US 12,135,325 B2
Organotellurium compounds, compositions and methods of use thereof
Mark Nitz, Toronto (CA); Landon J. Edgar, Midhurst (CA); Bradly G. Wouters, Toronto (CA); David Hedley, Toronto (CA); Lisa M. Willis, Toronto (CA); Matthew A. Lumba, Toronto (CA); Hanuel Park, London (CA); and Ravi N. Vellanki, Toronto (CA)
Assigned to The Governing Council of the University of Toronto, Toronto (CA); and University Health Network, Toronto (CA)
Filed by The Governing Council of the University of Toronto, Toronto (CA); and University Health Network, Toronto (CA)
Filed on Sep. 18, 2020, as Appl. No. 17/024,913.
Application 17/024,913 is a continuation of application No. 16/245,328, filed on Jan. 11, 2019, granted, now 10,816,552.
Application 16/245,328 is a continuation of application No. 15/505,197, granted, now 10,222,380, issued on Mar. 5, 2019, previously published as PCT/CA2015/050793, filed on Aug. 20, 2015.
Claims priority of provisional application 62/165,002, filed on May 21, 2015.
Claims priority of provisional application 62/039,762, filed on Aug. 20, 2014.
Prior Publication US 2021/0102949 A1, Apr. 8, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 345/00 (2006.01); C07D 421/06 (2006.01); C07H 15/04 (2006.01); G01N 33/569 (2006.01); G01N 33/58 (2006.01)
CPC G01N 33/58 (2013.01) [C07D 345/00 (2013.01); C07D 421/06 (2013.01); C07H 15/04 (2013.01); G01N 33/569 (2013.01); G01N 2458/15 (2013.01); G01N 2560/00 (2013.01)] 21 Claims
 
1. A kit capable of mass detection assay, the kit comprising:
a plurality of mass tags, each mass tag comprising a tellurophene compound of the below formula (I);

OG Complex Work Unit Chemistry
wherein
A is a naturally occurring isotope of Te;
R1 is selected from H, unsubstituted or substituted C1-C20alkyl, unsubstituted or substituted C3-C20cycloalkyl, unsubstituted or substituted aryl and an electron withdrawing group;
L is C1-30alkylene, unsubstituted or substituted with one or more substituents, and/or optionally interrupted with one or more heteromoieties independently selected from O, S, NR7, and/or optionally interrupted with one or more of C(O) and C(S);
R7 is independently selected from H, PG and C1-6alkyl;
X is a reactive functional group selected from halo, OH, Ots, Oms, C(O)H, C(O)OR8, C(O)NR9R10, O—C(O)—OR11, O—C(O)—NR12, C(O)ONR13R14, C(O)R15, C(O)SR16, NR17R18, or a maleimide,
R8 is selected from H, C1-6alkyl, aryl and C1-6alkylenearyl, wherein the latter three groups are unsubstituted or substituted with one or more of halo and NO2;
R9 and R10 are independently selected from H, C1-6alkyl, aryl and C1-6alkylenearyl, wherein the latter three groups are unsubstituted or substituted with one or more of halo and NO2, or
R9 and R10, together with the N atom to which they are bonded, form a 4 to 12 membered monocyclic or bicyclic, saturated or unsaturated ring unsubstituted or substituted with one or more ═O, ═S, halo and C1-6alkyl;
R11 is selected from C1-6alkyl, aryl and C1-6alkylenearyl, wherein the latter three groups are unsubstituted or substituted with one or more of halo and NO2;
R12 is selected from C1-6alkyl, aryl and C1-6alkylenearyl, wherein the latter three groups are unsubstituted or substituted with one or more of halo and NO2;
R13 and R14 are independently selected from H, C1-6alkyl, aryl and C1-6alkylenearyl, wherein the latter three groups are unsubstituted or substituted with one or more of halo and NO2, or
R13 and R14, together with the N atom to which they are bonded, form a 4 to 12 membered monocyclic or bicyclic, saturated or unsaturated ring unsubstituted or substituted with one or more ═O, ═S, halo and C1-6alkyl;
R15 is halo;
R16 is selected from C1-6alkyl, aryl and C1-6alkylenearyl, wherein the latter three groups are unsubstituted or substituted with one or more of halo and NO2;
R17 and R18 are independently selected from H, C(O)C1-6 alkyl, C1-6alkyl, aryl and C1-6alkylenearyl, wherein the latter three groups are unsubstituted or substituted with one or more of halo and NO2, or R17 and R18, together with the N atom to which they are bonded, form a 4 to 12 membered monocyclic or bicyclic, saturated or unsaturated ring unsubstituted or substituted with one or more ═O, ═S, halo and C1-6alkyl; and
one or more available hydrogens are optionally replaced with D;
or a salt and/or solvate thereof;
with proviso that when X is C(O)OR19 and R19 is H or C1-6alkyl, L is not C1-8alkylene; and
when X is OH, L is not C1-2alkylene; and
wherein each mass tag comprises a distinct tellurium isotope.