N-Acetyl-para-aminophenyl N'-acetylamino-S-(tetrahydro-2-pyranyl

Details N-Acetyl-para-aminophenyl N'-acetylamino-S-(tetrahydro-2-pyranyl N-Acetyl-para-aminophenyl N'-acetylamino-S-(tetrahydro-2-pyranyl

1982-03-22

1983-09-20

Trousof, Natalie

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30908

Patent

active

044058004

ABSTRACT:
N-Acetyl-para-aminophenyl N'-acetylaminothioalkanoates I are new analgesic compounds with greatly reduced hepatotoxic effects, when taken in overdose, relative to N-acetyl-para-aminophenyl. They are prepared by reacting an N-acetylaminothioalkanoic acid IV with a reactive organic chloride V to form a mixed anhydride II and then reacting the latter with N-acetyl-para-aminophenol. The mixed anhydrides II are new and useful intermediates. Alternatively the derivatives I may be prepared by reacting the acid IV with bis-(4-nitrophenyl) sulfite to form a para-nitrophenyl N-acetylaminothioalkanoic acid ester VIII, reducing the latter to a para-aminophenyl N-acetylaminothioalkanoate VII, and acetylating this product. The esters VII and VIII are new and useful intermediates. Both reactions may pass through S-blocked intermediates, which are also new. Pharmaceutical compositions containing the derivatives I are disclosed, and also analgesic methods using them.

REFERENCES:
patent: 3591686 (1971-07-01), Sheffner
A. E. M. McLean, The Lancet, p. 729 (Apr. 20, 1974).
Maxwell et al., The Lancet, pp. 610-611 (Sep. 27, 1975).
McLean and Day, "The Effect of Diet on the Toxicity of Paracetamol and the Safety of Paracetamol-Methionine Mixtures", Biochemical Pharmacology 24, 37-42 (1975).
Kovach, "Aminoacid Esters of P-Acetamidophenol as Prodrugs", a Ph.D. Thesis, University of Kansas, 1974 [C.A. 83, 193681t (1975)]; Diss. Abstr. Int. B 1975, 36(2), 734-735.
Piperno et al., (McNeil Labs. Inc., Fort Washington, Pa.), The Lancet, pp. 738-739 (Oct. 2, 1976).
Gerber et al., (Dept. of Pharmacology, Vanderbilt University, School of Medicine, Nashville, Tennessee), The Lancet, pp. 657-658 (Mar. 19, 1977).

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