SYNTHESIS OF N-SUBSTITUTED C-NORMORPHINANS AND THEIR PHARMACOLOGICAL PROPERTIES

被引：0

作者：

TAKEDA, M ^{[1
]}

INOUE, H ^{[1
]}

NOGUCHI, K ^{[1
]}

HONMA, Y ^{[1
]}

OKAMURA, K ^{[1
]}

DATE, T ^{[1
]}

NURIMOTO, S ^{[1
]}

YAMAMURA, M ^{[1
]}

SAITO, S ^{[1
]}

机构：

[1] TANABE SEIYAKU CO LTD, SAFETY RES LAB, YODOGAWA KU, OSAKA 532, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1992年 / 40卷 / 05期

关键词：

MORPHINAN; C-NORMORPHINAN; CYCLIZATION; ANALGESIC ACTIVITY; NARCOTIC ANTAGONIST ACTIVITY; PHYSICAL DEPENDENCE CAPACITY;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Several N-substituted C-normorphinans (VIII and IX) were synthesized and tested for their analgetic and narcotic antagonist activities and physical dependence capacity. Treatment of N-formyl-octahydro-2-pyrindine (IIIc) with polyphosphoric acid readily gave N-formyl-C-normorphinan (IV). The N-nor bases (V and VII) obtained from IV were converted to VIII and IX. The N-methyl derivative (I), which was previously reported to be inactive by Haffner's method, exhibited potent analgetic activity by the hot plate method and the AcOH-induced writhing test. Compounds VIII and IX showed pharmacological properties similar to those of N-substituted morphinans and exhibited agonist (analgetic) and/or narcotic antagonist activities. The C-nor analogue (IXa) of cyclorphan (IIc) exhibited potent analgetic and antagonist activities with no physical dependence capacity in the single-dose suppression tests both in rats and monkeys.

引用

页码：1186 / 1190

页数：5

共 16 条

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