抗アポモルヒネ活性を有する2-Oxooctahydroimidazo[1,2-α]pyridine-3-spiro-4'-piperidine誘導体の合成

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4'-Carbamoyl-1,4'-bipiperidine 1 was dehydrogenated on Pd-C to give 2-oxo-2,3,5,6,7,8-hexahydroimidazo [1,2-α] pyridine-3-spiro-4'-piperidine 2,which was reduced to 2-oxo-1,2,3,5,6,7,8,8a-octahydroimidazo [1,2-α] pyridine-3-spiro-4'-piperidine 3 with NaBH_4. The iminodibenzyl and similar derivatives of 2 and 3 were synthesized and evaluated by using antiapomorphine test in mice. The derivatives of 3 had more potent antagonistic activity than those of 2 and the order of potency of 3 was : chloriminodibenzyl > chlordibenzocycloheptene > iminodibenzyl > iminostilbene > fluorene. Further chemical modification of the most active chloriminodibenzyl derivative 8,such as the substitution of Cl atom to Br atom, N-methylation on amine moiety, the replacement of imidazopyridine ring to imidazopyrrole ring, did not give any positive effect. Therefore, 8 may have potential usefulness as an antipsychotic drug.
1989-02-25