KR840006339A - Process for preparing 3-aryl-7-chloro-3,4-dihydroacridine-1,9 (2H, 10H) -dione-1-oxime and-1-hydrazone derivative - Google Patents

Abstract

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Description

Process for preparing 3-aryl-7-chloro-3,4-dihydroacridine-1,9 (2H, 10H) -dione-1-oxime and-1-hydrazone derivative

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Claims (6)

3-aryl-7-chloro-3,4-dihydroacridin-1,9 (2H, 10H) -dione of formula (II) is reacted with a compound of formula (III) or a salt thereof Accordingly, the reaction product is converted to an addition salt using a physiologically toxic acid or to an ammonium salt using an alkylating agent, so that 3-aryl-7-cycloyl-3,4-ditch of formula (I) A process for preparing droacridin-1,9 (2H, 10H) -dione 1-oxime and 1-hydrazone derivatives and their physiologically toxic acid addition and ammonium salts. Wherein R ¹ , R ² and R ³ are the same or different and are hydrogen, halogen, C ₁ -C ₄ alkyl, trifluoromethyl, C ₁ -C ₄ alkoxy, trifluoromethoxy, difluorochlorometh Methoxy, 1,1,2,2-tetrafluoroethoxy, phenoxy, halogenophenoxy, C ₁ -C ₄ alkylthio, phenylthio and naphthylthio, C ₁ -C ₄ alkylsulfinyl and naphthyl Sulfinyl, C ₁ -C ₄ alkylsulfonyl, phenylsulfonyl and naphthylsulfonyl, trifluoromethylthio, carbamyl, cyano or nitro a) X represents oxygen and Y represents a single bond and Z represents a straight or branched chain alkyl having 2 to 5 carbon atoms optionally substituted with a hydroxy group, or b) X, Y and Z represent a single bond or c) X represents an —NR— group where R is hydrogen or C ₁ -C ₄ alkyl, Y represents a single bond and Z represents a straight or branched chain alkylene having 2 to 5 carbon atoms d) X represents an —NR— group where R is hydrogen or C ₁ -C ₄ alkyl, Y represents a carbonyl, thiocarbonyl or iminocarbonyl group and Z represents a single bond or e) X represents a -NR- group where R is hydrogen or C ₁ -C ₄ alkyl, Y represents a carboxamido, thiocarboxamido or carboxamidino group and Z is a straight or branched chain having 2 to 5 carbon atoms Represent alkylene or f) X represents an —NR— group where R is hydrogen or C ₁ -C ₄ alkyl, Y represents a carbonyl group and Z represents a straight or branched chain alkylene having 1 to 3 carbon atoms or g) X represents an —NR— group where R is hydrogen or C ₁ -C ₄ alkyl, Y represents a carbonyl group and Z represents a straight or branched chain alkylene having 2 to 5 carbon atoms R ⁴ and R ⁵ are the same or different and represent hydrogen or straight or branched C ₁ -C ₄ alkyl or ⁴ together with R ⁴ and R ⁵ form a 5- to 7-membered heterocycle ring with a nitrogen atom; Alkylene chains having from 6 to 6 carbon atoms wherein one -CH ₂ -group can be substituted by another heteroatom in the group comprising nitrogen, oxygen or sulfur, the heterocycle ring being, in turn, a hydroxy group by optionally optionally substituted by methyl with 1 to 3 phenyl or -C ₁ -C ₃ carbon atoms, by an alkyl group having from alkyl or naphthyl -C ₁ -C ₃ alkyl or by a methyl, methoxy, chlorine or trifluoromethyl Substituted by substituted phenyl or naphthyl and R ⁶ represents hydrogen or a hydroxy group. A compound of formula (I) wherein R ¹ and R ² represent hydrogen, R ³ represents chlorine or trifluoromethyl, X, Y and Z represent a single bond and R ⁴ and R ⁵ are A method of representing a piperazine ring optionally substituted on nitrogen with a nitrogen atom. The compound of formula (I) according to claim 1, wherein the compound of formula (I) is 3- (4-trifluoromethylphenyl) -7-chloro-3,4-dihydroacridin-1,9 (2H, 10H) -dione 1- (N-methyl-N'-piperazinyl) -imine. The compound of formula (I) according to claim 1, wherein the compound of formula (I) is 3- (4-trifluoromethylphenyl) -7-chloro-3,4-dihydroacridin-1,9 (2H, 10H) -dione 1- N-2-hydroxyethyl-N'-piperazine imine. The compound of formula (I) according to claim 1, wherein the compound of formula (I) is 3- (4-chlorophenyl) -7-chloro-3,4-dihydroacridine-1,9 (2H, 10H) -dione 1-N- 2-methyl-N'-piperazine imine. The compound of formula (I) according to claim 1, wherein the compound of formula (I) is 3- (4-chlorophenyl) -7-chloro-3,4-dihydroacridine-1,9 (2H, 10H) -dione 1-N- 2-hydroxyethyl-N'-piperazine imine. ※ Note: The disclosure is based on the initial application.