The present invention is directed to adamantane compounds of the formulae: ##SPC1## ##SPC2## Wherein each G independently represents hydrogen or straight-chain alkyl of from 1 to 6, both inclusive, carbon atoms; G' represents hydrogen or acetyl; R represents hydrogen or alkyl of from 1 to 6, both inclusive, carbon atoms; R' represents halo, alkoxy containing from 1 to 6, both inclusive, carbon atoms in the alkyl group, hydrogen or alkyl of from 1 to 6, both inclusive, carbon atoms; each R" independently represents hydrogen or alkyl of from 1 to 6, both inclusive, carbon atoms; each R"' independently represents hydrogen or alkyl of from 1 to 6, both inclusive, carbon atoms, or both R"' groups taken together represent oxo(=O); X represents halo; and each n independently represents an integer of from 0 to 1, both inclusive. The terms "halo" and "halide" are employed herein to designate occurrences of bromine, chlorine, and iodine. The adamantane compounds of formulae VII and VIII are useful as agents to achieve a depressant action on the central nervous system of warm blooded animals. The adamantane compounds of Formulae I, II, III, IV, V and VI are useful as intermediates in the synthesis of the compounds of Formulae VII and VIII.
CROSS-REFERENCE TO RELATED APPLICATIONS
This is a continuation of our copending application Ser. No. 197,175, filed Nov. 9, 1971 now abandoned, which was in turn a division of our then copending application Ser. No. 32,406, filed Apr. 27, 1970 and issued June 6, 1972 as U.S. Pat. No. 3,668,220. Application Ser. No. 32,406 was, in turn, a division of our then copending application Ser. No. 675,037, filed Oct. 13, 1967 and issued July 6, 1971 as U.S. Pat. No. 3,591,642.
Novel 2-substituted-1-methylamino adamantanes of formula: ##STR1## where X is hydroxyl or halogeno, and R.sup.1, R.sup.2 and R.sup.3 are hydrogen or C.sub.1-4 alkyl or R.sup.2 and R.sup.3 together with the nitrogen form a heterocyclic ring, having anti-Parkinsonian activity, pharmaceutical formulations containing the active adamantanes and novel 4-protoadamantane spiro oxirane and 1,2-difunctionalized intermediates useful in the preparation of the final products of the invention.
