Esters of antibiotic nodusmicin
AssigneeThe Upjohn Company
InventorsBarney J. Magerlein, Howard A. Whaley
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Abstract
Novel antibacterially-active esters of antibiotic nodusmicin. Activity is demonstrated against Staphylococcus aureus, Streptococcus pyogenes, and Sarcina lutea. Thus, these esters can be used in various known environments, using well-known procedures, to eradicate or control susceptible microbes.
Claims34
A compound of the formula ##STR3## wherein R is H in no more than two positions at the same time, a blocking group in at least one position, said blocking group selected from the group consisting of trisubstituted silyl ethers, substituted and unsubstituted tetrahydropyranyl ethers, .beta.,.beta.,.beta.-trichloroethyl ether, and carbonate esters, or a radical of the formula ##STR4## in no more than two positions at the same time, wherein X is selected from the group consisting of NH, S and O;
- R.sub.1, R.sub.2 and R.sub.3 are the same or different and are selected from the group consisting of H, OH, halogen, NO.sub.2, alkyl of 1 to 8 carbons, inclusive, NH.sub.2, NR.sub.4 R.sub.5, wherein R.sub.4 and R.sub.5 can be selected from the group consisting of H, OH, and alkyl and substituted alkyl, wherein the alkyl is from 1 to 8 carbon atoms, inclusive, and the substituent on substituted alkyl can be OH, halogen, and SH,;
- O- and S-alkyl, wherein alkyl is from 1 to 8 carbon atoms, inclusive;
- O acyl, and N acyl, wherein the acyl radical is a hydrocarbon carboxylic acid acyl of from 2 to 18 carbon atoms, inclusive;
- or a halo-, nitro-, hydroxy-, amino-, cyano-, thiocyano-, or loweralkoxy-substituted hydrocarbon acyl radical of from 2 to 18 carbon atoms, inclusive, excluding wherein X is N, R.sub.1 = R.sub.2 =R.sub.3 and H, and ##STR5## is on the 2 position of the molecule.
9-O-Thiophene-3-carbonyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9,11-O-Dithiophene-3-carbonyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9-O-2-Furoyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
11-O-2-Furoyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9,11-O-difuroyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9-O-Pyrrole-2-carbonyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9-O-N-Methylpyrrole-2-carbonyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9-O-5-Nitrofuroyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9-O-Thiophene-2-carbonyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9-O-5-Methylpyrrole-2-carbonyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9-O-5-Nitropyrrole-2-carbonyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
11-O-5-Nitropyrrole-2-carbonyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9-O-4-Nitropyrrole-2-carbonyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9-O-3-Furoyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9,11-O-Di-3-furoyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9-O-5-Bromofuroyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9,11-O-Di-5-bromofuroyl-18-O-butyldimethylsilyl ester of antibiotic nodusmicin.
9-O-Furoyl ester of antibiotic nodusmicin.
11-O-Furoyl ester of antibiotic nodusmicin.
18-O-Pyrrole-2-carbonyl ester of antibiotic nodusmicin.
9,18-O-Dipyrrole-2-carbonyl ester of antibiotic nodusmicin.
9,O-Thiophene-3-carbonyl ester of antibiotic nodusmicin.
9-O-N-Methyl-pyrrole-2-carbonyl ester of antibiotic nodusmicin.
9-O-Thiophene-2-carbonyl ester of antibiotic nodusmicin.
9-O-5-Nitrofuroyl ester of antibiotic nodusmicin.
9-O-5-Methylpyrrole-2-carbonyl ester of antibiotic nodusmicin.
9-O-5-Nitropyrrole-2-carbonyl ester of antibiotic nodusmicin.
9-O-4-Nitropyrrole-2-carbonyl ester of antibiotic nodusmicin.
9-O-3-Furoyl ester of antibiotic nodusmicin.
9-O-5-Bromofuroyl ester of antibiotic nodusmicin.
Dependencies are inferred from the claim text.