	US 11,858,929 B2
	Compounds and methods for inhibiting fascin
Xin-Yun Huang, New York, NY (US); and Christy Young Shue, Irvine, CA (US)
Assigned to CORNELL UNIVERSITY, Ithaca, NY (US); and NOVITA PHARMACEUTICALS, INC., New York, NY (US)
Filed by NOVITA PHARMACEUTICALS, INC., New York, NY (US); and CORNELL UNIVERSITY, Ithaca, NY (US)
Filed on Feb. 16, 2021, as Appl. No. 17/176,855.
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 17/176,855 is a continuation of application No. 16/298,632, filed on Mar. 11, 2019, granted, now 10,941,141.
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 2021/0340138 A1, Nov. 4, 2021
Int. Cl. C07D 471/04 (2006.01); 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 405/14 (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 405/12 (2006.01); C07D 405/04 (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:

or tautomer thereof, and/or a pharmaceutically acceptable salt thereof; wherein

A¹is CH;

A²is N;

A³and A⁴are each independently CH, CR³or N;

A⁵and A⁶are each independently CH or CR³;

q is 1;

R¹is phenyl, 5-membered heteroaryl or 6-membered heteroaryl, wherein the phenyl, 5-membered heteroaryl or 6-membered heteroaryl is optionally substituted with 1 to 3R⁶;

L²is selected from the group consisting of —NHC(O)—, and —NHCH₂;

R²is 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 4R⁴, wherein each R⁴is 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 R³is independently selected from the group consisting of lower alkyl, lower haloalkyl, —OH, —OR′, —SH, —SR′, —NR¹⁰R¹⁰, halo, cyano, nitro, —COH, —COR⁷, —CO₂H, —CO₂R⁷, —CONR¹⁰R¹⁰, —OCOR⁷, —OCO₂R⁷, —OCONR¹⁰R¹⁰, —NR¹⁰COR¹⁰, —NR¹⁰CO₂R¹⁰, —SOR⁷, —SO₂R⁷, —SO₂NR¹⁰R¹⁰, and —NR¹⁰SO₂R⁷;

each R⁶is independently selected from the group consisting of halo, cyano, lower alkyl and lower haloalkyl;

each R⁷is independently lower alkyl or lower haloalkyl; and

each R¹⁰is independently hydrogen or lower alkyl, or two R¹⁰together with the atom(s) attached thereto form a 4- to 6-membered ring.