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US 5,495,030 AGranted
9-[(substituted glycyl)amido)]-6-demethyl-6-deoxytetracyclines
AssigneeAmerican Cyanamid Company
InventorsPhaik-Eng Sum, Ving J. Lee, Raymond T. Testa
Life of this patent
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Abstract
The invention provides compounds of the formula: ##STR1## wherein R, R.sup.1 and Y are defined in the specification. The compounds are useful for the production of 6-demethyl-6-deoxytracycline derivatives.
Claims25
A compound of the formula:
- ##STR28## wherein:
- Y is selected from (CH.sub.2).sub.n X, n=0-5, X is halogen selected from bromine, chlorine, fluorine and iodine;
- R is selected from hydrogen;
- straight or branched (C.sub.1 -C.sub.8)alkyl group selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, heptyl and octyl;
- .alpha.-mercapto(C.sub.1 -C.sub.4)alkyl group selected from mercaptomethyl, .alpha.-mercaptoethyl, .alpha.-mercapto-1-methylethyl, .alpha.-mercaptopropyl and .alpha.-mercaptobutyl;
- .alpha.-hydroxy(C.sub.1 -C.sub.4)alkyl group selected from hydroxymethyl, .alpha.-hydroxyethyl, .alpha.-hydroxy-1-methylethyl, .alpha.-hydroxypropyl and .alpha.-hydroxybutyl;
- carboxyl(C.sub.1 -C.sub.8)alkyl group;
- (C.sub.6 -C.sub.10)aryl group selected from phenyl, .alpha.-naphthyl and .beta.-naphthyl;
- substituted(C.sub.6 -C.sub.10)aryl group wherein the substitution is selected from hydroxy, halogen, (C.sub.1 -C.sub.4)alkoxy, trihalo(C.sub.1 -C.sub.3) alkyl, nitro, amino, cyano, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.3)alkylamino and carboxy;
- (C.sub.7 -C.sub.9)aralkyl group selected from benzyl, 1-phenylethyl, 2-phenylethyl and phenylpropyl;
- substituted(C.sub.7 -C.sub.9)aralkyl group wherein the substitution selected from halo, (C.sub.1 -C.sub.4)alkyl, nitro, hydroxy, amino, mono- or di-substituted (C.sub.1 -C.sub.4)alkylamino, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkylsulfonyl, cyano and carboxy;
- R.sup.1 is selected from hydrogen and (C.sub.1 -C.sub.6)alkyl selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl and hexyl;
- when R does not equal R.sup.1 the stereochemistry of the asymmetric carbon (i.e. the carbon bearing the Y substituent) maybe be either the racemate (DL) or the individual enantiomers (L or D);
- or a pharmacologically acceptable organic or inorganic salt or metal complex thereof.
11 more elements
Dependencies are inferred from the claim text.