7 -[D.alpha.-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-.alpha.-arylacetam ido]-3-(N,N-dimethyl-aminomethylpyridinium) methyl-3-cephem-4-carboxylates
AssigneeBristol-Myers Company
InventorsMasahisa Oka, Jun Okumura, Takayuki Naito
Life of this patent
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Abstract
7-[D-.alpha.-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-.alpha.-phenyl (and thienyl and substituted phenyl) acetamido]-3-(2-, 3- or 4-N,N-dimethylaminomethyl-pyridinium)methyl-3-cephem-4-carboxylates were synthesized and found to have potent antibacterial activity in vitro especially against many strains of Pseudomonas aeruginosa.
Claims26
A compound having the D-configuration in the 7-sidechain and the formula ##STR27## wherein Ar is ##STR28## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydrogen, hydroxy, methyl, methoxy or chloro and R.sup.3 is N,N-dimethylaminomethyl.
A compound having the D-configuration in the 7-sidechain and the formula ##STR29## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydrogen, hydroxy, methyl, methoxy or chloro and R.sup.3 is N,N-dimethylaminomethyl.
A compound having the D-configuration in the 7-sidechain and the formula ##STR30## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydrogen and R.sup.3 is N,N-dimethylaminomethyl.
A compound having the D-configuration in the 7-sidechain and the formula ##STR31## wherein Ar is ##STR32## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydrogen, hydroxy, methyl, methoxy or chloro and R.sup.3 is N,N-dimethylaminomethyl.
A compound having the D-configuration in the 7-sidechain and the formula ##STR33## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydrogen, hydroxy, methyl, methoxy or chloro and R.sup.3 is N,N-dimethylaminomethyl.
A compound having the D-configuration in the 7-sidechain and the formula ##STR34## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydrogen and R.sup.3 is N,N-dimethylaminomethyl.
A compound having the D-configuration in the 7-sidechain and the formula ##STR35## wherein Ar is ##STR36## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydrogen, hydroxy, methyl, methoxy or chloro and R.sup.3 is N,N-dimethylaminomethyl.
A compound having the D-configuration in the 7-sidechain and the formula ##STR37## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydrogen, hydroxy, methyl, methoxy or chloro and R.sup.3 is N,N-dimethylaminomethyl.
A compound having the D-configuration in the 7-sidechain and the formula ##STR38## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydrogen and R.sup.3 is N,N-dimethylaminomethyl.
A compound having the D-configuration in the 7-sidechain and the formula ##STR39## wherein Ar is ##STR40## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydrogen, hydroxy, methyl, methoxy or chloro and R.sup.3 is N,N-dimethylaminomethyl.
A compound having the D-configuration in the 7-sidechain and the formula ##STR41## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydrogen, hydroxy, methyl, methoxy or chloro and R.sup.3 is N,N-dimethylaminomethyl.
A compound having the D-configuration in the 7-sidechain and the formula ##STR42## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydrogen and R.sup.3 is N,N-dimethylaminomethyl.
7-[D-.alpha.-(4-Hydroxy- 1,5-naphthyridine-3-carboxamido)-.alpha.-phenylacetamido]-3-(3-N,N-dimethyl aminomethylpyridinium)methyl-3-cephem-4-carboxylate.
7-[D-.alpha.-(4-Hydroxy-1,5-naphthyridine-3-carb oxamido)-.alpha.-phenylacetamido]-3-(4-N,N-dimethylaminomethylpyridinium)me thyl-3-cephem-4-carboxylate.
7-[D-.alpha.-(4-Hydroxy- 1,5-naphthyridine-3-carboxamido)-.alpha.-(4-hydroxyphenyl)acetamido]-3-(3-N ,N-dimethylaminomethylpyridinium)methyl-3-cephem-4-carboxylate.
7-[D-.alpha.-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-.a lpha.-(4-hydroxyphenyl)acetamido]-3-(4-N,N-dimethylaminomethylpyridinium)me thyl-3-cephem-4-carboxylate.
7-[D-.alpha.-(4-Hydroxy- 1,5-naphthyridine-3-carboxamido)-.alpha.-(3,4-dihydroxyphenyl)acetamido]-3- (3-N,N-dimethylaminomethylpyridinium)methyl-3-cephem-4-carboxylate.
7-[D-.alpha.-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-.alpha .-(3,4-dihydroxyphenyl)acetamido]-3-(4-N,N-dimethylaminomethylpyridinium)me thyl-3-cephem-4-carboxylate.
7-[D-.alpha.-(4-Hydroxy- 1,5-naphthyridine-3-carboxamido)-.alpha.-(3-chloro-4-hydroxyphenyl)acetamid o]-3-(3-N,N-dimethylaminomethylpyridinium)methyl-3-cephem-4-carboxylate.
7-[D-.alpha.-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-.alpha.-(3-chl oro-4-hydroxyphenyl)acetamido]-3-(4-N,N-dimethylaminomethylpyridinium)methy l-3-cephem-4-carboxylate.
7-[D-.alpha.-(4-Hydro xy-1,5-naphthyridine-3-carboxamido)-.alpha.-(3-methyl-4-hydroxyphenyl)aceta mido]-3-(3-N,N-dimethylaminomethylpyridinium)methyl-3-cephem-4-carboxylate.
7-[D-.alpha.-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-.alpha.-(3-met hyl-4-hydroxyphenyl)acetamido]-3-(4-N,N-dimethylaminomethylpyridinium)methy l-3-cephem-4-carboxylate.
7-[D-.alpha.-(4-Hydro xy-1,5-naphthyridine-3-carboxamido)-.alpha.-(3-methoxy-4-hydroxyphenyl)acet amido]-3-(3-N,N-dimethylaminomethylpyridinium)methyl-3-cephem-4-carboxylate
7-[D-.alpha.-(4-Hydroxy-1,5-naphthyridine-3-carboxamdio)-.alpha.-(3-met hoxy-4-hydroxyphenyl)acetamido]-3-(4-N,N-dimethylaminomethylpyridinium)meth yl-3-cephem-4-carboxylate.
7-[D-.alpha.-(4-Hydrox y-1,5-naphthyridine-3-carboxamido)-.alpha.-(3-thienyl)acetamido]-3-(3-N,N-d imethylaminomethylpyridinium)methyl-3-cephem-4-carboxylate.
7-[D-.alpha.-(4-Hydroxy-1,5-naphthyridine-3-carboxamido )-.alpha.-(3-thienyl)acetamido]-3-(4-N,N-dimethylaminomethylpyridinium)meth yl-3-cephem-4-carboxylate.
Dependencies are inferred from the claim text.