7-(substituted)-8-(substituted)-9-(substituted amino)-6-demethyl-6-deoxytetracyclines

A method for the prevention or treatment of bacterial infections in warm-blooded animals which comprises administering to said animal a pharmacologically effective amount of a compound of the formula:

• ##STR225## wherein:
• X is selected from halogen or trifluoromethylsulfonyloxy;
• the halogen is selected from bromine, chlorine, or fluorine;
• R and R.sup.1 are the same or different and are selected from halogen selected from chlorine, bromine, fluorine or iodine;
• or --NR.sup.2 R.sup.3 ;
• R.sup.2 is selected from hydrogen, methyl, or ethyl and R.sup.3 is selected from hydrogen, methyl, ethyl, R.sup.4 (CH.sub.2).sub.n CO-- or R.sup.4 ' (CH.sub.2).sub.n SO.sub.2 --, n is 0-4, with the proviso that when R or R.sup.1 =NR.sup.2 R.sup.3 and R.sup.2 =methyl or ethyl;
• R.sup.3 =methyl or ethyl, and when R or R.sup.1 =NR.sup.2 R.sup.3 and R.sup.2 =hydrogen, R.sup.3 is selected from hydrogen, R.sup.4 (CH.sub.2).sub.n CO-- or R.sup.4 ' (CH.sub.2).sub.n SO.sub.2 --;
• and when R.sup.3 =R.sup.4 (CH.sub.2).sub.n CO-- and n=0,
• R.sub.4 is selected from hydrogen;
• (C.sub.1 -C.sub.2)alkyl group selected from methyl or ethyl;
• a heterocycle group selected from a five membered aromatic or saturated ring with one N, O, or S heteroatom optionally having a benzo or pyrido ring fused thereto selected from ##STR226## wherein Z=N, O or S or a five membered aromatic ring with two N, O or S heteroatoms optinonally having a benzo or pyrido ring fused thereto selected from ##STR227## wherein Z or Z.sup.1 =N, O, or S;
• (C.sub.1 -C.sub.4)alkoxygroup;
• C.sub.6 -aryloxy group selected from phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1 -C.sub.4)alkyl;
• (C.sub.7 -C.sub.10)aralkyloxy;
• .alpha.-aminomethyoxycarbonyl;
• or halomethoxycarbonyl;
• and when R.sup.3 =R.sup.4 (CH.sub.2).sub.n CO-- and n=1-4,
• R.sup.4 is selected from hydrogen;
• (C.sub.1 -C.sub.2)alkyl group selected from methyl or ethyl (C.sub.6 -C.sub.10)aryl group selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl;
• and when R.sup.3 =R.sup.4 ' (CH.sub.2).sub.n SO.sub.2 -- and n=0,
• R.sup.4 ' is selected from (C.sub.1 -C.sub.2)alkyl group selected from methyl or ethyl;
• (C.sub.6 -C.sub.10)aryl group selected from phenyl, .alpha.-naphthyl or .beta.-naphthyl;
• R.sup.5 is selected from hydrogen;
• straight or branched (C.sub.1 -C.sub.3)alkyl group selected from methyl, ethyl, n-propyl or 1-methylethyl;
• 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;
• 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.m where m=0-1, --NH,--N(C.sub.1 -C.sub.3)alkyl straight or branched, --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.