59456-03-0Relevant articles and documents
Synthesis of 1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c]pyridin-5-ones. I. 3-Unsubstituted compounds
Connor,Unangst,Schwender,et al.
, p. 1557 - 1559 (1984)
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3-(Aminoalkyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c]pyridin-5-ones as potential anticholinergic bronchodilators
Connor,Unangst,Schwender,Sorenson,Carethers,Puchalski,Brown,Finkel
, p. 683 - 688 (2007/10/02)
A series of 3-(aminoalkyl)-benzopyrano[3,4-c]pyridin-5-ones was prepared and tested as potential orally active anticholinergic bronchodilators. Inhibition of methacholine-induced collapse in guinea pigs and inhibition of pilocarpine-induced bronchoconstriction in dogs were served as in vivo models. Simultaneous measurement of salivary inhibition in the dog model allowed determination of a pulmonary selectivity ratio. The benzopyrano[3,4-c]pyridin-5-one parent ring system was prepared by Pechman condensation of phenols with a piperidine β-keto ester. Alkylation with aminoalkyl halides, or with 1-chloro-2-propanone followed by reductive amination, yielded the 3-substituted target compounds. Bronchodilator potency was related to the extent of steric crowding surrounding the side-chain terminal amine function. Addition of a methyl substituent on the carbon α to the terminal amine often increased potency or pulmonary selectivity. After secondary pharmacological evaluation, compound 7a, designated CI-923, was selected for clinical trial as a bronchodilator.
Bronchodilating piperidinoethyl benzopyranopyridinones
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, (2008/06/13)
Disclosed are novel substituted benzopyranopyridines which are active as bronchodilators.
