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Benzimidazolidinone derivatives as muscarinic agents

  • US 6,951,849 B2
  • Filed: 04/03/2003
  • Issued: 10/04/2005
  • Est. Priority Date: 10/02/2001
  • Status: Expired due to Fees
First Claim
Patent Images

1. A compound of Formula I embedded imageor a pharmaceutically acceptable salt or prodrug thereof, whereinX is selected from the group consisting of C, O, N and S Z is selected from the group consisting of OH and N Y is selected from the group consisting of ═

  • O, ═

    N and ═

    S or tautomers thereof;

    SPU is a spacer unit providing a distance d between Z and N wherein —

    SPU—

    is a biradical selected from the group consisting of —

    (CR6R7)n-A-, —

    (CR6R7)p

    CH═

    CH—

    (CR6R7)q

    , and —

    (CR6R7)p

    C≡

    C(CR6R7)q

    wherein n, p, and q are each individually and independently in the range 0 to 5, such as 0, 1, 2, 3, 4, or 5 and A is absent or an optionally substituted —

    C3-8-cycloalkyl;

    N together with R1 and R2 form a heterocyclic ring wherein said heterocyclic ring is selected from the group consisting of embedded imageand wherein the heterocyclic ring is substituted with one or more substituents R4 independently selected from the group consisting of hydrogen, halogen, hydroxy, C1-8-alkyl, C1-8-heteroalkyl, C3-8-cycloalkyl, C3-8-heterocyclyl, C5-10-aryl, C5-10-heteroaryl, C1-6-arylalkyl, C1-6-heteroarylalkyl, C1-8-alkoxy, O—

    C2-8-alkenyl, O—

    C2-8-alkynyl, S—

    C1-8-alkyl, S—

    C2-8-alkenyl, and S—

    C2-8-alkynyl C1-8-alkylcarbonyl, C1-8-alkoxycarbonyl, C1-8-alkylidene, C2-8-alkenyl, C2-8-alkynyl, C1-6-alkyloxyimino, and C1-6-alkyloxyamino each of which may be optionally substituted with a substituent R5, wherein at least one R4 is not hydrogen, R5 is selected from the group consisting of hydrogen, halogen, hydroxy, C1-8-alkyl, C1-8-heteroalkyl, C1-8-alkoxy, C3-8-cycloalkyl, C3-8-heterocyclyl, C1-8-alkylcarbonyl, C1-8-alkylidene, C2-8-alkenyl and C2-8-alkynyl;

    RX may be absent or selected from the group consisting of hydrogen, optionally substituted C1-8-alkyl, optionally substituted C3-8-cycloalkyl, optionally substituted C2-8-alkenyl, optionally substituted C2-8-alkynyl, CH2

    N(R5)(R5), CH2

    OR5, CH2

    SR5, CH2

    O—

    C(═

    O)R5, CH2

    O—

    C(═

    S)R5;

    R3 may be present 0-4 times and selected from the group consisting of halogen, hydroxy, optionally substituted C1-8-alkyl, C1-8-alkoxy, optionally substituted C1-8-alkylidene, optionally substituted C2-8-alkenyl, optionally substituted, C2-8-alkynyl optionally substituted aryl, optionally substituted heteroaryl, optionally substituted C3-8-cycloalkyl, optionally substituted C3-8-heterocyclyl, and optionally substituted C1-8-alkylcarbonyl;

    each R6 and each R7 is optionally and independently selected from the group consisting of hydrogen, halogen, hydroxy, optionally substituted C1-8-alkyl, optionally substituted C1-8-alkoxy, optionally substituted C1-8-heteroalkyl, optionally substituted C1-8-alkylidene, optionally substituted C2-8-alkenyl, optionally substituted C2-8-alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted C3-8-cycloalkyl, optionally substituted C3-8-heterocyclyl, optionally substituted C1-6-arylalkyl, optionally substituted C5-10-aryl, optionally substituted C1-8-alkylcarbonyl, optionally substituted —

    C(O)NH-alkyl, optionally substituted —

    C(O)NH-aryl, optionally substituted —

    C(O)O-alkyl, optionally substituted —

    C(O)O-aryl, optionally substituted —

    OC(O)-alkyl, and optionally substituted —

    OC(O)-aryl.

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