CS201522B2 - Process for preparing benzimidazolcarbamates - Google Patents
Process for preparing benzimidazolcarbamates Download PDFInfo
- Publication number
- CS201522B2 CS201522B2 CS704330A CS433070A CS201522B2 CS 201522 B2 CS201522 B2 CS 201522B2 CS 704330 A CS704330 A CS 704330A CS 433070 A CS433070 A CS 433070A CS 201522 B2 CS201522 B2 CS 201522B2
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- Czechoslovakia
- Prior art keywords
- parts
- formula
- methyl
- compound
- ketones
- Prior art date
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- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 6
- 125000005059 halophenyl group Chemical group 0.000 claims abstract description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims abstract description 4
- 150000007513 acids Chemical class 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical class NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 13
- 150000002576 ketones Chemical class 0.000 abstract description 10
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract description 5
- 230000000507 anthelmentic effect Effects 0.000 abstract description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 3
- 238000005915 ammonolysis reaction Methods 0.000 abstract description 2
- 239000000969 carrier Substances 0.000 abstract description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 abstract 3
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 abstract 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 150000005171 halobenzenes Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 15
- -1 ethoxy, propoxy Chemical group 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 241001494479 Pecora Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 244000000013 helminth Species 0.000 description 3
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- NGOOFAMQPUEDJM-UHFFFAOYSA-N (4-amino-3-nitrophenyl)-phenylmethanone Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1C(=O)C1=CC=CC=C1 NGOOFAMQPUEDJM-UHFFFAOYSA-N 0.000 description 2
- YBDBYPQFIMSFJW-UHFFFAOYSA-N (4-chloro-3-nitrophenyl)-phenylmethanone Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C(=O)C=2C=CC=CC=2)=C1 YBDBYPQFIMSFJW-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 108010034145 Helminth Proteins Proteins 0.000 description 2
- 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 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000760144 Syphacia muris Species 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 235000013330 chicken meat Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JFWMYCVMQSLLOO-UHFFFAOYSA-N cyclobutanecarbonyl chloride Chemical compound ClC(=O)C1CCC1 JFWMYCVMQSLLOO-UHFFFAOYSA-N 0.000 description 2
- BIPUHAHGLJKIPK-UHFFFAOYSA-N dicyclopropylmethanone Chemical compound C1CC1C(=O)C1CC1 BIPUHAHGLJKIPK-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229950007337 parbendazole Drugs 0.000 description 2
- 210000000664 rectum Anatomy 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- VNCHICMXBKDTOS-UHFFFAOYSA-N (3,4-diaminophenyl)-phenylmethanone;hydron;chloride Chemical compound Cl.C1=C(N)C(N)=CC=C1C(=O)C1=CC=CC=C1 VNCHICMXBKDTOS-UHFFFAOYSA-N 0.000 description 1
- OPSFCTBBDIDFJM-UHFFFAOYSA-N (4-chlorophenyl)-cyclopropylmethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CC1 OPSFCTBBDIDFJM-UHFFFAOYSA-N 0.000 description 1
- WJXNSSZXGGXPTE-UHFFFAOYSA-N 1-(4-amino-3-nitrophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 WJXNSSZXGGXPTE-UHFFFAOYSA-N 0.000 description 1
- KEBUEWXZQBMCNB-UHFFFAOYSA-N 1h-benzimidazol-2-yl carbamate Chemical class C1=CC=C2NC(OC(=O)N)=NC2=C1 KEBUEWXZQBMCNB-UHFFFAOYSA-N 0.000 description 1
- IWLGXPWQZDOMSB-UHFFFAOYSA-N 4-chloro-3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC=C1Cl IWLGXPWQZDOMSB-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000244186 Ascaris Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000931178 Bunostomum Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000253350 Capillaria Species 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 241000893172 Chabertia Species 0.000 description 1
- 241001247414 Couma Species 0.000 description 1
- 241000498255 Enterobius vermicularis Species 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 208000006968 Helminthiasis Diseases 0.000 description 1
- 208000015336 Helminthic disease Diseases 0.000 description 1
