CA1069909A - Anthelmintically active 2-alkoxycarbonylamino-5(6)-phenyl-sulfonyloxy-benzimidazoles and process for preparing them - Google Patents

Anthelmintically active 2-alkoxycarbonylamino-5(6)-phenyl-sulfonyloxy-benzimidazoles and process for preparing them

Info

Publication number: CA1069909A
Authority: CA; Canada
Prior art keywords: benzimidazole; carbon atoms; methoxycarbonylamino; formula; sulfonic acid
Prior art date: 1975-09-19
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.): Expired

Application number

CA261,425A

Other languages

English (en)

French (fr)

Inventor

Heinz Loewe

Reinhard Kirsch

Dieter Duwel

Josef Urbanietz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

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.)

1975-09-19

Filing date

1976-09-17

Publication date

1980-01-15

1976-09-17 Application filed by Hoechst AG filed Critical Hoechst AG

1980-01-15 Application granted granted Critical

1980-01-15 Publication of CA1069909A publication Critical patent/CA1069909A/en

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title description 2
-1 alkoxy radical Chemical class 0.000 claims abstract description 20
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
238000000034 method Methods 0.000 claims abstract description 11
238000006243 chemical reaction Methods 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
229940092714 benzenesulfonic acid Drugs 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
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
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical class 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
238000002360 preparation method Methods 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000000010 aprotic solvent Substances 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
239000000460 chlorine Chemical group 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Chemical group 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
150000007530 organic bases Chemical group 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
125000001153 fluoro group Chemical group F* 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
241001465754 Metazoa Species 0.000 abstract description 7
244000000013 helminth Species 0.000 abstract description 3
244000045947 parasite Species 0.000 abstract description 3
241000242711 Fasciola hepatica Species 0.000 abstract description 2
239000002246 antineoplastic agent Substances 0.000 abstract description 2
229940127089 cytotoxic agent Drugs 0.000 abstract description 2
201000010099 disease Diseases 0.000 abstract description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
208000006275 fascioliasis Diseases 0.000 abstract description 2
SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000000354 decomposition reaction Methods 0.000 description 12
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
235000013601 eggs Nutrition 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000013543 active substance Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
OINWZUJVEXUHCC-UHFFFAOYSA-N 3-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC(S(Cl)(=O)=O)=C1 OINWZUJVEXUHCC-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-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
229940105329 carboxymethylcellulose Drugs 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003480 eluent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
210000003608 fece Anatomy 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000273 veterinary drug Substances 0.000 description 2
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
FREOGXBZEAMJQN-UHFFFAOYSA-N 2,4-dimethylbenzenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C(C)=C1 FREOGXBZEAMJQN-UHFFFAOYSA-N 0.000 description 1
BXCOSWRSIISQSL-UHFFFAOYSA-N 2,5-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(Cl)C(S(Cl)(=O)=O)=C1 BXCOSWRSIISQSL-UHFFFAOYSA-N 0.000 description 1
QFNSAOSWJSCHID-UHFFFAOYSA-N 2-butylbenzenesulfonic acid Chemical compound CCCCC1=CC=CC=C1S(O)(=O)=O QFNSAOSWJSCHID-UHFFFAOYSA-N 0.000 description 1
JWFLSLOCDIEDGQ-UHFFFAOYSA-N 2-chloro-4-methylbenzenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C(Cl)=C1 JWFLSLOCDIEDGQ-UHFFFAOYSA-N 0.000 description 1
FJVZVTWCAGCLCS-UHFFFAOYSA-N 2-chloro-6-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC(Cl)=C1S(Cl)(=O)=O FJVZVTWCAGCLCS-UHFFFAOYSA-N 0.000 description 1
