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(12) United States Patent (10) Patent No.: US 9,682,043 B2 Goldman (45) Date of Patent: Jun

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(12) United States Patent (10) Patent No.: US 9,682,043 B2 Goldman (45) Date of Patent: Jun USOO9682043B2 (12) United States Patent (10) Patent No.: US 9,682,043 B2 Goldman (45) Date of Patent: Jun. 20, 2017 (54) METHOD OF PREPARATION OF MIXED FOREIGN PATENT DOCUMENTS PHASE CO-CRYSTALS WITH ACTIVE AGENTS JP 63-240936 A 10, 1988 JP 2003-522097 A 8, 1999 JP 20O2506876 A 3, 2002 (75) Inventor: David Goldman, Portland, CT (US) JP 2002356419 A 12/2002 WO WO99/47543 A2 9, 1999 (73) Assignee: MedCrystallForms, LLC, Hunt Valley, WO WO O2/O55,059 A2 T 2002 MD (US) WO WO O3/101392 A2 12/2003 WO WO 2004/043358 5, 2004 (*) Notice: Subject to any disclaimer, the term of this WO WO 2004/078161 A1 9, 2004 patent is extended or adjusted under 35 WO WO 2004/082666 9, 2004 U.S.C. 154(b) by 537 days. OTHER PUBLICATIONS (21) Appl. No.: 11/008,034 Lide CRC Handbook of Chemistry and Physics 2003 p. 3-246 and 3-480. (22) Filed: Dec. 9, 2004 Meyerson et al. “Crystals, Crystal Growth, and Nucleation' Hand book of Industrial Crystallization Ed. Meyerson. Woburn: But (65) Prior Publication Data terworth-Heinemann 2002 p. 33, and 38-39.* US 2005/0181041 A1 Aug. 18, 2005 Payne et al. International Journal of Pharmaceutics 1999 177:231 245-k Zhang et al. Journal of Pharmaceutical Sciences 2007 96(5):990 Related U.S. Application Data 995.* (60) Provisional application No. 60/528.232, filed on Dec. Reutzel-Edens et al. Solid-state pharmaceutical development: 9, 2003, provisional application No. 60/559,862, filed Ensuring stability through salt and polymorph screening. Pharma ceutical Stress Testing. Ed. Baertschi et al. New York:Informa on Apr. 6, 2004. Healthcare 2011 p. 254 and 266-267.* Drenth Principles of Protein X-ray Crystallography 1999 New (51) Int. Cl. York:Springer Science+Business Media p. 19.* A6 IK 9/14 (2006.01) International Search Report for PCT/US2004/041500 (Oct. 6, A6 IK 8/63 (2006.01) 2006). A6 IK 9/48 (2006.01) Khan et al. "Stability characterization of controlled release A6 IK 9/10 (2006.01) coprecipitates and Solid dispersions,” Journal of Controlled Release, (52) U.S. Cl. Elsevier Science Publishers B.V., vol. 63, No. 1-2, Jan. 2000. Japanese Patent Office, Office Action in connection with Japanese CPC ................ A61K 9/145 (2013.01); A61K 8/63 Patent Application No. 1495.02/2011 (May 7, 2013). (2013.01); A61K 9/146 (2013.01); A61K 9/148 Japanese Patent Office, Office Action in connection with Japanese (2013.01); A61 K 9/10 (2013.01); A61 K9/4858 Patent Application No. 182177/2014 (May 24, 2016). (2013.01) Japanese Patent Office, Office Action in connection with Japanese (58) Field of Classification Search Patent Application No. 182177/2014 (Aug. 18, 2015). None See application file for complete search history. * cited by examiner (56) References Cited Primary Examiner — Robert A Wax Assistant Examiner — Caralynne Helm U.S. PATENT DOCUMENTS (74) Attorney, Agent, or Firm — Leydig, Voit & Mayer, 4,384,980 A 5, 1983 Patel et al. Ltd. 4,606.909 A * 8/1986 Bechgaard et al. .......... 424/469 5,118,528 A 6, 1992 Fessi et al. (57) ABSTRACT 5,266,712 A * 11/1993 Lanquetin ..................... 552,574 5,665,331 A 9/1997 Bagchi et al. This invention pertains to a method of preparing mixed 2002/0142049 A1 * 10, 2002 Lee ............................... 424/499 phase co-crystals of active agents with one or more materials 2003/0003155 A1* 1/2003 Kipp et al..................... 424/489 that allows the modification of the active agent to a new 2003/0031721 A1 2/2003 Bogue physical/crystal form with unique properties useful for the 2003/0049323 A1 3f2003 Hitt et al. ..................... 424/489 2003.0068384 A1 4/2003 Brocchini et al. delivery of the active agent, as well as compositions com 2003/0077297 A1* 4, 2003 Chen et al. ................... 424/400 prising the mixed phase co-crystals. 2003/0077329 A1 * 4/2003 Kipp et al..................... 424/489 2003. O166509 A1 9, 2003 Edwards et al. 1 Claim, 8 Drawing Sheets U.S. Patent Jun. 20, 2017 Sheet 1 of 8 US 9,682,043 B2 0.0 FIG. 1 a -0. 2 214.70°C S 206.98°C ss -0.4 142.0J/g 5l a -0.6 C -0.8 -1.0 w y-ll- r -------- 40 90 140 190 240 290 Temperture (C) O.O G. 1b 53.76°C 0.2 50.75°C G 51.18J/g s 2O2.23°C s -0.4 2.9 -0.6 -O.8 35 85 135 185 235 285 Temperture (C) U.S. Patent Jun. 20, 2017 Sheet 2 of 8 US 9,682,043 B2 d v """ d c C cy N als s Y s s D CN d cN w C v --- d Cd d o cy Cd ad & N w -- r (SunOO)/AISueu s U.S. Patent Jun. 20, 2017 Sheet 3 of 8 US 9,682,043 B2 SCNoic 2 9 o o 3 s ver (SunOO)/AISueu U.S. Patent Jun. 20, 2017 Sheet 4 of 8 US 9,682,043 B2 S. 9 S N 2 9 o s . o (SunOO)/AISueu U.S. Patent Jun. 20, 2017 Sheet S of 8 US 9,682,043 B2 9 9 g g s g g arra ara 8 o Yea Ya s w C C C C cN CN s s 2 2 CVS O CY) co ed - --- ar o f f 3 3 S S 5 5 S 8 (SunOO)/AISueu (SunOO)/AISueu U.S. Patent Jun. 20, 2017 Sheet 6 of 8 US 9,682,043 B2 g 09 U.S. Patent Jun. 20, 2017 Sheet 7 of 8 US 9,682,043 B2 09 00"| (uffin) 'ouoo U.S. Patent Jun. 20, 2017 Sheet 8 of 8 US 9,682,043 B2 peNIOSSIO % US 9,682,043 B2 1. 2 METHOD OF PREPARATION OF MIXED phase co-crystals enable, and lack the multi-functional PHASE CO-CRYSTALS WITH ACTIVE aspects that mixed phase co-crystals offer with respect to AGENTS improved drug delivery. Co-crystallization of chemically related materials is illus CROSS-REFERENCE TO RELATED PATENT 5 trated by the preparation of co-crystallized sugars (U.S. Pat. APPLICATIONS Nos. 4,101,680 and 4.338,339), of acetylenic compounds (U.S. Pat. No. 4,384,980), and sugar alcohols (U.S. Pat. Nos. This patent application claims the benefit of U.S. Provi 5,679,398; 5,958,471 and 6,083,438). The simple co-crys sional Patent Application No. 60/559,862, filed Apr. 6, 2004 tals therein described do not have the broad utility that and U.S. Provisional Patent Application No. 60/528.232, 10 mixed phase co-crystals have for the enhancement of prop filed Dec. 9, 2003, which are incorporated by reference erties of widely different structures and physico-chemical herein. properties. Incorporation of minor components by a process FIELD OF THE INVENTION described as co-crystallization that yields a product of 15 indeterminate crystalline structure is illustrated by U.S. Pat. This invention pertains to methods of preparing an active Nos. 6,376,481, and 6,267.963 (sterol esters); U.S. Pat. No. agent as mixed phase co-crystals that have unique physical 6.214,402 (dilution of sweetener); U.S. Pat. No. 4,751,294 properties that differ from the active agent in pure form, as (stabilization by a base); U.S. Pat. No. 5,910.523 (nanocom well as compositions comprising mixed phase co-crystals. posites); U.S. Pat. No. 5,876,506 (mesomorphic sugar), U.S. The formulated mixed phase co-crystals are heterogenous Pat. No. 5,075,291 (uniform dispersion of drug in sugar and contain crystalline regions within the particles/granules alcohol); and U.S. Pat. No. 5,451,416. These materials of produced. Mixed phase co-crystals are useful for systemic indeterminate structure lack the ability of mixed phase delivery of the active agent as human and animal pharma co-crystals to maintain primary crystalline characteristics of ceuticals, dietary Supplements, and agrochemicals. Further the active agent while imparting amorphous-like properties more, mixed phase co-crystals have utility in imparting 25 along with designed functionalities to enhance solubility, desirable physical and stability properties otherwise not dissolution, and absorption. achievable for the pure active agent or in combination as a Complex mixtures of crystalline materials formed by simple formulation with the materials incorporated with the melt/congealing process are described in U.S. Pat. No. active agent. 6.267.963 (sterol-emulsion complexes); U.S. Pat. Nos. 30 4.855,326 and 5,853.762 (rapidly dissolving dosage unit); BACKGROUND OF THE INVENTION and U.S. Pat. No. 5,075,291. The process for preparing co-crystals by evaporation or cooling from a solvent system Co-crystals occur in nature and form spontaneously with is described in U.S. Pat. No. 4,145,214 (photoconductors); closely related chemical structures, such as chemical iso U.S. Pat. Nos. 4,751.294; 4,971,797; and 6,214,402. Appli mers (racemates, diasteriomers, and the like). Co-crystals 35 cations for which no active agent is incorporated are are also found for materials that complex together in Solu described in U.S. Pat. Nos. 4,145,214 and 4,384,980. These tion Such as protein-ligands, chelates, inclusion complexes materials of indeterminate structure lack the ability of mixed as with cyclodextrins, and ligands. In U.S. Pat. Nos. 4,971, phase co-crystals to maintain primary crystalline character 797; 6,312,723 and 6.312,712, complexes of cyclodextrin istics of the active agent while imparting amorphous-like and active agents are described as being co-crystallized 40 properties along with designed functionalities to enhance together from solution.
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