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1,2-Bis-(substituted-phenyl)-2-propen-1-ones and pharmaceutical compositions thereof

  • US 20060063828A1
  • Filed: 06/28/2005
  • Published: 03/23/2006
  • Est. Priority Date: 06/28/2004
  • Status: Abandoned Application
First Claim
Patent Images

1. A compound of Formula I embedded image or its pharmaceutically acceptable salt or ester, wherein:

  • R

    , R


    , R

    , R

    , R

    , R

    , R

    , R

    , R

    and R

    are independently selected from the group consisting of hydrogen, halogen, nitro, alkyl, lower alkyl, alkenyl, alkynyl, carbocycle, cycloalkyl, cycloalkylalkyl, haloalkyl, aryl, arylalkyl, heteroaryl, heteroaryl lower alkyl, heterocyclic, heterocyclic lower alkyl, alkylthioalkyl, cycloalkylthioalkyl, arylthio lower alkyl, aralkyl lower thioalkyl, heteroarylthio lower alkyl, heteroaralkyl lower thioalkyl, heterocyclicthio lower alkyl, heterocyclicalkyl lower thioalkyl, lower alkyl S(O)-lower alkyl, lower alkyl-S(O)2-lower alkyl, arylsulfinyl lower alkyl, arylsulfonyl lower alkyl, —

    C(O)R2, R2C(O)alkyl, aminoalkyl, cycloalkylaminoalkyl, arylamino lower alkyl, heteroarylamino lower alkyl, heterocyclicamino lower alkyl, hydroxyl, hydroxyalkyl, alditol, carbohydrate, polyol alkyl, alkoxy, lower alkoxy, —

    (O(CH2)2)1-3

    O-lower alkyl, polyoxyalkylene, cycloalkyloxy, cycloalkylalkoxy, haloalkoxy, aryloxy, arylalkoxy, heteroaryloxy, heteroarylalkoxy, heteroaryl lower alkoxy, heterocyclicoxy, heterocyclicalkoxy, heterocyclic lower alkoxy, —

    OC(R1)2C(O)OH, —

    OC(R1)2C(O)OR2, —

    OC(R1)2C(O)NH2, —

    OC(R1)2C(O)NHR2, —

    OC(R1)2C(O)N(R2)2, —

    OC(R1)2C(O)NR7R8, amino, alkylamino, acylamino, dialkylamino, cycloalkylamino, arylamino, aralkylamino, heteroarylamino, heteroaralkylamino, heterocyclicamino, heterocyclicalkylamino, —

    NHR2, N(R2)2, —

    NR7R8, —

    NHC(R1)2C(O)OH, —

    NHC(R1)2C(O)OR2, —

    NHC(O)R2, —

    N(R2)C(O)R2, —

    NHC(O)OR2, —

    NHC(O)SR2, —

    NHSO2NHR2, —

    NHSO2R2, —

    NHSO2NR7R8, —

    N(C(O)NHR2)2, —

    NR2SO2R2, —

    NHC(O)NHR2, —

    NHC(O)NR7R8, —

    NHC(O)N(R2)2, thiol, alkylthio, cycloalkylthio, cycloalkylalkylthio, haloalkylthio, arylthio, aralkylthio, heteroarylthio, heteroaralkylthio, heterocyclicthio, heterocyclicalkylthio, alkylsulfonyl, arylsulfonyl, haloalkylsulfonyl, —

    SC(R1)2C(O)OH, —

    SC(R1)2C(O)OR2, —

    SCH2C(O)OH, —

    SCF2C(O)OH, —

    SO2NH2, —

    SO2NHR2, —

    SO2N(R2)2, SO2NR7R8, —

    SO2NHC(O)R2, —

    SR2, —

    SO2NHC(O)NHR2, —

    SO2NHC(O)N(R2) 2, —

    SO2NHC(O)NR7R8, sulfonic acid, sulfonate, sulfate, sulfinic acid, sulfenic acid, cyano, tetrazol-5-yl, carboxy, —

