NOVEL DISUBSTITUTED XANTHONE CARBOXYLIC ACID COMPOUNDS

摘要

1384145 Disubstituted xanthone carboxylic acid compounds SYNTEX CORP 12 July 1972 [12 Jan 1972] 32536/72 Heading C2C The invention comprises compounds of the formulµ wherein each R1 is C 1 -C 5 alkyl or C 3 -C 5 cycloalkyl, each R2 is C 1 -C 5 alkoxy or C 3 -C 5 cycloalkoxy and one R3 is the same as R1 and the other is the same as R2; and esters, amides and salts thereof. They may be obtained by (1) condensing an o,p-disubstituted phenol wherein the substituents are alkyl, cycloalkyl, alkoxy or cycloalkoxy, with a 1,3-dicarbalkoxy-4- halobenzene in the presence of Cu 2 O to give the corresponding 1,3 - dicarbalkoxy - 4 - (o,pdisubstituted phenylozy)-benzene, base hydrolysing the latter to give the corresponding 1,3- dicarbozy - 4 - (o,p - disubstituted phenyloxy)- benzene, and cyclizing the latter to give the corresponding 5,7-disubstituted xanthone-2-carboxylic acid; or (2) condensing an o,p-dialkoxyphenol with a 1,3-dimethyl-4-halobenzene in the presence of Cu 2 O to give the corresponding 1,3 - dimethyl - 4 - (o,p - dialkoxyphenoxy)- benzene, oxidizing the latter to give the corresponding 1,3 - dicarboxy - 4 - (o,p - dialkoxyphenoxy)-benzene and cyclizing the latter to give the corresponding 5,7-dialkoxy-xanthone-2-carboxylic acids, (3) optionally converting a product of step (1) and (2) to its corresponding non-toxic esters, amides and salts and when either or both of the substituents in step (1) are methoxy groups, optionally further hydrolysing said methoxy group in the product and treating the resulting phenolic product with an alkyl (or cycloalkyl) halide in the presence of base optionally followed by further hydrolysis to yield the free carboxylic acid products. Examples are given for the production of the compounds. The above compounds are useful for inhibiting the effects of allergic reactions, also as smooth muscle relaxants or vasodilators. They may be administered orally, topically, parenterally, or by inhalation and in the form of either solid, liquid or gaseous doses, including tablets, suspensions and aerosols, optionally in conjunction with other pharmaceutical agents, e.g. antibiotics and hormonal agents.