Cubic liquid crystalline compositions and methods for their preparation
Patent 6773627 Issued on August 10, 2004. Estimated Expiration Date: December 4, 2023. 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.
Cubic liquid crystalline gel precursors, bulk cubic liquid crystalline gels, and dispersions of cubic liquid crystalline gel particles, and methods for their preparation, are disclosed. The precursors, gels, and dispersions can be used as skin penetration enhancers. The precursors, gels, and dispersions are prepared by methods employing hydrotropes that do not detrimentally affect the cubic liquid crystalline structure of the gels and particles.
Other References
Alfons and Engstrom, “Drug Compatibility with the Sponge Phases Formed in Monolein, Water, and Propylene Glycol or Poly(ethylene glycol),” J. Pharm. Sci. vol. 87, No. 12, 1527-1530 (Dec. 1998).
Fontell, “Cubic phases in surfactant and surfactant-like lipid systems,” Colloid. Polym. Sci. 268:264-285 (1990).
Tabony, “Formation of cubic structures in microemulsions containing equal volumes of oil and water,” Nature, vol. 319, 400 (Jan. 30, 1986).
Brown, ed., Advances in Liquid Crystals, vol. 1, Ekwall, “Composition, Properties and Structures of Liquid Crystalline Phases in systems of Amphiphilic Compounds,” pp 1-139, Academic Press (1975).
Lindblom et al., “Phase Equilibria of Membrane Lipids from Acholeplasma laidlawii: Importance of a Single Lipid Forming Nonlamellar Phases,” Biochemistry 25, 7502-7510 (1986).
Engström et al., “A study of polar lipid drug carrier systems undergoing a thermoreversible lamellar-to-cubic phase transition,” Int. J. Pharmaceutics, 86 137-145 (1992).
Engström et al., “Phase behavior of the lidocaine-monoolein-water system,” Int. J. Pharmaceutics, 79 113-122 (1992).
Angelov, et al., “X-ray Diffraction Study of the Effect of the Detergent Octyl Glucoside on the Structure of Lamellar and Nonlamellar Lipid/Water Phases of Use for Membrane Protein Reconstitution,” Langmuir, 15, 8225-8234, 1999.
Aota-Nakano, et al., “Effects of electrostatic interaction on the phase stability and structures of cubic phases of monoolein/oleic acid mixture membranes,” Biochimica et Biophysica Acta, 1461, 96-102, 1999.
Bellare, J.R.; Davis, H.T.; Scriven, L. E.; Talmon, Y., “Controlled environment vitrification technique,” J. Electron Microsc. Tech., 10, 87-111, 1988.
Briggs, et al., “The Temperature-Composition Phase Diagram and Mesophase Structure Characterization of the Monoolein/Water System,” J. Phys. II France, 6, 723-751, 1996.
Chang, et al., “Binding of drugs to monoglyceride based drug delivery systems,” International Journal of Pharmaceutics, 147, 135-142, 1997.
Drummond, et al., “Surfactant Self-Assembly Objects as Novel Drug Delivery Vehicles,” Current Opinion in Colloid and Interfacial Science, 4, 449-456, 2000.
Evans, The Colloidal Domain. 2nd ed., Wiley, NY, pp. 575-588, 1999.
Funari,S. S. and Gert, R., “X-ray Studies on the C12EO2/Water System”, J. Phys. Chem. B, 101, 732, 1997.
Gustafsson, et al, “Submicron Particles of Reversed Lipid Phases in Water Stabilized by a Nonionic Amphiphilic Polymer,” Langmuir, 13, 6964-6971, 1997.
Gustafsson, et al. “Phase Behavior and Aggregate Structure in Aqueous Mixtures of Sodium Cholate and Glycerol Monooleate,” Journal of Colloid and Interface Science, 211, 326-335, 1999.
Gustafsson, et al. “Defective Lamellar Phases and Micellar Polymorphism in Mixtures of Glycerol Monooleate and Cetyltrimethylammonium Bromide in Aqueous Solution,” Langmuir, 14. 4987-1996, 1998.
