Dibenzotropone- and dibenzosuberonecarboxylic acids with bronchodilator activity.
The syntheses of 44 5H-dibenzo[a,d]cyclohepten-5-one derivatives bearing a carboxyl gropu at the 1, 2, 3, or 10 position and various substituents at the 7, 8, or 9 position are described. Some of the compounds showed significant bronchodilator activity in guinea pigs and protected the animals against a histamine challenge administered either by aerosol or intravenously. The most active compounds were 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one-2-carboxylic acids bearing a methyl or halogen substituent at the 9 position. These compounds were approximately as active as aminophylline by intraperitoneal administration.
D000403:Airway Resistance / Q000187:drug effects; D000818:Animals; D001993:Bronchodilator Agents / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D005260:Female; D006168:Guinea Pigs; D006633:Histamine Antagonists; D066298:In Vitro Techniques; D013329:Structure-Activity Relationship; D014132:Trachea / Q000187:drug effects
D001993:Bronchodilator Agents; D002264:Carboxylic Acids; D006633:Histamine Antagonists