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Heterocyclic compounds

  • US 6,803,362 B2
  • Filed: 03/08/2002
  • Issued: 10/12/2004
  • Est. Priority Date: 03/09/2001
  • Status: Active Grant
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Assignment
First Claim
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1. A compound of formula (I) wherein:

  • embedded imageWherein R1 is Ra, RaRb—

    , Ra—

    O—

    Rb—

    , or (Rc)(Rd)N—

    Rb—

    , where Ra is H, cyano, —

    (C═

    O)N(Rc)(Rd), —

    C(═

    NH)(NH2), C1-10 alkyl, C3-8 alkenyl, C3-8 cycloalkyl, C2-5 heterocyclic radical, or phenyl;

    where Rb is C1-8 alkylene, C2-8 alkenylene, C3-8 cycloalkylene, bivalent C3-8 heterocyclic radical, or phenylene; and

    Rc and Rd are each independently H, C1-8 alkyl, C2-8 alkenyl, C3-8 cycloalkyl, or phenyl;

    R2′

    is H, methyl, ethyl, NRpRq, —

    (CO)NRpRq, —

    (CO)ORr, —

    CH2NRpRq, or CH2ORr;

    where Rp, Rq, and Rr are independently selected from C1-6 alkyl, C3-6 cycloalkyl, phenyl;

    (C3-6 cycloalkyl)(C1-2 alkylene), benzyl or phenethyl;

    or Rp and Rq taken together with the nitrogen to which they are attached, form a 4-7 membered heterocyclic ring with 0 or 1 additional heteroatoms selected from O, S, and N;

    R3′

    is H, methyl, ethyl, NRsRt, —

    (CO)NRsRt, —

    (CO)ORu, —

    CH2NRsRt, or CH2ORu;

    where Rs, Rt, and Ru are independently selected from C1-6 alkyl, C3-6 cycloalkyl, phenyl;

    (C3-6 cycloalkyl)(C1-2 uualkylene), benzyl or phenethyl;

    or Rs and R1 taken together with the nitrogen to which they are attached, form a 4-7 membered heterocyclic ring with 0 or 1 additional heteroatoms selected from O, S, and N;

    R5′

    is methyl, ethyl, or H;

    R6′

    is methyl, ethyl, or H;

    R7′

    is methyl, ethyl, or H;

    R3 is F, Cl, Br, CHO, Rf, RfRg—

    , Rf—

    O—

    Rg—

    , or (Rh)(Ri)N—

    Rg—

    , where Rf is H, C 1-6alkyl, C2-6alkenyl, C3-6cycloalkyl, C2-5heterocyclic radical, or phenyl;

    where Rg is C1-6alkylene, C2-6alkenylene, C3-6cycloalkylene, bivalent C3-6heterocyclic radical, or phenylene; and

    Rh and Ri are each independently H, C1-6alkyl, C2-6alkenyl, C3-6cycloalkyl, or phenyl;

    Re is H or C1-6 alkyl;

    each of R4 and R6 is independently H, F, Cl, Br, I, COOH, OH, nitro, amino, cyano, C1-4alkoxy, or C1-4alkyl;

    R5 is H, F, Cl, Br, I, (C═

    O)Rj, OH, nitro, NRjRk, cyano, phenyl, —

    OCH2—

    Ph, C1-4alkoxy, or C1-4alkyl;

    R7 is H, F, Cl, Br, I, (C═

    O)Rm, OH, nitro, NRlRm, cyano, phenyl, —

    OCH2—

    Ph C1-4alkoxy, or C1-4alkyl;

    wherein each of Rj, Rk, Rl, and Rm is independently selected from H, C1-6 alkyl, hydroxy, phenyl, benzyl, phenethyl, and C1-6 alkoxy;

    each of the above hydrocarbyl (including alkyl, alkoxy, phenyl, benzyl, cycloalkyl, and so on) or heterocyclic groups being independently and optionally substituted with between 1 and 3 substituents selected from C1-3 alkyl, halo, hydroxy, amino, and C1-3 alkoxy;

    wherein n is 0, 1, or 2;

    where n is 2, the moiety —

    (CHR5′

    )n=2—

    is —

    (CHR5′

    —

    CHR7′

    )—

    where CHR5′

    is between CHR6′ and

    CHR7′

    ;

    provided at least one of R1, R2′

    , R3, R4, R5, R6, and R7 is other than H;

    and provided, where n=1, and each of R4, R5, R6, R7, R2′

    , R3′

    , R5′

    , and R6′

    is H, then (a) where Re is H, then R1 is not methyl, pyridyl, phenyl, or benzyl;

    and provided, where Re is H, n=1, R1 is methyl, and each of R4, R6, R7, R2′

    , R3′

    , R5′

    , and R6′

    is H, then R5 is not methoxy;

    or a pharmaceutically acceptable salt, ester, or amide thereof.

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