Richardson-Merrell Inc.

Irving Shemano

Bis-basic substituted aromatic polycyclic compounds of the following structure are useful in treating conditions of delayed hypersensitivity: ##STR1## wherein [W] represents an aromatic polycyclic nucleus selected from fluoranthene, fluorene, fluoren-9-ol, fluoren-9-one, dibenzofuran, dibenzothiophene, carbazole, N-(lower)alkyl carbazole, xanthene, xanthone, thioxanthene, phenoxathiin, or anthraquinone; Y represents carbonyloxy, carbonylthio, oxygen, divalent sulfur or carbonyl with the provisos that when Y is carbonyloxy or carbonylthio, [W] is other than thioxanthene, phenoxathiin or anthraquinone, when Y is oxygen or divalent sulfur, [W] is other than thioxanthene or phenoxathiin, and when Y is carbonyl, [W] is other than fluoren-9-ol or anthraquinone; A represents a straight or branched alkylene chain of from 1 to 6 carbon atoms with the proviso that when Y is carbonyloxy or carbonylthio, A contains at least 2 straight chain carbon atoms, that is, an ethylene radical; R represents hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, phenyl or benzyl; and pharmaceutically useful acid addition salts.

Pharmaceutically useful nitrogen containing heterocyclic derivatives

Novel 3,6-bis basic ketone derivatives of acenaphthene useful in treating conditions of delayed hypersensitivity are disclosed.

Method of treating conditions of delayed hypersensitivity using

Compounds of the following general formula are useful in the treatment of conditions of delayed hypersensitivity: ##SPC1## Wherein X represents a bond, --CH.sub.2 --, or carbonyl; Y represents a vinylene group, ##EQU1## carbonyl, oxygen, divalent sulfur, or carbonyloxy with the proviso that when Y is ##EQU2## or vinylene, X is not carbonyl; A represents a straight or branched alkylene chain of from 1 to 6 carbon atoms with the proviso that when Y is vinylene, A contains from 1 to 5 carbon atoms and with the proviso that when Y is carbonyloxy or carbonylthio, A contains from 2 to 6 carbon atoms; each of R.sup.1 and R.sup.2 represents hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms; or alkenyl of 3 to 6 carbon atoms having the vinyl unsaturation in other than 1-position; and pharmaceutically acceptable acid addition salts thereof.

Pharmaceutically useful oxygen containing heterocyclic derivatives

Compounds of the following general structure are useful in treating conditions of delayed hypersensitivity: ##EQU1## wherein [W] represents an aromatic polycyclic nucleus selected from fluoranthene, fluorene, fluoren-9-ol, fluoren-9-one, carbazole, N-(lower) alkyl carbazole or anthraquinone; Y represents carbonyl, divalent sulfur or oxygen; with the proviso that when Y is carbonyl, [W] is other than fluoren-9-ol or anthraquinone; A represents a straight or branched alkylene chain of from 1 to 6 carbon atoms; and each of R.sup.1 and R.sup.2 represents hydrogen, lower alkyl of from 1 to 4 carbon atoms, or alkenyl of from 3 to 6 carbon atoms having the vinyl unsaturation in other than the 1-position; and pharmaceutically useful acid addition salts thereof.

Pharmaceutically useful bis-amine derivatives

Bis-basic ester derivatives of the following general formula are useful in the treatment of conditions of delayed hypersensitivity. ##EQU1## wherein [W] represents an aromatic polycyclic nucleus selected from fluoranthene, fluorene, fluoren-9-ol, fluoren-9-one, carbazole, or N-(lower)alkyl carbazole; X represents oxygen or sulfur; A represents a straight or branched alkylene chain of from 2 to 6 carbon atoms; and each of R.sup.1 and R.sup.2 is hydrogen, straight or branched lower alkyl of from 1 to 4 carbon atoms, or alkenyl of from 3 to 6 carbon atoms having the vinyl unsaturation in other than the 1-position; and pharmaceutically useful acid addition salts thereof.

Pharmaceutically useful bis-basic ester and thioester derivatives

Bis-basic substituted aromatic polycyclic compounds of the following structure are useful in treating conditions of delayed hypersensitivity: ##SPC1## Wherein [W] represents an aromatic polycyclic nucleus selected from fluoranthene, fluorene, fluoren-9-ol, fluoren-9-one, dibenzofuran, dibenzothiophene, carbazole, N-(lower)alkyl carbazole, xanthene, xanthone, thioxanthene, phenoxathiin, or anthraquinone; Y represents carbonyloxy, carbonylthio, oxygen, divalent sulfur or carbonyl with the provisos that when Y is carbonyloxy or carbonylthio, [W] is other than thioxanthene, phenoxathiin or anthraquinone, when Y is oxygen or divalent sulfur, [W] is other than thioxanthene or phenoxathiin, and when Y is carbonyl, [W] is other than fluoren-9-ol or anthraquinone; A represents a straight or branched alkylene chain of from 1 to 6 carbon atoms with the proviso that when Y is carbonyloxy or carbonylthio, A contains at least 2 straight chain carbon atoms, that is, an ethylene radical; R represents hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, phenyl or benzyl; and pharmaceutically useful acid addition salts.

Compounds of the following general formula are useful in the treatment of conditions of delayed hypersensitivity. ##SPC1## Wherein X represents a bond, --CH.sub.2 --, or oxygen; Y represents a vinlyene group, --CH(OH)--, carbonyl, oxygen, divalent sulfur, or carbonyloxy with the proviso that when Y is oxygen, divalent sulfur or carbonyloxy, X represents a bond; A represents a straight or branched alkylene chain of from 1 to 6 carbon atoms with the proviso that when Y is vinlyene, A contains from 1 to 5 carbon atoms; and with the proviso that when Y is carbonyloxy, A contains from 2 to 6 carbon atoms; each of R.sup.1 and R.sup.2 is selected from hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms; or alkenyl of 3 to 6 carbon atoms having the vinyl unsaturation in other than the 1-position, and pharmaceutically acceptable acid addition salts thereof.

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Cincinnati, OH, United States of America

Irving Shemano