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US 2003/0125389 A1Published application
Beta-amino acid derivatives useful for the treatment of bacterial infections
OwnerBore G. Raju, Sampathkumar Anandan +4inventors
InventorsBore G. Raju, Sampathkumar Anandan, Joaquim Trias, Prudencio S. Herradura, Kathleen H. Mortell, Dinesh V. Patel
Life of this patent
Estimating the term…
Abstract
The invention provides compounds that are useful for the treatment of bacterial infections in mammals. More specifically, it is directed to beta-amino acid derivatives or pharmaceutically acceptable salts, prodrugs, or isomers of 1 those compounds that are useful for the treatment of such infections.
Claims30
A compound of formula (I):
- 21
- wherein the substituents are as described below.
- R1 is —NHR18;
- R2 is H, alkyl or R2 and either R4 or R5 together with the atoms to which they are attached form a cyclic alkyl group, or R2 and R6 together with the atoms to which they are attached form a cyclic alkyl group, an aryl group or a heteroaryl group, or R2 and R8 together with the atoms to which they are attached form a cyclic heteroalkyl group;
- R3 is H, alkyl or R3 and R10 together with the atoms to which they are attached form a cyclic alkyl group;
- R4 is H, alkyl or R4 and R6 together with the atoms to which they are attached form a cyclic alkyl group, or R4 and R8 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R4 and R10 together with the atoms to which they are attached form a cyclic alkyl group;
- R5 is H, F, Cl , OR16, SR16 or S(O)nR17, or R5 and R6 together with the atoms to which they are attached form a cyclic alkyl group, or R5 and R8 together with the atoms to which they are attached form a cyclic heteroalkyl group;
- R6 is H, alkyl or R6 and R2 together with the atoms to which they are attached form a cyclic alkyl group, an aryl group or a heteroaryl group, or R6 and R4 together with the atoms to which they are attached form a cyclic alkyl group, or R6 and R5 together with the atoms to which they are attached form a cyclic alkyl group;
- R7 is H, alkyl or R7 and R10 together with the atoms to which they are attached form a cyclic alkyl group;
- R8 is H, alkyl, or R8 and R2 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R8 and R4 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R8 and R5 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R8 and R6 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R8 and R11 together with the atoms to which they are attached form a cyclic heteroalkyl group;
- R9 is H or alkyl;
- R10 is H or alkyl, or R10 and R3 together with the atoms to which they are attached form a cyclic alkyl group, or R10 and R4 together with the atoms to which they are attached form a cyclic alkyl group, or R10 and R7 together with the atoms to which they are attached form a cyclic alkyl group, or R10 and R11 together with the atoms to which they are attached form a cyclic alkyl group;
- R11 is H, alkyl, OH, SH or F, or R11 and R8 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R11 and R10 together with the atoms to which they are attached form a cyclic alkyl group;
- R12 is H or alkyl;
- R13 is H or alkyl when X is N;
- R13 is not a substituent when X is O;
- R14 is —CHR15—CO2H, —C6H4—CO2H, —C4H3N—CO2H, —C4H2S—CO2H, C4H2O—CO2H, —CH R15—S(O)2OH, —CH R15—S(O)2—NH2 or —CH R15—P(O)(CH3)OH;
- and
- R15 is H or alkyl;
- R16 is H or alkyl;
- R17 is alkyl or aryl;
- R18 is H, CH3 or CH2CH3;
- and,
- n is 1 or 2;
- with the proviso that the compound of formula (I) is neither negamycin nor deoxynegamycin.
