NO833158L - Substituerte benzensulfonsyreestere, fremgangsmaate til deres fremstilling og deres anvendelse som legemiddel - Google Patents

Substituerte benzensulfonsyreestere, fremgangsmaate til deres fremstilling og deres anvendelse som legemiddel

Info

Publication number: NO833158L
Authority: NO; Norway
Prior art keywords: formula; atoms; substituted; compound; alkyl
Prior art date: 1982-09-04

Application number

NO833158A

Other languages

English (en)

Norwegian (no)

Inventor

Manfred Roesner

Josef Urbanietz

Heinz Loewe

Dieter Duewel

Reinhard Kirsch

Original Assignee

Hoechst Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-09-04

Filing date

1983-09-02

Publication date

1984-03-05

1983-09-02 Application filed by Hoechst Ag filed Critical Hoechst Ag

1984-03-05 Publication of NO833158L publication Critical patent/NO833158L/no

Links

238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title description 6
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 title 1
-1 acetamino Chemical group 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
150000008107 benzenesulfonic acids Chemical class 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
150000002828 nitro derivatives Chemical class 0.000 claims description 6
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
DUIOPKIIICUYRZ-NJFSPNSNSA-N aminourea Chemical class NN[14C](N)=O DUIOPKIIICUYRZ-NJFSPNSNSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
244000000013 helminth Species 0.000 claims 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229940092714 benzenesulfonic acid Drugs 0.000 claims 1
LDUOHXCVIFQGBK-UHFFFAOYSA-N carbonisocyanatidic acid Chemical compound OC(=O)N=C=O LDUOHXCVIFQGBK-UHFFFAOYSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
239000011593 sulfur Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical class CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000002844 melting Methods 0.000 description 15
230000008018 melting Effects 0.000 description 15
238000003756 stirring Methods 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000001816 cooling Methods 0.000 description 12
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 9
239000000243 solution Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 7
235000011054 acetic acid Nutrition 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000007868 Raney catalyst Substances 0.000 description 5
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
229910000564 Raney nickel Inorganic materials 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
238000010992 reflux Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
CBQNJOWKUBLTSF-UHFFFAOYSA-N [3-amino-4-(carbamoylamino)phenyl] 3-(trifluoromethyl)benzenesulfonate Chemical compound C1=C(N)C(NC(=O)N)=CC=C1OS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 CBQNJOWKUBLTSF-UHFFFAOYSA-N 0.000 description 3
HLKRDPGZVNQQAG-UHFFFAOYSA-N [4-(carbamoylamino)-3-nitrophenyl] 3-(trifluoromethyl)benzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)N)=CC=C1OS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 HLKRDPGZVNQQAG-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
LBFAAYMITJMZOC-UHFFFAOYSA-N methyl n-(sulfanylidenemethylidene)carbamate Chemical compound COC(=O)N=C=S LBFAAYMITJMZOC-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
YSAPYRFQLHBJSV-UHFFFAOYSA-N phenyl 3-amino-4-(carbamoylamino)benzenesulfonate Chemical compound C1=C(N)C(NC(=O)N)=CC=C1S(=O)(=O)OC1=CC=CC=C1 YSAPYRFQLHBJSV-UHFFFAOYSA-N 0.000 description 3
SDILANDQXWIRDR-UHFFFAOYSA-N phenyl 4-(carbamoylamino)-3-nitrobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)N)=CC=C1S(=O)(=O)OC1=CC=CC=C1 SDILANDQXWIRDR-UHFFFAOYSA-N 0.000 description 3
230000007017 scission Effects 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000000507 anthelmentic effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
UPJWAKUNQVOESN-UHFFFAOYSA-N carbonisothiocyanatidic acid Chemical compound OC(=O)N=C=S UPJWAKUNQVOESN-UHFFFAOYSA-N 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical class N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
UVNDUFUGVWNRIP-UHFFFAOYSA-N phenyl 4-(acetylcarbamoylamino)-3-aminobenzenesulfonate Chemical compound C1=C(N)C(NC(=O)NC(=O)C)=CC=C1S(=O)(=O)OC1=CC=CC=C1 UVNDUFUGVWNRIP-UHFFFAOYSA-N 0.000 description 2
OBDGKNCCNSQGPC-UHFFFAOYSA-N phenyl 4-(acetylcarbamoylamino)-3-nitrobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)NC(=O)C)=CC=C1S(=O)(=O)OC1=CC=CC=C1 OBDGKNCCNSQGPC-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
IQXUIDYRTHQTET-UHFFFAOYSA-N 4-amino-3-nitrophenol Chemical compound NC1=CC=C(O)C=C1[N+]([O-])=O IQXUIDYRTHQTET-UHFFFAOYSA-N 0.000 description 1
