SDP-containing heterobifunctional agents

Patent metadata

Field	Value
Publication number	US-9440925-B2
Application number	US-201514810766-A
Country	US
Kind code	B2
Filing date	Jul 28, 2015
Priority date	Mar 25, 2011
Publication date	Sep 13, 2016
Grant date	Sep 13, 2016

Abstract

The present disclosure is directed to a reactive ester agent for conjugating a click-reactive group to a carrier molecule or solid support. The reactive ester agent has the general formula IA, wherein the variables R 1 , R 2 , R 3 , R a and L are described throughout the application.

First claim

The invention claimed is:

1. A method of making a compound of Formula IA or a salt thereof:

said method comprising:
contacting a compound of Formula IB or a salt thereof:

with a compound of Formula IC or a tautomer or salt thereof:

wherein
R 1 is a halogen,
R 2 is a halogen,
R 3 comprises a water solubilizing group,
L is a linker, and
R a is a click-reactive group.

2. A kit for click-labeling a carrier molecule or solid support, wherein said kit comprises:
a) a compound of Formula IA or a salt thereof:

wherein
L is a linker,
R 1 is a halogen,
R 2 is a halogen,
R 3 comprises a water solubilizing group, and
R a is a click-reactive group; and
b) instructions for click-labeling the carrier molecule or solid support.

3. The kit of claim 2 , wherein R a is an alkyne reactive moiety, an azide reactive moiety, a diene, a dienophile, an epoxide, or an aziridine compound.

4. The kit of claim 2 , where the click-reactivity of R a is copper-catalyzed.

5. The kit of claim 2 , where the click-reactivity of R a is not copper-catalyzed.

6. The kit of claim 2 , wherein L is a covalent bond, -alkyl-, -substituted alkyl-, -alkenyl-, -substituted alkenyl-, -heterocyclyl-, -substituted heterocyclyl-, -aryl-, -substituted aryl-, -heteroaryl-, -substituted heteroaryl-, -cycloalkyl-, -substituted cycloalkyl-, -oxy-, -alkoxy-, -substituted alkoxy-, -alkoxyalkyl-, poly(alkoxyalkyl)-, PEG, -thio-, -amino-, or -substituted amino-.

7. The kit of claim 2 , wherein R 1 and R 2 are chloro.

8. The kit of claim 2 , wherein R 3 is —COO, —SO 3 , substituted azenyl, PEG, phosphate, or bisphosphonate.

9. The kit of claim 7 , wherein R 3 is —SO 3 .

10. The kit of claim 2 , wherein the compound of Formula IA is a salt.

11. The kit of claim 10 , wherein the salt comprises a potassium ion, a sodium ion, or a triethylammonium ion.

12. The kit of claim 2 , wherein R a is an alkyne reactive moiety or an azide reactive moiety.

13. The kit of claim 9 , wherein R a is an alkyne reactive moiety or an azide reactive moiety.

14. The kit of claim 13 , where the compound has the formula comprising:

15. The kit of claim 13 , where the compound has the formula comprising:

16. The kit of claim 13 , where the compound has the formula comprising:

wherein A is a substituted or unsubstituted cyclooctyne ring that may contain a heteroatom and/or be fused to one or more 5- or 6-membered aromatic or heteroaromatic rings.

17. The kit of claim 14 , wherein the compound is

Assignees

• Life Technologies Corp

Inventors

• Gee Kyle
• Chen Aimei
• Kang Hee Chol

Classifications

• C07D225/08 Primary

  condensed with two six-membered rings · CPC title

• C07D225/02

  not condensed with other rings · CPC title

• C07D223/08

  Oxygen atoms · CPC title

• C07K16/18

  against material from animals or humans · CPC title

• G01N33/532

  Production of labelled immunochemicals · CPC title