Non-chromatographic purification of macrocyclic peptides by a resin catch and release

Patent metadata

Field	Value
Publication number	US-12018097-B2
Application number	US-202217943532-A
Country	US
Kind code	B2
Filing date	Sep 13, 2022
Priority date	Jun 9, 2017
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

The disclosure is directed to the synthesis and improved methods for purifying macrocyclic peptides produced by solid phase peptide synthesis. The synthesized peptide is capped with an alkyne-functionalized or azide-functionalized compound of formula (I):

prior to cleavage of the peptide from the solid phase support.

First claim

What is claimed:

1. A compound of formula (I)

wherein
X is a bond, —O—, —C(O)—, —OC(O)—, —NH—, —N(C 1-6 alkyl)-, —N(aryl)-, —NH—C(O)—, —N(C 1-6 alkyl)C(O)—, or —N(aryl)C(O)—; and
R 1 is

wherein R 2 and R 3 are each independently H, halo, C 1-6 alkyl, or OC 1-6 alkyl;
Z is C 1-6 alk or —O—C 1-6 alk-; and
Y is a bond or arylene.

2. The compound according to claim 1 that is

Assignees

• Bristol Myers Squibb Co

Inventors

• Creech Gardner S
• Kheirabadi Mahboubeh
• Eastgate Martin D
• Nirschl David S
• Carter Percy H

Classifications

• C07C309/07

  containing oxygen atoms bound to the carbon skeleton · CPC title

• C07C309/73

  to carbon atoms of non-condensed six-membered aromatic rings · CPC title

• C07K17/08

  the carrier being a synthetic polymer · CPC title

• C07K1/1077

  by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids · CPC title

• C07K1/042

  characterised by the nature of the carrier · CPC title