Solution-Based Particle Formation of Pharmaceutical Powders by Supercritical or Compressed Fluid Co₂ and Cryogenic Spray-Freezing Technologies

REFERENCES

• Palakodaty S., York P. Phase Behavioral Effects on Particle Formation Processes Using Supercritical Fluids. Pharm. Res. 1999; 16: 976–985
   PubMed Web of Science ®Google Scholar
• Dixon D. J., Johnston J. P., Bodmeier R. A. Polymeric Materials Formed by Precipitation with a Compressed Fluid Antisolvent. AIChE J. 1993; 39: 127–139
   Web of Science ®Google Scholar
• Reverchon E. Supercritical Antisolvent Precipitation of Micro- and Nano-particles. J. Supercrit. Fluids 1999; 15: 1–21
   Web of Science ®Google Scholar
• McHugh M. A., Krukonis V. J. Supercritical Fluid Extraction Principles and Practice. 2nd, Butterworth-Heinemann, Woburn, MA 1994
   Google Scholar
• Subramaniam B., Rajewski R. A., Snavely K. Pharmaceutical Processing with Supercritical Carbon Dioxide. J. Pharm. Sci. 1997; 86: 885–890
   PubMed Web of Science ®Google Scholar
• Kikic I., Sist P. Applications of Supercritical Fluids to Pharmaceuticals: Controlled Drug Release Systems. Second NATO ASI on Supercritical Fluids. 1998. KemerTurkey
   Google Scholar
• Reverchon E. Supercritical Antisolvent Precipitation: Its Application to Microparticle Generation and Products Fractionation. Proceedings of the Fifth Meeting on Supercritical Fluids Materials and Natural Products Processing, France, 1998. Nice, 1: 221–236
   Google Scholar
• Benedetti L., Bertucco A., Pallado P. Production of Micronic Particles of Biocompatible Polymer Using Supercritical Carbon Dioxide. Biotechnol. Bioeng. 1997; 53: 232–237
   PubMed Web of Science ®Google Scholar
• Bertucco A., Pallado P., Benedetti L. Formation of Biocompatible Polymer Microspheres for Controlled Drug Delivery by a Supercritical Antisolvent Technique. Process Technology Proceedings 12, High Pressure Chemical Engineering, P. R.V. Rohr, C. Trepp. Elsevier, AmsterdamThe Netherlands 1996; 217–222
   Google Scholar
• Bodmeier R., Wang J., Dixon D. J., Mawson S., Johnston K. P. Polymeric Microspheres Prepared by Spraying into Compressed Carbon Dioxide. Pharm. Res. 1995; 12: 1211–1217
   PubMed Web of Science ®Google Scholar
• Sarkari M., Darrat I., Knutson B. L. Generation of Microparticles Using CO2 and CO2-Philic Antisolvents. AIChE J. 2000; 46: 1850–1859
   Web of Science ®Google Scholar
• Lengsfeld C. S., Delplanque J. P., Barocas V. H., Randolph T. W. Mechanism Governing Microparticle Morphology During Precipitation by a Compressed Antisolvent: Atomization Versus Nucleation and Growth. J. Phys. Chem. B. 2000; 104: 2725–2735
   Web of Science ®Google Scholar
• Engwicht A., Girreser U., Muller B. W. Critical Properties of Lactide-co-glycolide Polymers for the Use in Microparticle Preparation by the Aerosol Solvent Extraction System. Int. J. Pharm. 1999; 185: 61–72
   PubMed Web of Science ®Google Scholar
• Bleich J., Muller B. W. Production of Drug Loaded Microparticles by the Use of Supercritical Gases with the Aerosol Solvent Extraction System (ASES) Process. J. Microencapsulation 1996; 13: 131–139
   PubMed Web of Science ®Google Scholar
• Tom J. W., Lim G., Debenedetti P. G., Prud'homme R. K. Applications of Supercritical Fluids in the Controlled Release of Drugs. ACS Symp. Ser. 1993; 514: 238–257
   Google Scholar
• Yeo S. D., Lim G., Debenedetti P. G., Bernstein H. Formation of Microparticulate Protein Powders Using a Supercritical Fluid Antisolvent. Biotechnol. Bioeng. 1993; 41: 341–346
   PubMed Web of Science ®Google Scholar
• Hanna M., York P. Method and Apparatus for the Formation of Particles. Patent PCT/GB94/01426, 1994
