Peptoid oligomers, pharmaceutical compositions and methods of using the same
AssigneeNew York University
InventorsKent Kirshenbaum, Sung Bin Shin
Life of this patent
Estimating the term…
Abstract
Novel peptoid oligomers are disclosed that have a formula represented by the following formula I: The peptoids demonstrate antimicrobial activity and may be prepared as pharmaceutical compositions and used for the prevention or treatment of a variety of conditions in mammals including humans where microbial invasion is involved. The present cyclic and linear peptoids are particularly valuable as their effect is rapid, broad in spectrum and mostly indifferent to resistance provoked by standard antibiotics.
Claims24
A peptoid oligomer according to formula (Ia) or (Ib):
- wherein the peptoid oligomer consists of a repeating unit of a monomer
- wherein
- each R1 is independently R1a, R1b, or R1c;
- each R2 is independently hydrogen, or unsubstituted alkyl;
- or each R1 and R2 are joined together to form a 4-7 membered heterocyclic ring;
- each R1a is independently Et, n-Pr, i-Pr, n-Bu, sec-Bu, i-Bu, or alkyl substituted with halo, hydroxy, nitro, or alkoxy;
- each R1c is independently substituted or unsubstituted aryl, substituted or unsubstituted phenylalkyl, substituted or unsubstituted naphth-2-ylalkyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, or substituted or unsubstituted diarylalkyl;
- X is H, C(O)R20, or C(O)R21;
- and each R1b is independently 5-aminopentyl, 6-aminohexyl, guanidinoalkyl (H2N—C(═NH)—NH-alkyl), imidazolylmethyl, 2-imidazolylethyl, 4-imidazolylbutyl, 5-imidazolylpentyl, 6-imidazolylhexyl, or alkyl substituted with pyrrolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, or tetrazolyl, and wherein each R1b is unsubstituted or substituted with one or more F;
- or
- X is C(O)R20, or C(O)R21;
- and each R1b is independently 3-aminopropyl, or 4-aminobutyl;
- R20 is unsubstituted C1-C30 alkyl, C3-C10 cycloalkyl, C3-C10 cycloalkylmethyl, 4-10 membered heterocycloalkyl, aryl, arylalkyl, 5-10 membered heteroaryl or heteroarylalkyl;
- R21 is C1-C8 alkyl, C3-C10 cycloalkyl, 4-10 membered heterocycloalkyl, C6-C10 aryl, arylalkyl, 5-10 membered heteroaryl or heteroarylalkyl, wherein the alkyl is substituted with halo or hydroxyl, and wherein the cycloalkyl, the heterocycloalkyl, the aryl, the arylalkyl, the heteroaryl, the heteroarylalkyl are substituted with unsubstituted C1-C4 alkyl, halo, unsubstituted C1-C4 alkoxy, unsubstituted C1-C4 haloalkyl, unsubstituted C1-C4 hydroxyalkyl, unsubstituted C1-C4 haloalkoxy, or hydroxyl;
- Y is NH2, OH, acylamino, or acyloxy;
- n is an integer between 2 and 20, when the peptoid oligomer is of formula (Ia);
- and n is an integer between 4 and 20, when the peptoid oligomer is of formula (Ib);
- provided that:
- i) at least one instance of R1 is R1b;
- ii) when the peptoid oligomer is of formula (Ia) and R1b is 2-imidazol-4-ylethyl, then X is other than H;
- and iii) when the peptoid oligomer is of formula (Ia), then the oligomer further consists of the terminal groups X and Y;
- a pharmaceutically acceptable salt, a solvate, a prodrug, stereoisomers, isotopic variants, or tautomers thereof.
A peptoid oligomer selected from the group consisting of
- a salt, stereoisomers, isotopic variants, or tautomers thereof.
Dependencies are inferred from the claim text.