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Compounds with activity on muscarinic receptors

  • US 6,528,529 B1
  • Filed: 07/16/1999
  • Issued: 03/04/2003
  • Est. Priority Date: 03/31/1998
  • Status: Expired due to Fees
First Claim
Patent Images

1. A compound of formula (I):

  • embedded imagewhereinR1 is straight or branched-chain C2-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 alkylidene, C1-8 alkoxy, C1-8 heteroalkyl, C1-8 aminoalkyl, C1-8 haloalkyl, C1-8 alkoxycarbonyl, C1-8 hydroxyalkoxy, C1-8 hydroxyalkyl, —

    SH, C1-8 thioalkyl, or —

    O—

    CH2

    C5-6 aryl;

    A is C5-7 cycloalkyl, phenyl, naphthyl or C5-12 heteroaryl, wherein said heteroaryl contains one heteroatom selected from O, N or S;

    when A is C5-7 cycloalkyl, naphthyl or C5-12 heteroaryl as defined above, R2 is H, amino, hydroxyl, halo, or straight or branched-chain C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C1-6 heteroalkyl, C1-6 aminoalkyl, C1-6 haloalkyl, C1-6 alkoxycarbonyl, —

    CN, —

    CF3, —

    OR3, —

    COR3, NO2, —

    NHR3, —

    NHC(O)R3, —

    C(O)NR3R4, —

    NR3R4, —

    NR3C(O)NR4R5, —

    OC(O)R3, or —

    (CH2)qNR3R4;

    where R3, R4 and R5 are the same or different, each independently being selected from H, C1-6 alkyl;

    C5-6 aryl optionally comprising 1 or more heteroatoms selected from N, O and S, and optionally substituted with halo or C1-6 alkyl;

    C3-6 cycloalkyl;

    or R3 and R4 together with the N atom, when present, form a cyclic ring structure comprising 5-6 atoms selected from C, N, S and O; and

    q is an integer from 1 to 6;

    or when A is phenyl, R2 is amino, hydroxyl, chloro, bromo, or straight or branched-chain C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C1-6 heteroalkyl, C1-6 aminoalkyl, C1-6 haloalkyl, C1-6 alkoxycarbonyl, —

    CN, —

    CF3, —

    OR3, —

    COR3, NO2, —

    NHR3, —

    NHC(O)R3, —

    C(O)NR3R4, —

    NR3R4, —

    NR3C(O)NR4R5, —

    OC(O)R3, or —

    (CH2)qNR3R4;

    where R3, R4 and R5 are the same or different, each independently being selected from H, C1-6 alkyl;

    C5-6 aryl optionally comprising 1 or more heteroatoms selected from N, O and S, and optionally substituted with halo or C1-6 alkyl;

    C3-6 cycloalkyl;

    or R3 and R4 together with the N atom, when present, form a cyclic ring structure comprising 5-6 atoms selected from C, N, S and O; and

    q is an integer from 1 to 6;

    n is 1, 2, 3 or 4, the groups R2, when n>

    1, being the same or different;

    p is 0 or an integer from 1 to 5;

    Y is —

    NHC(O)—

    or —

    C(O)—

    ; and

    Z is a bond or CR8R9 wherein R8 and R9 are independently selected from H, and straight or branched chain C1-8 alkyl;

    provided where —

    (CH2)p

    Y—

    is —

    (CH2)3

    C(O)—

    , that —

    A—

    (R2)n and R1 are not together;

    o-methyl-phenyl and n-butyl, respectively;

    or a pharmaceutically acceptable salt, ester or prodrug thereof.

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