GB1063365A - Improvements relating to derivatives of adamantane - Google Patents

Abstract

Novel compounds of the formula <FORM:1063365/C2/1> and their salts with non-toxic acids, wherein A is an amino group of the formula <FORM:1063365/C2/2> in which R1 and R2 are each a C3- 12 alkenyl or alkynyl group having at least one CH2 group between the N-atom and the first olefinic or acetylenic bond or a C3- 8 cycloalkyl or C3- 9 cycloalkylmethyl group in which the cycloalkyl portion may carry one or two CH3 or C2H5 substituents, or R1 may also be hydrogen; and R1 and R2 together contain at most 12 carbon atoms, are made by (1) reacting 1-amino-adamantane with the appropriate halide R1 Hal and/or R2 Hal; (2) forming an N-cycloalkyl acylamido-adamantane by reacting 1-bromo-adamantane with an N-cycloakyl acylamide, e.g. N-cyclohexylacetamide, in the presence of silver sulphate and hydrolysing to give a product wherein R1 is hydrogen and R2 is a cycloalkyl group or (c) forming a 1-acylamino-adamantane e.g. 1-(4-methyl-3-hexen-1-oylamino) adamantane and reducing with LiAlH4. The products are used pharmaceutically (see Division A5) suitably in the form of their salts with organic or inorganic acids, e.g. penicillin and 4 - (o - chlorobenzyl) - 5 - oxo - 4 - phenylhexanoic acid.ALSO:Pharmaceutical preparations having anti-viral activity comprise compounds of the formula <FORM:1063365/A5-A6/1> and their salts with non-toxic acids (e.g. conventional inorganic and organic acids, especially hydrochloric, acetic 4-(o-chlorobenzyl)-5-oxo-4-phenyl-hexanoic and penicillin), wherein A is an amino group of the formula <FORM:1063365/A5-A6/2> in which R1 and R2 are each a C3-12 alkenyl or alkynyl group having at least one CH2 group between the N-atom and the first olefinic or acetylenic bond, or a C3-8 cycloalkyl or C3-9 cycloalkylmethyl group in which the p cycloalkyl portion may carry one or two CH3 or C2H5 substituents, or R1 may also be hydrogen, together with a pharmaceutically acceptable carrier. A method for combatting virus infections in animals comprises administering to the site of the infection an anti-viral amount of the above compounds. The preparations may take forms adapted to oral or parenteral, administration e.g. tablets, capsules, powder packets or solutions or may be in the form of a spray for mouth or nasal passages. For veterinary use the active compounds may be incorporated in an animal feedstuff or feedstuff concentrate and may contain, in addition to conventional diluents, proteins, carbohydrates, fats, vitamins, minerals and antibiotics.