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Claims for Patent: RE40086

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Claims for Patent: RE40086

Title:Method for treating bacterial infection with novel 7-substituted-9-substituted amino 6-demethyl-6-deoxytetracyclines
Abstract:The disclosure is drawn to a method of using novel 7-substituted-9-(substituted amino)-6-demethyl-6-deoxytetracycline compounds to treat infections caused by a wide spectrum of bacterial organisms, including those which are resistant to tetracycline.
Inventor(s): Hlavka; Joseph J. (Tuxedo Park, NY), Sum; Phaik-Eng (Pomona, NY), Gluzman; Yakov (Upper Saddle River, NJ), Lee; Ving J. (Los Altos, CA), Ross; Adma A. (Airmont, NY)
Assignee: Wyeth Holdings Corporation (Madison, NJ)
Application Number:11/318,390
Patent Claims: 1. A method for the treatment or control of bacterial infections in warm-blooded animals which comprises administering to said animal a pharmacologically effective amount of a compound of the formula: ##STR00222## wherein: X is selected from amino, NR.sup.1R.sup.2, or halogen; the halogen is selected from bromine, chlorine, fluorine or iodine; R.sup.1 is selected from hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl and 1-methylpropyl; R.sup.2 is selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, and 1,1-dimethylethyl such that when X=NR.sup.1R.sup.2 and R.sup.1=hydrogen, R.sup.2=methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; and when R.sup.1=methyl or ethyl, R.sup.2=methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=n-propyl, R.sup.2=n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=1-methylethyl, R.sup.2=n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=n-butyl, R.sup.2=n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=1-methylpropyl, R.sup.2=2-methylpropyl; R is selected from R.sup.4(CH.sub.2).sub.nCO-- or R.sup.4' (CH.sub.2).sub.nSO.sub.2--; and n=0-4; and when R=R.sup.4(CH.sub.2).sub.n CO-- and .[.n-0.]. .Iadd.n=0.Iaddend., R.sup.4 is selected from hydrogen; amino; monosubstituted amino selected from straight or branched (C.sub.1-C.sub.6)alkylamino, cyclopropylamino, cyclobutylamino, benzylamino or phenylamino; disubstituted amino selected from dimethylamino, diethylamino, ethyl(1-methylethyl)amino, monomethylbenzylamino, piperidinyl, morpholinyl, 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl) or .[.4-(1,2,4triazolyl).]. .Iadd.4-(1,2,4-triazolyl).Iaddend.; straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C.sub.3-C.sub.6)cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6)cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3)acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, trihalo (C.sub.1-C.sub.3)-alkyl, nitro, amino, cyano, .[.(C.sub.1-C.sub.4)alkoxycarbonyl (C.sub.1-C.sub.3)alkylamino.]. (.Iadd.C.sub.1-C.sub.4)alkoxycarbonyl, .Iaddend.(.Iadd.C.sub.1-C.sub.3)alkylamino .Iaddend.or carboxy; (C.sub.7-C.sub.9) aralkyl selected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; .alpha.-amino-(C.sub.1-C.sub.4)alkyl selected from aminomethyl, .alpha.-aminoethyl, .alpha.-aminopropyl or .alpha.-aminobutyl; carboxy (C.sub.2-C.sub.4)-alkylamino selected from aminoacetic acid, .alpha.-aminobutyric acid or .alpha.-aminopropionic acid and the optical isomers thereof; (C.sub.7-C.sub.9)aralklamino; (C.sub.1-C.sub.4)alkoxycarbonylamino substituted (C.sub.1-C.sub.4) alkyl group; .alpha.-hydroxy(C.sub.1-C.sub.3)alkyl selected from hydroxymethyl, .alpha.-hydroxyethyl or .alpha.-hydroxy-1-methylethyl or .alpha.-hydroxypropyl; .alpha.-mercapto (C.sub.1-C.sub.3)alkyl selected from mercaptomethyl, .alpha.-mercaptoethyl, .alpha.-mercapto-1-methylethyl or .alpha.-mercaptopropyl; halo(C.sub.1-C.sub.3)alkyl group; a heterocycle selected from the group consisting of a five membered aromatic or saturated ring with one N, O, S or Se heteroatom optionally having a benzo or pyrido ring fused thereto, a five membered aromatic ring with two N, O, S, or Se heteroatoms optionally having a benzo or pyrido ring fused thereto, a six membered aromatic ring with one to three N, O, S or Se heteroatoms, or a six membered saturated ring with one or two N, O, S or Se heteroatoms and an adjacent appended O heteroatom; acyl or haloacyl group selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl; (C.sub.3-C.sub.6) .[.cycloalcylcarbonyl.]. .Iadd.cycloalkylcarbonyl.Iaddend., (C.sub.6-C.sub.10)aroyl selected from benzoyl or napthoyl; halo substituted (C.sub.6-C.sub.10)aroyl; (C.sub.1-C.sub.4) alkylbenzoyl, or (heterocycle)-carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxycarbonyl selected from methoxycarbonyl, ethoxycarbonyl, straight or branched .[.propoxylcarbonyl.]. .Iadd.propoxycarbonyl.Iaddend., straight or branched butoxycarbonyl or allyloxycarbonyl; vinyl or a substituted vinyl group with substitution selected from (C.sub.1-C.sub.3) alkyl, halogen, (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-napthyl, .beta.-naphthyl, halo(C.sub.1-C.sub.3)alkyl, or a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.3)alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.1-C.sub.4)alkoxy group; C.sub.6-aryloxy selected from phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1-C.sub.4) alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; (C.sub.7-C.sub.10)aralkyloxy; vinyloxy or a substituted vinyloxy group with substitution selected from (C.sub.1-C.sub.4)alkyl, cyano, carboxy, or (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; R.sup.aR.sup.bamino(C.sub.1-C.sub.4)alkoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, .[.1methylethyl.]. .Iadd.1-methylethyl.Iaddend., n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or .[.(CH.sub.2).sub.2 W(CH.sub.2).sub.2--.]. .Iadd.--(CH.sub.2).sub.2W(CH.sub.2).sub.2--.Iaddend. wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; or R.sup.aR.sup.baminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, or 1,1-dimethylethyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2 W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; and when R=R.sup.4 (CH.sub.2).sub.nCO-- and .[.n-1-4.]. .Iadd.n=1-4.Iaddend., R.sup.4 is selected from hydrogen; amino; straight or branched (C.sub.1-C.sub.4) alkyl group selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C.sub.3-C.sub.6)cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6)cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3)acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted(C.sub.6-C.sub.10)-aryl group with substitution selected from halo, (C.sub.1-C.sub.4)-alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.7-C.sub.10)aralkyl; acyloxy or haloacyloxy group selected from acetyl, propionyl, chloroacetyl, trichloroacetyl, (C.sub.3-C.sub.6) cycloalkylcarbonyl, (C.sub.6-C.sub.10)aroyl selected from benzoyl or naphthoyl, halo substituted (C.sub.6-C.sub.10)aroyl, (C.sub.1-C.sub.4)alkylbenzoyl, or (heterocycle)-carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxy; C.sub.6-aryloxy selected from phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1-C.sub.4)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; (C.sub.7-C.sub.10)aralkyloxy; (C.sub.1-C.sub.3)alkylthio group selected from methylthio, ethylthio, propylthio or allylthio; C.sub.6-arylthio group selected from phenylthio or substituted phenylthio with substitution selected from halo, (C.sub.1-C.sub.4)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; C.sub.6-arylsulfonyl group selected from phenylsulfonyl or substituted phenylsulfonyl with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, trihalo(C.sub.1-C.sub.3) alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3) alkylamino or carboxy; (C.sub.7-C.sub.8)aralkylthio group; a heterocycle as defined hereinabove; hydroxy; mercapto; mono- or di-straight or branched chain (C.sub.1-C.sub.6)-alkylamino with the alkyl selected from methyl, ethyl, n-propyl, 1-methyethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl; (C.sub.2-C.sub.5)azacycloalkyl group; a carboxy(C.sub.2-C.sub.4)alkylamino group with the carboxy alkyl selected from aminoacetic acid, .alpha.-aminopropionic acid, .alpha.-aminobutyric acid and the optical isomers thereof; .alpha.-hydroxy(C.sub.1-C.sub.3)alkyl selected from hydroxymethyl, .alpha.-hydroxyethyl or .alpha.-hydroxy-1-methyethyl or .alpha.-hydroxypropyl; halo(C.sub.1-C.sub.3)alkyl group; acyl or haloacyl selected from acetyl, propionyl, chloroacetyl, trifluroacetyl; (C.sub.3-C.sub.6) cycloalkylcarbonyl; (C.sub.6-C.sub.10)aroyl selected from benzoyl or naphthoyl; halo substituted (C.sub.6-C.sub.10)aroyl; (C.sub.1-C.sub.4)alkylbenzoyl, or (heterocycle)carbonyl, the heterocycle as defined hereinabove; .[.(C.sub.1-C.sub.4)alkoxycarbonylamino, group.]. .Iadd.(C.sub.1-C.sub.4)alkoxycarbonylamino group .Iaddend.selected from tert-butoxycarbonylamino, allyloxycarbonylamino, methoxycarbonylamino, ethoxycarbonylamino or propoxycarbonylamino; (C.sub.1-C.sub.4)alkoxycarbonyl group selected from methoxycarbonyl, ethoxycarbonyl, straight or branched propoxycarbonyl, allyloxycarbonyl or straight or branched butoxycarbonyl; R.sup.aR.sup.b-amino(C.sub.1-C.sub.4)alkoxy group wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is .[.(CH).sub.m.]. .Iadd.(CH.sub.2).sub.m.Iaddend., m=2-6 or --(CH.sub.2).sub.2 W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB, and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; or R.sup.aR.sup.baminoxy group, wherein R.sup.aR.sup.b is straight or branched (C.sub.1-C.sub.4)-alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)-alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl, and when R=R.sup.4' (CH.sub.2).sub.nSO.sub.2-- and n=0 R.sup.4' is selected from amino; monosubstituted amino selected from straight or branched (C.sub.1-C.sub.6)alkylamino, cyclopropylamino, cyclobutylamino, benzylamino or phenylamino; disubstituted amino selected from dimethylamino, diethylamino, ethyl(1-methylethyl)amino, monomethylbenzylamino, piperidinyl, morpholinyl, 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl) or 4-(1,2,4-triazolyl); straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C.sub.3-C.sub.6) cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6)cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3) acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, trihalo(C.sub.1-C.sub.3)-alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.7-C.sub.9)aralkyl; halo(C.sub.1-C.sub.3)alkyl group; a heterocycle as defined hereinabove; R.sup.aR.sup.b amino (C.sub.1-C.sub.4)alkoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)-alkyl selected from methyl, ethyl, n-propyl, 1-methyl-ethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W--(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)-alkyl; or R.sup.aR.sup.b aminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methyl-propyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2 W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3) alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3) alkyl; and when R=R.sup.4' (CH.sub.2).sub.nSO.sub.2-- and n=1-4, R.sup.4' is selected from hydrogen; straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, .[.1methylpropyl.]. .Iadd.1-methylpropyl.Iaddend., 2-methyl-propyl or 1,1-dimethylethyl; (C.sub.1-C.sub.4) carboxyalkyl; (C.sub.3-C.sub.6)cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6) cycloalkyl group with substitution selected from (C.sub.1-C.sub.3) alkyl, cyano, amino or (C.sub.1-C.sub.3)-acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, tri-halo(C.sub.1-C.sub.3) alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4) alkoxy-carbonyl, (C.sub.1-C.sub.3) alkylamino or carboxy; (C.sub.7-C.sub.9)aralkyl selected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; (C.sub.1-C.sub.4)alkoxy; C.sub.6-aryloxy selected from phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1-C.sub.3)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3) alkylamino; (C.sub.7-C.sub.10)aralkyloxy; R.sup.aR.sup.b amino (C.sub.1-C.sub.4) alkoxy wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)-alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2 W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, or .[.NOB.]. .Iadd.--NOB .Iaddend.and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; or R.sup.aR.sup.b aminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; (C.sub.1-C.sub.3) alkylthio selected from methylthio, ethylthio or n-propylthio; C.sub.6-arylthio selected from phenylthio or substituted phenylthio with substitution selected from halo, (C.sub.1-C.sub.3)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; (C.sub.7-C.sub.8) aralkylthio; a heterocycle as defined hereinabove; hydroxy; mercapto; mono- or di- straight or branched (C.sub.1-C.sub.6)alkyl- amino group .Iadd.with .Iaddend.the alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl; halo (C.sub.1-C.sub.3) alkyl; acyl or haloacyl selected from acetyl, propionyl, chloro-acetyl, trifluoroacetyl; (C.sub.3-C.sub.6) cycloalkylcarbonyl; (C.sub.6-C.sub.10) aroyl selected from benzoyl or naphthoyl; halo substituted (C.sub.6-C.sub.10)aroyl, (C.sub.1-C.sub.4) alkylbenzoyl, or (heterocycle) carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxycarbonyl selected from methoxycarbonyl, ethoxycarbonyl, straight or branched propoxycarbonyl, allyloxycarbonyl or straight or branched butoxycarbonyl;

