US 9,809,521 B2
Cannabidinoid derivatives
Sean D. McAllister, San Francisco, CA (US); Pierre-Yves Desprez, Richmond, CA (US); and Anuradha Mahadevan, Westford, MA (US)
Assigned to SUTTER WEST BAY HOSPITALS, San Francisco, CA (US)
Filed by Sutter West Bay Hospitals, San Francisco, CA (US)
Filed on Jan. 25, 2016, as Appl. No. 15/5,952.
Application 15/005,952 is a division of application No. 13/690,920, filed on Nov. 30, 2012, granted, now 9,254,272.
Claims priority of provisional application 61/565,438, filed on Nov. 30, 2011.
Prior Publication US 2016/0376211 A1, Dec. 29, 2016
Int. Cl. C07C 39/42 (2006.01); A61K 31/05 (2006.01); A61K 45/06 (2006.01); A61K 31/352 (2006.01); C07C 39/10 (2006.01); C07C 43/21 (2006.01); A61K 31/085 (2006.01); C07D 295/096 (2006.01); A61K 31/495 (2006.01); C07D 295/30 (2006.01); C07C 69/017 (2006.01); C07C 271/44 (2006.01); C07D 213/80 (2006.01); C07F 9/09 (2006.01); C07C 309/17 (2006.01); C07F 9/12 (2006.01); A61K 31/337 (2006.01); A61K 31/4188 (2006.01); C07C 69/16 (2006.01); C07C 69/40 (2006.01); C07C 39/17 (2006.01); C07C 39/23 (2006.01); C07C 43/23 (2006.01)
CPC C07C 39/42 (2013.01) [A61K 31/05 (2013.01); A61K 31/085 (2013.01); A61K 31/337 (2013.01); A61K 31/352 (2013.01); A61K 31/4188 (2013.01); A61K 31/495 (2013.01); A61K 45/06 (2013.01); C07C 39/10 (2013.01); C07C 39/17 (2013.01); C07C 39/23 (2013.01); C07C 43/21 (2013.01); C07C 43/23 (2013.01); C07C 69/017 (2013.01); C07C 69/16 (2013.01); C07C 69/40 (2013.01); C07C 271/44 (2013.01); C07C 309/17 (2013.01); C07D 213/80 (2013.01); C07D 295/096 (2013.01); C07D 295/30 (2013.01); C07F 9/09 (2013.01); C07F 9/12 (2013.01); C07C 2601/14 (2017.05); C07C 2601/16 (2017.05)] 19 Claims
 
1. A compound having the structure of Formula III:

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt, or prodrug thereof, wherein:
X is independently either a C or N;
R2-R3 are each independently a hydroxyl or (C1-C2)alkoxy;
R6 is selected from the group consisting of a (C1-C12)alkyl, a hetero(C1-C11)alkyl, a (C1-C12)alkenyl, a -hetero(C1-C11)alkenyl, a (C1-C12)alkynyl, and a hetero(C1-C11)alkynyl;
R11-R18 are each independently selected from the group consisting of hydrogen, deuterium, FG, optionally substituted (C1-C8)alkyl, optionally substituted hetero(C1-C8)alkyl, optionally substituted (C1-C8)alkenyl, optionally substituted hetero(C1-C8)alkenyl, optionally substituted (C1-C8)alkynyl, optionally substituted hetero(C1-C8)alkynyl; and
R21-R31 are each independently selected from the group consisting of hydrogen, deuterium, FG, optionally substituted (C1-C8)alkyl, hetero(C1-C8)alkyl, optionally substituted (C1-C8)alkenyl, optionally substituted hetero(C1-C8)alkenyl, optionally substituted (C1-C8)alkynyl, optionally substituted hetero(C1-C8)alkynyl, optionally substituted (C5-C8)cycloalkyl, optionally substituted (C5-C8)cycloalkenyl, optionally substituted (C5-C8)cycloalkynyl, optionally substituted (C4-C8)heterocycle, optionally substituted aryl, and optionally substituted extended mixed ring system,
wherein if X are carbon atoms and the bonds represented by a dash lines are doubly covalent bonds, then at least one of R21-R31 are not hydrogen atoms, thereby affording a substituted aryl group.