Tricyclic analogues of the antiallergic agent oxatomide: 1-(3-(4-(10,11-Dihydro-5H-dibenzo[a,d]cycloheptene-5-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one and the related 6,11-dihydrodibenzo[b,e]thiepin, 4,9-dihydrothieno[2,3-c]-2-benzothiepin, and 10,11-dihydrodibenzo[b,f]thiepin derivatives

Abstract

11-Chloro-6,11-dihydrodibenzo[b,e]thiepin and its 2-methyl derivative VI were transformed via the 11-(4-ethoxycarbonyl)-1-piperazinyl) compounds IVc and Vc to 11-(1-piperazinyl)compounds IVb and Vb. Their reactions with 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one (II) afforded the title compounds IVa and IVb. Similar reactions and sequences in the series of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene, 4,9-dihydrothieno[2,3-c]-2-benzothiepin, and 10,11-dihydrodibenzo[b,f]thiepin led to further oxatomide (Ia) analogues IIIa and VIIa-XIa. In the test of passive cutaneous anaphylaxis in rats, compound VIIIa was more active than Ia, and IVa had similar activity like Ia.