Antimicrobial Peptidomimetics
AssigneeAgency for Science, Technology and Research
InventorBrian Cheng San CHIA
Life of this patent
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Abstract
The present invention relates to peptidomimetics of the formula (I) or (I)c wherein L1, L2, L3, R1, R2, R3, R4, R5, R6, n, m, Q, X, Z1 and Z2 are defined as mentioned in the description and to salts and solvates of each of these compounds and to processes for the preparation thereof, compositions containing them and the uses of such compounds. It has been found that the compounds have a high microbicide activity and are suited to combat resistant bacteria, such as meticillin-resistant Staphylococcus aureus (MRSA) strains, at very low concentrations.
Claims13
A compound of the formula (I) or (Ic):
- wherein
- L1 represents —CO—, alkandiyl, -alkyl-CO— or —CO-alkyl-;
- L2 represents —CO—, alkandiyl, -alkyl-CO— or —CO-alkyl-;
- L3 represents —CO—, alkandiyl, -alkyl-CO— or —CO-alkyl-;
- R1 represents hydrogen, acyl, carbamoyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylcarbonyl, cycloalkylarbonyl or heterocyclylcarbonyl;
- R2 represents optionally substituted alkyl, aralkyl or heteroaralkyl;
- R3 represents hydrogen, or represents optionally substituted alkyl, aralkyl or heteroaralkyl;
- R4 represents optionally substituted alkandiyl, alkendiyl, alkyndiyl, cycloalkyldiyl, alkylcycloalkyldiyl, alkylcycloalkylalkyldiyl, aryldiyl, alkylaryldiyl, alkylarylalkyldiyl;
- R5 represents hydrogen, or represents optionally substituted alkyl, aralkyl or heteroaralkyl;
- R6 represents hydrogen, or represents optionally substituted alkyl, aralkyl or heteroaralkyl;
- provided that at least two of the substituents R2, R3, R5 and R6 are optionally substituted aralkyl or heteroaralkyl;
- n is 0, 1, 2, 3 or 4;
- and
- m is 0 or 1;
- Q is —NH2, —NH—C(NH)—NH2 or —NH—C(N-alkyl)-NH-alkyl;
- X is NH, O or S;
- Z1 is —CH2—;
- Z2 is a direct bond, alkandiyl, cycloalkyldiyl or aryldiyl;
- or a salt and solvate of such compound.
(canceled)
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A process for making compounds of the formula (I′)
- wherein
- R′1 represents hydrogen, acyl, carbamoyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylcarbonyl, cycloalkylarbonyl or heterocyclylcarbonyl;
- R′2 represents optionally substituted alkyl, aralkyl or heteroaralkyl;
- R′3 represents optionally substituted alkyl, aralkyl or heteroaralkyl;
- R′4 represents optionally substituted alkandiyl, alkendiyl, alkyndiyl, cycloalkyldiyl, alkylcycloalkyl, alkylcycloalkylalkyl or alkylaryl;
- n′ is 0, 1, 2, 3 or 4;
- and
- m′ is 0 or 1;
- by reacting compounds of the formula (II′)
- in which R′3, R′4, m and n have the meaning given above
- in the presence of an amide/peptide coupling reagent with compounds of the formula
- wherein R′1 and R′2 are defined as mentioned above,
- and deprotection with an acid.
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Dependencies are inferred from the claim text.