KMVZDSQHLDGKGV-UHFFFAOYSA-N 2-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC=C1S(Cl)(=O)=O KMVZDSQHLDGKGV-UHFFFAOYSA-N 0.000 description 1
GYOBZOBUOMDRRN-UHFFFAOYSA-N 2-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=CC=C1S(Cl)(=O)=O GYOBZOBUOMDRRN-UHFFFAOYSA-N 0.000 description 1
UYWWLYCGNNCLKE-UHFFFAOYSA-N 2-pyridin-4-yl-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1C1=CC=NC=C1 UYWWLYCGNNCLKE-UHFFFAOYSA-N 0.000 description 1
WIWQDBABYGRKEW-UHFFFAOYSA-N 3,4-dichlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 WIWQDBABYGRKEW-UHFFFAOYSA-N 0.000 description 1
NYIBPWGZGSXURD-UHFFFAOYSA-N 3,4-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1Cl NYIBPWGZGSXURD-UHFFFAOYSA-N 0.000 description 1
RJSQINMKOSOUGT-UHFFFAOYSA-N 3,5-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC(Cl)=CC(S(Cl)(=O)=O)=C1 RJSQINMKOSOUGT-UHFFFAOYSA-N 0.000 description 1
ONCAZCNPWWQQMW-UHFFFAOYSA-N 3-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC(S(Cl)(=O)=O)=C1 ONCAZCNPWWQQMW-UHFFFAOYSA-N 0.000 description 1
PJGOLCXVWIYXRQ-UHFFFAOYSA-N 3-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC(Br)=C1 PJGOLCXVWIYXRQ-UHFFFAOYSA-N 0.000 description 1
JHJKSEKUZNJKGO-UHFFFAOYSA-N 3-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=CC(S(Cl)(=O)=O)=C1 JHJKSEKUZNJKGO-UHFFFAOYSA-N 0.000 description 1
KFPMLWUKHQMEBU-UHFFFAOYSA-N 3-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC(S(Cl)(=O)=O)=C1 KFPMLWUKHQMEBU-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
RRRJSYNMPZCZSU-UHFFFAOYSA-N 4-chloro-2-methylbenzenesulfonic acid Chemical compound CC1=CC(Cl)=CC=C1S(O)(=O)=O RRRJSYNMPZCZSU-UHFFFAOYSA-N 0.000 description 1
IJWCRHKAQNFJLT-UHFFFAOYSA-N 4-propan-2-yloxybenzenesulfonyl chloride Chemical compound CC(C)OC1=CC=C(S(Cl)(=O)=O)C=C1 IJWCRHKAQNFJLT-UHFFFAOYSA-N 0.000 description 1
LHYZGURMLPSRFU-UHFFFAOYSA-N 4-propoxybenzenesulfonyl chloride Chemical compound CCCOC1=CC=C(S(Cl)(=O)=O)C=C1 LHYZGURMLPSRFU-UHFFFAOYSA-N 0.000 description 1
VHBFBNCERXCECQ-UHFFFAOYSA-N 5-chloro-2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=C(Cl)C=C1S(Cl)(=O)=O VHBFBNCERXCECQ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
241000893172 Chabertia Species 0.000 description 1
241001126268 Cooperia 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
241001547406 Hyostrongylus Species 0.000 description 1
206010061217 Infestation Diseases 0.000 description 1
241000510960 Oesophagostomum Species 0.000 description 1
241000243795 Ostertagia Species 0.000 description 1
241000283903 Ovis aries Species 0.000 description 1
241001494479 Pecora Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
241000282849 Ruminantia Species 0.000 description 1
229910006080 SO2X Inorganic materials 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 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
241000243796 Trichostrongylus colubriformis Species 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
230000000507 anthelmentic effect Effects 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
239000007900 aqueous suspension Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 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
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 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
238000005984 hydrogenation reaction Methods 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229940093956 potassium carbonate Drugs 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
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230000036632 reaction speed Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
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239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
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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
238000004809 thin layer chromatography Methods 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA261,425A 1975-09-19 1976-09-17 Anthelmintically active 2-alkoxycarbonylamino-5(6)-phenyl-sulfonyloxy-benzimidazoles and process for preparing them Expired CA1069909A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19752541752 DE2541752A1 (de)	1975-09-19	1975-09-19	Anthelminthisch wirksame 2-carbalkoxyamino-5(6)-phenyl-sulfonyloxy- benzimidazole und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
CA1069909A true CA1069909A (en)	1980-01-15

