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Further Analgesics Based on Piperidine and Related Azacycloalkanes: Prodines, Promedols, Profadol, and Their Derivatives

  • Alan F. Casy
  • Robert T. Parfitt

Abstract

The major part of this chapter is devoted to 4-phenylpiperidine analgesics with C-alkyl substituents in the piperidine ring and to a consideration of their stereochemical structure-activity relationships. The effect of alkyl substitution in the piperidine ring of 4-phenylpiperidine analgesics has attracted much interest ever since the 3-methyl analogs of the reversed ester of pethidine were described by Roche workers in the late 1940s.(1) Since that time many 3-alkyl and all possible mono- and di-C-methyl derivatives of the reversed ester have been reported, and much evidence of potency variation amongst stereoisomers disclosed. The ease of synthetic access and the fact that replacement of 4-carbethoxy (CO2Et) by 4-propionyloxy (OCOEt) usually produces a major increase in potency (up to 20-fold regardless of the nature of the N-substituent)(2) are probable reasons why the bulk of the investigations have been of derivatives of the reversed ester rather than pethidine itself.

Keywords

Opioid Receptor Absolute Configuration Piperidine Ring Equatorial Methyl Dimethyl Analog 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer Science+Business Media New York 1986

Authors and Affiliations

  • Alan F. Casy
    • 1
  • Robert T. Parfitt
    • 1
    • 2
  1. 1.University of BathBathUK
  2. 2.Canberra College of Advanced EducationBelconnenAustralia

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