Novel 3,6-hemiketals from the class of 9a-azalides

Novel macrolide antibiotics (I) comprise 3,6-hemiketals of 9a-azalides. Macrolides of formula (I) and their addition salts with inorganic or organic acids are new. [Image] R1OH or L-cladinosyl of formula (a); R2H or silyl; R3H; R6OH; or R3+R6ether group; R4H, 1-4C acyl or COO(CH2)nAr; n : 1-7; Ar :...

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Bibliographic Details
Main Authors GORJANA LAZAREVSKI, GABRIJELA KOBREHEL, MLADEN VINKOVIC
Format Patent
LanguageEnglish
Published 12.12.2002
Edition7
Subjects
CHEMISTRY
DERIVATIVES THEREOF
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
NUCLEIC ACIDS
NUCLEOSIDES
NUCLEOTIDES
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS
SUGARS
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Summary:Novel macrolide antibiotics (I) comprise 3,6-hemiketals of 9a-azalides. Macrolides of formula (I) and their addition salts with inorganic or organic acids are new. [Image] R1OH or L-cladinosyl of formula (a); R2H or silyl; R3H; R6OH; or R3+R6ether group; R4H, 1-4C acyl or COO(CH2)nAr; n : 1-7; Ar : optionally substituted up to 18C aryl; R5H, Me or COO(CH2)nAr; R7, R8H, l-12C alkyl or silyl; or R7+R8cyclic carbonate. [Image] An independent claim is also included for the preparation of (I) from azithromycin. ACTIVITY : Antibacterial. 12-O-Methyl-azithromycin (Ia) exhibited MIC values (in mu g/ml) of 0.25, 0.12, 0.25, 1 and 0.5 against Staphylococcus aureus ATCC 6538 P, Micrococcus flavus ATCC 12228, Streptococcus faecalis ATCC 8043, Bacillus subtilis ATCC 11778 and Escherichia coli ATCC 10536 respectively. Corresponding values for azithromycin were (mu g/ml): 1, 0.25, 0.5, 0.5 and 1 respectively. MECHANISM OF ACTION : None given.
Bibliography:Application Number: AU19980093622