R.sup.5 is selected from hydrogen; straight or branched (C.sub.1-C.sub.3) alkyl selected from methyl, .[.ethyl n-propyl.]. .Iadd.ethyl, n-propyl .Iaddend.or 1-methylethyl; (C.sub.6-C.sub.10) aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; (C.sub.7-C.sub.9) aralkyl group; a heterocycle as defined hereinabove; or --(CH.sub.2).sub.nCOOR.sup.7 where n=0-4 and R.sup.7 is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl group selected from methyl, ethyl, n-propyl or 1-methylethyl; or (C.sub.6-C.sub.10)aryl group selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; R.sup.6 is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl group selected .[.form.]. .Iadd.from .Iaddend.methyl, ethyl, n-propyl or 1-methylethyl; (C.sub.6-C.sub.10)aryl group selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; (C.sub.7-C.sub.9)-aralkyl group; a heterocycle as defined hereinabove; or --(CH.sub.2).sub.nCOOR.sup.7' where n=0-4 and R.sup.7' is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl selected from methyl, ethyl, n-propyl or 1-methylethyl; or (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; with the proviso that R.sup.5 and R.sup.6 cannot both be hydrogen; or R.sup.5 and R.sup.6 taken together are --(CH.sub.2).sub.2 W(CH.sub.2).sub.2-- wherein W is selected from (CH.sub.2).sub.q and q=0-1, --NH, .[.--N(C.sub.1-C.sub.3)--alkyl.]. .Iadd.--N(C.sub.1-C.sub.3)alkyl.Iaddend., --N(C.sub.1-C.sub.4) alkoxy, oxygen, sulfur or substituted congeners selected from (L or D)proline, ethyl(L or D)prolinate, morpholine, pyrrolidine or piperidine; and the pharmacologically acceptable organic and inorganic salts or metal complexes.

