Patent IE-39712-L (IE)
Title: Bornamine and 7,7- dimethyl norbornanamine derivatives;¹antiviral compositions
IPC: C07C67/00
Filed: 1974-03-05
Abstract: This invention relates to a process for the preparation of 7,7dimethyl-2,2,1!-bicycloheptanes having at the 1-positions a group R, and the physiologically acceptable salts thereof, wherein R is an amino or aminomethyl group possessing a basic nitrogen atom and is substituted at the amino nitrogen atom (via a single or double bond) and/or at the 10- carbon atom by one or more C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl groups, which may be unsubstituted or substituted by an amino, mono or dialkylamino,imino, hydroxy, thiol, an esterified or etherified hydroxy or thiol group or (when a basic nitrogen atom is also present on the group) an oxo group in an .alpha.-position in relation to the R nitrogen atom; a C3-8 cyclo-alkyl group; a monocyclic aralkyl, aralkenyl or aralkynyl group; a phenyl group or substituted phenyl group; a 5 or 6 membered heterocyclic aryl group; or wherein the nitrogen atom of R forms part of 4 to 8 membered heterocyclic ring which may be unsubstituted or substituted by a C1-6 alkyl, hydroxy or C3-10 cycloalkyl group or which may be fused to a benzene ring;(a) wherein the group R possesses a methylene group in an .alpha.-position in relation to the 1- or 10- nitrogen atom, which comprises reducing the corresponding amide;(b) wherein R is a methylamino group, which comprises reducing an ??ter of the corresponding carboxyamino compound; (c) wherein R is a methylamino group, which comprises reductively methylating the corresponding primary amine;(d) wherein the 1- or 10- nitrogen atom of R is linked by a double bond to an aliphatic or araliphatic substituent, which comprises condensing the corresponding primary amine with an aldehyde or ketone;(e) wherein the product is 1,3,5-tris-(bornan-10-yl)-1,3,5-hexahydrotriazine, which comprises reacting 10bornanamine with formaldehyde;(f) wherein R is an aminomethyl group in which one of the hydrogen atoms on the methyl carbon atom is substituted, which comprises reducing the corresponding ketoxime;(g) wherein the 1- or 10- nitrogen atom of R bears a phenyl or substituted phenyl substituent, which comprises reacting the corresponding amine with a benzyne;(h) wherein the 1- or 10- nitrogen atom of R is monoor di- substituted by an aliphatic, cycloaliphatic or araliphatic group, which comprises reacting a corresponding primary or secondary amine with a compound of the formula R5X where R5 is an aliphatic, cyclaliphatic or araliphatic group and X is a readily eliminatable group;(i) wherein the 1- or 10- nitrogen atom of R forms part of a hydroxy-substituted heterocyclic ring which contains at least 3 carbon atoms, which comprise cyclisation of a compound as defined above in which the nitrogen of R is substituted by a hydroxyalkyl group carrying an eliminatable group, there being at least three carbon atoms between the nitrogen atom of the amino group and the readily eliminatable gro?p;(j) wherein R is an aminomethyl group in which the methyl group is substituted, which comprises reducing the corresponding substituted nitromethyl compound;(k) wherein the 1- or 10- nitrogen atom of R is substituted by an aminoacyl group (the amino group of which unsubstituted, or substituted by one or two alkyl groups, which comprises reacting a corresponding haloacyl compound with ammonia or a monoor dialkylamine;(1) wherein the 1- or 10- nitrogen atom of R forms part of a heterocyclic ring, which comprises reacting the corresponding unsubstituted amine with a compound XR7X where X is a readily eliminatable group and R7 is a divalent alkylene group (which may be interrupted by O or S) or a cyclic group bearing two monovalent alkylene groups; or(m) wherein the 1- or 10- nitrogen atom or R is substituted by an aliphatic or araliphatic group, which comprises reducing the corresponding compound in which the said nitrogen atom is linked to said group by a double bond. The products have been found to possess antiviral activity.
This invention relates to a process for the preparation of 7,7dimethyl-¢2,2,1!-bicycloheptanes having at the 1-positions a group R, and the physiologically acceptable salts thereof, wherein R is an amino or aminomethyl group possessing a basic nitrogen atom and is substituted at the amino nitrogen atom (via a single or double bond) and/or at the 10- carbon atom by one or more C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl groups, which may be unsubstituted or substituted by an amino, mono or dialkylamino,imino, hydroxy, thiol, an esterified or etherified hydroxy or thiol group or (when a basic nitrogen atom is also present on the group) an oxo group in an .alpha.-position in relation to the R nitrogen atom; a C3-8 cyclo-alkyl group; a monocyclic aralkyl, aralkenyl or aralkynyl group; a phenyl group or substituted phenyl group; a 5 or 6 membered heterocyclic aryl group; or wherein the nitrogen atom of R forms part of 4 to 8 membered heterocyclic ring which may be unsubstituted or substituted by a C1-6 alkyl, hydroxy or C3-10 cycloalkyl group or which may be fused to a benzene ring;(a) wherein the group R possesses a methylene group in an .alpha.-position in relation to the 1- or 10- nitrogen atom, which comprises reducing the corresponding amide;(b) wherein R is a methylamino group, which comprises reducing an ??ter of the corresponding carboxyamino compound; (c) wherein R is a methylamino group, which comprises reductively methylating the corresponding primary amine;(d) wherein the 1- or 10- nitrogen atom of R is linked by a double bond to an aliphatic or araliphatic substituent, which comprises condensing the corresponding primary amine with an aldehyde or ketone;(e) wherein the product is 1,3,5-tris-(bornan-10-yl)-1,3,5-hexahydrotriazine, which comprises reacting 10bornanamine with formaldehyde;(f) wherein R is an aminomethyl group in which one of the hydrogen atoms on the methyl carbon atom is substituted, which comprises reducing the corresponding ketoxime;(g) wherein the 1- or 10- nitrogen atom of R bears a phenyl or substituted phenyl substituent, which comprises reacting the corresponding amine with a benzyne;(h) wherein the 1- or 10- nitrogen atom of R is monoor di- substituted by an aliphatic, cycloaliphatic or araliphatic group, which comprises reacting a corresponding primary or secondary amine with a compound of the formula R5X where R5 is an aliphatic, cyclaliphatic or araliphatic group and X is a readily eliminatable group;(i) wherein the 1- or 10- nitrogen atom of R forms part of a hydroxy-substituted heterocyclic ring which contains at least 3 carbon atoms, which comprise cyclisation of a compound as defined above in which the nitrogen of R is substituted by a hydroxyalkyl group carrying an eliminatable group, there being at least three carbon atoms between the nitrogen atom of the amino group and the readily eliminatable gro?p;(j) wherein R is an aminomethyl group in which the methyl group is substituted, which comprises reducing the corresponding substituted nitromethyl compound;(k) wherein the 1- or 10- nitrogen atom of R is substituted by an aminoacyl group (the amino group of which unsubstituted, or substituted by one or two alkyl groups, which comprises reacting a corresponding haloacyl compound with ammonia or a monoor dialkylamine;(1) wherein the 1- or 10- nitrogen atom of R forms part of a heterocyclic ring, which comprises reacting the corresponding unsubstituted amine with a compound XR7X where X is a readily eliminatable group and R7 is a divalent alkylene group (which may be interrupted by O or S) or a cyclic group bearing two monovalent alkylene groups; or(m) wherein the 1- or 10- nitrogen atom or R is substituted by an aliphatic or araliphatic group, which comprises reducing the corresponding compound in which the said nitrogen atom is linked to said group by a double bond. The products have been found to possess antiviral activity.
[CA1064928A]