公开(公告)号：US11479581B2

公开(公告)日：2022-10-25

申请号：US16618847

申请日：2018-06-08

Applicant: BRISTOL-MYERS SQUIBB COMPANY

Inventor： Gardner S. Creech ,  Mahboubeh Kheirabadi ,  Martin D. Eastgate ,  David S. Nirschl ,  Percy H. Carter

IPC: C07K1/04 ,  C07K1/113 ,  C07K7/64 ,  C07C309/75 ,  C07C309/77 ,  C07D225/08 ,  C07K1/107 ,  C07K17/08

Abstract: The disclosure is directed to compounds and methods for preparing purified macrocyclic peptide using “catch-release” methods. These methods comprise reacting a free amino group of a resin-bound linear peptide with an azide- or alkyne-functionalized cap to form a resin-bound capped linear peptide having an azide- or alkyne-functionalized cap; cleaving the capped linear peptide from the resin to form a free capped linear peptide having an azide- or alkyne-functionalized cap; reacting the free capped linear peptide having an azide-functionalized cap with an alkyne-functionalized catch resin, or reacting the free capped linear peptide having an akynyl-functionalized cap with an azide functionalized catch resin, to form a catch-resin bound capped linear peptide; reacting the catch-resin bound capped linear peptide under conditions sufficient to effect macrocyclization of the linear peptide and release of the macrocyclic peptide from the catch resin.

公开(公告)号：US12018097B2

公开(公告)日：2024-06-25

申请号：US17943532

申请日：2022-09-13

Applicant: BRISTOL-MYERS SQUIBB COMPANY

Inventor： Gardner S. Creech ,  Mahboubeh Kheirabadi ,  Martin D. Eastgate ,  David S. Nirschl ,  Percy H Carter

IPC: C07C309/73 ,  C07C309/07 ,  C07C309/75 ,  C07C309/77 ,  C07D225/02 ,  C07D225/08 ,  C07K1/04 ,  C07K1/107 ,  C07K7/64 ,  C07K17/08

CPC classification number: C07K7/64 ,  C07C309/07 ,  C07C309/73 ,  C07C309/75 ,  C07D225/08 ,  C07K1/042 ,  C07K1/1077 ,  C07K17/08

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.