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 Cx4-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.
Inventors
👤 Robert K. Blackwood
👤 Charles R. Stephens, Jr.
Bibliographic Details
Application Number—
JurisdictionUS
Data Sourcegoogle_patents
Last Synchronized2026-10-27 17:52
CPC Classifications
C; C07; C07C; C07C233/00
Claims Analysis
Total Claims: 3
Claim 1
Independent Claim
167 words
A compound selected from the group consisting of: ##STR16## the acid addition salts and the alkali metal and alkaline earth metal salts thereof and ##STR17## the alkali metal and alkaline earth metal salts thereof; wherein R 1 is selected from the group consisting of hydrogen, benzyl, phenethyl, cyclohexyl and alkyl of from 2 to 6 carbon atoms; R 2 is selected from the group consisting of hydrogen, alkyl of from 2 to 6 carbon atoms, and hydroxyalkyl of from 2 to 4 carbon atoms; Z is selected from the group consisting of hydrogen, chloro and fluoro; and R 3 is selected from the group consisting of OH, NHCONH 2 , NHC(NH)NH 2 , NHCSNH 2 , 4-(β-hydroxyethyl)piperazino, and NR 4 R 5 wherein R 4 is selected from the group consisting of hydrogen, alkyl of from 1 to 6 carbon atoms, phenyl, benzyl and cyclohexyl and R 5 is selected from the group consisting of hydrogen, alkyl of from 1 to 6 carbon atoms, phenyl and benzyl.
Claim 2
Dependent Claim
167 words
A compound selected from the group consisting of: ##STR16## the acid addition salts and the alkali metal and alkaline earth metal salts thereof and ##STR17## the alkali metal and alkaline earth metal salts thereof; wherein R 1 is selected from the group consisting of hydrogen, benzyl, phenethyl, cyclohexyl and alkyl of from 2 to 6 carbon atoms; R 2 is selected from the group consisting of hydrogen, alkyl of from 2 to 6 carbon atoms, and hydroxyalkyl of from 2 to 4 carbon atoms; Z is selected from the group consisting of hydrogen, chloro and fluoro; and R 3 is selected from the group consisting of OH, NHCONH 2 , NHC(NH)NH 2 , NHCSNH 2 , 4-(β-hydroxyethyl)piperazino, and NR 4 R 5 wherein R 4 is selected from the group consisting of hydrogen, alkyl of from 1 to 6 carbon atoms, phenyl, benzyl and cyclohexyl and R 5 is selected from the group consisting of hydrogen, alkyl of from 1 to 6 carbon atoms, phenyl and benzyl.
Claim 3
Dependent Claim
18 words
The compound of the first structural formula of claim 1 wherein R 1 and R 2 are hydrogen.