PROCESS FOR PREPARING 1,2,3,6-TETRAHYDROPYRIDINYL-BENZIMIDAZOLE DERIVATIVES WHICH ARE USEFUL FOR TREATMENT OF DEMENTIA AS MUSCARINIC RECEPTOR AGONIST WITH IMPROVED YIELD

• Main Authors: CHUNG, YONG JUN, KIM, YOUN CHUL, NAMGUNG, MI AE, JUNG, MYUNG HEE, AHN, MI JA, CHOI, IHL YOUNG, PARK, JUNG MEE, PARK, WOO KYU
• Format: Patent
• Language: English; Korean
• Published: 02.02.2005
• Edition: 7
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

PURPOSE: A process for preparing 1,2,3,6-tetrahydropyridinyl-benzimidazole derivatives is provided, thereby preparing the 1,2,3,6-tetrahydropyridinyl-benzimidazole derivatives which are useful for treatment of dementia as a muscarinic receptor agonist with improved yield. CONSTITUTION: The process for preparing 1,2,3,6-tetrahydropyridinyl-benzimidazole derivatives represented by formula (1) and pharmaceutically acceptable salts thereof comprises the steps of: (a) reacting 4-pyridinecarboxalaldehyde of formula (2) with a compound of formula (3) and iodibenzene diacetate(IBD) in solvent to prepare a compound of formula (4); (b) reacting the compound of formula (4) with KOH/CH3I to prepare a 5/6-substituent isomer compound of formula (5); (c) reacting the compound of formula (5) with CH3I to prepare a compound of formula (7); and (d) reacting the compound of formula (7) with NaBH4, and treating a reaction product with acid, wherein X is NH or NCH3; R is H, NH2, Cl, NO2 or OCH3; and HA is an organic or inorganic salt selected from HCl, oxalic acid, p-toluenesulfonate, tartaric acid and fumaric acid.