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Therapeutic uses of tri-aryl acid derivatives

  • US 7,005,440 B1
  • Filed: 11/28/2000
  • Issued: 02/28/2006
  • Est. Priority Date: 04/28/1999
  • Status: Expired due to Term
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Petitions
73
Forward Citations
4
Assignments
First Claim
Patent Images

1. A compound of formula I embedded imagewherein:

  • embedded imageis quinoxalinyl, quinazolinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzofuranyl, benzothiophenyl, oxazolyl, thiazolyl, oxadiazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiadiazolyl, triazolyl, pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, which is optionally substituted by one or more ring system substituents;

    embedded imageand embedded imageare, independently, aryl, which are optionally substituted by one or more ring system substituents;

    A is —

    O—

    , —

    S—

    , —

    SO—

    , —

    SO2—

    , —

    NR13—

    , —

    C(O)—

    , —

    N(R14)C(O)—

    , —

    C(O)N(R5)—

    , —

    N(R14)C(O)N(R15)—

    , —

    C(R14)═

    N—

    , a chemical bond, embedded imageB is —

    O—

    , —

    S—

    , —

    SO—

    , —

    SO2—

    , ethynylene, —

    C(O)—

    , —

    N(R18)C(O)—

    , or —

    C(O)NR18—

    ;

    D is —

    O—

    , —

    S—

    , —

    NR19—

    , a chemical bond, ethynylene, —

    N(R20)C(O)—

    , —

    C(O)—

    , or—

    C(O)N(R20)—

    ;

    E is a chemical bond or an ethylene group;

    a is 0–

    4;

    b is 0–

    4;

    c is 0–

    4;

    d is 0–

    5;

    e is 0–

    4;

    f is 0–

    6;

    g is 1–

    4;

    h is 1–

    4;

    R1, R3, R5, R7, R9, and R11, are independently hydrogen, halogen, alkyl, carboxyl, alkoxycarbonyl or aralkyl;

    R2, R4, R6, R8, R10 and R12, are independently —

    (CH2)q—

    X;

    q is 0–

    3;

    X is hydrogen, halogen, alkyl, alkenyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, aralkyl, heteroaralkyl, hydroxy, alkoxy, aralkoxy, heteroaralkoxy, carboxyl, alkoxycarbonyl, tetrazolyl, acyl, acylHNSO2—

    , —

    SR23, Y1Y2N—

    or Y3Y4NCO—

    ;

    Y1 and Y2 are independently hydrogen, alkyl, aryl, aralkyl or heteroaralkyl, or one of Y1 and Y2 is hydrogen or alkyl and the other of Y1 and Y2 is acyl or aroyl;

    Y3 and Y4 are independently hydrogen, alkyl, aryl, aralkyl or heteroaralkyl;

    Z is R21O2C—

    , R21OC—

    , cyclo-imide, —

    CN, R21O2SHNCO—

    , R21O2SHN—

    , (R21)2NCO—

    , R21O—

    2,4-thiazolidinedionyl, or tetrazolyl; and

    R21 is hydrogen, alkyl, aryl, cycloalkyl, or aralkyl;

    R13, R19 and R23 are independently R22OC—

    , R22NHOC—

    , hydrogen, alkyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, heteroaralkyl, or aralkyl;

    R14, R15, R16, R18 and R20 are independently hydrogen, alkyl, aralkyl, carbonyl, or alkoxycarbonyl;

    or R14, and R15 taken together with the carbon and nitrogen atoms through which they are linked form a 5 or 6-membered azaheterocyclyl group; and

    R22 is hydrogen, alkyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, heteroaralkyl, or aralkyl;

    ora pharmaceutically acceptable salt thereof, an N-oxide thereof, a hydrate thereof or a solvate thereof;

    wherein“

    alkyl,”

    when used to designate an alkyl group per se or when used as an alkyl component of any other group, is an aliphatic hydrocarbon group which is straight or branched having 1 to about 20 carbon atoms and is optionally substituted by one or more alkyl group substituents;

    “

    aryl”

    is an aromatic monocyclic or multicyclic ring system of about 6 to about 14 carbon atoms, which is optionally substituted by one or more ring system substituents;

    “

    heteroaryl”

    is an aromatic monocyclic or multicyclic ring system of about 5 to about 14 carbon atoms, in which at least one of the carbon atoms in the ring system is replaced by nitrogen, oxygen or sulfur, which is optionally substituted by one or more ring system substituents;

    “

    heterocyclyl”

    is a non-aromatic saturated monocyclic or multicyclic ring system of 3 to about 10 carbon atoms, in which at least one of the carbon atoms in the ring system is replaced by nitrogen, oxygen or sulfur, which is optionally substituted by one or more ring system substituents;

    “

    heteroaralkyl”

    is a heteroaryl-alkyl group, wherein the heteroaryl and alkyl groups are as defined above;

    an “

    alkyl group substituent”

    is halo, carboxy, cycloalkyl, cycloalkenyl, heterocyclyl, heterocyclenyl, aryl, alkoxy, alkoxycarbonyl, aralkoxycarbonyl, heteroaralkoxycarbonyl, or Y1Y2NCO—

    , wherein Y1 and Y2 are independently hydrogen, alkyl, aryl, aralkyl or heteroaralkyl, or Y1 and Y2 taken together with the nitrogen atom to which Y1 and Y2 are attached form heterocyclyl wherein the substituents may contain further alkyl group substituents or ring system substituents as recited herein; and

    a “

    ring system substituent”

    is alkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, aralkyl, heteroaralkyl, hydroxy, alkoxy, aryloxy, aralkoxy, acyl, aroyl, halo, nitro, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, alkylthio, arylthio, heteroarylthio, aralkylthio, heteroaralkylthio, fused cycloalkyl, fused cycloalkenyl, fused heterocyclyl, fused heterocyclenyl, arylazo, heteroarylazo, RaRbN—

    , RcRdNCO—

    , RcO2CN—

    , or RcRdNSO2—

    wherein Ra and Rb are independently hydrogen, alkyl, aryl, aralkyl or heteroaralkyl, or one of Ra and Rb is hydrogen or alkyl and the other of Ra and Rb is aroyl or heteroaroyl, and Rc and Rd are independently hydrogen, alkyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocyclyl, heterocyclenyl, aralkyl or heteroaralkyl and, where the ring is cycloalkyl, cycloalkenyl, heterocyclyl or heterocyclenyl, the ring system substituent may also include methylene, oxo and thioxo on carbon atoms thereofwherein the substituents may contain further alkyl group substituents or ring system substituents as recited herein.

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