US 12,018,002 B2
Certain chemical entities, compositions, and methods
Xiangping Qian, Foster City, CA (US); and Yong-Liang Zhu, Fremont, CA (US)
Assigned to NEUPHARMA, INC, Foster City, CA (US)
Filed by NEUPHARMA, INC, Foster City, CA (US)
Filed on Oct. 20, 2021, as Appl. No. 17/506,367.
Application 17/506,367 is a division of application No. 16/702,936, filed on Dec. 4, 2019, granted, now 11,208,388.
Application 16/702,936 is a continuation of application No. 15/676,852, filed on Aug. 14, 2017, granted, now 10,544,106, issued on Jan. 28, 2020.
Claims priority of provisional application 62/375,382, filed on Aug. 15, 2016.
Prior Publication US 2023/0043970 A1, Feb. 9, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 239/74 (2006.01); A61K 45/06 (2006.01); C07D 239/84 (2006.01); C07D 401/04 (2006.01); C07D 401/12 (2006.01); C07D 401/14 (2006.01); C07D 403/04 (2006.01); C07D 403/12 (2006.01); C07D 403/14 (2006.01); C07D 471/04 (2006.01); C07D 473/32 (2006.01); C07D 487/04 (2006.01)
CPC C07D 239/74 (2013.01) [A61K 45/06 (2013.01); C07D 239/84 (2013.01); C07D 401/04 (2013.01); C07D 401/12 (2013.01); C07D 401/14 (2013.01); C07D 403/04 (2013.01); C07D 403/12 (2013.01); C07D 403/14 (2013.01); C07D 471/04 (2013.01); C07D 473/32 (2013.01); C07D 487/04 (2013.01)] 15 Claims
 
1. A compound of Formula (II):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:

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is selected from the group consisting of phenyl, piperidine, and pyrrolidine, each of which is substituted with E;

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is selected from the group consisting of

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wherein custom characterb is a point of attachment for

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and custom characterd is a point of attachment for

OG Complex Work Unit Chemistry

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is selected from the group consisting of phenyl and pyridine;
X3 is C—R3;
X4 is C—R4;
X5 is C—R5;
R1, R3, R4, R5, and R6 are each independently selected from the group consisting of hydrogen, cyano, halo, hydroxy, azido, nitro, carboxy, oxo, sulfinyl, sulfanyl, sulfonyl, optionally substituted alkoxy, optionally substituted cycloalkyloxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted heterocycloalkyloxy, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocycloalkyl, optionally substituted amino, optionally substituted acyl, optionally substituted alkoxycarbonyl, optionally substituted aminocarbonyl, optionally substituted aminosulfonyl, and optionally substituted carbamimidoyl;
Q and Z are each independently selected at each occurrence from hydrogen, cyano, halo, hydroxy, azido, nitro, carboxy, oxo, sulfinyl, sulfanyl, sulfonyl, optionally substituted alkoxy, optionally substituted cycloalkyloxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted heterocycloalkyloxy, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocycloalkyl, optionally substituted amino, optionally substituted acyl, optionally substituted alkoxycarbonyl, optionally substituted aminocarbonyl, optionally substituted aminosulfonyl, optionally substituted carbamimidoyl, and E;
E is selected from the group consisting of

OG Complex Work Unit Chemistry
m is 0, 1, 2, 3, or 4; and
n is 0, 1, 2, 3, 4, or 5.