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    IBOGAINE ANALOGS AS THERAPEUTICS FOR NEUROLOGICAL AND PSYCHIATRIC DISORDERS
    1.
    发明公开
    IBOGAINE ANALOGS AS THERAPEUTICS FOR NEUROLOGICAL AND PSYCHIATRIC DISORDERS 审中-公开

    公开(公告)号：US20230348465A1

    公开(公告)日：2023-11-02

    申请号：US18017000

    申请日：2021-07-20

    Applicant: The Trustees of Columbia University in the City of New York

    Inventor： Dalibor Sames ,  Vaclav Havel ,  Christopher Hwu

    IPC: C07D471/22 ,  B01J31/02

    CPC classification number: C07D471/22 ,  B01J31/0267 ,  C07B2200/05

    Abstract: The present invention provides a compound having the structure:





    wherein

    X1 is H or alkyl;
    Y1 is H, -alkyl, -alkenyl, -alkynyl, alkylaryl, -cycloalkyl, -aryl, heteroaryl, -alkyl-Y3 or -alkyl-C(O)Y4, and
    Y2 is H, -alkyl, -alkenyl, -alkynyl, alkylaryl, -cycloalkyl, -aryl, heteroaryl, -alkyl-Y3 or -alkyl-C(O)Y4,

    wherein each Y3 is, independently, —OH, -O(alkyl), —NH2, -NH(alkyl) or halogen, and each Y4 is, independently, —OH, -O(alkyl), —NH2, -NH(alkyl) or -N(alkyl)2;


    Z1 is H, -alkyl, -alkenyl, -alkynyl, alkylaryl, -aryl, heteroaryl, -alkyl-Z3 or -alkyl-C(O)Z4, and
    Z2 is H, -alkyl, -alkenyl, -alkynyl, alkylaryl, -aryl, heteroaryl, -alkyl-Z3 or -alkyl-C(O)Z4,

    wherein each Z3 is, independently, —OH, -O(alkyl), —NH2, -NH(alkyl) or halogen, and each Z4 is, independently, —OH, -O(alkyl), —NH2, -NH(alkyl) or -N(alkyl)2;


    R1, R2, R3 and R4 are each, independently, —H, —F, —Cl, —Br, —I, —NO2, —CN, —CF3, —CF2H, —OCF3, -(alkyl), -(alkenyl), -(alkynyl), -(aryl), -(heteroaryl), —OH, —OAc, -O-(alkyl), -O-(alkenyl), -O-(alkynyl), -O-(aryl), -O-(heteroaryl), —SH, -S-(alkyl), -S-(alkenyl), -S-(alkynyl), -S-(aryl), -S-(heteroaryl), —NH2, -NH-(alkyl), -NH-(alkenyl), -NH-(alkynyl), -NH-(aryl), -NH-(heteroaryl), -C(O)R5, -S(O)R5, -SO2R5, -NHSO2R5, -OC(O)R5, -SC(O)R5, -NHC(O)R6 or -NHC(S)R6,

    wherein each R5 is, independently, -(alkyl), -(aryl), -(heteroaryl), —OH, -O(alkyl), —NH2, -NH(alkyl) or -N (alkyl) 2, and wherein each R6 is, independently, -(alkyl), -(aryl), -O-(alkyl), -S-(alkyl), -S-(aryl), —NH2, -NH(alkyl) or -N (alkyl) 2,


    wherein the compound is other than any of ibogaine, ibogamine, N-methyl-ibogaine, N-methyl-noribogaine, N-ethyl-noribogaine, N-methyl-ibogamine or 10-ethoxy-ibogamine,

    or a pharmaceutically acceptable salt of the compound, and methods of using the composition to treat pain, depressive disorders, mood disorders, anxiety disorders, substance use disorders, opioid use disorders, and opioid withdrawal symptoms.

