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Pyridyl imidazoles

  • US 5,656,644 A
  • Filed: 07/20/1994
  • Issued: 08/12/1997
  • Est. Priority Date: 07/20/1994
  • Status: Expired due to Term
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1. A compound of formula (I):

  • ##STR9## wherein;

    R1 is 4-pyridyl which is optionally substituted with one or two substituents each of which is independently selected from C1-4 alkyl, halo, C1-4 alkoxy, C1-4 alkylthio, NH2, mono- or di-C1-6 -alkylamino or N-heterocyclyl ring selected from pyrrolidine, piperidine, piperazine, morpholine, imidazolidine, and pyrazolidine;

    R2 is hydrogen;

    n'"'"' is an integer having a value of 1 to 10;

    m is 0, or the integer 1 or 2;

    R3 is Q--(Y1)t ;

    Q is an phenyl;

    t is an integer of 1 to 3;

    Z is oxygen or sulfur;

    n is 0 or an integer from 1 to 10;

    Y1 is independently selected from --(CR10 R20)n Y2 ;

    Y2 is OH, --NO2, --S(O)m '"'"'R11, --S(O)m '"'"'OR8, --S(O)m NR8 R9, --NR8 R9, --O(CR10 R20)n NR8 R9, --C(O)R8, --CO2 R8, --CO2 (CR10 R20)n '"'"'CONR8 R9, --ZC(O) R8, --CN, --C(Z)NR8 R9, --NR10 C(Z) R8, --C(Z)NR8 OR9, --NR10 C(Z)NR8 R9, --NR10 S(O)m R11, --N(OR21)C(Z)NR8 R9, --N(OR21)C(Z)R8, --C(═

    NOR21)R8, --NR10 C(═

    NR15)SR11, --NR10 C(═

    NR15)NR8 R9, --NR10 C(═

    CR14 R24) SR11, --NR10 C(═

    CR14 R24)NR8 R9, --NR10 C(O)C(O)NR8 R9, --NR10 C(O)C(O)OR10, --C(═

    NR13)NR8 R9, --C(═

    NOR13)NR8 R9, --C(═

    NR13)ZR11, --OC(Z)NR8 R9, --NR10 S(O)m CF3, --NR10 C(Z)OR10, 5-(R18)-1,2,4-oxadizaol-3-yl or 4-(R12)-5-(R18 R19)-4,5-dihydro-1,2,4-oxadiazol-3-yl;

    provided that Y1 may also be a halogen or C1-5 alkyl when t=2 or 3;

    m'"'"' is an integer having a value of 1 or 2;

    R4 is phenyl, naphth-1-yl or naphth-2-yl which is optionally substituted by one or two substituents, each of which is independently selected, and which, for a 4-phenyl, 4-naphth-1-yl or 5-naphth-2-yl substituent, is halo, cyano, --C(Z)NR7 R17, --C(Z)OR23, --(CR10 R20)m '"'"'"COR36, SR5, --SOR5, --OR36, halo-substituted-C1-4 alkyl, C1-4 alkyl, --ZC(Z)R36, --NR10 C(Z)R23, or --(CR10 R20)m '"'"'"NR10 R20 and which, for other positions of substitution, is halo, cyano, --C(Z)NR16 R26, --C(Z)OR8, --(CR10 R20)m "COR8, --S(O)m R8, --OR8, halo-substituted-C1-4 alkyl, --C1-4 alkyl, --(CR10 R20)m "NR10 C(Z)R8, --NR10 S(O)m '"'"'R11, --NR10 S(O)m '"'"'NR7 R17 --ZC(Z)R8 or --(CR10 R20)m '"'"'NR16 R26 ;

    whereinm" is 0 to 5 and m'"'"'" is 0 or 1;

    R5 is hydrogen, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl or NR7 R17, excluding the moieties --SR5 being --SNR7 R17 and --SOR5 being --SOH;

    R7 and R17 is each independently selected from hydrogen or C1-4 alkyl or R7 and R17 together with the nitrogen to which they are attached form a heterocyclic ring members which ring optionally contains an additional heteroatom selected from oxygen, selected from pyrrolidine, piperidine, piperazine, morpholine, imidazolidine, and pyrazolidine;

    R8 is hydrogen or R11 ;

    R9 is hydrogen, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-7 cycloalkyl, C5-7 cycloalkenyl, aryl, arylalkyl, or R8 and R9 may together with the nitrogen to which they are attached form a heterocyclic ring selected from pyrrolidine, piperidine, piperazine, morpholine, imidazolidine, and pyrazolidine;

    R10 and R20 is each independently selected from hydrogen or C1-4 alkyl;

    R11 is C1-10 alkyl, halo-substituted C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-7 cycloalkyl, C5-7 cycloalkenyl, aryl, arylalkyl;

    R12 is hydrogen, --C(Z)R13 or optionally substituted C1-4 alkyl, optionally substituted aryl, optionally substituted arylC1-4 alkyl, or S(O)2 R25 ;

    R13 is hydrogen, C1-10 alkyl, C3-7 cycloalkyl, aryl, arylC1-10 alkyl;

    R14 and R24 is each independently selected from hydrogen, alkyl, nitro or cyano;

    R15 is hydrogen, cyano, C1-4 alkyl, C3-7 cycloalkyl or aryl;

    R16 and R26 is each independently selected from hydrogen or optionally substituted C1-4 alkyl, optionally substituted aryl or optionally substituted aryl-C1-4 alkyl, or together with the nitrogen which they are attached form a heterocyclic ring selected from pyrrolidine, piperidine, piperazine, morpholine, imidazolidine, and pyrazolidine;

    R18 and R19 is each independently selected from hydrogen, C1-4 alkyl, substituted alkyl, optionally substituted aryl, optionally substituted arylalkyl or together R18 and R19 denote a double bonded oxygen or sulfur;

    wherein the alkyl, aryl and arylalkyl groups are optionally substituted by halogen, hydroxy, hydroxy substituted C1-10 alkyl, C1-10 alkoxy, S(O)m alkyl, (wherein m is 0, 1 or

         2), NR7 R17 group, C1-10 alkyl, cycloalkyl, cycloalkyl alkyl, halosubstituted C1-10 alkyl, optionally substituted aryl, optionally substituted arylalkyl, wherein these aryl moieties may also be substituted one to two times by halogen, hydroxy, hydroxy substituted alkyl, C1-10 alkoxy, S(O)m alkyl, NR7 R17 group, C1-10 alkyl, or CF3 ;

    R21 is hydrogen, a pharmaceutically acceptable cation, C1-10 alkyl, C3-7 cycloalkyl, aryl, aryl C1-4 alkyl, aroyl, or C1-10 alkanoyl;

    R22 is R10 or C(Z)--C1-4 alkyl;

    R23 is C1-4 alkyl, halo-substituted-C1-4 alkyl, or C3-5 cycloalkyl;

    R36 is hydrogen or R23 ;

    R25 is C1-10 alkyl, C3-7 cycloalkyl;

    R27 is hydrogen, cyano, C1-4 alkyl, C3-7 cycloalkyl, or aryl;

    or a pharmaceutically acceptable salt thereof.

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