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Diagnostic probes and remedies for diseases with accumulation of prion protein, and stains for prion protein

  • US 20050260126A1
  • Filed: 08/29/2003
  • Published: 11/24/2005
  • Est. Priority Date: 08/30/2002
  • Status: Abandoned Application
First Claim
Patent Images

1. A compound, which is used as a probe for diagnosing diseases in which prion protein is accumulated, represented by the formula (I) or (II):

  • embedded image wherein D is NR′

    , S, O, CH═

    CH, or CH2, R′

    is H, alkyl having 1 to 4 carbons hereinafter, referred to as C1-4 alkyl), or phenyl, wherein the C1-4 alkyl is optionally substituted with halogen(s), E is N or CH, Ra is, each independently, selected from the group consisting of H, C1-4 alkyl, halogen, OH, C1-4 alkyl-OH, C1-4 alkyl-O—

    C1-4 alkyl, NH2, NH(C1-4 alkyl), N(C1-4 alkyl)2, NO2, O—

    C1-4 alkyl, COOH, and SO3H, wherein the C1-4 alkyl is optionally substituted with halogen(s), Q is N or CRb, Rb is selected from the group consisting of H, C1-4 alkyl, halogen, OH, C1-4 alkyl-OH, C1-4 alkyl-O—

    C1-4 alkyl, NH(C1-4 alkyl), NH2, N(C1-4 alkyl)2, NO2, O—

    C1-4 alkyl, COOH, and SO3H, wherein the C1-4 alkyl is optionally substituted with halogen(s), m is an integer of 0 to 4, R1 and R2 are independently selected from the group consisting of H, C1-4 alkyl, halogen, OH, C1-4 alkyl-OH, C1-4 alkyl-O—

    C1-4 alkyl, NH(C1-4 alkyl), NH2, N(C1-4 alkyl)2, NO2, O—

    C1-4 alkyl, COOH, and SO3H, wherein the C1-4 alkyl is optionally substituted with halogen(s), or alternatively, R1 and R2, together, form a benzene or naphthalene ring which is optionally substituted with one to four R4, R3 is selected from the group consisting of H, C1-4 alkyl, halogen, OH, C1-4 alkyl-OH, C1-4 alkyl-O—

    C1-4 alkyl, NH2, NH(C1-4 alkyl), N(C1-4 alkyl)2, NO2, O—

    C1-4 alkyl, COOH, SO3H, wherein the C1-4 alkyl is optionally substituted with halogen(s), and any one of the moieties represented by (a) to (e);

    embedded imagewherein each Rx is independently selected from the group consisting of H, C1-4 alkyl, halogen, OH, C1-4 alkyl-OH, C1-4 alkyl-O—

    C1-4 alkyl, NH2, NH(C1-4 alkyl), N(C1-4 alkyl)2, N═

    CH-allyl, NO2, O—

    C1-4 alkyl, COOH, and SO3H, wherein the C1-4 alkyl is optionally substituted with halogen(s), each R4 is independently selected from the group consisting of H, C1-4 alkyl, halogen, OH, C1-4 alkyl-OH, C1-4 alkyl-O—

    C1-4 alkyl, NH2, NH(C1-4 alkyl), N(C1-4 alkyl)2, NO2, O—

    C1-4 alkyl, COOH, SO3H, wherein the C1-4 alkyl is optionally substituted with halogen(s), and any one of the moieties represented by (f) to (l);

    embedded imagewherein two R4s attached on adjacent carbons may form a methylenedioxy group, and wherein the C1-4 alkyl is optionally substituted with halogen(s), each Ry is independently selected from the group consisting of H, C1-4 alkyl, halogen, OH, C1-4 alkyl-OH, C1-4 alkyl-O—

    C1-4 alkyl, NH2, NH(C1-4 alkyl), N(C1-4 alkyl)2, NO2, O—

    C1-4 alkyl, COOH, and SO3H, wherein the C1-4 alkyl is optionally substituted with halogen(s), A is any one of the rings represented by (i) to (ix);

    embedded imagewherein each Rz is independently selected from the group consisting of H, C1-4 alkyl, halogen, OH, C1-4 alkyl-OH, C1-4 alkyl —

    O—

    C1-4 alkyl, NH2, NH(C1-4 alkyl), N(C1-4 alkyl)2, NO2, O—

    C1-4 alkyl, phenyl, COOH, and SO3H, wherein the C1-4 alkyl is optionally substituted with halogen(s), X is N or CH, Y is N or CH, Z is O, S, CH2, N—

    CpH2p+1, and p is an integer of 0 to 4, or a salt or solvate thereof.

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