6"-(Substituted)-apramycin antibiotic derivatives and intermediates and starting materials therefor
AssigneeEli Lilly and Company
InventorHerbert A. Kirst
Life of this patent
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Abstract
Apramycin derivatives substituted at the 6"-position with a variety of substituents are claimed as broad spectrum antibiotics. Also claimed are starting materials and intermediates in the synthesis of the above apramycin derivatives.
Claims39
A compound of the formula ##STR16## wherein R.sub.1 is hydrogen, C.sub.1 to C.sub.3 -alkylsulfonyloxy, phenylsulfonyloxy, substituted phenylsulfonyloxy, tert-butyldimethylsilyloxy, fluoro, chloro, bromo, iodo, azido, amino, C.sub.1 to C.sub.3 -alkylthio, phenylthio, cyano or aminomethyl;
- and the pharmaceutically acceptable acid addition salts thereof.
A compound of the formula:
- ##STR17## wherein R.sub.2 is C.sub.1 to C.sub.3 -alkylsulfonyloxy, phenylsulfonyloxy, substituted phenylsulfonyloxy, azido, fluoro, bromo, iodo, C.sub.1 to C.sub.3 -alkylthio, phenylthio or cyano,
- R.sub.3 is benzyloxycarbonyl, C.sub.1 to C.sub.4 alkoxycarbonyl, trichloroethoxycarbonyl, formyl, trifluoroacetyl or phenoxycarbonyl and
- R.sub.4 and R.sub.4 ' are both methyl, or taken together form a cyclohexyl ring.
A compound of the formula ##STR18## wherein R.sub.4 and R.sub.4 ' are the same and are methyl or are taken together to form a cyclohexyl ring, R.sub.5 is chosen from the group consisting of hydrogen, a substituent of the formula ##STR19## or a substituent of the formula ##STR20## and R.sub.6 is chosen from the group consisting of benzyloxycarbonyl, trichloroethoxycarbonyl, formyl, trifluoroacetyl or phenoxycarbonyl;
- provided that, when R.sub.5 is a substituent of the formula ##STR21## R.sub.4 and R.sub.4 ' are methyl, and that, when R.sub.5 is a substituent of the formula ##STR22## R.sub.4 and R.sub.4 ' are taken together to form a cyclohexyl ring.
A compound of the formula ##STR24## wherein R.sub.7 is fluoro, chloro, bromo, iodo, cyano, C.sub.1 to C.sub.3 -alkylsulfonyloxy, phenylsulfonyloxy, substituted phenylsulfonyloxy, azido, C.sub.1 to C.sub.3 -alkylthio, phenylthio or tert-butyldimethylsilyloxy;
- and
- R.sub.8 is benzyloxycarbonyl, C.sub.1 to C.sub.4 -alkoxycarbonyl, trichloroethoxycarbonyl, formyl, trifluoroacetyl or phenoxycarbonyl.
A compound of the formula ##STR25## wherein R.sub.9 is benzyloxycarbonyl, trichloroethoxycarbonyl, formyl, trifluoroacetyl or phenoxycarbonyl.
Dependencies are inferred from the claim text.