4-Hydroxy-4-dedimethylamino-tetracyclines

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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260268PT, C07C10319

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active

040666948

ABSTRACT:
4-Dedimethylaminotetracyclines and the corresponding 5a,6-anhydro derivatives having an oxo, hydroxy, substituted imino, amino or substituted amino group other than dimethylamino at the C.multidot.4-position useful as antimicrobial agents. The 4-oxo-4-dedimethylaminotetracyclines are prepared by oxidation of tetracyclines with a hydrocarbon dicarboxylic acid haloimide and then converted by reduction to the corresponding 4-hydroxy compounds or by reaction with a primary amine to 4-substituted imino derivatives. The latter compounds are reduced to 4-amino derivatives which are reductively methylated or alkylated to 4-substituted-4-dedimethylaminotetracyclines. Dehydration of the tetracycline compounds affords the corresponding 5a,6-anhydro compounds.

REFERENCES:
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patent: 3030377 (1962-04-01), Soder et al.
patent: 3364260 (1968-01-01), Neidleman
patent: 3462487 (1969-08-01), Kinney et al.
patent: 3609188 (1971-09-01), Esse et al.

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