US 11,850,286 B2
Sulfamide linker, conjugates thereof, and methods of preparation
Jorge Merijn Mathieu Verkade, Eindhoven (NL); Maria Antonia Wijdeven, Lent (NL); Petrus Josephus Jacobus Maria Van De Sande, Eindhoven (NL); Sander Sebastiaan Van Berkel, Lent (NL); and Floris Louis Van Delft, Nijmegen (NL)
Assigned to SYNAFFIX B.V., Oss (NL)
Filed by Synaffix B.V., Oss (NL)
Filed on Oct. 5, 2020, as Appl. No. 17/063,537.
Application 17/063,537 is a continuation of application No. 15/581,226, filed on Apr. 28, 2017, granted, now 10,792,369.
Application 15/581,226 is a continuation of application No. 15/360,610, filed on Nov. 23, 2016, granted, now 9,636,421.
Application 15/360,610 is a continuation of application No. PCT/NL2015/050697, filed on Oct. 5, 2015.
Claims priority of application No. 14187615 (EP), filed on Oct. 3, 2014.
Prior Publication US 2021/0030886 A1, Feb. 4, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 47/68 (2017.01); C07K 16/32 (2006.01)
CPC A61K 47/6803 (2017.08) [A61K 47/6811 (2017.08); A61K 47/6851 (2017.08); A61K 47/6855 (2017.08); A61K 47/6889 (2017.08); C07K 16/32 (2013.01)] 28 Claims
OG exemplary drawing
 
1. A bioconjugate, comprising a biomolecule B and a target molecule D, wherein the bioconjugate further comprises a group according to formula (1):

OG Complex Work Unit Chemistry
covalently linked to an alpha-end at one side of the formula (1) and an omega-end at the other side of the formula (1), the alpha-end comprising the biomolecule B and the omega-end comprising the target molecule D,
wherein:
the wavy lines indicate covalent linkages to the alpha-end and the omega-end,
the biomolecule B is selected from the group consisting of proteins polypeptides, peptides, glycans, nucleic acids, oligonucleotides, polysaccharides, oligosaccharides and enzymes;
the target molecule D is selected from the group consisting of colchicine, vinca alkaloids, anthracyclines camptothecins taxanes, calicheamycins, tubulysins, an inhibitory peptide, amanitin, deBouganin, duocarmycins, maytansines, auristatins ander pyrrolobenzodiazepines;
a is 0 or 1; and
R1 is selected from the group consisting of hydrogen, C1-C24 alkyl groups, C3-C24 cycloalkyl groups, C2-C24 (hetero)aryl groups, C3-C24 alkyl(hetero)aryl groups and C3-C24 (hetero)arylalkyl groups, the C1-C24 alkyl groups, C3-C24 cycloalkyl groups, C2-C24 (hetero)aryl groups, C3-C24 alkyl(hetero)aryl groups and C3-C24 (hetero)arylalkyl groups optionally substituted and optionally interrupted by one or more heteroatoms selected from O, S and NR3 wherein R3 is independently selected from the group consisting of hydrogen and C1-C4 alkyl groups, or R1 is a target molecule D, wherein the target molecule is optionally connected to N via a spacer moiety,
or a salt of the bioconjugate.