# US 2019/0105334 A1 · Anti-Viral Azide Containing Compounds

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2019/0105334 A1
- Document ID: US20190105334A1
- Status: Published application
- Kind: A1
- Application number: 16/208,251
- Filed: 2018-12-03
- Published: 2019-04-11
- Earliest claimed: 2010-07-28
- Assignees: Life Technologies Corporation
- Applicants: Life Technologies Corporation
- Inventors: Brian Agnew; Upinder Singh; Scott Grecian
- Web page: https://patentgrep.com/patent/US20190105334A1

## CPC

- A61K 31/655: Azo (—N=N—), diazo (=N2), azoxy (>N—O—N< or N(=O)—N<), azido (—N3) or diazoamino (—N=N—N<) compounds
- A61K 31/7008: Compounds having an amino group directly attached to a carbon atom of the saccharide radical, e.g. D-galactosamine, ranimustine
- C12N 7/00: Viruses; Bacteriophages; Compositions thereof; Preparation or purification thereof (preparing medicinal viral antigen or antibody compositions, e.g. virus vaccines, A61K39/00)
- C12N 2710/14151: Methods of production or purification of viral material
- C12N 2710/14163: by chemical treatment
- C12N 2740/16051: Methods of production or purification of viral material
- C12N 2740/16063: by chemical treatment
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)

## Abstract

Methods of using azide-modified biomolecules, such as fatty acids, carbohydrates and lipids, to treat a plant, an insect or an animal infected with a virus or to inhibit infectivity of a virus, such as the human immunodeficiency virus, are provided. Also provided are methods of labeling a virus, such as human immunodeficiency virus, with an azide-modified biomolecule, such as a fatty acid, a carbohydrate, or an isoprenoid lipid. Also, provided are methods of tracking a virus in vivo, with an azide-modified biomolecule, such as a fatty acid, a carbohydrate, or an isoprenoid lipid. The azide-modified biomolecules may be combined with a pharmaceutically acceptable excipient to produce a pharmaceutical composition, optionally containing another anti-viral agent and/or a delivery agent, such as a liposome.

## Claims

### Claim 1

A method of producing a virus labeled with an azide-modified fatty acid, an azide-modified carbohydrate, an azide-modified isoprenoid lipid, or a pharmaceutically acceptable salt thereof, the method comprising contacting a cell infected with the virus with the azide-modified fatty acid, the azide-modified carbohydrate, the azide-modified isoprenoid lipid, or pharmaceutically acceptable salt thereof so that the azide-modified fatty acid, the azide-modified carbohydrate, the azide-modified isoprenoid lipid, or pharmaceutically acceptable salt thereof enters the cell and is incorporated into a protein of the virus, thereby producing the labeled virus.

### Claim 2 (depends on 1)

The method of claim 1, wherein the azide-modified fatty acid or pharmaceutically acceptable salt thereof, has the formula:
Y—CH2—X—CO2H
wherein,
Y is H or an azido group; and
when Y is an azido group, X is a linear or branched carbon chain comprising 6 to 28 carbons, wherein one or more of said carbons may be independently replaced by an oxygen, selenium, silicon, sulfur, SO, SO2 or NR1, or wherein one or more pairs of said carbons adjacent to one another may be attached to one another by a double or triple bond; or
when Y is H, X is a linear or branched carbon chain comprising 6 to 28 carbons, wherein one hydrogen on one of said carbons is replaced with an azido group and wherein one or more of said carbons not having an the azido group attached thereto may be independently replaced by an oxygen, selenium, silicon, sulfur, SO, SO2 or NR1, or wherein one or more pairs of said carbons adjacent to one another and not having an azido group may be attached to one another by a double or triple bond;
wherein, R1 is H or an alkyl comprising 1 to 6 carbons.

### Claim 3 (depends on 2)

The method of claim 2, wherein Y is an azido group.

### Claim 4 (depends on 3)

The method of claim 3, wherein X is a linear carbon chain.

### Claim 5 (depends on 4)

The method of claim 4, wherein the carbon chain comprises 8 to 15 carbons.

