Patent GB-1052346-A (GB)
IPC: C07D213/30
Abstract: 1,052,346. Pyridine derivatives. F. HOFFMANN-LA ROCHE & CO. A.G. Sept. 8, 1965 [Sept. 9, 1964], No. 38352/65. Headings C2C and C2J. Novel pyridine derivatives of general formula wherein the symbols R<SP>1</SP> and R<SP>2</SP> each represent an alkyl, halo-alkyl, alkenyl, alkynyl, aralkyl, aralkenyl, alkylene aliphatic ether, alkylene aryl ether, or alkylene aralkyl ether group, containing not more than 7 carbon atoms in the alkyl radical or 6-10 in the aryl radical, a five or six-membered heterocyclic group, a heterobicyclic group containing from seven to ten atoms in the heterocyclic nucleus, a cycloalkyl group containing from three to eight atoms, an amino, mono- and di-substituted amino (including acylamino), aminomethyl, alkylaminomethyl, dialkylaminomethyl, or disubstituted aminomethyl group in which the substituents together represent an alkylene, aza-alkylene, oxa-alkylene or thia-alkylene group and form with the nitrogen atom to which they are attached a five- or sixmembered heterocyclic group, an unsubstituted phenyl group or a phenyl group having at least one of the substituents amino, substituted amino, hydroxy, halo, trifluoromethyl, alkyl and alkoxy (provided that R<SP>1</SP> and R<SP>2</SP> cannot both represent an unsubstituted phenyl group) or R<SP>1</SP> and R<SP>2</SP> together with the carbon atom to which they are attached represent a cycloalkyl group containing from three to eight carbon atoms, an unsubstituted or lower alkyl substituted five to eight-membered heteromonocyclic group containing at least one nitrogen, sulphur and/or oxygen atom, a five to ten-membered heterobicyclic group containing at least one nitrogen, sulphur and/or oxygen atom, a xanthyl-(9), SH-dibenzo [a,d] cycloheptenyl-(5) or 10,11-dihydro-SH-dibenzo [a,d] cycloheptenyl-(5) group, and acid addition salts thereof, are prepared by reacting a [pyridyl - (4) - methyl] - (alkali metal) or -magnesium halide derivative with a ketone of general formula wherein R<SP>1</SP> and R<SP>2</SP> are as defined above and may be converted into the novel compounds of the general formulµ wherein R<SP>1</SP> and R<SP>2</SP> are as above and R<SP>10</SP> and R<SP>20</SP> have any of the values of R<SP>1</SP> and R<SP>2</SP> hereinbefore except lower-alkenyl, lower alkynyl, aralkenyl, by dehydration using methods known per se, and subsequent hydrogenation in the presence of a catalyst. Acid addition salts of all the novel compounds are referred to. 2 - Piperidino - acetophenone, 2 - morpholinoacetophenone and 2-(4-methyl-piperazino) acetophenone are prepared by reaction of 2-chloroacetophenone with the required free base, in ether. [[Pyridyl - (4)] - methyl] - lithium is prepared by reacting phenyl lithium and 4-methylpyridine. [Pyridyl-(4)].methyl magnesium bromide is prepared by reacting 4-methyl-pyridine and ethyl magnesium bromide. Pharmaceutical compositions having anticonvulsant activity and which may be administered orally, parenterally or rectally in the form of tablets, capsules, suppositories, dragees, solutions, emulsions or suspensions and contain a compound of any of the three general formula above, or an acid addition salt thereof, as the active ingredient.