2-Lower alkyl-2 or 3-cephem-4-carboxylic acid derivatives

A compound of the formula:

• ##STR51## wherein R.sup.1 is 2,2-di(C.sub.1 -C.sub.6)alkyl-4-phenyl-5-oxoimidazolidin-1-yl or acylamino selected from the group consisting of (C.sub.1 -C.sub.16)alkanoylamino, (C.sub.3 -C.sub.6)alkenoylamino, (C.sub.3 -C.sub.6)alkynoylamino, (C.sub.3 -C.sub.8)cycloalkanecarbonylamino, (C.sub.3 -C.sub.8)cycloalkyl(C.sub.1 -C.sub.6)alkanoylamino, (C.sub.3 -C.sub.8)cycloalkadienecarbonylamino, (C.sub.3 -C.sub.8)cycloalkadienyl(C.sub.1 -C.sub.6)-alkanoylamino, (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkanoylamino, (C.sub.1 -C.sub.6)alkylthio(C.sub.1 -C.sub.6)alkanoylamino, (C.sub.2 -C.sub.6)alkenylthio(C.sub.1 -C.sub.6)alkanoylamino, (C.sub.3 -C.sub.8)cycloalkylthio(C.sub.1 -C.sub.6)alkanoylamino, (C.sub.3 -C.sub.8)cycloalkoxy(C.sub.1 -C.sub.6)alkanoylamino, (C.sub.3 -C.sub.8)cycloalkanedienyloxy(C.sub.1 -C.sub.6)alkanoylamino, (C.sub.3 -C.sub.8)cycloalkanedienylthio(C.sub.1 -C.sub.6)alkanoylamino, (C.sub.1 -C.sub.6)alkoxycarbonylamino, (C.sub.3 -C.sub.8)cycloalkyloxycarbonylamino, (C.sub.3 -C.sub.8)cycloalkanedienyloxycarbonylamino, phenylcarbamoylamino, benzoylamino, toluoylamino, naphthoylamino, .alpha.-methylnaphthoylamino, phthaloylamino, benzenesulfonylamino, tetrahydronaphthoylamino, indancarbonylamino, phenyl(C.sub.1 -C.sub.6)alkanoylamino, phenoxy(C.sub.1 -C.sub.6)alkanoylamino, phenoxycarbonylamino, phenyl(C.sub. 1 -C.sub.6)alkoxycarbonylamino, phenylthio(C.sub.1 -C.sub.6)alkanoylamino, phenylglyoxyloylamino, heterocyclic carbonylamino heterocyclic (C.sub.1 -C.sub.6)alkanoylamino, heterocyclic (C.sub.1 -C.sub.6)alkoxycarbonylamino, heterocyclic oxycarbonylamino, heterocyclic oxy(C.sub.1 -C.sub.6)alkanoylamino, heterocyclic thio(C.sub.1 -C.sub.6)alkanoylamino, wherein said heterocyclic moiety is selected from the group consisting of thienyl, benzothienyl, furyl, 2-pyranyl, 4-pyranyl, dihydropyranyl, pyrrolyl, 2(or 3)H-pyrrolyl, 2(or 3)pyrrolinyl, imidazolyl, pyrazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, 1H-tetrazolyl, 2H-tetrazolyl, pyrrolidinyl, imidazolidinyl, piperidino, piperadinyl, indolyl, isoindolyl, indolizinyl, benzimidazolyl, quinolyl, isoquinolyl, 1(or 2)H-indazolyl, 1H(or 2)H-benzotriazolyl, oxazolyl, isoxazolyl, oxadiazolyl, sydnonyl, thiazolyl, 2,3-dihydrothiazolyl, thiadiazolyl, benzoxazolyl, benzoxadiazolyl, benzothiazolyl and benzothiadiazolyl, the above recited acylamino group having from 1 to 10 of the substituents selected from the group consisting of (C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, (C.sub.3 -C.sub.8)cycloalkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio, phenyl xylyl, tolyl, indanyl, phenyl(C.sub.1 -C.sub.6)alkyl, halogen, halophenyl, halophenoxy, cyano, (C.sub.1 -C.sub.6)alkylsulfinyl, (C.sub.1 -C.sub.6)alkanesulfonyl, (C.sub.1 -C.sub.6)alkoxycarbonyl(C.sub.1 -C.sub.6)alkoxy, nitro, sulfo, amino, azido, mercapto, carboxy, hydroxy, hydroxyamino, and mono- or di-di-(C.sub.1 -C.sub.6)alkylamino, imino, and carboxy(C.sub.1 -C.sub.6)alkoxy, and the