Lipid-amino acid conjugates and methods of use

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Radical -xh acid – or anhydride – acid halide or salt thereof...

Reexamination Certificate

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C514S423000, C514S563000, C548S537000, C554S042000, C554S059000

Reexamination Certificate

active

07544714

ABSTRACT:
N-fatty acid-amino acid conjugates and J2prostanoid-amino acid conjugates are disclosed along with methods for making such conjugates and methods of using these conjugates in the treatment of conditions that involve dysfunctional lipid metabolism, insulin sensitivity, glucose homeostasis, and/or inflammation.

REFERENCES:
patent: 3711602 (1973-01-01), Herschler
patent: 4362716 (1982-12-01), Bouchaudon et al.
patent: 4649147 (1987-03-01), Mueller et al.
patent: 4847290 (1989-07-01), Burstein
patent: 4973603 (1990-11-01), Burstein
patent: 5112863 (1992-05-01), Hashimoto et al.
patent: 5164414 (1992-11-01), Vincent et al.
patent: 5338753 (1994-08-01), Burstein et al.
patent: 5538993 (1996-07-01), Mechoulam et al.
patent: 5635530 (1997-06-01), Mechoulam et al.
patent: 5998476 (1999-12-01), Sleigh et al.
patent: 6162829 (2000-12-01), Burstein
patent: 6262119 (2001-07-01), Ferrante et al.
patent: 2003/0022938 (2003-01-01), Burstein et al.
patent: WO 96/13507 (1996-05-01), None
patent: WO 03/007876 (2003-01-01), None
patent: WO 03/227876 (2003-01-01), None
patent: WO 03/035023 (2003-05-01), None
patent: WO 2006/010153 (2006-01-01), None
Sleigh et al., 1996, CAS: 125:115138.
Mueller et al., 1987, CAS: 87:16967.
Brnier et al., 2003, C2003-146818.
Hunag et al., The journal of Biological Chemistry, 2001, 276(46): 42639-42644.
Cascio et al., Biochemical and Biophysical Research Communications, January issue, 2004, 314:192-196.
Arioglu et al., “Efficacy and Safety of Troglitazone in the Treatment of Lipodystrophy Syndromes,”Ann. Intern. Med., 133(4):263-274 (2000).
Asada et al., “Antiinflammatory roles of peroxisome proliferator-activated receptor gamma in human alveolar macrophages,”Am. J. Respir. Crit. Care Med., 162(2):195-200 (2004).
Batrakov et al., “The polar-lipid composition of the sphingolipid-producing bacteriumFlectobacillus major,” Biochim. Biophys. Acta., 1484(2-3):225-240 (2000).
Burstein, “The cannabinoid acids: nonpsychoactive derivatives with therapeutic potential,”Pharmacol. Ther., 81(1):87-96 (1999).
Burstein et al., “Antagonism to the Actions of Platelet Activating Factor by a Nonpsychoactive Cannabinoid,”J. Pharmacol. Exp. Ther., 251(2):531-535 (1989).
Burstein et al., “Oxidative metabolism of anandamide,”Prostaglandins Other Lipid Mediat., 61:29-41 (2000).
Burstein et al., “Potential anti-inflammatory actions of the elmiric (lipoamino) acids,”Bioorganic&Medicinal Chem., 15:3345-3355 (2007).
Burstein et al., “Regulation of anandamide tissue levels by N-arachidonylglycine,”Biochem. Pharmacol., 64(7):1147-1150 (2002).
Cascio et al., “A structure-activity relationship study on N-arachidonoyl-amino acids as possible endogenous inhibitors of fatty acid amide hydrolase,”Biochem. Biophys. Res. Commun., 314(1):192-196 (2004).
Clark et al., “The Nuclear Receptor PPARγ and Immunoregulation: PPARγ Mediates Inhibition of Helper T Cell Responses,”J. Immunol., 164:1364-1371 (2000).
Cuzzocrea et al., “The cyclopentenone prostaglandin 15-deoxyΔ12,14-prostaglandin J2attenuates the development of acute and chronic inflammation,”Mol. Pharmacol., 61(5):997-1007 (2002).
Forman et al., “15-Deoxy-Δ12,14-Prostaglandin J2Is a Ligand for the Adipocyte Determination Factor PPARγ,”Cell, 83(5):803-812 (1995).
Gilroy et al., “Inducible cyclooxygenase-derived 15deoxy Δ12,14PGJ2brings about acute inflammatory resolution in rat pleurisy by inducing neutrophil and macrophage apoptosis,”FASEB J., 17(15):2269-2271 (2003).
Gilroy et al., “New insights into the role of COX 2 in inflammation,”J. Mol. Med., 78(3):121-129 (2000).
