Granted Patent B2

US 11,046,695 · App. 15/775,319 · Granted Jun 29, 2021

Inventors: Manuel Perez Vazquez (Milton, CA); M. Monzur Morshed (Mississauga, CA); Jennifer L. Hickey (Toronto, CA); Marc-André Poupart (Laval, CA); Gaoqiang Yang (Montreal, CA); James Gillard (Rosemere, CA); Adam Paul Kafal (Toronto, CA); Andrew L. Roughton (Port Hope, CA)

Assignees: Zealand Pharma A/S; Universite de Montreal

C07D487/04A61P1/04C07C271/18C07C271/22C07D207/16C07K1/1075C07K7/06C07K7/54C07K7/56C07K7/64A61K9/0014A61K9/0053A61K38/00C07C2603/18

Abstract

Claims (18)

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:

Assignments (6)