22 more elements
A compound selected from a group consisting of the following compounds:
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A method of treating a bacterial infection in a mammal, wherein the method comprises administering a compound of formula (I) to the mammal:
- 23
- wherein,
- R1 is —NHR18;
- R2 is H, alkyl or R2 and either R4 or R5 together with the atoms to which they are attached form a cyclic alkyl group, or R2 and R6 together with the atoms to which they are attached form a cyclic alkyl group, an aryl group or a heteroaryl group, or R2 and R8 together with the atoms to which they are attached form a cyclic heteroalkyl group;
- R3 is H, alkyl or R3 and R10 together with the atoms to which they are attached form a cyclic alkyl group;
- R4 is H, alkyl or R4 and R6 together with the atoms to which they are attached form a cyclic alkyl group, or R4 and R8 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R4 and R10 together with the atoms to which they are attached form a cyclic alkyl group;
- R5 is H, F, Cl , OR16, SR16 or S(O)nR17, or R5 and R6 together with the atoms to which they are attached form a cyclic alkyl group, or R5 and R8 together with the atoms to which they are attached form a cyclic heteroalkyl group;
- R6 is H, alkyl or R6 and R2 together with the atoms to which they are attached form a cyclic alkyl group, an aryl group or a heteroaryl group, or R6 and R4 together with the atoms to which they are attached form a cyclic alkyl group, or R6 and R5 together with the atoms to which they are attached form a cyclic alkyl group;
- R7 is H, alkyl or R7 and R10 together with the atoms to which they are attached form a cyclic alkyl group;
- R8 is H, alkyl, or R8 and R2 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R8 and R4 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R8 and R5 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R8 and R6 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R8 and R11 together with the atoms to which they are attached form a cyclic heteroalkyl group;
- R9 is H or alkyl;
- R10 is H or alkyl, or R10 and R3 together with the atoms to which they are attached form a cyclic alkyl group, or R10 and R4 together with the atoms to which they are attached form a cyclic alkyl group, or R10 and R7 together with the atoms to which they are attached form a cyclic alkyl group, or R10 and R11 together with the atoms to which they are attached form a cyclic alkyl group;
- R11 is H, alkyl, OH, SH or F, or R11 and R8 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R11 and R10 together with the atoms to which they are attached form a cyclic alkyl group;
- R12 is H or alkyl;
- R13 is H or alkyl when X is N;
- R13 is not a substituent when X is O;
- R14 is —CHR15—CO2H, —C6H4—CO2H, —C4H3N—CO2H, —C4H2S—CO2H, C4H2O—CO2H, —CH R15—S(O)2OH, —CH R15—S(O)2—NH2 or —CH R15—P(O)(CH3)OH;
- and
- R15 is H or alkyl;
- R16 is H or alkyl;
- R17 is alkyl or aryl;
- R18 is H, CH3 or CH2CH3;
- and,
- n is 1 or 2;
- with the proviso that the compound of formula (I) is neither negamycin nor deoxynegamycin.
22 more elements
A method of treating a bacterial infection in a mammal, wherein the method comprises administering a compound to the mammal, and wherein the compound is selected from a group consisting of the following compounds:
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A pharmaceutical composition, wherein the composition comprises a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of formula (I):
- wherein,
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- R1 is —NHR18;
- R2 is H, alkyl or R2 and either R4 or R5 together with the atoms to which they are attached form a cyclic alkyl group, or R2 and R6 together with the atoms to which they are attached form a cyclic alkyl group, an aryl group or a heteroaryl group, or R2 and R8 together with the atoms to which they are attached form a cyclic heteroalkyl group;
- R3 is H, alkyl or R3 and R10 together with the atoms to which they are attached form a cyclic alkyl group;
- R4 is H, alkyl or R4 and R6 together with the atoms to which they are attached form a cyclic alkyl group, or R4 and R8 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R4 and R10 together with the atoms to which they are attached form a cyclic alkyl group;
- R5 is H, F, Cl , OR16, SR16 or S(O)nR17, or R5 and R6 together with the atoms to which they are attached form a cyclic alkyl group, or R5 and R8 together with the atoms to which they are attached form a cyclic heteroalkyl group;
- R6 is H, alkyl or R6 and R2 together with the atoms to which they are attached form a cyclic alkyl group, an aryl group or a heteroaryl group, or R6 and R4 together with the atoms to which they are attached form a cyclic alkyl group, or R6 and R5 together with the atoms to which they are attached form a cyclic alkyl group;
- R7 is H, alkyl or R7 and R10 together with the atoms to which they are attached form a cyclic alkyl group;
- R8 is H, alkyl, or R8 and R2 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R8 and R4 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R8 and R5 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R8 and R6 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R8 and R11 together with the atoms to which they are attached form a cyclic heteroalkyl group;
- R9 is H or alkyl;
- R10 is H or alkyl, or R10 and R3 together with the atoms to which they are attached form a cyclic alkyl group, or R10 and R4 together with the atoms to which they are attached form a cyclic alkyl group, or R10 and R7 together with the atoms to which they are attached form a cyclic alkyl group, or R10 and R11 together with the atoms to which they are attached form a cyclic alkyl group;
- R11 is H, alkyl, OH, SH or F, or R11 and R8 together with the atoms to which they are attached form a cyclic heteroalkyl group, or R11 and R10 together with the atoms to which they are attached form a cyclic alkyl group;
- R12 is H or alkyl;
- R13 is H or alkyl when X is N;
- R13 is not a substituent when X is O;
- R14 is —CHR15—CO2H, —C6H4—CO2H, —C4H3N—CO2H, —C4H2S—CO2H, C4H2O—CO2H, —CH R15—S(O)2OH, —CH R15—S(O)2—NH2 or —CH R15—P(O)(CH3)OH;
- and
- R15 is H or alkyl;
- R16 is H or alkyl;
- R17 is alkyl or aryl;
- R18 is H, CH3 or CH2CH3;
- and,
- n is 1 or 2;
- with the proviso that the compound of formula (I) is neither negamycin nor deoxynegamycin.
22 more elements
A pharmaceutical composition, wherein the composition comprises a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound, and wherein the compound is selected from the group consisting of the following compounds:
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Dependencies are inferred from the claim text.