above recited acylamino group having functional group selected from the grop consisting of amino, hydroxy, mercapto and carboxy, wherein said amino group is protected by said acyl groups or a moiety selected from the group consisting of trityl, 2-nitrophenylthio, 2,4-dinitrophenylthio, 2-hydroxybenzylidene, 2-hydroxy-5-chlorobenzylidene, 2-hydroxy-1-naphthylmethylene, 3-hydroxy-4-pyridylmethylene, 1-methoxycarbonyl-2-propylidene, 1-ethoxycarbonyl-2-propylidene, 3-ethoxycarbonyl-2-butylidene, 1-acetyl-2-propylidene, 1-benzoyl-2-propylidene, 1-[N-(2-methoxyphenyl)carbamoyl]-2-propylidene, 1-[N-(4-methoxyphenyl)carbamoyl]-2-propylidene, 2-ethoxycarbonylcyclohexylidene, 2-ethoxycarbonylcyclopentylidene, 2-acetylcyclohexlidene, 3,3-dimethyl-5-oxocyclohexylidene and mono- or di-silyl;
• said hydroxy and mercapto groups are protected by one of said acyl groups or a moiety selected from the group consisting of benzyl, trityl, methoxymethyl, 2-nitrophenylthio and 2,4-dinitrophenylthio;
• and said carboxy group is protected by a moiety selected from the group consisting of (C.sub.1 -C.sub.6)alkyl ester, mono- or di- or tri-halo(C.sub.1 -C.sub.6)alkyl ester, phenyl ester, nitrophenyl ester, indanyl ester, mono(or di or tri)phenyl(C.sub.1 -C.sub.6)alkyl ester, p-nitrobenzyl ester, p-bromobenzyl ester and tri(C.sub.1 -C.sub.6)alkylsilyl ester;
• R.sup.2 is carboxy or a protected carboxy selected from the group consisting of tri(C.sub.1 -C.sub.6)alkylsilyl ester, (C.sub.1 -C.sub.16)alkyl ester, (C.sub.2 -C.sub.6)alkenyl ester, (C.sub.2 -C.sub.6)alkynyl ester, (C.sub.3 -C.sub.8)cycloalkyl ester, (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl ester, (C.sub.1 -C.sub.6)alkylthio(C.sub.1 -C.sub.6)alkyl ester, di(C.sub.1 -C.sub.6)-alkylamino ester, (C.sub.1 -C.sub.6)alkylideneamino ester, (C.sub.1 -C.sub.6)alkylsulfenyl(C.sub.1 -C.sub.6)alkyl ester, (C.sub.1 -C.sub.6)alkanoyloxy(C.sub.1 -C.sub.6)alkyl ester,) phenyl ester, xylyl ester, naphthyl ester, indanyl ester, dihydroanthryl ester, phenyl(C.sub.1 -C.sub.6)alkyl ester, phenoxy(C.sub.1 -C.sub.6)alkyl ester, phenylthio(C.sub.1 -C.sub.6)alkyl ester, phenylsulfenyl(C.sub.1 -C.sub.6)alkyl ester, benzoyl(C.sub.1 -C.sub.)alkyl ester, phthalimido ester, pyridyl ester, piperidino ester, 2-pyridon-1-yl ester, tetrahydropyranyl ester, quinolyl ester, pyrazolyl ester, heterocyclic (C.sub.1 -C.sub.6)alkyl ester wherein said heterocyclic moiety is selected from the group consisting of pyridyl, piperidino, 2-pyridon-1-yl, tetrahydropyranyl, quinolyl and pyrazolyl, the above recited ester having from 1 to 10 of the substituents selected from the group consisting of (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1 -C.sub.6)alkylsulfinyl, (C.sub.1 -C.sub.6)alkanesulfonyl, phenylazo, halogen, cyano and nitro;
• N-(C.sub.1 -C.sub.6)alkyl acid amide, N,N-di(C.sub.1 -C.sub.6)alkyl acid amide and acid amide formed with pyrazole, imidazole or 4-(C.sub.1 -C.sub.6)alkylimidazole, R.sup.3 is (C.sub.1 -C.sub.6)alkyl, and X is --S-- or ##STR52## or a pharmaceutically acceptable salt thereof.