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Method for treating bacterial infection with novel 7-substituted-9-substituted amino 6-demethyl-6-deoxytetracyclines |
| RE40086 |
Method for treating bacterial infection with novel 7-substituted-9-substituted amino 6-demethyl-6-deoxytetracyclines
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| Patent Drawings: | |
| Inventor: |
Hlavka, et al. |
| Date Issued: |
February 19, 2008 |
| Application: |
11/318,390 |
| Filed: |
December 23, 2005 |
| Inventors: |
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)
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| Assignee: |
Wyeth Holdings Corporation (Madison, NJ) |
| Primary Examiner: |
Badio; Barbara P. |
| Assistant Examiner: |
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| Attorney Or Agent: |
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| U.S. Class: |
514/152 |
| Field Of Search: |
514/152 |
| International Class: |
A61K 31/65 |
| U.S Patent Documents: |
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| Foreign Patent Documents: |
109 850; 901107; WO 84/01895; WO 89/02270 |
| Other References: |
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Norden et al., "Treatment of Experimental Chronic Osteomyelitis Due to Staphylococcus Aureus with Vancomycin and Rifampin," J. Infect. Dis. 147:352-357 (1983). cited by other. Norden et al., "Clindamycin Treatment of Experimental Chronic Osteomyelitis Due to Staphylococcus Aureus," J. Infect. Dis. 153:956-959 (1986). cited by other. Norden et al., "Treatment of Experimental Chronic Osteomyelitis Due to Staphylococcus Aureus with Ampicillin/Sulbactam," J. Infect. Dis. 161:52-53 (1990). cited by other. Pawelczyk et al., "Kinetics of Drug Decomposition Part 74.Kinetics of Degradation of Minocycline in Aqueous Solution", Pharmacol. Pharm. 34:409-421 (1982). cited by other. Pratt, Coupled TranScription-translation in Prokaryotic Cell-free Systems, Transcription and Translation, a Practical Approach, (B.D. Hames and S.J. Higgins, eds.) p. 179-209, IRL Press, Oxford-Washington, (1984). cited by other. Raasch,"Interaction of Oral Antibiotics and Common Chronic Medications" Geriatrics 42:69-74 (1987). cited by other. Remmers et al., "Some Observations on the Kinetics of the C.4 Epimerization of Tetracycline," J. Pharm. Sci. 52:752-756 (1963). cited by other. Robertson, "p-Aminophenyllacetic Acid", Org. Syn. Coll. 1:52 (1941). cited by other. Rissing, "Animal Models of Osteomyelitis: Knowledge, Hypothesis and Speculation," Infect. Dis. Clin. North Am. 4:377-390 (1990). cited by other. Skillman et al., "Respiratory Failure, Hypotension, Sepsis, and Jaundice. A Clinical Syndrome Associated with Lethal Hemorrhage from Acute Stress Ulceration of the Stomach," American Journal of Surgery 117:523-530 (1969). cited by other. Slama et al., "Oral Ciprofloxacin Therapy for Osteomyelitis Caused by Aerobic Gram Negative Bacilli," Am. J. Med. 82(Suppl 4A):259-261 (1987). cited by other. Solomkin et al., "Results of a Multicenter Trial Comparing Imipenem/Cilastatin to Tobramycin/Clindamycin for Intra-abdominal Infections," Annals of Surgery 212:581-591 (1990). cited by other. Spencer et al., "6-Deocytetracyclines,. V. 7,9-Disubstituted Products", J. Med. Chem. 6:405-407 (1963). cited by other. Sum et al., "Synthesis of Novel Tetracycline Derivatives with Substitution at the C-8 Position," Tetrahedron Letters vol. 35, No. 12, pp. 1835-1836 (1994). cited by other. Swenson et al. "The Bacteriology of Intra-abdominal Infections," Archives of Surgery 109:398-399 (1974). cited by other. Tapp et al., "Tetracycline Toxicity," Experientia 22:530-531 (1966). cited by other. Tice, "Outpatient Parenteral Antimicrobial Therapy for Osteomyelitis," Infect. Dis. Clin. North Am. 12:903-919 (1998). cited by other. Van Den Bogert et al., "Tissue distribution and Effects on Mitochondrial Protein Synthesis of Tetracyclines After Prolonged Continuous Intravenous Administration to Rats," Biochem. Pharmacol. 30:1706-1709 (1981). cited by other. Waldvogel, "Osteomyelitis," In Gorbach SL et al., eds. Infectious Diseases, Saunders, Philadelphia 1339-1344 (1988). cited by other. Westfall et al., "Formulation of a Stable Trace Element Solution for TPN" Am. J. Hosp. Pharm. 37:1620 (1980). cited by other. Watson, "Chloramphenicol Toxicity in Dogs," Research in Veterinary Science 23:66-69 (1977). cited by other. Williams et al., "Minocycline: Possible Vestibular Side-Effects," Lancet. 2:744-746 (1974). cited by other. Woodward, "m-Hydroxybenzaldehyde", Org. Syn. Coll. 3:453 (1955. cited by other. Yuen, et al., "Kinetics of Concomitatnt Degradation of Tetracycline to Epitetracycline to Epitetracycline, Anhydrotetracycline, and Epianhydrotetracycline in Acid Phosphate Solution", J. Pharm. Sci. 66:1648-1650 (1977). cited by other. Zubay, "In-vitro Synthesis of Protein in Microbial Systems", Ann. Rev. Genet. 7:267-287 (1973). cited by other. The Merck Index, Entries #2111 and 5936 10.sup.th Ed. (1983) pp. 300,301, & 869. cited by other. World Health Organization Technical Report Series 687:1-184 (1983). cited by other. |
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| 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. |
| Claim: |
We claim:
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 compoundof 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 and1-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) aralkylselected 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 fromaminoacetic 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 orpyrido 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 saturatedring 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 frommethoxycarbonyl, 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 fromhalo, (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 isselected 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 Bis 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 withsubstitution 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 asdefined 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 orbranched 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 fromaminoacetic 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 fromtert-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 isselected 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 orR.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 fromdimethylamino, 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 substitutionselected 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, whereinR.