US 12,168,658 B2
Compounds and methods for inhibiting fascin
Xin-Yun Huang, New York, NY (US); and Christy Young Shue, Irvine, CA (US)
Assigned to NOVITA PHARMACEUTICALS, INC., New York, NY (US); and CORNELL UNIVERSITY, Ithaca, NY (US)
Filed by NOVITA PHARMACEUTICALS, INC., New York, NY (US); and CORNELL UNIVERSITY, Ithaca, NY (US)
Filed on Dec. 21, 2023, as Appl. No. 18/393,515.
Application 15/437,229 is a division of application No. 14/626,791, filed on Feb. 19, 2015, granted, now 9,573,946, issued on Feb. 21, 2017.
Application 18/393,515 is a continuation of application No. 17/176,855, filed on Feb. 16, 2021, granted, now 11,858,929.
Application 17/176,855 is a continuation of application No. 16/298,632, filed on Mar. 11, 2019, granted, now 10,941,141, issued on Mar. 9, 2021.
Application 16/298,632 is a continuation of application No. 15/851,141, filed on Dec. 21, 2017, granted, now 10,227,345, issued on Mar. 12, 2019.
Application 15/851,141 is a continuation of application No. 15/437,229, filed on Feb. 20, 2017, granted, now 9,850,243, issued on Dec. 26, 2017.
Claims priority of provisional application 61/942,554, filed on Feb. 20, 2014.
Prior Publication US 2024/0124449 A1, Apr. 18, 2024
Int. Cl. C07D 209/30 (2006.01); C07D 209/40 (2006.01); C07D 231/56 (2006.01); C07D 401/06 (2006.01); C07D 401/12 (2006.01); C07D 401/14 (2006.01); C07D 403/12 (2006.01); C07D 405/04 (2006.01); C07D 405/12 (2006.01); C07D 405/14 (2006.01); C07D 409/12 (2006.01); C07D 413/12 (2006.01); C07D 413/14 (2006.01); C07D 417/12 (2006.01); C07D 417/14 (2006.01); C07D 471/04 (2006.01)
CPC C07D 471/04 (2013.01) [C07D 209/30 (2013.01); C07D 209/40 (2013.01); C07D 231/56 (2013.01); C07D 401/06 (2013.01); C07D 401/12 (2013.01); C07D 401/14 (2013.01); C07D 403/12 (2013.01); C07D 405/04 (2013.01); C07D 405/12 (2013.01); C07D 405/14 (2013.01); C07D 409/12 (2013.01); C07D 413/12 (2013.01); C07D 413/14 (2013.01); C07D 417/12 (2013.01); C07D 417/14 (2013.01)] 20 Claims
 
1. A compound of Formula I:

OG Complex Work Unit Chemistry
or tautomer thereof, and/or a pharmaceutically acceptable salt thereof; wherein
A1 is CH;
A2 is N;
A3 and A4 are each independently CH, CR3 or N;
A5 and A6 are each independently CH or CR3;
q is 1;
R1 is phenyl substituted with 1 to 3 R6, 5-membered heteroaryl optionally substituted with 1 to 3 R6, or 6-membered heteroaryl optionally substituted with 1 to 3 R6;
L2 is selected from the group consisting of —C(O)CH2— and —CH2C (O)—;
R2 is 6- to 10-membered aryl or 5- to 10-membered heteroaryl; wherein the 6- to 10-membered aryl or 5- to 10-membered heteroaryl is optionally substituted with 1 to 4 R4, wherein each R4 is independently selected from the group consisting of lower alkyl, lower haloalkyl, phenyl (optionally substituted with lower alkyl, halo or lower haloalkyl, or —OH), —OH, —OR7, —SH, —SR7, —NR10R10, halo, cyano, nitro, —COH, —COR7, —CO2H, —CO2R7, —CONR10R10, —OCOR7, —OCO2R7, —OCONR10R10, —NR10COR7, —NR10CO2R7, —SOR7, —SO2R7, —SO2NR10R10, and —NR10SO2R7;
each R3 is independently selected from the group consisting of lower alkyl, lower haloalkyl, —OH, —OR7, —SH, —SR7, —NR10R10, halo, cyano, nitro, —COH, —COR7, —CO2H, —CO2R7, —CONR10R10, —OCOR7, —OCO2R7, —OCONR10R10, —NR10COR10, —NR10CO2R10, —SOR7, —SO2R7, —SO2NR10R10, and —NR10SO2R7;
each R6 is independently selected from the group consisting of halo, cyano, lower alkyl and lower haloalkyl;
each R7 is independently lower alkyl or lower haloalkyl; and
each R10 is independently hydrogen or lower alkyl, or two R10 together with the atom(s) attached thereto form a 4- to 6-membered ring.