GB1175820A - Amino-Adamantane Derivatives - Google Patents

Abstract

1,175,820. Adamantane derivatives. UPJOHN CO. 30 Jan., 1967 [18 Feb., 1966], No. 25623/69. Divided out of 1,173,492. Heading C2C. Novel adamantane derivatives of formulµ in which R is hydrogen, C 1-18 alkyl, C 7-13 aralkyl or C 3-6 cycloalkyl-methyl and X<SP>1</SP> is hydroxy or keto, and, when R is not hydrogen, the corresponding tetrahydropyranyl ethers thereof, are prepared by (a) hydrolysing a compound of the formula in which Acyl is the acyl radical of a monobasic hydrocarbon carboxylic acid of 1 to 18 carbon atoms, with an aqueous strong base to produce a corresponding 1-aminoadamantane of Formula I or II in which R is hydrogen, or (b) reducing a compound of formula in which Acyl is C 1-18 alkanoyl, C 7-13 aralkanoyl or C 3-6 cycloalkyl-carbonyl, with lithium aluminium hydride, hydrolysing the 1-aminoadamantane tetrahydropyranyl ether so obtained with a strong acid in the presence of an organic solvent and treating the resulting 1-amino-adamantane acid addition salt with a base to produce the corresponding compound of formula in which R<SP>11</SP> is the same as R except for hydrogen, and, if desired, subjecting the 4-hydroxy compounds of Formula VIII to an Oppenauer oxidation reaction to obtain the corresponding 4-keto compounds. The compounds of Formulµ I and II may be converted into pharmacologically acceptable acid addition salts by conventional methods. Pharmaceutical compositions having central nervous stimulant activity, for oral or parenteral administration, comprise a compound of Formula I or II, or a pharmaceutically acceptable acid addition salt thereof, together with a carrier.