US 12,325,715 B2
Fluorous metal chelates compositions
Eric T. Ahrens, Encinitas, CA (US); Stephen Adams, Poway, CA (US); and Chao Wang, La Jolla, CA (US)
Assigned to THE REGENTS OF THE UNIVERSITY OF CALIFORNIA, Oakland, CA (US)
Appl. No. 17/311,299
Filed by The Regents of the University of California, Oakland, CA (US)
PCT Filed Dec. 9, 2019, PCT No. PCT/US2019/065279
§ 371(c)(1), (2) Date Jun. 4, 2021,
PCT Pub. No. WO2020/118307, PCT Pub. Date Jun. 11, 2020.
Claims priority of provisional application 62/777,008, filed on Dec. 7, 2018.
Prior Publication US 2022/0033424 A1, Feb. 3, 2022
Int. Cl. C07F 11/00 (2006.01); A61K 49/10 (2006.01); A61K 49/18 (2006.01); C07F 15/02 (2006.01)
CPC C07F 11/005 (2013.01) [A61K 49/106 (2013.01); A61K 49/1806 (2013.01); C07F 15/025 (2013.01)] 19 Claims
 
1. A compound comprising an salicylidene-tris(aminomethyl) ethane (SALTAME) core comprising a metal-binding moiety capable of binding metal ions, wherein the compound comprises at least one fluorine-19 (19F) and the compound is selected from:
Formula (A)

OG Complex Work Unit Chemistry
wherein
X is 18F, or
X is selected from —(CH2)mCH3, —O(CH2) CH3, —(CH2)OH, —(CH2)mNH2,

OG Complex Work Unit Chemistry
wherein X comprises one or more of 11C, 13N, or 15O and m is an integer from 0 to 20,
M is a metal ion selected from Fe3+, Fe2+, Ga3+, Mn2+, Mn3+, Mn4+, Ni2+, Cu2+, Zn2+, Co3+, or Cr3+, and
R1 to R12 are each independently selected from: H, CH3, perfluorohexyl (PFH), perfluorooctyl (PFO), Me, CF3, O—(CF2)m—CF3, (CF2)n—CF3, and O—CF2—(OCF2CF2)n—O—Y, wherein n is 0 to 20, and Y is CF3, CF2—CF3 or CF2—CF2—CF3;
or
Formula (B)

OG Complex Work Unit Chemistry
wherein
X is 18F, or
X is selected from —(CH2)mCH3, —O(CH2)mCH3, —(CH2)mOH, —(CH2)mNH2,

OG Complex Work Unit Chemistry
wherein X comprises one or more of 11C, 13N, or 15O and m is an integer from 0 to 20,
Rf is (CF2)—CF3 or O—(CF2)—CF3,
j is an integer from 0 to 20 ,
M is a metal ion, and
n is an integer from 0 to 20.