Conjugates of polyunsaturated fatty acids and amine-containing compounds and uses thereof
OwnerTaher Nassarinventor
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Abstract
Novel chemical conjugates derived from unsaturated fatty acids and therapeutically active agents, are disclosed. The chemical conjugates are designed and characterized as COX-2 and/or 5-LOX inhibitors and are useful in the treatment of inflammatory diseases and disorders such as Alzheimer's disease, Parkinson's disease, asthma, osteoarthritis, rheumatoid arthritis, pain, primary dysmenorrhea, Crohn's disease and ulcerative colitis.
Claims22
1-40. (canceled)
A method for treating dermatitis in a subject in need comprising the step of administering the subject in need docosa-4,7,10,13,16,19-hexaenoic acid linked to a hydroxyproline, thereby treating dermatitis in the subject.
A method of synthesizing 1-docosa-4,7,10,13,16,19-hexaenoyl-4-hydroxy-pyrrolidine-2-carboxylic acid comprising:
- mixing tetrahydrofurane with decosahexanoic acid;
- adding triethylcloroformate;
- adding triethylamine;
- stirring and filtering;
- adding a solution of hydroxyproline and NaOH in water;
- adding strong acid;
- adding hexane;
- collecting organic layer;
- and drying
A chemical conjugate comprising a first moiety and a second moiety covalently linked therebetween, wherein said second moiety is derived from docosa-4,7,10,13,16,19-hexaenoic acid, and wherein said first moiety is derived from a therapeutically active agent or a derivative thereof, each independently having a functional group for forming a covalent bond with said second moiety, with the proviso that said first moiety is not hydroxyproline, the chemical conjugate being a cyclooxygenase-2 (COX-2) inhibitor.
A chemical conjugate comprising a first moiety and a second moiety covalently linked therebetween, wherein said second moiety is derived from y-linolenic acid, and wherein said first moiety is derived from a therapeutically active agent or a derivative thereof, each independently having a functional group for forming a covalent bond with said second moiety, with the proviso that said first moiety is not hydroxyproline or taurine, the chemical conjugate being a cyclooxygenase-2 (COX-2) inhibitor.
A chemical conjugate comprising a first moiety and a second moiety covalently linked therebetween, wherein said first moiety is derived from a compound selected from the group consisting of 5-hydroxy-indol-3-yl-acetic acid, 2-amino-nicotinic acid, salicyclic acid, mesalazine, quercetin and resveratrol, and wherein said second moiety is derived from a fatty acid.
A chemical conjugate selected from the group consisting of:
- N-(docosa-4,7,10,13,16,19-hexaenoyl)-5-hydroxy-indol-3-yl-aceticacid (MWL004);
- N-(docosa-4,7,10,13,16,19-hexaenoyl)-2-amino-nicotinic acid (MWL005);
- N-(docosa-4,7,10,13,16,19-hexaenoyl)-2-amino-phenyl-acetic acid (MWL006);
- N-oleoyl-5-hydroxy-indol-3-yl-acetic acid (MWL007);
- N-oleoyl-2-amino-nicotinic acid (MWL008);
- O-oleoyl-salicylic acid (MWL009);
- O-(docosa-4,7,10,13,16,19-hexaenoyl)-salicylic acid (MWL013);
- O-(y-linolenoyl)-salicylic acid (MWL014);
- N-(y-linolenoyl)-5-amino-salicylic acid (MWL015);
- N-(docosa-4,7,10,13,16,19-hexaenoyl)-5-amino-salicylic acid (MWL016);
- N-oleoyl-5-amino-salicylic acid (MWL017);
- and
- N-docosa-4,7,10,13,16,19-hexaenoyl-taurine (MWL002).
Dependencies are inferred from the claim text.