Fluorocyclosaccharide drug delivery systems

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

424 935, 536103, A61K 31175, A61K 5100, C08B 3716

Patent

active

057391211

ABSTRACT:
Novel fluorine-containing cyclic saccharide compounds, in particular fluorocyclodextrin compounds, and drug inclusion complexes of these compounds, as well as methods for preparation of the novel fluorine-containing cyclic saccharide compounds, including fluorocyclodextrins, and drug inclusion complexes of the compounds. In addition, methods for following the disposition and fate in vivo of drug inclusion complexes of the invention.

REFERENCES:
patent: 5068227 (1991-11-01), Weinshenker
Szejtli, J. "Medicinal Applications of Cyclodextrins", from Medicinal Research Reviews, vol. 14(3):353-386, (1994).
Carbohydrates, Ed. by P.M Collins, Publ. Chapman & Hall, pp. 150-151, (1987).
Wright et al., J. Org. Chem., vol. 34:2632, (1969).
Carbohydrate Research, vol. 143: 106-117, (1985).
Naser-Hijazi, B. Hull. Locoregional Adminstration of 5-fluoro-2'-deoxyuridine (FdUrd) in Novikoff Hepatoma in the Rat: Effects of Dose and Infusion Time on Tumor Growth and on FdUrd Metabolite Levels in Tumor Tissue as Determined by .sup.19 F-NMR Spectroscopy. J. Cancer Res. Clin. Oncol., 117, 295-304 (1991).
Koutcher, J.A., In Vivo Monitoring of Changes in 5-FluorouracilMetabolism Induced by .sup.19 F-NMR Spectroscopy. Magnetic Resonance in Med., 19, 113-123 (1991).
Port, R.E., B. Bachert and W. Semmler. Kinetic Modeling of in vivo-Nuclear Magnetic Resonance Spectroscopy Data: 5-Fluorouracil in Liver and Liver Tumors. Clin. Pharmacol. Ther., 49, 497-505 (1991).
McSheehy, P.M.J., M.J.W. Prior and J.R. Griffiths. Prediction of 5-Fluorouracil Cytotoxicity Towards the Walker Carcinosarcoma Using Peak Integrals of Fluoronucleotides Measured by MRS in vivo Br. J. Cancer, 60, 303-309 (1989).
Zhang, R., S-J Soong, T. Liu, S. Barnes and R.B. Diasio, Pharmacokinetics and Tissue Distribution of 2-Fluoro-.beta.-alanine in Rats. Potential Relevance to Toxicity Pattern of 5-Fluorouracil. Drug Metab. and Disp., 20, 113-119 (1992).
Maxwell, R.J., T.A. Frenkiel, D.R. Newell, C. Bauer and J.R. Griffiths. .sup.19 F Nuclear Magnetic Resonance Imaging of Drug Distribution in Vivo: The Disposition of an Antifolate Anticancer Drug in Mice. Magnetic Resonance in Med., 17, 196 (1991).
Thomas, C., C. Counsell, P. Wood and G.E. Adams. Use of Fluorine-19 Nuclear Magnetic Resonance Spectroscopy and Hydralazine for Measuring Dynamic Changes in Blood Perfusion Volume in Tumors in Mice. J.N.C.I., 84, 174-180 (1992).
Tandon, M., P. Kumar, G. Wiebe and L.I. Wiebe. Detection of New Metabolites of Trifluridine (F.sub.3 TdR) Using .sup.19 F NMR Spectroscopy. Biochem. Pharmacol., 44, 2223-2228 (1992).
Tandon, M., P. Kumar and L.I. Wiebe. .varies.-Trifluoromethyl-.alpha.-ureido-proprionic acid (F.sub.3 MUPA) : a new metabolite of trifluridine (F.sub.3 TdR). Nucleosides and Nucleotides., 12(8) in press (1993).
Tandon, M., P. Kumar and L.I. Wiebe, .varies.-Trifluoromethly-.alpha.-alanyl glycine (F.sub.3 MBAG): A novel metabolite of trifluorouridine (F.sub.3 TdR). (submitted).
Heidelberger, D., J. Boohar and B. Kampschoer. Fluorinated Pyrimidines XXIV in vivo Metabolism of 5-Trifluoromethyluracil-2-14-C and 5-Trifluoromethyl-2'-deoxyuridine-2-14-C. Cancer Res., 25, 377-381 (1964).
Cramer, F. and H. Hettler. Inclusion Compounds of Cyclodextrins. Naturwissenschaften, 54, 624-632 (1967).
Uekama, K. Pharmaceutical Applications of Methylated Cyclodextrins. Pharm. Int., Mar., 61-64 (1985); Uekema, K. and Otagiri, M. Cyclodextrins in Drug Cancer Systems. CRC Cric. Rev. Therap. Drug Cancer Systems, 3, 1 (1987).
Green, A.R. and J.K. Guillory. Heptakis (2,6-di-O-methyl)-.beta.-cyclodextrin Complexation with Antitumor Agent Chlorambucil. J. Pharm. Sci., 78, 427-341 (1989).
Brewster, M.E., J.W. Simpkins, M. S. Hora, W.C. Stern and N. Bodor. The Potential Use of Cyclodextrins in Parenteral Formulations. J. Parenteral Sci. and Tech., 43, 231-240 (1989).
Pitha, J. et al. Hydroxypropyl-.beta.-cyclodextrin: Preparation and Characterization; Effects on Solubility of Drugs, Int. J. Pharm., 29, 73-82 (1986).
Szejtli, J., A. Liptak, I. Jodal, P. Fugedi, P. Nanasi and A. Neszmelyi. Synthesis and .sup.13 C-NMR Spectroscopy of Methylated beta-Cyclodextrins. Starch/Starke,32, 165-169 (1980).
