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AssigneePLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvo
InventorsNedjeljko Kujundzic, Dina Pavlovic, Gabrijela Kobrehel, Gorjana Lazarevski, Zeljko Kelneric
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The invention relates to 9-N-ethenyl derivatives of 9 (S)-erythromycylamine, new semisynthetic antibiotics of the macrolide class of the general formula (I) ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and represent nitryl, a carboxyl group of the formula COOR.sup.3, wherein R.sup.3 represents a C.sub.1 -C.sub.4 alkyl group, or a keto group of the formula COR.sup.4, wherein R.sup.4 represents a C.sub.1 -C.sub.4 alkyl group, to their pharmaceutically acceptable addition salts with inorganic or organic acids, to a process for their preparation, to a process for the preparation of the pharmaceutical compositions as well as to the use of the obtained pharmaceutical compositions in the treatment of bacterial infections.
9-N-Ethenyl derivatives of 9(S)-erythromycylamine of the general formula (I) ##STR6## wherein R.sup.1 and R.sup.2 are the same or different and represent nitryl, a carboxyl group of the formula COOR.sup.3, wherein R.sup.3 represents a C.sub.1 -C.sub.4 alkyl group, or a keto group of the formula COR.sup.4, wherein R.sup.4 represents a C.sub.1 -C.sub.4 alkyl group, and pharmaceutically acceptable addition salts thereof with inorganic or organic acids.
A process for the preparation of 9-N-Ethenyl derivatives of 9(S)-erythro-mycylamine of the formula (I) ##STR7## wherein R.sup.1 and R.sup.2 are the same or different and represent nitryl, a carboxy group of the formula COOR.sup.3, wherein R.sup.3 represents C.sub.1 -C.sub.4 alkyl group, or a keto group of the formula COR.sup.4, wherein R.sup.4 represents a C.sub.1 -C.sub.4 alkyl group, and of pharmaceutically acceptable addition salts thereof with inorganic or organic acids, wherein 9(S)-erythromycylarnine of the formula (II) ##STR8## is subjected to a reaction with ethoxyethylene derivatives of the formula (III) ##STR9## wherein R.sup.1 and R.sup.2 are the same or different and represent nitryl, a carboxyl group of the formula COOR.sup.3, wherein R.sup.3 represents a C.sub.1 -C.sub.4 alkyl group, or a keto group of the formula COR.sup.4, wherein R.sup.4 represents C.sub.1 -C.sub.4 alkyl group, in toluene, xylene or another aprotic solvent at a temperature from 20.degree. to 80.degree. C. and then, optimally to a reaction with inorganic or organic acids.
Dependencies are inferred from the claim text.