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US 11,535,623 B2Granted
Cryptate compounds
AssigneesAustralian Nuclear Science and Technology Organisation, The Australian National University
InventorsSuzanne Virginia Smith, Eskender Mume, Gary James Perkins
Life of this patent
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Abstract
Disclosed herein is a method for coupling a first compound having the formula (I) with a second compound that contains a carbonyl group. Also disclosed herein are compounds that can be formed by this method, and uses for such compounds.
Claims11
A method for coupling a first compound of formula (I):
- wherein:
- each R1 and R2 is independently selected from the group consisting of hydrogen, halogen, CH3, COOH, NO2, CH2OH, H2PO4, HSO3, CN, C(═O)NH2 and CHO;
- n=2,3 or 4;
- each X is independently NH or S, provided that at least one X is NH;
- each Z is an optional spacing group which, when present, is independently selected from the group consisting of optionally substituted C1-C10 alkyl, optionally substituted aryl and optionally substituted heterocycle;
- and
- each Y is independently selected from the group consisting of hydrogen, halogen, hydroxyl, nitro, optionally substituted amino, optionally substituted alkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted heterocycle, isothiocyanate, cyano, —NH—COCH2Br, —COOR′ and —NH—CO—CH═CH—COOR′, wherein R′ is hydrogen, an optionally substituted alkyl, or an optionally substituted aryl, provided that at least one Y is or contains a primary amine;
- wherein the compound of formula (I) is not complexed with a metal ion;
- with a second compound that contains a carbonyl group that is an aldehyde or ketone, to form a coupling reaction product, the method comprising the steps of:
- (i) dissolving the compound of formula (I) in a solvent comprising water to form a solution;
- and
- (ii) adding to the solution the second compound that contains a carbonyl group;
- wherein the pH of the solution is from about 4 to about 5;
- whereby substantially all coupling will occur at the primary amine of the compound of formula (I);
- whereby
- the second compound reacts with and couples to the compound of formula (I) by way of a Schiff's base condensation between the primary amine of the compound of formula (I) and the carbonyl group of the second compound.
13 more elements
Dependencies are inferred from the claim text.