Kao Soap Company, Ltd.

Koji Aigami

Yoshiaki Inamoto

Yoshiaki Fujikura

Naotake Takaishi

Motoyoshi Ohsugi

Hiroshi Ikeda

Motoki Nakajima

Kiyoshi Tsuchihashi

1-Aminomethyltricyclo[4.3.1.1.sup.2,5 ]undecane having the formula (I) and acid-addition salts thereof possess an excellent inhibitory effect on the growth of viruses even at a low concentration. ##STR1##

1-Aminomethyltricyclo[4.3.1.1.sup.2,5 ]undecane and acid-addition salts

3-Alkoxy-4-homoisotwistanes the formula (I), ##STR1## wherein R is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 to 6 carbon atoms, are prepared by a process which comprises reacting a 3-halogeno-4-homoisotwistane of the formula (II), ##STR2## wherein X is a chlorine or bromine atom, with an alcohol of the formula (III),

3-Alkoxy-4-homoisotwistanes

Tricyclo[4.3.1.1.sup.2,5 ]undecane-1-carboxylic acid and acid halides and esters thereof having the formula (I), ##STR1## wherein Y represents a hydroxy group, a chlorine or bromine atom, or an alkoxy group of the formula RO- wherein R is a straight-chain, branched-chain or cyclic alkyl group having 1 to 12 carbon atoms, include compounds which exhibit superior antiviral action.

Tricyclo[4.3.1.1.sup.2,5 ]undecane-1-carboxylic acid and derivatives

1-Alkoxytricyclo[4.3.1.1.sup.2,5 ]undecanes having the formula (I), ##STR1## wherein R represents an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 to 6 carbon atoms are prepared by a process which comprises reacting 1-halogenotricyclo[4.3.2.1.sup.2,5 ]undecanes the formula (II), ##STR2## wherein X is a chlorine or bromine atom, with alcohols of the formula (III),

1-Alkoxytricyclo[4.3.1.1.sup.2,5 ]undecanes

A process for preparing 3-acylamino-4-homoisotwistances which comprises reacting 4-homoisotwistane with a nitrile, bromine and water.

Process for preparation of 3-acylamino-4-homoisotwistane

1-Halogenotricyclo [4.3.1.1.sup.2,5 ] undecanes are prepared by reacting tricyclo [4.3.1.1.sup.2,5 ] undecane with bromine or by reacting tricyclo [4.3.1.1.sup.2,5 ] undecane-1-ol with thionyl halide. The compounds are useful intermediates for preparing 1-aminotricyclo [4.3.1.1.sup.2,5 ] undecane hydrochloride which has antiviral activity.

1-Halogenotricyclo [4.3.1.1.sup.2,5 ] undecane and process for the

1-Acetylaminotricyclo [4.3.1.1.sup.2,5 ] undecane is prepared by reacting either (a) 1-substituted tricyclo [4.3.1.1.sup.2,5 ] undecane, wherein the substituent is Cl, Br or OH, or (b) endo-2-hydroxymethyl-exo-2,3-trimethylenenorbornane with acetonitrile, in the presence of sulfuric acid. 1-Acetylaminotricyclo [4.3.1.1.sup.2,5 ] undecane is useful as an intermediate to prepare antiviral substances.

1-Acetylaminotricyclo [4.3.1.1.sup.2,5 ] undecane and process for the

1-Amino-tricyclo [4.3.1.1.sup.2,5 ] undecane is prepared by alkaline hydrolysis of 1-acetylamino-tricyclo [4.3.1.1.sup.2,5 ] undecane, and its acid addition salts are prepared by neutralizing it with an acid. The compounds possess antiviral activity.

1-Aminotricyclo (4.3.1.1.sup.2,5) undecane and salts thereof

Tricyclo[6.2.1.0.sup.2,6 ]undeca-2(6)-ene is disclosed and there is further disclosed a process for the hydride transfer reduction rearrangement of tricyclo[6.2.1.0.sup.2,6 ]undeca-2(6)-ene having the formula (I): ##STR1## by subjecting tricyclo[6.2.1.0.sup.2,6 ]undeca-2(6)-ene having the formula (I) to rearrangement with concentrated sulfuric acid in the presence of a hydride source to convert it to 4-homoisotwistane (tricyclo[5.3.1.0.sup.3,8 ]undecane) having the formula (II): ##STR2##

Tricyclo[6.2.1.0.sup.2,6 ]undeca-2(6)-ene and process for hydride

Adamantyl thioamides having the formula: ##EQU1## in which Ad is adamantyl or alkyl-substituted adamantyl; m is a number of 0 or 1, n is a number of 1 or 2, with the proviso that m is 1, when n is 2; and the aminothiocarbonylmethyl or the aminothiocarbonyl group is bonded to a bridgehead carbon atom of the adamantane ring, are prepared by reacting a nitrile having the formula

Adamantyl thioamides

New amidine compounds of formula (I): ##EQU1## wherein R represents ##SPC1## (R' being H or CH.sub.3) and acid addition salts thereof, are prepared by reacting a nitrile of formula (II):

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Wakayama, Japan

Koji Aigami