DE2541751A1 - Anthelminthisch wirksame 2-carbalkoxyamino-benzimidazolderivate und verfahren zu ihrer herstellung - Google Patents
Anthelminthisch wirksame 2-carbalkoxyamino-benzimidazolderivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2541751A1 DE2541751A1 DE19752541751 DE2541751A DE2541751A1 DE 2541751 A1 DE2541751 A1 DE 2541751A1 DE 19752541751 DE19752541751 DE 19752541751 DE 2541751 A DE2541751 A DE 2541751A DE 2541751 A1 DE2541751 A1 DE 2541751A1
- Authority
- DE
- Germany
- Prior art keywords
- carbomethoxyamino
- benzothiadiazine
- benzimidazole
- phenylsulfonyloxy
- sulfonic acid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical compound NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 title abstract 2
- 230000000507 anthelmentic effect Effects 0.000 title description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- NLXPDNKIQMAKCH-UHFFFAOYSA-N 1h-2,1,4-benzothiadiazine Chemical class C1=CC=C2NSC=NC2=C1 NLXPDNKIQMAKCH-UHFFFAOYSA-N 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 2
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 241000282849 Ruminantia Species 0.000 abstract description 2
- HJYCUXWTLGRKBZ-UHFFFAOYSA-N phenyl 3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazine-7-sulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1 HJYCUXWTLGRKBZ-UHFFFAOYSA-N 0.000 abstract 1
- -1 phenylthio radicals Chemical class 0.000 description 63
- 239000002904 solvent Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000007658 benzothiadiazines Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 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
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 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
- 229940126601 medicinal product Drugs 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VPCGFIDDGFNWSY-UHFFFAOYSA-N (3-bromophenyl) 3H-benzimidazole-5-sulfonate Chemical compound BrC=1C=C(C=CC=1)OS(=O)(=O)C=1C=CC2=C(N=CN2)C=1 VPCGFIDDGFNWSY-UHFFFAOYSA-N 0.000 description 1
- ZTIZECMIEROXDK-UHFFFAOYSA-N (3-chlorophenyl) 3H-benzimidazole-5-sulfonate Chemical compound ClC=1C=C(C=CC=1)OS(=O)(=O)C=1C=CC2=C(N=CN2)C=1 ZTIZECMIEROXDK-UHFFFAOYSA-N 0.000 description 1
- HXSGBHMVABLFOO-UHFFFAOYSA-N (3-ethoxyphenyl) 3H-benzimidazole-5-sulfonate Chemical compound C(C)OC=1C=C(C=CC=1)OS(=O)(=O)C=1C=CC2=C(N=CN2)C=1 HXSGBHMVABLFOO-UHFFFAOYSA-N 0.000 description 1
- KNZKWHSJCMNFPD-UHFFFAOYSA-N (3-methylphenyl) 3H-benzimidazole-5-sulfonate Chemical compound CC=1C=C(C=CC=1)OS(=O)(=O)C=1C=CC2=C(N=CN2)C=1 KNZKWHSJCMNFPD-UHFFFAOYSA-N 0.000 description 1
- KNXDZAPQKQUFOR-UHFFFAOYSA-N (4-chlorophenyl) 3H-benzimidazole-5-sulfonate Chemical compound ClC1=CC=C(C=C1)OS(=O)(=O)C=1C=CC2=C(N=CN2)C=1 KNXDZAPQKQUFOR-UHFFFAOYSA-N 0.000 description 1
- ZAUIALFCIFDRCF-UHFFFAOYSA-N (4-methoxyphenyl) 3H-benzimidazole-5-sulfonate Chemical compound COC1=CC=C(C=C1)OS(=O)(=O)C=1C=CC2=C(N=CN2)C=1 ZAUIALFCIFDRCF-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- UYWWLYCGNNCLKE-UHFFFAOYSA-N 2-pyridin-4-yl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1C1=CC=NC=C1 UYWWLYCGNNCLKE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- SOHKAEOPAXDSEF-UHFFFAOYSA-N C(#N)C=1C=C(C=CC=1)OS(=O)(=O)C=1C=CC2=C(N=CN2)C=1 Chemical compound C(#N)C=1C=C(C=CC=1)OS(=O)(=O)C=1C=CC2=C(N=CN2)C=1 SOHKAEOPAXDSEF-UHFFFAOYSA-N 0.000 description 1
- 241000893172 Chabertia Species 0.000 description 1
- VNFFPKLQCGNVRV-UHFFFAOYSA-N ClC=1C=C(C=C(C1)Cl)OS(=O)(=O)C=1C=CC2=C(N=CN2)C1 Chemical compound ClC=1C=C(C=C(C1)Cl)OS(=O)(=O)C=1C=CC2=C(N=CN2)C1 VNFFPKLQCGNVRV-UHFFFAOYSA-N 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- 241001547406 Hyostrongylus Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000244174 Strongyloides Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- KNSMAFVMAGPLCD-UHFFFAOYSA-N [3-(ethoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 3-(trifluoromethyl)benzenesulfonate Chemical compound C1=C2NSC(NC(=O)OCC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 KNSMAFVMAGPLCD-UHFFFAOYSA-N 0.000 description 1