Family

ID=5956862

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA261,425A Expired CA1069909A (en)	1975-09-19	1976-09-17	Anthelmintically active 2-alkoxycarbonylamino-5(6)-phenyl-sulfonyloxy-benzimidazoles and process for preparing them

Country Status (12)

Country	Link
AT (1)	AT358575B (da)
CA (1)	CA1069909A (da)
CH (1)	CH619938A5 (da)
DE (1)	DE2541752A1 (da)
DK (1)	DK141550C (da)
ES (1)	ES451497A2 (da)
FI (1)	FI762653A7 (da)
GR (1)	GR60799B (da)
HU (1)	HU172484B (da)
NO (1)	NO763196L (da)
PT (1)	PT65607B (da)
SE (1)	SE7610310L (da)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7041668B2 (en)	2001-09-26	2006-05-09	Aventis Pharma S.A.	Substituted benzimidazole compounds and their use for the treatment of cancer
AU2006296468B2 (en) *	2005-09-27	2012-10-18	Aventis Pharma S.A.	Novel benzimidazole and benzothiazole derivatives, method for preparing same, use thereof as drugs, pharmaceutical compositions and novel use in particular as C-Met inhibitors

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4435418A (en) *	1982-12-13	1984-03-06	Smithkline Beckman Corporation	5-Phenylethenylbenzimidazoles
FR2868421B1 (fr)	2004-04-01	2008-08-01	Aventis Pharma Sa	Nouveaux benzothiazoles et leur utilisation comme medicaments

1975
- 1975-09-19 DE DE19752541752 patent/DE2541752A1/de active Pending
1976
- 1976-09-14 ES ES451497A patent/ES451497A2/es not_active Expired
- 1976-09-16 FI FI762653A patent/FI762653A7/fi not_active Application Discontinuation
- 1976-09-16 SE SE7610310A patent/SE7610310L/xx unknown
- 1976-09-16 HU HU76HO00001929A patent/HU172484B/hu unknown
- 1976-09-17 PT PT65607A patent/PT65607B/pt unknown
- 1976-09-17 DK DK419876A patent/DK141550C/da active
- 1976-09-17 NO NO763196A patent/NO763196L/no unknown
- 1976-09-17 CA CA261,425A patent/CA1069909A/en not_active Expired
- 1976-09-17 CH CH1182076A patent/CH619938A5/de not_active IP Right Cessation
- 1976-09-17 AT AT690876A patent/AT358575B/de active
- 1976-09-18 GR GR51724A patent/GR60799B/el unknown

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7041668B2 (en)	2001-09-26	2006-05-09	Aventis Pharma S.A.	Substituted benzimidazole compounds and their use for the treatment of cancer
AU2006296468B2 (en) *	2005-09-27	2012-10-18	Aventis Pharma S.A.	Novel benzimidazole and benzothiazole derivatives, method for preparing same, use thereof as drugs, pharmaceutical compositions and novel use in particular as C-Met inhibitors

Also Published As

Publication number	Publication date
GR60799B (en)	1978-08-30
PT65607A (de)	1976-10-01
DK141550C (da)	1980-10-06
DK141550B (da)	1980-04-21
DK419876A (da)	1977-03-20
NO763196L (no)	1977-03-22
DE2541752A1 (de)	1977-03-24
ATA690876A (de)	1980-02-15
HU172484B (hu)	1978-09-28
ES451497A2 (es)	1977-12-01
PT65607B (de)	1978-05-10
SE7610310L (sv)	1977-03-20
FI762653A7 (da)	1977-03-20
CH619938A5 (en)	1980-10-31
AT358575B (de)	1980-09-25

