Methods are disclosed for preparing compounds of Formula I: where R1, R3, and R4are independently
hydrogen or C1 to C4
alkyl, and R2 is: where R5 is selected from the group consisting of
hydrogen and C1 to C4
alkyl, or where R6, R7 and R8 are independently
hydrogen or C1 to C4
alkyl; or the esters or pharmacologically acceptable salts thereof. The methods can involve converting a suitably functionalized
aniline compound to a diazonium salt (which
aniline compound can be first formed by reduction of a
nitrobenzene) and
coupling the diazonium salt with a suitably functionalized
benzene compound. The suitably functionalized
aniline compound either includes a
primary alcohol or
aldehyde group, which is then oxidized to a
carboxylic acid group, or includes a
nitrile or
amide group, which is hydrolyzed to a
carboxylic acid group. The methods can also involve the
direct coupling (via reduction of nitro groups to form an azo linkage) of suitably functionalized nitrobenzenes. The compounds and or their metabolites can be used to treat or prevent various diseases, particularly inflammatory conditions of the GI tract.