Patent IE-43575-B1 (IE)
Title: Erythromycin derivatives
IPC: C07H17/08
Filed: 1976-04-07
Abstract: 1528343 Erythromycylamine derivatives DR KARL THOMAE GmbH 6 April 1976 [7 April 1975 19 Feb 1976 (2)] 13943/76 Heading C2C [Also in Division A5] Novel erythromycylamine derivatives of the general formula wherein E is an erythromycyl group of the formula R 1 represents a hydrogen atom; an alkyl group containing from 1 to 3 carbon atoms; an alkoxyalkyl group (in which the alkylene moiety contains from 1 to 3 carbon atoms and the alkoxy moiety contains from 1 to 5 carbon atoms); a phenyl group or a benzyl group; R 2 represents a hydrogen atom; a hydroxyl group; an alkyl group containing from 1 to 3 carbon atoms or a phenyl group: R 3 represents an aliphatic acyloxy group containing from 1 to 5 carbon atoms; a benzoyloxy group; an alkoxy group containing from 1 to 5 carbon atoms; an amino group, a monoalkylamino group, containing from 1 to 5 carbon atoms; a dialkylamino group containing a total of from 2 to 8 carbon atoms; a hydroxyalkylamino group containing from 1 to 4 carbon atoms; a di(hydroxyalkyl)- amino group containing a total of from 2 to 8 carbon atoms; a phenylalkylamino group (in which the alkylene moiety contains 1 or 2 carbon atoms) or phenylamino group (the phenyl moiety in said phenylalkylamino or phenylamino group being optionally substituted by one or more halogen atoms, hydroxy groups or alkyl or alkoxy groups containing from 1 to 3 carbon atoms); an aliphatic acylamino group containing from 1 to 5 carbon atoms (optionally substituted by a phenyl group which may be substituted by halogen atoms); a benzoylamino group (in which the phenyl moiety is optionally substituted by a methoxy or carboxyl group or by one or two halogen atoms); a p-tolylsulphonamido group; a hydrazino group of formula -NH-NXY [in which X and Y, which may be the same or different, each represents a hydrogen atom, a phenyl group or an alkyl group containing from 1 to 3 carbon atoms, or, together with the nitrogen atom to which they are attached, represent a monoheterocyclic ring optionally interrupted by an oxygen or sulphur atom or by a further nitrogen atom (optionally substituted by an alkyl group containing from 1 to 5 carbon atoms)]; a group of formula -N = CR 4 R 5 [in which R 4 represents an amino group, a monoalkylamino group containing from 1 to 8 carbon atoms, a dialkylamino group containing a total of from 2 to 6 carbon atoms, a cyclohexylamino group, an N-alkyl-cyclohexylamino group (in which the alkyl moiety contains from 1 to 3 carbon atoms), a dicyclohexylamino group, a methoxyalkylamino group (in which the alkylene moiety contains from 1 to 3 carbon atoms), a di(methoxyalkyl)amino group (in which the alkylene moiety contains from 1 to 3 carbon atoms), a benzyl- or phenylethyl-amino group (in either of which the phenyl moiety is optionally substituted by from one to three alkoxy groups each of which may contain from 1 to 3 carbon atoms), a dibenzyl- or di(phenylethyl)-amino group, a benzhydrylamino group, an N-methyl-benzylamino group, an N-phenyl-benzylamino group, an N-methyl-phenylamino group or an N-ethylphenylamino group; or a piperidino, pyrrolidino, morpholino, piperazino, hexamethyleneimino, thiomorpholino or heptamethyleneimino group (optionally substituted by a methyl or benzyl group); and R 5 represents an amino or cyclohexylamino group, a dialkylamino group containing a total of from 2 to 6 carbon atoms, a benzylamino, phenylethylamino, dibenzylamino, phenoxymethylamino or phenoxyethylamino group, an N-phenyl-benzylamino group, an N-methyl-phenylamino group; or a piperidino, pyrrolidino, morpholino, piperazino, thiomorpholino or hexamethyleneimino group (optionally substituted by a benzyl group), a hydrogen atom, an alkyl group containing from 1 to 3 carbon atoms, a cyclohexyl group, a benzyl or phenylethyl group, a phenyl group (optionally substituted by a methoxy group), a thienyl, furyl or pyridyl group, an alkylthio group containing from 1 to 3 carbon atoms (optionally substituted by a methoxy or cyano group), or a benzylthio or phenylthio group (in either of which the phenyl moiety is optionally substituted by a methyl group)]; an alkoxyalkylamino, dialkylaminoalkylamino or alkoxycarbonylalkylamino group (in which the alkyl moiety or each alkyl moiety contains from 1 to 3 carbon atoms and the alkylene moiety contains from 1 to 4 carbon atoms); a thiazolylamino group or a pyridylamino group; or may, when n is 0, also represent a hydroxy group: and n is 0 or 1; and acid addition salts thereof are prepared by standard methods. Nitro compounds of the general formula O 2 N-CHR 2 -CHR 1 -NH-E are prepared by reacting erythromycylamine with Carbonyl compounds of the general formula O = CR 2 -CR 1 = NE are prepared by condensing erythromycylamine with O = CR 2 -CR 1 = O. Erythromycylamine and diacetylmonophenylimine are reacted to form a diimine of formula phenyl-N = C(CH 3 )-C(CH 3 ) = N-E. Diimines of the general formula (R 7 is a hydrogen atom or alkyl, hydroxyalkyl, phenylalkyl, phenyl, -NXY, alkoxyalkyl, dialkylaminoalkyl, alkoxycarbonylalkyl, thiazolyl or pyridyl group) are prepared by reacting R 7 -NH 2 with O = CR 2 -CR 1 = N-E. N - (2 - Phenylhydrazono - ethylidene)- erythromycylamine is prepared by reacting glyoxal monophenylhydrazone with erythromycylamine. The N-(2-methylphenylhydrazonoethylidene) derivative is prepared analogously. Hydrazones of the general formula are prepared by reacting YXN-NH 2 with O=CR 2 -CR 1 =NE.