N-[[(2,6-disubstituted)phenyl]-N'-diarylalkyl] ureas as antihyperlipidemic and antiatherosclerotic agents

Claim 1

A method of preparing a compound having the structural formula wherein R₁ and R₂ are independently selected from alkyl of from one to six carbon atoms, alkoxy of from one to six carbon atoms; n is zero or an integer of from one to four; n′ is zero or an integer of from one to three; X is oxygen or sulfur; Ar an Ar′ are independently unsubstituted phenyl, 1- or 2-naphthyl, 2- or 3-thienyl, or 2-, 3-, or 4-pyridinyl; or phenyl, 1- or 2-naphthyl, 2- or 3-thienyl, or 2-, 3-, or 4-pyridinyl substituted with alkyl of from one to six carbon atoms, hydroxy, alkoxy of from one to six carbon atoms, fluorine, chlorine, bromine, nitro, benzyloxy, trifluoromethyl, or -NR₅R₆ in which R₅ and R₆ are independently hydrogen or alkyl of from one to six carbon atoms; or NH-acetyl with the proviso that when Ar and Ar′ are both not phenyl or substituted phenyl, n is one and n′ is zero; or a pharmaceutically acceptable salt thereof comprising the steps of reacting an isocyanate or thioisocyanate having the formula wherein X, R₁ and R₂ are as defined above with an amine having the formula wherein n, n′, Ar and Ar′ are as defined above, and thereafter isolating the product of said reaction by conventional means and converting, if desired, said product to a pharmaceutically acceptable salt by conventional means.

Claim 2

A method of preparing a compound having the structural formula wherein R₁ and R₂ are independently selected from alkyl of from one to six carbon atoms, alkoxy of from one to six carbon atoms; n is zero or an integer of from one to four; n′ is zero or an integer of from one to three; X is oxygen or sulfur; Ar an Ar′ are independently unsubstituted phenyl, 1- or 2-naphthyl, 2- or 3-thienyl, or 2-, 3-, or 4-pyridinyl; or phenyl, 1- or 2-naphthyl, 2- or 3-thienyl, or 2-, 3-, or 4-pyridinyl substituted with alkyl of from one to six carbon atoms, hydroxy, alkoxy of from one to six carbon atoms, fluorine, chlorine, bromine, nitro, benzyloxy, trifluoromethyl, or -NR₅R₆ in which R₅ and R₆ are independently hydrogen or alkyl of from one to six carbon atoms; or NH-acetyl with the proviso that when Ar and Ar′ are both not phenyl or substituted phenyl, n is one and n′ is zero; or a pharmaceutically acceptable salt thereof comprising the steps of reacting an isocyanate or thioisocyanate having the formula wherein X, R₁ and R₂ are as defined above with an amine having the formula wherein n, n′, Ar and Ar′ are as defined above, and thereafter isolating the product of said reaction by conventional means and converting, if desired, said product to a pharmaceutically acceptable salt by conventional means.