2. A method for the treatment or control of bacterial infections in warm-blooded animals caused by bacteria having the TetM and TetK resistant determinants which comprises administering to said animal a pharmacologically effective amount of a compound of the formula: ##STR00223## wherein: X is selected from amino, NR.sup.1R.sup.2 or halogen; the halogen is selected from bromine, chlorine, fluorine or iodine; .[.is.]. R.sup.1 is selected from hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl and 1-methylpropyl; R.sup.2 is selected from methyl, .[.ethyl n-propyl.]. .Iadd.ethyl, n-propyl.Iaddend., 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, and 1,1-dimethylethyl such that when X=NR.sup.1R.sup.2 and R.sup.1=hydrogen, R.sup.2=methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; and when R.sup.1=methyl or ethyl, R.sup.2=methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=n-propyl, R.sup.2=n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=1-methylethyl, R.sup.2=n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=n-butyl, R.sup.2=n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=1-methylpropyl, R.sup.2=2-methylpropyl; R is selected from R.sup.4(CH.sub.2).sub.nCO-- or R.sup.4' (CH.sub.2).sub.nSO.sub.2--; and n=0-4; and when R=R.sup.4(CH.sub.2).sub.n CO-- and .[.n-0.]. .Iadd.n=0.Iaddend., R.sup.4 is selected from hydrogen; amino; monosubstituted amino selected from straight or branched (C.sub.1-C.sub.6)alkylamino, cyclopropylamino, cyclobutylamino, benzylamino or phenylamino; disubstituted amino selected from dimethylamino, diethylamino, ethyl(1-methylethyl)amino, monomethylbenzylamino, piperidinyl, morpholinyl, 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl) or 4-(1,2,4-triazolyl); straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C.sub.3-C.sub.6)cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6)cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3)acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, .[.trihalo(C.sub.1-C.sub.3)--alkyl.]. .Iadd.trihalo(C.sub.1-C.sub.3)alkyl.Iaddend., nitro, amino, cyano, .[.(C.sub.1-C.sub.4)alkoxycarbonyl (C.sub.1-C.sub.3)alkylamino.]. (.Iadd.C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino .Iaddend.or carboxy; (C.sub.7-C.sub.9) aralkyl selected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; .alpha.-amino-(C.sub.1-C.sub.4)alkyl selected from aminomethyl, .alpha.-aminoethyl, .alpha.-aminopropyl or .alpha.-aminobutyl; carboxy (C.sub.2-C.sub.4)-alkylamino selected from aminoacetic acid, .alpha.-aminobutyric acid or .alpha.-aminopropionic acid and the optical isomers thereof; (C.sub.7-C.sub.9)aralkylamino; (C.sub.1-C.sub.4)alkoxycarbonylamino substituted (C.sub.1-C.sub.4) alkyl group; .alpha.-hydroxy(C.sub.1-C.sub.3)alkyl selected from hydromethyl, .alpha.-hydroxyethyl or .alpha.-hydroxy-1-methylethyl or .alpha.-hydroxypropyl; .alpha.-mercapto (C.sub.1-C.sub.3)alkyl selected from mercaptomethyl, .alpha.-mercaptoethyl, .alpha.-mercapto-1-methylethyl or .alpha.-mercaptopropyl; halo(C.sub.1-C.sub.3)alkyl group; a heterocycle selected from the group consisting of a five membered aromatic or saturated ring with one N, O, S or Se heteroatom optionally having a benzo or pyrido ring fused thereto, a five membered aromatic ring with two N, O, S, or Se heteroatoms optionally having a benzo or pyrido ring fused thereto, a six membered aromatic ring with one to three N, O, S or Se heteroatoms, or a six membered saturated ring with one or two N, O, S or Se heteroatoms and an adjacent appended O heteroatom; acyl or haloacyl group selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl; .[.(C.sub.3-C.sub.6) cycloalcylcarbonyl.]. (.Iadd.C.sub.3-C.sub.6)cycloalkylcarbonyl.Iaddend., (C.sub.6-C.sub.10)aroyl selected from benzoyl or naphthoyl; halo substituted (C.sub.6-C.sub.10)aroyl; (C.sub.1-C.sub.4) alkylbenzoyl, or (heterocycle)-carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxycarbonyl selected from methoxycarbonyl, ethoxycarbonyl, straight or branched .[.propoxylcarbonyl.]. .Iadd.propoxycarbonyl.Iaddend., straight or branched butoxycarbonyl or allyloxycarbonyl; vinyl or a substituted vinyl group with substitution selected from (C.sub.1-C.sub.3) alkyl, halogen, (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl, .beta.-naphthyl, halo(C.sub.1-C.sub.3)alkyl, or a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)-alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.1-C.sub.4)alkoxy group; C.sub.6-aryloxy selected from phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1-C.sub.4) alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; (C.sub.7-C.sub.10)aralkyloxy; vinyloxy or a substituted vinyloxy group with substitution selected from (C.sub.1-C.sub.4)alkyl, cyano, carboxy, or (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; R.sup.aR.sup.bamino(C.sub.1-C.sub.4)alkoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, .[.1methylethyl.]. .Iadd.1-methylethyl.Iaddend., n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or .[.(CH.sub.2).sub.2 W(CH.sub.2).sub.2--.]. .Iadd.--(CH.sub.2).sub.2 W(CH.sub.2).sub.2--.Iaddend. wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; or R.sup.aR.sup.b aminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, or 1,1-dimethylethyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2 W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, .[.O,S,.]. .Iadd.O, S, .Iaddend.--NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; and when R=R.sup.4 (CH.sub.2).sub.nCO-- and .[.n-1-4.]. .Iadd.n=1-4.Iaddend., R.sup.4 is selected from hydrogen; amino; straight or branched (C.sub.1-C.sub.4) alkyl group selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,.[.,.]. 1-methylpropyl, 2-methylpropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6)cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3)acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .[..beta.-naphyhyl.]. .Iadd..beta.-naphthyl.Iaddend.; a substituted(C.sub.6-C.sub.10)aryl group with substitution selected from halo, .[.(C.sub.1-C.sub.4)alkoxy.]. .Iadd.(C.sub.1-C.sub.4)alkoxy.Iaddend., trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.7-C.sub.10)aralkyl; acyloxy or haloacyloxy group selected from acetyl, propionyl, chloroacetyl, trichloroacetyl, (C.sub.3-C.sub.6) cycloalkylcarbonyl, (C.sub.6-C.sub.10)aroyl selected from benzoyl or naphthoyl, halo substituted (C.sub.6-C.sub.10)aroyl, (C.sub.1-C.sub.4)alkylbenzyl or (heterocycle)-carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxy; C.sub.6-aryloxy selected from phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1-C.sub.4)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; (C.sub.7-C.sub.10)aralkyloxy; (C.sub.1-C.sub.3)alkylthio group selected from methylthio, ethylthio, propylthio or allylthio; C.sub.6-arylthio group selected from phenylthio or substituted phenylthio with substitution selected from halo, (C.sub.1-C.sub.4)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; .[.C.sub.6-arylsulfinyl.]. .Iadd.C.sub.6-arylsulfonyl .Iaddend.group selected from phenylsulfonyl or substituted phenylsulfonyl with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3) alkylamino or carboxy; (C.sub.7-C.sub.8)aralkylthio group; a heterocycle as defined hereinabove; hydroxy; mercapto; mono- or di-straight or branched chain .[.(C.sub.1-C.sub.6)-alkylamino.]. .Iadd.(C.sub.1-C.sub.6)alkylamino .Iaddend.with the alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl; (C.sub.2-C.sub.5)azacycloalkyl group; a carboxy(C.sub.2-C.sub.4)alkylamino group with the carboxy alkyl selected from aminoacetic acid, .alpha.-aminopropionic acid, .alpha.-aminobutyric acid and the optical isomers thereof; .alpha.-hydroxy(C.sub.1-C.sub.3)alkyl selected from hydroxymethyl, .alpha.-hydroxyethyl or .alpha.-hydroxy-1-methylethyl or .alpha.-hydroxypropyl; halo(C.sub.1-C.sub.3)alkyl group; acyl or haloacyl selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl; (C.sub.3-C.sub.6) cycloalkylcarbonyl; (C.sub.6-C.sub.10)aroyl selected from benzoyl or naphthoyl; halo substituted (C.sub.6-C.sub.10)aroyl; (C.sub.1-C.sub.4)alkylbenzoyl, or (heterocycle)carbonyl, the heterocycle as defined hereinabove; .[.(C.sub.1-C.sub.4)alkoxycarbonylamino,.]. .Iadd.(C.sub.1-C.sub.4).Iaddend..Iadd.alkoxycarbonylamino .Iaddend. group selected from tert-butoxycarbonylamino, allyloxycarbonylamino, methoxycarbonylamino, ethoxycarbonylamino or propoxycarbonylamino; (C.sub.1-C.sub.4)alkoxycarbonyl group selected from methoxycarbonyl, ethoxycarbonyl, straight or branched propoxycarbonyl, allyloxycarbonyl or straight or branched butoxycarbonyl; R.sup.aR.sup.b-amino(C.sub.1-C.sub.4)alkoxy group wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is .[.(CH).sub.mm=2-6.]. .Iadd.(CH.sub.2).sub.m.Iaddend., .Iadd.m=2-6 .Iaddend. or .[.--(CH.sub.2).sub.2W(CH.sub.2).sub.2-wherein.]. .Iadd.--(CH.sub.2).sub.2W(CH.sub.2).sub.2--wherein .Iaddend.W is selected from --N(C.sub.1-C.sub.3)-alkyl, O, S, --NH, --NOB, and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; or R.sup.aR.sup.baminoxy group, wherein R.sup.aR.sup.b is straight or branched (C.sub.1-C.sub.4)-alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)-alkyl, .[.O,S,.]. .Iadd.O, S, .Iaddend.--NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl, and when R=R.sup.4' (CH.sub.2).sub.nSO.sub.2-- and n=0 R.sup.4' is selected from amino; monosubstituted amino selected from straight or branched (C.sub.1-C.sub.6)alkylamino, cyclopropylamino, cyclobutylamino, benzylamino or phenylamino; disubstituted amino selected from dimethylamino, diethylamino, ethyl(1-methylethyl)amino, monomethylbenzylamino, piperidinyl, morpholinyl, 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl) or 4-(1,2,4-triazolyl); straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C.sub.3-C.sub.6)cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6)cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3) acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .Iadd..alpha.-naphthyl .Iaddend.or .beta.-naphthyl .[..beta.-naphthyl or B-naphthyl.]. ; a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.7-C.sub.9)aralkyl; halo(C.sub.1-C.sub.3)alkyl group; a heterocycle as defined hereinabove; R.sup.aR.sup.b amino (C.sub.1-C.sub.4)alkoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)-alkyl selected from methyl, ethyl, n-propyl, 1-methyl-ethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W--(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)-alkyl; or R.sup.aR.sup.b aminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methyl-propyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3) alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3) alkyl; and when R=R.sup.4' (CH.sub.2).sub.nSO.sub.2-- and n=1-4, R.sup.4' is selected from hydrogen; straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methyl-propyl or 1,1-dimethylethyl; (C.sub.1-C.sub.4) carboxyalkyl; (C.sub.3-C.sub.6)cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6) cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3)-acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, tri-halo(C.sub.1-C.sub.3) alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxy-carbonyl, (C.sub.1-C.sub.3) alkylamino or carboxy; (C.sub.7-C.sub.9)aralkyl selected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; (C.sub.1-C.sub.4)alkoxy; C.sub.6-aryloxy selected from phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1-C.sub.3)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3) alkylamino; (C.sub.7-C.sub.10)aralkyloxy; R.sup.aR.sup.b amino (C.sub.1-C.sub.4) alkoxy, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)-alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, or .[.NOB.]. .Iadd.--NOB .Iaddend.and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; or R.sup.aR.sup.b aminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; (C.sub.1-C.sub.3) alkylthio selected from methylthio, ethylthio or n-propylthio; C.sub.6-arylthio selected from phenylthio or substituted phenylthio with substitution selected from halo, (C.sub.1-C.sub.3)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; (C.sub.7-C.sub.8) aralkythio; a heterocycle as defined hereinabove; hydroxy; mercapto; mono- or di-straight or branched (C.sub.1-C.sub.6)alkyl- amino group .Iadd.with .Iaddend.the alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl; halo (C.sub.1-C.sub.3) alkyl; acyl or haloacyl selected from acetyl, propionyl, chloro-acetyl, trifluoroacetyl; (C.sub.3-C.sub.6) cycloalkylcarbonyl; (C.sub.6-C.sub.10) aroyl selected

