Nitrogen bridgehead compounds. 18. New antiallergic 4H-pyrido[1,2-a ]pyrimidin-4-ones. 1

I. Hermecz, Tibor Breining, Zoltán Mészáros, Agnes Horváth, Lelle Vasvári-Debreczy, Franz Dessy, Christine DeVos, Ludovic Rodriguez

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

A new type of antiallergic agent, 9-hydrazono-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-ones, was synthesized and evaluated for inhibitory effects in the rat reagenic passive cutaneous anaphylaxis (PCA) screen. Several racemic 6-methyl derivatives were found to be more potent than disodium chromoglycate intravenously and some were also active orally. Structure-activity relationships are discussed. High stereospecificity was observed in the 6-methyl series between the enantiomers with 6S and 6R absolute configuration, the former being more active. Compound 17, (+)-6(S)-methyl-9-(phenylhydrazono)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3- carboxylic acid [Chinoin-1045; UCB L140], has an ED50 value of 1.0 μmol/kg po and is now under clinical investigation.

Original languageEnglish
Pages (from-to)1140-1145
Number of pages6
JournalJournal of Medicinal Chemistry
Volume25
Issue number10
Publication statusPublished - 1982

Fingerprint

Nitrogen Compounds
Anti-Allergic Agents
Passive Cutaneous Anaphylaxis
Enantiomers
Structure-Activity Relationship
Carboxylic Acids
Rats
Derivatives
pyrimidine
compound 17

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Hermecz, I., Breining, T., Mészáros, Z., Horváth, A., Vasvári-Debreczy, L., Dessy, F., ... Rodriguez, L. (1982). Nitrogen bridgehead compounds. 18. New antiallergic 4H-pyrido[1,2-a ]pyrimidin-4-ones. 1. Journal of Medicinal Chemistry, 25(10), 1140-1145.

Nitrogen bridgehead compounds. 18. New antiallergic 4H-pyrido[1,2-a ]pyrimidin-4-ones. 1. / Hermecz, I.; Breining, Tibor; Mészáros, Zoltán; Horváth, Agnes; Vasvári-Debreczy, Lelle; Dessy, Franz; DeVos, Christine; Rodriguez, Ludovic.

In: Journal of Medicinal Chemistry, Vol. 25, No. 10, 1982, p. 1140-1145.

Research output: Contribution to journalArticle

Hermecz, I, Breining, T, Mészáros, Z, Horváth, A, Vasvári-Debreczy, L, Dessy, F, DeVos, C & Rodriguez, L 1982, 'Nitrogen bridgehead compounds. 18. New antiallergic 4H-pyrido[1,2-a ]pyrimidin-4-ones. 1', Journal of Medicinal Chemistry, vol. 25, no. 10, pp. 1140-1145.
Hermecz I, Breining T, Mészáros Z, Horváth A, Vasvári-Debreczy L, Dessy F et al. Nitrogen bridgehead compounds. 18. New antiallergic 4H-pyrido[1,2-a ]pyrimidin-4-ones. 1. Journal of Medicinal Chemistry. 1982;25(10):1140-1145.
Hermecz, I. ; Breining, Tibor ; Mészáros, Zoltán ; Horváth, Agnes ; Vasvári-Debreczy, Lelle ; Dessy, Franz ; DeVos, Christine ; Rodriguez, Ludovic. / Nitrogen bridgehead compounds. 18. New antiallergic 4H-pyrido[1,2-a ]pyrimidin-4-ones. 1. In: Journal of Medicinal Chemistry. 1982 ; Vol. 25, No. 10. pp. 1140-1145.
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