Tetracyclical derivatives from pyrimidine

Details Tetracyclical derivatives from pyrimidine Tetracyclical derivatives from pyrimidine

C - Chemistry, Metallurgy

07

D

C07D 513/14 (2006.01) A61K 31/54 (2006.01)

Patent

CA 2287298

The present invention relates to medicine, and especially to pharmacology, veterinary medicine, cosmetology and, more concretely, to synthetical biologically active compounds of a heterocyclical series having antimicrobial, antiviral, antichlamydia and immunostimulating effects: derivatives from 5-oxy- 5H-(1)benzopyrano-(5,6-b)-4-oxy-4H-(1,2)-pyrimido-1,4,5,6-tetrahydro-1,3- thiazine. It is characterized by the synthesis of the new class of heterocyclical compounds, i.e. derivatives from 5-oxy-5H-(1)benzopyrano-(5,6- b)-4-oxy-4H-(1,2)-pyrimido-1,4,5,6-tetrahydro-1,3-thiazine (1) of general formula (1); (1-X) where R1 is H or halogen; R2 is H or halogen or a nitro group or a hydroxy group or a metoxy group. The above-mentioned objective can be reached with R1=R2=H (I); R1=C1 (II); R1=R2=C2 (III); R1=H and R2=Br (IV); R1=R2=Br (V); R1=H and R2=NO2 (VII); R1=Br and R2=NO2 (VIII); R1=H and R2=OCN3 (IX); R1=H and R2=OH (X). The inventive synthesis of the substances concerned is a two-step processus: 1) synthesis of 5-oxy-5H-(1)benzopyrano-(5,6-b)-4-oxy- 4H-(1,2)-pyrimido-1,4,5,6-tetrahydro-1,3-thiazine (XI) from 2-thiobarbituric acid (XII) and 1,3-dihalogenpropane (XIII); 2) the compound concerned (1-X) is obtained from the intermediate substance produced during the first step and the derivative corresponding to salicylaldehyde (XIV).

La présente invention se rapporte à la médecine, et plus particulièrement à la pharmacologie, au secteur vétérinaire, à la cosmétologie, et de manière concrète à des composé synthétiques biologiquement actifs d'une série hétérocyclique ayant une action antimicrobienne, antivirale, antichlamydia et immunostimulante: aux dérivés de 5-oxy-5H-(1)benzopyrano-(5,6-b)-4-oxy-4H-(1,2)-pyrimido-1,4,5,6-tétrahydro-1,3-thiazine. L'aspect novateur réside dans la synthèse de la nouvelle classe de composés hétérocycliques, à savoir des dérivés de 5-oxy-5H-(1)benzopyrano-(5,6-b)-4-oxy-4H-(1,2)-pyrimido-1,4,5,6-tétrahydro-1,3-thiazine (1) de la formule générale (1); (1-X) où R1 est H ou halogène; R2 est H ou halogène ou un groupe nitro ou un groupe hydroxy ou un groupe métoxy. L'objectif recherché peut être atteint avec R1=R2=H I); R1=C1 (II); R1=R2=C1 (III); R1=H et R2=Br (IV); R1=R2=Br (V); R1=H et R2=NO2 (VII); R1=Br et R2=NO2 (VIII); R1=H et R2=OCH3 (IX); R1=H et R2=OH (X). La synthèse proposée des matières selon l'invention s'effectue en deux étapes: 1) on synthétise de la 5-oxy-5H-(1)benzopyrano-(5,6-b)-4-oxy-4H-(1,2)-pyrimido-1,4,5,6-tétrahydro-1,3-thiazine (XI) à base d'acide 2-thiobarbiturique (XII) et de 1,3-dihalogène-propane (XIII); 2) on obtient le composé en question (1-X) à partir de la substance intermédiaire obtenue au cours de la première étape et du dérivé correspondant d'aldéhyde salicylique (XIV).

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