GB1439008A - 4-methyl-5-amino-ethylimidazole derivatives and pharmaceutical compositions thereof - Google Patents

4-methyl-5-amino-ethylimidazole derivatives and pharmaceutical compositions thereof

Info

Publication number
GB1439008A
GB1439008A GB5518673A GB5518673A GB1439008A GB 1439008 A GB1439008 A GB 1439008A GB 5518673 A GB5518673 A GB 5518673A GB 5518673 A GB5518673 A GB 5518673A GB 1439008 A GB1439008 A GB 1439008A
Authority
GB
United Kingdom
Prior art keywords
methyl
ethyl
prepared
followed
tetrahydroimidazo
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
GB5518673A
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.)
Smith Kline and French Laboratories Ltd
GlaxoSmithKline LLC
Original Assignee
Smith Kline and French Laboratories Ltd
GlaxoSmithKline LLC
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 Smith Kline and French Laboratories Ltd, GlaxoSmithKline LLC filed Critical Smith Kline and French Laboratories Ltd
Priority to GB5518673A priority Critical patent/GB1439008A/en
Publication of GB1439008A publication Critical patent/GB1439008A/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
    • C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

1439008 4 - Methyl - 5 - (2 - alkylaminoethyl)imidazoles SMITH KLINE & FRENCH LABORATORIES Ltd 25 Nov 1974 [28 Nov 1973] 55186/73 Heading C2C Novel compounds of the Formula I wherein R 1 and R 2 are independently methyl or ethyl and pharmaceutically acceptable salts thereof may be prepared (1) where both R 1 and R 2 are methyl by methylation of the corresponding primary amine using formaldehyde under reducing conditions, (2) where R 1 and R 2 are both ethyl, by reduction of the corresponding N,N-diethylacetamide and (3) where R 1 is methyl and R 2 is ethyl by reduction of 1- methyl - 6 - ethyl - 5 - oxo - 5,6,7,8 - tetrahydroimidazo[1,5-c]pyrimidine. N,N - Diethyl(4 - methylimidazol - 5 - yl)- acetamide is prepared by hydrolysis of 4- methyl-5-cyanomethyl imidazole hydrochloride to (4 - methylimidazol - 5 - yl)acetic acid followed by formation of the acid chloride and reaction thereof with diethylamine. 1 - Methyl - 6 - ethyl - 5 - oxo - 5,6,7,8 - tetrahydroimidazo[1,5-c]pyrimidine is prepared by reaction of 4 - methyl - 5 - (2 - aminoethyl)- imidazole with N,N<SP>1</SP>-carbonyl diimidazole to yield 1 - methyl - 5 - oxo - 5,6,7,8 - tetrahydroimidazo[1,5-c]pyrimidine followed by reaction with ethyl bromide and strong base to yield the required compound, which is isolated as its hydrochloride. 4 - Methyl - 5 - methylaminoethylimadazole dihydrochloride is prepared by reduction of the first intermediate in the paragraph above followed by salt formation. 4 - Methyl - 5 - ethylaminoethylimidazole dihydrochloride is prepared by hydrolysis of the second intermediate in the same paragraph followed by salt formation. Pharmaceutical compositions of the compounds I or compounds of the Formula I in which R 1 is additionally hydrogen with the usual excipients may be administered parenterally as a diagnostic agent to test the secretory action of the stomach.
GB5518673A 1973-11-28 1973-11-28 4-methyl-5-amino-ethylimidazole derivatives and pharmaceutical compositions thereof Expired GB1439008A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB5518673A GB1439008A (en) 1973-11-28 1973-11-28 4-methyl-5-amino-ethylimidazole derivatives and pharmaceutical compositions thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5518673A GB1439008A (en) 1973-11-28 1973-11-28 4-methyl-5-amino-ethylimidazole derivatives and pharmaceutical compositions thereof

Publications (1)

Publication Number Publication Date
GB1439008A true GB1439008A (en) 1976-06-09

Family

ID=10473215

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5518673A Expired GB1439008A (en) 1973-11-28 1973-11-28 4-methyl-5-amino-ethylimidazole derivatives and pharmaceutical compositions thereof

Country Status (1)

Country Link
GB (1) GB1439008A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE35224E (en) * 1987-01-13 1996-04-30 The Board Of Trustees Of The Leland Stanford Junior University Histamine derivatives as immune modulators

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE35224E (en) * 1987-01-13 1996-04-30 The Board Of Trustees Of The Leland Stanford Junior University Histamine derivatives as immune modulators

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee