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(12) United States Patent (10) Patent No.: US 9,012,411 B2 Jacob (45) Date of Patent: Apr

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(12) United States Patent (10) Patent No.: US 9,012,411 B2 Jacob (45) Date of Patent: Apr USOO90 12411 B2 (12) United States Patent (10) Patent No.: US 9,012,411 B2 Jacob (45) Date of Patent: Apr. 21, 2015 (54) FORMULATIONS FROM DERIVATIVES OF 7,682,636 B2 3/2010 Babish et al. 7,736,679 B2 6/2010 Antony CURCUMIN, PACLITAXEL, AND ASPIRIN 2003/O147979 A1 8, 2003 Mae et al. 2003/O153512 A1 8/2003 Hergenhahn et al. (75) Inventor: James N. Jacob, Saunderstown, RI (US) 2005, OOO8682 A1 1/2005 Tramontana 2005, 0181036 A1 8/2005 Aggarwal et al. (73) Assignee: Organomed Corporation, Coventry, RI 2005/0208157 A1 9, 2005 Navarro et al. (US) 2005/0215487 A1* 9, 2005 Holicket al. ................... 514, 23 2005/0267221 A1 12/2005 Wellen 2006, OO67998 A1 3/2006 Kurzrock et al. (*) Notice: Subject to any disclaimer, the term of this 2006/0210656 A1 9/2006 Aggarwal patent is extended or adjusted under 35 2006/02284.03 A1 10, 2006 Zimmerman U.S.C. 154(b) by 58 days. 2007/0060644 A1 3/2007 Vander Jagt et al. 2007. O148263 A1 6/2007 Antony (21) Appl. No.: 13/537,814 2008/O193573 A1 8, 2008 Gow et al. 2009, O104294 A1 4/2009 Wenk et al. 2009/O131373 A1 5/2009 Giori et al. (22) Filed: Jun. 29, 2012 2009,0280199 A1 11/2009 Russell 2009, 0291 102 A1 11/2009 Fortin (65) Prior Publication Data 2010.0048901 A1 2/2010 Takahashi et al. US 2013/OO29922 A1 Jan. 31, 2013 2010, 0196496 A1 8, 2010 Fortin FOREIGN PATENT DOCUMENTS Related U.S. Application Data CN 1739509 A 3, 2006 (63) Continuation-in-part of application No. DE 10245.988 * 1 2005 PCT/US2010/062481, filed on Dec. 30, 2010. KR 201OOO60674. A 6, 2010 WO 86,03206 A1 6, 1986 (60) Provisional application No. 61/282,211, filed on Dec. WO WO2006 117077 * 11, 2006 31, 2009. WO 2008, 150899 A1 12/2008 (51) Int. Cl. OTHER PUBLICATIONS A6 IK3I/12 (2006.01) A6 IK3I/05 (2006.01) Sharma et al. Curcumin: The story So far. European Journal of Cancer A6 IK3I/202 (2006.01) 41:1955-1968, 2005.* Cassileth, B. “Turmeric (Curcuma longa, Curcuma domestica)” A6 IK3I/337 (2006.01) Oncology, vol. 24 No. 6 http://www.cancernetwork.com/displayfar A6 IK3I/66 (2006.01) ticle/10165/1568482 (Accessed Oct. 26, 2010). A6 IK36/9066 (2006.01) Gopalan, B. et al. “Supercritical Carbon Dioxide Extraction of Tur A6 IK3I/7034 (2006.01) meric (Curcuma longa)” J. Agric. Food Chem. 2000, 48, pp. 2189 C07C 69/157 (2006.01) 2192. CD7C 69/42 (2006.01) Kao, L. et al. “Supercritical CO2 Extraction of Turmerones From C07C 69/587 (2006.01) Turmeric and High-Pressure Phase Equilibrium of CO2 + C07C 69/92 (2006.01) turmerones' J. of Supercritical Fluids, 2007, 43, pp. 276-282. C7H I3/04 (2006.01) Kunnumakkara, A. B. etal. "Curcumin Potentiates Antitumor Activ ity of Gemcitabine in an Orthotopic Model of Pancreatic Cancer (52) U.S. Cl. Through Suppression of Proliferation, Angiogenesis, and Inhibition CPC ............. A61K 36/9066 (2013.01); A61 K3I/I2 of Nuclear Factor-Kappab-Regulated Gene Products' Cancer Res., (2013.01); A61 K3I/337 (2013.01); A61 K 2007, 67(8), pp. 3853-3861. 3 1/616 (2013.01); A61 K3I/7034 (2013.01): Saw, C. L. L. et al. “synergistic anti-Inflammatory Effects of Low C07C 69/157 (2013.01); C07C 69/42 Doses of Curcumin in Combination With Polyunsaturated Fatty (2013.01); C07C 69/587 (2013.01); C07C Acids: Docosahexaenoic Acid or Eicosapentaenoic Acid' Biochemi 69/92 (2013.01); C07H 13/04 (2013.01) cal Pharmacology, 2010, 79 (3), pp. 421-430. (58) Field of Classification Search (Continued) CPC ..... A61K 31/12: A61K31/337; C07H 13/04; C07C 69/92; C07C 69/587; CO7C 69/42 USPC ...................... 514/23, 159; 536/119; 560/194 Primary Examiner —Yong Chu See application file for complete search history. Assistant Examiner — Yih-Horng Shiao (56) References Cited (74) Attorney, Agent, or Firm — Nixon Peabody LLP U.S. PATENT DOCUMENTS (57) ABSTRACT 3.279,990 A 10, 1966 Rose et al. 3,843,626 A 10, 1974 Sutton The invention provides novel compounds and formulations of 4,242,330 A 12, 1980 Hussain et al. turmeric oil, fish oil, aspirin and anti-cancer drugs (pacli 4,906,471 A 3, 1990 Liu 5,108,750 A 4, 1992 Liu taxel) having anti-inflammatory, analgesic and/oranti-cancer 5,700,784. A 12/1997 Shinojima et al. activity. 6,218,367 B1 4/2001 Jacob .............................. 514/25 6,979,470 B2 12/2005 Babish et al. 7,205,011 B2 4/2007 Chen et al. 17 Claims, 53 Drawing Sheets US 9,012.411 B2 Page 2 (56) References Cited Jeong, S.O., "dimethoxycurcumin, a synthetic curcumin analogue, induces heme oxygenase-1 expression through Nrf2 activiation in RAW264.7 macrophages” Journal of Clinical Biochemistry and OTHER PUBLICATIONS Nutrition, Jan. 2009, vol. 44, No. 1, pp. 79-84. Turmeric. http://www.hairdye.eu/turmeric en.html (Accessed Oct. Lin, L., et al., “Antitumor agents 250. design and synthesis of new 26, 2010). curcumin analogues as potential anti-prostate cancer agents' Journal Jayaprakasha, G. K., et al., "Chemical composition of turmeric oil a of Medicinal Chemistry, Jun. 29, 2006, vol. 49, No. 13, pp. 3963 byproduct from turmeric oleoresin industry and its inhibitory activity 3972. against different fungi' Z, Naturforsch C, 2001. 01-02, vol. 56, No. 1-2, pp. 40-44. * cited by examiner U.S. Patent Apr. 21, 2015 Sheet 1 of 53 US 9,012.411 B2 Di(acetylsalicyloyl)-curcumin O. O. - -Sor rolesu-N-- --- -- OCOCH" ...,s ...sCHCOO -S-O Monoacetylsalicyloyl-curcumin a s ra's c. OCH OCH - Diacetylcurcumin O O S. s CHCOO or S. - - OCOCH OCH OCH Diglutaroyl curcumin HooculuoO sr lu s lu-coolO OCH OCH Monoglutaroyl curcumin O O 21 Hooculul,O ors rS.S1 oH OCH OCH FIG. IA U.S. Patent Apr. 21, 2015 Sheet 3 Of 53 US 9,012.411 B2 E EA6988O La 89.469-\ EN5:\\ Hww.0xxx as: ? is -\ NS O GEL't 868 -\ EN formissana Z9LZE ES O scCawalhallaxosurns 196EE, Z - ow8 naval 82 (-2/ -a--s-s 80 - E/GEG / EOEOawarf i? SEE3. — Oost-i S < score S. 3. ON COG, s s Lt.800 FOGIO N 1990 t890 199-809– N E.LL.IO i" IO- M 00001 ar T r r r r T r ror T T r -r r - r r s U.S. Patent Apr. 21, 2015 Sheet 4 of 53 US 9,012.411 B2 SN ar s -N la O9 asses O GSO 9- - F - OS -N w CN H T-T roof | -rororo rotoror T f o T-I-T -ror T -roro or -- as s r s U.S. Patent Apr. 21, 2015 Sheet 5 of 53 US 9,012.411 B2 Es 3&888 EELGI ESCO- ww. S. LOSEO SEA N its Il El N. 90Sr \ arra OG9. Evy tra w 43.4\ XXXXXXX 68 - era 39-N Sax | E; Da - as SSS es SO ::/ ex gi/ neces GE9E S// o, 962,gif ?/ Sigi-/ - see G (YS r r RN E9 it -- t GL - t8 r. O97'-- 699 (999- M Q999 - > tGOS - x: 1979 L909Eli- as asses 2 isE. so GI- OL ror - -or r ar -or r r s s e e w s U.S. Patent Apr. 21, 2015 Sheet 6 of 53 US 9,012.411 B2 2 — G9EA it. W SitEEN N EN 660-)- - 09ZEZZ / :::::// E; / E/to / wn 98 GZ-l: 97CCSSSI -------- re-art - r t s o s ww. gue U.S. Patent Apr. 21, 2015 Sheet 7 Of 53 US 9,012.411 B2 U.S. Patent Apr. 21, 2015 Sheet 8 Of 53 US 9,012.411 B2 E x LtG s s s s s s e U.S. Patent Apr. 21, 2015 Sheet 9 Of 53 US 9,012.411 B2 E Lt. ( e as e an se s e s re U.S. Patent Apr. 21, 2015 Sheet 10 Of 53 US 9,012.411 B2 FIG. 5 Group Group 2 Grop 3 Group 4 a Group 5 ri 3 60 min 90 min 8 in Intervals U.S. Patent Apr. 21, 2015 Sheet 11 of 53 US 9,012.411 B2 FIG. 6 I Group1. - Group. Group 3 S s s s 2100 AA - as s se: r? Intervals U.S. Patent Apr. 21, 2015 Sheet 12 Of 53 US 9,012.411 B2 FIG. 7 - Group H. Group 2 - Group 3 --Group ri- Group 5 "p <0.05 as compared to group 5 Interwals U.S. Patent Apr. 21, 2015 Sheet 13 Of 53 US 9,012.411 B2 *p <0.05 as compared to group 5 ck 70 64 1. O Group 4 Group 5 U.S. Patent Apr. 21, 2015 Sheet 14 of 53 US 9,012.411 B2 U.S. Patent Apr. 21, 2015 Sheet 15 Of 53 US 9,012.411 B2 FIG. 10 p30.05 as compared to grpup 11 US 1 h & 75 : 1040 U.S. Patent Apr. 21, 2015 Sheet 16 of 53 US 9,012.411 B2 FIG 11 p<0.05 as compared to group 1OO 11 86 84 8 4. O 2 O -2 O ass: U.S. Patent Apr. 21, 2015 Sheet 17 Of 53 US 9,012.411 B2 F.G. 12 pKO.05 as Compared to grip up 10; Hip-0.05 as Compared to grpup 11, p<0.05 as compared to grpup 9 U.S. Patent Apr. 21, 2015 Sheet 18 Of 53 US 9,012.411 B2 FIG.
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