Dendrimeric peptides, pharmaceutical compositions and methods of using the same
AssigneeNew York University
InventorsNeville Robert Kallenbach, Filbert Totsingan
Life of this patent
Estimating the term…
Abstract
Novel peptide compounds and pharmaceutical compositions thereof are disclosed that have a formula represented by the following formula (I) wherein L1, L2, L3, Z, R1, R2, R4 and R5 are as described herein. The compounds demonstrate antimicrobial activity and may be prepared as pharmaceutical compositions and used for the prevention and treatment of a variety of conditions in mammals including humans where microbial invasion is involved. The present peptides are particularly valuable as their effect is rapid, broad in spectrum and mostly indifferent to resistance provided by standard antibiotics.
Claims95
A pharmaceutical composition for preventing, treating, ameliorating or managing a disease or condition caused by micro organisms;
- wherein the pharmaceutical composition comprises a peptide according to formula I or Ia:
- wherein
- each L1 and L3 is independently substituted or unsubstituted C2-5 alkylene;
- L2 is substituted or unsubstituted C3-5 alkylene;
- each R1 is independently —NH-(A)m-Z, or
- each A is independently an peptide residue selected from R, W, W*, F, Y, K, 2-Nal, Tta, and H*;
- m is 1, 2, 3, or 4;
- each Z is independently H, Ac, or any other conventional N-protecting group;
- R3 is substituted or unsubstituted alkyl, aralkyl, heteroarylalkyl, aminoalkyl, or guanidinoalkyl;
- R2 is R1;
- or R2 is —N(L1-R1)2;
- R4 is R5, or
- and each R5, R6, and R7 is independently —NH—(B′)n—Z, or
- each B′ is independently an peptide residue selected from R, W, W*, F, Y, K, 2-Nal, H*, and Tta;
- n is 2, 3, or 4;
- each Z is independently H, Ac, or any other conventional N-protecting group;
- and
- Tta is 2,5,7-trialkyltryptophan residue;
- or a pharmaceutically acceptable salt, solvate or prodrug thereof;
- and stereoisomers, isotopic variants and tautomers thereof;
- provided that when the peptide is according to formula Ia;
- then at least one of B's is Tta.
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A pharmaceutical composition for preventing, treating, ameliorating or managing a disease or condition caused by micro organisms;
- wherein the pharmaceutical composition comprises a peptide according to formula Ia:
- wherein
- each L3 is independently substituted or unsubstituted C2-5 alkylene;
- R3 is substituted or unsubstituted alkyl, aralkyl, heteroarylalkyl, aminoalkyl, or guanidinoalkyl;
- R4 is R5, or
- and each R5, R6, and R7 is independently —NH—(B′)n—Z, or
- each B′ is independently an peptide residue selected from R, W, W*, F, Y, K, 2-Nal, H*, and Tta;
- n is 2, 3, or 4;
- each Z is independently H, Ac, or any other conventional N-protecting group;
- and
- Tta is 2,5,7-trialkyltryptophan residue;
- or a pharmaceutically acceptable salt, solvate or prodrug thereof;
- and stereoisomers, isotopic variants and tautomers thereof;
- provided that at least one of B's is Tta.
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A peptide according to formula Ia:
- wherein
- each L3 is independently substituted or unsubstituted C2-5 alkylene;
- R3 is substituted or unsubstituted alkyl, aralkyl, heteroarylalkyl, aminoalkyl, or guanidinoalkyl;
- R4 is R5, or
- and each R5, R6, and R7 is independently —NH—(B′)n—Z, or
- each B′ is independently an peptide residue selected from R, W, W*, F, Y, K, 2-Nal, H*, and Tta;
- n is 2, 3, or 4;
- each Z is independently H, Ac, or any other conventional N-protecting group;
- and
- Tta is 2,5,7-trialkyltryptophan residue;
- or a pharmaceutically acceptable salt, solvate or prodrug thereof;
- and stereoisomers, isotopic variants and tautomers thereof;
- provided that at least one of B's is Tta.
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Dependencies are inferred from the claim text.