Penicillanic acid dioxide prodrug
First Claim
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1. A compound of the formula ##STR5## wherein:
- R is hydrogen;
Q is chosen so that the compound hydrolyzes in vivo to 4.4-dioxopenicillanic and is selected from the group consisting ofN(R1) (R2) (R3) wherein R1, R2 and R3 are each alkyl having 1-4 carbon atoms, hydroxyalkyl having 1-4 carbon atoms, alkoxycarbonylalkyl wherein the alkyl has 1-4 carbon atoms and the alkoxy has 1-4 carbon atoms or aminocarbonylalkyl wherein the alkyl has 1-4 carbon atoms,N-alkyl-morpholyl wherein the alkyl has 1-4 carbon atoms, N-alkyl-piperidyl wherein the alkyl has 1-4 carbon atoms or N-alkyl-pyrrolidyl wherein the alkyl has 1-4 carbon atom, and those groups substituted at a ring position with alkyl having 1-4 carbon atoms, aminocarbonyl, hydroxyl or alkoxycarbonyl wherein the alkoxy has 1-4 carbon atoms,bicyclo [2.2.2]1-,4-diazaoctanyl and those substituted with alkyl having 1-4 carbon atoms, aminocarbonyl, hydroxyl or alkoxycarbonyl wherein the alkoxy has 1-4 carbon atoms,pyridyl, alkylpyridyl wherein the alkyl has 1-4 carbon atoms, dialkylpyridyl wherein each alkyl has 1-4 carbon atoms, trialkylpyridyl wherein each alkyl has 1-4 carbon atoms, halopyridyl, cyanopyridyl, nitropyridyl, aminocarbonylpyridyl, N-alkylaminocarbonylpyridyl wherein the alkyl has 1-4 carbon atoms, N,N-dialkylaminocarbonylpyridyl wherein each alkyl has 1-4 carbon atoms, alkoxycarbonylpyridyl wherein the alkoxy contains 1-4 carbon atoms, or N,N-dialkylaminopyridyl wherein each alkyl has 1-4 carbon atoms, andquinolyl or N-alkylimidazolyl wherein the alkyl has 1-4 carbon atoms; and
X- is a pharmaceutically-acceptable anion.
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Abstract
A compound of the formula ##STR1## is a prodrug of 4,4-dioxopenicillanic acid, wherein R is hydrogen or methyl; R1, R2 and R3 (a) when taken individually are each alkyl containing one to four carbon atoms, or (b) when taken together with the nitrogen to which they are attached form a five- or six-membered saturated monocyclic moiety, an eight-membered saturated bicyclic moiety or a five- or six-membered aromatic cyclic moiety annulated with zero, one or two fused benzene rings, with the proviso that any R1, R2 or R3 not part of a cyclic moiety is alkyl containing one to four carbon atoms; and X- is a pharmaceutically-acceptable anion. The prodrug can be included with a beta-lactam antibiotic in a pharmaceutical composition which can be employed in the treatment of infection in mammals. The above-described compounds hydrolyze in vivo to 4,4-dioxopenicillanic acid.
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Citations
13 Claims
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1. A compound of the formula ##STR5## wherein:
- R is hydrogen;
Q is chosen so that the compound hydrolyzes in vivo to 4.4-dioxopenicillanic and is selected from the group consisting of N(R1) (R2) (R3) wherein R1, R2 and R3 are each alkyl having 1-4 carbon atoms, hydroxyalkyl having 1-4 carbon atoms, alkoxycarbonylalkyl wherein the alkyl has 1-4 carbon atoms and the alkoxy has 1-4 carbon atoms or aminocarbonylalkyl wherein the alkyl has 1-4 carbon atoms, N-alkyl-morpholyl wherein the alkyl has 1-4 carbon atoms, N-alkyl-piperidyl wherein the alkyl has 1-4 carbon atoms or N-alkyl-pyrrolidyl wherein the alkyl has 1-4 carbon atom, and those groups substituted at a ring position with alkyl having 1-4 carbon atoms, aminocarbonyl, hydroxyl or alkoxycarbonyl wherein the alkoxy has 1-4 carbon atoms, bicyclo [2.2.2]1-,4-diazaoctanyl and those substituted with alkyl having 1-4 carbon atoms, aminocarbonyl, hydroxyl or alkoxycarbonyl wherein the alkoxy has 1-4 carbon atoms, pyridyl, alkylpyridyl wherein the alkyl has 1-4 carbon atoms, dialkylpyridyl wherein each alkyl has 1-4 carbon atoms, trialkylpyridyl wherein each alkyl has 1-4 carbon atoms, halopyridyl, cyanopyridyl, nitropyridyl, aminocarbonylpyridyl, N-alkylaminocarbonylpyridyl wherein the alkyl has 1-4 carbon atoms, N,N-dialkylaminocarbonylpyridyl wherein each alkyl has 1-4 carbon atoms, alkoxycarbonylpyridyl wherein the alkoxy contains 1-4 carbon atoms, or N,N-dialkylaminopyridyl wherein each alkyl has 1-4 carbon atoms, and quinolyl or N-alkylimidazolyl wherein the alkyl has 1-4 carbon atoms; and X- is a pharmaceutically-acceptable anion. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13)
- R is hydrogen;
Specification
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Current AssigneePfizer Inc.
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Original AssigneePfizer Inc.
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InventorsMyers, Robert F.
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Primary Examiner(s)Rizzo, Nicholas S.
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Application NumberUS06/381,104Time in Patent Office617 DaysField of Search260/245.2 R, 260/245.2 T, 424/270, 424/271, 424/114US Class Current424/114CPC Class CodesC07D 499/00 Heterocyclic compounds cont...
