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Oxazolidinones Bearing Antimicrobial Activity Composition and Methods of Preparation

  • US 20090018123A1
  • Filed: 06/19/2006
  • Published: 01/15/2009
  • Est. Priority Date: 06/20/2005
  • Status: Abandoned Application
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First Claim
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1. An oxazolidinone compound of Formula I. wherein Q is X and Y may be same or different, represent, CH, CF, N;

  • X′ and

    Y′

    may be same or different, represent, CH, CF, N, C—

    OCH3, C—

    CH2—

    Ra;

    wherein Ra is hydrogen, amino, halogen, hydroxyl, azido, carboxamido, NHCH2CONH2, N(CH2CONH2)2;

    R2 and R2′

     may be same or different, represent, hydrogen, methyl, hydroxyl, C1-C6 alkoxy or halogen;

    R4 is selected from the group comprisinga) O—

    R1,b) NRbRc;

    wherein Rb is selected from hydrogen, C1-C6 alkylcarbonyl;

    Rc is selected from hydrogen, C(O)OCH2OC(O)Rd or CH(CH3)OC(O)Re;

    wherein Rd is hydrogen, C1-C6 alkyl, substituted C1-C6 alkyl with substitutents selected from amino or C1-C6 alkylamidoRe is selected from hydrogen, C1-C6 alkyl, substituted C1-C6 alkyl;

    c) formamide;

    d) carbamate;

    e) thiocarbamate;

    f) urea;

    g) C1-C6 alkylamido;

    h) C1-C6 haloalkylamido;

    i) C1-C6 thioalkylamido;

    j) substituted C1-C6 thioalkylamido, wherein the alkyl group is substituted with halo;

    k) unsubstituted or substituted heteroaryl, wherein substituents of the heteroaryl to are selected from the group comprising C1-C6 alkyl, nitro, cyano, hydroxyl, halo, amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, carboxy;

    wherein R1 is selected from the group comprising hydrogen, C1-C6 alkylsulfonyl, C1-C6-alkylcarbonyl, —

    P(O)(OM)2, wherein M is hydrogen, methyl, ethyl, t-butyl, phenyl or an alkali metal ion such as Li, Na, K;

    or R1 is an amino acid residue derived from one of the 20 naturally occurring amino acids viz. alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glutamic acid, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine and valine, attached to the oxygen via carbonyl of the amino acid to form a ester linkage;

    When Q is wherein n is 0, 1 or 2;

    W represents 3-7 membered heterocyclyl bearing one or more heteroatom selected from N;

    O, S, optionally substituted with one or more substitutents selected from the group comprising C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, carboxamide, cyano, hydroxyl, amino, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl or heteroaryl bearing one or more heteroatom selected from N, O S, optionally substituted with one or more substitutents selected from the group comprisingi. substituted or unsubstituted C1-C6 alkyl with substituents selected from the group hydroxyl, halo, nitro, cyano, aryl or heteroaryl;

    ii. substituted or unsubstituted C2-C6 alkenyl with substituents selected from the group hydroxyl, halo, nitro, cyano, aryl or heteroaryl;

    iii. C1-C6 alkylcarbonyl;

    iv. C1-C6 alkoxycarbonyl;

    v. C1-C6 alkoxycarbonylalkyl;

    vi. C1-C6 alkylcarbonylalkyl;

    vii. C1-C6 haloalkyl;

    viii formyl;

    ix. carboxy;

    x. carboxamide;

    xi. cyano;

    xii. amino;

    xiii nitro;

    xiv. hydroxyl;

    xv halo;

    xvi. morpholinocarbonylalkyl;

    xvii. hydroxyiminoalkyl;

    xviii. alkylcarbonylaminoalkyl;

    xix. alkoxyiminoalkyl;

    xx. aralkyloxyiminoalkyl;

    xxi. hydroiminoaminoalkyl;

    xxii. aryl, substituted aryl, with substituents selected from C1-C6 alkyl, nitro, cyano, hydroxyl, halo, amino, heterocyclyl;

