite anthelmintique et leur procede de preparation |
| ZA739220B (en) * | 1972-12-29 | 1975-07-30 | Syntex Inc | 5(6)-benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US3929821A (en) * | 1972-12-29 | 1975-12-30 | Syntex Inc | 5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives |
| US3929824A (en) * | 1972-12-29 | 1975-12-30 | Syntex Inc | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
-
1974
- 1974-08-28 DE DE2441201A patent/DE2441201C2/de not_active Expired
-
1975
- 1975-08-15 CS CS755619A patent/CS196278B2/cs unknown
- 1975-08-22 ES ES440386A patent/ES440386A1/es not_active Expired
- 1975-08-22 FR FR7526015A patent/FR2282881A1/fr active Granted
- 1975-08-22 NL NLAANVRAGE7509957,A patent/NL187208C/xx not_active IP Right Cessation
- 1975-08-23 BG BG031578A patent/BG27234A3/xx unknown
- 1975-08-23 BG BG030848A patent/BG27084A3/xx unknown
- 1975-08-25 SE SE7509442A patent/SE417509B/xx not_active IP Right Cessation
- 1975-08-26 FI FI752397A patent/FI60203C/fi not_active IP Right Cessation
- 1975-08-26 GB GB3521875A patent/GB1472718A/en not_active Expired
- 1975-08-26 LU LU73255A patent/LU73255A1/xx unknown
- 1975-08-26 IT IT26581/75A patent/IT1041926B/it active
- 1975-08-26 CH CH1106875A patent/CH613195A5/xx not_active IP Right Cessation
- 1975-08-26 US US05/607,928 patent/US3996368A/en not_active Expired - Lifetime
- 1975-08-26 DD DD188034A patent/DD124978A5/xx unknown
- 1975-08-26 ZM ZM125/75A patent/ZM12575A1/xx unknown
- 1975-08-26 IL IL47997A patent/IL47997A/xx unknown
- 1975-08-27 CA CA234,272A patent/CA1059135A/en not_active Expired
- 1975-08-27 ZA ZA00755486A patent/ZA755486B/xx unknown
- 1975-08-27 HU HU75HO00001830A patent/HU171120B/hu not_active IP Right Cessation
- 1975-08-27 AT AT663775A patent/AT347935B/de not_active IP Right Cessation
- 1975-08-27 NO NO752944A patent/NO140591C/no unknown
- 1975-08-27 SU SU7502167451A patent/SU576044A3/ru active
- 1975-08-27 DK DK384875A patent/DK136188C/da active
- 1975-08-27 IE IE1873/75A patent/IE41521B1/en unknown
- 1975-08-28 JP JP50103563A patent/JPS5910350B2/ja not_active Expired
- 1975-08-28 BE BE159560A patent/BE832859A/xx not_active IP Right Cessation
- 1975-11-25 BG BG031577A patent/BG27233A3/bg unknown
-
1976
- 1976-09-27 SU SU762404805A patent/SU592355A3/ru active
- 1976-09-29 SU SU762404894A patent/SU592356A3/ru active
-
1980
- 1980-07-30 KE KE3070A patent/KE3070A/xx unknown
-
1981
- 1981-12-30 MY MY147/81A patent/MY8100147A/xx unknown
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