Richardson-Merrell Inc.

William L Albrecht

Robert W Fleming

Winton D Jones

Arthur D Sill

Stephen W Horgan

Francis W Sweet

Compounds of the formula ##STR1## wherein R.sub.1 is H or NH.sub.2 ; R.sub.2 is C.sub.1-6 straight or branched chain alkyl; --CH.sub.2 OH; --(CH.sub.2).sub.n --O--(CH.sub.2).sub.m --CH.sub.3 ; phenyl; or --(CH.sub.2).sub.p NH.sub.2 ;

Antisecretory 1,2,4-triazole-3-thiols

Compounds of the formula ##STR1## wherein R.sub.1 is H or NH.sub.2 ;

1,2,4-Triazole-3-thiols as antisecretory agents

Antiviral compositions and methods of inhibiting or inactivating viruses by administering to hosts an effective quantity of an active ingredient are disclosed herein. The active ingredients are those compounds having the formula ##STR1## wherein A is a straight or branched alkylene chain of from 1 to 6 carbon atoms and each Y is the group

Method of treating viruses with bis-basic ketones of dibenzofuran

The novel bis-basic ketones of fluorene and fluorenone of the present invention have antiviral activity when administered orally and parenterally. These compounds are represented by the following formula: ##STR1## wherein Z is oxygen or H.sub.2 ; each A is a straight or branched alkylene chain having from 1 to about 6 carbon atoms; and each Y is A. the group ##STR2## wherein R.sup.1 and R.sup.2 are individually hydrogen, (lower)alkyl having from 1 to about 6 carbon atoms, cycloalkyl having from 3 to 6 carbon atoms, alkenyl of from 3 to 6 carbon atoms and having the vinyl unsaturation in other than the 1-position of the alkenyl group; or B. the group ##STR3## WHEREIN N IS A WHOLE INTEGER FROM 4 TO 6, AND R.sup.3 is hydrogen, (lower)alkyl of 1 to about 4 carbon atoms, phenyl, or benzyl and can be linked to any one of the carbon atoms of the heterocyclic group; or C. the group ##STR4## wherein X is oxygen or NR.sup.4, and R.sup.4 is hydrogen or (lower)alkyl of from 1 to about 4 carbon atoms; or D. the group ##STR5## WHEREIN P IS A WHOLE INTEGER FROM 2 TO 3, AND M IS A WHOLE INTEGER FROM 1 TO 2; OR A PHARMACEUTICALLY ACCEPTABLE ACID ADDITION SALT OF SAID BASE. These new compounds may be prepared by several different methods which are described.

Bis-basic ketones of fluorene and fluorenone

Novel 2,7-bis-basic derivatives of fluorene, 9-fluorenol and 9-fluorenone, their preparation and use for the prevention and inhibition of virus infections are disclosed.

Fluorene compounds

Novel 3,6-bis-basic alkanes of carbazole, their preparation and use for the prevention and inhibition of viral infections are disclosed.

Carbazole derivatives

Novel triazolobenzocycloalkylthiadiazines, their preparation, and use as central nervous system antidepressants.

Triazolobenzocycloalkylthiadiazine derivatives

Novel triazolocycloalkylhydrothiadiazines and their preparation, which are useful as antisecretory agents, central nervous system stimulants, and central nervous system depressants, are disclosed.

Triazolocycloalkylhydrothiadiazine derivatives

Novel triazolocycloalkylthiadiazines, their preparation, and use as antisecretory agents and central nervous system depressants.

Triazolocycloalkylthiadiazine derivatives

Novel bis-basic esters and amides of dibenzothiophene of the formula ##SPC1## Wherein:

Bis-basic esters and amides of dibenzothiophene

The novel bis-basic ketones of carbazole of the present invention have antiviral activity when administered orally and parenterally. These compounds are represented by the following formula: ##SPC1## Wherein Z is hydrogen or lower alkyl having from 1 to 4 carbon atoms; A is a straight or branched alkylene chain having from 1 to about 6 carbon atoms; and each Y is

Bis-basic ketones of carbazole

Novel bis-basic esters and amides of carbazole of the formula ##SPC1## Wherein:

Bis-basic esters and amides of carbazole

The novel bis-basic ethers of carbazole of the present invention have useful antiviral properties. These new compounds are represented by the formula ##SPC1## Wherein Z is hydrogen or lower alkyl having from 1 to 4 carbon atoms; and each X is ##EQU1## A. the group -A-N wherein each A is a straight or branched alkylene chain having from 2 to 6 carbon atoms; R and R.sup.1 are individually hydrogen or lower alkyl having from 1 to 6 carbon atoms; or each set of R and R.sup.1 taken together with the nitrogen atom to which they are attached is a saturated monocyclic heterocyclic group such as pyrrolidino or piperidino; or B. the group ##SPC2## Wherein n is a whole integer from 0 to 2, m is 1 or 2, and R.sup.2 is hydrogen or lower alkyl having from 1 to 4 carbon atoms. This invention also includes pharmaceutically acceptable acid addition salts of the bases represented by Formula I. These new compounds may be prepared by several different methods which are described.

Growing community of inventors

Cincinnati, OH, United States of America

William L Albrecht