3-ARYL-8-CARBAMOYLYNORTROPANES

• Main Author: GROVER CLEVELAND HELSLEY
• Format: Patent
• Language: English
• Published: 01.03.1973
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

1304649 Nortropane derivatives A H ROBINS CO Inc 12 Aug 1971 [31 Aug 1970] 37953/71 Heading C2C Novel 3α- and 3#-arylnortropane derivatives of the formula wherein R1 is H, C 1-8 alkyl, phenyl, trifluoromethylphenyl or C 1-8 alkoxyphenyl and R2 is H, CF 3 , C 1-8 alkyl or C 1-8 alkoxy are prepared by reacting the corresponding 3α- or 3#-phenyl- (or monosubstituted phenyl) nortropane with nitrourea, or isocyanates of the formula R3NCO, in which R 3 is C 1-8 alkyl, phenyl, trifluoromethyl phenyl or C 1-8 alkoxyphenyl. 3α - Phenyl - (or R2 - phenyl) - nortropanes are obtained by hydrogenating the corresponding 3 - phenyl - (or R2 - phenyl) - nortropidines, made by dehydrating the appropriate 3-phenyl- (or R2-phenyl)-nortropanols resulting from the hydrogenolysis of the corresponding 8-benzyl-3- phenyl- (or R2-phenyl)-nortropanols, which are prepared by reacting the appropriate phenylmagnesium bromide with 8-benzyl-3-nortropanone. 3# - phenyl - (or R2 - phenyl) - nortropane are prepared from the corresponding 8-cyano-3#- phenyl - (or R2 - phenyl) - nortropanes, obtained by reacting cyanogen bromide with the appropriate 3#-phenyl-(or R2-phenyl}-tropane resulting from the treatment of the corresponding 3#- phenyl-(or R2-phenyl)-tropines with Raney nickel catalyst in lower alkanols. Pharmaceutical compositions suitable for oral administration, contain the above novel compounds in admixture with suitable carriers or diluents. The compounds possess anticonvulsive activity.