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 fromcyclopropyl, 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 selectedfrom 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 ornaphthoyl; 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 branchedpropoxycarbonyl, 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 andR.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 acompound 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 andR.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 or2-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.orcarboxy; (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 orpyrido 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 saturatedring 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 withsubstitution 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 withsubstitution 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 frommethyl, 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 selectedfrom 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 orhaloacyloxy 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 substitutionselected 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 withsubstitution 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 definedhereinabove; 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 definedhereinabove; .[.(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 orpropoxycarbonylamino; (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 groupwherein 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 fromdimethylamino, 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 substitutionselected 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)arylgroup 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)alkylgroup; 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, or2-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-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 selectedfrom 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 fromcyclopropyl, 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 selectedfrom 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 isselected 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 fromhydrogen; 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 or1-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 selectedfrom 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 orbranched (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; asubstituted (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 selectedfrom 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 aminoaceticacid, .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)alkylselected 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 fivemembered 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 Seheteroatoms 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; halosubstituted (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 orcarboxy; (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.bis 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; asubstituted (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; asubstituted(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 selectedfrom 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 substitutedphenylsulfonyl 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; aheterocycle 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; acarboxy(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 selectedfrom 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 fromamino; 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, whereinR.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 frommethyl, 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 isselected 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 substitutionselected 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, whereinR.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 fromphenylthio 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, theheterocycle 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 definedhereinabove; 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 fromphenyl, .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 andR.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 isR.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 andpharmacologically 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 amountof 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 fromstraight 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 orsaturated 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 aromaticring 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 fromhalo, (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 orR.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 fromphenoxy 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 opticalisomers 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 asdefined 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 frommethoxycarbonyl, 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)alkylselected 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 fromdimethylamino, 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 substitutionselected 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, whereinR.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, cyclopentylor 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; asubstituted (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 orbranched 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 or1-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 andR.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.5and 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 orsubstituted 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 amountas 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 methylor 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 or1-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 amountas 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 alkylselected 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 amountas 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 alkylselected 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 amountas 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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