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US 12,709,596 B2Granted
Molecules
AssigneeEna Respiratory Pty Ltd
InventorsIan Holmes, Weiguang Zeng, David Jackson, Christophe Demaison, Grant Mclachlan
Life of this patent
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Abstract
The present invention relates to TLR2 agonist compounds and their compositions, and the use of such compounds and compositions in the prevention and/or treatment of respiratory infections, or diseases or conditions associated with viral or bacterial infections.
Claims20
A compound of general formula:
- A-Y—B
- wherein A is represented by:
- wherein:
- b is 0;
- w is 1;
- v is an integer from 2 to 5;
- z is 1;
- X is —S—;
- Z1 and Z2 are each independently selected from the group consisting of —O—, —NR—, —S—, S(═O), S(═O)2—, —C(═O)O—, —OC(═O)—, —C(═O)NR—, —NRC(═O)—, —C(═O)S—, —SC(═O)—, OC(═O)O—, NRC(═O)O—, —OC(═O)NR—, and —NRC(═O)NR—;
- R11, R12, Rx, Ry, R14, R15, R16, and R17 are each independently H or C1-C6 aliphatic;
- R, R13 and R18 are each independently H or C1-C6 aliphatic;
- R19 is H, C1-C6 aliphatic, an amino protecting group, L3-C(═O)—, or A2;
- L1 and L2 are each independently C5-C21 aliphatic or C4-C20 heteroaliphatic;
- L3 is C1-C21 aliphatic or C2-C20 heteroaliphatic;
- A2 is an amino acid or a peptide;
- wherein any aliphatic or heteroaliphatic present in any of R, R11, R12, R13, R14, R15, R16, R17, R18, R19, Rx, Ry, L1, L2, and L3 is optionally substituted;
- Y is
- wherein:
- R1 and R2 are independently selected from the group consisting of H, —CH2OH, —CH2CH2OH, —CH(CH3)OH, —CH2OPO(OH)2, —CH2C(═O)NH2, —CH2CH2C(═O)OH and —CH2CH2C(═O)OR8, wherein any one of the alkyl hydrogens can be replaced with a halogen;
- R8 is selected from the group consisting of H and a straight or branched C1-C6 alkyl;
- and
- B represents a Polyethylene Glycol (PEG), wherein the PEG is a substituted PEG according to the following formula:
- wherein
- n is 3 to 100;
- m is 1, 2, 3, or 4;
- p is 2, 3, or 4;
- q is null or 1;
- R3 is H, —NH2, or —OH, wherein when q is null, R3 is H and when q is 1, R3 is —NH2 or —OH;
- L is null or consists of 1 to 10 units, wherein each unit has the formula:
- wherein
- R4 is H;
- and
- R5 is a side chain of an amino acid selected from:
- the 20 naturally occurring amino acids commonly designated by three letter symbols, 4-hydroxyproline, hydroxylysine, demosine, isodemosine, 3-methylhistidine, norvlin, beta-alanine, gamma-aminobutyric acid, citrulline, homocysteine, homoserine, ornithine, and methionine sulfone;
- or a pharmaceutically acceptable salt, solvate or prodrug thereof.
32 more elements
Dependencies are inferred from the claim text.