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3,3-biarylpiperidine and 2,2-biarylmorpholine derivatives

  • US 6,503,905 B1
  • Filed: 08/06/1999
  • Issued: 01/07/2003
  • Est. Priority Date: 12/29/1998
  • Status: Expired due to Fees
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1. A compound of the formula embedded imagewherein,Q is oxygen or CH2;

  • R1 is hydrogen, (C0-C8)alkoxy-(C1-C8)alkyl-, wherein the total number of carbon atoms is eight or less, aryl, aryl-(C1-C8)alkyl-, heteroaryl, heteroaryl-(C1-C8)alkyl-, heterocyclic, heterocyclic-(C1-C8)alkyl, (C3-C7)cycloalkyl-, or (C3-C7)cycloalkyl-(C1-C8)alkyl, wherein said aryl and the aryl moiety of said aryl-(C1-C8)alkyl- are selected, independently, from phenyl and napthyl, and wherein said heteroaryl and the heteroaryl moiety of said heteroaryl-(C1-C8)alkyl- are selected, independently, from pyrazinyl, benzofuranyl, quinolyl, isoquinolyl, benzothienyl, isobenzofliryl, pyrazolyl, indolyl, isoindolyl, benzimidazolyl, purinyl, carbazolyl, 1,2,5-thiadiazolyl, quinazolinyl, pyridazinyl, pyrazinyl, cinnolinyl, phthalazinyl, quinoxalinyl, xanthinyl, hypoxanthinyl, pteridinyl, 5-azacytidinyl, 5-azauracilyl, triazolopyridinyl, imidazolopyridinyl, pyrrolopyrimidinyl, pyrazolopyrimidinyl, oxazolyl, oxadiazoyl, isoxazoyl, thiazolyl, isothiazolyl, furanyl, pyrazolyl, pyrrolyl, tetrazolyl, triazolyl, thienyl, imidazolyl, pyridinyl, and pyrimidinyl; and

    wherein said heterocyclic and the heterocyclic moiety of said heterocyclic-(C1-C8)alkyl- are selected from saturated or unsaturated nonaromatic monocyclic or bicyclic ring systems, wherein said monocyclic ring systems contain from four to seven ring carbon atoms, from one to three of which may optionally be replaced with O, N or S, and wherein said bicyclic ring systems contain from seven to twelve ring carbon atoms, from one to four of which may optionally be replaced with O, N or S; and

    wherein any of the aryl, heteroaryl or heterocyclic moieties of R1 may optionally be substituted with from one to three substitutuents independently selected from halo, (C1-C6)alkyl optionally substituted with from one to seven fluorine atoms, phenyl, benzyl, hydroxy, acetyl, amino, cyano, nitro, (C1-C6)alkoxy, (C1-C6)alkylamino and [(C1-C6)alkyl]2amino, and wherein any of the alkyl moieties within the alkyl, alkoxy or alkylamino groups of R1 may optionally be substituted with from one to seven fluorine atoms;

    where Q is oxygen, R2 is aryl, heteroaryl, heterocyclic, SO2R4, COR4, CONR5R6, COOR4, or C(OH)R5R6 wherein each of R4, R5 and R6 is defined, independently, as R1 is defined above, or R5 and R6, together with the carbon or nitrogen to which they are both attached, form a three to seven membered saturated ring containing from zero to three heterocarbons selected, independently, from O, N and S, and wherein said aryl, heteroaryl, and heterocyclic are defined as such terms are defined above in the definition of R1, and wherein any of the aryl, heteroaryl and heterocyclic moieties of R2 may optionally be substituted with from one to three substitutuents, independently selected from halo, (C1-C6)alkyl optionally substituted with from one to seven fluorine atoms, phenyl, benzyl, hydroxy, acetyl, amino, cyano, nitro, (C1-C6)alkoxy optionally substituted with from one to seven fluorine atoms, (C1-C6)alkylamino and [(C1-C6)alkyl]2amino;

    where Q is CH2, R2 is selected from C(OH)(C2H5)2, CONCH3(CH2CH3), CON(C2H5)2 and the following cyclic groups;

    embedded imageR3 is hydroxy, —

    NHSO2R7, —

    C(OH)R7R8, —

    OC(═

    O)R7, fluorine or —

    CONHR7, wherein R7 and R8 are the same or different and are selected from hydrogen, (C1-C4)alkyl, (C1-C4)alkoxy and (C1-C4)alkoxy-(C1-C4)alkyl having a total of four or less carbon atoms, and wherein any of the alkyl moieties of R7 and R8 may optionally be substituted with from one to seven fluorine atoms;

    X is CH or N; and

    Z1 and Z2 are selected, independently, from hydrogen, halo and (C1-C5)alkyl;

    with the proviso that there are no two adjacent ring oxygen atoms and no ring oxygen atom adjacent to either a ring nitrogen atom or a ring sulfur atom in any of the heterocyclic or heteroaryl moieties of formula I;

    or a pharmaceutically acceptable salt of such compound.

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