GB1044933A - Improved method for the preparation of 1-(1-phenyl-ethyl)-5-[(r) (ar) n-co]-imidazoles and compounds produced thereby - Google Patents

Improved method for the preparation of 1-(1-phenyl-ethyl)-5-[(r) (ar) n-co]-imidazoles and compounds produced thereby

Info

Publication number
GB1044933A
GB1044933A GB1266465A GB1266465A GB1044933A GB 1044933 A GB1044933 A GB 1044933A GB 1266465 A GB1266465 A GB 1266465A GB 1266465 A GB1266465 A GB 1266465A GB 1044933 A GB1044933 A GB 1044933A
Authority
GB
United Kingdom
Prior art keywords
phenyl
give
acid
phenylethyl
reacting
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
GB1266465A
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.)
Janssen Pharmaceutica NV
Original Assignee
Janssen Pharmaceutica 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
Priority claimed from US360444A external-priority patent/US3336326A/en
Application filed by Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV
Publication of GB1044933A publication Critical patent/GB1044933A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

The invention comprises compounds of formula <FORM:1044933/C2/1> wherein R is a hydrogen atom or a C1-5 alkyl group and Ar is a phenyl group optionally substituted by one or more C1-5 alkyl, C1-5 alkoxy or nitro-groups or halogen atoms, or is a pyridyl group, acid addition salts thereof, and their preparation by reaction of a 1-(1-phenyl-ethyl)imidazole - 5 - carboxylic acid halide with an amine ArRNH. The compounds of the invention have anti-convulsant and sedative activity. 1 - (1 - Phenylethyl) - imidazole - 5 - carboxylic acid chloride is prepared by reaction of 1-phenylethylamine with ethyl chloroformate to give N-(ethoxycarbonylmethyl) - 1 - phenyl - ethylamine, reacting this with formic acid to give N-formyl-N -(ethoxycarbonylmethyl) - 1 - phenylethylamine, reacting this with sodium and potassium thiocyanate to give 1-(1-phenylethyl)-2-mercapto-5-methoxycarbonylimidazole, reacting this with nitric acid, sodium nitrite and hydrogen chloride to give 1 - (1 - phenylethyl) - 5 - (methoxycarbonyl) -imidazole hydrochloride and converting this to the corresponding acid and acid halide by successive hydrolysis and treatment with thionyl chloride.
GB1266465A 1964-04-16 1965-03-25 Improved method for the preparation of 1-(1-phenyl-ethyl)-5-[(r) (ar) n-co]-imidazoles and compounds produced thereby Expired GB1044933A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US360444A US3336326A (en) 1964-04-16 1964-04-16 Novel imidazole carboxamides

Publications (1)

Publication Number Publication Date
GB1044933A true GB1044933A (en) 1966-10-05

Family

ID=23417975

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1266465A Expired GB1044933A (en) 1964-04-16 1965-03-25 Improved method for the preparation of 1-(1-phenyl-ethyl)-5-[(r) (ar) n-co]-imidazoles and compounds produced thereby

Country Status (1)

Country Link
GB (1) GB1044933A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0248414A2 (en) * 1986-06-06 1987-12-09 Ciba-Geigy Ag Aralkyl imidazole derivatives
EP0438869A1 (en) * 1989-11-30 1991-07-31 Eli Lilly And Company Improvements in and relating to angiotensin II antagonists
CN109761906A (en) * 2019-03-02 2019-05-17 成都安诺晨创医药科技有限公司 A kind of substituted imidazole formate ester derivative and application thereof

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0248414A2 (en) * 1986-06-06 1987-12-09 Ciba-Geigy Ag Aralkyl imidazole derivatives
EP0248414A3 (en) * 1986-06-06 1988-01-27 Ciba-Geigy Ag Aralkyl imidazole derivatives
AU610501B2 (en) * 1986-06-06 1991-05-23 Ciba-Geigy Ag Aralkylimidazole derivatives
EP0438869A1 (en) * 1989-11-30 1991-07-31 Eli Lilly And Company Improvements in and relating to angiotensin II antagonists
CN109761906A (en) * 2019-03-02 2019-05-17 成都安诺晨创医药科技有限公司 A kind of substituted imidazole formate ester derivative and application thereof
CN109761906B (en) * 2019-03-02 2023-08-11 成都麻沸散医药科技有限公司 Substituted imidazole formate derivative and application thereof

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