SEWNAJIUKSTYOP-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=CC=C1Cl SEWNAJIUKSTYOP-UHFFFAOYSA-N 0.000 description 1
241001147657 Ancylostoma Species 0.000 description 1
241000244186 Ascaris Species 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
241001126268 Cooperia Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000242711 Fasciola hepatica 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
241000243789 Metastrongyloidea Species 0.000 description 1
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000244174 Strongyloides Species 0.000 description 1
241000242541 Trematoda Species 0.000 description 1
241000243797 Trichostrongylus Species 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
FBDPJMGDZLLRNZ-UHFFFAOYSA-N [4-(acetylcarbamoylamino)-3-nitrophenyl] 3-(trifluoromethyl)benzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)NC(=O)C)=CC=C1OS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 FBDPJMGDZLLRNZ-UHFFFAOYSA-N 0.000 description 1
QMAOHNMMWCBEDB-UHFFFAOYSA-N [4-(chlorosulfonylcarbamoylamino)-3-nitrophenyl] 3-(trifluoromethyl)benzenesulfonate Chemical compound C1=C(NC(=O)NS(Cl)(=O)=O)C([N+](=O)[O-])=CC(OS(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)=C1 QMAOHNMMWCBEDB-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 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
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 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
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
125000004093 cyano group Chemical group *C#N 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
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
208000006275 fascioliasis Diseases 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
239000008187 granular material Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
244000144972 livestock Species 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
KHBXLYPOXVQKJG-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-methylsulfanylmethylidene]carbamate Chemical compound COC(=O)NC(SC)=NC(=O)OC KHBXLYPOXVQKJG-UHFFFAOYSA-N 0.000 description 1
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000006072 paste Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
GTQKFVRTZFWEBC-UHFFFAOYSA-N phenyl 3-[[(z)-n,n'-bis(methoxycarbonyl)carbamimidoyl]amino]-4-(carbamoylamino)benzenesulfonate Chemical compound C1=C(NC(N)=O)C(NC(NC(=O)OC)=NC(=O)OC)=CC(S(=O)(=O)OC=2C=CC=CC=2)=C1 GTQKFVRTZFWEBC-UHFFFAOYSA-N 0.000 description 1
BNXKFGPXKCNHMD-UHFFFAOYSA-N phenyl 4-(acetylcarbamoylamino)-3-(methoxycarbonylcarbamothioylamino)benzenesulfonate Chemical compound C1=C(NC(=O)NC(C)=O)C(NC(=S)NC(=O)OC)=CC(S(=O)(=O)OC=2C=CC=CC=2)=C1 BNXKFGPXKCNHMD-UHFFFAOYSA-N 0.000 description 1
CSWATSLUQPFDDW-UHFFFAOYSA-N phenyl 4-(carbamoylamino)-3-(methoxycarbonylcarbamothioylamino)benzenesulfonate Chemical compound C1=C(NC(N)=O)C(NC(=S)NC(=O)OC)=CC(S(=O)(=O)OC=2C=CC=CC=2)=C1 CSWATSLUQPFDDW-UHFFFAOYSA-N 0.000 description 1
JXBMHGKZPCOWBL-UHFFFAOYSA-N phenyl 4-(chlorosulfonylcarbamoylamino)-3-nitrobenzenesulfonate Chemical compound C1=C(NC(=O)NS(Cl)(=O)=O)C([N+](=O)[O-])=CC(S(=O)(=O)OC=2C=CC=CC=2)=C1 JXBMHGKZPCOWBL-UHFFFAOYSA-N 0.000 description 1
NEZIKMJTIOLUGU-UHFFFAOYSA-N phenyl 4-amino-3-nitrobenzenesulfonate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1S(=O)(=O)OC1=CC=CC=C1 NEZIKMJTIOLUGU-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
BYTCDABWEGFPLT-UHFFFAOYSA-L potassium;sodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[K+] BYTCDABWEGFPLT-UHFFFAOYSA-L 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 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
238000010583 slow cooling Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
235000010384 tocopherol Nutrition 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
150000003626 triacylglycerols Chemical class 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
239000008096 xylene Substances 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
- 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
- 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
- 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
- C07C309/76—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
- C07C323/66—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfo, esterified sulfo or halosulfonyl groups, bound to the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/24—Derivatives of thiourea containing any of the groups, X being a hetero atom, Y being any atom
- C07C335/28—Y being a hetero atom, e.g. thiobiuret

