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Synthesis and antiallergy activity of 10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidines (2 and 3) and 10-oxo-10H-pyrido[1,2-a]thieno[3,4-d]pyrimidines (4 and 5) are described. The activity, shown by these compounds in the rat passive cutaneous anaphylaxis (PCA) test, is compared to the PCA data previously reported for a series of 4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidines. 10-Oxo-N-1H-tetrazol-5-yl-10H-pyrido[1,2-a]thieno[3,4-d]pyri midine (2b), 10-oxo-7-(1H-tetrazol-5-yl)-10H-pyrido[1,2-a]thieno[3,4-d]py rimidine (4e), and 3,10-dihydro-10-oxo-7-(1H-tetrazol-5-yl)-1H-pyrido[1,2-a]thieno[3, 4-d] pyrimidine (7e) gave a 100% inhibition in the rat PCA test at a dose of 5 mg/kg. The activity displayed by these compounds is comparable to that of the most active compounds in the 4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine series.

Ambruticin (I) wird auf den im Formelschema skizzierten Wegen in Analoga (II)-(XII) umgewandelt.

Aus dem 2-Hydroxy-1-methylsulfinylacetyl-benzol (I) erhalt man unter Ruckflus in Gegenwart von Trifluoressigsaure unter Annahme der Zwischenstufe (II),das Benzofuranon (III).

Die Kondensation des Amino-thiophenesters (I) mit den Nicotinsaurederivaten (II) fuhrt zu den 4-Oxo-pyrido[1,2-a]thieno[2,3-d]pyrimidinen (IIIa)-(IIIC), die in die Derivate (IIId)-(IIIf) und (V) ubergefuhrt werden.