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Urea derivatives and their use as ACAT inhibitors

  • US 5,621,010 A
  • Filed: 05/18/1994
  • Issued: 04/15/1997
  • Est. Priority Date: 05/21/1993
  • Status: Expired due to Fees
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First Claim
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1. A compound of formula (I) or a pharmaceutically acceptable salt thereof ##STR225## in which:

  • R1 and R2, which may be the same or different, each representsa hydrogen atom,a halogen atom,a straight or branched (C1 -C6)alkyl group ora straight or branched (C1 -C6)alkoxy group,R3 and R4, which may be the same or different, each representsa hydrogen atom,a straight or branched (C1 -C12)alkyl group,a straight or branched (C2 -C20)alkenyl group,a (C1 -C6)alkoxy(C1 -C6)alkyl group,a (C1 -C6)alkoxycarbonyl (C1 -C9)alkyl group,a benzyloxycarbonyl(C1 -C6)alkyl group in which the alkyl moiety is optionally substituted by phenyl,a N,N-di(C1 -C6)alkylamino(C1 -C6)alkyl group,a N-(C1 -C6)alkyl-N-benzylamino(C1 -C6)alkyl group,a (C1 -C6)alkylthio(C1 -C6)alkyl group,an oxo(C1 -C9)alkyl group,a hydroxy(C1 -C6)alkyl group,a dihydroxy(C1 -C6)alkyl group,a cyclo(C3 -C15)alkyl group,a cyclo(C3 -C8)alkyl(C1 -C6)alkyl group,a dicyclo(C3 -C9)alkyl(C1 -C6)alkyl group,a bicyclo(C6 -C9)alkyl group,a tricyclo(C9 -C12)alkyl group,in which in all cases the cycloalkyl group or the cycloalkyl moiety is optionally substituted by one or two substituents selected from the group consisting of (C1 -C6)alkyl, hydroxy, amino, acetoxy, acetamido, phenyl, benzyloxy, dimethylaminophenyl, and methylenedioxyphenyl, which may be further fused with a benzene ring,an aryl group,an aryl(C1 -C6)alkyl group,a diaryl(C1 -C6)alkyl group,in which in all cases the aryl group or the aryl moiety is optionally substituted by one, two or three substituents selected from the group consisting of (C1 -C6)alkyl, (C1 -C6)alkyloxy, halogen, nitro, hydroxy, amino, dimethylamino, methylenedioxy, and pyrrolidinyl,a heterocyclic group ora heterocyclic group attached to a (C1 -C6)alkylene chain,in which in all cases the heterocyclic group represents a saturated or unsaturated, 5 to 8 membered ring monocyclic or bicyclic, heterocyclic group containing 1 to 3 heteroatoms selected from the group consisting of S, O and N, and the heterocyclic group is optionally substituted by one or two substituents selected from the group consisting of acetyl, hydroxy, (C1 -C9)alkyl, (C1 -C9)alkyloxy, cyclo(C3 -C8)alkyl, cyclo(C3 -C9)alkyl(C3 -C10)alkyl, pyridyl(C1 -C6)alkyl, phenyl, phenyl(C1 -C6)alkyl, diphenyl (C1 -C6)alkyl, and phenylpiperazinyl, the phenyl group or the phenyl moiety being optionally substituted by one or two substituents selected from the group consisting of halogen, hydroxy, (C1 -C6)alkyl, (C1 -C6)alkoxy, cyano, diethylamino and trifluoromethyl, which may be further fused with a benzene ring,and further R3 and R4, together with the nitrogen atom to which they are attached, may form a saturated or unsaturated heterocyclic group,in which the heterocyclic group represents a 5 to 8 membered ring monocyclic or bicyclic, heterocyclic group or a group derived from a heterocyclic spiro compound, which may contain one or two heteroatoms selected from the group consisting of S, O or N, the heterocyclic group being optionally substituted by one or two substituents selected from the group consisting of (C1 -C6)alkyl, hydroxy, hydroxy(C1 -C6)alkyl, (C1 -C6)alkoxy(C1 -C6)alkyl, acetoxy(C1 -C6)alkyl, (C1 -C9)alkylcarbonyl, (C1 -C6)alkoxycarbonyl, amino, tosyl, phenyl, halogenophenyl, (C1 -C6)alkoxyphenyl, phenyl(C1 -C6)alkyl, benzyloxy, benzyloxy(C1 -C6)alkyl, tolyl, xylyl, benzoyl, methylenedioxyphenyl(C1 -C6)alkyl, pyridyl, pyridylcarbonyl, piperidyl, pyrrolidinyl (C1 -C6)alkyl and pyrrolidinylcarbonyl(C1 -C6)alkyl, which may be further fused with a benzene ring,in which in all cases the alkyl and alkoxy moieties may be either straight or branched,with the proviso that both R3 and R4 do not represent a hydrogen atom at the same time;

    R5 and R6, which may be the same or different, each represents a straight or branched (C1 -C6)alkyl group; and

    the line ##STR226## represents --CH2 CH2 -- or --CH═

    CH--.

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