PURPOSE: To obtain a compound useful as a new type anti-schizophrenic medicine exhibiting high affinity for sigma binding site, different from well-known dopamine receptor.
CONSTITUTION: A compound of formula I (nitrogen-containing ring B is 3- azabicyclo[3.2.2]nonan-3-yl or 4-azatricyclo[4.3. 1.13.8]undecan-4-yl; R is H, a lower alkyl, a lower alkoxy, OH or a halogen), e.g. 3-[2-(2-adamantyl)ethyl]-3- azabicyclo[3.2.2] nonane. The compound of formula I is obtained by reducing a carbonyl group of a compound of formula II. The reduction reaction is carried out using a reducing agent such as lithium aluminum hydride in an inert organic solvent (e.g. THF). The compound of formula I does not exhibit affinity for neurotransmission based receptor such as dopamine (D1, D2) receptor or serotonin (5-HT1A, 5-HT2) receptor and exhibits effectiveness on suppressing action of apomorphine inducing climbing.
MOCHIZUKI DAISUKE