Amino acid derivatives

Patent metadata

Field	Value
Publication number	US-9670521-B2
Application number	US-201314430412-A
Country	US
Kind code	B2
Filing date	Sep 24, 2013
Priority date	Sep 24, 2012
Publication date	Jun 6, 2017
Grant date	Jun 6, 2017

Abstract

There are provided amino acid derivatives of formula V and VI as defined herein which are pyrrolysine analogs for use in bioconjugation processes.

First claim

The invention claimed is:

1. A pyrrolysine analog of Formula VI:

wherein
Z=NH;
FG=azide, alkene, alkyne, ketone, ester, aryl or cycloalkyne; and
b=an integer 1-4.

2. A pyrrolysine analog of formula VI according to claim 1 wherein Z is NH.

3. A pyrrolysine analog of formula VI according to claim 1 wherein b is 1 or 2.

4. A pyrrolysine analog of formula VI according to claim 1 wherein FG represents —N 3 , —CH═CH 2 , —C≡CH, —COCH 3 , COOCH 3 , phenyl substituted by halogen or cyclooctyne.

5. A pyrrolysine analog according to claim 1 selected from:

6. A mutant protein containing as non-natural amino acid one or more pyrrolysine analogs according to claim 1 .

7. An antibody which contains as non-natural amino acid one or more pyrrolysine analogs according to claim 1 in each heavy chain and/or light chain.

8. A mutant protein according to claim 6 which is conjugated via the one or more non-natural amino acids to one or more moieties selected from proteins, cytotoxic agents, drugs and polymers.

9. A mutant protein according to claim 8 which is conjugated to a PEG moiety.

10. A mutant protein according to claim 8 which is conjugated to an antibody moiety.

11. A mutant protein according to claim 8 which is conjugated to a cytotoxic agent moiety.

12. A mutant protein according to claim 8 which is conjugated to a drug moiety.

13. An antibody according to claim 7 which is conjugated via the one or more non-natural amino acids to one or more moieties selected from proteins, cytotoxic agents, drugs and polymers.

Assignees

• Medimmune Ltd

Inventors

• Grabstein Kenneth H
• Van Brunt Michael
• Marelli Marcello

Classifications

• C12P21/02 Primary

  having a known sequence of two or more amino acids, e.g. glutathione · CPC title

• C12Y301/01025

  1,4-Lactonase (3.1.1.25) · CPC title

• C07K2317/51

  Complete heavy chain or Fd fragment, i.e. VH + CH1 · CPC title

• C07K2317/24

  containing regions, domains or residues from different species, e.g. chimeric, humanized or veneered · CPC title

• C07K2317/40

  characterized by post-translational modification · CPC title