Synthesis of N-Substituted C-Normorphinans and Their Pharmacological Properties
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概要
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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.
- 1992-05-25
著者
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井上 博純
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd, .
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武田 幹男
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,
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岡村 公生
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,
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伊達 忠正
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,
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本間 靖
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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野口 勝通
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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斎藤 清一
Organic Chemistry Research Laboratory
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斉藤 清一
田辺製薬研
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斎藤 清一
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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岡村 公生
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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塗本 精一
Safety Research Laboratory Tanabe Seiyaku Co. Ltd.
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山村 道夫
Safety Research Laboratory, Tanabe Seiyaku Co., Ltd.,
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本間 靖
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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武田 幹男
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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伊達 忠正
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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井上 博純
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd .
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山村 道夫
Safety Reseach Laboratory:tanabe Seiyaku Co. Ltd.
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山村 道夫
Safety Research Laboratory Tanabe Seiyaku Co. Ltd.
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野口 勝通
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd. :(present Address)sapporo Branch Tanab
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