- 241000920462 Heterakis Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 241001137882 Nematodirus Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241001256311 Selenis Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000244174 Strongyloides Species 0.000 description 1
- 241000975704 Syphacia Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KXOSBEZVUBCWBN-UHFFFAOYSA-N bis(2-cyclopentyl-4-fluorophenyl)methanone Chemical compound C1CCCC1C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1C1CCCC1 KXOSBEZVUBCWBN-UHFFFAOYSA-N 0.000 description 1
- AIKXISKDXIUFQO-UHFFFAOYSA-N bis(3-amino-2-nitrophenyl)methanone Chemical class NC1=CC=CC(C(=O)C=2C(=C(N)C=CC=2)[N+]([O-])=O)=C1[N+]([O-])=O AIKXISKDXIUFQO-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([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
- WEPUZBYKXNKSDH-UHFFFAOYSA-N cyclopentanecarbonyl chloride Chemical compound ClC(=O)C1CCCC1 WEPUZBYKXNKSDH-UHFFFAOYSA-N 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
- 230000008021 deposition Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000004987 o-phenylenediamines Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BWILYWWHXDGKQA-UHFFFAOYSA-M potassium propanoate Chemical compound [K+].CCC([O-])=O BWILYWWHXDGKQA-UHFFFAOYSA-M 0.000 description 1
- 239000004331 potassium propionate Substances 0.000 description 1
- 235000010332 potassium propionate Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83524669A | 1969-06-20 | 1969-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS201522B2 true CS201522B2 (en) | 1980-11-28 |
Family
ID=25269027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS704330A CS201522B2 (en) | 1969-06-20 | 1970-06-19 | Process for preparing benzimidazolcarbamates |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3657267A (de) |
| JP (1) | JPS501272B1 (de) |
| AT (2) | AT307798B (de) |
| BE (1) | BE752089A (de) |
| CH (1) | CH520684A (de) |
| CS (1) | CS201522B2 (de) |
| DK (2) | DK134602B (de) |
| ES (1) | ES380579A1 (de) |
| FI (1) | FI52719C (de) |
| FR (1) | FR2052988B1 (de) |
| GB (1) | GB1307306A (de) |
| HK (1) | HK77976A (de) |
| IL (1) | IL34746A (de) |
| IT (1) | IT1035027B (de) |
| MY (1) | MY7300477A (de) |
| NL (1) | NL147139B (de) |
| PL (1) | PL72724B1 (de) |
| SE (1) | SE366045B (de) |
| YU (1) | YU34195B (de) |
| ZA (1) | ZA704191B (de) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2201208A1 (de) * | 1972-01-12 | 1973-08-02 | Basf Ag | Verfahren zur herstellung von aromatischen ketonen |
| US3929821A (en) * | 1972-12-29 | 1975-12-30 | Syntex Inc | 5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives |
| US4258198A (en) * | 1973-05-29 | 1981-03-24 | Smithkline Corporation | 5-Cycloalkyl thio- and oxy-2-carbalkoxyaminobenzimidazoles |
| US3969526A (en) * | 1973-05-29 | 1976-07-13 | Smithkline Corporation | Anthelmintic 5-heterocycliothio and oxy-2-carbalkoxyaminobenzimidazles |
| DE2443297A1 (de) * | 1974-09-10 | 1976-03-18 | Hoechst Ag | Anthelminthisch wirksame basisch substituierte 2-carbalkoxy-amino-benzimidazolyl-5(6)-phenylaether und -ketone sowie verfahren zu ihrer herstellung |
| US4026936A (en) * | 1975-08-07 | 1977-05-31 | Hoffmann-La Roche Inc. | Anthelmintic pyridine and thiazole substituted benzimidazole carbamates |
| US4031234A (en) * | 1975-08-18 | 1977-06-21 | Syntex (U.S.A.) Inc. | 1,5(6)-Disubstituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US4032536A (en) * | 1976-07-22 | 1977-06-28 | Janssen Pharmaceutica N.V. | (1h-benzimidazol-2-yl)carbamates |
| IT1076022B (it) * | 1977-04-20 | 1985-04-22 | Montedison Spa | Benzimidazolcarbammati antielmintici |
| JPS5535611A (en) * | 1978-08-31 | 1980-03-12 | Matsushita Electric Works Ltd | Instrument with mouth washing instrument |
| US4299837A (en) | 1979-12-05 | 1981-11-10 | Montedison S.P.A. | Anthelmintic benzimidazole-carbamates |
| US4435418A (en) | 1982-12-13 | 1984-03-06 | Smithkline Beckman Corporation | 5-Phenylethenylbenzimidazoles |
| US4438135A (en) | 1983-01-07 | 1984-03-20 | Smithkline Beckman Corporation | 1-(3,4-Bis-(3-(lower alkoxycarbonyl)-2-thioureido)-phenyl-1-phenylthylenes |
| US5256681A (en) * | 1989-03-15 | 1993-10-26 | Janssen Pharmaceutica N.V. | [5(6)-(benzisoxa-,benzisothia-or indazol-3-yl)-1H-benzimidazol-2-yl]carbamates |