from benzoyl or naphthoyl; halo substituted (C.sub.6-C.sub.10)aroyl, (C.sub.1-C.sub.4)alkylbenzoyl, or (heterocycle) carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxycarbonyl selected from methoxycarbonyl, ethoxycarbonyl, straight or branched propoxycarbonyl, allyloxycarbonyl or straight or branched butoxycarbonyl; R.sup.5 is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl selected from methyl, .[.ethyl.]. .Iadd.ethyl, .Iaddend.n-propyl or 1-methylethyl; (C.sub.6-C.sub.10) aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; (C.sub.7-C.sub.9) aralkyl group; a heterocycle as defined hereinabove; or --(CH.sub.2).sub.nCOOR.sup.7 where n=0-4 and R.sup.7 is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl group selected from methyl, ethyl, n-propyl or 1-methylethyl; or (C.sub.6-C.sub.10)aryl group selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; R.sup.6 is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl group selected .[.form.]. .Iadd.from .Iaddend.methyl, ethyl, n-propyl, or 1-methylethyl; (C.sub.6-C.sub.10)aryl group selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; (C.sub.7-C.sub.9)-aralkyl group; a heterocycle as defined hereinabove; or --(CH.sub.2).sub.nCOOR.sup.7' where n=0-4 and R.sup.7' is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl selected from methyl, ethyl, n-propyl or 1-methylethyl; or (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; with the proviso that R.sup.5 and R.sup.6 cannot both be hydrogen; or R.sup.5 and R.sup.6 taken together are --(CH.sub.2).sub.2W(CH.sub.2).sub.2--, wherein W is selected from (CH.sub.2).sub.q and q=0-1, --NH, --N(C.sub.1-C.sub.3)-alkyl, --N(C.sub.1-C.sub.4) alkoxy, oxygen, sulfur or substituted congeners selected from (L or D)proline, ethyl(L or D)prolinate, morpholine, pyrrolidine or piperidine; and the pharmacologically acceptable organic and inorganic salts or metal complexes.

