Heterocyclic azide units and their use in polymer coatings

Patent metadata

Field	Value
Publication number	US-11999696-B2
Application number	US-201917257270-A
Country	US
Kind code	B2
Filing date	Dec 9, 2019
Priority date	Dec 18, 2018
Publication date	Jun 4, 2024
Grant date	Jun 4, 2024

Abstract

Described herein are heterocyclic azide-containing monomer units, copolymers comprising such heterocyclic azide-containing monomer units, substrate-bound copolymers, and oligonucleotide-bound copolymers, methods for making such copolymers and reacting them with a substrate and/or oligonucleotide, and methods of using such copolymers for immobilization of oligonucleotides to a substrate, for example for use in DNA sequencing or other diagnostic applications.

First claim

What is claimed is:

1. A compound of formula (I)

wherein
R 1 is H or C 1-4 alkyl;
R 2 is H or C 1-4 alkyl;
L is a linker comprising a linear chain having 2 to 20 atoms selected from the group consisting of carbon, oxygen, and nitrogen and optional substituents on the carbon and any nitrogen atoms in the chain;
E is a linear chain having 1 to 4 atoms selected from the group consisting of carbon, oxygen and nitrogen, and optional substituents on the carbon and any nitrogen atoms in the chain;
A is an N substituted amide having formula

 wherein R 3 is H or C 1-4 alkyl; and
Z is a nitrogen containing heterocycle.

2. The compound according to claim 1 , wherein E is optionally substituted C 1-4 alkylene.

3. The compound according to claim 1 , wherein the compound is of formula (Ia)

wherein p is 1, 2, 3 or 4.

4. The compound according to claim 1 , wherein the nitrogen containing heterocycle comprises a 6 membered ring.

5. The compound according to claim 4 , wherein A and E are bonded at positions 2 and 5 of the 6 membered ring.

6. The compound according to claim 1 , wherein the nitrogen containing heterocycle comprises a 5 membered ring.

7. The compound according to claim 1 , wherein the nitrogen containing heterocycle is aromatic.

8. The compound according to claim 1 , wherein the nitrogen containing heterocycle is saturated.

9. The compound according to claim 1 , wherein the compound is of formula (Ib)

wherein X is CH or N; and
wherein p is 1, 2, 3 or 4.

10. The compound according to claim 1 , wherein the compound is of formula (Ic)

wherein p is 1, 2, 3 or 4.

11. The compound according to claim 1 , wherein the compound is of formula (Id)

wherein p is 1, 2, 3 or 4.

12. The compound according to claim 1 , wherein the compound is of formula (Ie)

wherein p is 1, 2, 3 or 4.

13. The compound according to claim 1 , wherein the compound is of formula (If)

14. The compound according to claim 1 , wherein the compound is of formula (Ig)

15. The compound according to claim 1 , wherein the compound is of formula (Ih)

16. The compound according to claim 1 , wherein the compound is of formula (Ij)

17. The compound according to claim 1 , wherein the compound of formula (Ik):

wherein X is CH or N; and
wherein p is 1, 2, 3 or 4.

18. The compound according to claim 17 , wherein the compound of Formula (Ik) is a compound of Formula (Im):

wherein n is an integer from 2 to 20; and
wherein p is 1, 2, 3 or 4.

19. A copolymer comprising a recurring monomer unit of formula (II):

wherein
R 1 is H or C 1-4 alkyl;
R 2 is H or C 1-4 alkyl;
L is a linker comprising a linear chain having 2 to 20 atoms selected from the group consisting of carbon, oxygen, and nitrogen and optional substituents on the carbon and any nitrogen atoms in the chain;
E is a linear chain having 1 to 4 atoms selected from the group consisting of carbon, oxygen and nitrogen, and optional substituents on the carbon and any nitrogen atoms in the chain;
A is an N substituted amide having formula

 wherein R 3 is H or C 1-4 alkyl; and
Z is a nitrogen containing heterocycle; and
at least one other recurring monomer unit.

20. The copolymer according to claim 19 , wherein the recurring monomer unit of formula (II) is a recurring monomer unit of formula (IIa)

where p is 1, 2, 3, or 4.

Assignees

• Illumina Cambridge Ltd

Inventors

• George Wayne N
• Wu Xiaolin
• Brown Andrew A
• Wellings Donald

Classifications

• C07D213/75 Primary

  Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates · CPC title

• C07D207/16

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07D213/82

  in position 3 · CPC title

• C08F220/56

  Acrylamide; Methacrylamide · CPC title

• C08F2810/50

  wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority · CPC title