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filingDate 1971-11-11-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1974-06-16-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber ES-396915-A1
titleOfInvention A PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF 4-IMI-NO - 1,4 - DIHYDROPYRIDINE.
abstract Novel compounds of the Formula I in which the hetero substituent has the Formul[mu] II or III each of R1, R2, R4, R5 and R7 is H or C 1-3 alkyl and each of R3 and R6 is H, C 1-3 alkyl or phenyl, and their acid addition salts, are prepared generally by condensing an appropriate 4- aminopyridine with a 2-X-pyrimidine or 2-X- pyrazine in which X is halogen, sulpho, C 1-3 alkylthio, C 1-3 alkylsulphinyl, C 1-3 alkylsulphonyl, C 1-3 alkoxy, phenoxy, benzyloxy, tri - (C 1-3 alkyl) ammonium salt or nitro. They may also be prepared by (a) generation of the 4-imino substituent attached to the pyridine residue (b) formation of the pyridine ring, the pyrimidine ring, or both rings (c) aromatization by oxidation of dihydro up to dodecahydro derivatives (d) removal of extraneous groups attached to either or both of the heterocyolic rings (e) ring expansion to form the 1,4-dihydropyridine ring and (c) interchange of quaternary residues. Intermediates.-The following compounds are prepared in the examples: 2-fluoropyrimidine, 2 - methylsulphonylpyrimidine, 2 - methylsulphinylpyrimidine, 2 - pyrimidinyltrimethylammonium chloride, 2-nitropyrimidine, 1-(2- pyrimidinyl) - 4 - acetylimino - 1,4 - dihydropyrimidine, N - (4 - pyridyl) bromoformamidine, N - methyl - N1 - (4 - pyridyl) guanidine, 4 - pyridylacetamidine, 4 - (bemylideneamino)pyridine, 1 - (2 - pyrimidinyl) - 4 - carbamoyl - pyridinium chloride, 1 - (2 - pyrimidinyl) - 4 - oxo - 1,4 - dihydropyridine, 1 - (2- pyrimidinyl) - 4 - thio - 1,4 - dihydropyridine, 1 - (2 - pyrimidinyl) - 4 - chloropyridinium chloride, 1 - (2 - pyrimidinyl) - 4,4 - dimethoxy- 1,4 - dihydropyridine, 1 - (2 - pyrimidinyl) - 4- mercaptopyridinium chloride, 4 - methylsulphinylpyridine, N - amidino - 1,4 - dihydropyridin - 4 - one, 1 - amidino - 4 - chloropyridinium chloride, N - amidino - 4 - imino - 1,4- dihydropyridine, 3 - ketoglutaraldehyde tetraethylacetal, 3,31 - azino bis - (glutaraldehyde tetraethyl bis - acetal), 2 - chloro - 1,4,5,6 - tetra hydropyrimidine, 1 - [2 - (1,4,5,6 - tetrahydro)- pyrimidinyl] - 4 - imino - 1,4 - dihydropyridine 1 - (2 - pyrimidinyl) - 2,6 - dicarboxy - 4 - imino- 1,4 - dihydropyridine, 1 - (2 - pyrimidinyl) - 4- imino - tetrahydropyridine, 1 - (5 - carboxy - 2- pyrimidinyl) - 4 - imino - 1,4 - dihydropyridine, 3,31 - dithio bis (4 - ethoxycarbonylaminopyridine) 1 - (2 - pyrimidinyl) - 3 - mercapto - 4- imino - 1,4 - dihydropyridine, and 3,31 - dithiobis-(4-azido pyridine). Pharmaceutical compositions having hypoglycemic activity, for oral or parenteral administration, comprise a compound of Formula I, or a pharmacologically acceptable acid addition salt thereof, together with a pharmaceutical carrier.
priorityDate 1968-07-05-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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