Modified amino acids comprising tetrazine functional groups, methods of preparation, and methods of their use

Patent metadata

Field	Value
Publication number	US-9840493-B2
Application number	US-201415028005-A
Country	US
Kind code	B2
Filing date	Oct 10, 2014
Priority date	Oct 11, 2013
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

Provided herein are modified amino acids comprising a tetrazine groups according to Formula I: polypeptides, antibodies, payloads and conjugates comprising these modified amino acid residues derived from the modified amino acids, and methods of producing the polypeptides, antibodies, payloads and conjugates comprising the modified amino acid residues. The polypeptides, antibodies, payloads and conjugates are useful in methods of treatment and prevention, methods of detection and methods of diagnosis.

First claim

What is claimed is:

1. A compound according to formula I:

or a salt thereof, wherein:
Ar is

V is a single bond, lower alkylene, or —W 1 —W 2 —;
one of W 1 and W 2 is absent or lower alkylene, and the other is —NH—, —O—, or —S—;
X 1 is —NH—, —O—, or —S—;
one of Z 1 , Z 2 , and Z 3 is —N— and the others of Z 1 , Z 2 , and Z 3 are each independently —CH—; and
R is lower alkyl.

2. The compound of claim 1 , wherein V is a single bond, —NH—, or —CH 2 NH—.

3. The compound of claim 1 , wherein:
V is a single bond, —NH—, or —CH 2 NH—; and
Ar is

4. The compound of claim 1 , wherein:
V is a single bond, —NH—, or —CH 2 NH—; and
Ar is

5. The compound of claim 1 , wherein:
V is a single bond, —NH—, or —CH 2 NH—; and
Ar is

6. The compound of claim 1 according to formula Ia:

7. The compound of claim 1 according to formula IV, V, VI or VII:

or a salt thereof, wherein V is a single bond, —NH—, or —CH 2 NH—.

8. The compound of claim 1 according to formula VIII or IX:

or a salt thereof, wherein V is a single bond, —NH—, or —CH 2 NH—.

9. The compound of claim 1 according to any one of formulas 2, 3, and 6-10:

or a salt thereof.

Assignees

• Sutro Biopharma Inc

Inventors

• Yang Wenjin
• Yin Qun

Classifications

• A61K47/6849

  the antibody targeting a receptor, a cell surface antigen or a cell surface determinant · CPC title

• A61K47/6871

  the antibody targeting an enzyme · CPC title

• C07K16/40

  against enzymes · CPC title

• C07D401/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C12P21/02

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