# US 12,006,326 B2 · Antiviral heterocyclic compounds

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- Number: US 12,006,326 B2
- Document ID: US12006326B2
- Status: Granted
- Kind: B2
- Application number: 17/894,412
- Filed: 2022-08-24
- Published: 2023-04-27
- Granted: 2024-06-11
- Earliest claimed: 2019-10-04
- Assignees: Enanta Pharmaceuticals, Inc.
- Applicants: Enanta Pharmaceuticals, Inc.
- Inventors: Adam Szymaniak; Kevin McGrath; Jianming Yu; Tyler Mann; Long Nguyen; Kaicheng Zhu; In Jong Kim; Yat Sun Or
- Web page: https://patentgrep.com/patent/US12006326B2

## CPC

- C07D 491/052: the oxygen-containing ring being six-membered
- C07D 471/04: Ortho-condensed systems
- C07D 491/044: with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D 491/048: the oxygen-containing ring being five-membered
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: which inhibit Human Respiratory Syncytial Virus (HRSV) or Human Metapneumovirus (HMPV) inhibitors. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HRSV or HMPV infection. The invention also relates to methods of treating an HRSV or HMPV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

## Claims

### Claim 1

A compound represented by Formula (I):
or a pharmaceutically acceptable salt thereof, wherein:
A is selected from the group consisting of:
1) optionally substituted aryl; and
2) optionally substituted heteroaryl;
B is O;
R1 and R2 are each hydrogen;
Z is hydrogen;
W is
optionally substituted —C1-C6 alkyl;
G is
—C(O)NR11R12;
n is 1;
Y is O;
E is optionally substituted aryl;
R3 is hydroxy or fluorine;
R4 is selected from the group consisting of
optionally substituted —C1-C6 alkyl and
optionally substituted —C3-C8 cycloalkyl;
R11 at each occurrence is independently selected from the group consisting of:
1) hydrogen;
2) optionally substituted —C1-C8-alkyl;
3) optionally substituted —C3-C8-cycloalkyl;
4) optionally substituted 3- to 8-membered heterocyclic;
5) optionally substituted aryl;
6) optionally substituted arylalkyl;
7) optionally substituted heteroaryl; and
8) optionally substituted heteroarylalkyl; and
R12 at each occurrence is independently selected from the group consisting of:
1) hydrogen;
2) optionally substituted —C1-C8-alkyl;
3) optionally substituted —C3-C8-cycloalkyl;
4) optionally substituted 3- to 8-membered heterocyclic;
5) optionally substituted aryl;
6) optionally substituted arylalkyl;
7) optionally substituted heteroaryl; and
8) optionally substituted heteroarylalkyl;
alternatively, R11 and R12 are taken together with the nitrogen atom to which they are attached to form a 3- to 12-membered heterocyclic ring.

### Claim 2 (depends on 1)

The compound of claim 1, wherein G is —C(O)NH2.

### Claim 3 (depends on 1)

The compound of claim 1, wherein E is selected from the groups set forth below:

### Claim 4 (depends on 1)

The compound of claim 1, wherein A is selected from the groups set forth below by removal of a hydrogen atom:
wherein each of these groups is optionally substituted.

### Claim 5 (depends on 1)

The compound of claim 1, represented by Formula (IXa), or a pharmaceutically acceptable salt thereof:
wherein R21 is optionally substituted methyl, halo, CN, OR11, or NR11R12; m is 0, 1, 2, 3, 4 or 5; and A, W, R3, R4, R11, and R12 are as defined in claim 1.

### Claim 6 (depends on 1)

The compound of claim 1, represented by Formula (X-1), or a pharmaceutically acceptable salt thereof:
wherein R21 is optionally substituted methyl, halo, CN, OR11, or NR11R12; m′ is 0, 1 or 2; and A, W, R11, and R12 are as defined in claim 1.

### Claim 7 (depends on 1)

The compound of claim 1, represented by Formula (X-1a), or a pharmaceutically acceptable salt thereof:
wherein R21 is optionally substituted methyl, halo, CN, OR11, or NR11R12; m′ is 0, 1 or 2; and A, W, R11, and R12 are as defined in claim 1.

### Claim 8 (depends on 1)

A pharmaceutical composition comprising a compound according to claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, diluent or excipient.

### Claim 9 (depends on 1)

A method of treating an RSV infection in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound of claim 1.

### Claim 10 (depends on 9)

The method of claim 9, further comprising the step of administering to the subject an anti-RSV agent.

### Claim 11 (depends on 9)

The method of claim 9, further comprising administering to the subject a steroid anti-inflammatory compound.

### Claim 12 (depends on 1)

A method of treating RSV and influenza in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound of claim 1 and a therapeutically effective amount of an anti-influenza agent.

### Claim 13 (depends on 10)

The method of claim 10, wherein the compound and the anti-RSV agent are co-formulated.

### Claim 14 (depends on 10)

The method of claim 10, wherein the compound and the anti-RSV agent are co-administered.

### Claim 15 (depends on 10)

The method of claim 10, wherein administering the compound allows for administering of the anti-RSV agent at a lower dose or frequency as compared to the administering of the anti-RSV agent alone that is required to achieve similar results in prophylactically treating an RSV infection in a subject in need thereof.

### Claim 16 (depends on 1)

A method of treating an HMPV infection in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound or a combination of compounds of claim 1.

### Claim 17 (depends on 16)

The method of claim 16, further comprising the step of administering to the subject an anti-HMPV agent.

### Claim 18 (depends on 17)

The method of claim 17, wherein the compound and the anti-HMPV agent are co-formulated.