Mixed anhydrides of N'-acetylaminothioalkanoates

Details Mixed anhydrides of N'-acetylaminothioalkanoates Mixed anhydrides of N'-acetylaminothioalkanoates

1979-04-02

1984-11-13

Garner, Vivian

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260463, 260545R, 260546, 424199, 424233, 424246, 424253, 424254, 424260, 424273P, 424279, 424311, 424313, 549419, 560142, C07C14900, C07C149243, C07C14943, C07D30908

Patent

active

044824955

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-aminophenol. 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
Lancet, Apr. 20, 1974, p. 729.
Lancet, Sep. 27, 1975, pp. 610-611; Act. 2, 1976, pp. 738-739; Mar. 19, 1977, pp. 657-658.
Biochem. Pharmacology, vol. 24, pp. 37-42, 1975.
B:Pharmaceuticals, W22-25/5/75, p. 6, Derwent German Patents Gazette, Jul. 8, 1975.

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