   Google Scholar
• Hanna M., York P. Particle Engineering by Supercritical Fluid Technologies for Powder Inhalation Drug Delivery. Proceedings of Respiratory Drug Delivery V, Phoenix, 1996. , AZ, 231–239
   Google Scholar
• Hanna M., York P., Shekunov B. Y. Control of the Polymorphic Forms of a Drug Substance by Solution Enhanced Dispersion by Supercritical Fluids (SEDS). Proceedings of the Fifth Meeting on Supercritical Fluids. Materials and Natural Products Processing, NiceFrance, 1998. 1: 325–330
   Google Scholar
• Jaarmo S., Rantakyla M., Aaltonen O. Particle Tailoring with Supercritical Fluids: Production of Amorphous Pharmaceutical Particles. Proceedings of the Fourth International Symposium on Supercritical Fluids, SendaiJapan, 1997, 263–266
   Google Scholar
• Sassiat P. R., Mourier P., Caude M. H., Rosset R. H. Measurement of Diffusion Coefficients in Supercritical Carbon Dioxide and Correlation with the Equation of Wilke and Chang. Anal. Chem. 1987; 59: 1164–1170
   Web of Science ®Google Scholar
• Randolph T. W., Randolph A. D., Mebes M., Yeung S. Submicrometer Sized Biodegradable Particles of Poly (lactic Acid) via the Gas Antisolvent Spray Precipitation Process. Biotechnol. Prog. 1993; 9: 429–435
   PubMed Web of Science ®Google Scholar
• Mawson S., Kanakia S., Johnston K. P. Coaxial Nozzle for Control of Particle Morphology in Precipitation with a Compressed Fluid Antisolvent. J. Appl. Polym. Sci. 1997; 64: 2105–2118
   Web of Science ®Google Scholar
• Nesta D. P., Elliott J. S., Warr J. P. Supercritical Fluid Precipitation of Recombinant Human Immunoglobulin from Aqueous Solutions. Biotechnol. Bioeng. 1999; 67: 457–464
   Web of Science ®Google Scholar
• Winters M. A., Knutson B. L., Debenedetti P. G., Sparks H. G., Przybycien T. U., Stevenson C. L., Prestrelski S. J. Precipitation of Proteins in Supercritical Carbon Dioxide. J. Pharm. Sci. 1996; 85: 586–594
   PubMed Web of Science ®Google Scholar
• Hanna M., York P. Method and Apparatus for the Formation of Particles. Patent No. PCT/GB95/01523, 1995
   Google Scholar
• Sloan R., Hollowood M. E., Ashraf W., York P., Humphreys G. O. Supercritical Fluid Processing: Preparation of Stable Protein Particles. Proceedings of the Fifth Meeting on Supercritical Fluids. Materials and Natural Products Processing, NiceFrance, 1998. 1: 301–306
   Google Scholar
• Young T. J., Johnston K. P., Mishima K., Tanaka H. Encapsulation of Lysozyme in a Biodegradable Polymer by Precipitation with a Vapor-over-Liquid Antisolvent. J. Pharm. Sci. 1999; 88: 640–650
   PubMed Web of Science ®Google Scholar
• Tom J. W., Debenedetti P. G. Particle Formation with Supercritical Fluids—A Review. J. Aerosol. Sci. 1991; 22: 555–584
   Web of Science ®Google Scholar
• Philips E. M., Stella V. J. Rapid Expansion from Supercritical Solutions: Application to Pharmaceutical Processes. Int. J. Pharm. 1993; 94: 1–10
   Google Scholar
• Knutson B. L., Debenedetti P. G., Tom J. W. Microparticulate Systems for the Delivery of Proteins and Vaccines. Marcel Dekker, Inc., New York 1996; 77: 89–125
   Google Scholar
• Matson D. W., Peterson R. C., Smith R. D. Production of Fine Powders by the Rapid Expansion of Supercritical Fluid Solutions. Adv. Ceramics 1987; 21: 109
   Google Scholar
• Kim J. H., Paxton T. E., Tomasko D. L. Microencapsulation of Naproxen Using Rapid Expansion of Supercritical Solutions. Biotechnol. Prog. 1996; 12: 650–661
   Web of Science ®Google Scholar
• Knez Z., Skerget M., Sencar-Bozic P., Rizner A. Solubility of Nifedipine and Nitrendipine in Supercritical CO2. J. Chem. Eng. Data 1995; 40: 216–220
