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This work has been carried out to investigate the chemical reactivity and synthetic potentiality of 2-thioxohydropyridine 11a-d via their reaction with several active halogencontaining compounds to afford the corresponding 2-alkylthiopyridine in some cases and thieno[2,3-b]pyridine directly in most cases. Thieno[2,3-b]pyridine-2-carbohydrazides obtained through the reaction of 2-ethoxycarbonylthienopyridines with hydrazine hydrate which in turn, used to obtain the corresponding pyrimidinones 20-26(a-d), 1,3,4- oxdiazoles 28, 30(a-d), pyrazolothienopyridine derivatives (32a-d) thienopyridine-3- amines (34a-d), pyrazolones (36a-d), pyrazolidine-3,5-diones (38a-d). 3- Aminopyrazolopyridine obtained via the reaction of 11a-e or 49a-e with hydrazine hydrate which in turn, reacted with nitrous acid to give the diazonium salts 51a-e which coupled with several active-hydrogen containing reagents to give the corresponding triazines. The structures of all newly synthesized heterocyclic compounds were elucidated by considering the data of IR, 1H NMR ( ppm), mass spectra as well as that of elemental analyses. Anti-Alzheimer, anti COX-2 and anti-Cancer activities were investigated for all newly