Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1976-09-03
1978-05-16
Demers, Arthur P.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
260552SC, 260554, 544380, C07C10319
Patent
active
040899004
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:
patent: 3183267 (1965-05-01), Blackwood et al.
patent: 3200149 (1965-08-01), Blackwood et al.
Blackwood et al., J. Am. Chem. Soc., 83, (1961), pp. 2773-2775.
Blackwood Robert K.
Stephens, Jr. Charles R.
Demers Arthur P.
Pfizer Inc.
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