US 12,291,501 B2
N,N diethyl-N'phenylpiperazine alpha 7 and alpha 9 nicotinic acetylcholine receptor agonists and antagonists
Nicole Alana Horenstein, High Springs, FL (US); Roger Lee Papke, Gainesville, FL (US); and Hina Andleeb, Boston, MA (US)
Assigned to University of Florida Research Foundation, Inc., Gainesville, FL (US)
Filed by University of Florida Research Foundation, Inc., Gainesville, FL (US)
Filed on Nov. 30, 2023, as Appl. No. 18/524,322.
Application 18/524,322 is a continuation of application No. 17/903,735, filed on Sep. 6, 2022, granted, now 11,884,629.
Claims priority of provisional application 63/241,611, filed on Sep. 8, 2021.
Prior Publication US 2024/0092738 A1, Mar. 21, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 213/56 (2006.01); C07D 263/32 (2006.01); C07D 295/116 (2006.01)
CPC C07D 213/56 (2013.01) [C07D 263/32 (2013.01); C07D 295/116 (2013.01)] 14 Claims
 
1. A method of treating a disease or disorder modulated by nicotinic acetylcholine receptor (nAChR) function in a subject, the method comprising administering a pharmaceutical composition comprising
a para-substituted 1,1-dialkyl-4-phenylpiperazin-1-ium having the formula:

OG Complex Work Unit Chemistry
wherein:
R1 is a —CO—R2 group, an oxazole, a pyrazole, or a pyrrole;
R2 is a pyrrolidine group or an —NH—R3 group;
R3 is an alkyl group, an aryl group, a saturated heterocyclic group, a substituted saturated heterocyclic group, an unsaturated heterocyclic group, a substituted unsaturated heterocyclic group, a pyridine, a substituted pyridine group, or a substituted phenyl group; and
R4 and R5 are each independently a methyl group or an ethyl group, or a salt thereof to the subject.