    OXA- IBOGAINE INSPIRED ANALOGUES FOR TREATMENT OF NEUROLOGICAL AND PSYCHIATRIC DISORDERS
    2.
    发明公开
    OXA- IBOGAINE INSPIRED ANALOGUES FOR TREATMENT OF NEUROLOGICAL AND PSYCHIATRIC DISORDERS 审中-公开

    公开(公告)号：US20230382919A1

    公开(公告)日：2023-11-30

    申请号：US18366544

    申请日：2023-08-07

    Applicant: The Trustees of Columbia University in the City of New York

    Inventor： Dalibor Sames ,  Vaclav Havel ,  Benjamin Bechond ,  David Lankri

    IPC: C07D487/18 ,  C07D487/04 ,  C07D491/18 ,  C07D491/048 ,  C07D495/04 ,  C07D495/18

    CPC classification number: C07D487/18 ,  C07D487/04 ,  C07D491/18 ,  C07D491/048 ,  C07D495/04 ,  C07D495/18

    Abstract: The present invention provides a compound having the structure:






    wherein
    D, E and F are each independently NR1, CR2R3 or CR6R7,

    wherein one of D, E and F is NR1 and the remaining two are CR2R3 or CR6R7,
    wherein R1 is H or -(alkyl), and
    wherein R2, R3, R6 and R7 are each independently H, -(alkyl), -(alkenyl), -(alkynyl), -cycloalkyl, -alkylcycloalkyl, -aryl, heteroaryl or -alkylaryl;


    X1 is C or N;
    X2 is O, S, N, NR14 or CR15,

    wherein R14 is H, -(alkyl) or -cycloalkyl,
    wherein R15 is H, -(alkyl) or -cycloalkyl, and
    wherein X2 is other than N when X1 is N;


    α and β represent a bond that is present or absent, and wherein either α or β is present,

    wherein when α is present, then X1 is C and X2 is O, S or NR14, or
    when β is present, then X1 is N and X2 is N or CR15;


    R4, R5, R8 and R9 are each independently H, -(alkyl), -(alkenyl), -(alkynyl), -cycloalkyl, -alkylcycloalkyl, -aryl, heteroaryl, -alkylaryl, —OH, —O(alkyl), —OAc, —S(alkyl), —NH2, —NH(alkyl), —N(alkyl)2, —COOH, —CO2(alkyl), —CONH2, —CONH(alkyl), —CON(alkyl)2 or —CN,

    wherein when D is NR1 then R4 and R5 are each independently H, -(alkyl), -(alkenyl), -(alkynyl), -cycloalkyl, -alkylcycloalkyl, -aryl, heteroaryl or -alkylaryl,
    wherein when F is NR1 then R8 and R9 are each independently H, -(alkyl), -(alkenyl), -(alkynyl), -cycloalkyl, -alkylcycloalkyl, -aryl, heteroaryl or -alkylaryl or


    R1 and R4 together form a —(CH2)m—, wherein m represents an integer from 2 to 4; and
    R10, R11, R12 and R13 are each independently H, halogen, -(alkyl), -(alkenyl), -(alkynyl), -cycloalkyl, -(aryl), -(heteroaryl), —OH, —OAc, —O(alkyl), —O-(alkenyl), —O-(alkynyl), —O-(aryl), —O-(heteroaryl), —SH, —S(alkyl), —S-(alkenyl), —S-(alkynyl), —S-(aryl), —S-(heteroaryl), —NH2, —NH-(alkyl), —NH-(alkenyl), —NH-(alkynyl), —NH-(aryl), —NH-(heteroaryl), —CO2(alkyl), —CONH2, —CN, —CF3, —CF2H, —OCF3 or NO2 or
    R10 and R11 together form a —O(CH2)O— or
    R11 and R12 together form a —O(CH2)O— or
    R12 and R13 together form a —O(CH2)O—;
    wherein when X1 is C, X2 is NR14, and D is CR2R3, E is NR1, F is CR6R7, then (i) R14 and at least two of R10, R11, R12 and R13 are other than hydrogen, or (ii) one of R2, R3, R6 and R7 is other than H,
    wherein when X1 is C, X2 is O, and E is NH, NCH3, NCH2CH3, or NCH(CH3)2, and one of R10, R11, R12 and R13 is —OCH3 or —SCH3, then (i) one of R2, R3, R4, R5, R6, R7, R8 or R9 is other than H, or (ii) at least two of R10, R11, R12 and R13 are other than H,
    wherein when X1 is C, X2 is O, and F is NH, then at least one of R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 or R13 is other than H,
    wherein when X1 is C, X2 is S, and R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each H, and R11 is Br, then D and E is other than NH,
    wherein when X1 is N, X2 is CR15, D is CR2R3, E is NR1, F is CR6R7, and R1, R2, R3, R4, R5, R6, R7, R8 and R9 are H, and R15 is H, then one of R10, R11, R12 or R13 is other than H, and R10 is other than OMe, R11 is other than Br, R12 is other than Br and Cl, and R13 is other than OMe,
    wherein when X1 is N, X2 is CR15, D is CR2R3, E is NR1, F is CR6R7, R1 is alkyl, R2, R3, R4, R5, R6, R7, R8 and R9 are H, and R15 is CH3, then at least one of R10, R11, R12 or R13 is other than H and CH3, and R11 is other than a ketone and a carboxylic acid,
    wherein when R1 and R4 together form a —(CH2)3—, X1 is C, X2 is NR14, D is CR2R3, E is NR1, F is CR6R7, and R2, R3, R5, R6, R7, R8, R9, R10, R12, R13 and R14 are each H, then R11 is other than H, F or —CH3,

