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(12) United States Patent (10) Patent No.: US 6,596,206 B2 Lee (45) Date of Patent: *Jul USOO6596206B2 (12) United States Patent (10) Patent No.: US 6,596,206 B2 Lee (45) Date of Patent: *Jul. 22, 2003 (54) GENERATION OF PHARMACEUTICAL FOREIGN PATENT DOCUMENTS AENESSING FOCUSED WO WO OO/37169O542314 6/20007/1998 (75) Inventor: partson-Hui Lee, Mountain View, W W s: 2: OTHER PUBLICATIONS (73) Assignee: Picoliter Inc., Sunnyvale, CA (US) Debenedetti et al. (1993), “Application of Supercritical Fluids for the Production of Sustained Delivery Devices.” (*) Notice: Subject to any disclaimer, the term of this Journal of Controlled Release 24:27–44. patent is extended or adjusted under 35 Tom et al. (1991), “Formation of Bioerodible Polymeric U.S.C. 154(b) by 14 days. Microspheres and Microparticles by Rapid Expansion of Supercritical Solutions,” Biotechnol. Prog. 7(5):403-411. This patent is Subject to a terminal dis- Chattopadhyay et al. (2001), “Production of Griseofulvin claimer. Nanoparticles Using Supercritical CO2 Antisolvent with Enhanced Mass Transfer.” International Journal of Phar (21) Appl. No.: 09/823,899 maceutics 228:19-31. (22) Filed: Mar 30, 2001 Jung et al. (2001), “Particle Design Using Supercritical e a Vs Fluids: Literature and Patent Survey,” Journal of Supercriti (65) Prior Publication Data cal Fluids 20:179-219. Primary Examiner Mary Lynn Theisen US 2002/0142049 A1 Oct. 3, 2002 (74) Attorney, Agent, or Firm-Dianne E. Reed; Reed & (51) Int. Cl." .................................................. B29C 9/00 Eberle LLP (52) U.S. Cl. ....................... 264/9; 264/5; 2647. (57) ABSTRACT (58) Field of Search ......................... 264/9, 7, 5; 425/6, A method and device for generating pharmaceutical agent 425/10 particles using focused acoustic energy are provided. A Solution of the pharmaceutical agent is provided in a Solvent, (56) References Cited which may be an aqueous fluid, a nonaqueous fluid, or a Supercritical fluid. Focused acoustic energy is used to eject U.S. PATENT DOCUMENTS a droplet of the solution, which is then directed into or 4,308,547 A 12/1981 Lovelady et al. ....... 346/140 R through an antisolvent that upon admixture with the Solution 5,041,849 A 8/1991 Ouate et al. ............ 346/140 R droplet causes the pharmaceutical agent in the droplet to 5,874,029 A 2/1999 Subramaniam et al. ....... 264/12 precipitate. In a preferred embodiment, the Solvent is an 2002/OOOO681 A1 1/2002 Gupta et al. ................... 264/9 aqueous or organic liquid, and the antisolvent is a Super 2002/0073989 A1 6/2002 Hadimioglu ........... 128/200.14 critical fluid. 2002/0073990 A1 6/2002 Noolandi et al. ...... 128/200.16 2002/0077369 A1 6/2002 Noolandi et al. ........... 514/958 109 Claims, 1 Drawing Sheet U.S. Patent Jul. 22, 2003 US 6,596,206 B2 US 6,596.206 B2 1 2 GENERATION OF PHARMACEUTICAL Supercritical fluid technology has Solved Some of these AGENT PARTICLES USING FOCUSED problems. One method for using this relatively new tech ACOUSTIC ENERGY nology is called the rapid expansion of Supercritical Solu tions or “RESS" method. See Tom et al. (1991) Biotechnol. s Prog. 7(5):403-411. In the RESS method, the solute of TECHNICAL FIELD interest, e.g., a pharmaceutical agent, is first Solubilized in a This invention relates generally to the generation of Supercritical fluid, i.e., a fluid at a temperature and preSSure pharmaceutical agent particles, and more particularly relates greater than its critical temperature (T) and critical pressure to the use of focused acoustic energy in generating Solid (P) Generally, the Supercritical fluid is carbon dioxide, particles comprised of a pharmaceutical agent. although other fluids are available. The solution is then BACKGROUND rapidly passed through a nozzle that is connected to a relatively low-pressure medium. The Sudden depressuriza Rapid and efficient production of particles, particularly tion of the Solution as it passes into the relatively low Small and/or Substantially uniform particles, is needed in a preSSure medium causes the Supercritical fluid to expand, variety of industries. Among other advantages, Small, Sub i.e., the density of the Supercritical fluid decreases, reducing Stantially uniform particles possess favorable flow charac 15 the ability of the Supercritical fluid to solubilize the thera teristics and exhibit little variation in interparticle behavior. peutic agent. As a direct consequence of the reduced In the pharmaceutical industry, for example, the particle size Solubility, a SuperSaturated Solution develops, which, in turn, of a therapeutic agent can affect the dissolution rate, bio causes the Solute agent to precipitate or crystallize out in availability and overall stability of the agent in a formula very Small particles. tion. Precise control of the particle Size of