Patent 5472954 Issued on December 5, 1995. Estimated Expiration Date: May 11, 2014. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.
514/58, Dextrin or derivative514/772.2, Polyvinyl alcohol514/772.3, Solid synthetic organic polymer514/772.6, Carboxylic acid containing monomer514/773, Peptide containing514/777, Carbohydrate or lignin, or derivative514/779, Algin or derivative514/781, Cellulose or derivative536/103Dextrin or derivative
The invention provides a method for enhancing the complexation of a cyclodextrin with a lipophilic and/or water-labile active ingredient which is a drug, cosmetic additive, food additive or agrochemical, comprising combining from about 0.1 to about 70% (weight/volume) of a cyclodextrin, from about 0.001 to about 5% (weight/volume) of a pharmacologically inactive water-soluble polymer acceptable for use in a pharmaceutical, cosmetic, food or agricultural composition, and said lipophilic and/or water-labile active ingredient in an aqueous medium, the polymer and cyclodextrin being dissolved in the aqueous medium before the active ingredient is added, the aqueous medium which comprises the polymer and cyclodextrin being maintained at from about 30° to 150° C. for a period of from about 0.1 to about 100 hours before, during and/or after the active ingredient is added, optionally followed by removal of water. Related methods, co-complexes of active ingredient/cyclodextrin/polymer, pharmaceutical, cosmetic, food and agricultural compositions and cyclodextrin/polymer complexing agents are also provided.
Other References
Villiers, C. R. Acad. Sci., 112, 536-538(1891)
Schardinger, Z Unters. Nahr. Genussm., 6, 865-880(1903)
Szejtli, Pharm. Techn. Int., 3(2), 15-22(1991)
Szejtli, Pharm. Techn. Int., 16-24(1991)
Loftsson et al, Pharm. Ztg. Wiss., 4/136:5-10(1991)
Hirayama et al, in Cyclodextrins and their industrial uses, ed. D. Duchene, Editions de Sante, Paris, 1987, pp. 133-172
Hassan et al, Int. J. Pharm. 58, 19-24(1990)
Nakai et al, Chem. Pharm. Bull, 35(11), 4609-4615(1987)
Nakai et al, Chem. Pharm. Bull, 37(4), 1055-1058(1989)
Nakai et al, Chem. Pharm. Bull, 38(3), 728-732(1990)
Nakai et al, Chem. Pharm. Bull., 38(5), 1345-1348(1990)
Nakai et al, Chem. Pharm. Bull., 39(6), 1532-1535(1991)
Schmidt et al, Starch/Starke, 39(6), 203-207 (1987)
Loftsson et al, Acta. Pharm. Nord, 1(4), 185-193(1989)
Remington's Pharmaceutical Sciences, 18th edition, Alfonso R. Gennaro (ed.), Mack Publishing Co., Easton, Pa., 1990, pp. 291-294
Martin et al, Physical Pharmacy, 3rd edition, Lea & Febinger, Philadelphia, Pa. 1983, pp. 592-638
Florence et al, Physiochemical Principles of Pharmacy, 2nd edition, MacMillan Press, London, 1988, pp. 281-334
Leung et al, in Controlled Drug Delivery, 2nd edition, Robinson and Lee, editors, Marcel Dekker, Inc., New York, 1987, pp. 433-480
Uekama et al, Journal of Inclusion Phenomena, 1, 309-312(1984)
Pagington, J. S., "ଲ-cyclodextrin: the success of molecular inclusion," in Chemistry in Britain, May 1987, 455-458
Loftsson et al, Eur. J. Pharm. Biopharm., vol. 37, No. 1, Mar. 1991, 30-33
STN FILE SUPPLIER & FILE MEDLINE AN=92324215 (Orienti et al)
Chemical Abstracts, vol. 107, No. 16, 1987, abstract No. 140916f
THE MERCK INDEX, eleventh edition, ed. Susan Budavari et al, Merck & Co., Inc. Rahway, N.J., 1989, pp. 959, 1248 and 1467
COSMETIC AND DRUG PRESERVATION: PRINCIPLES AND PRACTICE, ed. Jon J. Kabara, Marcel Dekker, Inc., New York, N.Y., 1984, pp. 71-72
THE UNITED STATES PHARMACOPEIA, USP XXII, twenty-second revision, Jan. 1, 1990, U.S. Pharmacopeial Convention, Inc. Rockville, Md., p. 8
Loftsson et al, European Journal of Pharmaceutical Sciences, 1(1994), 175-180
Loftsson et al, International Journal of Pharmaceutics, 104(1994), 181-184
Loftsson et al, "Topical acetazolamide-HP eye drop solution," in Final Program and Abstracts for the 7th International Cyclodextrins Symposium, Tokyo, Japan, Apr. 25-28, 1994, p. 112, abstract P-B-25
Loftsson et al, "Dexamethasone 2-hydroxypropyl-ଲ-cyclodextrin eye drops," In Final Program and Abstracts for the 7th International Cyclodextrins Symposium, Tokyo, Japan, Apr. 25-28, 1994, p. 113, abstract P-B-26
Loftsson et al, "The Effect of Polymers on Cyclodextrin Complexation," in Final Program and Abstracts for the 7th International Cyclodextrins Symposium, Tokyo, Japan, Apr. 25-28, 1994, p. 114, abstract P-B-27
Stefansson et al, "Dexamethasone 2-Hydroxypropyl-ଲ-cyclodextrin (HP) Eye Drops," in Investigative Ophthalmology & Visual Science, Annual Meeting Abstract Issue, Mar. 15, 1994, vol. 35, No. 4, p. 2217, abstract 4459-11
Thorisdottir et al, "Topical Acetazolamide in 2-Hydroxypropyl-ଲ-Cyclodextrin (HP) Eye Drops Lowers Intraocular Pressure in Humans," in Investigative Ophthalmology & Visual Science, Annual Meeting Abstract Issue, Mar. 15, 1994, vol. 35, No. 4, p. 2220, abstract 4479-4531
Florence et al, Physiochemical Principles of Pharmacy, 2nd ed., Macmillan Press, London 1988, pp. 24, 297-298
Chien, Novel Drug Delivery Systems, 2nd Ed., Marcel Dekker, New York 1992, pp. 171-173
Peppas et al, "Surface, interfacial and molecular aspects of polymer bioadhesion on soft tissues," in J. M. Anderson and S. W. Kim (editors), Advances in Drug Delivery Systems, Elsevier, Amsterdam 1986, pp. 257-275
Attwood et al: Surfactant Systems. Their Chemistry, Pharmacy and Biology, Chapman and Hall, London, 1983, pp. 361-365
Myers, Surfactant Science and Technology, VCH Publishers, New York, 1988, pp. 142-14
May 11, 2014. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.
