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US 12,466,855 B2Granted
Labeled oxytocin and method of manufacture and use
AssigneesTonix Pharma Limited, Aarhus University
InventorsSteen Jakobsen, Michael Winterdahl, Erik Nguyen Nielsen, David C. Yeomans, Dean Carson
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Abstract
Disclosed are 13N-oxytocin molecules, methods of manufacture of 13N-oxytocin molecules and methods of use of 13N-oxytocin molecules in the determination of the distribution and kinetics of 13N-oxytocin molecules after craniofacial or other application methods.
Claims9
A method of manufacturing a compound of Formula IV, wherein the compound is a 13N-labeled oxytocin peptide comprising the amino acid sequence of SEQ ID NO:
- 1, the method comprising:
- a) converting a compound of Formula (I):
- into a compound of Formula (II):
- using a R-LG reagent, wherein LG is a leaving group selected from a group comprising CN, OH, O-Acyl, OAt, OBt, Cl, 1-imidazolyl;
- and
- wherein R is P(═O)(OR1)(OR2);
- wherein R1 and R2 are independently C1-C6 alkyl or C6-C14 aryl, wherein the C1-C6 alkyl and C6-C14 aryl are independently optionally substituted by halogen, cyano, or C1-C6 alkyl;
- and
- wherein PG1 is an amine protecting group;
- b) reacting a compound of Formula (II) with gaseous 13NH3 to provide a compound of Formula (III):
- c) deprotecting a compound of Formula (III) to provide the compound of Formula IV:
- and
- d) purifying the compound of Formula IV.
10 more elements
Dependencies are inferred from the claim text.