US 12,077,515 B2
Selective histone deacetylase inhibitors for the treatment of human disease
Scott Grindrod, Falls Church, VA (US); Mira Jung, Rockville, MD (US); and Anatoly Dritschilo, Bethesda, MD (US)
Assigned to Shuttle Pharmaceuticals, Inc., Rockville, MD (US)
Filed by Shuttle Pharmaceuticals, Inc., Rockville, MD (US)
Filed on Jun. 28, 2022, as Appl. No. 17/851,882.
Application 17/851,882 is a continuation of application No. 16/959,570, granted, now 11,407,723, previously published as PCT/US2019/012770, filed on Jan. 8, 2019.
Claims priority of provisional application 62/615,113, filed on Jan. 9, 2018.
Prior Publication US 2022/0363652 A1, Nov. 17, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 285/135 (2006.01); C07C 237/20 (2006.01); A61K 45/06 (2006.01)
CPC C07D 285/135 (2013.01) [C07C 237/20 (2013.01); A61K 45/06 (2013.01)] 20 Claims
 
1. A pharmaceutical composition comprising:
a histone deacetylase 6 (HDAC6) inhibitor in an amount effective to treat cancer by inhibiting HDAC6 protein activity in a patient having cancer; and
a physiologically compatible carrier medium,
wherein the HDAC6 inhibitor is a compound of formula I, II, III, IV, or V:

OG Complex Work Unit Chemistry
wherein R1 is H or optionally substituted alkyl or aryl;
R2 is H or optionally substituted alkyl or aryl;
Q is a moiety selected from the group consisting of —NR3—(CH2)n—, —(CH2)n—NR3—, —NR3—C(═O)—(CH2)n—, —(CH2)n—C(═O)—NR3—, —C(═O)—NR3—(CH2)n—, and —(CH2)n—NR3—C(═O)—, wherein n is 0 or 1, and R3 is H or optionally substituted alkyl or aryl;
each of R4, R5, R6, and R7 are independently selected from the group consisting of H, halo, and optionally substituted alkyl, aryl, alkoxy, and aryloxy;
Z is O, S, S(═O), or S(═O)2;
A is a moiety selected from the group consisting of

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, solvate, hydrate, cocrystal, or prodrug thereof.