Hadigan et al., “Metabolic Effects of Rosiglitazone in HIV Lipodystrophy: A Randomized, Controlled Trial,”Ann. Intern. Med., 140(10):786-794 (2004).
Huang et al., “Identification of a New Class of Molecules, the Arachidonyl Amino Acids, and Characterization of One Member That Inhibits Pain,”J. Biol. Chem., 276(46):42639-42644 (2001).
Jiang et al., “PPAR-γ agonists inhibit production of monocyte inflammatory cytokines,”Nature, 391(6662):82-86 (1998).
Kawahito et al., “15-deoxy-Δ12,14-PGJ2induces synoviocyte apoptosis and suppresses adjuvant-induced arthritis in rats,”J. Clin. Invest., 106(2):189-197 (2000).
Kawai et al., “Lipoamino acids which are similar to bacterial endotoxin in both structure and biological activity related to physiological function,”Adv. Exp. Med. Biol., 256:159-162 (1990).
Kawazoe et al., “Phospholipids and a Novel Glycine-Containing Lipoamino Acid inCytophaga johnsonaeStanier Strain C21,”J. Bacteriol., 173(17):5470-5475 (1991).
Kliewer et al., “A Prostaglandin J2Metabolite Binds Peroxisome Proliferator-Activated Receptor γ and Promotes Adipocyte Differentiation,”Cell, 83(5):813-819 (1995).
Kliewer et al., “Differential expression and activation of a family of murine peroxisome proliferator-activated receptors,”Proc. Natl. Acad. Sci. USA, 91(15):7355-7359 (1994).
Kliewer et al., “Fatty acids and eicosanoids regulate gene expression through direct interactions with peroxisome proliferator-activated receptors α and γ,”Proc. Natl. Acad. Sci. USA, 94(9):4318-4323 (1997).
Kohno et al., “Identification of N-arachidonylglycine as the endogenous ligand for orphan G-protein-coupled receptor GPR18,”Biochem. Biophys. Res. Commun., 347(3):827-832 (2006).
Lehmann et al., “An Antidiabetic Thiazolidinedione Is a High Affinity Ligand for Peroxisome Proliferator-activated Receptor γ (PPARγ),”J. Biol. Chem., 270(22):12953-12956 (1995).
Lehmann et al., “Peroxisome Proliferator-activated Receptors α and γ Are Activated by Indomethacin and Other Non-steroidal Anti-inflammatory Drugs,”J. Biol. Chem., 272(6):3406-3410 (1997).
Lerouge et al., “Isolation and structural characterization of a new non-phosphorylated lipoamino acid fromMycobacterium phlei,” Chem. Phys. Lipids, 49(3):161-166 (1988).
Liu et al., “Activation and Binding of Peroxisome Proliferator-Activated Receptor γ by Synthetic Cannabinoid Ajulemic Acid,”Mol. Pharmacol., 63(5):983-992 (2003).
Milman et al., “N-arachidonoyl L-serine, an endocannabinoid-like brain constituent with vasodilatory properties,”Proc. Natl. Acad. Sci. U.S.A., 103(7):2428-2433 (2006).
Miyazaki et al., “Stimulation and inhibition of polymorphonuclear leukocytes phagocytosis by lipoamino acids isolated fromSerratia marcescens,” FEMS Immunol. Med. Microbiol., 6(4):265-271 (1993).
Mukherjee et al., “Identification, Characterization, and Tissue Distribution of Human Peroxisome Proliferator-activated Receptor (PPAR) Isoforms PPARγ2versusPPARγ1 and Activation with Retinoid X Receptor Agonists and Antagonists,”J. Biol. Chem., 272(12):8071-8076 (1997).
Nagy et al., “Oxidized LDL Regulates Macrophage Gene Expression through Ligand Activation of PPARγ,”Cell, 93(2):229-240 (1998).
Patel et al., “Tumor suppressor and anti-inflammatory actions of PPARγ agonists are mediated via upregulation of PTEN,”Curr. Biol., 11(10):764-768 (2001).
Perkins, “The Rel/NF-κB family: friend and foe,”Trends Biochem. Sci., 25:434-440 (2000).
Pertwee, “Cannabinoid receptors and pain,”Prog. Neurobiol., 63(5):569-611 (2001).
Pertwee, “The ring test: a quantitative method for assessing the ‘cataleptic’ effect of cannabis in mice”Br. J. Pharmacol., 46(4):753-763 (1972).
Pestonjamasp et al., “Anandamide synthesis is induced by arachidonate mobilizing agonists in cells of the immune system,”Biochim. Biophys. Acta, 1394:249-260 (1998).
Prusakiewicz et al., “Selective oxygenation ofN-arachidonylglycine by cyclooxygenase-2,”Biochem

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