Labeling precursors with squaric acid coupling
AssigneeSCV Spezial-Chemikalien-Vertriebs GmbH
InventorsFrank Rösch, Lukas Greifenstein, Nils Engelbogen, Ralf Bergmann
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Abstract
The invention relates to a marking precursor incorporating a chelator or fluorination group for radiolabelling with 44Sc, 47Sc, 55Co, 62Cu, 64Cu, 67Cu, 66Ga, 67Ga, 68Ga, 89Zr, 86Y, 90Y, 90Nb, 99mTc, 111In, 135Sm, 140Pr, 159Gd, 149Tb, 160Tb, 161Tb, 165Er, 166Dy, 166Ho, 175Yb, 177Lu, 186Re, 188Re, 213Bi and 225Ac or with 18F, 131I or 211At, and one or two biological targeting vectors which are coupled to the chelator or fluorinating group via one or more squaric acid groups.
Claims15
A labeling precursor for a radiopharmaceutical whose structure (A) comprises:
- (A)=TV1-S2-QS-L2-Ch-L1-QS-S1-TV1
- wherein Ch is a chelator, TV1 is a targeting vector, QS is a squaric acid residue, L1 and L2 are linkers, and S1 and S2 are spacers;
- the chelator is formed from a compound of formula (B);
- the targeting vector is a fibroblast activation protein inhibitor (FAPi);
- QS is a squaric acid residue;
- L1 forms an amide residue;
- L2 is —(CH2)mNH— with m=1 through 10;
- and
- S1 and S2 are independently selected from —(CH2)nNH— with n=3 through 10.
A method for preparing a labeling precursor for a radiopharmaceutical comprising the steps of
- (a) providing a compound of formula (I):
- (b) adding a first linking group to the compound of formula (I) by reacting the compound of formula (I) with a compound of formula (II):
- (c) deprotecting the pentane dioic acid group of the compound formed in step (b) to form a compound of formula (III):
- (d) adding a second linking group to the deprotected compound of formula (III) by reacting the deprotected compound of formula (III) with ethylenediamine to form a bi-linked compound of formula (IV):
- (e) deprotecting the bi-linked compound of formula (IV) to form the bi-linked chelator of formula (V):
- (f) reacting a butyl amine spaced targeting vector of the formula (VI) with squaric acid to form a compound of the formula (VII):
- (g) reacting the squaric acid-modified targeting vector of formula (VII) with the bi-linked chelator of formula (V) to form the labeling precursor of formula (E):
A method of diagnosing and/or treating cancer comprising administering a radiopharmaceutical comprising a radioactive isotope and a compound of formula (E) to diagnose and/or treat cancer expressing FAP
Dependencies are inferred from the claim text.