1-(2-Substituted-chromonyloxy)-2-hydroxy-3-(substituted phenoxy)

Details 1-(2-Substituted-chromonyloxy)-2-hydroxy-3-(substituted phenoxy) 1-(2-Substituted-chromonyloxy)-2-hydroxy-3-(substituted phenoxy)

1973-12-03

1976-04-27

Drezin, Norman A.

Drug, bio-affecting and body treating compositions

Nonspecific immunoeffector, per se ; or nonspecific...

Lipid or oil

A61K 3135

Patent

active

039536041

ABSTRACT:
Definitions: in the following Formulae I, II and IV, R.sup.1 represents hydrogen, alkyl of 1 to 4 carbon atoms, or a nontoxic cation, while each of R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 symbolizes hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy, carbalkoxy of 1 to 4 carbon atoms, trihalomethyl, halogen, nitro or cyano.
Certain 1-(2-substituted-chromon-yloxy)-2-hydroxy-3-(substituted-phenoxy)propanes (Formula I), ##SPC1##
can be synthesized from intermediate bis-(substituted-phenoxy)propanes (Formula II), ##SPC2##
by condensation with diethyl oxalate in the presence of sodium ethoxide followed by cyclization with a mixture of glacial acetic acid and concentrated sulfuric or a mixture of concentrated hydrochloric acid and a lower alcohol containing up to 4 carbon atoms.
The bis-(substituted-phenoxy)propane intermediates (Formula II) are prepared by reacting a dihydroxyacetophenone (Formula III), ##SPC3##
with a (substituted-phenyl)glycidyl ether (Formula IV), ##SPC4##
in an organic solvent in the presence of a catalyst.
The 1-(2-substituted-chromon-yloxy)-2-hydroxy-3-(substituted-phenoxy)propanes (Formula I) are useful in the treatment of allergic conditions in mammals. The bis-(substituted-phenoxy)propanes (Formula II) are useful as intermediates in the synthesis of the latter compounds. Methods of preparing compounds having Formulae I and II are described. Methods of treating allergic conditions in mammals utilizing compounds of Formula I are also disclosed.

REFERENCES:
patent: 3519652 (1970-07-01), Fitzmaurice et al.
patent: 3673218 (1972-06-01), Cairns et al.
patent: 3792063 (1974-02-01), Cairns et al.
patent: 3823165 (1974-07-01), Cairns et al.
Physicians Desk Reference (PDR) 1974, p. 760.

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