    xxiii. substituted or unsubstituted heteroaryl, with substituents selected from C1-C6 alkyl, nitro, cyano, hydroxyl, halo, amino, heterocyclyl;

    xxiv. substituted or unsubstituted heterocyclyl, with substituents selected from C1-C6 alkyl, C1-C6 alkylcarbonyl, aralkyl, nitro, cyano, hydroxyl, halo, amino;

    xxv. C1-C6 alkylthio;

    xxvi. C1-C6 alkylsulfanylalkyl;

    xxvii. C1-C6 aralkylsulfanyl;

    xxviii. C1-C6 alkylsulfonylmethyl;

    xxix. C1-C6 alkylsulfonyloxy;

    xxxi. —

    (C1-C6 alkyl)-NRf—

    (C1-C6 alkyl)-NRbRc;

    wherein Rf is hydrogen, C1-C6 alkyl, substituted C1-C6 alkyl with substitutents selected from amino or C1-C6 alkylamido;

    or W is heteroaryloxy group optionally substituted with one or more substitutents such as C1-C6 alkyl, C2-C6 alkenyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, formyl, carboxy, carboxamide, cyano, amino, hydroxyiminoalkyl, alkoxyiminoalkyl, aralkyloxyiminoalkyl, hydroxyiminoaminoalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclyl, substituted heterocyclyl;

    OR when Q is X′ and

    Y′

    are as defined above;

    T is hydrogen or wherein R2 and R2′

     are as defined above;

    “

    a”

    is optional double bond;

    R3 and R3′

     may be same or different, represent, hydrogen, methyl, hydroxyl, C1-C6 alkoxy or halogen;

    with the proviso that when T is hydrogen, R4 is not acetamido;

    Z represents group selected from CH, NH, O, S, CH2, C(R6)R6′

    , C═

    O, NR7, C═

    C(R8)R8′

    , SO, SO2, S—

    NH, S═

    NC(O)CH3, S═

    NC(O)NHCH3, S(O)═

    NH, S(O)═

    NCH3, S(O)NC(O)CH3, S(O)═

    NC(O)NHCH3, S(O)═

    NC(O)NHCH2CH2Cl, with proviso that when X is CH, Y is CF, one of X′

    or Y′

    or both X′

    , Y′

    are N, then Z is not NH. wherein R6 and R6′

    may be same or different, represent, hydrogen, hydroxyl, amino, azido, C1-C6 alkoxy, C1-C6 alkylcarbonyloxy, C1-C6 alkylsulfonyloxy, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, C1-C6 alkyl optionally substituted with one or more substituent selected from the group comprising azido, cyano, carboxamido, hydroxyl, C1-C6 alkyloxy, C1-C6 alkylcarbonyloxy, C1-C6 alkylcarbonyl or C2-C6 alkenyl optionally substituted with one or more azido, cyano, carboxamido or hydroxyl;

    or R6 and R6′

    are combined together to provide 3-7 member heterocyclyl bearing one or more heteroatom selected from N, O, S optionally substituted with substituent selected from group comprising C1-C6 alkyl, C2-C6 alkenyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, formyl, carboxy, carboxamide, cyano, amino, hydroxyiminoalkyl, alkoxyiminoalkyl, aralkyloxyiminoalkyl, hydroxyiminoaminoalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclyl, substituted heterocyclyl;

    R7 represents hydrogen, cyano, aralkyl, CO—

    OCH2Ph, C1-C6-alkylcarbonyl, C1-C6 alkyl optionally substituted with one or more azido, cyano, heteroaryl, substituted heteroaryl, carboxamido or hydroxyl;

    R8, R8′

     may be same or different, represent, hydrogen, C1-C6 alkyl, C2-C6 alkenyl, cyano, amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, cyano, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclyl, substituted heterocyclyl;

    and isomers, polymorphs, N-oxides thereof or pharmaceutical acceptable salts thereof.

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