1286918 Indene derivatives MERCK & CO Inc 5 Aug 1970 [11 Aug 19691 37828/70 Heading C2C  Novel indenes of the general formula wherein R 1  is an aryl group, R 2  is a hydrogen or halogen atom or a hydroxy, C 1-5  alkyl, aryl, aralkyl, C 1-5  alkoxy, halo-C 1-5  alkyl, C 1-5  alkylthio, arylthio or C 2-5  alkenyl group, R 3  is a hydrogen atom or a C 1-5  alkyl group, R 4  is an acyl group, or R 3 , R 4  and the nitrogen atom to which they are attached together form a phthalimido group, R 5  is a methylene, ethylene, trimethylene or 1,2-propylene group, R 6  is a hydrogen or halogen atom or a C 1-5  alkyl, C 1-5  alkoxy, alkylthio or trifluoromethyl group and R 7  is a hydrogen or halogen atom or a hydroxy, C 1-5  alkyl, C 1-5  alkoxy, nitro, amino, C 1-5  alkylamino, di-C 1-5  alkylamino, C 1-6  alkanoylamino, C 1-6  alkanoyl, cyano, trifluoromethyl, di-C 1-5  alkylsulphamoyl, alkylsulphinyl, alkylsulphonyl, benzylthio, benzoyloxy, C 2-5  alkenyl or C 2 _ 5  alkenyloxy group, and pharmaceutically acceptable, non-toxic acid addition salts thereof are prepared by (a) reaction of the corresponding l-indenylalkyl tosylate with an amide of the general formula HNR 3 R 4  or (b) reaction of the corresponding l-indenylalkylamine with a suitable acylating agent, followed optionally by salification of the product.  l-Indenylalkylamines are prepared by reaction of an indene of the first general formula above wherein R 3 R 4 N is a phthalimido group with hydrazine hydrate. Indenyl-1-methanols are prepared by reaction of an indenyl-1-acetic acid of the general formula with pyridine oxide and acetic anhydride in benzene and reduction of the resulting corresponding indenyl - 1 - carboxaldehyde with sodium borohydride. 1-(1 -Indenyl)- 2-hydrory. propanes of the general formula are prepared by reaction of the corresponding 1-indenvlacetio acid with methyl lithium and reduction of the resulting 1-(1-indenyl)-2-propanone with sodium borohydride. 2-(1-Indenyl)- ethyl tosylates of the general formula wherein Ts is a tosyl group, are prepared by lithium aluminium hydride reduction of an indenyl-1-acetic acid of the general formula reaction of the resulting 2-(1-indenyl)-ethanol with an aldehyde of the general formula ArCHO in the presence of a strong base and reaction of the resulting 2-(3-substituted-1-indenyl)-ethanol of the general formula with tosyl chloride. 3-(1-Indenyl)-propionic acids  of the general formula are prepared by reaction of the corresponding 2 - (I . indenyl) - ethanol with tosyl chloride, followed by sodium cyanide; a strong base and finally an acid. 1-Indenyl-acetic acids of the sixth general formula above are prepared by heating a 3-phenylpropionic acid of the general formula with polyphosphoric acid and reacting the resulting indanone of the general formula with cyanoacetic acid, followed by alkaline hydrolysis. 3 - Phenylpropionic acids of the ninth general formula above are prepared (a) by reaction of a benzyl halide of the general formula wherein X is a halogen atom with a malonic acid diester of the general formula R 2 CH(COOE) 2 , wherein E is an esterifying group, in the presence of a strong base, and acid hydrolysis of the resulting benzylmalonic acid diester of the general formula or (b) by alkaline hydrolysis of a cinnamic acid ester of the general formula hydrogenation of the resulting corresponding cinnamic acid in the presence of palladium. Cinnamic acid esters of the immediately preceding general formula are prepared by reaction of a benzaldehyde of the general formula with a haloacetic acid ester of the general formula X-CHR 2 -COOE in the presence of sodium ethoxide in anhydrous ethanol. 3 - Phenyl - 3 - hydroxy - propionic acid esters of the general formula  are prepared by reaction of a benzaldehyde and a haloacetic acid ester as defined immediately above in the presence of zinc dust and an anhydrous solvent. Pharmaceutical compositions having antiinflammatory, antipyretic, analgesic and bactericidal activity comprise, as active ingredient, an indene derivative of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, together with a diluent or carrier, and may be administered topically, orally, rectally or parenterally.