Legal Events

Date	Code	Title	Description
1997-01-15	MKEX	Expiry

Publication	Publication Date	Title
US3954791A (en)	1976-05-04	Anthelmintically active 2-carbalkoxy-amino-benzimidazole-5(6)-phenyl ethers
JPS5939428B2 (ja)	1984-09-22	駆虫効果を有する５（６）−ベンゼン環置換ベンズイミダゾ−ル−２−カルバメ−ト誘導体の製造方法
US4002640A (en)	1977-01-11	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
CA1069909A (en)	1980-01-15	Anthelmintically active 2-alkoxycarbonylamino-5(6)-phenyl-sulfonyloxy-benzimidazoles and process for preparing them
DK150065B (da)	1986-12-01	Substituerede phenylsulfonyloxybenzimidazolcarbaminater, deres anvendelse imod helminther samt middel til bekaempelse af ormesygdomme
GB2163423A (en)	1986-02-26	Thiobarbituric acid derivatives
US3928375A (en)	1975-12-23	Anthelmintically active 2-carbalkoxy-amino-benzimidazolyl-5(6)-amino-phenyl ethers
CA1059135A (en)	1979-07-24	Anthelmintically active 2-carbalkoxyamino-5 (6)-phenyl sulfonyloxy benzimidazoles and process for their manufacture
US3996369A (en)	1976-12-07	Anthelmintically active 2-carbalkoxyamino benzimidazolyl-5(6)-sulfonic acid phenyl esters
US4010272A (en)	1977-03-01	Anthelmintically active basically substituted 2-carbalkoxy-amino-benzimidazolyl-5(6)-phenyl ethers and -ketones
JPH03120260A (ja)	1991-05-22	置換アントラニル酸誘導体
JPS6216469A (ja)	1987-01-24	２−置換シクロヘプトイミダゾ−ル誘導体、抗潰瘍剤及びその製造方法
US3984561A (en)	1976-10-05	Anthelmintically active 2-carbalkoxy-amino-benzimidazole-5(6)-phenyl ethers and method for using the same
CA1058194A (en)	1979-07-10	Substituted benzenedisulfonamides as anthelmintics
US4161534A (en)	1979-07-17	Process for the production of novel hydroxyalkyl dithiocarbamates
EP0019587B1 (de)	1983-07-20	Neue Carbonsäurehydrazide, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Zusammensetzungen
CA1056828A (en)	1979-06-19	Preparation of 2,1,4-benzothiadiazine derivatives
IE46869B1 (en)	1983-10-19	Anthelmintic benzimidazolecarbamates
US4005199A (en)	1977-01-25	Substituted benzenesulfonamides as anthelmintics
KR790001340B1 (ko)	1979-09-27	2-카보알콕시-아미노-5(6)-페닐-설포닐옥시 벤즈이미다졸류의 제조방법
KR790001341B1 (ko)	1979-09-27	2-카보알콕시아미노 벤즈이미다조릴-5(6)-설폰산 페닐 에스테르류의 제조방법
US4069325A (en)	1978-01-17	3-Carbalkoxyamino-1H-2,1,4-benzothiadiazine derivatives
NO763194L (no)	1977-03-22	Fremgangsm}te til fremstilling av antelmintisk virksomme basisk substituerte 2-karbalkoksyamino-benzimidazolyl-5(6)-fenyletere og -ketoner.
CS196284B2 (cs)	1980-03-31	Způsob výroby fenylesterů 2-alkoxykarbonylaminobenzimidazol- -5(B)-ylsulfonové kyseliny
CS196280B2 (cs)	1980-03-31	Způsob výroby 2-alkoxykarbonylamÍJio-5(6)-íenylsulfonyloxybenziinidazolů

CA1069909A - Anthelmintically active 2-alkoxycarbonylamino-5(6)-phenyl-sulfonyloxy-benzimidazoles and process for preparing them - Google Patents

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Applications Claiming Priority (1)

Publications (1)

Family

ID=5956862

Family Applications (1)

Country Status (12)

Cited By (2)

Families Citing this family (2)

Cited By (2)

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