# US 11,999,696 B2 · Heterocyclic azide units and their use in polymer coatings

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- Number: US 11,999,696 B2
- Document ID: US11999696B2
- Status: Granted
- Kind: B2
- Application number: 17/257,270
- Filed: 2019-12-09
- Published: 2021-09-16
- Granted: 2024-06-04
- Earliest claimed: 2018-12-18
- Assignees: Illumina Cambridge Limited
- Applicants: Illumina Cambridge Limited
- Inventors: Wayne N. George; Xiaolin Wu; Andrew A. Brown; Donald Wellings
- Web page: https://patentgrep.com/patent/US11999696B2

## CPC

- C07D 213/75: Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 207/16: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 213/82: in position 3
- C08F 8/48: Isomerisation; Cyclisation
- C08F 220/56: Acrylamide; Methacrylamide
- C08F 2810/50: wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## 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.

## Claims

### Claim 1

A compound of formula (I)
wherein
R1 is H or C1-4 alkyl;
R2 is H or C1-4 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 R3 is H or C1-4 alkyl; and
Z is a nitrogen containing heterocycle.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein E is optionally substituted C1-4 alkylene.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein the compound is of formula (Ia)
wherein p is 1, 2, 3 or 4.

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 4)

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

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 1)

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

### Claim 8 (depends on 1)

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

### Claim 9 (depends on 1)

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.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein the compound is of formula (Ic)
wherein p is 1, 2, 3 or 4.

### Claim 11 (depends on 1)

The compound according to claim 1, wherein the compound is of formula (Id)
wherein p is 1, 2, 3 or 4.

### Claim 12 (depends on 1)

The compound according to claim 1, wherein the compound is of formula (Ie)
wherein p is 1, 2, 3 or 4.

### Claim 13 (depends on 1)

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

### Claim 14 (depends on 1)

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

### Claim 15 (depends on 1)

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

### Claim 16 (depends on 1)

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

### Claim 17 (depends on 1)

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.

### Claim 18 (depends on 17)

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.

### Claim 19

A copolymer comprising a recurring monomer unit of formula (II):
wherein
R1 is H or C1-4 alkyl;
R2 is H or C1-4 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 R3 is H or C1-4 alkyl; and
Z is a nitrogen containing heterocycle; and
at least one other recurring monomer unit.

### Claim 20 (depends on 19)

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.