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US 4,048,306 AGranted
Aldehyde-erythromycylamine condensation products
AssigneeBoehringer Ingelheim GmbH
InventorsRoland Maier, Eberhard Woitun, Bernd Wetzel, Wolfgang Reuter, Hanns Goeth, Uwe Lechner
Life of this patent
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Abstract
The invention relates to novel erythromycin derivatives, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as the salts are useful as antibacterials.
Claims13
An erythromycylamine-aldehyde condensation product of the formula ##STR12## wherein R is hydroxyl;
- phenoxy;
- phenyl-(alkoxy of 1 to 3 carbon atoms);
- alkoxy of 1 to 4 carbon atoms;
- hydroxy-(alkoxy of 1 to 4 carbon atoms);
- (alkoxy of 1 to 3 carbon atoms)-(alkoxy of 1 to 4 carbon atoms);
- di(alkyl of 1 to 3 carbon atoms)amino-(alkoxy of 1 to 4 carbon atoms);
- (alkoxy of 1 to 3 carbon atoms)-carbonyl(alkoxy of 1 to 4 carbon atoms);
- mercapto;
- phenyl-mercapto, where the phenyl moiety is unsubstituted or methyl-, methoxy-, ethoxy-, isopropoxy- or propoxy-substituted;
- phenyl-(alkyl of 1 to 3 carbon atoms)-mercapto;
- (straight or branched alkyl of 1 to 5 carbon atoms)-mercapto;
- cyclohexyl-mercapto;
- hydroxy-(alkyl of 1 to 3 carbon atoms)-mercapto;
- di(alkyl of 1 to 3 carbon atoms)amino-(alkyl of 1 to 3 carbon atoms)-mercapto;
- (alkoxy of 1 to 3 carbon atoms)-carbonyl-(alkyl of 1 to 3 carbon atoms)-mercapto;
- cyano-(alkyl of 1 to 3 carbon atoms)-mercapto;
- --NR.sub.2 R.sub.3, where R.sub.2 and R.sub.3, which may be identical to or different from each other, are each hydrogen, phenyl, phenyl-(alkyl of 1 to 3 carbon atoms), alkyl of 1 to 4 carbon atoms or, together with each other and the nitrogen atom to which they are attached, a 5- to 6-membered monocyclic heterocyclic ring which may contain an oxygen, sulfur or additional nitrogen atom;
- ##STR13## where R.sub.4 is straight or branched alkyl of 1 to 5 carbon atoms, benzyl or phenyl;
- --NH--CO--R.sub.5, where R.sub.5 is straight or branched alkyl of 1 to 5 carbon atoms, mono- or dihalo-substituted-(alkyl of 1 to 5 carbon atoms), cyano-(alkyl of 1 to 5 carbon atoms), phenyl-(alkyl of 1 to 3 carbon atoms) where the phenyl moiety may be mono- or di- or trimethoxy- or mono- or di-halo-substituted and the alkyl moiety may be monohalo-substituted, phenoxy-(alkyl of 1 to 3 carbon atoms), phenyl-(alkenyl of 2 to 4 carbon atoms), phenyl or phenyl having one or more methyl, hydroxyl, methoxy, nitro or chloro substituents attached thereto;
- or R.sub.5 is pyridyl;
- furyl;
- fluoro-furyl;
- thienyl;
- N-phenyl-carbamoyl;
- ##STR14## where R.sub.6 and R.sub.7, which may be identical to or different from each other, are each methyl, ethyl, propyl or isopropyl;
- ##STR15## where R.sub.8 is straight or branched alkyl of 1 to 5 carbon atoms;
- --NH--SO.sub.2 --R.sub.9, where R.sub.9 is alkyl of 1 to 4 carbon atoms or phenyl or (alkyl of 1 to 3 carbon atoms)-phenyl;
- or --SO.sub.2 --R.sub.10, where R.sub.10 is alkyl of 1 to 3 carbon atoms or phenyl or (alkyl of 1 to 3 carbon atoms)-phenyl;
- or a non-toxic, pharmacologically acceptable acid addition salt thereof.
26 more elements
Dependencies are inferred from the claim text.