# US 5,350,772 A · Certain substituted phenoxy-methyl phenyl-methoxy benzenes having antiviral activity

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- Number: US 5,350,772 A
- Document ID: US5350772A
- Status: Granted
- Kind: A
- Application number: 08/039,532
- Filed: 1993-03-26
- Granted: 1994-09-27
- Earliest claimed: 1991-06-19
- Assignees: Schering Corporation
- Inventors: Viyyoor M. Girijavallabhan; Ashit K. Ganguly; Richard W. Versace
- Web page: https://patentgrep.com/patent/US5350772A

## CPC

- C07D 213/30: Oxygen atoms
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- C07C 43/225: containing halogen
- C07C 43/23: containing hydroxy or O-metal groups
- C07C 69/92: with etherified hydroxyl groups
- C07D 263/14: with radicals substituted by oxygen atoms
- C07D 307/12: Radicals substituted by oxygen atoms
- C07D 307/28: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 307/42: Singly bound oxygen atoms
- C07D 333/16: by oxygen atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A compound represented by formula I Ar.sub.1 --O--M--O--Ar.sub.2 I wherein Ar.sub.1 and Ar.sub.2 are independently substituted phenyl or substituted pyridinyl, the substituents on said phenyl or pyridinyl being independently selected from one, two or three of (C.sub.1 -C.sub.10) alkyl, (C.sub.1 -C.sub.10) alkoxy, halogen, carbamyl, (C.sub.1 -C.sub.10) alkoxycarbonyl, oxazoyl, and (C.sub.1 -C.sub.10) alkyl substituted by halogen, (C.sub.1 -C.sub.10) alkoxy, hydroxy, or (C.sub.1 -C.sub.10) alkoxycarbonyl; M is ##STR1## (C.sub.4 -C.sub.8) alkylene, (C.sub.4 -C.sub.8) alkenylene or (C.sub.4 -C.sub.8)-alkynylene; O is oxygen; or pharmaceutically acceptable salts thereof. as well as pharmaceutical compositions containing the compounds and methods of treating or preventing viral infections, especially picornaviral infections, are disclosed.

## Claims

### Claim 1

A compound represented by formula II
Ar.sub.1a --O--M--O--Ar.sub.1b II
wherein each of Ar.sub.1a and Ar.sub.1b is independently selected from phenyl substituted by two or three of (C.sub.1 -C.sub.10) alkyl, (C.sub.1 -C.sub.10)alkoxy and halogen M is ##STR31## and O is oxygen.

### Claim 2 (depends on 1)

A compound of claim 1 wherein one of Ar.sub.1a and Ar.sub.1b is 2-halo-4-(C.sub.1 -C.sub.10)alkoxy.

### Claim 3 (depends on 1)

A compound of claim 1 wherein Ar.sub.1a =Ar.sub.1b =2-halo-4-(C.sub.1 -C.sub.10) alkoxy.

### Claim 4 (depends on 1)

A compound of claim 1 wherein one of Ar.sub.1b and Ar.sub.1a is 2-halo-4-(C.sub.1 -C.sub.10)alkoxy and the other of Ar.sub.1a and Ar.sub.1b is 2-6-dihalophenyl or 2,6-di(C.sub.1 -C.sub.10)alkyl.

### Claim 5

A compound represented by the formual II
Ar.sub.1a --O--M--O--Ar.sub.1b II
wherein Ar.sub.1a is 4-(C.sub.1 -C.sub.10) alkoxyl-2-halophenyl and Ar.sub.1b is 2,6-dihalophenyl; M is ##STR32## O is oxygen.

### Claim 6 (depends on 5)

A compound of claim 5 which is 2-chloro-1-[[4-[(2,6-dichlorophenoxy)methyl]phenyl]methoxy]-4-methoxybenze ne.

### Claim 7 (depends on 5)

A pharmaceutical composition for treating susceptible viral infections which comprises an antivirally effective amount of a compound of claim 5 and a pharmaceutically acceptable carrier.

### Claim 8 (depends on 6)

A pharmaceutical composition for treating susceptible viral infections which comprises an antivirally effective amount of a compound of claim 6, which is 2-chloro-1-[[4-[2,6-dichlorophenoxy) methyl]phenyl]methoxy]-4-methoxybenzene and a pharmaceutically acceptable carrier.

### Claim 9 (depends on 2)

A pharmaceutical composition for treating susceptible viral infections which comprises an anti-virally effective amount of a compound of claim 2 and a pharmaceutically acceptable carrier.