96686-71-4Relevant academic research and scientific papers
3,4-Dihydro-2H-1-benzopyran-2-carboxylic Acids and Related Compounds as Leukotriene Antagonists
Cohen, Noal,Weber, Giuseppe,Banner, Bruce L.,Lopresti, Rocco J.,Schaer, Beatrice,et al.
, p. 1842 - 1860 (2007/10/02)
Evaluation of a series of 3,4-dihydro-2H-1-benzopyran-2-carboxylic acids linked to the 2-hydroxyacetophenone pharmacophore present in the standard peptidoleukotriene antagonist FPL 55712 (1) has led to the discovery of Ro 23-3544 (7), an antagonist possessing greater potency and duration of action vs LTD4 than the standard (aerosol route of administration, guinea pig bronchoconstriction model).Interestingly, this compound also potently inhibited bronchoconstriction induced by LTB4 whereas 1 did not.Attempts to establish structure-activity relationships in this series involved modifications in the 2-hydroxyacetophenone moiety, the linking chain, and the chroman system.All variations produced analogues which were either inactive or possessed reduced potency relative to acid 7.Optical resolution of 7 was achieved by two methods.Absolute configurations of the enantiomers were determined via X-ray crystallographic analyses of an intermediate as well as a salt of the S enantiomer.Although the enantiommers exhibited similar potencies in in vitro assays and in vivo when administered intravenously, significant differences were observed in the guinea pig bronchoconstriction model vs LTC4 and LTD4 when administered by the aerosol route (S antipode 15-fold more potent).The properties of 7 have been compared with several recently reported leukotriene antagonists.
3,4-dihydro-2H-1-benzopyran derivatives
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, (2008/06/13)
The invention relates to compounds of the formula STR1 wherein R1 is hydrogen or lower alkyl; R2 is hydrogen or halogen; R3, R4 and R5 are hydrogen, acyl or lower alkyl; R6 and R7, independently, are hydrogen or lower alkyl; X is alkylene3-7 ; and n is an integer of zero to four; provided that only one of R3, R4 or R5 can be acyl; enantiomers thereof, and, when R7 is hydrogen, salts thereof with pharmaceutically acceptable bases. The compounds of formulas I and II are useful as agents for the treatment of allergic conditions.