- ILOHHNAACFCVAK-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 2-bromobenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC=C1Br ILOHHNAACFCVAK-UHFFFAOYSA-N 0.000 description 1
- LPGZJNUYYNQUCX-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 3,4-dichlorobenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 LPGZJNUYYNQUCX-UHFFFAOYSA-N 0.000 description 1
- HVFXVOVOJMJPDT-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 3-(trifluoromethyl)benzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 HVFXVOVOJMJPDT-UHFFFAOYSA-N 0.000 description 1
- HKWQGXDTMYTNLD-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 3-bromobenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC(Br)=C1 HKWQGXDTMYTNLD-UHFFFAOYSA-N 0.000 description 1
- OAXIPAMEOHCMKW-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 3-chlorobenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC(Cl)=C1 OAXIPAMEOHCMKW-UHFFFAOYSA-N 0.000 description 1
- HFXWMGNCZMWMRA-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 3-methylbenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC(C)=C1 HFXWMGNCZMWMRA-UHFFFAOYSA-N 0.000 description 1
- LKUIZYHKNRHFFZ-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 4-chlorobenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 LKUIZYHKNRHFFZ-UHFFFAOYSA-N 0.000 description 1
- YDGFFNOSUYVGSL-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 4-methylbenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(C)C=C1 YDGFFNOSUYVGSL-UHFFFAOYSA-N 0.000 description 1
- MWPQFRBSPKPQEU-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] benzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC=C1 MWPQFRBSPKPQEU-UHFFFAOYSA-N 0.000 description 1
- USQXMRHUAONQBW-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 3-(trifluoromethyl)benzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC(C)C)=NC2=CC=C1OS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 USQXMRHUAONQBW-UHFFFAOYSA-N 0.000 description 1
- LVDPNYSFWWAVIO-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl] 3H-benzimidazole-5-sulfonate Chemical compound FC(C=1C=C(C=CC=1)OS(=O)(=O)C=1C=CC2=C(N=CN2)C=1)(F)F LVDPNYSFWWAVIO-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 239000002246 antineoplastic 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
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004429 atom 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 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
- 229940127089 cytotoxic agent Drugs 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 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
- 125000005843 halogen group Chemical group 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste 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
- JMVOTQMMWZCLEX-UHFFFAOYSA-N phenyl 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1 JMVOTQMMWZCLEX-UHFFFAOYSA-N 0.000 description 1
- UEFFJHDCCRVOJW-UHFFFAOYSA-N phenyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC(C)(C)C)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1 UEFFJHDCCRVOJW-UHFFFAOYSA-N 0.000 description 1
- XDXVJSNZLFEGAE-UHFFFAOYSA-N phenyl 3h-benzimidazole-5-sulfonate Chemical compound C=1C=C2N=CNC2=CC=1S(=O)(=O)OC1=CC=CC=C1 XDXVJSNZLFEGAE-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000008334 thiadiazines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
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- 235000010384 tocopherol Nutrition 0.000 description 1
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- 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
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752541751 DE2541751A1 (de) | 1975-09-19 | 1975-09-19 | Anthelminthisch wirksame 2-carbalkoxyamino-benzimidazolderivate und verfahren zu ihrer herstellung |
| EG76551A EG12507A (en) | 1975-09-19 | 1976-09-11 | Process for the preparation of anthelminticially active 2-varbalkoxyamino benzimidazol derivatives |
