United States Patent (10) Patent No.: US 9,687,573 B2 Reb Et Al

United States Patent (10) Patent No.: US 9,687,573 B2 Reb Et Al

US009687573B2 (12) United States Patent (10) Patent No.: US 9,687,573 B2 Reb et al. (45) Date of Patent: Jun. 27, 2017 (54) COMPOSITIONS AND ASSOCIATED 5,762.903. A 6/1998 Parket al. METHODS FOR RADIOSOTOPE-BINDING 3. A 3. E. et al. e MCROPARTICLES 5,885,547 A 3/1999 Gray 5,888,546 A 3, 1999 Ji et al. (71) Applicant: Biosphere Medical, Inc., South Jordan, 5,894,022 A 4/1999 Ji et al. UT (US) 5,942,209 A 8, 1999 Leavitt et al. 6,015,541 A 1/2000 Greff et al. (72) Inventors: Philippe Reb, Themericourt (FR): 6,039,970 A 3/2000 Callegaro et al. Celine Chaix, Clichy la Garenne (FR) 6,060,040 A * 5/2000 Tournier ................ A61K424/9.364 49,06 6,083,495 A 7/2000 Holmes-Farley et al. (73) Assignee: Biosphere Medical, Inc., South Jordan, 6,099.457 A 8, 2000 Good UT (US) 6,103,295 A 8, 2000 Chan et al. 6,106,454. A 8/2000 Berg et al. (*) Notice: Subject to any disclaimer, the term of this 6,168,777 B1 1/2001 Greff et al. patent is extended or adjusted under 35 4.2.95. r. I R $39. St.reff et al. U.S.C. 154(b) by 0 days. 6,231,615 B1 5/2001 Preissman 6,241,962 B1 6/2001 Nicolini (21) Appl. No.: 14/207,219 6.248,057 B1 6/2001 Mavity et al. 6,258.338 B1 7/2001 Gray (22) Filed: Mar 12, 2014 6,273,851 B1 8, 2001 Slater et al. 9 6,296,831 B1 10/2001 Weller et al. (65) Prior Publication Data (Continued) US 2014/0271461 A1 Sep. 18, 2014 FOREIGN PATENT DOCUMENTS CA 2307190 5, 1999 Related U.S. Application Data CA 230719.1 5, 1999 (60) Provisional application No. 61/779,712, filed on Mar. (Continued) 13, 2013. OTHER PUBLICATIONS (51) Int. C. A6 IK 5L/12 (2006.01) O'Leary, 2000, Periodic Table Groups http://www.ucc.ie/academic? A6 IK 5/06 (2006.01) chem dolchem/html/elem?group.html, 1-6. (52) U.S. C. Scranton et al., BioMedical Applications of Polyelectrolykes'. Adv. CPC ..... A61K 51/1244 (2013.01); Y10T 428/2982 Polymer. Sci., 1995, 122, 1-54. DeMar et al., “Comparison of Gas Clearance and Radioactive (2015.01) Microspheres for Pancreatic Blood Flow Measurement. Pancreas, (58) Field of Classification Search vol. 4, No. 2, pp. 161-168, 1989. CPC ....... A61K 49/00; A61K 51/065; A61K 51/12 Ehrhardt et al., “Therapeutic Use of 90Y Microspheres'. Nucl. Med. USPC ............................. 424/1.11, 1.29, 1.37, 9.34 Biol., vol. 14, No. 3, pp. 233-242, 1987. See application file for complete search history. Ercan, Radioactive Microparticles, Part I: Preparation. MML Series, vol. 2, pp. 283-307, 1999. (56) References Cited Ercan, Radioactive Microparticles, Part II: Medical Applications'. U.S. PATENT DOCUMENTS MML Series, vol. 2, pp. 313-342, 1999. (Continued) 3,334,050 A 8, 1967 Grothenhuis et al. 4,123,396 A 10, 1978 Rembaum et al. 4,224,177 A 9, 1980 Macedo et al. Primary Examiner — Jake Vu 4,224427 A 9, 1980 Mueller et al. Assistant