Starting from 3,6-dichloropyridazine-4-carboxylic acid chloride, a series of pyridazino[3,4-b][1,5]benzodiazepin-5-ones bearing various substituents in positions 3, 6, 8 and 11 was prepared via N-alkyl-3-alkylamino-6-chloro-N-(2-chloro-5-nitrophenyl)-pyridazine-4-carboxamides. The latter were smoothly accessible by treatment of N-alkyl-3,6-dichloro-N-(2-fluorophenyl)-pyridazine-4-carboxamides with primary aliphatic amines. The new tricyclic compounds, which are structurally related to nevirapine and congeners were screened as human immunodeficiency virus type 1 reverse transcriptase inhibitors; the influence of the substitution pattern on inhibitory potency is discussed.
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