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Substituted pipecolinic acid derivatives as HIV protease inhibitors

  • US 5,614,533 A
  • Filed: 11/09/1994
  • Issued: 03/25/1997
  • Est. Priority Date: 03/13/1987
  • Status: Expired due to Term
First Claim
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1. A compound of formula 1 ##STR7## wherein X is R3 OC(O), R3 C(O) or R3 NR4 C(O) wherein R3 is 2-quinolinyl or 3-quinolinyl, andR4 is hydrogen or lower alkyl;

  • B is absent or the divalent radical --NHCHR5 C(O)-- wherein R5 is lower alkyl;

    lower cycloalkyl;

    (lower cycloalkyl)-(lower alkyl);

    phenylmethyl;

    or lower alkyl monosubstituted with hydroxy, carboxy, lower alkoxycarbonyl, aminocarbonyl, (lower alkyl)aminocarbonyl or di(lower alkyl)aminocarbonyl;

    R1 is hydrogen, halo, hydroxy, lower alkyl or lower alkoxy;

    R2 is lower alkyl; and

    Y is lower alkyl;

    lower cycloalkyl;

    phenyl or phenyl monosubstituted with halo, hydroxy, lower alkyl or lower alkoxy;

    phenylmethyl or phenylmethyl monosubstituted with halo, hydroxy, lower alkyl or lower alkoxy;

    orY is W(CH2)n Z wherein W is oxo, thio, sulfinyl or sulfonyl, Z is lower alkyl;

    phenyl or phenyl monosubstituted with halo, hydroxy, lower alkyl or lower alkoxy;

    or (Het); and

    n is zero or one;

    wherein the term "lower alkyl" as used herein, either alone or in combination with another radical, means a straight chain alkyl radical containing one to six carbon atoms or a branched chain alkyl radical containing three to four carbon atoms;

    wherein the term "lower cycloalkyl" as used herein, either alone or in combination with another radical, means a saturated cyclic hydrocarbon radical containing from three to six carbon atoms;

    wherein the term "lower alkoxy" as used herein means a straight chain alkoxy radical containing one to six carbon atoms or a branched chain alkoxy radical containing three to four carbon atoms;

    wherein the term "halo" as used herein means a halo radical selected from bromo, chloro, fluoro and iodo; and

    ,wherein (Het) as used herein means a monovalent radical derived by removal of a hydrogen from a five or six membered saturated or unsaturated heterocycle selected from the group consisting of furan, thiophene, pyrrolidine, tetrahydrofuran, thiazolidine, pyrrole, 1H-imidazole, 1-methyl-1H-imidazole, isoxazole, thiazole, 2-methylthiazole, 2-aminothiazole, piperidine, 1,4-dioxane, morpholine, pyridine, 2-methylpyridine, pyrimidine, 4-methylpyrimidine, 2,4-dimethylpyrimidine, 2,6-dimethylpyrimidine and 4,6-dimethylpyrimidine;

    or a therapeutically acceptable acid addition salt thereof.

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