Volume 22, Issue 27
Heterocyclic Compounds
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ChemInform Abstract: Tetrahydropyridyloxadiazoles: Semirigid Muscarinic Ligands.

G. A. SHOWELL

G. A. SHOWELL

Merck Sharp Dohme Res. Lab., Dep. Biochem. Chem., Neurosci. Res. Cent., Harlow, Essex CM20 2QR, UK

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T. L. GIBBONS

T. L. GIBBONS

Merck Sharp Dohme Res. Lab., Dep. Biochem. Chem., Neurosci. Res. Cent., Harlow, Essex CM20 2QR, UK

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C. O. KNEEN

C. O. KNEEN

Merck Sharp Dohme Res. Lab., Dep. Biochem. Chem., Neurosci. Res. Cent., Harlow, Essex CM20 2QR, UK

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A. M. MACLEOD

A. M. MACLEOD

Merck Sharp Dohme Res. Lab., Dep. Biochem. Chem., Neurosci. Res. Cent., Harlow, Essex CM20 2QR, UK

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K. MERCHANT

K. MERCHANT

Merck Sharp Dohme Res. Lab., Dep. Biochem. Chem., Neurosci. Res. Cent., Harlow, Essex CM20 2QR, UK

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J. SAUNDERS

J. SAUNDERS

Merck Sharp Dohme Res. Lab., Dep. Biochem. Chem., Neurosci. Res. Cent., Harlow, Essex CM20 2QR, UK

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S. B. FREEDMAN

S. B. FREEDMAN

Merck Sharp Dohme Res. Lab., Dep. Biochem. Chem., Neurosci. Res. Cent., Harlow, Essex CM20 2QR, UK

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S. PATEL

S. PATEL

Merck Sharp Dohme Res. Lab., Dep. Biochem. Chem., Neurosci. Res. Cent., Harlow, Essex CM20 2QR, UK

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R. BAKER

R. BAKER

Merck Sharp Dohme Res. Lab., Dep. Biochem. Chem., Neurosci. Res. Cent., Harlow, Essex CM20 2QR, UK

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First published: July 9, 1991

Abstract

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ChemInform Abstract

Arecoline (Ia) and 6-methylarecoline (Ib) react with the amidoximes (II) to give the oxadiazoles (III). Conversion of (I) to the N-protected derivatives (V) followed by coupling with (IIa) or (IIc) and subsequent deprotection yields the NH analogues (VI). Similarly, (IX) is synthesized as shown in the reaction scheme. The derivatives (VIa) and (IX) are the most potent muscarinic antagonists among the compounds prepared.

chemical structure image

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