Examiner — Jagadishwar Samala 4,789,501 A 12/1988 Day et al. (74) Attorney, Agent, or Firm — Stoel Rives LLP 4,889,707 A 12/1989 Day et al. 4,994,013 A 2, 1991 Suthanthiran et al. 5,011,677 A 4/1991 Day et al. (57) ABSTRACT 5,011,797 A 4/1991 Day et al. 5,030, 195 A 7, 1991 Nardi The present disclosure relates to polymeric materials that 5,039,326 A 8/1991 Day et al. may be labeled with a radioisotope, to processes for pro 5,069,816 A 12/1991 DeSantis et al. ducing the labeled polymeric material, and to methods of 5,162,267 A 11/1992 Smyth 5,163,896 A 1 1/1992 Suthanthiran et al. using the materials in analytical and therapeutic applica 5, 182,051 A 1/1993 Bandy et al. tions. Specifically, the disclosure relates to injectable and 5,302.369 A 4/1994 Day et al. implantable microparticles, such as microspheres, which are 5,342,283 A 8, 1994 Good 5,424,288 A 6, 1995 Order associated with radioisotopes such that the microparticles 5,496,545 A 3/1996 Holmes-Farley et al. are both therapeutic and detectable. The radioisotope-con 5,514,379 A 5, 1996 Weissleder et al. 5,614,652 A 3, 1997 Filler et al. taining microparticles are useful for embolization and other 5,635,215 A 6, 1997 Boschetti et al. therapeutic medical applications. 5,648,100 A 7, 1997 Boschetti et al. 5,667,775 A 9/1997 Holmes-Farley et al. 16 Claims, 11 Drawing Sheets US 9,687,573 B2 Page 2 (56) References Cited Schafer et al., “Physical and Chemical Characterization of a Porous Phosphate-Modified Zirconia Substrate'. Journal of Chromatogra U.S. PATENT DOCUMENTS phy, 587(2): 137-147, Dec. 20, 1991. International Search Report dated May 16, 2007 for PCT/US2005/ 6,328,700 B1 12/2001 Rheinhardt O25.645. 6,333,020 B1 12/2001 Wallace et al. van Es et al., Tumour Embolization of the Vx2 Rabbit Head and 6,335,028 B1 1/2002 Vogel et al. Neck Cancer Model with Dextran Hydrogel and Holmium-Poly 6,348,184 B1 2/2002 Nicolini (L-Lactic Acid) Microspheres: A Radionuclide and Histological 6,352,682 B2 3, 2002 Leavitt et al. Pilot Study, Journal of Cranio-Maxillogacial Surgery, Oct. 2001, 6,355,275 B1 3, 2002 Klein 29, p. 289-297. 6,368,586 B1 4/2002 Jacob et al. Business Wire, Biosphere Medical Launches New EmboGold 6,379,648 B1 4/2002 Day et al. Microspheres'. Sep. 6, 2001. 6,436,424 B1 8/2002 Vogel et al. Notice of Abandonment dated Mar. 30, 2009 for U.S. Appl. No. 6,589,502 B1 7/2003 Coniglione et al. 10/688,768. 6,660,301 B1 12/2003 Vogel et al. Office Action dated Sep. 8, 2008 for U.S. Appl. No. 10/688,768. 6,680,046 B1 1/2004 Boschetti Office Action dated Jul. 27, 2007 for U.S. Appl. No. 10/688,768. 6,746,661 B2 6/2004 Kaplan Office Action dated Dec. 19, 2006 for U.S. Appl. No. 10/688,768. 6,818, 199 B1 1 1/2004 Hainfeld et al. Office Action dated Nov. 12, 2008 for U.S. Appl. No. 1 1/185.449. 2002fOO68089 A1 6/2002 Vogel et al. Office Action dated Aug. 11, 2009 for U.S. Appl. No. 1 1/185.449. 