.Iadd.3. A method for the treatment or control of bacterial infections in warm-blooded animals which comprises administering to said animal a pharmacologically effective amount of a compound of the formula: ##STR00224## wherein: X is selected from amino, NR.sup.1R.sup.2 or halogen; the halogen is selected from bromine, chlorine, fluorine or iodine; R.sup.1 is selected from hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl and 1-methylpropyl; R.sup.2 is selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, and 1,1-dimethylethyl such that when X=NR.sup.1R.sup.2 and R.sup.1=hydrogen, R.sup.2=methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; and when R.sup.1=methyl or ethyl, R.sup.2=methyl, ethyl, n-propyl, 1-methylethyl, n-methylpropyl or 2-methylpropyl; and when R.sup.1=n-propyl, R.sup.2=n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=1-methylethyl, R.sup.2=n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=n-butyl; R.sup.2=n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=1-methylpropyl, R.sup.2=2-methylpropyl; R is selected from R.sup.4(CH.sub.2).sub.nCO-- or R.sup.4' (CH.sub.2).sub.nSO.sub.2--; and n=0-4; and when R=R.sup.4(CH.sub.2).sub.n CO-- and n=0, R.sup.4 is selected from hydrogen; amino; monosubstituted amino selected from straight or branched (C.sub.1-C.sub.6)alkylamino, cyclopropylamino, cyclobutylamino, benzylamino or phenylamino; disubstituted amino selected from dimethylamino, diethylamino, ethyl(1-methylethyl)amino, monomethylbenzylamino, piperidinyl, morphonlinyl, 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl) or 4-(1,2,4-triazolyl); straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C.sub.3-C.sub.6)cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6)cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3)acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4) alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.7-C.sub.9) aralkyl selected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; .alpha.-amino-(C.sub.1-C.sub.4)alkyl selected from aminomethyl, .alpha.-aminoethyl, .alpha.-aminopropyl or .alpha.-aminobutyl; carboxy (C.sub.2-C.sub.4)-alkylamino selected from aminoacetic acid, .alpha.-aminobutyric acid or .alpha.-aminopropionic acid and the optical isomers thereof; (C.sub.7-C.sub.9)aralkylamino; (C.sub.1-C.sub.4)alkoxycarbonylamino substituted (C.sub.1-C.sub.4) alkyl group; .alpha.-hydroxy(C.sub.1-C.sub.3)alkyl selected from hydroxymethyl, .alpha.-hydroxyethyl or .alpha.-hydroxy-1-methylethyl or .alpha.-hydroxypropyl; .alpha.-mercapto (C.sub.1-C.sub.3)alkyl selected from mercaptomethyl, .alpha.-mercaptoethyl, .alpha.-mercapto-1-methylethyl or .alpha.-mercaptopropyl; halo(C.sub.1-C.sub.3)alkyl group; a heterocycle selected from the group consisting of a five membered aromatic or saturated ring with one N, O, S or Se heteroatom optionally having a benzo or pyrido ring fused thereto, a five membered aromatic ring with two N, O, S, or Se heteroatoms optionally having a benzo or pyrido ring fused thereto, a six membered aromatic ring with one to three N, O, S or Se heteroatoms, or a six membered saturated ring with one or two N, O, S or Se heteroatoms and an adjacent appended O heteroatom; acyl or haloacyl group selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl; (C.sub.3-C.sub.6) cycloalkylcarbonyl, (C.sub.6-C.sub.10)aroyl selected from benzoyl or naphthoyl; halo substituted (C.sub.6-C.sub.10)aroyl; (C.sub.1-C.sub.4) alkylbenzoyl, or (heterocycle)-carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxycarbonyl selected from methoxycarbonyl, ethoxycarbonyl, straight or branched propoxycarbonyl, straight or branched butoxycarbonyl or allyloxycarbonyl; vinyl or a substituted vinyl group with substitution selected from (C.sub.1-C.sub.3) alkyl, halogen, (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl, .beta.-naphthyl, halo(C.sub.1-C.sub.3)alkyl, or a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)-alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.1-C.sub.4)alkoxy group; C.sub.6-aryloxy selected from phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1-C.sub.4) alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; (C.sub.7-C.sub.10)aralkyloxy; vinyloxy or a substituted vinyloxy group with substitution selected from (C.sub.1-C.sub.4)alkyl, cyano, carboxy, or (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; R.sup.aR.sup.bamino(C.sub.1-C.sub.4)alkoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2 W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; or R.sup.aR.sup.baminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, or 1,1-dimethylethyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2 W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; and when R=R.sup.4 (CH.sub.2).sub.nCO-- and n=1-4, R.sup.4 is selected from hydrogen; amino; straight or branched (C.sub.1-C.sub.4) alkyl group selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C.sub.3-C.sub.6)cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6)cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3)acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted(C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.7-C.sub.10)aralkyl; acyloxy or haloacyloxy group selected from acetyl, propionyl, chloroacetyl, trichloroacetyl, (C.sub.3-C.sub.6) cycloalkylcarbonyl, (C.sub.6-C.sub.10)aroyl selected from benzoyl or naphthoyl, halo substituted (C.sub.6-C.sub.10)aroyl, (C.sub.1-C.sub.4)alkylbenzyl or (heterocycle)-carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxy; C.sub.6-aryloxy selected from phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1-C.sub.4)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; (C.sub.7-C.sub.10)aralkyloxy; (C.sub.1-C.sub.3)alkylthio group selected from methylthio, ethylthio, propylthio or allylthio; C.sub.6-arylthio group selected from phenylthio or substituted phenylthio with substitution selected from halo, (C.sub.1-C.sub.4)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; C.sub.6-arylsulfonyl group selected from phenylsulfonyl or substituted phenylsulfonyl with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3) alkylamino or carboxy; (C.sub.7-C.sub.8)aralkylthio group; a heterocycle as defined hereinabove; hydroxy; mercapto; mono- or di-straight or branched chain (C.sub.1-C.sub.6)alkylamino with the alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl; (C.sub.2-C.sub.5)azacycloalkyl group; a carboxy(C.sub.2-C.sub.4)alkylamino group with the carboxy alkyl selected from aminoacetic acid, .alpha.-aminopropionic acid, .alpha.-aminobutyric acid and the optical isomers thereof; .alpha.-hydroxy(C.sub.1-C.sub.3)alkyl selected from hydroxymethyl, .alpha.-hydroxyethyl or .alpha.-hydroxy-1-methylethyl or .alpha.-hydroxypropyl; halo(C.sub.1-C.sub.3)alkyl group; acyl or haloacyl selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl; (C.sub.3-C.sub.6) cycloalkylcarbonyl; (C.sub.6-C.sub.10)aroyl selected from benzoyl or naphthoyl; halo substituted (C.sub.6-C.sub.10)aroyl; (C.sub.1-C.sub.4)alkylbenzoyl, or (heterocycle)carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxycarbonylamino group selected from tert-butoxycarbonylamino, allyloxycarbonylamino, methoxycarbonylamino, ethoxycarbonylamino or propoxycarbonylamino; (C.sub.1-C.sub.4)alkoxycarbonyl group selected from methoxycarbonyl, ethoxycarbonyl, straight or branched propoxycarbonyl, allyloxycarbonyl or straight or branched butoxycarbonyl; R.sup.aR.sup.b-amino(C.sub.1-C.sub.4)alkoxy group wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6 or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)-alkyl, O, S, --NH, --NOB, and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; or R.sup.aR.sup.baminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)-alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)-alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl, and when R=R.sup.4' (CH.sub.2).sub.nSO.sub.2-- and n=0 R.sup.4' is selected from amino; monosubstituted amino selected from straight or branched (C.sub.1-C.sub.6)alkylamino, cyclopropylamino, cyclobutylamino, benzylamino or phenylamino; disubstituted amino selected from dimethylamino, diethylamino, ethyl(1-methylethyl)amino, monomethylbenzylamino, piperidinyl, morpholinyl, 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl) or 4-(1,2,4-triazolyl); straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C.sub.3-C.sub.6) cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6)cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3) acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.7-C.sub.9)aralkyl; halo(C.sub.1-C.sub.3)alkyl group; a heterocycle as defined hereinabove; R.sup.aR.sup.b amino (C.sub.1-C.sub.4)alkoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)-alkyl selected from methyl, ethyl, n-propyl, 1-methyl-ethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W--(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3) alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)-alkyl; or R.sup.aR.sup.b aminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methyl-propyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3) alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3) alkyl; and when R=R.sup.4' (CH.sub.2).sub.nSO.sub.2-- and n=1-4, R.sup.4' is selected from hydrogen; straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methyl-propyl or 1,1-dimethylethyl; (C.sub.1-C.sub.4) carboxyalkyl; (C.sub.3-C.sub.6)cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6) cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3)-acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, tri-halo(C.sub.1-C.sub.3) alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxy-carbonyl, (C.sub.1-C.sub.3) alkylamino or carboxy; (C.sub.7-C.sub.9)aralkyl selected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; (C.sub.1-C.sub.4)alkoxy; C.sub.6-aryloxy selected from phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1-C.sub.3)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3) alkylamino; (C.sub.7-C.sub.10)aralkyloxy; R.sup.aR.sup.b amino (C.sub.1-C.sub.4) alkoxy, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)-alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, or --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; or R.sup.aR.sup.b aminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; (C.sub.1-C.sub.3) alkylthio selected from methylthio, ethylthio or n-propylthio; C.sub.6-arylthio selected from phenylthio or substituted phenylthio with substitution selected from halo, (C.sub.1-C.sub.3)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; (C.sub.7-C.sub.8) aralkylthio; a heterocycle as defined hereinabove; hydroxy; mercapto; mono- or di-straight or branched (C.sub.1-C.sub.6)alkyl- amino group with the alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl; halo (C.sub.1-C.sub.3) alkyl; acyl or haloacyl selected from acetyl, propionyl, chloro-acetyl, trifluoroacetyl; (C.sub.3-C.sub.6) cycloalkylcarbonyl; (C.sub.6-C.sub.10) aroyl selected from benzoyl or naphthoyl; halo substituted (C.sub.6-C.sub.10)aroyl, (C.sub.1-C.sub.4)alkylbenzoyl, or (heterocycle) carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxycarbonyl selected from methoxycarbonyl, ethoxycarbonyl, straight or branched propoxycarbonyl, allyloxycarbonyl or straight or branched butoxycarbonyl; R.sup.5 is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl selected from methyl, ethyl, n-propyl or 1-methylethyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; (C.sub.7-C.sub.9) aralkyl group; a heterocycle as defined hereinabove; or --(CH.sub.2).sub.nCOOR.sup.7 where n=0-4 and R.sup.7 is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl group selected from methyl, ethyl, n-propyl or 1-methylethyl; or (C.sub.6-C.sub.10)aryl group selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; R.sup.6 is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl group selected from methyl, ethyl, n-propyl or 1-methylethyl; (C.sub.6-C.sub.10)aryl group selected

