Synthetic lactone formulations and methods of use

Details Synthetic lactone formulations and methods of use Synthetic lactone formulations and methods of use

2011-06-07

2011-06-07

Wilson, James O (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C549S295000

Reexamination Certificate

active

07956088

ABSTRACT:
Natural and synthetic compounds having a lactone structure methods for using and making the compounds have been disclosed. The compounds are useful as anti-bacterial, anti-fungal and anti-inflammatory agents, and for treating proliferation disorders such as melanoma, leukemia, breast cancer, lung cancer, ovarian cancer, colon cancer, esophagus cancer, liver cancer, and lymphatic cancer. The compounds are also effective for treatment or prevention of inflammatory diseases such as atherosclerosis, lung fibrosis, systemic lupus erythematosus, pancreatitis, sarcoidosis, glomerulitis, and organ transplant rejection. They are also effective for treatment or prevention of bacterial and fungal infections, including treatment of peptic ulcers, gastritis, dyspepsia and gastric cancer, gingivitis and periodontitis.

REFERENCES:
patent: 2624723 (1953-01-01), McGraw
patent: 3203953 (1965-08-01), Lucas et al.
patent: 3210377 (1965-10-01), Machleidt et al.
patent: 3993771 (1976-11-01), Uematsu et al.
patent: 4001425 (1977-01-01), Price, Jr.
patent: 4613613 (1986-09-01), Oguri et al.
patent: 5242945 (1993-09-01), Caufield et al.
patent: 5250735 (1993-10-01), Wong et al.
patent: 5281622 (1994-01-01), Wong et al.
patent: 5595756 (1997-01-01), Bally et al.
patent: 5646164 (1997-07-01), Tzeng et al.
patent: 5905089 (1999-05-01), Hwang et al.
patent: 5962460 (1999-10-01), Tzeng et al.
patent: 5977169 (1999-11-01), Chrusciel et al.
patent: 6180651 (2001-01-01), Nicolai et al.
patent: 6222048 (2001-04-01), Black et al.
patent: 6232474 (2001-05-01), Brandenburg et al.
patent: 6395724 (2002-05-01), Judice et al.
patent: 6686390 (2004-02-01), Pal et al.
patent: 6900242 (2005-05-01), Terrero
patent: 7323495 (2008-01-01), Terrero
patent: 2005/0101663 (2005-05-01), Terrero et al.
patent: 2005/0209316 (2005-09-01), Terrero
patent: 2005/0239877 (2005-10-01), Gomez et al.
patent: 0 534 907 (1993-03-01), None
patent: 0 712 843 (1996-05-01), None
patent: 51-125722 (1976-11-01), None
patent: 54-084564 (1979-07-01), None
patent: 56-128776 (1981-10-01), None
patent: 58-099413 (1983-06-01), None
patent: 62-026221 (1987-02-01), None
patent: 64-016776 (1989-01-01), None
patent: 01-163175 (1989-06-01), None
patent: 2002-37797 (2006-02-01), None
patent: 2002037797 (2006-02-01), None
patent: 96/29392 (1996-09-01), None
patent: WO 98/40078 (1997-03-01), None
patent: WO 97/28147 (1997-08-01), None
patent: WO 98/43966 (1998-10-01), None
patent: 99/53915 (1999-10-01), None
patent: WO 01/39720 (2001-06-01), None
patent: WO 01/39720 (2001-07-01), None
patent: WO 01/64913 (2001-09-01), None
patent: WO 02/064160 (2002-08-01), None
patent: WO 02/100854 (2002-12-01), None
patent: WO 2005/102315 (2005-11-01), None
Laurence Chan, Transplant Rejection and its Treatment, Chapter 9. Tracy 12, Dec. 12, 2008.
Baldwin, et al. “5-endo-trigonal Reactions: a Disfavoured Ring Closure”Chem. Commun. 1976:736-739 (1976).
Cassady, et al. “Potential Antitumor Agents. Synthesis, Reactivity and Cytotoxicity of ÿ-methylene carbonyl compounds,”J. Med. Chem. 21(8):815-819 (1978).
Cavallito, et al. “ÿ-Methylene Butyrolactone fromEythronium americanum,” JACS68:2332-4.
Chen, et al., “gamma-Methylene-valero-butyrolactones: synthesis and vasorelaxing activity assay of coumarin, naphthalene, and quinolone derivatives,”Chem. Pharm. Bull. 46(6): 962-965 (1998).
Fuchino, et al., “New sesquiterpene lactones fromElephantopus mollisand their leishmanicidal activities,”Planta Med67: 647-653 (2001).
Grigg, et al., “X=Y-ZH Systems as potential 1,3-dipoles part 35. Generation of nitrones from oximes. Class 3 processes. Tandem intramolecular Michael addition (1,3-azaprotio cyclotransfer)-intermolecular 1,3-dipolar cycloaddition reactions.1.2”Tetrahedron. 48(33): 6929-6952 (1992).
Hoffman, et al. “Synthese and biologische Aktivität von -Methylen-butyrolactonen,” Angewandte Chemie 97(2):96-112 (1985).
