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US 6,310,058 B1Granted
Antimycobacterial agents
AssigneeUniversity of Notre Dame du Lac
InventorsMarvin J. Miller, Yanping Xu
Life of this patent
Estimating the term…
Abstract
Compounds represented by the formula [1] R1 is H or a substituent; R2 and R3 are C1-C3 alkyl; R4 is siderophore group e.g. CH3—(CH2)n—C(O)—N(OH)—(CH2)m— with n=10-22, m=2-6; X is O, S, or NH; X1 is O or NH; Y is H or alkyl; Z is H or substituted amino, e.g., t-BocNH or CbzNH, and r is 2-4; are useful in the method provided for treating tuberculosis. [1] is prepared by coupling [7], wherein HX1 is HO— or H2N—, with [4] obtained as the free acid after saponification of the methyl ester.
Claims16
The compound of the formula
- wherein R is a 2-phenyloxazoline of the formula (1a)
- or a 2-phenyloxazole of the formula (1b)
- wherein R1 is hydrogen, lower alkyl, lower alkoxy, hydroxy, carboxy, amino, mono- or dialkylamino, aminocarbonyl, mono- or dialkylaminocarbonyl, or C1-C4 alkyl substituted by one or two phenyl groups;
- R2 and R3 independently are hydrogen or C1-C3 alkyl;
- p and q independently are 0, 1 or 3;
- R4 is a siderophoric group of the formula
- —(CH2)m—N(OH)—C(O)—(CH2)n—(CH═CH)o—CH3
- wherein m is an integer of from 2 to 6, n is 0 or an integer of from 1 to 22, and o is 0 or an integer 1 to 4, provided that m+o is no greater than 25;
- X1 is O or NH;
- Y is H or C1-C4 alkyl;
- Z is H, lower alkyl, mono- or dialkylamino, or —N(R5)(R5′) when X1 is NH;
- and when X1 is
- O, Z is mono- or dialkylamino or —NR5)(R5′);
- wherein R5 is hydrogen, lower alkyl, alkyloxycarbonyl, aryloxycarbonyl,
- aralkyloxycarbonyl, cycloalkoxycarbonyl, bicycloalkyloxycarbonyl, or lower alkanoyl;
- R5′ is hydrogen or lower alkyl;
- or the pharmaceutically acceptable salts thereof.
14 more elements
Dependencies are inferred from the claim text.