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US 5,326,759 AGranted
9-amino-7-(substituted)-6-demethyl-6-deoxytetracyclines
AssigneeAmerican Cyanamid Company
InventorsJoseph J. Hlavka, Phaik-Eng Sum, Yakov Gluzman, Ving J. Lee
Life of this patent
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Abstract
Novel 9-amino-7-(substituted amino)-6-demethyl-6-deoxytetracyclines having activity against a wide spectrum of organisms including organisms which are resistant to tetracyclines are disclosed. Also disclosed are intermediates and methods for making the novel compounds of the present invention.
Claims18
A compound of the formula:
- ##STR16## wherein:
- R=NR.sub.1 R.sub.2,
- and when R.sub.1 =hydrogen, R.sub.2 =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;
- and when R.sub.1 =methyl or ethyl, R.sub.2 =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl;
- and when R.sub.1 =n-propyl, R.sub.2 =n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl;
- and when R.sub.1 =1-methylethyl, R.sub.2 =n-butyl, 1-methylpropyl or 2-methylpropyl;
- and when R.sub.1 =n-butyl, R.sub.2 =n-butyl, 1-methylpropyl or 2-methylpropyl;
- and when R.sub.1 =1-methylethyl, R.sub.2 =2-methylpropyl;
- R.sub.3 is selected from (C.sub.7 -C.sub.9)aralkyl group;
- a heterocycle group selected from 2 or 3-furanyl, 2 or 3-thienyl, 2,3 or 4-pyridyl, di(C.sub.1 -C.sub.3)alkyl substituted pyridyl, benzofuranyl, benzothienyl, quinolinyl;
- R.sub.4 is selected from hydrogen;
- straight or branched (C.sub.1 -C.sub.3)alkyl group;
- (C.sub.6 -C.sub.10)aryl group;
- (C.sub.7 -C.sub.9)aralkyl group;
- a heterocycle group selected from 2 or 3-furanyl, 2 or 3-thienyl, 2,3 or 4-pyridyl, di(C.sub.1 -C.sub.3)-alkyl substituted pyridyl, benzofuranyl, benzothienyl, quinolinyl or --(CH.sub.2).sub.n when n=1-4 and R.sub.6 is selected from hydrogen;
- straight or branched (C.sub.1 -C.sub.3)alkyl;
- or (C.sub.6 -C.sub.10)aryl;
- or R.sub.3 and R.sub.4 taken together are--(CH.sub.2).sub.2 W(CH.sub.2)--.sub.2, wherein W is selected from (CH.sub.2).sub.n and n=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 and metal complexes.
16 more elements
A compound of the formula:
- ##STR17## wherein:
- R=NR.sub.1 R.sub.2,
- and when R.sub.1 =hydrogen, R.sub.2 =methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;
- and when R.sub.1 =methyl or ethyl, R.sub.2 =methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl;
- and when R.sub.1 =n-propyl, R.sub.2 =n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl or 2-methylpropyl;
- and when R.sub.1 =1-methylethyl, R.sub.2 =n-butyl, 1-methylpropyl or 2-methylpropyl;
- and when R.sub.1 =n-butyl, R.sub.2 =n-butyl, 1-methylpropyl or 2-methylpropyl;
- and when R.sub.1 =1-methylpropyl, R.sub.2 =2-methylpropyl;
- R.sub.3 is selected from a heterocycle group selected from 2 or 3-furanyl, 2 or 3-thienyl, 2,3 or 4-pyridyl, di(C.sub.1 -C.sub.3)-alkyl substituted pyridyl, benzofuranyl, benzothienyl, quinolinyl;
- R.sub.4 is selected from hydrogen;
- straight or branched (C.sub.1 -C.sub.3)alkyl group;
- (C.sub.6 -C.sub.10)aryl group;
- (C.sub.7 -C.sub.9)aralkyl group;
- a heterocycle group selected from 2 or 3-furanyl, 2 or 3-thienyl, 2,3 or 4-pyridyl, di(C.sub.1 -C.sub.3) -alkyl substituted pyridyl, benzofuranyl, benzothienyl, quinolinyl or --(CH.sub.2).sub.n COOR.sub.6 when n=1-4 and R.sub.6 is selected from hydrogen;
- straight or branched (C.sub.1 -C.sub.3)alkyl;
- or (C.sub.6 -C.sub.10)aryl;
- or R.sub.3 and R.sub.4 taken together are --(CH.sub.2).sub.2 W(CH.sub.2)--.sub.2, wherein W is selected from (CH.sub.2).sub.n and n=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 and metal complexes.
15 more elements
Dependencies are inferred from the claim text.