Richardson-merrell Inc.

Warner-lambert Company

Parke-davis Company

Robert W Fleming

William L Albrecht

Arthur D Sill

Francis W Sweet

Ivan C Nordin

Stephen W Horgan

Sandra J Lobbestael

Albert A Carr

Johann M Grisar

Laird F Miller

N-(2,6-Disubstitutedphenyl)-N'-3- and 4-pyridinyl ureas and pharmaceutically acceptable acid addition salts having anticonvulsant activity are described as well as a process for their manufacture, formulations containing the compounds and a method of treating epilepsy using the compounds in unit dosage form.

N-(2,6-disubstituted aromatic)-N'-pyridinyl ureas

Anticonvulsant N-(2,6-disubstituted aromatic)-n'-pyridinyl ureas

The invention provides new N-(2,6-dimethylphenyl)-2-methylthio-1-imidazolidinecarboxamides and their pharmaceutically acceptable salts which are useful as anticonvulsant agents. Also provided are methods for preparing the compounds of the invention, pharmaceutical compositions containing said compounds and methods for using said compositions.

N-(2,

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

(+,-)-cis-.alpha.[3-(2,6-Dimethyl-1-piperidinyl)propyl]-.alpha.-phenyl-2-py ridinemethanol and acid-addition salts. The compounds are pharmacological agents, especially antiarrhythmic agents. The compounds can be produced by reacting pyridyllithium with cis-.gamma.-(2,6-dimethylpiperidino)butyrophenone, or by reacting cis-1-(3-lithiopropyl)-2,6-dimethylpiperidine with 2-benzoylpyridine. Pharmaceutical compositions comprising (+,-)-cis-.alpha.-[3-(2,6-dimethyl-1-piperidinyl)propyl]-.alpha.-phenyl-2- pyridinemethanol and acid-addition salts thereof and methods for treating cardiac arrhythmia using said pharmaceutical compositions are also disclosed.

Antiarrhythmic

Novel 1,5 and 1,8-bis-basic ketones of anthracene useful for the prevention and inhibition of viral infections are prepared by reacting 1,5 and 1,8 bis(.omega.-haloacyl)anthracenes with a secondary amine.

Anthracene derivatives

Disclosed are novel compounds and pharmaceutical formulations having antiviral activity. The disclosed compounds have the formula ##STR1## wherein one R.sup.2 is a hydrogen atom and the other R.sup.2 is the radical ##STR2## A is a straight chain alkylene group having 2 or 3 carbon atoms and each R.sup.3 and R.sup.4 is a hydrogen atom, and alkyl radical having 1 to 3 carbon atoms or each set of R.sup.3 and R.sup.4 taken together with the nitrogen atom to which they are attached is a saturated monocyclic heterocyclic group. Also included are the acid addition salts of these bases. These compounds may be prepared by various methods which are described.

Bis-basic ethers of 2,6,- and 2,7-dihydroxy-anthraquinones

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

cis-2,6-Dimethyl-.alpha.,.alpha.-diphenyl-1-piperidinebutanol; and acid-addition salts. The compounds are pharmacological agents, especially antiarrythmic agents. The compounds can be produced by reacting phenyl lithium or phenylmagnesium halide with cis-.gamma.-(2,6-dimethylpiperidino)butyrophenone or a lower alkyl ester of cis-2,6-dimethyl-1-piperidinebutyric acid; by reacting .alpha.-(3-halopropyl)-.alpha.-phenylbenzyl alcohol with cis-2,6-dimethylpiperidine, or by reacting cis-1- (3-lithiopropyl)-2,6-dimethylpiperidine with benzophenone.

Cis-2,6-dimethyl-.alpha.,.alpha.-diphenyl-1-piperidinebutanol compounds

Compounds useful as antiviral agents are those of the formula ##SPC1## Wherein each R.sup.1 is hydrogen or methyl; each n is an integer of 2 to 4; each of R.sup.2 and R.sup.3 is alkyl of 3 to 5 carbon atoms or alkenyl of 3 to 5 carbon atoms; or a pharmaceutically acceptable acid addition salt of said base. Pharmaceutical compositions are formed from these compounds with pharmaceutically acceptable carriers.

Bis(aminoalkylsulfamoyl)anthraquinone antiviral agents

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

Disclosed are novel compounds and pharmaceutical formulations having antiviral activity. The disclosed compounds have the formula ##SPC1## Wherein one R.sup.2 is a hydrogen atom and the other R.sup.2 is the radical ##SPC2## A is a straight chain alkylene group having 2 or 3 carbon atoms and each R.sup.3 and R.sup.4 is a hydrogen atom, an alkyl radical having 1 to 3 carbon atoms or each set of R.sup.3 and R.sup.4 taken together with the nitrogen atom to which they are attached is a saturated monocyclic heterocyclic group. Also included are the acid addition salts of these bases. These compounds may be prepared by various methods which are described.

Bis-basic ethers of 2,6- and 2,7-dihydroxyanthraquinones

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 bis-basic esters and amides of xanthene and xanthone of the formula ##SPC1## Wherein:

Antiviral compositions containing bis-basic esters and amides of

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

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Cincinnati, OH, United States of America

Robert W Fleming