GB955961A - Benzimidazole derivatives - Google Patents

Benzimidazole derivatives

Info

Publication number
GB955961A
GB955961A GB3249359A GB3249359A GB955961A GB 955961 A GB955961 A GB 955961A GB 3249359 A GB3249359 A GB 3249359A GB 3249359 A GB3249359 A GB 3249359A GB 955961 A GB955961 A GB 955961A
Authority
GB
United Kingdom
Prior art keywords
benzimidazole
methyl
ethyl
cyano
group
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
Application number
GB3249359A
Inventor
Henri Depoorter
Gerrit Godfried Van Mierlo
Marcel Jan Libeer
Jean Marienys
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.)
Gevaert Photo Producten NV
Original Assignee
Gevaert Photo Producten NV
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.)
Filing date
Publication date
Application filed by Gevaert Photo Producten NV filed Critical Gevaert Photo Producten NV
Priority to GB3249359A priority Critical patent/GB955961A/en
Priority to FR839383A priority patent/FR1273062A/en
Priority to BE595327A priority patent/BE595327A/en
Publication of GB955961A publication Critical patent/GB955961A/en
Expired legal-status Critical Current

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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises benzimidazole derivatives of the general formula: <FORM:0955961/C2/1> in which R1 is a lower alkyl group or an acyloxy-alkylene group, R2 is a methyl group and R3, R4 and R5 each represents a hydrogen atom, a chlorine atom, a bromine atom, a fluorine atom, a carbalkoxy group, a cyano group, an amino group, a nitro group or a phenyl group, at least one of the radicals R3, R4 and R5 representing a fluorine atom, a carbalkoxy group, a cyano group or a phenyl group. The compounds may be made by reducing and cyclising o-nitroaniline or o-nitroacetanilide derivatives carrying the above specified substituents. The reduction of the nitro group is carried out, e.g. by treatment with hydrogen under pressure in the presence of Raney nickel. The cyclisation of the amino compound produced may be effected by treatment with acetic acid. The reduction and cyclisation may be carried out in one step by using a reducing agent such as stannous chloride or metallic zinc in the presence of hydrochloric acid and acetic acid. Alternatively, the benzimidazole derivatives containing a fluoro-, a chloro- or a cyano-substituent may be made by diazotizing the corresponding benzimidazole compounds and treating them by known methods to convert the diazonium compound to the corresponding fluoro-, chloro, or cyano benzimidazoles. Examples are given of the preparation of (a) 1-ethyl -2- methyl -5- phenyl benzimidazole; (b) 1-ethyl -2-methyl -5- fluoro benzimidazole; (c) 1-ethyl -2- methyl- -5- chloro -6- fluoro benzimidazole; (d) 1-ethyl -2- methyl -5- fluoro-6- nitro benzimidazole; (e) 1-ethyl -2- methyl -5-fluoro -6- amino benzimidazole; (f) 1-ethyl 1-2-methyl -5- fluoro -6- chloro benzimidazole; (g) 1-ethyl -2- methyl -5- cyano benzimidazole; (h) 1-ethyl -2- methyl -5- chloro -6- cyano benzimidazole; (j) 1-ethyl -2- methyl -5- fluoro -6-cyano benzimidazole; (k) 1-ethyl -2- methyl -6-cyano benzimidazole; (l) 1-ethyl -2- methyl -7-cyano benzimidazole; (m) 1-(b -acetoxyethyl)-2-methyl -5- cyano benzimidazole; and (n) 1-ethyl -2- methyl -7- carbethoxy benzimidazole. Specification 955,962 is referred to.
GB3249359A 1959-09-24 1959-09-24 Benzimidazole derivatives Expired GB955961A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB3249359A GB955961A (en) 1959-09-24 1959-09-24 Benzimidazole derivatives
FR839383A FR1273062A (en) 1959-09-24 1960-09-23 Benzimidazole derivatives
BE595327A BE595327A (en) 1959-09-24 1960-09-23 Benzimidazole Derivatives.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3249359A GB955961A (en) 1959-09-24 1959-09-24 Benzimidazole derivatives

Publications (1)

Publication Number Publication Date
GB955961A true GB955961A (en) 1964-04-22

Family

ID=10339442

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3249359A Expired GB955961A (en) 1959-09-24 1959-09-24 Benzimidazole derivatives

Country Status (2)

Country Link
BE (1) BE595327A (en)
GB (1) GB955961A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3448171A (en) * 1966-09-06 1969-06-03 Wyandotte Chemicals Corp High molecular weight urethane polymers having an ordered arrangement of pendant unsaturation and process for their production
JP2015516977A (en) * 2012-04-20 2015-06-18 メリアル リミテッド Parasiticidal compositions containing benzimidazole derivatives, methods and uses thereof
WO2019180444A1 (en) * 2018-03-21 2019-09-26 The University Of Birmingham Luminescent compounds

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200808769A (en) * 2006-04-18 2008-02-16 Astrazeneca Ab Therapeutic compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3448171A (en) * 1966-09-06 1969-06-03 Wyandotte Chemicals Corp High molecular weight urethane polymers having an ordered arrangement of pendant unsaturation and process for their production
JP2015516977A (en) * 2012-04-20 2015-06-18 メリアル リミテッド Parasiticidal compositions containing benzimidazole derivatives, methods and uses thereof
WO2019180444A1 (en) * 2018-03-21 2019-09-26 The University Of Birmingham Luminescent compounds
CN112154143A (en) * 2018-03-21 2020-12-29 伯明翰大学 Luminescent compounds

Also Published As

Publication number Publication date
BE595327A (en) 1961-03-23

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