Alkynes and methods of reacting alkynes with 1,3-dipole-functional compounds

• US 8,940,859 B2
• Filed: 03/13/2012
• Issued: 01/27/2015
• Est. Priority Date: 11/21/2007
• Status: Active Grant

• Current Assignee: The University of Georgia Research Foundation, Inc.
• Original Assignee: The University of Georgia Research Foundation, Inc.
• Inventors: Boons, Geert-Jan, Guo, Jun, Ning, Xinghai, Wolfert, Margaretha
• Primary Examiner(s): Yoo, Sun Jae
• Application Number:
  US13/418,676
• Publication Number:
  US 20120172575A1
• Time in Patent Office: 1,050 Days
• US Class Current: 530/300
• CPC Class Codes: A61K 47/54 the modifying agent being an organic compound
• CPC Class Codes: A61K 47/542 Carboxylic acids, e.g. a fatty acid or an amino acid
• CPC Class Codes: A61K 47/61 the organic macromolecular compound being a polysaccharide or a derivative thereof
• CPC Class Codes: A61K 47/62 the modifying agent being a protein, peptide or polyamino acid
• CPC Class Codes: A61K 47/64 Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent peptidic linkers A61K47/65
• CPC Class Codes: A61K 47/6921 the form being a particulate, a powder, an adsorbate, a bead or a sphere
• CPC Class Codes: A61K 49/0021 the fluorescent group being a small organic molecule
• CPC Class Codes: A61K 49/0043 Fluorescein, used in vivo
• CPC Class Codes: A61K 49/0052 Small organic molecules oligomers, polymers, dendrimers A61K49/0054
• CPC Class Codes: A61P 37/04 Immunostimulants
• CPC Class Codes: C07C 211/42 with six-membered aromatic rings being part of the condensed ring systems
• CPC Class Codes: C07C 251/44 with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
• CPC Class Codes: C07C 251/58 of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
• CPC Class Codes: C07C 2603/36 containing eight-membered rings
• CPC Class Codes: C07C 271/34 with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 35/37 with a hydroxy group on a condensed system having three rings
• CPC Class Codes: C07C 49/683 having unsaturation outside the aromatic rings
• CPC Class Codes: C07D 249/16 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 261/20 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 271/12 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 307/94 : spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
• CPC Class Codes: C07D 311/90 : with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
• CPC Class Codes: C07D 495/04 : Ortho-condensed systems
• CPC Class Codes: C07H 21/00 : Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
• CPC Class Codes: C07K 14/00 : Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
• CPC Class Codes: C07K 2/00 : Peptides of undefined number of amino acids; Derivatives thereof
• CPC Class Codes: G01N 33/582 : with fluorescent label

Abstract

1,3-Dipole-functional compounds (e.g., azide functional compounds) can be reacted with certain alkynes in a cyclization reaction to form heterocyclic compounds. Useful alkynes (e.g., strained, cyclic alkynes) and methods of making such alkynes are also disclosed. The reaction of 1,3-dipole-functional compounds with alkynes can be used for a wide variety of applications including the immobilization of biomolecules on a substrate.

Claims

1. A dibenzocyclooctyne having the formula:

2. A dibenzocyclooctyne having the formula:

3. A dibenzocyclooctyne having the formula:

4. A method of preparing a heterocyclic compound, the method comprising:

combining at least one azide-functional compound with at least one dibenzocyclooctyne according to claim 3; and

allowing the at least one azide-functional compound and the at least one alkyne to react under conditions effective to form the heterocyclic compound.

5. An alkyne of the formula: