You’re using a public version of DrugPatentWatch with 5 free searches available | Register to unlock more free searches. CREATE FREE ACCOUNT

Last Updated: March 29, 2024

Details for Patent: 5,494,903


✉ Email this page to a colleague

« Back to Dashboard


Title: 7-substituted-9-substituted amino-6-demethyl-6-deoxytetracyclines
Abstract:The invention is drawn to 7-substituted-9-(substituted amino)-6-demethyl-6-deoxytetracycline compounds of the formula ##STR1## wherein R, X, R.sup.5 and R.sup.6 are defined in the specification. The compounds of the invention are useful as broad spectrum antibiotics.
Inventor(s): Hlavka; Joseph J. (Tuxedo Park, NY), Sum; Phaik-Eng (Pomona, NY), Gluzman; Yakov (Upper Saddle River, NJ), Lee; Ving J. (Monsey, NY), Ross; Adma A. (Airmont, NY)
Assignee: American Cyanamid Company (Wayne, NJ)
Filing Date:Aug 04, 1994
Application Number:08/286,096
Claims:1. A compound of the formula ##STR223## wherein: X is selected from amino, NR.sup.1 R.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.dbd.NR.sup.1 R.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.n CO-- or R.sup.4' (CH.sub.2).sub.n SO.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 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); a substituted (C.sub.3 -C.sub.6)cycloalkyl group with substitution selected from cyano, amino or (C.sub.1 -C.sub.3)acyl; 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; .alpha.-amino-(C.sub.1 -C.sub.4)alkyl selected from aminomethyl, .alpha.-aminoethyl, .alpha.-aminopropyl or .alpha.-amino-butyl; 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)cycloalcylcarbonyl, (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, straight or branched butoxycarbonyl or allyloxycarbonyl; a substituted vinyl group with substitution selected from halogen, 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.a R.sup.b amino(C.sub.1 -C.sub.4)alkoxy group, wherein R.sup.a R.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.a R.sup.b is (CH.sub.2).sub.m, m=2-6, or (CH.sub.2).sub.2 W(CH.sub.2)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.a R.sup.b aminoxy group, wherein R.sup.a R.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.a R.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.n CO-- and n-1-4, R.sup.4 is selected from amino;

a substituted (C.sub.3 -C.sub.6)cycloalkyl group with substitution selected from cyano, amino or (C.sub.1 -C.sub.3)acyl; 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; acyloxy or haloacyloxy group selected from acetyl, propionyl, chloroacetyl, trichlorocetyl, (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 allythio; 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.a R.sup.b - amino(C.sub.1 -C.sub.4)alkoxy group wherein R.sup.a R.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.a R.sup.b is (CH).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.a R.sup.b aminoxy group, wherein R.sup.a R.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.a R.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.dbd.R.sup.4' (CH.sub.2).sub.n SO.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-imidazoyl, 1-pyrrolyl, 1-(1,2,3-triazolyl) or 4-(1,2,4-triazolyl); a substituted (C.sub.3 -C.sub.6)cycloalkyl group with substitution selected from cyano, amino or (C.sub.1 -C.sub.3)acyl; halo(C.sub.1 -C.sub.3)alkyl group; a heterocycle as defined hereinabove;

R.sup.a R.sup.b amino (C.sub.1 -C.sub.4) alkoxy group, wherein R.sup.a R.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.a R.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.a R.sup.b aminoxy group, wherein R.sup.a R.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-methyl-propyl or R.sup.a R.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, --NY, --NOB and B is selected from hydrogen or (C.sub.1 -C.sub.3) alkyl; and when R.dbd.R.sup.4' (CH.sub.2).sub.n SO.sub.2 -- and n=1-4,

R.sup.4 ' is selected from C.sub.1 -C.sub.4)carboxyalkyl; a substituted (C.sub.3 -C.sub.6)cyclalkyl group with substitution selected from cyano, amino or (C.sub.1 -C.sub.3)-acyl; (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.a R.sup.b amino (C.sub.1 -C.sub.4) alkoxy, wherein R.sup.a R.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.a R.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, --NY, or NOB and B is selected from hydrogen or (C.sub.1 -C.sub.3)alkyl; or R.sup.a R.sup.b aminoxy group, wherein R.sup.a R.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.a R.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; (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 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.n COOR.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 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.n (COOR.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, --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. The compound according to claim 1, wherein:

X is selected form amino, NR.sup.1 R.sup.2, or halogen;

the halogen is selected from bromine, chlorine, fluorine or iodine;

and when X=NR.sup.1 R.sup.2 and R.sup.1 =methyl or ethyl,

R.sup.2 =methyl or ethyl

R is selected from R.sup.4 (CH.sub.2).sub.n CO-- or R.sup.4' (CH.sub.2).sub.n SO.sub.2 --;

and when R=R.sup.4 (CH.sub.2).sub.n CO-- and n=0,

R.sup.4 is selected from substituted (C.sub.6 -C.sub.10)aryl group with substitution selected from halo, (C.sub.1 -C.sub.4)alkoxy, nitro, amino, or (C.sub.1 -C.sub.2)alkoxycarbonyl;

(C.sub.1 -C.sub.4)alkoxycarbonyl group selected from methoxycarbonyl, ethoxycarbonyl, straight or branched propoxyl-carbonyl, straight or branched butoxycarbonyl or allyl-oxycarbonyl; a substituted (C.sub.6 -C.sub.10)aryl group with substitution selected from halo, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4) alkoxycarbonyl, halo-(C.sub.1 -C.sub.3)alkyl group; (C.sub.1 -C.sub.4)alkoxy group; C.sub.6 -aryloxy group selected form phenoxy or substituted phenoxy with substitution selected from halo, (C.sub.1 -C.sub.4)alkyl; (C.sub.7 -C.sub.10) aralkyloxy group; vinyloxy or substituted vinyloxy group with substitution selected from (C.sub.1 -C.sub.2)-alkyl; R.sup.a R.sup.b amino(C.sub.1 -C.sub.4)alkoxy group, wherein R.sup.a R.sup.b is a straight or branched (C.sub.1 -C.sub.4)alkyl selected from methyl, ethyl, n-propyl, 1-methylethyl, n-butyl; or R.sup.a R.sup.b aminoxy group, wherein R.sup.a R.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;

and when R=R.sup.4 (CH.sub.2).sub.n CO-- and n=1-4,

R.sup.4 is selected from amino; monosubstituted amino selected from straight or branched (C.sub.1 -C.sub.6)alkyl-amino, cyclopropylamino, cyclobutylamino, benzylamino or phenylamino; disubstituted amino selected from dimethylamino, diethylamino, ethyl(1-methylethyl)amino, monomethylbenzylamino, piperidinyl, morpholinyl, 1-imidazolyl, 1-pyrrolyl or 1-(1,2,3-triazolyl); a substituted (C.sub.6 -C.sub.10)aryl group with substitution selected from halo, (C.sub.1 -C.sub.4)alkoxy, nitro, amino, (C.sub.1 -C.sub.4)alkoxycarbonyl; acyloxy or haloacyloxy group selected from acetyl, propionyl or chloroacetyl; (C.sub.1 -C.sub.4)alkoxy group; R.sup.a R.sup.b amino(C.sub.1 -C.sub.4)alkoxy group, wherein R.sup.a R.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.a R.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. a R.sup.b aminoxy group, wherein R.sup.a R.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.a R.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, --NY, --NOB and B is selected from hydrogen or (C.sub.1 -C.sub.3)alkyl; halo (C.sub.1 -C.sub.3)-alkyl group; (C.sub.1 C.sub.4)alkoxycarbonylamino selected from tert-butoxycarbonylamino, allyloxycarbonylamino, methoxycarbonylamino, ethoxycarbonylamino or propoxycarbonylamino;

and when R.dbd.R.sup.4' (CH.sub.2).sub.n SO.sub.2 -- and n=0,

R.sup.4' is selected from a substituted (C.sub.6 -C.sub.10)aryl group with substitution selected from halo, (C.sub.1 -C.sub.4)alkoxy, nitro, (C.sub.1 -C.sub.4) alkoxycarbonyl;

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;

R.sup.6 is selected from hydrogen; straight or branched (C.sub.1 -C.sub.3)alkyl 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.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.

3. The compound according to claim 1 wherein said inorganic salts comprise hydrochloric, hydrobromic, hydroiodic, phosphoric, nitric or sulfate.

4. The compound according to claim 1 wherein said organic salts comprise acetate, benzoate, citrate, cysteine or other amino acids, fumarate, glycolate, maleate, succinate, tartrate, alkylsulfonate or arylsulfonate.

5. The compound according to claim 1 wherein said metal complexes comprise aluminium, calcium, iron, magnesium, manganese and complex salts.

6. A compound according to claim 1 [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11, 12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[(trifluoroacetyl)amin o]-2-naphthacenecarboxamide sulfate.

7. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6, 11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[(methoxyacetyl)amino]-1,11-di oxo-2-naphthacenecarboxamide.

8. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-9-[(4-Bromo-1-oxobutyl)amino]-4,7-bis(dimethyla mino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2- naphthacenecarboxamide.

9. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6, 11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[(1-oxo-2-propenyl) amino]-2-naphthacenecarboxamide.

10. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-9-[[(Acetyloxy)acetyl]amino]-4,7-bis (dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10, 12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide sulfate.

11. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-9-(Benzoylamino)-4,7-bis(dimethylamino)-1,4,4a, 5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthaceneca rboxamide.

12. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5 5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[(4-methoxybenzoyl)amino] -1,11-dioxo-2-naphthacenecarboxamide.

13. A compound according to claim 1, [4S-(4alpha,12aalpha))]-4,7-Bis(dimethylamino)-1,4,4a,5 5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[(2-methylbenzoyl)amino]- 1,11-dioxo-2-naphthacenecarboxamide.

14. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[(2-fluorobenzoyl)amino]-1 ,4,4a,5,5a,6,11,12a-octahydro-3, 10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide.

15. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a, 5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[(pentafluorobenzoyl)am ino]-1,11-dioxo-2-naphthacenecarboxamide hydrochloride.

16. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5, 5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[3-(trifluoro methyl)benzoyl]amino]-2-naphthacenecarboxamide.

17. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[(2-furanylcarbonyl)amino] -1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-napht hacenecarboxamide.

18. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a, 5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[(2-thienylc arbonyl)amino]-2-naphthacenecarboxamide.

19. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a, 5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[(4-nitrobenzoyl)amino] -1,11-dioxo-2-naphthacenecarboxamide.

20. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-9-[(4-Aminobenzoyl)amino]-4,7-bis-dimethylamino )-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naph thacenecarboxamidesulfate.

21. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-9-[[(4-dimethylamino)ben zoyl]amino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-di oxo-2-naphthacenecarboxamide.

22. A compound according to claim 1, [7S-(7.alpha.,10a.alpha.)]-[2-[[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5 ,5a,6,6a,7,10,10a,12-octahydro-1,8,10a, 11-tetrahydroxy-10,12-dioxo-2-naphthacenyl]amino]-2-oxoethyl]carbamic acid 1,1-dimethylethyl ester.

23. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-9-[(Aminoacetyl)amino]-4,7-bis(dimethylamino)-1 ,4,4a,5,5a,6,11,12a-octahydro-3,10,12, 12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide mono(trifluoroacetate).

24. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6, 11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[(phenylsulfonyl)am ino]-2-naphthacenecarboxamide.

25. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-9-[[(4-Chlorophenyl)sulfonyl]amino]-4,7-bis(dim ethylamino)-1,4,4a,5,5a,6,11,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarbo xamide.

26. A compound according to claim 1, [4S-(4.alpha., 12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,5, 5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[(3-nitrophenyl)sulfonyl] amino-1,11-dioxo-2-naphthacenecaboxamide.

27. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,-5a,6,11,12a-octa hydro-3,10,12,12a-tetrahydroxy-9-[[(4-nitrophenyl)sulfonyl]amino]-1,11-diox o-2-naphthacenecarboxamide.

28. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,5, 5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[(2-thienylsul fonyl)amino]-2-naphthacenecarboxamide.

29. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-9-[[(2-(Acetylamino)-4-methyl-5-thiazolylsulfon yl]amino]-4,7-bis(dimethylamino)-1,4, 4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthace necarboxamide.

30. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[(ethylsulfonyl)amino]-1,4 ,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthace necarboxamide.

31. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-9-(formylamino)-1,4,4a,5 a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-N-(1-pyrrolidinylm ethyl)-2-naphthacenecarboxamide.

32. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6, 11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[(methanesulfonyl)amino]-1,11- dioxo-2-naphthacenecarboxamide.

33. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6, 11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[(phenylmethoxy)ac etyl]amino]-2-naphthacenecarboxamide.

34. A compound according to claim 1, [7S-(7.alpha.,10a.alpha.)]-[[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5,5a ,6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthace nyl]amino]oxoacetic acid ethyl ester.

35. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a, 6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[(hydroxyacetyl)amino]-1,11- dioxo-2-naphthacenecarboxamide.

36. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-9-[[(methylamino)acetyl] amino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2 -naphthacenecarboxamide hydrochloride.

37. A compound according to claim 1, [7S-(7.alpha.,10a.alpha.)]-[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5,5a, 6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacen yl]carbamic acid methyl ester.

38. A compound according to claim 1, [7S-(7.alpha.,10a.alpha.)]-[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5,5a, 6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacen yl]carbamic acid (2-diethylamino)ethyl ester.

39. A compound according to claim 1, [7S-(7.alpha.,10a.alpha.)]-[9-(Aminocarbonyl)-4,7-bis(dimethyl-amino)-5,5a ,6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthace nyl]carbamic acid ethenyl ester.

40. A compound according to claim 1, [7S-(7.alpha.,10a.alpha.)]-[9-(Aminocarbonyl)-4,7-bis(dimethyl-amino)-5,5a ,6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthace nyl]carbamic acid 2-propenyl ester.

41. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-9-[[(dimethylamino)acety l]amino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo -2-naphthacenecarboxamide sulfate.

42. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6, 11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[(methoxyacetyl)amino]-1,11-di oxo-2-naphthacenecarboxamide hydrochloride.

43. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-9-[(4-Bromo-1-oxobutyl)amino]-4,7-bis(dimethyla mino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2- naphthacenecarboxamide sulfate.

44. A compound according to claim 1 [4S-(4.alpha.,12a.alpha.)]-9-[[(Acetyloxy)acetyl]amino]-4,7-bis (dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10, 12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide.

45. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-9-(Benzoylamino)-4,7-bis(dimethylamino)-1,4,4a, 5,5a,6,11,12a-octahydro-3,10,12,12a-tetra-hydroxy-1,11-dioxo-2-naphthacenec arboxamide sulfate.

46. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5, 5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[3-(trifluoro methyl)benzoyl]amino]-2-naphthacenecarboxamide hydrochloride.

47. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-9-[(4-Aminobenzoyl)amino]-4,7-bis(dimethylamino )-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12, 12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide.

48. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-9-[[(4-dimethylamino)ben zoyl]amino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-di oxo-2-naphthacenecarboxamide hydrochloride.

49. A compound according to claim 1, [7S-(7.alpha.,10a.alpha.)]-[2-[[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5 ,5a,6,6a,7,10,10a,12-octahydro-1,8,10a, 11-tetrahydroxy-10,12-dioxo-2-naphthacenyl]amino]-2-oxoethyl]carbamic acid 1,1-dimethylethyl ester hydrochloride.

50. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-9-[(Aminoacetyl)amino]-4,7-bis(dimethylamino)-1 ,4,4a,5,5a,6,11,12a-octahydro-3,10,12, 12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide.

51. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[(ethylsulfonyl)amino]-1,4 ,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthace necarboxamide hydrochloride.

52. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6, 11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[(methanesulfonyl)amino]-1,11- dioxo-2-naphthacenecarboxamide sulfate.

53. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6, 11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[(phenylmethoxy)ac etyl]amino]-2-naphthacenecarboxamide hydrochloride.

54. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a, 6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[(hydroxyacetyl)amino]-1,11- dioxo-2-naphthacenecarboxamide sulfate.

55. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-9-[[(dimethylamino)acety l]amino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo -2-naphthacenecarboxamide.

56. A compound according to claim 1, [7S-(7.alpha.,10a.alpha.)]-[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5,5a, 6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacen yl]carbamic acid methyl ester sulfate.

57. A compound according to claim 1, [7S-(7.alpha.,10a.alpha.)]-[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5,5a, 6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacen yl]carbamic acid (2-diethylamino)ethyl ester hydrochloride.

58. A compound according to claim 1, [7S-(7.alpha.,10a.alpha.)]-[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5,5a, 6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacen yl]carbamic acid ethenyl ester sulfate.

59. A compound according to claim 1, [7S-(7.alpha.,10a.alpha.)]-[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5,5a, 6,6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacen yl]carbamic acid 2-propenyl ester hydrochloride.

60. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.]-4,7-Bis(dimethylamino)-9-[[(diethylamino) acetyl]amino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12, 12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide sulfate.

61. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.]-4,7-Bis(dimethylamino)-9-[[(diethylamino) acetyl]amino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12, 12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide hydrochloride.

62. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.]-4,7-Bis(dimethylamino)-9-[[(diethylamino) acetyl]amino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12, 12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide.

63. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[(dimethylamino)acetyl]am ino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-n aphthacenecarboxamide dihydrochloride.

64. A compound according to claim 1, [4S-(4.alpha.,12a.alpha.)]-4,7-Bis(dimethylamino)-9-(chloroacetylamino)-1, 4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthac enecarboxamide.

65. A compound according to claim 1, [4S-(4alpha,12aalpha)]-9-[(Chloroacetyl)amino]-4,7-bis(dimethylamino)-1,4, 4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacen ecarboxamide dihydrochloride.

66. A compound according to claim 1, [4S-(4alpha,12aalpha)]-9-[(Bromoacetyl)amino]-4,7-bis(dimethylamino)-1,4,4 a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacene carboxamide dihydrochloride.

67. A compound according to claim 1, [4S-(4alpha,12aalpha)]-9-[(Bromoacetyl)amino]-4,7-bis(dimethylamino)-1,4,4 a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacene carboxamide (free base).

68. A compound according to claim 1, [4S-(4alpha,12aalpha)]-9-[(Bromoacetyl)amino]-4,7-bis(dimethylamino)-1,4,4 a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacene carboxamide monohydrobromide.

69. A compound according to claim 1, [4S-(4alpha,12aalpha)]-9-[(2-Bromo-1-oxopropyl)amino]-4,7-bis(dimethylamin o)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-nap hthacenecarboxamide hydrobromide.

70. A compound according to claim 1, [4S-(4alpha,12aalpha)]-9-[(2-Bromo-1-oxopropyl)amino]-4,7-bis(dimethylamin o)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-nap hthacenecarboxamide hydrobromide.

71. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahyd ro-3,10,12,12a-tetrahydroxy-9-[[(methylamino)acetyl]amino]-1,11-dioxo-2-nap hthacenecarboxamide dihydrochloride.

72. A compound according to claim 1, [7S-(7alpha,10aalpha)]-N-[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5,5a,6, 6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl ]-4-morpholineacetamide dihydrochloride.

73. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[(ethylamino)acetyl]amino ]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naph thacenecarboxamide dihydrochloride.

74. A compound according to claim 1, [4S-(4alpha,12aalpha)]-9-[[(Cyclopropylamino)acetyl]amino]-4,7-bis(dimethy lamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo- 2-naphthacenecarboxamide dihydrochloride.

75. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[(butylamino)acetyl]amino ]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naph thacenecarboxamide dihydrochloride.

76. A compound according to claim 1, [4S-(4alpha,12aalpha)]-9-[[(Diethylamino)acetyl]amino]-4,7-bis(dimethylami no)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-na phthacenecarboxamide dihydrochloride.