    or a pharmaceutically acceptable salt thereof.

    OXA-IBOGAINE ANALOGUES FOR TREATMENT OF SUBSTANCE USE DISORDERS
    5.
    发明公开
    OXA-IBOGAINE ANALOGUES FOR TREATMENT OF SUBSTANCE USE DISORDERS 审中-公开

    公开(公告)号：US20240150372A1

    公开(公告)日：2024-05-09

    申请号：US18546772

    申请日：2022-02-17

    Applicant: The Trustees of Columbia University in the City of New York ,  High Point University

    Inventor： Dalibor Sames ,  Vaclav Havel ,  Scott Hemby

    IPC: C07D491/22 ,  A61P25/36 ,  A61P29/00 ,  C07D471/22

    CPC classification number: C07D491/22 ,  A61P25/36 ,  A61P29/00 ,  C07D471/22

    Abstract: The present invention provides a method of treating a subject afflicted with a substance use disorder (SUD) comprising administering to the subject an effective amount of a compound having the structure:






    wherein
    A is a ring structure, with or without substitution;
    X1 is C or N;
    X2 is N, O, or S;
    Y1 is H, -(alkyl), -(alkenyl), -(alkynyl), -(cycloalkyl), -(haloalkyl), -(alkyl)-O-(alkyl) or -(alkyl)-(cycloalkyl);
    Y2 is H, -(alkyl), -(alkenyl), -(alkynyl), -(cycloalkyl), -(haloalkyl), -(alkyl)-O-(alkyl) or -(alkyl)-(cycloalkyl);
    Y3 is H, -(alkyl), -(alkenyl), -(alkynyl), -(cycloalkyl), -(haloalkyl), -(alkyl)-O-(alkyl) or -(alkyl)-(cycloalkyl);
    Y4 is H, -(alkyl), -(alkenyl), -(alkynyl), -(cycloalkyl), -(haloalkyl), -(alkyl)-O-(alkyl) or -(alkyl)-(cycloalkyl);
    Y5 is H, -(alkyl), -(alkenyl), -(alkynyl), -(cycloalkyl), -(haloalkyl), -(alkyl)-O-(alkyl) or -(alkyl)-(cycloalkyl);
    Y6 is H, -(alkyl), -(alkenyl), -(alkynyl), -(cycloalkyl), -(haloalkyl), -(alkyl)-O-(alkyl) or -(alkyl)-(cycloalkyl);
    α and β are each present or absent and when present each is a bond,

    wherein either α or β is present, and
    when α is present, then X1 is C and X2 is S or O, or
    when β is present, then X1 is N and X2 is N; and


    R1, R2, R3 and R4 are each independently —H, -(alkyl), -(alkenyl), -(alkynyl), -(haloalkyl), -(cycloalkyl), -(aryl), -(heteroaryl), -(heteroalkyl), -(hydroxyalkyl), -(alkyl)-(aryl), -(alkyl)- (heteroaryl), -(alkyl)-(cycloalkyl), -(alkyl)-OH, -(alkyl)-O-(alkyl), —OH, —NH2, —OAc, —CO2H, —CN, OCF3, halogen, —CO2—(C2-C12 alkyl), C(O)—NH2, —C(O)—NH-(alkyl), C(O)—NH-(aryl), —O-alkyl, —O-alkenyl, —O-alkynyl, —O-aryl, —O-(heteroaryl), —NH-alkyl, —NH-alkenyl, —NH-alkynyl, —NH-aryl, —NH-(heteroaryl), —O—C(O) (alkyl), or —C(O)—N(alkyl)2,

    or a pharmaceutically acceptable salt or ester thereof, so as to thereby treat the subject afflicted with the substance use disorder (SUD).

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