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US 4,643,987 AGranted
Modified glycopeptides
AssigneeEli Lilly and Company
InventorsRamakrishnan Nagarajan, Amelia A. Schabel
Life of this patent
Estimating the term…
Abstract
Novel aracyl glycopeptide derivatives of formula 1 and methods for their preparation from the glycopeptide antibiotics vancomycin, A51568A, A51568B, M43A and M43D, are provided. The new glycopeptide derivatives are useful antibacterial agents.
Claims24
A compound of the formula:
- ##STR20## wherein R and R.sup.1 are hydrogen or methyl;
- R.sup.2 is methyl or R.sup.3 ;
- R.sup.3 is hydrogen or an acyl group of the formula ##STR21## wherein Ar is a group selected from phenyl, cyclohexadienyl, cyclohexenyl, naphthyl, thienyl, furyl, thiazolyl or pyridinyl;
- A is divalent oxygen, sulfur, sulfinyl, or sulfonyl;
- A.sup.1 is A or --NH--;
- X is hydrogen, chloro, bromo, iodo, nitro, C.sub.1 -C.sub.3 -alkyl, hydroxy, C.sub.1 -C.sub.3 -alkoxy, mercapto, C.sub.1 -C.sub.3 -alkylthio, carbamoyl, C.sub.1 -C.sub.3 -alkylcarbamoyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkanoyl, carboxy, or R.sub.5 R.sub.6 N--;
- R.sup.4 is hydrogen, C.sub.1 -C.sub.18 -alkyl or C.sub.2 -C.sub.18 -alkenyl;
- R.sup.5 and R.sup.6 indepedently are hydrogen or C.sub.1 -C.sub.4 -alkyl, or
- R.sup.5 is hydrogen and R.sup.6 is an amino-protecting group;
- W is C.sub.1 -C.sub.10 -alkylene or C.sub.2 -C.sub.10 -alkenylene;
- n is 1 or 2;
- and
- m, p and q are 0 or 1,
- provided that:
- (1) the sum of the carbon atoms in the R.sup.4 and W groups cannot exceed 21;
- (2) when X is mercapto, A and A.sup.1 cannot be sulfinyl or sulfonyl;
- (3) when A and A.sup.1 are sulfinyl or sulfonyl, they must be in equal oxidation states;
- (4) at least one of R.sup.2 and R.sup.3 must be other than hydrogen;
- (5) if m=0, p must=0;
- and (6) when n is 2, R and R.sup.1 must be hydrogen;
- and its salts.
18 more elements
Dependencies are inferred from the claim text.