US 12,421,273 B2
Ectonucleotidase inhibitors and methods of use thereof
Lijing Chen, Cupertino, CA (US); Roland Joseph Billedeau, Santa Clara, CA (US); and Jim Li, San Francisco, CA (US)
Assigned to ANTENGENE THERAPEUTICS LIMITED, Hong Kong (CN)
Filed by ANTENGENT THERAPEUTICS LIMITED, Hong Kong (CN)
Filed on Nov. 1, 2023, as Appl. No. 18/499,248.
Application 18/499,248 is a division of application No. 17/359,990, filed on Jun. 28, 2021, granted, now 11,858,957.
Application 17/359,990 is a division of application No. 16/447,159, filed on Jun. 20, 2019, granted, now 11,078,228, issued on Aug. 3, 2021.
Claims priority of provisional application 62/827,505, filed on Apr. 1, 2019.
Claims priority of provisional application 62/688,225, filed on Jun. 21, 2018.
Prior Publication US 2024/0132533 A1, Apr. 25, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07H 19/167 (2006.01); C07H 19/067 (2006.01); C07H 19/23 (2006.01)
CPC C07H 19/167 (2013.01) [C07H 19/067 (2013.01); C07H 19/23 (2013.01)] 20 Claims
 
1. A compound having formula (IE):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt and/or prodrug thereof, wherein
Y is

OG Complex Work Unit Chemistry
Het is selected from the group consisting of

OG Complex Work Unit Chemistry
R1a is selected from H, halo, hydroxy, cyano, azido, amino, C1-6alkyl, hydroxyC1-6alkyl, amino-C1-6alkyl, —O—C(O)—O—C1-6alkyl, C1-6acyloxy, C1-6alkoxy, C2-6alkenyl, and C2-6alkynyl;
R2a is selected from halo, hydroxy, cyano, azido, amino, C1-6alkyl, hydroxy-C1-6alkyl, amino-C1-6alkyl, C1-6acyloxy, —O—C(O)—O—C1-6alkyl, C1-6alkoxy, C2-6alkenyl, and C2-6alkynyl;
R2b is C2-6alkynyl;
R3 is selected from H and alkyl;
R4 is selected from H, alkyl, CN, aryl, heteroaryl, —C(O)OR9, —C(O)NR11R12, —S(O)2R10, —P(O)(OR11)(OR12), and —P(O)(OR11)(NR13R14);
R5 is selected from H, cyano, alkyl, cycloalkylalkyl, heterocyclylalkyl, aralkyl, heteroaralkyl, and —C(O)OR9;
R6 is selected from —C(O)OR9, —C(O)NR16R17, and —P(O)(OR11)(OR12);
R9 is independently selected from H, alkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, aryl, aralkyl, heteroaryl, and heteroaralkyl;
R10 is independently selected from alkyl, alkenyl, alkynyl, amino, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, aryl, aralkyl, heteroaryl, and heteroaralkyl; and
each R11 and R12 is independently selected from H, alkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl; or
R11 and R12, together with the nitrogen atom to which they are attached, form a 5- to 7-membered heterocyclyl;
R13 is, independently for each occurrence, H or alkyl;
R14 is, independently for each occurrence, alkyl or aralkyl;
each R16 and R17 is independently selected from H, hydroxy, alkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl; or
R16 and R17, together with the nitrogen atom to which they are attached, form a 5- to 7-membered heterocyclyl.