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Publication Number
US-9974869-B2
Publication Date
2018-05-22
Expiration Date
Abstract
Compounds as defined herein are provided which are useful in (1) diagnostic methods for detecting and/or identifying cells presenting PSMA; (2) compositions comprising a compound of the invention together with a pharmaceutically acceptable diluent; and (3) methods for imaging prostate cancer cells.
Core Innovation
The disclosure describes compounds of a specified formula in which a divalent linking group is bonded to a chelating agent. The divalent linking group includes an L2 segment of the form —(CH2)tN(H)—, where t is 1 to 30, and an L3 segment, where the # end of L3 is attached to a dibenzocyclooctyne or triazolyl group.
A Y spacer is defined as —CH2CH2(OCH2CH2)n—, where n is 1 to 20, and the **-end is attached to Z. Z is selected from carboxylate, amido, alkoxy, and sulfonamide/sulfonate type groups, including —C(O)O—, —C(O)N(R00)—, —OC(O)—, —N(R00)C(O)—, —S(O)2N(R00)—, and —N(R00)S(O)2—, where each R00 is independently hydrogen or C1-C6 alkyl.
The chelating agent is optionally associated with a PET-active or therapeutic radioisotope. The disclosure includes chelating agents such as DOTA-, DTPA-, NOTA-, PCTA-, DO3A-, desferrioxamine-, and TETA-type chelators, and describes radiolabelable constructs and labeled compounds.
Claims Coverage
The independent claims cover a compound defined by a divalent linking group bonded to a chelating agent, with L2, L3, Y, and Z substructures and attachment points specified. The claims also include optional association of the chelating agent with a PET-active or therapeutic radioisotope. Overall, the claims present four inventive features centered on the linked chelator architecture, the defined linker segments, and the optional radioisotope association.
Divalent linking group bonded to a chelating agent
A compound in which a divalent linking group is bonded to a chelating agent.
L2 segment with amino-linked methylene chain
L2 is —(CH2)tN(H)—, where t is 1 to 30, and the *-end is attached to the chelating agent.
L3 segment attached to dibenzocyclooctyne or triazolyl group
L3 has a defined carbonyl/heteroatom-containing linkage, where the # end is attached to the dibenzocyclooctyne or triazolyl group.
Y spacer and Z group selection
Y is —CH2CH2(OCH2CH2)n—, where n is 1 to 20, and the **-end is attached to Z; Z is selected from the enumerated carboxylate, amido, alkoxy, and sulfonamide/sulfonate forms.
Optional PET-active or therapeutic radioisotope association
The chelating agent is optionally associated with a PET-active or therapeutic radioisotope.
The claims define a chelator-linked compound architecture built from L2, L3, Y, and Z, with L3 attached to a dibenzocyclooctyne or triazolyl group and with optional PET-active or therapeutic radioisotope association.
Stated Advantages
Supports diagnostic PET imaging and therapeutic radiotherapy using PSMA-targeting small-molecule chelated inhibitors.
Stability findings address acid/base stability while maintaining PSMA binding potency.
Documented Applications
Tc-labeled SPECT probe based on a CTT-54 conjugate using a bifunctional chelator p-SCN-Bn-DTPA.
Radiolabelable constructs associated with PET-active radioisotopes.
Imaging one or more cancer cells in a patient using a compound labeled with a PET-active radioisotope and performing PET imaging.
In vivo imaging of prostate cancer cells or tumor vasculature using administered labeled compounds.
Diagnostic PET imaging and therapeutic radiotherapy.
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