Method or producing naphthyridine compounds and novel...

Details Method or producing naphthyridine compounds and novel... Method or producing naphthyridine compounds and novel...

C - Chemistry, Metallurgy

07

D

C07D 471/04 (2006.01) C07D 211/84 (2006.01) C07D 213/26 (2006.01) C07D 213/61 (2006.01)

Patent

CA 2269984

An advantageous method of producing naphthyridine compounds of formulae (Ia) to (1c) wherein R means hydrogen or C1-C4 alkyl, Ar means possibly substituted phenyl, Hal means independently fluorine, chlorine or bromine, and n stands for 1, 2 or 3, whereby a halogenated nicotinic, isonicotinic or picolinic acid is made to react with an amino acrylic acid ester to obtain a halogenated 2- nicotinoyl-, isonicotinoyl- or picolinoyl-3-aminoacrylate which is made to react with an optionally substituted aniline to obtain a halogenated 2- nicotinoyl-, isonicotinoyl- or picolinoyl-3-aminoacrylate which contains an amino group corresponding to the optionally substituted aniline. The second halogenated 2-nicotinoyl-, isonicotinoyl- or picolinoyl-3-aminoacrylate is cyclized by adding an acid scavenger to a compound of formulae (Ia) to (Ic) with R = C1-C4 alkyl and, in the case of production of a compound of formulae (Ia) to (Ic) with R = H, the compound of the formulae (Ia) to (Ic) with R = C1- C4 alkyl is saponified.

Procédé avantageux de fabrication de composés de naphtyridine des formules (Ia) à (Ic) dans lesquelles R désigne un hydrogène ou un alkyle en C¿1?-C¿4?, Ar désigne un phényle éventuellement substitué, Hal désigne, indépendamment, un fluor, un chlore ou un brome, n est égal à 1, 2 ou 3, procédé consistant à faire réagir un chlorure d'acide nicotinique, isonicotinique ou picolinique avec un ester d'acide aminoacrylique, de manière à obtenir un 2-nicotinoyl- isonicotinoyl- ou picolinoyl-3-aminoacrylate halogéné, à faire réagir celui-ci avec une aniline éventuellement substituée, pour avoir un 2-nicotinoyl-, isonicotinoyl- ou picolinoyl-3-aminoacrylate renfermant un groupe amino correspondant à l'aniline éventuellement substituée, à cycliser ce deuxième aminoacrylate halogéné par addition d'un piègeur d'acide, en un composé des formules (Ia) à (Ic) avec R = alkyle en C¿1?-C¿4? et, dans le cas de la production d'un composé des formules (Ia) à (Ic) avec R = H, à saponifier le composé des formules (Ia) à (Ic) avec R = alkyle en C¿1?-C¿4?.

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