   Web of Science ®Google Scholar
• Ting S. S.T., MacNaughton S. J., Tomasko D. L., Foster N. R. Solubility of Naproxen in Supercritical Carbon Dioxide With and Without Cosolvents. Ind. Eng. Chem. Res. 1993; 32: 1471–1481
   Web of Science ®Google Scholar
• Young T. J., Mawson S., Johnston K. P., Henriksen I. B., Pace G. W., Mishra A. K. Rapid Expansion from Supercritical to Aqueous Solution to Produce Submicron Suspensions of Water-Insoluble Drugs. Biotechnol. Prog. 2000; 16: 402–407
   PubMed Web of Science ®Google Scholar
• Weidner E., Steiner R., Knez Z. Powder Generation from Polyethylene Glycols with Compressible Fluids. Process Technology Proceedings 12, High Pressure Chemical Engineering, R. R.V. Rohr, C. Trepp. Elsevier, AmsterdamNetherlands 1996; 223–228
   Google Scholar
• Srcic S., Sencar-Bozic P., Knez Z., Kerc J. Improvement of Nifedipine Dissolution Characteristics Using Supercritical CO2. Proceedings of the 16th Pharmaceutical Technology Conference and Exhibition, AthensGreece, 1997, 59–69
   Google Scholar
• Florey K., Brewer G. A. Analytical Profiles of Drug Substances. Academic Press, New York 1987
   Google Scholar
• Kiran E., Zhuang Z. Miscibility and Phase Separation of Polymers in Near- and Supercritical Fluids. ACS Symp. Ser. 1997; 670: 2–36
   Google Scholar
• Mumenthaler M., Leuenberger H. Atmospheric Spray-Freeze Drying: A Suitable Alternative in Freeze-Drying Technology. Int. J. Pharm. 1991; 72: 97–110
   Web of Science ®Google Scholar
• Oyler J. R. Liquid Substances Freeze-Drying Systems and Methods. U.S. 5208998 Patent, 1993
   Google Scholar
• Briggs A. R., Maxwell T. J. Process for Preparing Powder Blends. U.S. Patent 3721725, 1973
   Google Scholar
• Briggs A. R., Maxwell T. J. Lyophilized Biological Products. U.S. Patent 3928566, 1975
   Google Scholar
• Briggs A. R., Maxwell T. J. Method of Preparation of Lyophilized Biological Products. U.S. Patent 3932943, 1976
   Google Scholar
• Adams T. H., Beck J. P., Menson R. C. Method and Apparatus for Making Novel Particulate Compositions. U.S. Patent 4211015, 1980
   Google Scholar
• Adams T. H., Beck J. P., Menson R. C. Novel Particulate Compositions. U.S. Patent 4323478, 1982
   Google Scholar
• The Montreal Protocol on Substances that Deplete the Ozone Layer. 1987
   Google Scholar
• Williams R. O., Rogers T. L., Liu J. Study of Solubility of Steroids in Hydrofluoroalkane Propellants. Drug Dev. Ind. Pharm. 1999; 25: 1227–1234
   PubMed Web of Science ®Google Scholar
• Dunn D. B., Masavage G. J., Sauer H. A. Method of Freezing Solution Droplets and the Like Using Immiscible Refrigerants of Differing Densities. U.S. Patent 3653222, 1972
   Google Scholar
• Buxton I. R., Peach J. M. Process and Apparatus for Freezing a Liquid Medium. U.S. Patent 4470202, 1984
   Google Scholar
• Sauer H. A. Method and Apparatus for Freeze-Freeze Drying. U.S. Patent 3484946, 1969
   Google Scholar
• Lilakos L. Method and Apparatus for Cryogenic Crystallization of Fats. U.S. Patent 4952224, 1990
   Google Scholar
• Hebert P. F., Healy M. S. Production Scale Method of Forming Microparticles. U.S. Patent 5922253, 1999
   Google Scholar
• Gombotz W. R., Healy H. S., Brown L. R. Very Low Temperature Casting of Controlled Release Microspheres. U.S. Patent 5019400, 1991
   Google Scholar
• Gombotz W. R., Healy M. S., Brown L. R., Auer H. E. Process for Producing Small Particles of Biologically Active Molecules. Patent WO90/13285, 1990
   Google Scholar
• Gusman M. I., Johnson S. M. Cryochemical Method of Preparing Ultrafine Particles of High-Purity Superconducting Oxides. U.S. Patent 4975415, 1990
   Google Scholar