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US 7,547,692 B2Granted
Rifamycin analogs and uses thereof
AssigneeActivBiotics Pharma, LLC
InventorsJohn H. van Duzer, Arthur F. Michaelis, William B. Geiss, Douglas G. Stafford, Joseph Raker, Xiang Y. Yu, James M. Siedlecki, Yingfei Yang
Life of this patent
Estimating the term…
Abstract
The present invention features rifamycin analogs and methods of using these compounds to treat a variety of microbial infections.
Claims18
A compound having the formula:
- or a pharmaceutically acceptable salt thereof, wherein
- (a) A is H, OH, O—(C1-6 alkyl), O—(C1-4 alkaryl), O—(C6-12 aryl), O—(C1-9 heteroaryl), or O—(C1-4 alkheteroaryl);
- W is O, S, or NR1, wherein R1 is H, C1-6 alkyl, C1-4 alkaryl, or C1-4 alkheteroaryl;
- X is H or COR2, wherein R2 is C1-6 alkyl, which can be substituted with 1-5 OH groups, O—(C3-7 alkyl), which can be substituted with 1-4 OH groups, C6-12 aryl, C1-4 alkaryl, C1-9 heteroaryl, or C1-4 alkheteroaryl, wherein each alkyl carbon is bonded to no more than one oxygen atom;
- Y is H, Hal, or ORY3, wherein RY3 is C1-6 alkyl, C6-12 aryl, C1-4 alkaryl, C1-9 heteroaryl, or C1-4 alkheteroaryl;
- Z is H, Hal, or ORZ3 wherein RZ3 is C1-6 alkyl, C6-12 aryl, C1-4 alkaryl, C1-9 heteroaryl, or C1-4 alkheteroaryl;
- and
- R4 has the formula:
- wherein
- R5 is H, C1-6 alkyl, C1-4 alkaryl, C1-4 alkheteroaryl, COR10, CO2R11, CONR10R11 CSR10, COSR11, CSOR10, CSNR10R11, SO2R11, or SO2NR10R11, wherein R10 is H, C1-6 alkyl, C6-12 aryl, C1-4 alkaryl, C1-9 heteroaryl, or C1-4 alkheteroaryl, R11 is H, C1-6 alkyl, C6-12 aryl, C1-4 alkaryl, C1-9 heteroaryl, or C1-4 alkheteroaryl, or R10 and R11 together form a C2-6 linkage, optionally containing a non-vicinal O;
- R6 is H, C1-6 alkyl, C1-4 alkaryl, C1-4 alkheteroaryl;
- R7 is H, C1-6 alkyl, C6-12 aryl, C1-9 heteroaryl, C2-9 heterocyclyl, C1-4 alkaryl, C1-4 alkheteroaryl, OR12, or NR12R13, wherein R12 is H, C1-6 alkyl, C6-12 aryl, C1-4 alkaryl, C1-9 heteroaryl, or C1-4 alkheteroaryl, R13 is C1-6 alkyl, C6-12 aryl, C1-4 alkaryl, C1-9 heteroaryl, or C1-4 alkheteroaryl, or R12 and R13 together from a C2-6 linkage, optionally containing a non-vicinal O;
- T is O, S, NR5, or a bond;
- each of R8 and R9 is, independently H, C1-6 alkyl, C6-12 aryl, C1-9 heteroaryl, C2-9 heterocyclyl, C1-4 alkaryl, or C1-4 alkheteroaryl, or R8 and R5 together form a 3-8-membered ring, with the ring optionally containing a non-vicinal oxygen;
- and each of r and s is, independently, 1 or 2,
- wherein said C1-9 heteroaryl is selected from the group consisting of furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, oxatriazolyl, pyridyl, pyridazyl, pyrimidyl, pyrazyl, triazyl, benzofuranyl, isobenzofuranyl, benzothienyl, indole, indazolyl, indolizinyl, benzisoxazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, naphtyridinyl, phthalazinyl, phenanthrolinyl, purinyl, and carbazolyl, and
- wherein,
- when W is O or NR1, T is a bond, R8 and R9 are H, and X is COR2, R4 is not
- and
- when W is O, and X is COR2, R4 is not
17 more elements
A compound selected from the group consisting of:
Dependencies are inferred from the claim text.