# US 4,400,380 A · Antiviral 1-aryl-5-amino-1-penten-3-ones

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- Number: US 4,400,380 A
- Document ID: US4400380A
- Status: Granted
- Kind: A
- Application number: 06/276,139
- Filed: 1981-06-22
- Granted: 1983-08-23
- Earliest claimed: 1980-07-02
- Assignees: Merrell Dow Pharmaceuticals Inc.
- Inventors: Harry W. Ritter; Michael L. Edwards
- Web page: https://patentgrep.com/patent/US4400380A

## CPC

- C07D 295/108: to an acyclic saturated chain
- C07C 45/45: by condensation
- C07C 45/74: combined with dehydration
- C07C 255/00: Carboxylic acid nitriles (cyanogen or compounds thereof C01C3/00)
- C07D 317/54: Radicals substituted by oxygen atoms
- C07D 317/58: Radicals substituted by nitrogen atoms (nitro radicals C07D317/52)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Compounds of the formula ##STR1## wherein R is H, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, 3,4-methylenedioxy, CF.sub.3, NO.sub.2, NH.sub.2, N(C.sub.1-4 alkyl).sub.2, CN, OH, --S(C.sub.1-4 alkyl) or --SO.sub.2 (C.sub.1-4 alkyl); R.sub.1 and R.sub.2 are independently each H or C.sub.1-4 alkyl or taken together with the attached N atom are morpholino, piperidino, pyrrolidino, piperazino, or N-- C.sub.1-4 -alkyl piperazino; and, when R is halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, x is 0-3 and, otherwise, is 0 or 1; or a pharmaceutically acceptable salt thereof with an acid or for the compounds wherein R.sub.1 and R.sub.2 are both not H, a quaternary ammonium salt thereof with a C.sub.1-4 alkyl halide have valuable antiviral activity, e.g., for treatment of infections caused by a herpes virus.

## Claims

### Claim 1

A method of treating a viral infection amenable to topical treatment comprising topically administering to a patient afflicted with such a viral infection an antivirally effective amount of a compound of the formula ##STR11## wherein R is H, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, 3,4-methylenedioxy, CF.sub.3, No.sub.2, NH.sub.2, N(C.sub.1-4 alkyl).sub.2, CN, OH, --S(C.sub.1-4 alkyl) or --SO.sub.2 (C.sub.1-4 alkyl); R.sub.1 and R.sub.2 are independently each H or C.sub.1-4 alkyl or taken together with the attached N atom are morpholino, piperidino, pyrrolidino, piperazino, or N-C.sub.1-4 --alkyl piperazino; and, when R is halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, x is 0-3 and, otherwise, is 0 or 1;
or a pharmaceutically acceptable salt thereof with an acid or for the compounds wherein R.sub.1 and R.sub.2 are both not H, a quaternary ammonium salt thereof.

### Claim 2 (depends on 1)

The method of claim 1 wherein the patient is afflicted with an infection mediated by a herpes virus.

### Claim 3 (depends on 1)

The method of claim 1 wherein R.sub.x is H, monohalo or dihalo and NR.sub.1 R.sub.2 is morpholino or dialkylamino.

### Claim 4 (depends on 3)

The method of claim 3 wherein x is H, and R.sub.1 and R.sub.2 are methyl, said compounds being in the form of a quaternary ammonium salt.

### Claim 5 (depends on 1)

The method of claim 1 wherein the compound administered is 5-(4-morpholinyl)-1-phenyl-1-penten-3-one or 5-(4-morpholinyl)-1-(3,4-dichlorophenyl)-1-penten-3-one or the hydrochloride salts thereof.

### Claim 6

A quaternary salt of a compound of the formula ##STR12## wherein R is H, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, 3,4-methylenedioxy, CF.sub.3, NO.sub.2, CN, OH, --S(C.sub.1-4 alkyl)or --SO.sub.2 (C.sub.1-4 alkyl); R.sub.1 and R.sub.2 are each C.sub.1-4 alkyl or taken together with the attached N atom are morpholino, piperidino, pyrrolidino, piperazino, or N-C.sub.1-4 --alkyl piperazino; when R is halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, x is 0-3 and, otherwise, is 0 or 1; or the free base and their acid addition salts of compounds of Formula I with the proviso that when R is H, R.sub.1 and R.sub.2 are not both alkyl or together with the attached N atom are not morpholino, pyrrolidino or piperidino; when R.sub.x is monochloro, R.sub.1 and R.sub.2 are not both dialkyl or together with the N atom to which they are attached are not morpholino or piperidino; when R.sub.x is dichloro, R.sub.1 and R.sub.2 are not both alkyl; when R.sub.x is monoalkyl, R.sub.1 and R.sub.2 are not both alkyl; when R.sub.x is dialkyl, R.sub.1 and R.sub.2 together with the N atom to which they are attached are not pyrrolidino; when R is mono- or di-alkoxy, R.sub.1 and R.sub.2 are not both alkyl and together with the N atom to which they are attached are not morpholino, pyrrolidino, or piperidino; when R is 3,4-methylenedioxy, R.sub.1 and R.sub.2 are not both alkyl and together with the N atom to which they are attached are not morpholino or piperidino; when R is NO, R.sub.1 and R.sub.2 are not both alkyl and together with the N atom to which they are attached are not morpholino, pyrrolidino or piperidino; when R is dialkylamino, R.sub.1 and R.sub.2 together with the N atom to which they are attached are not morpholino or piperidino; and when R.sub.x is OH and alkoxy, R.sub.1 and R.sub.2 are not both alkyl and together with the N atom to which they are attached are not morpholino, pyrrolidino or piperidino.

### Claim 7 (depends on 6)

A compound of claim 6 wherein R.sub.x is H, monohalo or dihalo and NR.sub.1 R.sub.2 is morpholino or dialkylamino.

### Claim 8 (depends on 6)

A quaternary salt of a compound of claim 6 wherein the compound is 5-(4-morpholinyl)-1-(3,4-dichlorophenyl)-1-penten-3-one.