Valsami, G.N. et al. Complexation Studies of Cyclodextrins with Tricyclic Antidepressants Using Ion-selective Electrodes. Pharm. Res., 9, 94-100 (1992).
Frijlink, H.W. et al. The Pharmacokinetics of .beta.-cyclodextrin in the Rat. Pharm. Res., 7, 1248-1252 (1990).
Frijlink, H.W. et al. The Effect of Cyclodextrins on the Disposition of Intravenously-injected Drugs in the Rat. Pharm. Res., 8, 380-384 (1991).
Loftsson, T. and B.J. Olafsdottir. Cyclodextrin-accelerated Degradation of .beta.-lactain Antibiotics in Aqueous Solution. Int. J. Pharm., 67, R5-7 (1991).
Irie, T., K. Fukunaga, A. Yoshida, K. Uekama, H. Fales and J. Pitha. Anorphorus Water-soluble Derivatives of Cyclodextrins: 2-Hydroxyethyl, 3-Hydroxypropyl, 2-Hydroxyisobutyl and Carboxamidomethyl Derivatives of .beta.-cyclodextrin. Pharm. Res., 5, 713-719 (1988).
Brereton, I.M., T.M. Spotswood, S.F. Lincoln and E.H. Williams. Fluorine-19 Magnetic Resonance Study of the Inclusion of Fluoro-and Difluoro-trans-cinnamates by .alpha.-cyclodextrin. J. Chem. Soc., Faraday Trans., 1, 80, 3147-3156 (1984).
Lincoln, S.F., A.M. Hounslow, J.H. Coates and B.G. Dodderidge. The Inclusion of Difluorisal by .alpha. and .beta.-Cyclodextrins. A .sup.19 F Nuclear Magnetic Resonance and Spectrophotometric Study. J. Chem. Soc. Faraday Trans., 1, 83, 2697-2703 (1987).
Pisaniello, D.L., S.F. Lincoln and J.H. Coates. The Inclusion of Haloperidol and Trifluperidol by .alpha.- and .beta.-cyclodextrins. J. Chem. Soc. Faraday Trans., 1, 81, 1247-1253 (1985).
Smith, N.J. T.M. Spostwood and S.F. Lincoln. The Inclusion of the Enantiomers of N-Trifluoroacetyl-4-fluorophenylalanine and N-Trifluoroacetylphenylalanine by cyclomaltohexose a .sup.2 H and .sup.19 F-N.M.R. Study. Carbohydr. Res., 192, 915 (1989).
Brown, S.E., J.H. Coates, S.F. Lincoln, D.R. Coghlan and C.J. Easton. Chiral Molecular Recognition: A .sup.19 F Nuclear Magnetic Resonance Study of the Diastereoisomer Inclusion Complexes formed between Fluorinated Amino Acid Derivative and .alpha.-Cyclodextrin in Aqueous Solution. J. Chem. Soc. Faraday Trans., 1, 87, 2699-2703 (1991).
Card, P.J. Fluorinated Carbohydrates. Use of (diethylamine) sulfur trifluoride in the synthesis of fluorinated sugars. J. Org. Chem., 48, 393-395 (1983).
Kumadaki, I. A review in Yakugaku Zasshi, 4095 (1969), cited in "Synthetic Procedures in Nucelic Acid Chemistry", vol. I, ed. by W.W. Zorbach and R.S. Tipson, Pub. Interscience Publishers (1968).
Glaudemans, C.P.J. and Fletcher, H.G. Jr. J. Org. Chem., 28, 3004 (1963), cited in "Synthetic Procedures in Nucelic Acid Chemistry", vol. I, ed. by W.W. Zorbach and R.S. Tipson, Pub. Interscience Publishers (1968).
Reist, E.J., Benitez A., Goodman, L., Baker, B.R. and Lee, W.W. J. Org. Chem., 27, 3274 (1962), cited in "Synthetic Procedures in Nucelic Acid Chemistry", vol. I, ed. by W.W. Zorbach and R.S. Tipson, Pub. Interscience Publishers (1968).
Reichman, U., Watanabe, K.A. and Fox. J.J. A practical synthesis of 2-deoxy-2-fluoro-D-arabinofuranose derivatives. Carbohydr. Res., 42, 233-240 (1975).
Grierson, J.R., Link, J.M., Mathis, C.A., Rasey, J.S. and Krohn, K.A. A Radiosynthesis of Fluorine-18 fluoromisonidazole. J. Nuc. Med., 30, (3), 343-350 (1989).
Shimada, K., Fukuda, T.T. Japan Kokai, 75, 46, 825 (1975) cited in "Cyclodextrins and Their Inclusion Complexes" by J. Szejtli., Publ. Akademiai Kiado, Budapest, p100 (1982).
Hoffman, J.L. and R.M. Bock. The Interaction of Cyclodextrins with Nucleic Acids. A Study of Secondary Structure in Three Transfer Ribonucleic Acids. Biochem., 9, 3542-3550 (1970).
Taylor, N.F., Childs, R.F. and Brunt, R.V. Synthesis of methyl 3-deoxy-3-fluoro-.beta.-L-xylopyranoside, Chem. Ind. 928 (1964).
Breslow, R., Czarnleckl, M.F., Amert, J. and Hamaguchi, H.J. Amer. Chem. Soc., 102, 762 (1980).
Tsujihara, K. and Kurita, H., Chem. Lett. 1333 (1978).
Cramer, F., Mackensen, G. and Sensse, K., Chem. Ber., 102, 494 (1969).
Takeo, K., Suimimoto, T. and Kuge,

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Fluorocyclosaccharide drug delivery systems does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Fluorocyclosaccharide drug delivery systems, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fluorocyclosaccharide drug delivery systems will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-634684

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.