# US 10,865,215 B2 · Benzodiazepine derivatives as RSV inhibitors

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- Number: US 10,865,215 B2
- Document ID: US10865215B2
- Status: Granted
- Kind: B2
- Application number: 16/739,312
- Filed: 2020-01-10
- Published: 2020-07-16
- Granted: 2020-12-15
- Earliest claimed: 2015-07-22
- Assignees: Enanta Pharmaceuticals, Inc.
- Applicants: Enanta Pharmaceuticals, Inc.
- Inventors: Brian C. Shook; In Jong Kim; Thomas P. Blaisdell; Jianming Yu; Joseph Panarese; Yat Sun Or
- Web page: https://patentgrep.com/patent/US10865215B2

## CPC

- C07D 513/04: Ortho-condensed systems
- A61K 31/5513: 1,4-Benzodiazepines, e.g. diazepam {or clozapine}
- A61K 31/56: Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K 31/58: containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin (digitoxin {A61K31/7048})
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 31/12: Antivirals
- A61P 31/16: for influenza or rhinoviruses
- C07D 243/16: substituted in position 5 by aryl radicals
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 413/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D 471/08: Bridged systems
- C07D 491/048: the oxygen-containing ring being five-membered
- C07D 495/04: Ortho-condensed systems
- C07D 498/08: Bridged systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

## Abstract

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

## Claims

### Claim 1

A compound represented by Formula (Ib):
or a pharmaceutically acceptable salt thereof, wherein:
R1 is hydrogen or methyl;
R2 and R5 are each independently hydrogen or methyl;
A is selected from the groups below:
R3 is phenyl optionally substituted with one to three substituents selected from the group consisting of hydrogen, halo, —CF3, —OCF3, —CH3, —SO2Me, and cyano;
R4 is selected from aryl and heteroaryl; wherein R4 is optionally substituted with 1 to 3 substituents independently selected from halo, —CH3, —CF3, —OCF3, —CN, —NH2, —OH, —CH2N(CH3)2, —C(O)CH3, —NH—(C1-C6)alkyl, —NH—(C1-C6)alkyl-(C1-C6)alkoxy, —SO2—(C1-C6)alkyl, —SO2—NH—(C1-C6)alkyl, —NH—SO2—(C1-C6)alkyl, 3- to 12-membered heterocyclyl, aryl, heteroaryl, C1-C8-alkyl, C2-C8-alkenyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C1-C8-alkoxy, CH3OCH2—, CH3OCH2CH2O—,
each R6 is independently selected from halogen, methyl, CF3 and cyano;
and n is 0 to 2.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R4 is selected from the following by removal of one hydrogen atom:
wherein each of the above shown is optionally substituted.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R4 is optionally substituted by one, two or three substituents independently selected from the group consisting of: halo, —CH3, —CF3, —OCF3, —CN, —NH2, —OH, —CH2N(CH3)2, —C(O)CH3, optionally substituted —NH—(C1-C6)alkyl, optionally substituted —NH—(C1-C6)alkyl-(C1-C6)alkoxy, optionally substituted —SO2—(C1-C6)alkyl, optionally substituted —SO2—NH—(C1-C6)alkyl, optionally substituted —NH—SO2—(C1-C6)alkyl, optionally substituted 3- to 12-membered heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted —C1-C8-alkyl, optionally substituted —C1-C8-alkenyl, optionally substituted —C3-C8-cycloalkyl, optionally substituted —C3-C8-cycloalkenyl, and optionally substituted —C1-C8-alkoxy.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R4 is optionally substituted by one, two or three of the following substituents:
CH3, CN, fluoro, chloro, CH3O—, CH3C(O)—, CH3OCH2—, CH3OCH2CH2O—, —CF3, CF3O—,

### Claim 5 (depends on 1)

The compound of claim 1, represented by Formula (IVb-1), (IVb-2), (IVb-3), or (IVb-4), or a pharmaceutically acceptable salt thereof,
wherein R1, R2, and R5 are hydrogen, R3 is phenyl, R6 is fluorine or chlorine, and n is 0 or 1.

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 1)

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

### Claim 8 (depends on 1)

The compound of claim 1, wherein A is

### Claim 9 (depends on 1)

The compound of claim 1, wherein n is 0.

### Claim 10 (depends on 1)

The compound of claim 1, wherein R1, R2 and R5 are hydrogen.

### Claim 11 (depends on 1)

The compound of claim 1, wherein R3 is unsubstituted phenyl.

### Claim 12 (depends on 1)

The compound of claim 1, wherein R4 is selected from the groups below
each of which is optionally substituted.

### Claim 13 (depends on 5)

The compound of claim 5, wherein R4 is selected from the groups below