Merck + Co., Inc.

Burroughs Wellcome Co.

Robert A Strelitz

Nathaniel Grier

Richard A Dybas

Gertrude B Elion

Richard L Tolman

Malcolm MacCoss

Bruce E Witzel

Disclosed are compounds of the formula: ##STR1## and the pharmaceutically acceptable salts thereof wherein R.sup.1 and R.sup.2 are independently alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl, each having 1 to 19 carbon atoms, or R.sup.2 is hydrogen; R.sup.3 is hydrogen, alkyl having 1 to 6 carbon atoms or hydroxyalkyl having 1 to 6 carbon atoms; R.sup.4 is hydrogen, halogen, amino or alkyl having 1 to 4 carbon atoms; R.sup.5, R.sup.6 and R.sup.7 are independently selected from hydrogen, hydroxy, alkyl having 1 to 6 carbon atoms, acyloxy having 1 to 8 carbon atoms, alkoxy having 1 to 6 carbon atoms, hydroxyalkyl having 1 to 6 carbon atoms, acyloxyalkyl having 1 to 12 carbon atoms, amino, alkylamino of 1 to 6 carbon atoms and --PO.sub.3.sup.=, or two of R.sup.5, R.sup.6 and R.sup.7 taken together form a group --OPO.sub.2 O.sup.- --, --CH.sub.2 OPO.sub.2 O.sup.- --, --CH.sub.2 OPO.sub.2 OPO.sub.2 O.sup.= --, or --OPO.sub.2 OPO.sub.2 O.sup.= --; A is O, S or CH.sub.2 and X is a pharmaceutically acceptable anion. The compounds have antiviral activity, especially against viruses of the herpes class.

N-alkylguanine acyclonucleosides as antiviral agents

A process for preparing 1-[1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentyl]-1,5,9-triazanonane from 1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentanone by reaction with ammonia to form, after reduction, 3-amino-[1,5-di-(3,3-dimethylnorborn-2-yl)pentane]. This latter compound is reacted with acrylonitrile, reduced, and the diamine product again reacted with acrylonitrile and again reduced. Alternative routes wherein the ketone is reduced to the novel alcohol and optionally the novel halide and either then reacted with 3,3'-iminobispropylamine to form the desired polyamine are also shown.

Process for preparation of

Novel dibicyclo [2.2.2] octyl dibicyclo [2.2.2] octenyl polyamines are useful antimicrobial agents, as well as algae inhibitors. They are especially useful as hard surface disinfectants and as additives to oil well drilling muds, injection brines and industrial water where bacterial control is desired.

Novel dibicyclo [2.2.2] octyl and dibicyclo [2.2.2] octenyl polyamines

A method and composition of treating a mammal suffering from an autoimmune disease which comprises internally administering to the mammal an effective autoimmune suppressant amount of the compound of formula or its pharmaceutically acceptable salts ##STR1## where R.sup.1 is amino or lower alkylamino and R.sup.2 is amino or hydrogen, provided that when R.sup.1 is amino, R.sup.2 is amino.

Amino purine nucleosides as autoimmune suppressant agents

Novel dibicyclo [3.1.1] and [2.2.1] heptyl and dibicyclo [3.1.1] and [2.2.1] heptenyl polyamines are useful antimicrobial agents, as well as algae inhibitors. They are especially useful as hard surface disinfectants and as additives to oil well drilling muds, injection brines and industrial water where bacterial control is desired.

Novel dibicyclo [3.1.1] and [2.2.1] heptyl and dibicyclo [3.1.1] and

Novel dicyclohexyl, dicyclohexenyl and cyclohexylcyclohexenylalkyl polyamines are useful antimicrobial agents, as well as algae inhibitors. They are especially useful in agriculture to protect plants against diseases such as leaf, stem, and fruit spotting, internal discoloration and decay of fruits and vegetables. These compounds are particularly active against diseases caused by the genera Pseudomonas, Xanthomonas, Erwinia, and Corynebacterium.

Alicyclic alkylene polyamine microorganism and algae growth inhibitors

An antimicrobial composition for secondary and tertiary oil recovery comprising a flooding composition consisting of displacement and driving fluids having incorporated therein an antimicrobially effective amount of a di-bicyclo[3.1.1] or [2.2.1] heptyl or di-bicyclo[3.1.1] and [2.2.1] heptenyl polyamines or salts thereof.

Composition for secondary and tertiary oil recovery

Compounds of the formula ##STR1## where R.sup.1 is amino or lower alkylamino, R.sup.2 is amine or hydrogen and pharmaceutically acceptable salts thereof, provided that when R.sup.1 is amino, R.sup.2 is amino. The compounds are useful as immune suppressants and as antivirals.

Amino purine derivatives

Novel dibicyclo [3.1.1] and [2.2.1] heptyl and dibicyclo [3.1.1] and [2.2.1] heptenyl polyamines having a cyclohexylene group in the polyamine moiety are useful antimicrobial agents, as well as algae inhibitors. They are especially useful as hard surface disinfectants and as additives to oil well drilling muds, injection brines and industrial waters where microbial control is desired.

Novel dibicyclo [3.1.1] and [2.2.1] heptyl and dibicyclo [3.1.1] and [2.2.1] heptenylalkyl polyamines are useful antimicrobial agents, as well as algae inhibitors. They are especially useful as hard surface disinfectants and as additives to oil well drilling muds, injection brines and industrial water where bacterial control is desired.

Growing community of inventors

Edison, NJ, United States of America

Robert A Strelitz