1,2,5,6/1,2,3,6- TETRAHYDROPYRIDINYLTETRAHYDROCYCLOPENTA/ -HEXAISOXAZOLE DERIVATIVES AND METHOD FOR PREPARING THE SAME

摘要

PURPOSE: 1,2,5,6/1,2,3,6- Tetrahydropyridinyltetrahydrocyclopenta/-hexaisoxazole derivatives and a method for preparing the same are provided. The compounds are useful for treatment of dementia and brain disease as muscarinic receptor agonist and operated as tetrahydropyridine bioisostere. CONSTITUTION: 1,2,5,6/1,2,3,6- Tetrahydropyridinyltetrahydrocyclopenta/ -hexaisoxazole derivatives are represented by the formula(1), wherein X is CH2, O or S; n is an integer of 1 or 2; HA is inorganic or organic salt selected from HCl, oxalic acid, p-toluenesulfonic acid, tartaric acid and fumaric acid. A method for preparing the 1,2,5,6/1,2,3,6- Tetrahydropyridinyltetrahydrocyclopenta/-hexaisoxazole derivatives comprises the steps of: (a) adding NaOCl to 3/4-pyridinealdoxime of the formula(2) and cyclopentene/-hexene derivatives in a solvent and cyclizing them to prepare a compound of the formula(4); (b) reacting the compound of the formula(4) with CH3I to prepare 3/4-substituent isomer of the formula(5); and (c) reducing the compound of the formula(5) and adding inorganic and organic acids into the reduced compound.