Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2004-07-20
2009-11-10
Aulakh, Charanjit S (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C546S318000
Reexamination Certificate
active
07615641
ABSTRACT:
This application pertains to compounds comprising unbranched long chain aliphatic alcohols linked to a heterocyclic carboxylic acid moiety by means of an ester or ether linkage. The aliphatic alcohols may include aliphatic alcohols present in polycosanol, such as octacosanol. The heterocyclic carboxylic acid moieties include a 5-membered ring, a 6-membered ring, or a bicyclic ring. In one embodiment, the compounds of the invention include 1-octacosanyl nicotinate and salts thereof. The invention includes prodrugs, pharmaceutically acceptable salts, and pharmaceutical compositions of the compounds, and methods of making and using the compounds.
REFERENCES:
patent: 5856316 (1999-01-01), Laguna Granja et al.
patent: 6015821 (2000-01-01), Horrobin et al.
patent: 6197832 (2001-03-01), Sorkin, Jr.
patent: 6328998 (2001-12-01), Cavazza
patent: 6403619 (2002-06-01), Jacobson et al.
patent: 6500451 (2002-12-01), Adams
patent: 2002/0016314 (2002-02-01), Schersl
patent: 2002/0192353 (2002-12-01), Cain et al.
patent: 00519993 (1995-06-01), None
patent: 01121928 (2001-08-01), None
patent: 01249180 (2002-10-01), None
patent: 1 161 884 (2003-03-01), None
patent: 58017179 (1983-02-01), None
patent: 61060893 (1986-03-01), None
patent: 05044070 (1993-02-01), None
patent: 2002 345414 (2002-12-01), None
patent: WO 91/13931 (1991-03-01), None
patent: 982744 (1998-04-01), None
Palacin, S. et al.: Molecular Engineering: Highly ordered langmuir-biodgett films based on a cobalt phthalocyanine and its axial complexation. J. Phys. Chem., vol. 93, pp. 7195-7199, 1989.
Oesch, U. et al.: Design of neutral hydrogen ion carriers for solvent polymeric membrane electrodes of selected pH range. Anal. Chem. vol. 58, pp. 2285-2289, 1986.
Bertelsen et al., Structural Elucidation of Alkyl-Branched Chain Aliphatic Alcohols, Fette Seigen Anstrichmittel No. 9, pp. 336-342 (1985) Sweden.
Gamez et al., Dose-Dependent Cholesterol-Lowering Effects of D-003 on Normocholesterolemic Rabbits, Current Therapeutic Research, pp. 460-468, vol. 61, No. 7, (2000) Cuba.
Molina et al., Antiplatelet and Antithrombotic Effect of D-003, pp. 137-143, Pharmaceutical Research, vol. 42, No. 2, (2000) Cuba.
Taylor et al., Octacosanol in Human Health, Nutrition 19:192-195, (2003) USA.
Mdluli et al., Inhibition of aMycobacterium tuberculosisbeta-ketoacyl ACP synthase by isoniazid, Science (Wash.) vol. 280, No. 5369, pp. 1607-1610, USA (Abstract).
Koukilia-Kaehkoelae et al.,Mycobacterium branderisp. nov., a new potential human pathogen, Int. J. Syst. Bacteriol., vol. 45, No. 3, pp. 549-553, (1995),Finland (Abstract).
Davidson et al., Efficacy of over-the-counter nutritional supplements, Curr Atheroscler Rep pp. 15-21 (2003) USA (Abstract).
De Jong, Tobacco Leaf Protein: I. An evaluation of the use of putative chemical growth, Beitrage zur Tabakforschung Int., vol. 15, No. 1, pp. 33-42 (1991), USA (Abstract).
Re et al., Effects of some natural extracts on the acetylcholine release at the mouse neuromuscular junction, Pharmacol Res, vol. 39, pp. 239-245 (1999), Italy (Abstract).
Vasanth et al., Phytochemical study ofLeonotis nepetaefoliaRBr., Indian Drugs 26(3) pp. 127-128 (1988), India (Abstract).
Sugihara et al., Studies on intestinal lymphatic absorption of drugs, II. Glyceride prodrugs for, Journal of Pharmacobio-Dynamics 11(8), pp. 555-562 (1988) Japan (Abstract).
Harvey, D.J., Pyridine-containing derivatives for the structural elucidation of the alkyl chains, Spectroscopy 8(1-6) pp. 211-244 (1990) Netherlands (Abstract).
Iup et al., Results of the multicenter controlled study of the hypolipidemic drug polycosanol in Russia, Ter Arkh. 2000;72(12): pp. 7-10 (Abstract).
Kabir et al., Biodistribution and metabolism of orally administered octacosanol in rats, Ann Nutr Metab. 1993;37(1): pp. 33-38 (Abstract).
Liu et al., Active constituents lowering blood-lipid in beeswax, Zhongguo Zhong Yao Za Zhi. Sep. 1996;21(9): pp. 553-554 (Abstract).
Varady et al., Role of policosanols in the prevention and treatment of cardiovascular disease, Nutr Rev. Nov. 2003;61(11): pp. 376-383 (Abstract).