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Medicinal Preparation (AREA)

NO833158A 1982-09-04 1983-09-02 Substituerte benzensulfonsyreestere, fremgangsmaate til deres fremstilling og deres anvendelse som legemiddel NO833158L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19823232959 DE3232959A1 (de)	1982-09-04	1982-09-04	Substituierte benzolsulfonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel

Publications (1)

Publication Number	Publication Date
NO833158L true NO833158L (no)	1984-03-05

Family

ID=6172503

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO833158A NO833158L (no)	1982-09-04	1983-09-02	Substituerte benzensulfonsyreestere, fremgangsmaate til deres fremstilling og deres anvendelse som legemiddel

Country Status (20)

Country	Link
US (1)	US4504490A (da)
EP (1)	EP0105196B1 (da)
JP (1)	JPS5976050A (da)
KR (1)	KR840006335A (da)
AT (1)	ATE28630T1 (da)
AU (1)	AU1867983A (da)
CA (1)	CA1214182A (da)
DE (2)	DE3232959A1 (da)
DK (1)	DK401683A (da)
ES (2)	ES525335A0 (da)
FI (1)	FI833119A (da)
GR (1)	GR78941B (da)
HU (1)	HU193531B (da)
IL (1)	IL69640A0 (da)
MA (1)	MA19892A1 (da)
NO (1)	NO833158L (da)
NZ (1)	NZ205468A (da)
PH (1)	PH19980A (da)
PT (1)	PT77285B (da)
ZA (1)	ZA836515B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3713856A1 (de) *	1987-04-25	1988-11-17	Bayer Ag	Sulfonsaeurearylesterhaltige aromatische diamine, ein verfahren zu ihrer herstellung sowie ihre verwendung bei der herstellung von polyurethankunststoffen
SE9103745D0 (sv) *	1991-12-18	1991-12-18	Wikstroem Haakan	Aryl-triflates and related compounds
EP0742208A1 (en) *	1995-05-05	1996-11-13	Grelan Pharmaceutical Co., Ltd.	2-Ureido-benzamide derivatives
ES2394211T3 (es)	2000-06-20	2013-01-23	Novartis Ag	Procedimiento de administración de bifosfonatos
WO2012142698A1 (en) *	2011-04-20	2012-10-26	Universite Laval	Alkylurea derivatives active against cancer cells
DE102020112411B3 (de) *	2020-05-07	2021-05-27	Papierfabrik August Koehler Se	Wärmeempfindliches Aufzeichnungsmaterial

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
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

1982
- 1982-09-04 DE DE19823232959 patent/DE3232959A1/de not_active Withdrawn
1983
- 1983-08-31 EP EP83108570A patent/EP0105196B1/de not_active Expired
- 1983-08-31 DE DE8383108570T patent/DE3372756D1/de not_active Expired
- 1983-08-31 AT AT83108570T patent/ATE28630T1/de not_active IP Right Cessation
- 1983-09-01 FI FI833119A patent/FI833119A/fi not_active Application Discontinuation
- 1983-09-02 HU HU833068A patent/HU193531B/hu unknown
- 1983-09-02 GR GR72361A patent/GR78941B/el unknown
- 1983-09-02 KR KR1019830004133A patent/KR840006335A/ko not_active Application Discontinuation
- 1983-09-02 JP JP58160602A patent/JPS5976050A/ja active Pending
- 1983-09-02 US US06/528,842 patent/US4504490A/en not_active Expired - Fee Related
- 1983-09-02 NO NO833158A patent/NO833158L/no unknown
- 1983-09-02 IL IL69640A patent/IL69640A0/xx unknown
- 1983-09-02 DK DK401683A patent/DK401683A/da not_active Application Discontinuation
- 1983-09-02 ZA ZA836515A patent/ZA836515B/xx unknown
- 1983-09-02 ES ES525335A patent/ES525335A0/es active Granted
- 1983-09-02 PH PH29485A patent/PH19980A/en unknown
- 1983-09-02 AU AU18679/83A patent/AU1867983A/en not_active Abandoned
- 1983-09-02 PT PT77285A patent/PT77285B/pt unknown
- 1983-09-02 CA CA000435946A patent/CA1214182A/en not_active Expired
- 1983-09-02 NZ NZ205468A patent/NZ205468A/xx unknown
- 1983-09-03 MA MA20115A patent/MA19892A1/fr unknown
1984
- 1984-07-02 ES ES533932A patent/ES533932A0/es active Granted

