US 11,858,917 B2
Bifunctional molecules with antibody-recruiting and entry inhibitory activity against the human immunodeficiency virus
David Spiegel, New Haven, CT (US); and Christopher Parker, Medina, OH (US)
Assigned to YALE UNIVERSITY, New Haven, CT (US)
Filed by YALE UNIVERSITY, New Haven, CT (US)
Filed on Sep. 9, 2021, as Appl. No. 17/470,393.
Application 17/470,393 is a division of application No. 16/894,362, filed on Jun. 5, 2020, granted, now 11,136,316.
Application 16/894,362 is a division of application No. 16/037,678, filed on Jul. 17, 2018, granted, now 10,703,743, issued on Jul. 24, 2018.
Application 16/037,678 is a division of application No. 15/379,969, filed on Dec. 15, 2016, granted, now 10,030,008, issued on Jul. 24, 2018.
Application 15/379,969 is a division of application No. 13/988,251, granted, now 9,562,038, issued on Feb. 27, 2017, previously published as PCT/US2011/061174, filed on Nov. 17, 2011.
Claims priority of provisional application 61/414,977, filed on Nov. 18, 2010.
Claims priority of provisional application 61/522,518, filed on Aug. 11, 2011.
Prior Publication US 2022/0089579 A1, Mar. 24, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 405/14 (2006.01); A61K 31/496 (2006.01); A61K 45/06 (2006.01); A61K 9/00 (2006.01)
CPC C07D 405/14 (2013.01) [A61K 9/0014 (2013.01); A61K 31/496 (2013.01); A61K 45/06 (2013.01)] 19 Claims
 
1. A method of inhibiting entry of an HIV virus into a target cell of a patient, comprising administering to said patient an effective amount of a compound according to the chemical structure:

OG Complex Work Unit Chemistry
wherein R1 is phenyl, o-methylphenyl, m-methylphenyl, p-methylphenyl, p-ethylphenyl, p-isopropylphenyl, naphthyl, o-hydroxyphenyl, m-hydroxyphenyl, p-hydroxyphenyl, 3,5-dihydroxyphenyl, p-hydroxymethylphenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl; and
each n is independently 2, 3, 4, 5, or 6,
or a pharmaceutically acceptable salt thereof.