GB1292567A - Bis basic ketones of dibenzothiophene - Google Patents

Abstract

1292567 Bis basic ketones of dibenzothiophene RICHARDSON-MERRELL Inc 30 April 1971 [1 May 1970] 12495/71 Heading C2C Novel compounds of Formula Ia wherein Y is a group of Formula A wherein R 1 and R 2 are each H, C 1-6 alkyl, C 3-6 cycloalkyl or C 3-6 alkenyl in which the vinyl unsaturation is not in the 1-position; or a group of Formula B wherein n is 4, 5 or 6 and R<SP>3</SP> is H, C 1-4 alkyl, phenyl or benzyl; or a group of Formula C wherein X is -O- or R 4 N where R 4 is H or C 1-4 alkyl; or a group of Formula D wherein m is 1 or 2 and p is 2 or 3 ; or a group of Formula E wherein q is or 2 and r is 1 or 2 or also 3 if q is 1; and A is a C 1-6 straight or branched-chain alkylene radical are prepared by one of the following methods (a) a compound of formula HY is reacted with a compound of Formula F wherein Hal is halogen or (b) a dicyano dibenzothiophene is reacted with a Grignard reagent of formula HalMgAY or (c) formaldehyde and a secondary amine HY is reacted with a diacetyldibenzothiophene. Compounds of Formula F above are prepared either by a Friedel-Crafts reaction on dibenzothiophene using a reagent or where A is CH 2 by halogenation of the methyl groups of the diacetyl dibenzothiophene which may be prepared by the above reaction using a reactive ester or anhydride of acetic acid. Compounds of Formula III are prepared either by dehydration of the diamide of the corresponding dicarboxylic acid or by diazatization of the corresponding diamine followed by reaction with cuprous cyanide. Pharmaceutical compositions having antiviral activity and being in conventional forms for oral, topical, bucal, internasal or parenteral administration comprise an above novel compound or salt and a non-toxic pharmaceutical carrier.