Analgesic N-acetyl-para-aminophenyl N'-acetylaminothioalkanoates

Drug – bio-affecting and body treating compositions – Antigen – epitope – or other immunospecific immunoeffector – Virus or component thereof

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424246, 424253, 424254, 424273P, 424278, 424279, 424311, 424313, 424324, 424325, 424330, 560142, A61K 3122, A61K 31615, C07C 6708

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active

041817192

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: 3983138 (1976-09-01), Saari
Kovach, Dissertation Abstracts International B 1975, 36 (2), 734-735.

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