US 11,840,549 B2
Bisphosphonate quinolone conjugates and uses thereof
Frank H. Ebetino, Pasadena, CA (US); Shuting Sun, Pasadena, CA (US); Mark W. Lundy, Pasadena, CA (US); Charles E. McKenna, Pasadena, CA (US); Eric Richard, Pasadena, CA (US); Parish Sedghizadeh, Los Angeles, CA (US); Keivan Sadrerafi, Pasadena, CA (US); and Philip T. Cherian, Pasadena, CA (US)
Assigned to BIOVINC, LLC, Pasadena, CA (US); and UNIVERSITY OF SOUTHERN CALIFORNIA, Los Angeles, CA (US)
Filed by BIOVINC, LLC, Pasadena, CA (US); and UNIVERSITY OF SOUTHERN CALIFORNIA, Los Angeles, CA (US)
Filed on Dec. 11, 2020, as Appl. No. 17/118,795.
Application 17/118,795 is a continuation of application No. 16/207,465, filed on Dec. 3, 2018, granted, now 10,865,220.
Application 16/207,465 is a continuation in part of application No. PCT/US2017/035764, filed on Jun. 2, 2017.
Claims priority of provisional application 62/695,583, filed on Jul. 9, 2018.
Claims priority of provisional application 62/448,060, filed on Jan. 19, 2017.
Claims priority of provisional application 62/357,727, filed on Jul. 1, 2016.
Claims priority of provisional application 62/345,370, filed on Jun. 3, 2016.
Prior Publication US 2021/0101920 A1, Apr. 8, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07F 9/6558 (2006.01); C07F 9/6561 (2006.01); A61P 31/04 (2006.01); A61P 19/10 (2006.01); A61K 47/55 (2017.01); A61K 47/54 (2017.01)
CPC C07F 9/65583 (2013.01) [A61K 47/548 (2017.08); A61K 47/55 (2017.08); A61K 47/552 (2017.08); A61P 19/10 (2018.01); A61P 31/04 (2018.01); C07F 9/6561 (2013.01)] 27 Claims
 
1. A compound comprising:
a bisphosphonate; and
a quinolone moiety;
wherein the quinolone moiety is coupled to the bisphosphonate via a carbamate, an S-thiocarbamate or an O-thiocarbamate, and
wherein an oxygen or a sulfur of the carbamate, the S-thiocarbamate or the O-thiocarbamate is directly coupled to an aryl group and where the aryl group is directly or indirectly coupled to or a part of the bisphosphonate, such that the coupling of the oxygen or the sulfur to the aryl group creates an aryl carbamate, an S-thioarylcarbamate or an O-thioarylcarbamate linkage of the quinolone moiety to the bisphosphonate, and
wherein the quinolone moiety is coupled to the bisphosphonate via a nitrogen of the aryl carbamate, S-thioarylcarbamate or O-thioarylcarbamate linkage in which the nitrogen is directly or indirectly coupled to, or a component of, a substituent coupled to position 7 on the bicyclic ring structure of the quinolone moiety, wherein position 1 on the bicyclic ring structure of the quinolone moiety is the location of the nitrogen (N) on the carbonyl bearing ring of the bicyclic ring structure of the quinolone moiety, and position 3 on the bicyclic ring structure of the quinolone moiety is the location of the carboxylate on the bicyclic ring structure of the quinolone moiety.