GB1089853A - Substituted benzimidazoles and compositions containing them - Google Patents
Substituted benzimidazoles and compositions containing themInfo
- Publication number
- GB1089853A GB1089853A GB819365A GB819365A GB1089853A GB 1089853 A GB1089853 A GB 1089853A GB 819365 A GB819365 A GB 819365A GB 819365 A GB819365 A GB 819365A GB 1089853 A GB1089853 A GB 1089853A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- formula
- alkyl
- compound
- alkenyl
- 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.)
- Expired
Links
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
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Compounds of the formula <FORM:1089853/C2/1> wherein R1 is an acyl radical and each of R2 and R3 is a hydrogen atom or a C1- 6 alkyl or C1- 6 alkoxy group, at least one of R2 and R3 being hydrogen and salts thereof and preparation thereof by reacting a compound of the formula <FORM:1089853/C2/2> wherein R2 and R3 have the above significance and Y is -NH2 with 2-naphthaldehyde and treating the resulting compound of the first general formula above wherein R1 is hydrogen with sodium hydride followed by the appropriate acyl halide. In addition there is disclosed the preparation of substituted benzimidazoles of the first formula above, wherein R1 is hydrogen, alkali metal, C1- 6 alkenyl and R2 and R3 have the above significance by reacting a compound of the second general formula above, wherein Y is -NO2, -NH2 or -NH.R1 (wherein R1 is C1- 6 alkyl or C2- 6 alkenyl) with 2-naphthoic acid or the ester, amide, nitrile or halide thereof in the presence of mineral acid (e.g. polyphosphoric or aqueous sulphuric acid) which cyclises the intermediate anilide or with 2-naphthaldehyde in the presence of an oxidizing agent (e.g. nitrobenzene, cupric acetate, lead tetraacetate, mercuric acetate or air) which converts the intermediate Schiff base to the desired product. In cases where Y is -NO2 the intermediate anilide is reductively cyclised, preferably with a metal/acid system (e.g. Zn/HCl, Zn/HOAc, Fe/HX or Sn/HX). The N-substituted benzimidazoles are obtained by treating compounds of the first formula above wherein R1 is hydrogen with sodium hydride and reacting the resulting alkali metal salt with alkyl, alkenyl or acyl halides. The preparation of 1-methyl-, 1-allyl-, 1-acetyl-, 1-benzoyl-, 5(6)-methyl- and 5(6)-methoxy-substituted 2 - (21 - naphthyl) - benzimidazoles is described.ALSO:Pharmaceutical compositions suitable for oral administration in the veterinary treatment and prophylaxis of helminthiasis, particularly infestations with blood-sucking nematodes such as whipworms and hook-worms, comprise a compound of the formula: <FORM:1089853/A5-A6/1> wherein R1 is hydrogen or alkali metal atom or a C1-6 alkyl, C2-6 alkenyl or acyl radical and each of R2 and R3 being hydrogen, or a C1-6 alkyl or C1-6 alkoxy group, at least one of R2 and R3 being hydrogen, or an acid addition salt thereof, intimately dispersed in or admixed with specified vehicles such as a non-toxic liquid carrier or diluent containing a suspending or dispersing agent or a non-toxic solid carrier or diluent. The compositions may be in unit dosage forms such as a capsule, tablet, bolus or drench containing 5-70% by weight of the active compound or in the form of an animal feed supplement containing 5-50% by weight of the active compound. Compounds of the above formula wherein R1 is acyl may also be used in drinking water.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB819365A GB1089853A (en) | 1965-02-25 | 1965-02-25 | Substituted benzimidazoles and compositions containing them |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB819365A GB1089853A (en) | 1965-02-25 | 1965-02-25 | Substituted benzimidazoles and compositions containing them |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1089853A true GB1089853A (en) | 1967-11-08 |
Family
ID=9847642
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB819365A Expired GB1089853A (en) | 1965-02-25 | 1965-02-25 | Substituted benzimidazoles and compositions containing them |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1089853A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0209707A2 (en) * | 1985-06-21 | 1987-01-28 | Dr. Karl Thomae GmbH | 2-Aryl imidazoles, pharmaceutical compositions containing them and process for their preparation |
US9226489B2 (en) | 2011-03-18 | 2016-01-05 | Ecolab Usa Inc. | Heat system for killing pests |
-
1965
- 1965-02-25 GB GB819365A patent/GB1089853A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0209707A2 (en) * | 1985-06-21 | 1987-01-28 | Dr. Karl Thomae GmbH | 2-Aryl imidazoles, pharmaceutical compositions containing them and process for their preparation |
EP0209707A3 (en) * | 1985-06-21 | 1989-02-01 | Dr. Karl Thomae GmbH | 2-aryl imidazoles, pharmaceutical compositions containing them and process for their preparation |
US9226489B2 (en) | 2011-03-18 | 2016-01-05 | Ecolab Usa Inc. | Heat system for killing pests |
US10070639B2 (en) | 2011-03-18 | 2018-09-11 | Ecolab Usa Inc. | Heat system for killing pests |
US11013226B2 (en) | 2011-03-18 | 2021-05-25 | Ecolab Usa Inc. | Heat system for killing pests |
US11737445B2 (en) | 2011-03-18 | 2023-08-29 | Ecolab Usa Inc. | Heat system for killing pests |
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