BENZYL AMINO CARBAMATE SUBSTITUTED PYRIDINES

• Format: Patent
• Language: English; Spanish
• Published: 16.07.1971
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

The invention comprises novel compounds of the Formula I wherein R1 and R2, which may be the same or different, are NH 2 , mon- or di-(C 1-6 alkyl) amino, or an amino group acylated by carbonic acid, an aliphatic carbonic acid monoester having up to 6 C atoms in the ester group, an aromatic carbonic acid monoester, an optionally substituted benzoic acid, an optionally substituted saturated or unsaturated linear or branched C 1-6 aliphatic mono- or di-carboxylic acid, morpholine N-carboxylic acid or piperidine N-carboxylic acid R2 may also be H R3 is H, C 1-6 alkyl, or an acyl group derived from one of the acids indicated above in respect of the acylation of R1 and R2 R5, R6, R7, R8 and R9, which may be the same or different, are H, halogen, C 1-6 alkyl, CF 3 , OH, C 1-6 alkoxy, C 1-6 hydroxyalkyl, C 1-6 aliphatic acyl, COOH, or carboxy (C 1-6 alkyl) and R4 is H, C 1-6 alkyl or the group in which Alk is C 1-3 alkylene, optionally substituted by OH, C 1-6 alkyl, or C 1-6 alkoxy and R10, R11, R12, R13 and R14, which may be the same or different, have any of the meanings indicated above in respect of R5 to R9 except where Alk is C 1-3 unsubstituted alkylene, no more than four of the radicals R10 to R14 may be H and in addition if R4 is H or C 1-6 alkyl, no more than two of the radicals R5 to R9 may be H, their optically active and diastereomeric forms and their salts with pharmaceuticallyacceptable acids. These compounds are prepared by: (a) reducing the nitro groups or nitro groups in a compound of general Formula I above in which one or both of R1 and R2 are NO 2 to amino or amino groups (b) reacting at elevated temperatures the corresponding 2- (NHR3)-pyridine with a compound of the Formula III where Z is halogen, NHR3, or OR, where R is H, lower alkyl, or phenyl (c) condensing the appropriate 2-(NHR3)-pyridine with a compound of Formula IV above, under reducing conditions (d) reacting the corresponding 2- halopyridine, or 2-(lower alkoxy)-pyridine, or 2-phenoxypyridine, or 2-mesylpyridine, or pyridine-2-sulphonic acid or alkali metal salt thereof with a compound of the Formula VI above and, if desired or necessary, acylating any amino groups in the compounds thus obtained by the above methods. Pharmaceutical compositions, suitable for enteral, parenteral, oral, perlingual administration or in the form of sprays, contain the novel compounds or salts thereof in admixture with inert carriers or vehicles.