US 9,809,591 B2
Heterocyclic modulators of lipid synthesis
Johan D. Oslob, Sunnyvale, CA (US); Robert S. McDowell, San Francisco, CA (US); Russell Johnson, San Mateo, CA (US); Hanbiao Yang, Sunnyvale, CA (US); Marc Evanchik, San Jose, CA (US); Cristiana A. Zaharia, Redwood City, CA (US); Haiying Cai, Cupertino, CA (US); and Lily W. Hu, Palo Alto, CA (US)
Assigned to 3-V Biosciences, Inc., Menlo Park, CA (US)
Filed by 3-V Biosciences, Inc., Menlo Park, CA (US)
Filed on Oct. 5, 2015, as Appl. No. 14/874,961.
Application 14/874,961 is a division of application No. 14/315,133, filed on Jun. 25, 2014, abandoned.
Application 14/315,133 is a continuation of application No. 13/415,660, filed on Mar. 8, 2012, granted, now 8,871,790, issued on Oct. 28, 2014.
Claims priority of provisional application 61/585,642, filed on Jan. 11, 2012.
Claims priority of provisional application 61/508,611, filed on Jul. 16, 2011.
Claims priority of provisional application 61/450,561, filed on Mar. 8, 2011.
Prior Publication US 2016/0102091 A1, Apr. 14, 2016
Int. Cl. C07D 401/10 (2006.01); C07D 471/04 (2006.01); C07D 491/052 (2006.01); C07D 405/14 (2006.01); C07D 401/12 (2006.01); C07D 401/14 (2006.01); C07D 405/12 (2006.01); C07D 491/107 (2006.01); C07D 513/04 (2006.01)
CPC C07D 471/04 (2013.01) [C07D 401/10 (2013.01); C07D 401/12 (2013.01); C07D 401/14 (2013.01); C07D 405/12 (2013.01); C07D 405/14 (2013.01); C07D 491/052 (2013.01); C07D 491/107 (2013.01); C07D 513/04 (2013.01)] 10 Claims
OG exemplary drawing
 
1. A compound of Formula (IX):

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt thereof, wherein:
R1 is H, —CN, halogen, C1-C4 straight or branched alkyl, —O—(C3-C5 cycloalkyl), —O—(C1-C4 straight or branched alkyl) wherein:
C3-C5 cycloalkyl optionally includes an oxygen or nitrogen heteroatom; and
when R1 is not H, —CN or halogen, it is optionally substituted with one or more halogens;
each R2 is independently hydrogen, halogen or C1-C4 straight or branched alkyl;
R3 is H, —OH, or halogen;
R21 is H, halogen, C1-C4 straight or branched alkyl, C3-C5 cycloalkyl wherein the C3-C5 cycloalkyl optionally includes an oxygen or nitrogen heteroatom;
R22 is H, halogen, or C1-C2 alkyl;
R24 is H, C1-C4 straight or branched alkyl, —(C1-C4 alkyl)t-OH,
—(C1-C4 alkyl)t-Ot—(C3-C5 cycloalkyl), or
—(C1-C4 alkyl)t-O—(C1-C4 straight or branched alkyl) wherein:
t is 0 or 1;
the C3-C5 cycloalkyl optionally includes an oxygen or nitrogen heteroatom;
L1 is CR23 and L2 is N, or
L1 is N and L2 is CH; and
R23 is H or C1-C4 straight or branched alkyl.