US 11,939,301 B2
5HT1F receptor agonists and mitochondrial biogenesis
Christopher C. Lindsey, Wadmalaw Island, SC (US); Craig C. Beeson, Charleston, SC (US); Yuri Karl Peterson, Charleston, SC (US); and Rick G. Schnellmann, Tucson, AZ (US)
Assigned to MUSC Foundation for Research Development, Charleston, SC (US); and The United States Government as Represented by the Department of Veterans Affairs, Washington, DC (US)
Filed by MUSC FOUNDATION FOR RESEARCH DEVELOPMENT, Charleston, SC (US); and The United States Government as Represented by the DEPARTMENT OF VETERANS AFFAIRS, Washington, DC (US)
Filed on Apr. 23, 2021, as Appl. No. 17/238,492.
Application 17/238,492 is a continuation of application No. 16/347,163, granted, now 11,014,892, previously published as PCT/US2017/059651, filed on Nov. 2, 2017.
Claims priority of provisional application 62/416,243, filed on Nov. 2, 2016.
Prior Publication US 2021/0238147 A1, Aug. 5, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 239/47 (2006.01); A61P 13/12 (2006.01); A61K 45/06 (2006.01)
CPC C07D 239/47 (2013.01) [A61P 13/12 (2018.01); A61K 45/06 (2013.01)] 12 Claims
 
1. A compound according to formula (I):

OG Complex Work Unit Chemistry
wherein:
L is a bond, —C(O)—, —C(O)CH2— or —S(O)2—;
R1 is phenyl optionally mono-, bi- or tri-substituted independently with hydrogen, alkoxy, (═O), —NH-alkoxy, —NH2, —OH, halogen, lower alkyl, —NHC(O)N(CH3)2, —NHS(O)2-phenyl or —NHC(O)-phenyl,
R2 and R3 are, independently of each other, hydrogen, lower alkyl, alkoxy, —NH-lower alkyl, heteroaryl, —S(O)2-phenyl or indolinyl, said heteroaryl and indolinyl groups optionally substituted independently with lower alkyl, C(O)-alkoxy or —C(O)R4,
or R2 and R3, together with the nitrogen atom to which they are attached, combine to form a six-membered heterocycloalkyl group optionally substituted with lower alkyl; and
R4 is a heterocycloalkyl group optionally substituted with lower alkyl,
or a pharmaceutically acceptable salt thereof,
with the proviso that said compound is not 2,4,6-trifluoro-N-(6-(1-methylpiperidine-4-carbonyl)pyridin-2-yl)benzamide.