US 9,809,603 B1
Deuterium-enriched isoindolinonyl-piperidinonyl conjugates and oxoquinazolin-3(4H)-yl-piperidinonyl conjugates and methods of treating medical disorders using same
Vincent Jacques, Somerville, MA (US)
Assigned to DEUTERX, LLC, Andover, MA (US)
Filed by DeuteRx, LLC, Andover, MA (US)
Filed on Aug. 18, 2016, as Appl. No. 15/240,499.
Claims priority of provisional application 62/206,396, filed on Aug. 18, 2015.
Int. Cl. C07D 495/14 (2006.01); C07B 59/00 (2006.01)
CPC C07D 495/14 (2013.01) [C07B 59/002 (2013.01); C07B 2200/05 (2013.01)] 22 Claims
1. A deuterium-enriched compound of Formula I:

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt thereof, wherein:
Z is H or D, provided that the abundance of deuterium in Z is at least 30%;
X1 is —CH2—, —C(O)—, or ψ-C(CH3)═N—, where ψ is a bond to the amide nitrogen atom;
X2 is —N(R1)—, —O—, —(C1-C2)-alkylene-N(R1)—, or —(C1-C2)-alkylene-O—;
Y1 is a 3-30 membered alkylene or 3-30 membered heteroalkylene, each of which is optionally substituted by one or more R2;
R1 is hydrogen or —(C1-C4)-alkyl;
R2 represents independently for each occurrence oxo, —(C1-C6)-alkyl, —(C3-C6)-cycloalkyl, halogen, —(C1-C6)-haloalkyl, hydroxyl, —(C1-C6)-alkoxyl, or —(C1-C6)-hydroxyalkyl; or two occurrences of R2 are taken together with the intervening atom or atoms to form a 3-8 membered ring;
A1 is a protein binding moiety having a molecular weight of less than 2500 g/mol; and any hydrogen atom may be optionally replaced with D.