Hecht, E., Optics, 2nd ed., Addison-Wesley Publishing Co., Reading, Massachusetts, pp. 282-289, 1984.
Hyde et al., The Language of Shape, Elsevier Amsterdam, chapters 1 and 4, 1997.
Landh, “Phase Behavior in the System Pine Oil Monoglycerides-Poloxamer 407-Water at 20 C” J. Phys. Chem., 98 8453-8467, 1994.
Landau, et al., “Lipidic cubic phases: A novel concept for the crystallization of membrane proteins,” Proc. Natl. Acad. Sci. USA, 93, 14532-14535, 1996.
Laughlin, R.G., J. Colloid Interface Sci., 55 239-242, 1976.
Laughlin, R.G., The Aqueous Phase Behavior of Surfactants, Academic Press, New York, pp. 255 and 521-546, 1994.
Lee, et al., “Combined effect of oleic acid and polyethylene glycol 200 on buccal permeation of [D-Ala2, D-Leu5]enkephalin from a cubic phase of glyceryl monooleate,” International Journal of Pharmaceutics, 204, 137-144, 2000.
Lndell, et al., “Influence of a charged phospholipid on the release pattern of timolo maleate from cubic liquid crystalline phases.” S. Prog. Colloid Polym. Sci., 108, 111-118, 1998.
Lipowsky, et al., eds., “The Structure and Conformation of Amphiphilic Membranes,” Proceedings of the International Workshop on Amphiphilic Membranes, Julich, Germany, Sep. 16-18, 1991. Templer, et al. “Swollen Lyotropic Cubic Phases in Fully Hydrated Mixtures of Monoolein. Dioleoylphosphatidylcholine, and Dioleoylphosphatidylethanolamine.” 262-265.
Luzzati et al., J. Mol. Biol., 229, 540-551, 1993.
Lynch et al., “Aqueous Phase Behavior and Cubic Phase-Containing Emulsions in the C12E2-Water System,” Langmuir, vol. 16, No. 7, pp. 3537-3542, 2000.
Pearson, J. T., Smith, J. M., “The Effect of Hycrotropic Salts on the Stability of Liquid Crystalline Systems,” J. Pharm. Pharmac., 26, 123-124, 1974.
Pitzalis, et al., “Characterization of the Liquid-Crystalline Phases in the Glycerol Monooleate/Diglycerol Monooleate/Water System,” Langmuir 16, 6358-6365, 2000.
Puvvada, et al., “Ionotropic Gelation in a Bioowtinuous Cubic Phase,” J. Phys. Chem. , 97, 11103-11107, 1993.
Razumas, et al., “A Cubic Monoolein-Cylochrome c-Water Phase: X-ray diffraction, FT-IR Differential Scanning Calorimetricm, and Electrochemical Studies,” J. Phys. Chem., 100, 11766-11774, 1996.
Razumas et al., “Effects of distearoylphosphosphatixtylglycerol and lysozyme on the structure of the monoolein-water cubic phase: X-ray diffraction and Raman scattering studies,” Chemistry and Physics of Lipids, 84, 123-138, 1996.
Razumas, et al., “Structural characteristics and redox activity of the cubic monoolein/ubiquinone-10/water phase,” Progr. Colloid Polym. Sci., 108, 75-82, 1998.
Rummel, et al., “Lipid Cubic Phases: New Matrices for the Three-Dimensional Crystallization of Membrane Proteins,” Journal of Structural Biology . 121, 82-91, 1998.
Rosevear, F.B., J. Am. Oil Chemists Soc., 31, 628-638, 1954.
Soderberg, et al., “Phase properties and structure of a monoglyceride/sucroses/water system,” Chemistry and Physics of Lipids, 55, 97-101, 1990.
Winey, Thomas and Fetters, “Morphologies in Binary Blends”, J. Chem. Phys., vol. 95, No. 12, Pg. 9368, 1991.
J.S. Kim, et al., Drug Formulations that Form a Dispersed Cubic Phase when Mixed with Water, Proceed. Int'l. Symp. Control. Rel. Bioact. Mater., 27 (2000) Controlled Release Society, Inc., pp. 1118 & 1119.
December 4, 2023. 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.
