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CYCLOPAMINE ANALOGS

  • US 20090012109A1
  • Filed: 08/27/2008
  • Published: 01/08/2009
  • Est. Priority Date: 12/28/2006
  • Status: Active Grant
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Petitions
42
Forward Citations
2
Assignments
First Claim
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1. A compound represented by the following structure:

  • or a pharmaceutically acceptable salt thereof;

    wherein;

    R1 is H, alkyl, —

    OR, amino, sulfonamido, sulfamido, —

    OC(O)R5, —

    N(R5)C(O)R5, or a sugar;

    R2 is H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, nitrile, or heterocycloalkyl;

    or R1 and R2 taken together form ═

    O, ═

    S, ═

    N(OR), ═

    N(R)—

    , ═

    N(NR2), ═

    C(R)2;

    R3 is H, alkyl, alkenyl, or alkynyl;

    R4 is H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, aralkyl, heteroaryl, heteroaralkyl, haloalkyl, —

    OR, —

    C(O)R5, —

    CO2R5, —

    SO2R5, —

    C(O)N(R5)(R5), —

    [C(R)2]q-R5, —

    [(W)—

    N(R)C(O)]qR5, —

    [(W)—

    C(O)]qR5, —

    [(W)—

    C(O)O]qR5, —

    [(W)—

    OC(O)]qR5, —

    [(W)—

    SO2]qR5, —

    [(W)—

    N(R5)SO2]qR5, —

    [(W)—

    C(O)N(R5)]qR5, —

    [(W)—

    O]qR5, —

    [(W)—

    N(R)]qR5, —

    W—

    NR3+X—

    , or —

    [(W)—

    S]qR5;

    each W is, independently, a diradical;

    each q is, independently, 1, 2, 3, 4, 5, or 6;

    X- is a halide;

    each R5 is, independently, H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, aralkyl, heteroaryl, heteroaralkyl or -[C(R)2]p-R6;

    wherein p is 0-6;

    or any two occurrences of R5 on the same substituent can be taken together to form a 4-8 membered optionally substituted ring which contains 0-3 heteroatoms selected from N, O, S, and P;

    each R6 is, independently, hydroxyl, —

    N(R)COR, —

    N(R)C(O)OR, —

    N(R)SO2(R), —

    C(O)N(R)2, —

    OC(O)N(R)(R), —

    SO2N(R)(R), —

    N(R)(R), —

    COOR, —

    C(O)N(OH)(R), —

    OS(O)2OR, —

    S(O)2OR, —

    OP(O)(OR)(OR), —

    NP(O)(OR)(OR), or —

    P(O)(OR)(OR);

    each R is independently H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl or aralkyl;

    each of R7 and R7′

    is H, or R7 and R7′

    taken together form ═

    O; and

    each of R8 and R9 are H, or R8 and R9 taken together form a bond;

    provided that when R2, R3, R4, are H, R1 is not hydroxyl or a sugar;

    provided that when R4 is hydroxyl, R1 is not a sugar or hydroxyl;

    provided that when R4 is hydroxyl, R1 and R2 together are not C═

    O;

    provided that when R3, R4, R8, R9 are H and R7 and R7′

    are taken together form ═

    O, then R1 cannot be hydroxyl and R2 cannot be H;

    provided that when R3, R4, R8, R9 are H and R7 and R7′

    are taken together form ═

    O, then R1 cannot be acetate and R2 cannot be H;

    provided that when R3, R4, R7, R7′

    , R8, and R9 are H, then R1 and R2 taken together cannot be ═

    O; and

    provided that when R3, R4, R7, R7′

    , R8, R9 are H, then R1 and R2 cannot be H.

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