2002/0114763 A1 8/2002 Glajch et al. Office Action dated Apr. 9, 2010 for U.S. Appl. No. 11/185.449. 2002fO187172 A1* 12, 2002 Reb ........................ A61K 49.18 Office Action dated Sep. 27, 2010 for U.S. Appl. No. 1 1/185.449. 424/401 Office Action dated Aug. 9, 2011 for U.S. Appl. No. 11/185.449. 2002fO197326 A1 12/2002 Vogel et al. Mumper et al., Neutron-Activated Holmium-166-Poly (L-Lactic 2003/0118658 A1 6/2003 Trogolo et al. Lactic Acid) Microspheres: A Potential Agent for the Internal 2003/O120355 A1* 6/2003 Hafeli ................ A61K 51.1251 Radiation Therapy of Hepatic Tumors. Journal of Neclear Medi TOOf1 cine, vol. 32 No. 11, Nov. 1991, (Nov. 1991), pp. 2139-2143. 2003/0215519 A1 11/2003 Schwarz et al. Hafeli et al., Hepatic Tumor Radioembolization in a Rat Model 2004/0091425 A1 5, 2004 Boschetti Using Radioactive Themium (186RE/188RE) Glass Microspheres'. 2004/0258614 A1* 12/2004 Line ..................... A61K 51,065 Int. J. Radiation Oncology Biol. Phys., vol. 44, No. 1, Apr. 1999 424/1.11 (Apr. 1999), pp. 189-199. 2006/0067883 A1 3f2006 Krom ................. A61K 51.1255 Campbell et al., Tumour Dosimetry in Human Liver Following 424,129 Hepatic Yttrium-90 Microsphere Therapy, Phys. Med. Biol. 46: 487-498, 2001. FOREIGN PATENT DOCUMENTS Campbell et al., “Analysis of the Distribution of Intra-Arterial Microspheres in Human Liver Following Hepatic Yttrium-90 CA 2369983 11, 2000 Microsphere Therapy, Phys. Med. Biol. 45:1023-1033, 2000. CA 2370,124 11 2000 Ho et al., Intrahepatic 90 Y-Microspheres for Hepatocellular Car CA 2393539 6, 2001 cinoma, The Journal of Nuclear Medicine 42(10): 1587-1588, Oct. EP 1371365 12/2003 2001. WO WOOOf 661.83 11 2000 WO WOO2.34300 5, 2002 Lin et al., “Effects of 90Y-Microspheres on Liver Tumors: compari WO WOO3,OO4930 11/2003 Son of Intratumoral Injection Method and Intra-Arterial Injection WO WO2004/04O972 5, 2004 Method. The Journal of Nuclear Medicine 41(11): 1892-1897, Nov. WO WO2005/035.005 4/2005 2000. WO WO2005/061009 7/2005 Loehman, Preparation and Properties of Yttrium-Silicon-Alumi WO 2006036269 4/2006 num. Oxynitride Glasses'. The Journal of the American Ceramic WO 2008034911 3, 2008 Society 62(9-10): 491-494, 1979. Stubbs et al., 'Selective Internal Radiation Therapy with 90Yttrium Microspheres for Extensive Colorectal Liver Metastases, J. OTHER PUBLICATIONS Gastrointest. Surg. 5(3): 294.302, 2001. Stubbs et al., 'Selective Internal Radiation Therapy (SIRT) with Gray et al., “Randomised Trial of SIR-Spheres(R Plus Chemo 90Yttrium Microspheres for Extensive Colorectal Liver Metasta therapy vs. Chemotherapy Alone for Treating Patients with Liver ses'. Hepato-Gastroenterology 48: 333-337, 2001. Metastases from Primary Large Bowel Cancer. Annals of Oncol Notice of Abandonment dated Sep. 27, 2007 for U.S. Appl. No. ogy, vol. 12, pp. 1711-1720, 2001.

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