US 11,919,894 B2
Pro drugs of PDE10 compounds
Sachin Mittal, Bridgewater, NJ (US); Jason W. Skudlarek, Audubon, PA (US); and Izzat T. Raheem, Doylestown, PA (US)
Assigned to Merck Sharp & Dohme LLC, Rahway, NJ (US)
Filed by Merck Sharp & Dohme LLC, Rahway, NJ (US)
Filed on Mar. 15, 2022, as Appl. No. 17/695,125.
Claims priority of provisional application 63/162,333, filed on Mar. 17, 2021.
Prior Publication US 2022/0306619 A1, Sep. 29, 2022
Int. Cl. C07D 417/14 (2006.01)
CPC C07D 417/14 (2013.01) 54 Claims
 
1. A compound of structural Formula I:

OG Complex Work Unit Chemistry
or pharmaceutically acceptable salt thereof, wherein:
R1 is selected from the group consisting of
1) —C(O)OCH2OC(O)R2;
2) —C(O)—C6-10 aryl, heteroaryl, —C(O)—C1-6 alkyl, —C(O)—C3-6 cycloalkyl, said aryl, heteroaryl, alkyl and cycloalkyl optionally substituted with 1 to 3 groups of Ra;
3) —S—C6-10 aryl, s-heteroaryl, —S—C1-6 alkyl, —S—C3-6 cycloalkyl said aryl, heteroaryl, alkyl and cycloalkyl optionally substituted with 1 to 3 groups of Ra; and
4) —C(O)OCH2dioxolyl, optionally substituted with 1 to 2 groups of Ra;
R2 is selected from the group consisting of C1-6 alkyl, C6-10 aryl, C6-10 heteroaryl, and C3-6 cycloalkyl; said alkyl, aryl, heteroaryl, and cycloalkyl optionally substituted with 1 to 3 groups of Ra; and
Ra is independently selected from the group consisting of C1-6 alkyl, OC1-6 alkyl, oxo, and halogen.