77. A compound according to claim 1, [7S-(7alpha,10aalpha)]-N-[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5,5a,6, 6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl ]-1-pyrrolidineacetamide dihydrochloride.

78. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahyd ro-3,10,12,12a-tetrahydroxy-9-[[[(2-methylpropyl)amino]acetyl]amino]-1,11-d ioxo-2-naphthacenecarboxamide dihydrochloride.

79. A compound according to claim 1, [7S-(7alpha,10aalpha)]-N-[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5,5a,6, 6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl ]-1-piperidineacetamide dihydrochloride.

80. A compound according to claim 1, [7S-(7alpha,10aalpha)]-N-[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5,5a,6, 6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl ]-1H-imidazole-1-acetamide dihydrochloride.

81. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahyd ro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[(propylamino)acetyl]amino]-2-nap hthacenecarboxamide dihydrochloride.

82. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[dimethylamino)acetyl]ami no]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-na phthacenecarboxamide.

83. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[(hexylamino)acetyl]amino ]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naph thacenecarboxamide dihydrochloride.

84. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[2-(dimethylamino)-1-oxop ropyl]amino]-1,4,4a,5,5a,6,11, 12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-napthacenecarboxamide dihydrochloride.

85. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a, 5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[[2-(methylamino)-1-oxo propyl]amino]-1,11-dioxo-2-naphthacenecarboxamide dihydrochloride.

86. A compound according to claim 1, [7S-(7alpha,10aalpha)]-N-[9-(Aminocarbonyl)-4,7-bis(dimethylamino)-5,5a,6, 6a,7,10,10a,12-octahydro-1,8,10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl ]-alphamethyl-1-pyrrolidineacetamide dihydrochloride.

87. A compound according to claim 1 [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[4-(dimethylamino)-1-oxob utyl]amino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-di oxo-2-napthacenecarboxamide dihydrochloride.

88. A compound according to claim 1, [4S-(4alpha,12aalpha)]-9-[[(Butylmethylamino)acetyl]amino]-4,7-bis(dimethy lamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo- 2-naphthacenecenecarboxamide dihydrochloride

89. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahyd ro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[(pentylamino)acetyl]amino]-2-nap hthacenecarboxamide dihydrochloride.

90. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahyd ro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[[(phenylmethyl)amino]acetyl]amin o]-2-naphthacenecarboxamide dihydrochloride.

91. A compound according to claim 1, [7S-(7alpha, 10aalpha) ]-N-[2-[[9-(Aminocarbonyl) -4,7-bis(dimethylamino)-5,5a,6,6a,7,10a,12-octahydro-1,8, 10a,11-tetrahydroxy-10,12-dioxo-2-naphthacenyl]amino]-2-oxoethyl]glycine.

92. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[(dimethylamino)acetyl]am ino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-N-( 1-pyrrolidinylmethyl)-2-naphthacenecarboxamide.

93. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[(dimethylamino)acetyl]am ino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-N-( 4-morpholinylmethyl)-2-naphthacenecarboxamide.

94. A compound according to claim 1, [4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[(dimethylamino)acetyl]am ino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-N-( 1-piperidinylmethyl)-2-naphthacenecarboxamide.

95. A compound according to claim 1, [7S-(7alpha,10aalpha)]-N-[9-(Aminocarbonyl-4,7-bis(dimethylamino)-5,5a,6,6 a,7,10,10a,12-octahydro-1,8, 10a,11-tetrahydroxy-10,12-dioxo-2-napthacenyl]-1-azetidineacetamide.

96. A compound according to claim 1, [4S-(4alpha,12aalpha)]-9-[[(Cyclobutylamino)acetyl]amino]-4,7-bis(dimethyl amino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2 -naphthacenecarboxamide hydrochloride.

97. A pharmaceutical composition of matter comprising a compound according to claim 1 in association with a pharmaceutically acceptable carrier.

98. A veterinary composition which comprises a pharmacologically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.

Make Better Decisions: Try a trial or see plans & pricing

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.