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US 5,395,608 AGranted
Triamine chelants, their derivatives, complexes and conjugates
AssigneeThe Curators of the University of Missouri
InventorsDavid E. Troutner, Christy S. John, Maroor R. A. Pillai
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Abstract
A group of functionalized triamine chelants and their derivatives that form complexes with radioactive metal ions are disclosed. The complexes can be covalently attached to a protein or an antibody or antibody fragment and used for therapeutic and/or diagnostic purposes. The chelants are of the formula: ##STR1## wherein n, m, R, R.sup.1, R.sup.2 and L are defined in the specification.
Claims22
A compound which is 2,2,12,12-tetramethyl-4,7,10-triaza-7-(p-aminobenzyl)-1,13-tridecane dithiol.
A complex which comprises a compound of the formula ##STR13## wherein:
- R represents independently hydrogen, C.sub.1 -C.sub.3 alkyl, or benzyl;
- R.sup.1 represents --CH.sub.2 C(CH.sub.3).sub.2 SH, --(CH.sub.2).sub.2 NH.sub.2, --(CH.sub.2).sub.2 SH, ##STR14## Q represents hydrogen, C.sub.1 -C.sub.3 alkyl or phenyl;
- R.sup.2 represents hydrogen, --CH.sub.2 CO.sub.2 H, --CH.sub.2 CH.sub.2 CO.sub.2 H, or --(CH.sub.2).sub.2 NH.sub.2 ;
- m and n are independently 2, 3, or 4;
- L is a linker/spacer group covalently bonded to, and replaces one hydrogen atom of the nitrogen atom to which it is joined, said linker/spacer group being represented by the formula ##STR15## wherein:
- Y is selected from the group consisting of nitro, amino, isothiocyanato, semicarbazido, thiosemicarbazido, carboxyl, bromoacetamido and maleimido;
- q is 1, 2, or 3;
- or
- a pharmaceutically acceptable salt thereof;
- and complexed with an ion of a metal selected from the group consisting of .sup.99m Tc, .sup.105 Rh, .sup.109 Pd, .sup.57 Co, .sup.186 Re, .sup.188 Re, .sup.97 Ru, .sup.111 In, .sup.113m In, .sup.67 Ga, and .sup.68 Ga.
7 more elements
A conjugate comprising a compound of the formula ##STR17## wherein:
- R represents independently hydrogen, C.sub.1 -C.sub.3 alkyl, or benzyl;
- R.sup.1 represents --CH.sub.2 C(CH.sub.3).sub.2 SH, --(CH.sub.2).sub.2 NH.sub.2, --(CH.sub.2).sub.2 SH, ##STR18## Q represents hydrogen, C.sub.1 -C.sub.3 alkyl or phenyl;
- R.sup.2 represents hydrogen, --CH.sub.2 CO.sub.2 H, --CH.sub.2 CH.sub.2 CO.sub.2 H, or --(CH.sub.2).sub.2 NH.sub.2 ;
- m and n are independently 2, 3, or 4;
- L is a linker/spacer group covalently bonded to, and replaces one hydrogen atom of the nitrogen atom to which it is joined, said linker/spacer group being represented by the formula ##STR19## wherein:
- Y is selected from the group consisting of nitro, amino, isothiocyanato, semicarbazido, thiosemicarbazido, carboxyl, bromoacetamido and maleimido;
- q is 1, 2, or 3;
- or
- a pharmaceutically acceptable salt thereof;
- complexed with an ion of a metal selected from the group consisting of .sup.99m Tc, .sup.105 Rh, .sup.109 Pd, .sup.57 Co. .sup.186 Re, .sup.188 Re, .sup.97 Ru, .sup.111 In, .sup.113m In, .sup.67 Ga, and .sup.68 Ga, with the proviso that when R.sup.2 is --CH.sub.2 CO.sub.2 H or --CH.sub.2 CH.sub.2 CO.sub.2 H, then the radioactive metal ion is selected from the group consisting of .sup.186 Re, .sup.188 Re, .sup.99m Tc, .sup.111 In, .sup.113m In, .sup.67 Ga, and .sup.68 Ga;
- and
- covalently attached to a protein or an antibody or antibody fragment.
9 more elements
A pharmaceutical formulation comprising a conjugate having a compound of the formula ##STR21## wherein:
- R represents independently hydrogen, C.sub.1 -C.sub.3 alkyl, or benzyl;
- R.sup.1 represents --CH.sub.2 C(CH.sub.3).sub.2 SH, --(CH.sub.2).sub.2 NH.sub.2, --CH.sub.2).sub.2 SH, ##STR22## Q represents hydrogen, C.sub.1 -C.sub.3 alkyl or phenyl;
- R.sup.2 represents hydrogen, --CH.sub.2 CO.sub.2 H, --CH.sub.2 CH.sub.2 CO.sub.2 H, or --(CH.sub.2).sub.2 NH.sub.2 ;
- m and n are independently 2, 3, or 4;
- L is a linker/spacer group covalently bonded to, and replaces one hydrogen atom of the nitrogen atom to which it is joined, said linker/spacer group being represented by the formula ##STR23## wherein:
- Y is selected from the group consisting of nitro, amino, isothiocyanato, semicarbazido, thiosemicarbazido, carboxyl, bromoacetamido and maleimido;
- q is 1, 2, or 3;
- or
- a pharmaceutically acceptable salt thereof;
- and
- complexed with an ion of a metal selected from the group consisting of .sup.99m Tc, .sup.105 Rh, .sup.109 Pd, .sup.57 Co, .sup.186 Re, .sup.188 Re, .sup.97 Ru, .sup.111 In, .sup.113m In, .sup.67 Ga, and .sup.68 Ga, with the proviso that when R.sup.2 is --CH.sub.2 CO.sub.2 H or --CH.sub.2 CH.sub.2 CO.sub.2 H, then the radioactive metal ion is selected from the group consisting of .sup.186 Re, .sup.188 Re, .sup.99m Tc, .sup.111 In, .sup.113m In, .sup.67 Ga, and .sup.68 Ga;
- and
- covalently attached to a protein or an antibody or antibody fragment;
- and
- a physiologically acceptable carrier.
12 more elements
Dependencies are inferred from the claim text.