The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Aug. 10, 2021
Filed:
Oct. 30, 2019
Triad National Security, Llc, Los Alamos, NM (US);
Robert F. Williams, Los Alamos, NM (US);
Paul William Peterson, Los Alamos, NM (US);
Robert David Gilbertson, Los Alamos, NM (US);
Jurgen G. Schmidt, Los Alamos, NM (US);
Charlie E. Strauss, Los Alamos, NM (US);
Triad National Security, LLC, Los Alamos, NM (US);
Abstract
The present disclosure provides improved methods for controlled cyclization of peptoid dimers to form N,N'-2,5-diketopiperazines (N,N′-2,5-DKPs) with significant selectivity. In at least some examples, selectivity is based on a serendipitous conglomeration of slow exchange of amide rotamers, steric repulsion from the degree of α-substitution, and the geometric bulk of an amine nucleophile. By varying reaction conditions, the selectivity of the reaction and formation of a particular N,N′-2,5-DKP can be switched. The cyclization works in the presence of a variety of protection groups and diverse functionalities. The teachings herein provide techniques for synthesizing N,N′-2,5-DKPs that can be readily docked with drug candidates for shuttling across the blood brain barrier. This method provides a facile way to produce substituted DKPs containing groups ready for post-modification to include docking drug candidates.