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US 3,941,774 AGranted
Aminoalkyl esters of penicillins
AssigneeBeecham Group Limited
InventorsJohn Peter Clayton, Kenneth David Hardy, Angela Wendy Capel Guest
Life of this patent
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Abstract
Novel substituted amino methyl esters of penicillins and cephalosporins for oral administration which are much better absorbed than the parent compounds.
Claims8
A compound of formula (I) or a pharmaceutically acceptable acid-addition salt thereof which contains a basic nitrogen atom:
- ##SPC13##
- wherein
- Y is alkyl of one to six carbon atoms, phenyl, benzyl, alkoxy of one to six carbon atoms, or benzyloxy;
- Z is alkyl of one to six carbon atoms, phenylbenzyl, alkoxy of one to six carbon atoms, cyclopentyl, cyclohexyl and phenyl, or Y+Z taken together are a 3-benzoxazolidine ring;
- R is phenylacetamido, 2- or 3-thienylacetamido, phenoxyacetamido, .alpha.-amino-phenylacetamido, .alpha.-amino-2- or 3-thienylacetamido, .alpha.-carboxyphenylacetamido, .alpha.-sulphophenyl-acetamido, .alpha.-azidophenylacetamido, .alpha.-guanidino-phenylacetamido, or N-tetrazolylacetamido, provided that:
- when Z is hydrogen, Y is alkoxy of one to six carbon atoms then R is not a group of formula (IV):
- ##EQU11## in which R.sub.1 is C.sub.2.sub.-7 alkyl, phenyl, or furyl.
4 more elements
A compound as claimed in claim 5 wherein Z is methyl.
A compound selected from the group consisting of:
- N-benzoylaminomethyl ester of penicillin G
- 3-benzoxazolidinone methyl ester of penicillin G
- N-acetylaminomethyl ester of penicillin G
- N propionylaminomethyl ester of penicillin G
- Benzoxazolidinone -3-methyl ester of ampicillin hydrochloride.
2 more elements
(N-Ethoxycarbonyl-N-methyl)amino-methyl ester of penicillin G.
(N-Acetyl-N-methyl)aminomethyl ester of penicillin G.
Dependencies are inferred from the claim text.