Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-12-30
2000-09-26
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549282, 549285, 549334, 549338, C07D30778, C07D31178, C07D31772, C07D40714
Patent
active
061244775
ABSTRACT:
The present inventor has discovered chemical compounds which inhibit the first-pass effect of orally administered drugs in humans; that phototoxic low molecular weight furocoumarins and certain ether-substituted furocoumarins that are naturally present in citrus extracts, juices, byproducts, etc. may be removed therefrom or reduced in concentration without destroying the first-pass effect inhibiting compounds therein, and a method for preparing citrus-based compositions using only FDA or USP acceptable reagents.
REFERENCES:
patent: 1840798 (1932-01-01), Tressler
patent: 3071474 (1963-01-01), Gross
patent: 3300320 (1967-01-01), Distelkamp et al.
patent: 3917865 (1975-11-01), Shaw et al.
patent: 4497838 (1985-02-01), Bonnell
patent: 4562087 (1985-12-01), Kryger
patent: 4569853 (1986-02-01), Strobel
patent: 4749798 (1988-06-01), Gandolfi et al.
patent: 5061502 (1991-10-01), Cully et al.
patent: 5229116 (1993-07-01), Edgar et al.
patent: 5356929 (1994-10-01), Heindel et al.
patent: 5362714 (1994-11-01), Radford et al.
patent: 5478723 (1995-12-01), Parkinson et al.
patent: 5494681 (1996-02-01), Cuca et al.
patent: 5567592 (1996-10-01), Benet et al.
Derek E. Wright, "The Orthosomycins, A New Family Of Antibiotics", Tetra, vol. 35, No. 10, pp. 1207-1237, 1979.
Ashit K. Ganguly, et al., "Determination Of The Absolute Sterochemistry At The C16 Orthoester Of Enverninomicin Antibiotics; A Novel Acid-Catalyzed Isomerization Of Orthoesters", Tetrahedron Letters, vol. 38, No. 46, pp. 7989-7992, 1997.
David J. Collins, et al., "Enolic Ortho Esters. I Preparation and Birch Reduction of Some Coumarinoid Ortho Esters", Aust. J. Chem., vol. 42, pp. 1235-1248, 1989.
J. Gervais, et al., "Photochemistry of Some Furo (3,2-g)-Coumarin and 2,3-Dihydrofuro (3,2-g)-Coumarin Derivatives", Photochemistry and Photobiology, vol. 21, pp. 71-75, 1975.
Yingna Cai, et al. "Inhibition and Inactivation of Murine Hepatic Ethoxy-and Pentoxyresorufin O-Dealkylase by Naturally Occurring Coumarins", Chem. REs. Toxicol, vol. 6, No. 6, pp. 872-879, 1993.
Won Sick Woo, et al., "Isolation of Drug Metabolism Modifiers from Roots of Angelica Koreana.sup.1 ", Journal of Medicinal Plant Research, vol. 45, pp. 234-236, 1982.
J. Owusu-Yaw, et al.,"Alcohol Deterpenation of Orange Oil", 1986, vol. 51, No. 5, pp. 1180-1182.
J.J. Neal, et al., "Inhibition of Insect Cytochromes P450 by Furanocoumarins", 1994, Pesticide Bioshemistry and Physiology 50, pp. 43-50.
Motoharu Ju-ichi, et al., "The Structures of Claudimerines-A and -B, Novel Bicoumarins from Citrus hassaku.sup.1) ", Jan. 1996, vol. 44, No. 1 pp. 11-14.
Yuko Takemura, et al., "Structure of Furobinordentatin, A Novel Bicoumarin From Citris Yuko", Chem. Pharm. Bull. vol. 42, No. 4, pp. 997-998, Apr. 1994.
Yuko Takemura, et al., "Structures of Furobinordentatin and Furobiclausarin, Two Novel Bicoumarins from Citrus Plants.sup.1) ", Chem. Pharm. Bull. vol. 42, No. 12, pp. 2436-2440, Dec. 1994.
Yuko Takemura, et al., "Three New Bicoumarins from Citrus hassaku.sup.1) ", Chem. Pharm. Bull. vol. 42, No. 6, pp. 1213-1215, Jun. 1994.
Chihiro Ito, et al., "Structure of Bisosthenon, a Novel Dimeric Coumarin from Citrus Plants.sup.1) ", Aug. 1990, vol. 38, No. 8, pp. 2102-2107.
Chihiro Ito, et al., "Isolation of New Constituents from Citrus Plants", Sep. 1990, vol. 38, No. 9, pp. 2586-2588.
Chihiro Ito, et al., "Structure of Bisosthenon, A Novel Dimeric Coumarin From Citrus Plants.sup.1)", vol. 37, No. 1, pp. 1957-1959, 1989.
Yuko Takemura, et al., "Citbismine-A, A New Bisacridone Alkaloid from Citrus Paradisi", Jul. 1994, vol. 42, No. 7, pp. 1548-1549.
Yuko Takemura, et al., "Three New Acridone-Coumarin Dimers From A Citrus Plant.sup.1 ", 1994, vol. 38, No. 8, pp. 1937-1941.
Chihiro Ito, et al., "A New Biscoumarin from Citrus Plants", Sep. 1993, vol. 41, No. 9, pp. 1657-1658.
R.D.H. Murray, Natural Product Reports, "Coumarins", 1989, vol. 6, pp. 477-505.
Sudam C. Basa, Phytochemistry, "Natural Bicoumarins", Nov. 9, 1987, vol. 27, No. 7, pp. 1933-1941.
