# US 10,501,476 B2 · Thieno[3,2-d]pyrimidine, furo[3,2-d]pyrimidine, and pyrrolo[3,2-D]pyrimidines useful for treating respiratory syncitial virus infections

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- Number: US 10,501,476 B2
- Document ID: US10501476B2
- Status: Granted
- Kind: B2
- Application number: 16/203,112
- Filed: 2018-11-28
- Published: 2019-06-27
- Granted: 2019-12-10
- Earliest claimed: 2014-07-28
- Assignees: Gilead Sciences, Inc.
- Applicants: Gilead Sciences, Inc.
- Inventors: Michael O'Neil Hanrahan Clarke; Richard L. Mackman; Dustin Siegel
- Web page: https://patentgrep.com/patent/US10501476B2

## CPC

- C07D 495/04: Ortho-condensed systems
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 31/12: Antivirals
- A61P 31/14: for RNA viruses
- A61P 31/16: for influenza or rhinoviruses
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07F 9/6561: containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07H 7/06: Heterocyclic radicals
- C07H 11/04: Phosphates; Phosphites; Polyphosphates
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- 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

Provided herein are formulations, methods and substituted thieno[3,2-d]pyrimidine, furo[3,2-d]pyrimidine, and pyrrolo[3,2-d]pyrimidine compounds of Formula (I) for treating Pneumovirinae virus infections, including respiratory syncytial virus infections, as well as methods and intermediates for synthesis of substituted thieno[3,2-d]pyrimidine, furo[3,2-d]pyrimidine, and pyrrolo[3,2-d]pyrimidine compounds.

## Claims

### Claim 1

A compound of Formula (II):
or a pharmaceutically acceptable salt thereof, wherein
R1 is selected from the group consisting of H, CH3, F, Cl, and NH2;
R2 is selected from the group consisting of F, Cl, OH, NH2, CN, and N3;
R3 is selected from the group consisting of CN, N3, methyl, ethyl, propyl, vinyl, propenyl, ethynyl, CH2F, CHF2, CH2Cl, CH2SMe, and CH2OMe; and
R4 is selected from the group consisting of H,
wherein
R8 is phenyl;
R9 is H or CH3;
R10 is H or C1-C6 alkyl; and
R11 is H or C1-C8 alkyl.

### Claim 2 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R1 is Cl.

### Claim 3 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R1 is NH2.

### Claim 4 (depends on 1)

The compound of claim 1, or the pharmaceutical acceptable salt thereof, wherein R4 is H.

### Claim 5 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R1 is H.

### Claim 6 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R1 is F.

### Claim 7 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R2 is F.

### Claim 8 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R2 is Cl.

### Claim 9 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R2 is N3.

### Claim 10 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R3 is selected from the group consisting of CN and N3.

### Claim 11 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R3 is selected from the group consisting of methyl, ethyl, and propyl.

### Claim 12 (depends on 1)

The compound of claim 1, or the acceptable salt thereof, wherein R3 is selected from the group consisting of CH2F, CHF2, and CH2Cl.

### Claim 13 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R4 is selected from the group consisting of:

### Claim 14 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R4 is:

### Claim 15 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R4 is:

### Claim 16 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R4 is:

### Claim 17 (depends on 1)

The compound of claim 1, or the pharmaceutically acceptable salt thereof, wherein R4 is:

### Claim 18 (depends on 1)

A method of treating a Pneumoviridae virus infection in a human in need thereof, the method comprising administering to the human a therapeutically effective amount of the compound of claim 1, or the pharmaceutically acceptable salt thereof.

### Claim 19 (depends on 18)

The method of claim 18, wherein the Pneumoviridae virus infection is a respiratory syncytial virus infection.

### Claim 20 (depends on 1)

A pharmaceutical composition comprising (i) the compound of claim 1, or the pharmaceutically acceptable salt thereof, and (ii) a pharmaceutically acceptable carrier or excipient.