US 11,851,407 B2
Synthesis of the radiolabeled prostate-specific membrane antigen (PSMA) inhibitor [18F]DCFPYL
Hayden T. Ravert, Bel Air, MD (US); Daniel P. Holt, Severna Park, MD (US); Ying Chen, Lutherville-Timonium, MD (US); Ronnie C. Mease, Fairfax, VA (US); Hong Fan, Timonium, MD (US); Martin G. Pomper, Baltimore, MD (US); and Robert F. Dannals, Sparks, MD (US)
Assigned to THE JOHNS HOPKINS UNIVERSTY, Baltimore, MD (US)
Filed by The Johns Hopkins University, Baltimore, MD (US)
Filed on Mar. 9, 2021, as Appl. No. 17/195,895.
Application 17/195,895 is a continuation of application No. 16/308,128, granted, now 10,947,197, previously published as PCT/US2017/036681, filed on Jun. 9, 2017.
Claims priority of provisional application 62/348,391, filed on Jun. 10, 2016.
Prior Publication US 2022/0055991 A1, Feb. 24, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 213/42 (2006.01); A61K 51/04 (2006.01); A61P 35/00 (2006.01); C07B 59/00 (2006.01); C07D 213/82 (2006.01)
CPC C07D 213/42 (2013.01) [A61K 51/0455 (2013.01); A61K 51/0497 (2013.01); A61P 35/00 (2018.01); C07B 59/002 (2013.01); C07D 213/82 (2013.01)] 34 Claims
 
1. A method of synthesizing 2-(3-{1-carboxy-5-[(6-[18F]fluoro-pyridine-3-carbonyl)-amino]-pentyl}-ureido)-pentanedioic acid [18F]DCFPyL),

OG Complex Work Unit Chemistry
the method comprising:
(i) radiofluorinating a DCFPyL precursor comprising ester moiety protecting groups to form a radiofluorinated DCPFPyL precursor;
(ii) deprotecting the ester moiety protecting groups of the radiofluorinated DCPFPyL precursor of step (i) with phosphoric acid to form [18F]DCFPyL in a reaction mixture; and
(iii) purifying the [18F]DCFPyL from the reaction mixture of step (ii) to provide [18F]DCFPyL.