P.R. Ashurst, et al., Food Flavorings Second Edition, 1995, 3pp.
Gary C. Yee, The Lancet, "Effect of Grapefruit Juice on Blood Cyclosporin Concentration", Apr. 15, 1995, vol. 345, pp. 955-956.
Sigusch et al, "Influence of Grapefruit juice on the Pharmacokinetics of a Slow Release Nifedipine Formulation", Pharmazie 49, 1994, pp. 522-524.
Abigail Zuger, "How Grapefruit Juice Makes Some Pills More Powerful", The New York Times, Oct. 7, 1997, 2pp.
Chihiro Ito, et al., "New Binary Coumarins from Citrus Plants", Chem. Pharm. Bull. vol. 38, No. 5, pp. 1230-1232, 1990.
Yuko Takemura, et al., "Structural Elucidation of Citrumarins: Four Novel Binary Coumarins Isolated from Citrus Plants", Chem. Pharm. Bull. vol. 41, No. 1, pp. 73-76, 1993.
Chihiro Ito, et al., Structure of Hassmarin, a Novel Biscoumarin from a Citrus Plant.sup.1), Chem. Pharm. Bull. , Jul. 1993, vol. 41, No. 7, pp. 1302-1304.
F. Peter Guengerich, et al., "In vitro inhibition of dihydropyridine oxidation and aflatoxin B.sub.1 activation in human liver microsomes by naringennin and other flavonoids", Carcinogenesis, vol. 11, No. 12, pp. 2275-2279, 1990.
David G. Bailey, et al., "Grapefruit Juice and Drugs", Clin. Pharmacokinet, vol. 26, No. 2, pp. 91-98, 1994.
David J. Edwards, et al., "Identification of 6',7'-Dihydroxybergamottin, A Cytochrome P450 Inhibitor, in Grapefruit Juice", Drug Metabolism and Disposition, vol. 24, No. 12, pp. 1287-1290, 1996.
Barbara Aneer, et al., "Drug Interactions with Grapefruit Juice", Clin. Pharmacokinet, vol. 33, No. 2, pp. 103-121, Aug. 1997.
Katsuyuki Fukuda, et al., "Grapefruit Component Interacting with Rat and Human P450 CYP34: Possible Involvement of Non-Flavonoid Components in Drug Interaction", Biol. Pharm. Bull., vol. 20, No. 5, pp. 560-564, May 1997.
Frank H. Bellevue, et al., "Synthesis and Biological Evaluation of 6',7'-Dihydroxybergamottin (6,7-DHB), A Naturally Occurring Inhibitor of Cytochrome P450 3A4", Bioorganic & Medicinal Chemistry Letter, vol. 7, No. 20, pp. 2593-2598, 1997.
David J. Edwards, et al., "Naringin and Naringenin are not the Primary CYP3 A Inhibitors in Grapefruit Juice", Life Sciences, vol. 59, No. 13, pp. 1025-1030, 1996.
M. Bourian, et al., "Coumarin Derivatives in Grapefruit Juice and Their Interactions with Mammalian Drug Metabolising Enzyme Systems", Annual Congress on Medicinal Plant Research, vol. 44, pp. 73, 1996.
William K. Chan, et al., "Mechanism-Based Inactivation of Human Cytochrome P450 3A4 by Grapefruit Juice and Red Wine", Life Sciences, vol. 62, No. 10, pp. PL 135-142, 1998.
Kan He, et al., "Inactivation of Cytochrome P450 3A4 by Bergamottin, a Component of Grapefruit Juice", Chem. Res. Toxicol, vol. 11, pp. 252-259, 1998.
M.T. Obermeier, et al., "Effects of bioflavonoids on hepatic P450 activities", Xenobiotica, vol. 25, No. 6, pp. 575-584, 1995.
Marina Tinel, et al., "Inactivation of Human Liver Cytochrome P-450 by the Drug Methoxsalen and Other Psoralen Derivatives", Biochemical Pharmacology, vol. 36, No. 6, pp. 951-955, 1987.
R. Chayen, et al., "Interaction of citrus juices with felodipine and nifedipine", The Lancet, vol. 337, Apr. 6, 1991.
Phyllissa Schmiedlin-Ren, et al., "Mechanisms of Enhanced Oral Availability of CYP3A4 Substrates by Grapefruit Constituents", Drug Metabolism and Disposition, vol. 25, No. 11, pp. 1228-1233, 1997.
Katsuyuki Fukuda, et al., "Specific CYP3A4 inhibitors in grapefruit juice: furocoumarin dimers as components of drug interaction", Pharmacogenetics, vol. 7, pp. 391-396, 1997.
Barbara Ameer, et al., "Flavanone absorption after naringin, hesperidin, and citrus administration", Clinical Pharmacology & Therapeutics, vol. 60, No. 1, pp. 34-40, Jul. 1996.
J. Rashid, et al., "Quercetin, an in vitro inhibitor of CYP3A, does not contribute to the interaction between nifedipine and grapefruit juice", Br J clin Pharmac, vol. 36, pp. 460-463, 1993.
David G. Bailey, et al., "Grapefruit juice-felodipine interaction: Mechanism, predictability, and effect of naringin", Clinical Pharmacology & Therapeutics, vol. 53, No. 6, pp. 637-642, Jun. 1993.
David G. Bailey, et al., "Effect o
Bioavailability Systems, LLC
Richter Johann
Solola Tadfiq A.
LandOfFree
Anti-first-pass effect compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Anti-first-pass effect compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Anti-first-pass effect compounds will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2101412