Fragment synthesis of substituted cyclic peptides

Patent metadata

Field	Value
Publication number	US-11046695-B2
Application number	US-201615775319-A
Country	US
Kind code	B2
Filing date	Nov 14, 2016
Priority date	Nov 11, 2015
Publication date	Jun 29, 2021
Grant date	Jun 29, 2021

Abstract

There is described herein use of a compound of formula (I) below to make cyclic peptides.

First claim

The invention claimed is:

1. A process for preparing a cyclic peptide of formula (II):

wherein:
—C(O)-L-Z— is selected from the group consisting of:

comprising the following steps:
(i) cyclizing head-to-tail a linear peptide of formula (IIa):

wherein:
R d is tert-butyloxycarbonyl or 9-fluorenylmethoxycarbonyl; and
—C(O)-L-Z′ is selected from the group consisting of:

in the presence of 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one, to provide a cyclic peptide of formula (IIb):

wherein:
R d is tert-butyloxycarbonyl or 9-fluorenylmethoxycarbonyl; and
—C(O)-L-Z— is selected from the group consisting of:

(ii) deprotecting the cyclic peptide of formula (IIb) above in the presence of piperidine and N-methyl-2-pyrrolidone, to provide the cyclic peptide of formula (II) above.

2. The process of claim 1 , wherein —C(O)-L-Z— is:

3. The process of claim 1 , wherein —C(O)-L-Z— is:

4. The process of claim 1 , wherein —C(O)-L-Z— is:

5. The process of claim 1 , wherein —C(O)-L-Z— is:

6. The process of claim 1 , wherein —C(O)-L-Z— is:

Assignees

• Zealand Pharma As
• Univ Montreal

Inventors

• Vazquez Manuel Perez
• Morshed M Monzur
• Hickey Jennifer L
• Poupart Marc-André
• Yang Gaoqiang
• Gillard James
• Kafal Adam Paul
• Roughton Andrew L

Classifications

• Y02P20/55

  Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups · CPC title

• A61P1/00

  Drugs for disorders of the alimentary tract or the digestive system · CPC title

• A61P1/18

  for pancreatic disorders, e.g. pancreatic enzymes · CPC title

• C07K1/1075

  by covalent attachment of amino acids or peptide residues · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title