US 12,344,626 B2
Pharmaceutical compounds and therapeutic methods
Spencer David Kimball, New Brunswick, NJ (US); Darren R. Carpizo, New Brunswick, NJ (US); and John A. Gilleran, New Brunswick, NJ (US)
Assigned to RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY, New Brunswick, NJ (US)
Appl. No. 17/605,795
Filed by RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY, New Brunswick, NJ (US)
PCT Filed Apr. 22, 2020, PCT No. PCT/US2020/029379
§ 371(c)(1), (2) Date Oct. 22, 2021,
PCT Pub. No. WO2020/219587, PCT Pub. Date Oct. 29, 2020.
Claims priority of provisional application 62/837,707, filed on Apr. 23, 2019.
Prior Publication US 2022/0185827 A1, Jun. 16, 2022
Int. Cl. C07F 3/00 (2006.01); A61K 45/06 (2006.01); C07D 213/68 (2006.01); C07D 401/12 (2006.01); C07D 405/12 (2006.01)
CPC C07F 3/003 (2013.01) [A61K 45/06 (2013.01); C07D 213/68 (2013.01); C07D 401/12 (2013.01); C07D 405/12 (2013.01)] 16 Claims
 
1. A complex comprising Zn2+ and a compound of formula (I):

OG Complex Work Unit Chemistry
or a deuterated analog thereof, or an ion or poly-ion thereof, or a salt of said complex, wherein:
R1 is (C1-C6) alkoxy, (C3-C6) cycloalkyoxy, or —OR5 wherein any (C1-C6) alkoxy or (C3-C6) cycloalkyoxy is substituted with one or more groups independently selected from —N(Ra)2 and (C1-C6) alkoxy;
R2 is selected from the group consisting of H, phenyl, heteroaryl, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, and (C3-C6) cycloalkyl, wherein any phenyl, heteroaryl, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, and (C3-C6) cycloalkyl, is optionally substituted with one or more groups independently selected from halo, —N(Rb)2, (C3-C6) cycloalkyl, (C1-C6) alkoxy, (C2-C6) alkanoyloxy, (C2-C6) alkoxycarbonyl, (C2-C6) alkylaminocarbonyl, and (C2-C6) alkanoylamino;
R3 and R4 are each independently selected from H, (C1-C6) alkyl, piperidinyl, or piperazinyl, which piperidinyl or piperazinyl is optionally substituted with pyridyl; or R3 and each R4 taken together with the nitrogen to which they are attached form a 3, 4, 5, 6, 7, 8, or 9 membered ring that is optionally substituted with one or more groups independently selected from the group consisting of halo;
R5 is a 4-7 membered heterocyclyl;
Y is S, O, or Se;
each Ra is independently selected from the group consisting of H, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C3-C6) cycloalkyl, (C1-C6) alkanoyl, and (C1-C6) alkoxycarbonyl, wherein any (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C3-C6) cycloalkyl, (C1-C6) alkanoyl, and (C1-C6) alkoxycarbonyl, (C2-C6) alkoxycarbonyl, (C2-C6) alkylaminocarbonyl, and (C2-C6) alkanoylamino is optionally substituted with one or more groups independently selected from halo, (C3-C6) cycloalkyl, and (C1-C6) alkoxy; or two Ra taken together with the nitrogen to which they are attached form a azetidino, pyrrolidino, piperidino, or morpholino ring; and
each Rb is independently selected from the group consisting of H, (C1-C6) alkyl, (C3-C6) alkenyl, (C3-C6) alkynyl, (C3-C6) cycloalkyl, (C1-C6) alkanoyl, (C1-C6) alkylaminocarbonyl and (C1-C6) alkoxycarbonyl, wherein any (C1-C6) alkyl, (C3-C6) alkenyl, (C3-C6) alkynyl, (C3-C6) cycloalkyl, (C1-C6) alkanoyl, and (C1-C6) alkoxycarbonyl, (C1-C6) alkylaminocarbonyl, and (C2-C6) alkanoylamino is optionally substituted with one or more groups independently selected from halo, (C3-C6) cycloalkyl, and (C1-C6) alkoxy; or two Ra taken together with the nitrogen to which they are attached form a ring, e.g., azetidino, pyrrolidino, piperidino, or morpholino;
provided the compound of formula (I) is not:

OG Complex Work Unit Chemistry