Carborane-based histone deacetylase (hdac) inhibitors
AssigneeThe Regents of the University of California
InventorsAlexander Spokoyny, Jessica K. Logan, Azin Saebi, Rafal Dziedzic, Pamela J. Kennedy
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Abstract
The present disclosure provides compounds and compositions capable of treating cancer, a disease of the central nervous system, and an inflammatory autoimmune disease, and methods of use thereof.
Claims36
A compound having the structure of Formula (I)
- or a pharmaceutically acceptable salt, ester, or prodrug thereof, wherein
- Y is optionally substituted boron cluster (e.g., an icosahedral boron cluster);
- R3 is H or optionally substituted alkyl;
- R4 is selected from H, halo, hydroxyl, and optionally substituted alkyl;
- R5 is selected from H, halo, hydroxyl, and optionally substituted alkyl;
- each of L1, L2, and L3 is independently selected from a bond, optionally substituted alkylene, and optionally substituted alkenylene;
- X1 is CR6 or N;
- X2 is CR7 or N;
- each R6 and R7 is independently selected from H, halo, hydroxyl, and optionally substituted alkyl;
- X3 is selected from —NH—, —N(OH)—, and O;
- and
- X4 is selected from H, optionally substituted alkyl, and optionally substituted aryl.
The compound of any one of the preceding claims, wherein R3 is alkyl or haloalkyl.
The compound of any one of the preceding claims, wherein each of R4, R5, R6, and R7 is independently selected from H, halo, hydroxyl, methyl, and —CF3.
The compound of any one of the preceding claims, wherein each of R4, R5, R6, and R7 is independently selected from H, —F, —Cl, and —Br.
The compound of any one of the preceding claims, wherein R4, R5, R6, and R7 are each H.
The compound of any one of the preceding claims, wherein L1 and L2 are each independently alkylene.
The compound of any one of the preceding claims, wherein L3 is alkenylene.
The compound of any one of the preceding claims, wherein X1 is CR6.
The compound of any one of the preceding claims, wherein X2 is CR7.
The compound of any one of the preceding claims, wherein X3 is N(OH)—.
The compound of any one of the preceding claims, wherein X4 is H.
A pharmaceutical composition comprising a compound of any one of the preceding claims and a pharmaceutically acceptable excipient.
A process for preparing a compound of Formula (I)
- comprising:
- preparing a compound of Formula (II) by reacting a compound of Formula (III) with a compound of Formula (IV) under reductive alkylation conditions:
Dependencies are inferred from the claim text.