3-aryl propiolonitrile compounds for thiol labeling

• US 10,131,626 B2
• Filed: 04/06/2017
• Issued: 11/20/2018
• Est. Priority Date: 07/04/2013
• Status: Active Grant

• Current Assignee: Centre National De La Recherche Scientifique, Universite De Strasbourg (Financière Meeschaert SA)
• Original Assignee: Centre National De La Recherche Scientifique, Universite De Strasbourg (Financière Meeschaert SA)
• Inventors: Wagner, Alain, Koniev, Oleksandr
• Primary Examiner(s): Muresan, Ana Z
• Application Number:
  US15/480,420
• Publication Number:
  US 20170210700A1
• Time in Patent Office: 593 Days
• Field of Search: None
• CPC Class Codes: C07B 2200/05 Isotopically modified compounds, e.g. labelled
• CPC Class Codes: C07C 255/34 with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
• CPC Class Codes: C07C 255/35 the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
• CPC Class Codes: C07C 255/37 the carbon skeleton being further substituted by etherified hydroxy groups
• CPC Class Codes: C07C 255/41 the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
• CPC Class Codes: C07C 255/42 the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
• CPC Class Codes: C07C 255/43 the carbon skeleton being further substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 255/44 at least one of the singly-bound nitrogen atoms being acylated
• CPC Class Codes: C07C 2602/24 the ring system containing nine carbon atoms, e.g. perhydroindane
• CPC Class Codes: C07C 271/16 to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 271/22 to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
• CPC Class Codes: C07C 271/28 to a carbon atom of a non-condensed six-membered aromatic ring
• CPC Class Codes: C07C 275/42 being further substituted by carboxyl groups
• CPC Class Codes: C07C 309/42 having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings
• CPC Class Codes: C07C 319/02 of thiols
• CPC Class Codes: C07C 323/42 Y being a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 323/60 with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
• CPC Class Codes: C07C 331/28 having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07C 335/22 being further substituted by carboxyl groups
• CPC Class Codes: C07D 207/452 with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 207/46 : with hetero atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 249/06 : with aryl radicals directly attached to ring atoms
• CPC Class Codes: C07D 265/38 : [b, e]-condensed with two six-membered rings
• CPC Class Codes: C07D 311/82 : Xanthenes
• CPC Class Codes: C07D 311/88 : Nitrogen atoms
• CPC Class Codes: C07D 337/04 : not condensed with other rings
• CPC Class Codes: C07D 403/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 405/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 495/04 : Ortho-condensed systems
• CPC Class Codes: C07F 5/04 : Esters of boric acids
• CPC Class Codes: C07F 7/08 : Compounds having one or more C—Si linkages
• CPC Class Codes: C07F 7/081 : comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
• CPC Class Codes: C07F 9/5442 : Aromatic phosphonium compounds (P-C aromatic linkage)
• CPC Class Codes: C07K 1/13 : Labelling of peptides
• CPC Class Codes: C07K 14/70596 : Molecules with a "CD"-designation not provided for elsewhere
• CPC Class Codes: C07K 16/2863 : against receptors for growth factors, growth regulators
• CPC Class Codes: C07K 16/30 : from tumour cells
• CPC Class Codes: C07K 16/32 : against translation products of oncogenes
• CPC Class Codes: C07K 19/00 : Hybrid peptides , i.e. peptides covalently bound to nucleic acids, or non-covalently bound protein-protein complexes
• CPC Class Codes: C07K 2317/24 : containing regions, domains or residues from different species, e.g. chimeric, humanized or veneered
• CPC Class Codes: C07K 2317/76 : Antagonist effect on antigen, e.g. neutralization or inhibition of binding
• CPC Class Codes: C12N 9/2462 : Lysozyme (3.2.1.17)
• CPC Class Codes: C12Y 302/01017 : Lysozyme (3.2.1.17)
• CPC Class Codes: G01N 33/58 : involving labelled substances G01N33/53 takes precedence
• CPC Class Codes: G01N 33/84 : involving inorganic compounds or pH

Abstract

The present invention relates to a process for labeling compounds comprising thiol moieties with 3-arylpropiolonitrile compounds, to 3-arylpropiolonitrile compounds substituted with tag moieties and to specific 3-arylpropiolonitrile linkers.

Claims

1. A process for the conjugation of a protein comprising at least one cysteine residue having a thiol moiety, the process comprising contacting the protein with a compound of formula (I):

2. The process of claim 1, wherein the linker group is COO, NH—

C(═

O)—

NH, NH—

C(═

O)—

O, a triazole or CONH.