### Claim 6 (depends on 5)

The method of claim 5, wherein the carbon chain does not contain an oxygen, selenium, silicon, sulfur, SO, SO2 or NR1.

### Claim 7 (depends on 6)

The method of claim 6, wherein the carbon chain does not contain a double or triple bond.

### Claim 8 (depends on 7)

The method of claim 7, wherein the azide-modified fatty acid is 15-azidopentadecanoic acid or pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 7)

The method of claim 7, wherein the azide-modified fatty acid is 12-azidododecanoic acid or pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 1)

The method of claim 1, wherein the cell is a human cell.

### Claim 11 (depends on 1)

The method of claim 1, wherein the virus is a human immunodeficiency virus.

### Claim 12 (depends on 1)

The method of claim 1, wherein the cell is an insect cell.

### Claim 13 (depends on 1)

The method of claim 1, wherein the virus is a baculovirus.

### Claim 14 (depends on 1)

The method of claim 1, wherein the azide-modified carbohydrate, azide-modified fatty acid, azide-modified isoprenoid lipid, or pharmaceutically acceptable salt is formulated with a pharmaceutically acceptable excipient.

### Claim 15 (depends on 14)

The method of claim 14, further comprising the step of administering to the cell the azide-modified carbohydrate, azide-modified fatty acid, azide-modified isoprenoid lipid, or pharmaceutically acceptable salt which is formulated with a pharmaceutically acceptable excipient.

### Claim 16

A method of tracking a virus in vivo comprising the steps of
contacting cultured cells or a subject with an azide-modified carbohydrate, azide-modified fatty acid, azide-modified isoprenoid lipid, or a pharmaceutically acceptable salt thereof;
contacting the cultured cells or the subject with an alkyne labeled reporter molecule; and
tracking the reporter-labeled virus in the cultured cells or the subject.

### Claim 17 (depends on 16)

The method of claim 16, wherein the cultured cells or the subject is contacted with an azide-modified fatty acid or pharmaceutically acceptable salt thereof.

### Claim 18 (depends on 17)

The method of claim 17, wherein the azide-modified fatty acid or pharmaceutically acceptable salt thereof, has the formula:
Y—CH2—X—CO2H
wherein,
Y is H or an azido group; and
when Y is an azido group, X is a linear or branched carbon chain comprising 6 to 28 carbons, wherein one or more of said carbons may be independently replaced by an oxygen, selenium, silicon, sulfur, SO, SO2 or NR1, or wherein one or more pairs of said carbons adjacent to one another may be attached to one another by a double or triple bond; or
when Y is H, X is a linear or branched carbon chain comprising 6 to 28 carbons, wherein one hydrogen on one of said carbons is replaced with an azido group and wherein one or more of said carbons not having an the azido group attached thereto may be independently replaced by an oxygen, selenium, silicon, sulfur, SO, SO2 or NR1, or wherein one or more pairs of said carbons adjacent to one another and not having an azido group may be attached to one another by a double or triple bond;
wherein, R1 is H or an alkyl comprising 1 to 6 carbons.

### Claim 19 (depends on 18)

The method of claim 18, wherein Y is an azido group.

### Claim 20 (depends on 19)

The method of claim 19, wherein X is a linear carbon chain.

### Claim 21 (depends on 20)

The method of claim 20, wherein the carbon chain comprises 8 to 15 carbons.

### Claim 22 (depends on 21)

The method of claim 21, wherein the carbon chain does not contain an oxygen, selenium, silicon, sulfur, SO, SO2 or NR1.

### Claim 23 (depends on 22)

The method of claim 22, wherein the carbon chain does not contain a double or triple bond.

### Claim 24 (depends on 23)

The method of claim 23, wherein the azide-modified fatty acid is 15-azidopentadecanoic acid or pharmaceutically acceptable salt thereof.

### Claim 25 (depends on 23)

The method of claim 23, wherein the azide-modified fatty acid is 12-azidododecanoic acid or pharmaceutically acceptable salt thereof.