from phenyl, .alpha.-naphthyl or .beta.-naphthyl; (C.sub.7-C.sub.9)-aralkyl group; a heterocycle as defined hereinabove; or --(CH.sub.2).sub.nCOOR.sup.7' where n=0-4 and R.sup.7' is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl selected from methyl, ethyl, n-propyl or 1-methylethyl; or (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; with the proviso that R.sup.5 and R.sup.6 cannot both be hydrogen; or R.sup.5 and R.sup.6 taken together are --(CH.sub.2).sub.2W(CH.sub.2).sub.2--, wherein W is selected from (CH.sub.2).sub.q and q=0-1, --NH, --N(C.sub.1-C.sub.3)-alkyl, --N(C.sub.1-C.sub.4) alkoxy, oxygen, sulfur or substituted congeners selected from (L or D)proline, ethyl(L or D) rolinate, morpholine, pyrrolidine or piperidine; and the pharmacologically acceptable organic and inorganic salts or metal complexes..Iaddend.

.Iadd.4. A method for the treatment or control of bacterial infections in warm-blooded animals which comprises administering to said animal having a bacterial infection a pharmacologically effective amount of a compound of formula I: ##STR00225## wherein X is selected from amino, NR.sup.1R.sup.2, or halogen, the halogen is selected from bromine, chlorine, fluorine or iodine, and when X is NR.sup.1R.sup.2, R.sup.1 is methyl or ethyl and R.sup.2 is methyl or ethyl; R is R.sup.4(CH.sub.2).sub.nCO--; n is 1-4; and R.sup.4 is monosubstituted or disubstitued amino selected from straight or branched (C.sub.1-C.sub.6)alkylamino with the alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl and pharmacologically acceptable organic and inorganic salts or metal complexes..Iaddend.

.Iadd.5. A method for the treatment or control of bacterial infections in warm-blooded animals which comprises administering to said animal having a bacterial infection a pharmacologically effective amount of a compound of formula I: ##STR00226## wherein X is N(CH.sub.3).sub.2 and R is R.sup.4(CH.sub.2).sub.nCO-- where n=1-4 and R.sup.4 is monosubstituted or disubstituted amino selected from straight or branched (C.sub.1-C.sub.6)alkylamino, with the alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl and pharmacologically acceptable organic and inorganic salts or metal complexes..Iaddend.

.Iadd.6. A method for the treatment or control of bacterial infections in warm-blooded animals which comprises administering to said animal having a bacterial infection a pharmacologically effective amount of a compound of formula I: ##STR00227## wherein X is N(CH.sub.3).sub.2 and R is R.sup.4(CH.sub.2).sub.nCO-- where n is 1 and R.sup.4 is monosubstituted or disubstituted amino selected from straight or branched (C.sub.1-C.sub.6)alkylamino, with the alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl and pharmacologically acceptable organic and inorganic salts or metal complexes..Iaddend.

.Iadd.7. A method for the treatment or control of bacterial infections in warm-blooded animals which comprises administering to said animal having a bacterial infection a pharmacologically effective amount of a compound of formula I: ##STR00228## wherein R.sup.4 is a monosubstituted straight or branched C.sub.4-alkylamino, and pharmacologically acceptable organic and inorganic salts or metal complexes..Iaddend.

