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US 8,299,268 B2Granted
Methods for preparing diazonamides
AssigneesBoard of Regents, The University of Texas System, Joyant Pharmaceuticals, Inc.
InventorsGunnar Hanson, Charles Caldwell, Patrick G. Harran, Susan Harran, Qi Wei, Ming Zhou
Life of this patent
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Abstract
This invention relates to novel macrocyclic lactams intermediates useful for the preparation of diazonamide analogs. This invention also relates to a novel electrochemical oxidative cyclization for the preparation of such macrocyclic lactams, and their further elucidation to provide diazonamide analogs.
Claims14
A compound of formula (I):
- or a salt thereof;
- wherein:
- R1 is C1-C4 alkyl;
- R2 is H or Me;
- R3 is —NR4R5;
- R4 is H, or C1-C4 alkyl;
- R5 is H, or C1-C8 alkyl, C1-C8 heteroalkyl, C6-C14 arylalkyl, C6-C14 heteroarylalkyl, arylsulfonyl, trialkylsilyl, or alkoxycarbonyl, each of which may be optionally substituted;
- or —C(═X)R′ where X is O, S, or NH, and R′ is optionally fluorinated C1-C8 alkyl, C2-C8 alkenyl, C5-C12 aryl, or C6-C14 arylalkyl, each of which may be optionally substituted;
- R6 is H, or an arylalkyl, arylsulfonyl, acyl or alkoxycarbonyl;
- R7 is H, or halo, —CN, optionally substituted C1-C6 acyl, —COOR8, or —C(O)NR92;
- R8 is H, or C1-C8 alkyl, C2-C8 alkenyl, C5-C6 aryl, C6-C14 arylalkyl, or trialkylsilyl;
- R9 is H, or C1-C8 alkyl, C2-C8 alkenyl, C5-C6 aryl, C6-C14 arylalkyl, C6-C14 heteroarylalkyl, —OH, or C1-C4 alkoxy, each of which may be optionally substituted;
- or two R9 on the same N can optionally cyclize to form a ring;
- and
- Y′ is H or halo, and Y is halo or —OR10, where R10 is H, or is optionally fluorinated alkylsulfonyl or arylsulfonyl.
12 more elements
A compound of a formula selected from the group consisting of:
A compound of a formula selected from the group consisting of:
Dependencies are inferred from the claim text.