Compounds and methods for imaging immune activity
AssigneeBoard of Regents, The University of Texas System
InventorsDavid PIWNICA-WORMS, Federica PISANESCHI, Seth GAMMON
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Abstract
The present disclosure provides radiolabeled compounds of the formula: (I) and (II), as well as precursor compounds of the formula: (VII) wherein the variables are defined herein. The present disclosure also provides radiopharmaceutical compositions comprising the radiolabeled compounds disclosed herein as well as precursor compositions comprising the precursor compounds disclosed herein. The present disclosure further provides methods of imaging using the radiolabeled compounds and/or radiopharmaceutical compositions of the present disclosure as well as kits for the preparation of the radiolabeled compounds and radiopharmaceutical compositions disclosed herein.
Claims101
A radiolabeled compound of the formula:
- wherein:
- n is 0-6;
- R1 is —ORa or —NRbRc, wherein:
- Ra is hydrogen, —S(O)2OH, or a hydroxyl protecting group;
- or
- alkyl(C≤12), cycloalkyl(C≤12), heterocycloalkyl(C≤12), aralkyl(C≤12), acyl(C≤12), —C(O)-alkoxy(C≤12), alkylsulfonyl(C≤12), alkoxysulfonyl(C≤12), alkylaminosulfonyl(C≤12), dialkylaminosulfonyl(C≤12), or a substituted version of any of these groups;
- Rb and Rc are each independently hydrogen or a monovalent amine protecting group;
- or
- alkyl(C≤12), aralkyl(C≤12), acyl(C≤12), or a substituted version of any of these groups;
- or
- Rb and Rc are taken together and are a divalent amine protecting group;
- R2, in each instance, is independently hydrogen, hydroxy, halo, amino, nitro, carboxy, or mercapto;
- or
- —Y—Rd, wherein:
- Y is a covalent bond, —C(O)—, —OC(O)—, —NHC(O)—;
- Rd is alkyl(C≤12), alkoxy(C≤12), alkylamino(C≤12), dialkylamino(C≤12), or a substituted version of any of these groups;
- R3 is hydrogen, —ORe or —NRfRg, wherein:
- Re is hydrogen, —S(O)2OH, or a hydroxyl protecting group;
- or
- alkyl(C≤12), cycloalkyl(C≤12), heterocycloalkyl(C≤12), aralkyl(C≤12), acyl(C≤12), —C(O)-alkoxy(C≤12), alkylsulfonyl(C≤12), alkoxysulfonyl(C≤12), alkylaminosulfonyl(C≤12), dialkylaminosulfonyl(C≤12), or a substituted version of any of these groups;
- Rf and Rg are each independently hydrogen or a monovalent amine protecting group;
- or
- alkyl(C≤12), aralkyl(C≤12), acyl(C≤12), or a substituted version of any of these groups;
- or
- Rf and Rg are taken together and are a divalent amine protecting group;
- R4 and R5 are each independently absent, hydrogen, hydroxy, amino, cyano, nitro, or halo;
- or
- alkyl(C≤12), aryl(C≤12), heteroaryl(C≤12), acyl(C≤12), alkoxy(C≤12), alkylamino(C≤12), dialkylamino(C≤12), or a substituted version of any of these groups;
- and
- X1 and X2 are each independently —C═ or —N═;
- or a pharmaceutically acceptable salt of either of these formulae.
A precursor compound of the formula:
- wherein:
- m is 0-6;
- R6 is —ORh or —NRiRj, wherein:
- Rh is —S(O)2OH or a hydroxyl protecting group;
- or
- alkyl(C≤12), cycloalkyl(C≤12), heterocycloalkyl(C≤12), aralkyl(C≤12), acyl(C≤12), —C(O)-alkoxy(C≤12), alkylsulfonyl(C≤12), alkoxysulfonyl(C≤12), alkylaminosulfonyl(C≤12), dialkylaminosulfonyl(C≤12), or a substituted version of any of these groups;
- Ri and Rj are each independently hydrogen or a monovalent amine protecting group;
- or
- alkyl(C≤12), aralkyl(C≤12), acyl(C≤12), or a substituted version of any of these groups;
- or
- Ri and Rj are taken together and are a divalent amine protecting group;
- R7, in each instance, is independently hydroxy, halo, amino, nitro, carboxy, or mercapto;
- or
- —Y—Rk, wherein:
- Y is a covalent bond, —C(O)—, —OC(O)—, —NHC(O)—;
- Rk is alkyl(C≤12), alkoxy(C≤12), alkylamino(C≤12), dialkylamino(C≤12), or a substituted version of any of these groups;
- and
- R8 and R9 are each independently halo or hydroxy;
- or
- alkoxy(C≤12), substituted alkoxy(C≤12), acyloxy(C≤12), or substituted acyloxy(C≤12);
- or
- R8 and R9 are taken together and is —O—X3—O—, wherein:
- X3 is alkanediyl(C≤12), substituted alkanediyl(C≤12), or a boronic acid protecting group;
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.