US 9,809,558 B2
Compounds for affinity chromatography and for extending the half-life of a therapeutic agent
Peter Kumpalume, Stevenage (GB); Oliver Schon, Stevenage (GB); Christine Patricia Donahue, Waltham, MA (US); Ghotas Evindar, Waltham, MA (US); David I. Israel, Waltham, MA (US); David Paolella, King of Prussia, PA (US); Letian Kuai, Waltham, MA (US); and Ninad V. Prabhu, Waltham, MA (US)
Assigned to GlaxoSmithKline Intellectual Property Development Limited, Brentford, Middlesex (GB)
Appl. No. 15/26,725
Filed by GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED, Middlesex (GB)
PCT Filed Oct. 1, 2014, PCT No. PCT/IB2014/064998
§ 371(c)(1), (2) Date Apr. 1, 2016,
PCT Pub. No. WO2015/049651, PCT Pub. Date Apr. 9, 2015.
Claims priority of provisional application 61/885,146, filed on Oct. 1, 2013.
Claims priority of provisional application 62/025,994, filed on Jul. 17, 2014.
Prior Publication US 2016/0221962 A1, Aug. 4, 2016
Int. Cl. C07D 235/18 (2006.01); A61K 31/4184 (2006.01); C07D 401/06 (2006.01); C07D 401/10 (2006.01); C07D 235/24 (2006.01); C07D 417/14 (2006.01); A61K 31/454 (2006.01); A61K 31/4545 (2006.01); C07D 411/14 (2006.01)
CPC C07D 235/18 (2013.01) [A61K 31/4184 (2013.01); A61K 31/454 (2013.01); A61K 31/4545 (2013.01); C07D 235/24 (2013.01); C07D 401/06 (2013.01); C07D 401/10 (2013.01); C07D 411/14 (2013.01); C07D 417/14 (2013.01)] 32 Claims
 
1. A compound according to formula Ia as shown below,

OG Complex Work Unit Drawing
or a salt thereof, wherein:
R1 is H, —Cl, —F, —Br, —I, —OH, —CN, —NO2, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted cycloalkyl, aryl or heteroaryl;
R3 is —[(CH2)2E]n(CH2)2NR′R″ wherein n is any integer from 0 through 30, R′ and R″ are each independently H, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, or substituted or unsubstituted cycloalkyl, and E is CH2, O, NH or S, or E is absent;
R4 is H, —Cl, —F, —Br, —I, —OH, —CN, —NO2, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted cycloalkyl, aryl or heteroaryl;
Y1 and Y3 are independently C, O, N, NR2 or S, wherein R2 is H, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted cycloalkyl, aryl or heteroaryl;
y2 is C or N;
A and D are independently

OG Complex Work Unit Drawing
amidine, thioamide, or A and/or D is absent;
B is substituted or unsubstituted C4-C9-cycloalkyl, substituted or unsubstituted C4-C9-heterocycloalkyl comprising N, substituted or unsubstituted heteroaryl comprising N, S or O, or B is absent; and
Z is substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl comprising N, O or S, or Z is absent.