| ES451512A ES451512A1 (es) | 1975-09-19 | 1976-09-14 | Procedimiento para la preparacion de derivados de 2-carba- leoxiamino-bencimidazul. |
| NL7610191A NL7610191A (nl) | 1975-09-19 | 1976-09-14 | Werkwijze voor het bereiden van anthelmintisch werkzame 2-carb-alkoxy-benzimidazoolderivaten. |
| MX764928U MX3567E (es) | 1975-09-19 | 1976-09-14 | Procedimiento para preparar derivados de 2-carboalcoxi-amino-benci-midazol |
| FI762654A FI762654A7 (enrdf_load_stackoverflow) | 1975-09-19 | 1976-09-16 | |
| HU76HO00001928A HU172248B (hu) | 1975-09-19 | 1976-09-16 | Sposob poluchenija 2-karbalkoksiamino-proizvodnykh benzimidazola s antgel'-minticheskim ehffektom |
| SE7610311A SE7610311L (sv) | 1975-09-19 | 1976-09-16 | Forfarande for framstellning av anthelmintiskt verksamma 2-karbalkoxyaminobensimidazolderivat |
| LU75816A LU75816A1 (enrdf_load_stackoverflow) | 1975-09-19 | 1976-09-16 | |
| AT690976A AT356651B (de) | 1975-09-19 | 1976-09-17 | Verfahren zur herstellung von neuen 2-car- balkoxyamino-benzimidazolderivaten |
| NO763197A NO763197L (no) | 1975-09-19 | 1976-09-17 | Fremgangsm}te til fremstilling av antelmintisk virksomme 2-karbalkoksyamino-benzimidazolderivater. |
| DK419976A DK419976A (da) | 1975-09-19 | 1976-09-17 | Fremgangsmade til fremstilling af anthelmintisk virksomme 2-carbalkoxyamino-benzimidazolderivater |
| CH1182276A CH605822A5 (enrdf_load_stackoverflow) | 1975-09-19 | 1976-09-17 | |
| PT65608A PT65608B (de) | 1975-09-19 | 1976-09-17 | Verfahren zur herstellung von anthelmintisch wirksamen 2-carbalkoxyamino-benzimidazolderivaten |
| CA261,424A CA1069908A (en) | 1975-09-19 | 1976-09-17 | Process for the preparation of anthelmintically active 2-carbalkoxyamino-benzimidazole derivatives |
| GR51722A GR70297B (enrdf_load_stackoverflow) | 1975-09-19 | 1976-09-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752541751 DE2541751A1 (de) | 1975-09-19 | 1975-09-19 | Anthelminthisch wirksame 2-carbalkoxyamino-benzimidazolderivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2541751A1 true DE2541751A1 (de) | 1977-03-24 |
Family
ID=5956861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752541751 Pending DE2541751A1 (de) | 1975-09-19 | 1975-09-19 | Anthelminthisch wirksame 2-carbalkoxyamino-benzimidazolderivate und verfahren zu ihrer herstellung |
Country Status (16)
-
1975
- 1975-09-19 DE DE19752541751 patent/DE2541751A1/de active Pending
-
1976
- 1976-09-11 EG EG76551A patent/EG12507A/xx active
- 1976-09-14 MX MX764928U patent/MX3567E/es unknown
- 1976-09-14 ES ES451512A patent/ES451512A1/es not_active Expired
- 1976-09-14 NL NL7610191A patent/NL7610191A/xx not_active Application Discontinuation
- 1976-09-16 FI FI762654A patent/FI762654A7/fi not_active Application Discontinuation
- 1976-09-16 HU HU76HO00001928A patent/HU172248B/hu unknown
- 1976-09-16 SE SE7610311A patent/SE7610311L/xx unknown
- 1976-09-16 LU LU75816A patent/LU75816A1/xx unknown
- 1976-09-17 NO NO763197A patent/NO763197L/no unknown
- 1976-09-17 CA CA261,424A patent/CA1069908A/en not_active Expired
- 1976-09-17 CH CH1182276A patent/CH605822A5/xx not_active IP Right Cessation
- 1976-09-17 DK DK419976A patent/DK419976A/da not_active Application Discontinuation
- 1976-09-17 AT AT690976A patent/AT356651B/de not_active IP Right Cessation
- 1976-09-17 PT PT65608A patent/PT65608B/pt unknown
- 1976-09-18 GR GR51722A patent/GR70297B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR70297B (enrdf_load_stackoverflow) | 1982-09-06 |
| NO763197L (no) | 1977-03-22 |
| DK419976A (da) | 1977-03-20 |
| CH605822A5 (enrdf_load_stackoverflow) | 1978-10-13 |
| AT356651B (de) | 1980-05-12 |
| LU75816A1 (enrdf_load_stackoverflow) | 1977-05-13 |
| SE7610311L (sv) | 1977-03-20 |
| FI762654A7 (enrdf_load_stackoverflow) | 1977-03-20 |
| NL7610191A (nl) | 1977-03-22 |
| MX3567E (es) | 1981-03-13 |
| PT65608A (de) | 1976-10-01 |
| EG12507A (en) | 1978-12-31 |
| CA1069908A (en) | 1980-01-15 |
| PT65608B (de) | 1978-05-10 |
| ES451512A1 (es) | 1977-12-16 |
| ATA690976A (de) | 1979-10-15 |
| HU172248B (hu) | 1978-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |