Organometallic derivatives of penicillin
OwnerEva Irene Edwards, Roger Epton +1inventors
InventorsEva Irene Edwards, Roger Epton, George Marr
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Abstract
This invention relates to a semi-synthetic penicillin having at least one .pi.-aromatic, organometallic complex of a transition metal such as ferrocene, attached, preferably in the 6 position, to a penicillin nucleus which optionally carries further substituents.
Claims17
A semi-synthetic penicillin of the formula:
- ##STR8## wherein:
- L is selected from the group consisting of ##STR9## n being an integer from 0 to 2, and each R.sub.1 and R.sub.2 are the same or different members of the group consisting of hydrogen, alkyl, aryl, alkaryl, aralkyl, alkoxy, --CHO, --COOH, --CH.sub.2 N(CH.sub.3).sub.2, --NH.sub.2, --C.sub.6 H.sub.5, --CH.sub.2 SH, --CH.sub.2 I, --CO--CH.sub.2 Z wherein Z is Cl, Br or I, --MeR.sub.3 wherein Me is Si, Ge or Sn and R is alkyl containing 1 to 3 carbon atoms, or R.sub.1 and R.sub.2 taken together form a cycloalkyl group;
- and M is selected from the group consisting of pi-bonded aromatic organometallic complexes of a transition metal represented by the formulae:
- ##STR10## X and Y being the same of different members of the group consisting of hydrogen, alkyl, aryl, aralkyl, alkaryl, --CHO, --COOH, --CH.sub.2 N(CH.sub.3).sub.2, --NH.sub.2, --C.sub.6 H.sub.5, --CH.sub.2 SH, --CH I or --CO--CH.sub.2 Z wherein Z is Cl, Br or I, --MeR.sub.3 wherein Me is defined as above, or another penicillin nucleus:
- ##STR11## L' represents a methylene linkage or --O--, and m is 0 or 1, or a pharmaceutically acceptable salt thereof.
6-(Ferrocenylcarboxamido)penicillanic acid.
6-(2-Ferrocenylacetamido)penicillanic acid.
6-(2-Ferrocenyl-2-methylacetamido)pencillanic acid.
6-(2-Ferrocenyl-2,2-dimethylacetamido)pencillanic acid.
6-(2-Ferrocenyl-2-methoxyacetamido)penicillanic acid.
6-(1-Ferrocenylcyclopropanecarboxamido)penicillanic acid.
6-[1-Phenyl-(o-ferrocenyl)carboxamido]penicillanic acid.
6-(2-Ferrocenyloxyacetamido)penicillanic acid.
1,1'-Bis(6-acetamidopenicillanic acid)ferrocene.
Dependencies are inferred from the claim text.