Pieper, J.A., Overview of niacin formulations: differences in pharmacokinetics, efficacy, Am J. Health Syst Pharm. Jul. 1, 2003;60(13 Suppl 2): S9-14; quiz S25 (Abstract).
Malik et al., Niacins, lipids, and heart disease, Curr Cardio Rep. Nov. 2003;5(6) 470-6 (Abstract).
NHLB1-CHD Cholesterol Lowering Medicines—Nicotinic Acid—pp. 1-2; http://www.nhlbi.nih.gov/chd/meds3.htm , May 12, 2004.
Policosanol, The Hoffman Center, (New York) http://www.drhoffman.com/policosanol , Feb. 1, 2004.
Medications for Lowering Your Cholesterol, http://www.lifeclinic.com/focus/cholesterol/Nicotinic—acid.asp , Feb. 1, 2004.
Cabrera, L. et al., Stability Studies of Tablets Containing 5 and 10 MG of Policosanol as Active Principle, Centro Nacional de Investigaciones Clientificas, Cuba (Abstract) , 2002.
Uribarri, E. et al., Physico-Mechanical Charcterization of DO03, A Novel Hypocholesterolemic Drug, Laboratorios MedSol, Cuba (Abstract) , 2002.
Hargrove et al., Policosanol: Waxes make cholesterol wane, FASEB Journal, vol. 17, No. 4-5, Mar. 2003, (Abstract).
Shepherd, T. et al., Effects of environment on the composition of epicuticular wax from kale and swede, Phytochemistry, vol. 40(2) pp. 407-414 (1995), U.K. (Abstract).
Molina, V. et al., Synergistic effect of D-003 and aspirin on experimental thrombosis, Prostaglandins Leukotrienes and, vol. 68(5), pp. 305-310, (2003), Cuba (Abstract).
Noa, M. et al., Effect of D-003, a mixture of high molecular, on CL4C-induced liver acute injury in rats, Drugs under Exp, vol. 28(5) pp. 177-183 (2002), Cuba (Abstract).
Mas, Rosa et al., Dose-dependent cholesterol-lowering effects of D-003, Current Therapeutic Research, vol. 61(7), pp. 460-468 (2000), Cuba (Abstract).
Molina, V. et al., D-003, a potential antithrombotic compound isolated from sugar cane wax, Prostaglandinds, Leukotrienes, vol. 67(1), pp. 19-24, (2002), UK (Abstract).
Gever, J.R. et al., Rice field surface microlayers: collection, composition and pesticide enrichment, Environmental Toxicol, vol. 15(10) pp. 1676-1682, (1996), USA (Abstract).
Lal, B. et al., Mineralization of Y super(14)C octacosane by Acinetobacter calcoacet S30, Can. J. Microbiol./rev. Can.., vol. 42(12), pp. 1225-1231, (1996), CA (Abstract).
Demchenko, A.V. et al., Synthesis and biological evaluation of Rhizobium sin-1 lipid A derivatives, J. Am. Chem. Soc., vol. 125(20), pp. 6103-6112, (2003), USA (Abstract).
Rodriguez, M.D. et al., Lack of developmental toxicity of D-003: a mixture of long-chain fatty acids in rats, Food Chem Toxicol, vol. 41, pp. 89-93, (2003), U.K. (Abstract).
Menendez, R. et al., Inhibition of rat lipoprotein lipid peroxidation by the oral administration of D003, Can J. Physiol. Pharmacol, vol. 80, pp. 13-21, (2002), CA (Abstract).
Menendez, R. et al., Inhibition of cholesterol biosynthesis in cultured fibroblasts by D003, Pharmacol Res., vol. 44, pp. 299-304, (2001), U.K. (Abstract).
Gamez, R. et al., Preliminary evaluation of the cytotoxic and genotoxic potential of D-003, Teratog Carcinog Mutagen, vol. 22, pp. 175-181, (2002), USA (Abstract).
Molina, V. et al., Antiplatelet and antithrombotic effect of D-003, Pharmacol Res., vol. 42, pp. 137-143, (2000) U.K. (Abstract).
McNevin, J.P. et al., Isolation and characterization of eceriferum (cer) mutants induced by T-DNA, Genome, vol. 36, No. 3, pp. 610-618, CA (Abstract) , 1993.
Kato, S. Karino et al., Octacosanol affects lipid metabolism in rats fed on high-fat diet, British Journal of Nutrition, 73, 433-441, (1995) UK.
Taconic Animal Models, Apoe (ApoE) Targeted Mutation Mice, http://www. taconic.com/anmodels/apos.htm , May 1998.
Shimura, S. et al., Studies on the effect of octacosanol on motor endurance in mice, Nutrition Reports International, 36(5), pp. 1029-1038 (1987) (Abstract).
Gouni-Berthold, I. et al., Policosanol: Clinical pharmacology and therapeutic significance of a new lipid-lowering agent, American Heart Journal 143(2), pp. 356-365 (1987).
Hernandez, F. et al., Effect of policosanol on serum lipids and lipoprot
Aulakh Charanjit S
Oyen Wiggs Green & Mutala LLP
Sino Pharmaceuticals Corporation
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