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

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.

Claims8

Dependent claims

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.

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.

9 more elements

Dependencies are inferred from the claim text.

Antiviral 1-aryl-5-amino-1-penten-3-ones

Life of this patent

Antiviral 1-aryl-5-amino-1-penten-3-ones

Life of this patent

Abstract

Claims8