Also Published As

Publication number	Publication date
DK401683A (da)	1984-03-05
AU1867983A (en)	1984-03-08
CA1214182A (en)	1986-11-18
IL69640A0 (en)	1983-12-30
FI833119A (fi)	1984-03-05
ZA836515B (en)	1984-04-25
GR78941B (da)	1984-10-02
ES8503649A1 (es)	1985-03-16
PH19980A (en)	1986-08-26
KR840006335A (ko)	1984-11-29
DK401683D0 (da)	1983-09-02
ES8500898A1 (es)	1984-11-01
US4504490A (en)	1985-03-12
DE3372756D1 (en)	1987-09-03
ES533932A0 (es)	1985-03-16
ATE28630T1 (de)	1987-08-15
EP0105196A2 (de)	1984-04-11
EP0105196B1 (de)	1987-07-29
HU193531B (en)	1987-10-28
MA19892A1 (fr)	1984-04-01
PT77285A (en)	1983-10-01
EP0105196A3 (en)	1985-04-03
JPS5976050A (ja)	1984-04-28
NZ205468A (en)	1985-07-31
ES525335A0 (es)	1984-11-01
PT77285B (en)	1986-04-09
FI833119A0 (fi)	1983-09-01
DE3232959A1 (de)	1984-03-08

Publication	Publication Date	Title
US3954791A (en)	1976-05-04	Anthelmintically active 2-carbalkoxy-amino-benzimidazole-5(6)-phenyl ethers
US3929821A (en)	1975-12-30	5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives
CS201522B2 (en)	1980-11-28	Process for preparing benzimidazolcarbamates
KR910000045B1 (ko)	1991-01-19	치환된 페닐설포닐옥시벤즈이미다졸 카바메이트의 제조방법
US4002640A (en)	1977-01-11	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
JPS5915904B2 (ja)	1984-04-12	置換フエニルグアニジンの製造方法
US3773960A (en)	1973-11-20	Acaracidal compositions and methods comprising aliphatically substituted thiosulfinyl-and sulfonyl-alkyl-2,4,5-trihalogeno imidazoles
EP0003951A1 (en)	1979-09-19	Process for the preparation of 2-benzimidazolecarbamic acid esters
NO833158L (no)	1984-03-05	Substituerte benzensulfonsyreestere, fremgangsmaate til deres fremstilling og deres anvendelse som legemiddel
US3996369A (en)	1976-12-07	Anthelmintically active 2-carbalkoxyamino benzimidazolyl-5(6)-sulfonic acid phenyl esters
JPS6254786B2 (da)	1987-11-17
US4021571A (en)	1977-05-03	Substituted phenylisothioureas and processes for their preparation and use
US4575501A (en)	1986-03-11	2-Arylhydrazino-2-thiazolines, acyl derivatives of these compounds, 2-arylazo-2-thiazolines, preparation processes, and their use for combating ectoparasites and endoparasites
CS196278B2 (en)	1980-03-31	Method of producing 2-alkoxycarbonylamino-5/6/-phenylsulphonyl oxybenzimidazoles
US4072696A (en)	1978-02-07	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
US3821276A (en)	1974-06-28	3-cyanobenzenesulfonamides
US4254143A (en)	1981-03-03	Monocarboxylates of phenylguanidinesulfonic acid esters, a process for their manufacture, compositions containing them and their use for combating helminths
US3984561A (en)	1976-10-05	Anthelmintically active 2-carbalkoxy-amino-benzimidazole-5(6)-phenyl ethers and method for using the same
HU180660B (en)	1983-04-29	Process for preparing substituted o-phenylene-diamine derivatives
US4010272A (en)	1977-03-01	Anthelmintically active basically substituted 2-carbalkoxy-amino-benzimidazolyl-5(6)-phenyl ethers and -ketones
US3439033A (en)	1969-04-15	Benzene-sulfonyl ureas
NO770649L (no)	1977-08-30	Substituerte fenylguanidiner og fremgangsm}te til deres fremstilling.
US4080461A (en)	1978-03-21	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
NO843573L (no)	1985-03-11	6-sulfoksyfenolderivater, deres fremstilling og deres anvendelse som cytoprotektiva
CS196284B2 (cs)	1980-03-31	Způsob výroby fenylesterů 2-alkoxykarbonylaminobenzimidazol- -5(B)-ylsulfonové kyseliny