Organic compounds -- part of the class 532-570 series – Organic compounds – Cyclopentanohydrophenanthrene ring system containing
Reexamination Certificate
2011-03-08
2011-03-08
Badio, Barbara P (Department: 1628)
Organic compounds -- part of the class 532-570 series
Organic compounds
Cyclopentanohydrophenanthrene ring system containing
Reexamination Certificate
active
07902387
ABSTRACT:
Synthetic methods for preparing deoxycholic acid and intermediates thereof are provided.
REFERENCES:
patent: 2509248 (1950-05-01), Sarett
patent: 3065227 (1962-11-01), Dodson
patent: 3836516 (1974-09-01), Stempel et al.
patent: 4322553 (1982-03-01), Chupp
patent: 4917827 (1990-04-01), Batist et al.
patent: 6114336 (2000-09-01), Blanc-Ferras et al.
patent: 6313128 (2001-11-01), Blanc-Ferras et al.
patent: 6653492 (2003-11-01), Faarup
patent: 6936402 (2005-08-01), Kim et al.
patent: 2005/0042539 (2005-02-01), Kim et al.
patent: 2005/0261258 (2005-11-01), Kolodney et al.
patent: 2005/0267080 (2005-12-01), Kolodney et al.
patent: 2006/0127468 (2006-06-01), Kolodney et al.
patent: 2006/0154906 (2006-07-01), Kolodney et al.
patent: 2008/0318870 (2008-12-01), Moriarty et al.
patent: 2008/0319221 (2008-12-01), Junker et al.
patent: 2010/0145083 (2010-06-01), Prasad et al.
patent: 1214093 (1970-12-01), None
patent: WO 93/03732 (1993-03-01), None
patent: WO 94/27608 (1994-12-01), None
patent: WO 98/05337 (1998-02-01), None
patent: WO 02/088166 (2002-11-01), None
patent: WO 2005/112942 (2005-12-01), None
patent: WO 2005/117900 (2005-12-01), None
patent: WO 2006/133160 (2006-12-01), None
Chang, F.C. et al., “Seroflocculating Steroids. II. General,” J. Am. Chem. Soc. 1957, 79, 2161-2163.
Iida, T. et al., “A facile one-step synthesis of Δ1-4-3-keto bile acid esters by iodoxybenzene and benzeneselenic anhydride,” Journal of Lipid Research, 29(8), 1988, 1097-1101.
Kakushima, “Total synthesis of (±)-5β,8α-androst-9(11)-ene-3,17-dione,” Canadian Journal of Chemistry, 1979, vol. 57(24), pp. 3354-3356.
Lieberman, S. et al., “Studies in Steroid Metabolism II. Identification and Characterization of Ketosteroids Isolated from Urine of Healthy and Diseased Persons,” The Journal of Biological Chemistry 1948, 172, 263-295.
Mukawa, K. et al., “Studies on the Transformation of Unnatural Steroids by Micro-organisms. 14-βHydroxylation of Androstane Derivative,” Journal of the Chemical Society: Chemical Communications, 1971, vol. 18, pp. 1060-1061.
Potluri, V.K. et al., “Bile Acid-Derived Molecular Tweezers: Study of Solvent Effects in Binding, and Determination of Thermodynamic Parameters by an Extraction-Based Protocol,” J. Org. Chem., 2000, 65, 7764-7769.
Shoppee, C.W. J. Chem. Soc., 1946, 1134-1137.
“Deoxycholic Acid”. New Zealnd Pharamceuticals Ltd., (2007) http://www.nzp.co.nz/products.php?cid=2&pid=2.
Babcock, J.C. et al., “Reduction Methylation of Steroid Ketones”, Nov. 5, 1952, vol. 74, pp. 5472-5474.
Chambers, V.E.M. et al., “Microbiological Hydroxylation. Part XIV.1Hydroxylation in the Terminal Rings of Dioxygenated 5α-Androstanes with the FungiWojnowicia graminisandOphiobolus herpotrichus”, J.C.S. Perkin I, Jun. 27, 1974, 4/1285, pp. 55-58.
Constantin et al. “Introduction of the II-keto function in the steroids” J. Am. Chem. Soc., vol. 74, No. 15, 1952, pp. 3908-3910, XP002509787.
Danielsson et al. “On the Composition of the Bile Acid Fraction of Rabbit Feces and the Isolation of a New Bile Acid: 3α, 12α-Dihydroxy-5α-cholanic Acid”. The Journal of Biological Chemistry, (1963) 238 (12): 3846-3852.
Dodson et al. “Microbiological Transformations. VII. The Hydroxylation of Steroids at C-9”. Contribution from the Biological and Chemical Search Divisions of G. D. Searle and Co., Chicago 80, ILL., (1961) vol. 83: 4631-4635.
Fieser, L.F. et al., “Oxidation of Steroids. IV. Methyl Δ9(11)-Lithocholenate and Methyl 9α, 11α-Oxidolithocholanate1,2”, Jan. 1951, vol. 73, pp. 118-122.
Herzog et al. “11-Oxygenated steroids. II. The reduction of 11-carbonyl to 11-alpha-hydroxyl in the etiocholane series” J. Am. Chem. Soc., vol. 75, No. 2, 1953, pp. 269-272, XP002509785.
