Spectinamides as anti-tuberculosis agents
AssigneeUniversity of Tennessee Research Foundation
InventorsRichard E. Lee, Jianjun Qi, Julian G. Hurdle, Bernd Meibohm, VNR Pavan Kumar Vaddady, Rakesh, Jiuyu Liu
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Abstract
Novel 3′-deoxy-3′-acylaminospectinomycin compounds are described. Also described are methods of using the 3′-deoxy-3-acylaminospectinomycin compounds and other spectinomycin analogs in treating tuberculosis and in treating microbial infections.
Claims45
A method of treating a Mycobacterial infection in a subject in need of treatment thereof, the method comprising administering to the subject an effective amount of a compound of Formula (I):
- wherein:
- R1 and R2 are each independently H, alkoxycarbonyl, or aralkoxycarbonyl;
- R3 is alkyl;
- R4 is H, hydroxy, alkyl, or alkoxy;
- and
- R5 is —C(═O)R6, wherein R6 is:
- (a) selected from the group consisting of —CH2NHC(CH3)3,
- —CH(NH2)CH(CH3)CH2CH3, —CH(NH2)CH(CH3)2,
- —CH(CH2C6H5)NHC(═O)CH2NH2, —CH2CH2NHC(═O)C6H5, and
- —CH2CH2NHC(═O)CH2C6H5;
- or
- (b) selected from the group consisting of heteroaryl, substituted heteroaryl, 2-substituted phenyl, 4-halo-substituted phenyl, —CH2R7, and —C(R8)2;
- wherein R7 is selected from the group consisting of aralkyl, substituted aralkyl, heteroaryl, substituted heteroaryl, and substituted phenyl, wherein said substituted phenyl is selected from the group consisting of fluoro-substituted phenyl, alkyl-substituted phenyl, 2-substituted phenyl, 3-mono-substituted phenyl, 2,3-di-substituted phenyl, and di-substituted phenyl wherein two phenyl carbons are together substituted with an alkylene;
- and each R8 is independently aryl or substituted aryl;
- or a pharmaceutically acceptable salt thereof.
A method of treating tuberculosis in a subject in need of treatment thereof, the method comprising administering to the subject an effective amount of a compound of Formula (I):
- wherein:
- R1 and R2 are each independently H, alkoxycarbonyl, or aralkoxycarbonyl;
- R3 is alkyl;
- R4 is H, hydroxy, alkyl, or alkoxy;
- and
- R5 is selected from the group consisting of alkyl, substituted alkyl, aralkyl, substituted aralkyl, aryl, substituted aryl, and acyl;
- or a pharmaceutically acceptable salt thereof.
A method of treating a Mycobacterial infection in a subject in need of treatment thereof, wherein the method comprises administering to the subject an effective amount of a compound selected from the group consisting of:
- 3′-dihydro-3′-deoxy-4(R)-cyclopropylmethylamino spectinomycin;
- 3′-dihydro-3′-deoxy-4(R)-furan-2-yl-methylamino spectinomycin;
- 3′-dihydro-3′-deoxy-4(R)-(3methoxy)benzylamino spectinomycin;
- 3′ -dihydro-3′ -deoxy-4(R)-(4-fluoro)benzylamino spectinomycin;
- and
- 3′ -dihydro-3′ -deoxy-4(R)-2-phenylethylamino spectinomycin;
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.