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Alkynl and azido-substituted 4-anilinoquinazolines

DC CAFC
  • US RE41,065 E1
  • Filed: 02/27/2008
  • Issued: 12/29/2009
  • Est. Priority Date: 06/06/1995
  • Status: Expired due to Term
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Assignment
First Claim
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1. A compound of the formula embedded imageor a pharmaceutically acceptable salt thereof wherein:

  • m is 1, 2, or 3;

    each R1 is independently selected from the group consisting of hydrogen, halo, hydroxy, hydroxyamino, carboxy, nitro, guanidino, ureido, cyano, trifluoromethyl, and -(C1-C4 alkylene)-W-(phenyl) wherein W is a single bond, O, S or NH;

    or each R1 is independently selected from R9 and C1-C4-alkyl substituted by cyano, wherein R9 is selected from the group consisting of R5, —

    OR6, —

    NR6R6, —

    C(O)R7, —

    NHOR5, —

    OC(O)R6, cyano, A and —

    YR5;

    R5 is C1-C4 alkyl;

    R6is independently hydrogen or R5;

    R7 is R5, —

    OR6 or —

    NR6R6;

    A is selected from piperidino, morpholino, pyrrolidino, 4-R6-piperazin-1-yl, imidazol-1-yl, 4-pyridon-1-yl, -(C1-C4 alkylene) (CO2H), phenoxy, phenyl, phenylsulfanyl, C2-C4 alkenyl, and -(C1-C4 alkylene)C(O)NR6R6; and

    Y is S, SO, or SO2;

    wherein the alkyl moieties in R5, —

    OR6 and —

    NR6R6 are optionally substituted by one to three halo substituents and the alkyl moieties in R5, —

    OR6 and —

    NR6R6 are optionally substituted by 1 or 2 R9 groups, and wherein the alkyl moieties of said optional substituents are optionally substituted by halo or R9, with the proviso that two heteroatoms are not attached to the same carbon atom;

    or each R1 is independently selected from —

    NHSO2R5, phthalimido-(C1-C4) -alkylsulfonylamino, benzamido, benzenesulfonylamino, 3-phenylureido, 2-oxopyrrolidin-1-yl, 2,5-dioxopyrrolidin-1-yl, and R10-(C2-C4) -alkanoylamino wherein R10 is selected from halo, —

    OR6, C2-C4 alkanoyloxy, —

    C(O)R7, and —

    NR6R6; and

    wherein said —

    NHSO2R5, phthalimido-(C1-C4-alkylsulfonylamino, benzamido, benzenesulfonylamino, 3-phenylureido, 2-oxopyrrolidin-1-yl, 2,5-dioxopyrrolidin-1-yl, and R10-(C2-C4)-alkanoylamino R1 groups are optionally substituted by 1 or 2 substituents independently selected from halo, C1-C4 alkyl, cyano, methanesulfonyl and C1-C4 alkoxy;

    or two R1 groups are taken together with the carbons to which they are attached to form a 5-8 membered ring that includes 1 or 2 heteroatoms selected from O, S and N;

    R2 is hydrogen or C1-C6 alkyl optionally substituted by 1 to 3 substituents independently selected from halo, C1-C4 alkoxy, —

    NR6R6, and —

    SO2R5;

    n is 1 or 2 and each R3 is independently selected from hydrogen, halo, hydroxy, C1-C6 alkyl, —

    NR6R6, and C1-C4 alkoxy, wherein the alkyl moieties of said R3 groups are optionally substituted by 1 to 3 substituents independently selected from halo, C1-C4 alkoxy, —

    NR6R6, and —

    SO2R5; and

    , R4 is azido or -(ethynyl)-R11 wherein R11 is hydrogen or C1-C6 alkyl optionally substituted by hydroxy, —

    OR6, or —

    NR6R6.

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