Howie, et al “Synthesis of alkyl-substituted .alpha.,.beta.-unsaturated .gamma.-lactones as potential antitumor agents,”J. Med. Chem17(8):840-3 (1974).
Huang, et al., “Synthetic and cytotoxic studies ofimg id="CUSTOM-CHARACTER-00001" he="3.13mm" wi="1.78mm" file="US07956088-20110607-P00001.TIF" alt="custom character" img-content="character" img-format="tif" ?-methylene-img id="CUSTOM-CHARACTER-00002" he="3.13mm" wi="1.78mm" file="US07956088-20110607-P00001.TIF" alt="custom character" img-content="character" img-format="tif" ?-butyrolactone bearing pyrimidines,”Kaohsiung J. Med. Sci. 9: 707-711 (1993).
Hutchinson, “A synthesis of tulipalin A and B and the acylglucoside, tuliposide A, fungitoxic agents fromTulipa gesneriana. Carbon-13 nuclear magnetic resonance analysis of anomeric configuration in acylglucosides”,J. Org. Chem., 39(13):1854-8 (1974).
Ingolfsdottir, et al “In vitro susceptibility ofHelicobacter pylorito protolichesterinic acid from the lichenCetraria islandica,” Antimicrob. Agents and Chemo. 41(1) 1997.
Kuhajda, et al., “Synthesis and antitumor activity of an inhibitor of fatty acid synthase,”Proc. Natl. Acad. Sci. USA97(7): 3450-3454 (2000).
Lee, et al., “Sesquiterpene antitumor agents: inhibitors of cellular metabolism,”Science196: 533-535 (1977).
Lee, et al., “Synthesis and anticancer evaluation of certainimg id="CUSTOM-CHARACTER-00003" he="3.13mm" wi="1.78mm" file="US07956088-20110607-P00001.TIF" alt="custom character" img-content="character" img-format="tif" ?-methylene-img id="CUSTOM-CHARACTER-00004" he="3.13mm" wi="1.78mm" file="US07956088-20110607-P00001.TIF" alt="custom character" img-content="character" img-format="tif" ?-(4-substituted phenyl)-g-butyrolactone bearing thymine, uracil, and 5-bromouracil,”Bioorg.&Med. Chem. 9: 241-244 (1999).
Lenz, et al. “A test battery of bacterial toxicity assays and comparison with LD50 values,”Toxicity Assessment4(1)43-52 (1989).
Maria, et al., “Gastric anti-ulcer activity of severalimg id="CUSTOM-CHARACTER-00005" he="3.13mm" wi="3.56mm" file="US07956088-20110607-P00002.TIF" alt="custom character" img-content="character" img-format="tif" ?-unsaturated carbonyl compounds in rats,”Biol. Pharm. Bull. 23(5): 555-557 (2000).
Murray and Norton, “The design and mechanism of palladium catalysts for synthesis of methylene lactones by cyclocarbonylation of acetylenic alcohols”,J. Amer. Chem. Soc., 101:4107-19 (1979).
Panda, et al., “Mechanism of action of alpha-methylene-gamma-lactone derivatives of substituted nucleic acid bases in tumour cells,”Chemotherapy35: 174-180 (1989).
Park, et al. “Anti-Heliobacter pyloriEffect of Costunolide Isolated from the Stem Bark ofMagnolia sieboldii” Archives of Pharmacal Research, 20(3): 275-279 (1997).
Prestera,et al. “Chemical and molecular regulation of enzymes that detoxify carcinogens,”Proc. Natl. Acad. Sci. U S A. 90(7):2965-9(1993).
Rodriguez, et al., “Biological activities of sesquiterpene lactones,”Phytochemistry15: 1573-1580 (1976).
Sanyal, et al., “Newimg id="CUSTOM-CHARACTER-00006" he="3.13mm" wi="1.78mm" file="US07956088-20110607-P00001.TIF" alt="custom character" img-content="character" img-format="tif" ?-methylene-img id="CUSTOM-CHARACTER-00007" he="3.13mm" wi="1.78mm" file="US07956088-20110607-P00001.TIF" alt="custom character" img-content="character" img-format="tif" ?-lactone derivatives of substituted nucleic acid bases as potential anticancer agents,”J. Med. Chem. 29(5): 595-599 (1986).
Schlewer, et al., “Synthesis ofimg id="CUSTOM-CHARACTER-00008" he="3.13mm" wi="1.78mm" file="US07956088-20110607-P00001.TIF" alt="custom character" img-content="character" img-format="tif" ?-methylene-img id="CUSTOM-CHARACTER-00009" he="3.13mm" wi="1.78mm" file="US07956088-20110607-P00001.TIF" alt="custom character" img-content="character" img-format="tif" ?-butyrolactones: a structure-activity relationship study of their allergenic power,”J. Med. C

Affiliated with

Also associated with

Rating

Synthetic lactone formulations and methods of use does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthetic lactone formulations and methods of use, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthetic lactone formulations and methods of use will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2734555