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Substituted 1-heteroaryl-4-substituted piperazine and piperidine analogues

  • US 20050239791A1
  • Filed: 04/06/2005
  • Published: 10/27/2005
  • Est. Priority Date: 04/07/2004
  • Status: Abandoned Application
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First Claim
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1. A compound of the formula embedded image or a pharmaceutically acceptable salt thereof, wherein:

  • V is absent or —

    (C═

    O)—

    . W is nitrogen, CH, or C—

    OH. Y1 and Y5 are independently CR or nitrogen. Y3 and Y4 are independently CR1 or nitrogen. Z is CR2 or nitrogen;

    such that no more than three of Y1, Y3, Z, Y4, and Y5 are nitrogen;

    Each R, R1, and R2 is independently (i) hydrogen, halogen, nitro, cyano, amino, carboxamide, imino, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C2-C6alkanoyl, C2-C6alkyloxime, C1-C6alkoxy, (C1-C6alkoxy)C1-C4alkyl, (C1-C6alkoxy)C1-C4alkoxy, C1-C6alkoxycarbonyl, C1-C6alkoxycarbonyl, mono- or di-C1-C6alkylcarboxamide, C1-C6alkylthio,C1-C6alkylsulfonyl, haloC1-C6alkyl, haloC1-C6alkoxy, hydroxyC1-C6alkyl, aminoC1-C6alkyl, or mono- or di-(C1-C6alkyl)aminoC0-C6alkyl, or (ii) (C3-C7cycloalkyl)C0-C6alkyl, (heterocycloalkyl)C0-C6alkyl, (phenyl)C0-C2alkyl, (phenyl)C0-C2alkoxy, (pyrrolyl)C0-C2alkyl, (thienyl)C0-C2alkyl, or (pyridyl)C0-C2alkyl;

    each of which is substituted with from 0 to 3 substituents independently chosen from halogen, C1-C2alkoxy, and C1-C2alkyl;

    or any two R1 and R2 may be taken together to form a fused 5- or 6-membered carbocycle or heterocycle, each of which is substituted with from 0 to 3 substituents independently chosen from halogen, hydroxy, nitro, cyano, amino, C1-C4alkyl, C1-C4alkoxy, haloC1-C4alkyl, and haloC1-C4alkoxy;

    n is 1 or 2;

    R3 is;

    (i) hydrogen, C1-C6alkyl, C2-C6alkenyl, or haloC1-C6alkyl;

    or (ii) taken together with one or both of R6 and R10 to form a fused carbocycle or heterocycle having one or two rings, wherein each ring contains from 5 to 8 ring members and 0, 1 or 2 heteroatoms. R4 is hydrogen, C1-C6alkyl, or haloC1-C6alkyl;

    Each R5 is independently;

    (i) hydrogen, halogen, hydroxy, nitro, cyano, amino, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxy, haloC1-C6alkyl, haloC1-C6alkoxy, mono- or di(C1-C6alkyl)amino, or aminoC1-C6alkyl;

    or (ii) taken together with R6 to form a fused 5- to 8-membered carbocycle or heterocycle or a methylene or ethylene bridge. R6 is;

    (i) hydrogen, halogen, hydroxy, nitro, cyano, amino, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxy, haloC1-C6alkyl, haloC1-C6alkoxy, mono- or di-(C1-C6alkyl)amino or aminoC1-C6alkyl, or (ii) taken together with R3 taken together with to form a fused carbocycle or heterocycle;

    or (iii) taken together with R5 to form a fused carbocycle or heterocycle or a methylene or ethylene bridge;

    P is N or CR7;

    Q is N or CR8;

    U is N or CR9;

    T is N or CR10;

    X is N or CR11;

    wherein at least one of P, Q, U, T, and X is nitrogen;

    when U or T is nitrogen at least one of P, Q, or X is also nitrogen, and when P or Q is nitrogen, at least one of U, T, and X is also nitrogen;

    R7 is;

    (i) hydrogen, halogen, hydroxy, nitro, cyano, —

    COOH, or a group of the formula L-M;

    or (ii) taken together with R8 or R12 to form a fused 5- or 6-membered carbocycle or heterocycle. R8 is;

    (i) hydrogen, halogen, hydroxy, nitro, cyano, —

    COOH, or a group of the formula L-M;

    or (ii) taken together with R7 to form a fused 5- or 6-membered carbocycle or heterocycle;

    R9 is;

    (i) hydrogen, halogen, hydroxy, nitro, cyano, —

    COOH, or a group of the formula L-M;

    or (ii) taken together with R10 or R11 to form a fused 5- to 10-membered carbocycle or heterocycle;

    R10 is;

    (i) hydrogen, halogen, hydroxy, nitro, cyano, —

    COOH, or a group of the formula L-M;

    or (ii) taken together with R3 or R9 to form a fused carbocycle or heterocycle;

    R11 is;

    (i) hydrogen, halogen, hydroxy, nitro, cyano, —

    COOH, or a group of the formula L-M;

    or (ii) taken together with R9 to form a fused carbocycle or heterocycle;

    R12 is;

    (i) hydrogen, halogen, hydroxy, nitro, cyano, amino, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxy, haloC1-C6alkyl, haloC1-C6alkoxy, mono- or di(C1-C6alkyl)amino, or aminoC1-C6alkyl;

    or (ii) taken together with R7 to form a fused carbocycle or heterocycle. Each L is independently a single covalent bond, N(R13), O, C(═

    O), SO2, SO2NH, C(═

    O)N(R13) or N(R13)C(═

    O) wherein each R13 is independently hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, or haloC1-C6alkyl; and

    Each M is independently hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, haloC1-C6alkyl, aminoC1-C6alkyl, or a 5- to 10-membered cycloalkyl or heterocycloalkyl;

    preferably M is other than hydrogen if L is a single covalent bond.

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