US 12,285,489 B2
Bone targeted antimicrobial oxazolidinone related compounds, formulations thereof, and uses thereof
Frank Hallock Ebetino, Venice, FL (US); Shuting Sun, Temple City, CA (US); Charles E. McKenna, Pacific Palisades, CA (US); Keivan Sadrerafi, Pasadena, CA (US); and Philip Cherian, Pasadena, CA (US)
Appl. No. 17/255,446
Filed by Frank Hallock Ebetino, Venice, FL (US); Shuting Sun, Temple City, CA (US); Charles E. McKenna, Pacific Palisades, CA (US); Keivan Sadrerafi, Pasadena, CA (US); and Philip Cherian, Pasadena, CA (US)
PCT Filed Jun. 25, 2019, PCT No. PCT/US2019/039018
§ 371(c)(1), (2) Date Dec. 23, 2020,
PCT Pub. No. WO2020/005964, PCT Pub. Date Jan. 2, 2020.
Claims priority of provisional application 62/690,053, filed on Jun. 26, 2018.
Prior Publication US 2021/0369849 A1, Dec. 2, 2021
Int. Cl. A61K 31/541 (2006.01); A61K 9/00 (2006.01); A61K 31/422 (2006.01); A61K 31/4439 (2006.01); A61K 31/496 (2006.01); A61K 31/5377 (2006.01); A61K 47/54 (2017.01); A61L 27/36 (2006.01); A61L 27/54 (2006.01)
CPC A61K 47/548 (2017.08) [A61K 9/0024 (2013.01); A61K 31/422 (2013.01); A61K 31/4439 (2013.01); A61K 31/496 (2013.01); A61K 31/5377 (2013.01); A61K 31/541 (2013.01); A61K 47/542 (2017.08); A61L 27/3608 (2013.01); A61L 27/54 (2013.01); A61L 2300/216 (2013.01); A61L 2300/404 (2013.01); A61L 2430/02 (2013.01)] 21 Claims
 
1. A compound according to Formula (1),

OG Complex Work Unit Chemistry
wherein the Oxazolidinone is an oxazolidinone antimicrobial or antibiotic compound or agent, and the Oxazolidinone includes the structure

OG Complex Work Unit Chemistry
to which the Linker is coupled, and
wherein the Linker is a releasable linker that when coupled to the Oxazolidinone and the bisphosphonate (BP) forms a carbamate selected from the group consisting of an aryl carbamate, an O-thioaryl carbamate, an S-thioaryl carbamate, or a phenyl carbamate;
wherein the aryl or phenyl group of the carbamate is coupled to the bisphosphonate (BP); and
wherein the oxazolidinone antimicrobial or antibiotic compound or agent for coupling to the bisphosphonate (BP) by the Linker is selected from the group consisting of: linezolid, tedizolid, eperizolid, posizolid, radezolid, ranbezolid, and sutezolid, antimicrobial or antibiotic compounds and agents.
 
18. A bone graft composition comprising: a bone graft material and a compound according to claim 1, wherein the compound is attached to, integrated with, chemisorbed to, or mixed with the bone graft material.