.Iadd.8. A method for the treatment or control of bacterial infections in warm-blooded animals caused by bacteria having the TetM and TetK resistant determinants which comprises administering to said animal a pharmacologically effective amount of a compound of the formula: ##STR00229## wherein: X is selected from amino, NR.sup.1R.sup.2 or halogen; the halogen is selected from bromine, chlorine, fluorine or iodine; R.sup.1 is selected from hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl and 1-methylpropyl; R.sup.2 is selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, and 1,1-dimethylethyl such that when X=NR.sup.1R.sup.2 and R.sup.1=hydrogen, R.sup.2=methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; and when R.sup.1=methyl or ethyl, R.sup.2=methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=n-propyl, R.sup.2=n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=1-methylethyl, R.sup.2=n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=n-butyl, R.sup.2=n-butyl, 1-methylpropyl or 2-methylpropyl; and when R.sup.1=1-methylpropyl, R.sup.2=2-methylpropyl; R is selected from R.sup.4(CH.sub.2).sub.nCO-- or R.sup.4' (CH.sub.2).sub.nSO.sub.2--; and n=0-4; and when R=R.sup.4(CH.sub.2).sub.n CO-- and n=0, R.sup.4 is selected from hydrogen; amino; monosubstituted amino selected from straight or branched (C.sub.1-C.sub.6)alkylamino, cyclopropylamino, cyclobutylamino, benzylamino or phenylamino; disubstituted amino selected from dimethylamino, diethylamino, ethyl(1-methylethyl)amino, monomethylbenzylamino, piperidinyl, morpholinyl, 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl) or 4-(1,2,4-triazolyl); straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C.sub.3-C.sub.6)cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6)cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3)acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4) alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.7-C.sub.9) aralkyl selected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; .alpha.-amino-(C.sub.1-C.sub.4)alkyl selected from aminomethyl, .alpha.-aminoethyl, .alpha.-aminopropyl or .alpha.-aminobutyl; carboxy (C.sub.2-C.sub.4)-alkylamino selected from aminoacetic acid, .alpha.-aminobutyric acid or .alpha.-aminopropionic acid and the optical isomers thereof; (C.sub.7-C.sub.9)aralkylamino; (C.sub.1-C.sub.4)alkoxycarbonylamino substituted (C.sub.1-C.sub.4) alkyl group; .alpha.-hydroxy(C.sub.1-C.sub.3)alkyl selected from hydroxymethyl, .alpha.-hydroxyethyl or .alpha.-hydroxy-1-methylethyl or .alpha.-hydroxypropyl; .alpha.-mercapto (C.sub.1-C.sub.3)alkyl selected from mercaptomethyl, .alpha.-mercaptoethyl, .alpha.-mercapto-1-methylethyl or .alpha.-mercaptopropyl; halo(C.sub.1-C.sub.3)alkyl group; a heterocycle selected from the group consisting of a five membered aromatic or saturated ring with one N, O, S or Se heteroatom optionally having a benzo or pyrido ring fused thereto, a five membered aromatic ring with two N, O, S, or Se heteroatoms optionally having a benzo or pyrido ring fused thereto, a six membered aromatic ring with one to three N, O, S or Se heteroatoms, or a six membered saturated ring with one or two N, O, S or Se heteroatoms and an adjacent appended O heteroatom; acyl or haloacyl group selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl; (C.sub.3-C.sub.6) cycloalkylcarbonyl, (C.sub.6-C.sub.10)aroyl selected from benzoyl or naphthoyl; halo substituted (C.sub.6-C.sub.10)aroyl; (C.sub.1-C.sub.4) alkylbenzoyl, or (heterocycle)-carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxycarbonyl selected from methoxycarbonyl, ethoxycarbonyl, straight or branched propoxycarbonyl, straight or branched butoxycarbonyl or allyloxycarbonyl; vinyl or a substituted vinyl group with substitution selected from (C.sub.1-C.sub.3) alkyl, halogen, (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl, .beta.-naphthyl, halo(C.sub.1-C.sub.3)alkyl, or a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)-alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.1-C.sub.4)alkoxy group; C.sub.6-aryloxy selected from phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1-C.sub.4) alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; (C.sub.7-C.sub.10)aralkyloxy; vinyloxy or a substituted vinyloxy group with substitution selected from (C.sub.1-C.sub.4)alkyl, cyano, carboxy, or (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; R.sup.aR.sup.bamino(C.sub.1-C.sub.4)alkoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2 W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; or R.sup.aR.sup.baminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, or 1,1-dimethylethyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2 W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; and when R=R.sup.4 (CH.sub.2).sub.nCO-- and n=1-4, R.sup.4 is selected from hydrogen; amino; straight or branched (C.sub.1-C.sub.4) alkyl group selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C.sub.3-C.sub.6)cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6)cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3)acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted(C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.7-C.sub.10)aralkyl; acyloxy or haloacyloxy group selected from acetyl, propionyl, chloroacetyl, trichloroacetyl, (C.sub.3-C.sub.6) cycloalkylcarbonyl, (C.sub.6-C.sub.10)aroyl selected from benzoyl or naphthoyl, halo substituted (C.sub.6-C.sub.10)aroyl, (C.sub.1-C.sub.4)alkylbenzyl or (heterocycle)-carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxy; C.sub.6-aryloxy selected from phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1-C.sub.4)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; (C.sub.7-C.sub.10)aralkyloxy; (C.sub.1-C.sub.3)alkylthio group selected from methylthio, ethylthio, propylthio or allylthio; C.sub.6-arylthio group selected from phenylthio or substituted phenylthio with substitution selected from halo, (C.sub.1-C.sub.4)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; C.sub.6-arylsulfonyl group selected from phenylsulfonyl or substituted phenylsulfonyl with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3) alkylamino or carboxy; (C.sub.7-C.sub.8)aralkylthio group; a heterocycle as defined hereinabove; hydroxy; mercapto; mono- or di-straight or branched chain (C.sub.1-C.sub.6)alkylamino with the alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl; (C.sub.2-C.sub.5)azacycloalkyl group; a carboxy(C.sub.2-C.sub.4)alkylamino group with the carboxy alkyl selected from aminoacetic acid, .alpha.-aminopropionic acid, .alpha.-aminobutyric acid and the optical isomers thereof; .alpha.-hydroxy(C.sub.1-C.sub.3)alkyl selected from hydroxymethyl, .alpha.-hydroxyethyl or .alpha.-hydroxy-1-methylethyl or .alpha.-hydroxypropyl; halo(C.sub.1-C.sub.3)alkyl group; acyl or haloacyl selected from acetyl, propionyl, chloroacetyl, trifluoroacetyl; (C.sub.3-C.sub.6) cycloalkylcarbonyl; (C.sub.6-C.sub.10)aroyl selected from benzoyl or naphthoyl; halo substituted (C.sub.6-C.sub.10)aroyl; (C.sub.1-C.sub.4)alkylbenzoyl, or (heterocycle)carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxycarbonylamino group selected from tert-butoxycarbonylamino, allyloxycarbonylamino, methoxycarbonylamino, ethoxycarbonylamino or propoxycarbonylamino; (C.sub.1-C.sub.4)alkoxycarbonyl group selected from methoxycarbonyl, ethoxycarbonyl, straight or branched propoxycarbonyl, allyloxycarbonyl or straight or branched butoxycarbonyl; R.sup.aR.sup.b-amino(C.sub.1-C.sub.4)alkoxy group wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6 or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)-alkyl, O, S, --NH, --NOB, and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; or R.sup.aR.sup.baminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)-alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)-alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl, and when R=R.sup.4' (CH.sub.2).sub.nSO.sub.2-- and n=0 R.sup.4' is selected from amino; monosubstituted amino selected from straight or branched (C.sub.1-C.sub.6)alkylamino, cyclopropylamino, cyclobutylamino, benzylamino or phenylamino; disubstituted amino selected from dimethylamino, diethylamino, ethyl(1-methylethyl)amino, monomethylbenzylamino, piperidinyl, morpholinyl, 1-imidazolyl, 1-pyrrolyl, 1-(1,2,3-triazolyl) or 4-(1,2,4-triazolyl); straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; (C.sub.3-C.sub.6) cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6)cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3) acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, trihalo(C.sub.1-C.sub.3)alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.3)alkylamino or carboxy; (C.sub.7-C.sub.9)aralkyl; halo(C.sub.1-C.sub.3)alkyl group; a heterocycle as defined hereinabove; R.sup.aR.sup.b amino (C.sub.1-C.sub.4)alkoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)-alkyl selected from methyl, ethyl, n-propyl, 1-methyl-ethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W--(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3) alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)-alkyl; or R.sup.aR.sup.b aminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3) alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3) alkyl; and when R=R.sup.4' (CH.sub.2).sub.nSO.sub.2-- and n=1-4, R.sup.4' is selected from hydrogen; straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methyl-propyl or 1,1-dimethylethyl; (C.sub.1-C.sub.4) carboxyalkyl; (C.sub.3-C.sub.6)cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; a substituted (C.sub.3-C.sub.6) cycloalkyl group with substitution selected from (C.sub.1-C.sub.3)alkyl, cyano, amino or (C.sub.1-C.sub.3)-acyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; a substituted (C.sub.6-C.sub.10)aryl group with substitution selected from halo, (C.sub.1-C.sub.4)alkoxy, tri-halo(C.sub.1-C.sub.3) alkyl, nitro, amino, cyano, (C.sub.1-C.sub.4)alkoxy-carbonyl, (C.sub.1-C.sub.3) alkylamino or carboxy; (C.sub.7-C.sub.9)aralkyl selected from benzyl, 1-phenylethyl, 2-phenylethyl or phenylpropyl; (C.sub.1-C.sub.4)alkoxy; C.sub.6-aryloxy selected from phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1-C.sub.3)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3) alkylamino; (C.sub.7-C.sub.10)aralkyloxy; R.sup.aR.sup.b amino (C.sub.1-C.sub.4) alkoxy, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)-alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, or --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; or R.sup.aR.sup.b aminoxy group, wherein R.sup.aR.sup.b is a straight or branched (C.sub.1-C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, or 2-methylpropyl or R.sup.aR.sup.b is (CH.sub.2).sub.m, m=2-6, or --(CH.sub.2).sub.2W(CH.sub.2).sub.2-- wherein W is selected from --N(C.sub.1-C.sub.3)alkyl, O, S, --NH, --NOB and B is selected from hydrogen or (C.sub.1-C.sub.3)alkyl; (C.sub.1-C.sub.3) alkylthio selected from methylthio, ethylthio or n-propylthio; C.sub.6-arylthio selected from phenylthio or substituted phenylthio with substitution selected from halo, (C.sub.1-C.sub.3)alkyl, nitro, cyano, thiol, amino, carboxy, di(C.sub.1-C.sub.3)alkylamino; (C.sub.7-C.sub.8) aralkylthio; a heterocycle as defined hereinabove; hydroxy; mercapto; mono- or di-straight or branched (C.sub.1-C.sub.6)alkyl- amino group with the alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl; halo (C.sub.1-C.sub.3) alkyl; acyl or haloacyl selected from acetyl, propionyl, chloro-acetyl, trifluoroacetyl; (C.sub.3-C.sub.6) cycloalkylcarbonyl; (C.sub.6-C.sub.10) aroyl selected from benzoyl or naphthoyl; halo substituted (C.sub.6-C.sub.10)aroyl, (C.sub.1-C.sub.4)alkylbenzoyl, or (heterocycle) carbonyl, the heterocycle as defined hereinabove; (C.sub.1-C.sub.4)alkoxycarbonyl selected from methoxycarbonyl, ethoxycarbonyl, straight or branched propoxycarbonyl, allyloxycarbonyl or straight or branched butoxycarbonyl; R.sup.5 is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl selected from methyl, ethyl, n-propyl or 1-methylethyl; (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; (C.sub.7-C.sub.9) aralkyl group; a heterocycle as defined hereinabove; or --(CH.sub.2).sub.nCOOR.sup.7 where n=0-4 and R.sup.7 is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl group selected from methyl, ethyl, n-propyl or 1-methylethyl; or (C.sub.6-C.sub.10)aryl group selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; R.sup.6 is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl group selected from methyl,

