# US 2024/0189337 A1 · Nucleoside derivatives and methods of use thereof

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- Number: US 2024/0189337 A1
- Document ID: US20240189337A1
- Status: Published application
- Kind: A1
- Application number: 18/519,961
- Filed: 2023-11-27
- Published: 2024-06-13
- Earliest claimed: 2021-12-16
- Assignees: Ascletis Bioscience Co., Ltd.
- Applicants: Ascletis Bioscience Co., Ltd.
- Inventors: Bin LIANG; Bailing YANG; Yang LAI; Jinzi Jason WU
- Web page: https://patentgrep.com/patent/US20240189337A1

## CPC

- A61K 31/7084: Compounds having two nucleosides or nucleotides, e.g. nicotinamide-adenine dinucleotide, flavine-adenine dinucleotide
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 31/12: Antivirals
- A61P 31/14: for RNA viruses
- A61P 35/00: Antineoplastic agents
- C07H 19/067: with ribosyl as the saccharide radical
- C07H 21/02: with ribosyl as saccharide radical
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

Certain anti-viral compounds, pharmaceutical compositions, and methods related thereto are disclosed.

## Claims

### Claim 1

A compound of Formula I
or a pharmaceutically acceptable salt thereof,
wherein R1 or R2 is independently H, heteroaryl, —(CO)C1-C6 alkyl, —(CO)OC1-C6 alkyl, —(CO)C5-C10 aryl, —(CO)C5-C10 heteroaryl, —(CO)OC5-C10 aryl, —(CO)OC5-C10 heteroaryl, —(CO)NHC1-C6 alkyl, (CO)NHC5-C10 aryl, or (CO)NHC5-C10 heteroaryl, wherein the heteroaryl, —(CO)C1-C6 alkyl, —(CO)OC1-C6alkyl, —(CO)C5-C10 aryl, —(CO)C5-C10 heteroaryl, —(CO)OC5-C10 aryl, —(CO)OC5-C10 heteroaryl, —(CO)NHC1-C6 alkyl, (CO)NHC5-C10 aryl or (CO)NHC5-C10 heteroaryl is optionally substituted with one or more substituents each independently selected from the group consisting of halo, OH, —O—C1-C6 alkyl, NRR5, C1-C6 alkyl, C5-C10 aryl and heteroaryl,
wherein R3 or R4 is independently H, D, halo or C1-C3 alkyl, wherein alkyl is optionally substituted with one or more halo.
wherein R5 or R6 is independently H, OH, C1-C6 alkyl, —(CO)C1-C6 alkyl, —(CO)OC1-C6 alkyl, —(CO)C5-C10 aryl, —(CO)C5-C10 heteroaryl, C5-C10 aryl or C5-C10 heteroaryl,
wherein the link is independently selected from
wherein each R, and R5 is independently selected from H and C1-C6 alkyl and wherein R7 and R8 can fuse to each other to form a ring.

### Claim 2 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, having the structure of Formula II:
wherein R1 or R2 is independently H, —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, wherein the —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, is optionally substituted with one or more substituents each independently selected from the group consisting of halo, and OH.

### Claim 3 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, having the structure of Formula III:
wherein R1 is independently H, —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, wherein the —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, is optionally substituted with one or more substituents each independently selected from the group consisting of halo.

### Claim 4 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, having the structure of Formula IV:
wherein R1 or R2 is independently H, —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, wherein the —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, is optionally substituted with one or more substituents each independently selected from the group consisting of halo, and OH.

### Claim 5 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, having the structure of Formula V:
wherein R1 is independently H, —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, wherein the —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, is optionally substituted with one or more substituents each independently selected from the group consisting of halo.

### Claim 6 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, having the structure of Formula VI:
wherein R1 or R2 is independently H, —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, wherein the —(CO)C1-C6alkyl, or —(CO)C5-C10 aryl, is optionally substituted with one or more substituents each independently selected from the group consisting of halo, and OH.

### Claim 7 (depends on 6)

The compound of claim 6, or a pharmaceutically acceptable salt thereof, having the structure of Formula VII:
wherein R1 is independently H, —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, wherein the —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, is optionally substituted with one or more substituents each independently selected from the group consisting of halo.

### Claim 8 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, having the structure of Formula VII:
wherein R1 or R2 is independently H, —(CO)C1-C6 alkyl, or —(CO)C5-C1O aryl, wherein the —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, is optionally substituted with one or more substituents each independently selected from the group consisting of halo, and OH.

### Claim 9 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, having the structure of Formula IX:
wherein R1 is independently H, —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, wherein the —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, is optionally substituted with one or more substituents each independently selected from the group consisting of halo.

### Claim 10 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, having the structure of Formula X:
wherein R1 or R2 is independently H, —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, wherein the —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, is optionally substituted with one or more substituents each independently selected from the group consisting of halo, and OH.

### Claim 11 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, having the structure of Formula XI:
wherein R1 is independently H, —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, wherein the —(CO)C1-C6 alkyl, or —(CO)C5-C10 aryl, is optionally substituted with one or more substituents each independently selected from the group consisting of halo.

### Claim 12 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R3 or R4 is independently H, D, F, Cl, Br, CH3, or CF3.

### Claim 13 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R5 or R6 is independently H, OH, C1-C6 alkyl, —(CO)C1-C6 alkyl, or —(CO)OC1-C6 alkyl.

### Claim 14 (depends on 1)

A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound of claim 1.

### Claim 15 (depends on 1)

A method of treating or preventing a virus infection in a patient comprising administering to the patient an effective amount of a compound of claim 1.

### Claim 16 (depends on 15)

The method of claim 15, where the virus infection is COVID-19.

### Claim 17

A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound selected from the following: