9-substituted minocycline compounds
AssigneesParatek Pharmaceuticals, Inc., Trustees of Tufts College
InventorsMark L. Nelson, Roger Frechette, Peter Viski, Beena Bhatia
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Abstract
The present invention pertains, at least in part, to novel 9-substituted minocycline compounds. These minocycline 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.
Claims34
A minocycline compound of formula I:
- wherein:
- X is CHC(R13Y′Y), CR6′R6, S, NR6, or O;
- R2, R4′, R4″, R7′ and R7″ are each hydrogen, altyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, arylalkyl, aryl, heterocyclic, heteroaromatic or a prodrug moiety;
- R4 is NR4′R4″, alkyl, alkenyl, alkynyl, aryl, hydroxyl, halogen, or hydrogen;
- R2′, R3, R10, R11 and R12 are each hydrogen or a pro-drug moiety;
- 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, absent, hydroxyl, halogen, thiol, alkyl, alkenyl, alkynyl, aryl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, or an arylalkyl;
- R9 is alkynyl substituted with an alkyl group;
- R8 is hydrogen, hydroxyl, halogen, thiol, alkyl, alkenyl, alkynyl, aryl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, or an arylalkyl;
- R13 is hydrogen, hydroxy, 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 prodrugs thereof.
A minocycline compound or a pharmaceutically acceptable salt thereof of the formula:
A 9-substituted minocycline compound of the formula:
- wherein:
- R4′, R4″, R7′, and R7″ are alkyl;
- and
- R9 is an alkynyl group, wherein said alkynyl group is substituted with an alkyl group pharmaceutically acceptable salts thereof.
The method of claim 78, wherein said bacterial infection is associated with E. coli, S. aureus, or E. faecalis.
Dependencies are inferred from the claim text.