ethyl, n-propyl or 1-methylethyl; (C.sub.6-C.sub.10)aryl group selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; (C.sub.7-C.sub.9)-aralkyl group; a heterocycle as defined hereinabove; or --(CH.sub.2).sub.nCOOR.sup.7' where n=0-4 and R.sup.7' is selected from hydrogen; straight or branched (C.sub.1-C.sub.3)alkyl selected from methyl, ethyl, n-propyl or 1-methylethyl; or (C.sub.6-C.sub.10)aryl selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl; with the proviso that R.sup.5 and R.sup.6 cannot both be hydrogen; or R.sup.5 and R.sup.6 taken together are --(CH.sub.2).sub.2W(CH.sub.2).sub.2--, wherein W is selected from (CH.sub.2).sub.q and q=0-1, --NH, --N(C.sub.1-C.sub.3)-alkyl, --N(C.sub.1-C.sub.4) alkoxy, oxygen, sulfur or substituted congeners selected from (L or D)proline, ethyl(L or D)prolinate, morpholine, pyrrolidine or piperidine; and the pharmacologically acceptable organic and inorganic salts or metal complexes..Iaddend.

.Iadd.9. A method for the treatment or control of bacterial infections in warm-blooded animals caused by bacteria having the TetM and TetK resistant determinants which comprises administering to said animal a pharmacologically effective amount as of compound of formula I: ##STR00230## wherein X is selected from amino, NR.sup.1R.sup.2, or halogen, the halogen is selected from bromine, chlorine, fluorine or iodine, and when X is NR.sup.1R.sup.2, R.sup.1 is methyl or ethyl and R.sup.2 is methyl or ethyl; R is R.sup.4(CH.sub.2).sub.nCO--; n is 1-4; and R.sup.4 is monosubstituted or disubstituted amino selected from straight or branched chain (C.sub.1-C.sub.6)alkylamino with the alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl and pharmacologically acceptable organic and inorganic salts or metal complexes..Iaddend.

.Iadd.10. A method for the treatment or control of bacterial infections in warm-blooded animals caused by bacteria having the TetM and TetK resistant determinants which comprises administering to said animal a pharmacologically effective amount as of compound of formula I: ##STR00231## wherein X is N(CH.sub.3).sub.2 and R is R.sup.4(CH.sub.2).sub.nCO-- where n=1-4 and R.sup.4 is monosubstituted or disubstituted amino selected from straight or branched (C.sub.1-C.sub.6)alkylamino, with the alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl and pharmacologically acceptable organic and inorganic salts or metal complexes..Iaddend.

.Iadd.11. A method for the treatment or control of bacterial infections in warm-blooded animals caused by bacteria having the TetM and TetK resistant determinants which comprises administering to said animal a pharmacologically effective amount as of compound of formula I: ##STR00232## wherein X is N(CH.sub.3).sub.2and R is R.sup.4(CH.sub.2).sub.nCO-- where n is 1 and R.sup.4 is monosubstituted or disubstituted amino selected from straight or branched (C.sub.1-C.sub.6)alkylamino, with the alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 2-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 3-methylbutyl, n-hexyl, 1-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 2-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl or 1-methyl-1-ethylpropyl and pharmacologically acceptable organic and inorganic salts or metal complexes..Iaddend.

.Iadd.12. A method for the treatment or control of bacterial infections in warm-blooded animals caused by bacteria having the TetM and TetK resistant determinants which comprises administering to said animal a pharmacologically effective amount as of compound of formula I: ##STR00233## wherein R.sup.4 is a monosubstituted straight or branched C.sub.4-alkylamino, and pharmacologically acceptable organic and inorganic salts or metals complexes..Iaddend.
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