Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1981-03-23
1982-11-30
Brown, Johnnie R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560146, 562556, C07C 69773
Patent
active
043617034
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.
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Andrews Roderic S.
Legros Jean
Margetts George
Bair Robert K.
Brown Johnnie R.
Pepper Frederick W.
Sterling Drug Inc.
Wyatt B. Woodrow
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