| WO1990010630A1 (en) * | 1989-03-15 | 1990-09-20 | Janssen Pharmaceutica N.V. | [5(6)-(benzisoxa-, benzisothia- or indazol-3-yl)-1h-benzimidazol-2-yl] carbamates |
| NZ232785A (en) * | 1989-03-15 | 1991-03-26 | Janssen Pharmaceutica Nv | 5-(1,2 benzisoxazol-, benzimidazol and benzisothiazol-3- yl)-1h-benzimadazol-2-yl carbamic acid ester derivatives preparatory processes, intermediates and anthelmintic compositions |
| US5278181A (en) * | 1992-05-12 | 1994-01-11 | Board Of Regents Acting On Behalf Of The University Of Michigan | Soluble alkyl[5-[amino (phenyl)methyl]-1H-benzimidazol-2-yl] carbamate anthelmintics |
| US7893271B2 (en) * | 2005-07-28 | 2011-02-22 | Intervet International B.V. | Benzimidazole carbamates and (thio) carbamates, and the synthesis and use thereof |
| EP2032046B1 (de) * | 2006-06-12 | 2015-11-04 | Smith & Nephew, Inc. | Systeme und vorrichtungen zur schienbeingeweberesektion |
| CA2660647C (en) | 2006-06-14 | 2015-07-28 | Intervet International B.V. | A suspension comprising benzimidazole carbamate and a polysorbate |
| WO2013110975A1 (es) | 2012-01-27 | 2013-08-01 | Siegfried Rhein S.A. De C.V. | Composición de nitazoxanida mejorada y proceso para prepararla |
| WO2014049397A1 (es) | 2012-09-27 | 2014-04-03 | Siegfried Rhein S.A. De C.V. | Composición sinérgica de nitazoxanida y mebendazol, procesos para prepararla y el uso de dicha composición para el tratamiento de la parasitosis humana |
| CN108884054B (zh) | 2015-11-30 | 2022-08-02 | 儿童医学中心公司 | 用于治疗增殖性疾病的化合物 |
| ES2962526T3 (es) | 2017-06-22 | 2024-03-19 | Cipla Ltd | Secretagogos PAR-4 para el tratamiento del cáncer |
| CN109467512B (zh) * | 2018-12-18 | 2021-06-08 | 苏州开元民生科技股份有限公司 | 一种3,4-二氨基-二苯甲酮的合成方法 |
| CN113979949A (zh) * | 2021-12-17 | 2022-01-28 | 山东国邦药业有限公司 | 一种氟苯咪唑的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1111957A (en) * | 1966-05-20 | 1968-05-01 | Smith Kline French Lab | Improvements in or relating to anthelmintic compositions |
-
1969
- 1969-06-20 US US835246A patent/US3657267A/en not_active Expired - Lifetime
-
1970
- 1970-05-29 GB GB2604470A patent/GB1307306A/en not_active Expired
- 1970-05-29 CH CH809370A patent/CH520684A/fr not_active IP Right Cessation
- 1970-06-08 FR FR707021022A patent/FR2052988B1/fr not_active Expired
- 1970-06-09 ES ES380579A patent/ES380579A1/es not_active Expired
- 1970-06-16 PL PL1970141321A patent/PL72724B1/pl unknown
- 1970-06-17 SE SE08385/70A patent/SE366045B/xx unknown
- 1970-06-17 BE BE752089D patent/BE752089A/xx not_active IP Right Cessation
- 1970-06-18 IL IL34746A patent/IL34746A/xx unknown
- 1970-06-18 AT AT549770A patent/AT307798B/de not_active IP Right Cessation
- 1970-06-18 YU YU1544/70A patent/YU34195B/xx unknown
- 1970-06-18 IT IT51551/70A patent/IT1035027B/it active
- 1970-06-18 AT AT825571A patent/AT302358B/de not_active IP Right Cessation
- 1970-06-18 FI FI701720A patent/FI52719C/fi active
- 1970-06-19 NL NL707009024A patent/NL147139B/xx not_active IP Right Cessation
- 1970-06-19 ZA ZA704191A patent/ZA704191B/xx unknown
- 1970-06-19 JP JP45053435A patent/JPS501272B1/ja active Pending
- 1970-06-19 CS CS704330A patent/CS201522B2/cs unknown
- 1970-06-22 DK DK321770AA patent/DK134602B/da not_active IP Right Cessation
-
1973
- 1973-12-30 MY MY477/73A patent/MY7300477A/xx unknown
-
1975
- 1975-12-19 DK DK580275A patent/DK580275A/da unknown
-
1976
- 1976-12-09 HK HK779/76*UA patent/HK77976A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK134602B (da) | 1976-12-06 |
| DK134602C (de) | 1977-06-27 |
| JPS501272B1 (de) | 1975-01-16 |
| SE366045B (de) | 1974-04-08 |
| AT302358B (de) | 1972-10-10 |
| DE2029637A1 (de) | 1971-02-18 |
| DK580275A (da) | 1975-12-19 |
| YU34195B (en) | 1979-02-28 |
| GB1307306A (en) | 1973-02-21 |
| NL147139B (nl) | 1975-09-15 |
| IL34746A (en) | 1973-01-30 |
| FI52719B (de) | 1977-08-01 |
| FI52719C (fi) | 1977-11-10 |
| US3657267A (en) | 1972-04-18 |
| YU154470A (en) | 1978-09-18 |
| IT1035027B (it) | 1979-10-20 |
| HK77976A (en) | 1976-12-17 |
| FR2052988A1 (de) | 1971-04-16 |
| FR2052988B1 (de) | 1973-08-10 |
| ZA704191B (en) | 1972-02-23 |
| AT307798B (de) | 1973-06-12 |
| MY7300477A (en) | 1973-12-31 |
| PL72724B1 (de) | 1974-08-30 |
| NL7009024A (de) | 1970-12-22 |
| BE752089A (fr) | 1970-12-17 |
| DE2029637B2 (de) | 1976-09-23 |
| ES380579A1 (es) | 1973-04-01 |
| IL34746A0 (en) | 1970-08-19 |
| CH520684A (fr) | 1972-03-31 |
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