    C(O)OR2, —

    C(O)NH2, —

    C(O)NHR2, —

    C(O)N(R2)2, —

    C(O)NR7R8, —

    C(O)NHC(O)R2, —

    C(O)NHC(O)NHR2, —

    C(O)NHC(O)N(R2)2, —

    C(O)NHC(O)NR7R8, —

    C(O)NHSO2R2, —

    C(O)NHSO2NHR2, —

    C(O)NHSO2N(R2), —

    C(O)NHSO2NR7R8

    C(CH3)2C(O)OH, —

    (CH2)yC(O)OH, wherein y is 1, 2, 3, 4, 5, or 6, —

    PO2H2, —

    PO3H2, —

    P(R2)O2H, and phosphate, all of which can be optionally substituted where possible by one or more selected from the group consisting of halo, alkyl, lower alkyl, alkenyl, cycloalkyl, acyl, hydroxy, hydroxyalkyl, heterocyclic, amino, aminoalkyl, —

    NR7R8, alkoxy, oxo, cyano, carboxy, carboxyalkyl, alkoxycarbonyl, —

    C(O)NR7R8, and —

    C(O)N(R2)2;

    R1 is independently selected from the group consisting of hydrogen, lower alkyl, carbocycle, cycloalkyl, aryl, heteroaryl, heterocyclic, arylalkyl, heteroarylalkyl, and heterocyclicalkyl, wherein all may be optionally substituted where possible by one or more selected from the group consisting of halo, alkyl, lower alkyl, alkenyl, cycloalkyl, acyl, hydroxy, hydroxyalkyl, heterocyclic, amino, aminoalkyl, —

    NR7R8, alkoxy, oxo, cyano, carboxy, carboxyalkyl, alkoxycarbonyl, —

    C(O)NR7R8, and —

    C(O)N(R2)2;

    R2 is independently selected from the group consisting of alkyl, lower alkyl, alkenyl, alkynyl, carbocycle, cycloalkyl, aryl, heteroaryl, heterocyclic, arylalkyl, heteroarylalkyl, and heterocyclicalkyl, wherein all may be substituted where possible by one or more selected from the group consisting of halo, alkyl, lower alkyl, alkenyl, cycloalkyl, acyl, hydroxy, hydroxyalkyl, heterocyclic, amino, aminoalkyl, —

    NR7R8, alkoxy, oxo, cyano, carboxy, carboxyalkyl, alkoxycarbonyl, —

    C(O)NR7R8, and —

    C(O)N(R2)2;

    R7 and R8 are independently selected from the group consisting of alkyl, alkenyl, heteroaryl and aryl and linked together forming a 4- to 12-membered monocyclic, bicylic, tricyclic or benzofused ring;

    wherein one of R

    , R

    , R

    , R

    or R

    , or one of R

    , R

    , R

    , R

    or R

    must be a carbon-carbon linked heterocyclic or heteroaryl;

    or R

    and R

    taken together or R

    and R

    taken together or R

    and R

    taken together, or R

    and R

    taken together or R

    and R

    taken together or R

    and R

    taken together form a heterocyclic or heteroaryl optionally substituted by one or more alkoxycarbonylalkyl, carboxyalkyl, hydroxyalkyl or aminoalkyl and optionally substituted where possible with one or more selected from the group consisting of hydroxy, alkyl, carboxy, hydroxyalkyl, carboxyalkyl, amino, cyano, alkoxy, alkoxycarbonyl, acyl, oxo, —

    NR7R8, and halo;

    or R

    and R

    taken together or R

    and R

    taken together or R

    and R

    taken together or R

    and R

    taken together or R

    and R

    taken together or R

    and R

    taken together form a 5- or 6-membered ring containing one nitrogen, which may optionally be substituted where possible with one or more selected from the group consisting of halo, alkyl, lower alkyl, cycloalkyl, acyl, hydroxy, hydroxyalkyl, heterocyclic, amino, aminoalkyl, —

    NR7R8, alkoxy, oxo, cyano, carboxy, carboxyalkyl, alkoxycarbonyl, —

    C(O)NR7R8, and —

    C(O)N(R2)2;

    wherein all R1, R2, R7 and R8 substituents can be optionally substituted where possible with one or more selected from the group consisting of halo, alkyl, lower alkyl, alkenyl, cycloalkyl, acyl, hydroxy, hydroxyalkyl, heterocyclic, amino, aminoalkyl, —

    NR7R8, alkoxy, oxo, cyano, carboxy, carboxyalkyl, alkoxycarbonyl, —

    C(O)NR7R8, and —

    C(O)N(R2)2.

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