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US 7,056,902 B2Granted
4-dedimethylamino tetracycline compounds
AssigneeParatek Pharmaceuticals, Inc.
InventorsMark L. Nelson, Kwasi Ohemeng
Life of this patent
Estimating the term…
Abstract
The present invention pertains, at least in part, to novel substituted 4-dedimethylamino tetracycline compounds. These tetracycline compounds can be used to treat numerous tetracycline compound-responsive states, such as bacterial infections and neoplasms, as well as other known applications for minocycline and tetracycline compounds in general, such as blocking tetracycline efflux and modulation of gene expression.
Claims12
A tetracycline compound of formula IV:
- wherein:
- X is CHC(R13Y′Y), or CR6′R6;
- R2 is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, arylalkyl, aryl, heterocyclic or heteroaromatic;
- R7′ and R7″ are each alkyl;
- R4 and R4′ are each independently alkyl, alkenyl, alkynyl, aryl, hydroxyl, alkoxy, halogen, hydrogen, or taken together to form the oxygen of a carbonyl;
- R2′, R3, R10, R11 and R12 are each hydrogen;
- R5 is hydroxyl hydrogen, thiol, alkanoyl, aroyl, alkaroyl, aryl, heteroaromatic, alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, arylalkyl, alkyl carbonyloxy, or aryl carbonyloxy;
- R6 and R6′ are independently hydrogen, methylene, hydroxyl, halogen, thiol, alkyl, alkenyl, alkynyl, aryl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, or an arylalkyl;
- R7 is NR7′R7″;
- R9 is alkyl, alkenyl, alkynyl, aryl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, arylalkyl, amido, acyl, arylalkenyl, arylalkynyl, thionitroso, or —(CH2)0-3NR9cC(=Z′)ZR9a;
- Z is CR9dR9e, S, NR9b or O;
- Z′ is NR9f, O or S;
- R9a, R9b, R9c, R9d, R9e and R9f are each independently hydrogen, acyl, alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, arylalkyl, aryl, heterocyclic or heteroaromatic;
- R8 is hydrogen, hydroxyl, thiol, alkyl, alkenyl, alkynyl, aryl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, or an arylalkyl;
- R13 is hydrogen, hydroxyl, alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, or an arylalkyl;
- Y′ and Y are each independently hydrogen, halogen, hydroxyl, cyano, sulfhydryl, amino, alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, or an arylalkyl, and pharmaceutically acceptable salts, esters and amides thereof.
13 more elements
A substituted tetracycline compound selected from the group consisting of:
- and pharmaceutically acceptable salts, esters and amides thereof.
Dependencies are inferred from the claim text.