Chromone compounds and preparation thereof

Details Chromone compounds and preparation thereof Chromone compounds and preparation thereof

1977-04-19

1978-08-08

Randolph, John D.

Drug, bio-affecting and body treating compositions

Nonspecific immunoeffector, per se ; or nonspecific...

Lipid or oil

2603452, C07D40714, A61K 3134

Patent

active

041057813

ABSTRACT:
Chromone compounds having the structure ##STR1## wherein R is aryl, substituted aryl, thienyl, furyl or pyridyl, Y is hydroxy (lower) alkylene, R.sub.1 is hydrogen, lower alkyl, aryl, substituted aryl or a heterocyclic group, R.sub.2 is hydrogen or lower alkoxy, Y.sub.1 is lower alkylene or hydroxyl (lower) alkylene, Z is oxygen or sulfur and R.sub.3 is hydrogen, lower alkyl, aryl, substituted aryl, or ar (lower) alkyl have anti-allergic activity and are useful in the treatment of asthma. Compounds of the structure [I] are prepared by reacting ##STR2## wherein Y' is hydroxy (lower) alkylene whose hydroxy group is optimally protected or a reactive derivative of [II] with a carboxylic acid of the formula R--COOH in the presence of a basic catalyst. The resulting compound is then reacted with an acid. Compounds of the structure [I'] are prepared by reacting the compound ##STR3## with the compound X--Y.sub.1 '--Z--R.sub.3 ' wherein X is an acid residue, Y' is lower alkylene or hydroxy (lower) alkylene whose hydroxy group is optionally protected by a protective group, R.sub.3 ' is hydrogen, lower alkyl, aryl, substituted aryl, or ar (lower) alkyl and Z is as defined above. When R.sub.3 ' is hydrogen, --Z--R.sub.3 ' is optionally protected by a protective group. The resultant compound is subjected to an elimination reaction when Y' is a protected group or when --Z--R.sub.3 ' is protected to split off the protective group.

REFERENCES:
patent: 3419578 (1968-12-01), Fitzmaurice et al.
patent: 3862175 (1975-01-01), Fitzmaurice et al.
patent: 3965122 (1976-06-01), Umio et al.
patent: 4049664 (1977-09-01), Umio et al.
Burger, Medicinal Chemistry, 2nd Ed., pp. 79 to 81, Interscience Publishers, Inc., 1960, (N.Y.).
Chemical Abstracts, vol. 67, abst. No. 100002d, (abst. of Neth. Appl. 6,603,997), 1967.
Klosa et al., Chem. Abstracts, vol. 60, col. 5441b, 1964.
Devitt et al., Chem. Abstracts, vol. 56, cols. 14189 to 14190, (1962).
Farkas et al., Chem. Abstracts, vol. 70, abst. 68066b, (1969).

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