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Profadol

Chemical compound

Profadol

Chemical compound

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Profadol (CI-572) is an opioid analgesic which was developed in the 1960s by Parke-Davis. It acts as a mixed agonist-antagonist of the μ-opioid receptor. The analgetic potency is about the same as of pethidine (meperidine), the antagonistic effect is 1/50 of nalorphine.

Synthesis

3149123}} (1964 to Parke Davis and Co LLC).</ref>

The Knoevenagel condensation between 3'-Methoxybutyrophenone [21550-06-1] and Ethyl cyanoacetate gives (1). Conjugate addition of cyanide gives (2). Hydrolysis of both nitrile groups, saponification of the ester and decarboxylation gives the diacid, CID:164137621 (3). Imide formation occurs upon treatment with methylamine giving 3-(3-Methoxyphenyl)-1-methyl-3-propylpyrrolidine-2,5-dione, CID:163444474 (4). Reduction of the imide by lithium aluminium hydride gave [1505-32-4][29369-01-5] (5). Demethylation completed the synthesis of Profadol (6).

References

References

  1. {{cite patent
  2. (1976). "Arzneimittelchemie 1. Grundlagen, Nerven, Muskeln und Gewebe". Georg Thieme Verlag.
  3. Cavalla, J. F.; Jones, R.; Welford, M.; Wax, J.; Winder, C. V. (1964). "Analgetics Based on the Pyrrolidine Ring. III". Journal of Medicinal Chemistry. 7 (4): 412–415. doi:10.1021/jm00334a005.
  4. John Frederick Cavalla & Alan Chapman White, {{Cite patent. DE. 1272296 (1968 to Parke Davis and Co LLC).
  5. Cavalla John Frederick, {{US patent. 3149123 (1964 to Parke Davis and Co LLC).
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3-hydroxyphenyl-compounds pyrrolidines drugs-developed-by-parke-davis
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