US 11,897,857 B2
Isotopically-stabilized tetronimide compounds
Mark Jon Olsen, Phoenix, AZ (US); and Jean Paul Seerden, Groningen (NL)
Assigned to Midwestern University, Downers Grove, IL (US)
Filed by Midwestern University, Downers Grove, IL (US)
Filed on Dec. 11, 2020, as Appl. No. 17/119,602.
Application 17/119,602 is a continuation of application No. 16/791,252, filed on Feb. 14, 2020, granted, now 10,961,211.
Claims priority of provisional application 62/806,327, filed on Feb. 15, 2019.
Prior Publication US 2021/0094927 A1, Apr. 1, 2021
Int. Cl. C07D 307/66 (2006.01); A61P 35/04 (2006.01)
CPC C07D 307/66 (2013.01) [A61P 35/04 (2018.01); C07B 2200/05 (2013.01)] 8 Claims
 
1. A method of treating one or more conditions associated with a disease selected from the group consisting of hypercholesterolemia, a viral disease, and blood coagulation disorders,
by administering one or more doses of
a pharmaceutical composition comprising one or more deuterated compounds of Formulas {I-A}, {I-B}, {I-C}, {I-D}, {I-E}, {I-F}, I-G}, or {I-H}:or one or more pharmaceutically-acceptable esters, metabolites, prodrugs, or solvates thereof and a pharmaceutically-acceptable carrier
in one or more amounts effective to treat one or more conditions associated said disease;
wherein at least one deuterated compound is represented by any one of the following Formulas:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
or a salt, ester, metabolite, prodrug, or solvate thereof,
wherein Ar1 is a substituted or unsubstituted C6-C20 aryl or 5- to 20-membered heteroaryl;
wherein at least one of V1, V2, V3, V4, V5, or Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, or Z9 is a deuterium atom (D) and any atom not designated as deuterium is present as hydrogen (H, or not shown) at its natural isotopic abundance;
wherein W is C(O), C(S), or S(O)2;
wherein Y is a single bond, O, CR50R51, or NR52 when W is CO and Y is a single bond, CR50R51 or NR52 when W is SO2;
wherein R53 is selected from the group consisting of substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C7-C26 arylalkyl, substituted or unsubstituted 5 to 20-membered heteroaryl, and substituted or unsubstituted 6-26 membered heteroarylalkyl; and
wherein Ar2, designated as an unsubstituted or substituted C6-C20 heteroaryl is selected from the group consisting of: phenyl; naphthyl; pyridyl; pyridine; pyridone; pyrimidine; pyradazine; pyrazine; purine; furan; thiophene; oxazole; thiazole; isoxazole; isothiazole; oxadiazole; thiadiazole; pyrrole; imidazole; triazole; tetrazole; and diazepine.