Tetrahydroacridones having chemotherapeutic action and process for preparing them
AssigneeHoechst Aktiengesellschaft
InventorsWalter Durckheimer, Wolfgang Raether, Hubert Georg Seliger
Life of this patent
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Abstract
Tetrahydroacridones and their salts with physiologically tolerated acids and bases and process for preparing them. The compounds have a valuable chemotherapeutic action and may be used as drugs against protozoan diseases.
Claims16
A tetrahydroacridone of the formula ##SPC4##
- and salts thereof with physiologically tolerated acids and bases, wherein R.sup.1 is oxygen;
- R.sup.2 - R.sup.7, which may be the same or different are hydrogen, straight-chain or branched lower alkyl having 1 to 4 carbon atoms, phenyl, or phenyl mono- or di-substituted with fluorine, chlorine, or trifluoromethyl, except that only one of R.sup.2 - R.sup.7 is phenyl or substituted phenyl;
- R.sup.8, R.sup.9, and R.sup.11, which may be the same or different, are hydrogen, fluorine, chlorine, or trifluoromethyl;
- R.sup.10 is chlorine;
- and R.sup.12 is hydrogen or hydroxy.
7-chloro-3-(2-chloro-4-trifluoromethylphenyl)-10-hydroxy -1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
7-chloro-10-hydroxy-1-oxo-3-phenyl-1,2,3,4-tetrahydro-9 (10H)-acridone.
7-chloro-3-(4-chlorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
7-chloro-3-(2-chlorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
7-chloro-10-h ydroxy-1-oxo-3-(4-trifluoromethylphenyl)-1,2,3,4-tetrahydro-9 (10H)-acridone.
7-chloro-3-(2,4-dichlorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
7-chloro-3-(3-chlorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
7-chloro-3-(4-fluorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
7-chloro-10-hydroxy-3-(4-nitrophenyl)-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
7-chloro-10-hydroxy-3-(2-methoxyphenyl)-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
6,7-dichloro -10-hydroxy-1-oxo-3-(3-trifluorophenyl)-1,2,3,4-tetrahydro-9 (10H)-acridone .
A method for making a tetrahydroacridone of the formula ##SPC5##
- wherein R.sup.2 - R.sup.7, which may be the same or different, are hydrogen, straight-chain or branched lower alkyl having 1 to 4 carbon atoms, phenyl, nitrophenyl, lower alkoxy phenyl having 1 to 4 carbon atoms in the alkoxy, methylenedioxy phenyl, sulfamyl phenyl, or phenyl mono- or di-substituted with fluoro, chloro, or trifluoromethyl, except that only one of R.sup.2 - R.sup.7 is phenyl or substituted phenyl;
- and R.sup.8 - R.sup.11, which may be the same or different, are hydrogen, fluorine, chlorine, bromine, lower alkyl having 1 to 4 carbon atoms, lower alkoxy having 1 to 4 carbon atoms, or trifluoromethyl, except that R.sup.10 is other than hydrogen;
- which comprises reacting a compound of the formula ##SPC6##
- with a compound of the formula ##SPC7##
- in a water-miscible solvent and in the presence of a mineral acid.
Dependencies are inferred from the claim text.