Method for preparing multiple antigen glycopeptide carbohydrate conjugates

Patent metadata

Field	Value
Publication number	US-10899799-B2
Application number	US-201715444547-A
Country	US
Kind code	B2
Filing date	Feb 28, 2017
Priority date	Mar 17, 2011
Publication date	Jan 26, 2021
Grant date	Jan 26, 2021

Abstract

The present invention relates to a method for preparing carbohydrate T cell epitope conjugates of formula (I): M(T-B)n (I) wherein M, T, B and n ore as defined in claim 1.

First claim

The invention claimed is:

1. A method for preparing a carbohydrate T cell epitope conjugate of formula (I):

wherein
T is a peptide QYIKANSKFIGITEL (SEQ ID NO: 1); and
R 1 is:

said method comprising the step of removing the Pr protecting groups from a compound of formula (II)

wherein
R 1 is

and
the Pr groups are selected from benzyl and acetyl.

2. The method of claim 1 , wherein the Pr protecting groups are benzyl.

3. The method of claim 2 , wherein the benzyl groups are removed in the presence of TfOH or H 2 .

4. The method of claim 1 , wherein the Pr protecting groups are acetyl.

5. The method of claim 4 , wherein the acetyl groups are removed in the presence of hydrazine or MeONa.

6. A method for preparing a carbohydrate T cell epitope conjugate immobilized on a solid support, Z, via a β-Ala-residue, said T cell epitope conjugate having formula (III):

wherein
T is a peptide QYIKANSKFIGITEL (SEQ ID NO: 1);
R 1 is:

and
Pr are protecting groups, said protecting groups selected from benzyl and acetyl;
R 2 is Fmoc or H;
said method comprising the step of coupling compounds of formula (IV):

to a compound immobilized on a solid support via a β-Ala-residue, said compound immobilized on a solid support, Z, having formula (V):

wherein
T is a peptide QYIKANSKFIGITEL (SEQ ID NO: 1) and
R 1 is

7. The method of claim 6 , wherein the Pr protecting groups are benzyl.

8. The method of claim 6 , wherein the Pr protecting groups are acetyl.

9. The method of claim 7 , wherein R 2 is Fmoc.

10. The method of claim 7 , wherein R 2 is H.

11. The method of claim 8 , wherein R 2 is Fmoc.

12. The method of claim 8 , wherein R 2 is H.

13. The method of claim 6 , wherein R 2 is H.

Assignees

• Pasteur Institut
• Centre Nat Rech Scient

Inventors

• Bay Sylvie
• Leclerc Claude
• Lo-Man Richard

Classifications

• C07K9/001 Primary

  the peptide sequence having less than 12 amino acids and not being part of a ring structure · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61K47/645

  Polycationic or polyanionic oligopeptides, polypeptides or polyamino acids, e.g. polylysine, polyarginine, polyglutamic acid or peptide TAT · CPC title

• A61K47/55

  the modifying agent being also a pharmacologically or therapeutically active agent, i.e. the entire conjugate being a codrug · CPC title

• A61K40/00

  Cellular immunotherapy (medicinal preparations containing antigens or antibodies A61K39/00) · CPC title