Heymann, H. et al., “A New Route to 11-Ketosteroids by Fission of a Δ9(11)-Ethylene Oxide1,2”, Nov. 1951, vol. 73, pp. 5252-5265.
Hofmann et al. “A proposed nomenclature for bile acids”. J. Lipid Res. (1992) 33: 599-604.
Hofmann. “Bile Acids: The good, the Bad, and the Ugly”. News Physiol. Sci. (1999) 14: 24-29.
Kametani et al. “First Total Synthesis of (+)-Chenodeoxycholic Acid”. J. Am. Chem. Soc.. (1981) 103:2890-2891.
Katona et al. “Synthesis, Characterization, and Receptor Interaction Profiles of Enantiomeric Bile Acids”. J. Med. Chem., (2007) 50, 6048-6058.
Katona, et al. “Enantiomeric Deoxycholic Acid: Total Synthesis, Characterization, and Preliminary Toxicity toward Colon Cancer Cell Lines”. J. Org. Chem., (2007) 72, 9298-9307.
Kolonin et al. “Reversal of obesity by targeted ablation of adipose tissue” Nature Medicine, Nature Publishing Group, New York, NY, US, vol. 10, No. 6, Jun. 1, 2004, pp. 625-632, XP00236820.
Lieberman et al. “Studies in steroid metabolism” J. Biol. Chem., vol. 196, No. 2, 1952, pp. 793-805, XP002509784.
Maneerat et al. “Bile acids are new products of a marine bacterium, Myroides sp. Strain SM1”. Appl. Microbiol. Biotechnol., (2005) 67: 679-683.
Marker et al. “Sterols. LXIX. Oxidation Products of Sarsasapogenin. Sarsasapogenoic Acid and Related Substances”. J. Am. Chem. Soc., (1939) 61(8): p. 2072-2077.
Matsuoka et al. “Micelle formation of sodium deoxycholate and sodium ursodeoxycholate (Part 1)”. Biochem. Biophys. Acta. 1580, (2002) pp. 189-199.
Mazur et al. “The Synthesis of the Steroidal Sepogenins”. J. Am. Chem. Soc., (1960) 82, 5889-5908.
Micheli, et al. “Total Syntheses of Optically Active 19-Norsteroids. (+)-Estr-4-ene-3,17-dione and (+)-13β-Ethylgon-4-ene-3,17-dione”. J. Org. Chem., (1975) vol. 40, No. 6, pp. 675-681.
Mukhopadhyay et al., “Chemistry and biology of bile acids”. Current Science, (2004) 87(12) 1666-1683.
Norton et al. “Crystal data (I) for some bile acid derivatives” Acta Cryst., vol. 19, 1965, pp. 477-478, XP002509788.
Reichstein et al. “Über Gallensäuren und verwandte Stoffee. 12. Mitteilung. Vereinfachte präparative Herstellung reiner Desoxy-cholsäure und eigener ihrer Derivate” Helvetica Chimica Acta, vol. 25, No. 5, Oct. 24, 2004, pp. 797-805, XP002509789.
Ridlon et al. “Bile salt biotransformations by human intestinal bacteria”. J. Lipid Res., (2006) 47(2): p. 241-259.
Roda et al. “Quantitative aspects of the interaction of bile acids with human serum albumin”. J. Lipid Res. (1982) 23(3): p. 490-495.
Rotunda et al. “Detergent effects of sodium deoxycholate are a major feature of an injectable phosphatidylcholine formulation used for localized fat dissolution”. Dermatol. Surgery, (2004) 30(7) :1001-1008.
Rotunda et al. “Lipomas treated with subcutaneous deoxycholate injections”. J. Am. Acad. Dermatol., (2005) pp. 973-978.
Rotunda et al. “Mesotherapy and Phosphatidylcholine Injections: Historical Clarification and Review” Dermatologic Surgery, (2006) 32: 465-480.
Sarett, L.H. et al., “Partial Synthesis of Etiocholene-9-OL-3(α)-ONE-17”, The Journal of Biological Chemistry, ASBMB, www.jbc.org, Dec. 5, 1947, pp. 185-187.
Seebeck et al. “Über Gallensäuren und verwandte Stoffe. 21. Mitteilung. 3-Alpha-acetoxy-12-keto-cholen-(9)-säure und 3-Alpha-oxy-cholen-(9)-säure” Helvetica Chimica Acta, vol. 26, No. 2, Oct. 24, 2004, pp. 536-562, XP002509786.
Shoppe, von C.W. et al., “98. Androsten-(9)-dion-(3,17), Bemerkungen zu H.Reich und A. Lardon1), Androsten-(9)-ol-(3β)-on-(17)”, Volumen 8, Fasciculus III (1947), pp. 766-768.
Svensson et al. “The Design and Bioactivation of Presystemically Stable Prodrugs”. Drug Metabolism Reviews, (1988) 19(2): 165-194.
Szczebara et al. “Total biosynthesis of hydrocortisone from a simple
Moriarty Robert M.
Prasad Achampeta Rathan
Reid John Gregory
Sahoo Akhila Kumar
Swaringen, Jr. Roy A.
Badio Barbara P
Foley & Lardner LLP
Kythera Biopharmaceuticals, Inc.
Tran Paul
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