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US 4,698,327 AGranted
Novel glycopeptide derivatives
AssigneeEli Lilly and Company
InventorsRamakrishnan Nagarajan, Amelia A. Schabel
Life of this patent
Estimating the term…
Abstract
Novel glycopeptide antibiotics of formula (I) can be prepared from the glycopeptide antibiotics vancomycin, A51568A, A51568B, M43A and M43D by reaction with a ketone or aldehyde followed, if appropriate, by reduction. The new glycopeptide derivatives are useful antibacterial agents.
Claims20
A compound of formula (I):
- ##STR11## wherein R is hydrogen or methyl;
- n is 1 or 2;
- and
- (i) R.sub.1 is hydrogen or methyl;
- R.sub.2 and R.sub.3, independently, are hydrogen or a group of the formula:
- R.sub.6 R.sub.7 CH--;
- R.sub.6 and R.sub.7 are independently R.sub.5, R.sub.5 --(C.sub.1 -C.sub.5 -alkyl) or R.sub.5 --(C.sub.2 -C.sub.5 -alkenyl);
- R.sub.5 is hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.10 -cycloalkyl, C.sub.5 -C.sub.12 -cycloalkenyl, phenyl, naphththyl, indenyl, tetralinyl, decalinyl, adamantyl, a monocyclic heterocyclic ring system comprising 3 to 8 atoms in the ring or a bicyclic heterocyclic ring system comprising 6 to 11 atoms, provided that at least one atom of the ring system is carbon and at least one atom of the ring system is a heteroatom selected from O, N and S, and R.sub.5 may be substituted with one or more hydroxy, nitro, C.sub.1 -C.sub.10 -alkoxy, C.sub.1 -C.sub.10 alkyl, phenyl, C.sub.1 -C.sub.6 -alkylthio, nitrile, halo, C.sub.2 -C.sub.4 acylamino, amino, C.sub.1 -C.sub.4 dialkylamino groups;
- and
- R.sub.4 is hydrogen;
- or
- (ii) R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 together form a group of the formula ##STR12## provided that:
- (1) at least one of R.sub.2 and R.sub.3 must be other than hydrogen;
- (2) when n is 2, R must be hydrogen;
- (3) when R is methyl and R.sub.3 is hydrogen, R.sub.2 cannot be methyl and (4) when R and R.sub.1 are both methyl, then R.sub.2 is hydrogen or methyl and n is 1;
- or a salt thereof.
13 more elements
A compound of the formula:
- ##STR13## wherein R.sub.2a is hydrogen or methyl;
- R.sub.3a is R.sub.5 --(C.sub.1 -C.sub.6 -alkyl) or R.sub.5 --(C.sub.2 -C.sub.6 -alkenyl);
- and
- R.sub.4a is hydrogen;
- or
- R.sub.3a and R.sub.4a together form an R.sub.5 --(C.sub.1 -C.sub.6 -alkylidenyl) or R.sub.5 --(C.sub.2 -C.sub.6 -alkenylidenyl) group;
- R.sub.5 is hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.3 -C.sub.10 -cycloalkyl, C.sub.5 -C.sub.12 -cycloalkenyl, phenyl, napththyl, indenyl, tetralinyl, decalinyl, adamantyl, a monocyclic heterocyclic ring system comprising 3 to 8 atoms in the ring or a bicyclic heterocyclic ring system comprising 6 to 11 atoms, provided that at least one atom of the ring system is carbon and at least one atom of the ring system is a heteroatom selected from O, N and S, and R.sub.5 may be substituted with one or more hydroxy, nitro, C.sub.1 -C.sub.10 -alkoxy, C.sub.1 -C.sub.10 -alkyl, phenyl, C.sub.1 -C.sub.6 -alkylthio, nitrile, halo, C.sub.2 -C.sub.4 -acylamino, amino or C.sub.1 -C.sub.4 -dialkylamino groups;
- or salt thereof.
5 more elements
Dependencies are inferred from the claim text.