Patent GB-1079694-A (GB)
Title: Antiviral compositions
IPC: A61K31/13
Filed: 1966-01-28
Abstract: Aerosol compositions having pharmaceutical activity comprise a cycloalkylamine of formula <FORM:1079694/C4-C5/1> wherein n is 6 to 11, and R and R1 are each hydrogen; or, when alkyl, alkenyl, and acyl are C1 to C6, are alkyl, alkenyl, acyl, hydroxyalkyl, dialkylaminoalkyl, or phenyl alkyl; or, when one of R and R1 is hydrogen or alkyl, are hydroxy, amino, carbamoyl, thiocarbamoyl, or amidino; or together with the nitrogen atom, form a heterocycle; or the acid addition salts thereof or the N-oxides thereof, together with a volatile propellant, and packed in an aerosol dispenser.  The compositions may also include a solvent carrier, such as alcohol; suitable propellants are "Freon 12" or "Freon 114" (Registered Trade Mark).  An example is given for an aerosol composition containing both of these propellants and N-ethylcyclononylamine. The compositions are for oral or nasal application to treat virus infections (see Divisions A5-A6).ALSO:N-Allylcyclo-octylamine, and the corresponing N,N-diallyl compound, are prepared by reacting allyl bromide and cyclo-octylamine as the hydrochloride in ethanolic solution in the presence of Na2HCO3; the reaction product, separated by ether extraction, is distilled to fractionate the two said compounds.  By analogous procedures, the following are prepared from the accompanying starting materials: N-hexyl- and N,N-dihexyl-cyclododecylamine, from hexyl bromide and cyclododecylamine hydrochloride; N-(3-dimethyl-aminopropyl)- and N,N - bis(3 - dimethylaminopropyl) - cyclododecylamine, from 3 - di-methylamino propyl bromide and cyclododecylamine hydrochloride; N-(2-hydroxyethyl)- and N,N - bis(2 - hydroxyethyl) - cyclo - octylamine from 2-chloroethanol and cyclo-octylamine hydrochloride; N-benzyl- and N,N-dibenzylcycloheptylamine from benzylbromide and cycloheptylamine hydrochloride.  1-Pyrrolidinocyclononane is prepared by the same procedure from cyclononyl bromide and pyrrolidine.  N - Methyl - N - acetylcyclooctylamine is prepared by refluxing sodium hydride with N-acetylcyclooctylamine in tetrahydrofuran solution, adding a tetrahydrofuran solution of methyl iodide to the refluxed mixture, and heating further, after which the reaction mixture is worked up to the said compound.  Cycloheptylhydrazine is prepared by reacting hydrazine hydrate and cycloheptyl bromide. N-Hydroxycyclononylamine is prepared by reacting cyclononanone with hydroxylamine hydrochloride to give the oxime, which is catalytically reduced by hydrogenation to the said amine.  These compounds are used as the active ingredient of pharmaceutical compositions (see Divisions A5-A6).ALSO:Pharmaceutical compositions, having antiviral properties, comprise, as active ingredient, a cycloalkylamine of formula:  <FORM:1079694/A5-A6/1> wherein n is 6 to 11, and R and R1 are each hydrogen or, when alkyl, alkenyl, and acyl are C1 to C6, are alkyl, alkenyl, acyl, hydroxyalkyl, dialkylamino alkyl, or phenylalkyl; or when one of R and R1 is hydrogen or alkyl, are hydroxy, amino, carbamoyl, thiocarbamoyl, or amidino; or together with the nitrogen atom, form a heterocycle; or the acceptable acid addition salts thereof, or the N-oxides thereof, together with a pharmaceutical carrier.  The compositions may take oral forms, including sustained release dosage units, or injectable, inhalable, or topical forms, e.g. tablets, capsules, troches, lozenges, sustained release tablets or capsules, enterically coated tablets, sterile injectable oily or aqueous solutions or suspensions, inhalers, such as a spray pack or an aerosol (see Div. C4-C5) or as a volatile inhalant composition, or dermatological ointments.  The compositions may also be included in or added to animal feeds or feed supplements.  Other active ingredients may be present, such as vitamins; antibiotics, e.g. bacitracin, neomycin, polymixin B, or gramicidin; hormones; analgesics, e.g. dextro-propoxyphene or etoheptazine; antihistamines, e.g. chlor pheniramine, or tripelknnamine; decongestants, e.g. phenylephrine, phenylpropanolamine, or propyl hexedrine; or antitussives, e.g. caramiphen.