IE41199B1 - 1,5(6)-disubstituted benzimidazole-2-carbamate derivativeshaving anthelmintic activity - Google Patents
1,5(6)-disubstituted benzimidazole-2-carbamate derivativeshaving anthelmintic activityInfo
- Publication number
- IE41199B1 IE41199B1 IE1434/74A IE143474A IE41199B1 IE 41199 B1 IE41199 B1 IE 41199B1 IE 1434/74 A IE1434/74 A IE 1434/74A IE 143474 A IE143474 A IE 143474A IE 41199 B1 IE41199 B1 IE 41199B1
- Authority
- IE
- Ireland
- Prior art keywords
- derivativeshaving
- carbamate
- denotes
- anthelmintic activity
- benzimidazole
- Prior art date
Links
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 title 1
- 230000000507 anthelmentic effect Effects 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- -1 sulphinyl Chemical group 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 210000001035 gastrointestinal tract Anatomy 0.000 abstract 1
- 244000000013 helminth Species 0.000 abstract 1
- 208000015181 infectious disease Diseases 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 244000045947 parasite Species 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Compounds of the formula <IMAGE> wherein R denotes C1-C4-alkyl, R<1> denotes various ether, thioether, sulphinyl and sulphonyl groups and R<8> denotes aryl, aralkyl or C1-C12-alkyl, which can be substituted by (C1-C4-alkoxy)-carbonyl, are prepared by reaction of a corresponding benzimidazole, which is however unsubstituted in the 1-position, with an isocyanate OCNR. The compounds and their salts with acids possess a broad-band activity against parasites of mammals, especially against helminths, and can be used for the treatment of corresponding infections of the digestive tract.
[GB1480722A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US473865A US3929822A (en) | 1972-12-29 | 1974-05-28 | 1,5(6)-Disubstituted benzizimidazole-2-carbamate derivatives having anthelmintic activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41199L IE41199L (en) | 1975-11-28 |
| IE41199B1 true IE41199B1 (en) | 1979-11-07 |
Family
ID=23881335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1434/74A IE41199B1 (en) | 1974-05-28 | 1974-07-05 | 1,5(6)-disubstituted benzimidazole-2-carbamate derivativeshaving anthelmintic activity |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS50155612A (en) |
| AR (1) | AR221575A1 (en) |
| AT (1) | AT337714B (en) |
| BE (1) | BE817164Q (en) |
| BR (1) | BR7406197A (en) |
| CH (1) | CH614943A5 (en) |
| CS (1) | CS222211B2 (en) |
| DD (1) | DD115494A6 (en) |
| DE (1) | DE2431093C2 (en) |
| DK (1) | DK155005C (en) |
| ES (1) | ES430794A1 (en) |
| GB (1) | GB1480722A (en) |
| HU (1) | HU169779B (en) |
| IE (1) | IE41199B1 (en) |
| IT (1) | IT1046279B (en) |
| PL (1) | PL100057B1 (en) |
| RO (1) | RO64921A (en) |
| SE (1) | SE414174B (en) |
| SU (1) | SU644385A3 (en) |
| YU (1) | YU37331B (en) |
| ZA (2) | ZA746665B (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3578676A (en) * | 1968-06-21 | 1971-05-11 | Smith Kline French Lab | Benzimidazole-2-carbamates substituted on the benzene ring with an acyloxyalkyl group |
| US3722322A (en) * | 1971-05-05 | 1973-03-27 | E Coeppert | Speed control device |
| BE793358A (en) * | 1971-12-27 | 1973-06-27 | Hoechst Ag | NEW 2-CARBALCOXY-AMINO-BENZIMIDAZOLE DERIVATIVES PRESENTING ANTHELMINTIC ACTIVITY AND THEIR PREPARATION PROCESS |
-
1974
- 1974-05-28 RO RO74473865A patent/RO64921A/en unknown
- 1974-06-19 SE SE7408108A patent/SE414174B/en not_active IP Right Cessation
- 1974-06-26 JP JP49073160A patent/JPS50155612A/ja active Pending
- 1974-06-27 CS CS744553A patent/CS222211B2/en unknown
- 1974-06-27 YU YU1813/74A patent/YU37331B/en unknown
- 1974-06-28 DE DE2431093A patent/DE2431093C2/en not_active Expired
- 1974-06-28 DK DK351774A patent/DK155005C/en not_active IP Right Cessation
- 1974-07-02 BE BE146141A patent/BE817164Q/en not_active IP Right Cessation
- 1974-07-03 GB GB29574/74A patent/GB1480722A/en not_active Expired
- 1974-07-05 AT AT556274A patent/AT337714B/en not_active IP Right Cessation
- 1974-07-05 IE IE1434/74A patent/IE41199B1/en unknown
- 1974-07-09 DD DD179816A patent/DD115494A6/xx unknown
- 1974-07-12 CH CH967674A patent/CH614943A5/en not_active IP Right Cessation
- 1974-07-19 SU SU742047767A patent/SU644385A3/en active
- 1974-07-26 BR BR6197/74A patent/BR7406197A/en unknown
- 1974-08-09 HU HUSI1425A patent/HU169779B/hu unknown
- 1974-08-20 PL PL1974173572A patent/PL100057B1/en unknown
- 1974-10-08 ES ES430794A patent/ES430794A1/en not_active Expired
- 1974-10-21 ZA ZA00746665A patent/ZA746665B/en unknown
- 1974-10-21 ZA ZA00746666A patent/ZA746666B/en unknown
- 1974-10-25 IT IT70183/74A patent/IT1046279B/en active
-
1981
- 1981-07-18 AR AR254768A patent/AR221575A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AR221575A1 (en) | 1981-02-27 |
| BE817164Q (en) | 1975-01-02 |
| SE7408108L (en) | 1975-12-01 |
| DE2431093A1 (en) | 1975-12-11 |
| ATA556274A (en) | 1976-11-15 |
| HU169779B (en) | 1977-02-28 |
| DK351774A (en) | 1975-11-29 |
| PL100057B1 (en) | 1978-08-31 |
| IE41199L (en) | 1975-11-28 |
| DD115494A6 (en) | 1975-10-05 |
| CS222211B2 (en) | 1983-05-27 |
| SE414174B (en) | 1980-07-14 |
| YU37331B (en) | 1984-08-31 |
| BR7406197A (en) | 1976-03-23 |
| SU644385A3 (en) | 1979-01-25 |
| ZA746665B (en) | 1976-05-26 |
| YU181374A (en) | 1983-04-27 |
| CH614943A5 (en) | 1979-12-28 |
| ZA746666B (en) | 1976-06-30 |
| IT1046279B (en) | 1980-06-30 |
| DK155005B (en) | 1989-01-23 |
| RO64921A (en) | 1979-07-15 |
| DK155005C (en) | 1989-06-05 |
| AT337714B (en) | 1977-07-11 |
| DE2431093C2 (en) | 1982-12-02 |
| JPS50155612A (en) | 1975-12-16 |
| ES430794A1 (en) | 1977-08-01 |
| GB1480722A (en) | 1977-07-20 |
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