A facile synthetic approach towards dithiatetraaza-macrocycles 4a and b was achieved through reaction of 2,2'-[alkanediylbis(thio)]bisbenzenamines 1a and b with 1,4-phenylenediisocyanate. However, reaction of 1a and b with a variety of aryl-, alkylisocyanates or isothiocyanates 2a-f afforded the corresponding bisurea and their thio-analogues 3a-l. Anti-inflammatory activity of the prepared compounds (in a dose of 50 mg/kg body weight) using in vivo acute carrageenan-induced paw oedema in rats is studied. Compounds 3e and 4b reveal the best anti-inflammatory properties among all the tested compounds with potency (% oedema inhibition of the tested compounds regarding % oedema inhibition of indomethacin "which was used as a reference standard in a dose of 10 mg/kg body weight") 0.90 and 0.85, respectively.