SE360854

1304651 Bis-basic ketones of fluoroanthene RICHARDSON-MERRELL Inc 27 April 1971 [27 April 1970] 11674/71 Heading C2C Novel compounds of the Formula I wherein A is C 1-6 alkylene and Y is (a) a group -NR1R2 wherein R1 and R2 are each hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 alkenyl in which the vinyl unsaturation is other than in the 1-position or, (b) where n is 4 to 6, R3 is hydrogen, C 1-4 alkyl, phenyl or benzyl attached to any one of the carbon atoms of the heterocyclic ring or (c) wherein X is O or NR4 and R4 is hydrogen or C 1-4 alkyl or (d) wherein p is 2 or 3 and m is 1 or 2, or (e) wherein q is 1 or 2 and r is 1 to 3 providing when r = 3, q = 1 and pharmaceutically acceptable salts thereof may be prepared by (i) reacting a compound VI with an amine Y-H, wherein Hal is chlorine, bromine or iodine; (ii) when A is a straight chain C 3-6 alkylene chain and Y is tertiary amino group, reacting a dinitrile of fluoranthene of the formula with a Grignard reagent XMg(CH 2 ) t Y to produce a compound wherein X:is bromine or chlorine, t is 3 to 6; (iii) when A is CH 2 CH 2 and Y is a tertiary amino group, reacting a diacetyl fluoranthene with formaldehyde and Y-H, or (IV) forming a salt from the free base. The intermediate VI may be formed by a Friedel Craft reaction of fluoranthene with a halo alkanoyl halide. 3,9 - Bis (4 - chlorobutyryl) fluoranthene bisdiethyl ketal may be formed by reacting VI, A = (CH 2 ) 3 , Hal = chloro with ethyl orthoformate in ethanolic hydrogen chloride. Pharmaceutical compositions of the compounds I show antiviral activity when administered orally, parenterally, topically or buccally with the usual excipients.