The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Apr. 27, 1976
Filed:
Dec. 03, 1973
Brian Thomas Warren, Ickenham, EN;
John William Spicer, London, EN;
Miles Laboratories, Inc., Elkhart, IN (US);
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.