therapeutic agents A variation of this idea is to prepare a Solution of a is particularly important for Sustained release applications, therapeutic drug in a conventional Solvent, and then Spray where the rate of drug release is related to the Size of a the Solution through a nozzle into a Supercritical fluid that particle containing the drug. In addition, pulmonary delivery acts as an anti-Solvent. When the two fluids make contact, a of a therapeutic agent requires specifically sized particles, rapid Volume expansion occurs, reducing Solvent density generally on the order of about 1 um to about 7 lum. Particles 25 and Solvent capacity, in turn increasing SuperSaturation, that are too large may be deposited within the throat, while Solute nucleation and particle formulation. This method is particles that are too small will be exhaled. Thus, the ability commonly referred to as gas anti-Solvent recrystallization or to produce Small, uniform particles of a therapeutic agent is “GAS.” See, for example, Debenedetti et al. (1993) J. critically important in the development of particulate phar Control. Release 24:27-44 and PCT WOOO/37169 to Mer maceutical products. rifield. This proceSS has been applied to various proteins to Various approaches for attaining Small and uniform par produce particle sizes of about 5 um. See European Patent ticles have been used. Conventional comminution No. O 542 314. techniques, e.g., crushing, grinding and milling, rely on Although use of Supercritical fluid technology offers the mechanical forces to break apart relatively large particles capability of producing relatively Small particles of uniform into Smaller particles. Air-jet mills and other mills, available 35 size, it is not without drawbacks. One problem associated from, for example, DT Industries, Bristol, Pa., under the with these Supercritical methods is the reliance on nozzles tradename STOKES(R), are commonly used by the pharma and tubes for delivering the solutions. Nozzles are known to ceutical industry to decrease the particle Size of a bulk wear down over time, altering the geometry of the equip therapeutic agent into a range Suitable for pharmaceutical ment and affecting the size of the droplets formed. In applications. One drawback to Such mechanical comminu 40 addition, nozzles may become blocked during use, when, for tion techniques, however, is that Some therapeutic agents, example, particles agglomerate upon rapid expansion within particularly proteins and other therapeutic biomolecules, are the nozzle bore. In addition, nozzles and associated compo damaged during the process. Another drawback of mechani nents require cleaning and may contaminate Solutions when cal comminution is the wide distribution of particle sizes not properly maintained. produced by these techniques. Among other problems, large 45 Furthermore, the droplet sizes of the solutions (both variations in the size of particles limit the ability to produce Supercritical and conventional Solutions) produced by meth Sustained-release formulations and waste large amounts of ods relying on nozzles are relatively varied. As a result there therapeutic agents intended, for example, for inhalation. will be a large variance of the Surface tension between Although Sieving a comminuted therapeutic agent through droplets of different sizes. At the sizes required for Super an appropriate mesh Screen provides a more narrow particle 50 critical methods, the differences in Surface tension between Size distribution, large quantities of particles not having the droplets causes large variations in crystallization kinetics desired size are wasted and the potential for contamination and growth. These differences result in differently sized is increased, as the therapeutic agent must contact additional particles. Although U.S. Pat. No. 5,874,029 to Subramaniam Surfaces. et al. discusses methods for producing Small-sized droplets Other techniques for producing pharmaceutical particles 55 using nozzles, the methods still suffer from the inability to include conventional recrystallization methods. In Such effectively and consistently produce droplets of uniform methods, the therapeutic agent is initially dissolved in a SZC. Suitable Solvent. In one approach, the temperature of the Thus, there is a need in the art for an improved particle Solution is changed So that the Solubility of the Solute is formation technique wherein particle formation is highly decreased. In another approach, a Second Solvent, an 60 reproducible, controllable and predictable, and Substantially “antisolvent,” is added so that the solubility of the solute is uniform particle size can be achieved. An ideal method decreased. In both approaches, the Solute precipitates or would minimize or eliminate contact of the particle-forming crystallizes out
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