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(12) Patent Application Publication (10) Pub. No.: US 2011/0033525 A1 Liu (43) Pub US 2011 0033525A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0033525 A1 Liu (43) Pub. Date: Feb. 10, 2011 (54) DITERPENE GLYCOSIDES AS NATURAL A63L/05 (2006.01) SOLUBLIZERS A6II 3L/22 (2006.01) A6II 3/343 (2006.01) (76) Inventor: Zhijun Liu, Baton Rouge, LA (US) A63L/436 (2006.01) A638/3 (2006.01) Correspondence Address: A63L/366 (2006.01) PATENT DEPARTMENT A63L/352 (2006.01) TAYLOR, PORTER, BROOKS & PHILLIPS, A6II 35/60 (2006.01) LLP A63/496 (2006.01) P.O. BOX 2471 A63L/45 (2006.01) BATON ROUGE, LA 70821-2471 (US) B82Y5/00 (2011.01) (52) U.S. Cl. ......... 424/450; 514/777: 514/449; 514/283; (21) Appl. No.: 12/937,055 514/627: 514/568: 514/27: 514/679; 514/458: 514f731: 514f678; 424/94.1 : 514/468: 514/29: (22)22) PCT Fled:1. Apr.pr. 13,15, 2009 514/31; 514/291;s 514/20.5:s 514/450,s 514/463:s s 977/773;977/915 S371 (c)(1), 57 ABSTRACT (2), (4) Date: Oct. 8, 2010 (57) Several diterpene glycosides (e.g., rubusoside, rebaudioside, Related U.S. Application Data Steviol monoside and Stevioside) were discovered to enhance (60) Provisional application No. 61/044,176, filed on Apr. thenally solubility important of acompounds, number of pharmaceuticallyincluding but not and limited medici to, 11, 2008, provisional application No. 61/099,823, paclitaxel, camptothecin, curcumin, tanshinone HA, capsai filed on Sep. 24, 2008. cin, cyclosporine, erythromycin, nystatin, itraconazole, and O O celecoxib. The use of the diterpene glycoside rubusoside Publication Classification increased solubility in all tested compounds. The diterpene (51) Int. Cl. glycosides are a naturally occurring class of water solubility A 6LX 9/27 (2006.01) enhancing compounds that are non-toxic and that will be A6 IK 47/26 (2006.01) useful as new complexing agents or excipients in the phar A6 IK3I/337 (2006.01) maceutical, agricultural (e.g., Solubilizing pesticides), cos A6 IK 3/4375 (2006.01) metic and food industries. Aqueous solutions by using rubu A6 IK3I/I65 (2006.01) soside to increase the solubility of otherwise insoluble drugs A6 IK3I/92 (2006.01) will have several new routes of administration. In addition, A6 IK3I/7048 (2006.01) aqueous solutions of therapeutic compounds with rubusoside A6 IK 3L/2 (2006.01) were shown to retain the known pharmacological activity of A 6LX 3L/355 (2006.01) the compounds. OH Gallic acid 170 Gallotannin Patent Application Publication Feb. 10, 2011 Sheet 1 of 23 US 2011/0033525 A1 999u?UunºunO Patent Application Publication Feb. 10, 2011 Sheet 2 of 23 US 2011/0033525 A1 HI‘61-I L IL’61-I | Patent Application Publication Feb. 10, 2011 Sheet 3 of 23 US 2011/0033525 A1 O H?O Hõ? WIL’61-I HOºp|OJOWN?uÐÁIod XII,’61-I SOº, ºHOOOOºH Patent Application Publication Feb. 10, 2011 Sheet 4 of 23 US 2011/0033525 A1 HO OL‘61-I >|-61-I HOO || Patent Application Publication Feb. 10, 2011 Sheet 5 of 23 US 2011/0033525 A1 LI‘61-I AL‘61-I O SI‘61-I Patent Application Publication Feb. 10, 2011 Sheet 6 of 23 US 2011/0033525 A1 OH OH OH HO OH OH Fig. 2 Patent Application Publication Feb. 10, 2011 Sheet 7 of 23 US 2011/0033525 A1 OH OH HO OH Fig. 3 Patent Application Publication Feb. 10, 2011 Sheet 8 of 23 US 2011/0033525 A1 HO OH Fig. 4 Patent Application Publication Feb. 10, 2011 Sheet 9 of 23 US 2011/0033525 A1 OH OH HO OH bH Steviomonoside OH OII Paniculoside IV OH OH HO CH-O OH "OH Suavioside A Suavioside B OH Suavioside C, OH OH OH O H O N I HC C OH Suavioside E OH HO IO Suavioside D, HO Suavioside D, OH OH OH OH OH OH OH O OH OI HO I HO OH OH I C=O OH Suavioside G OH Suavioside H Suavioside F HO HO OH OH OH OH OII H) OI HO Suavioside OH SuavioSide J OH HO OII Patent Application Publication Feb. 10, 2011 Sheet 10 of 23 US 2011/0033525 A1 O O O N O-7 O cy N 3 o C O O ca C 3 C O SP L N OC g T 5 Y-O 2 O III S. O O T III 8 O-O O Y-O O O C C O 9. O O O bS I O O r P N 2 CD O O O O w C N 5 c)I- III co 9 O 3 CD C 9 III. 3 O-O C CD O Y-O 1 O O C : O Patent Application Publication Feb. 10, 2011 Sheet 11 of 23 US 2011/0033525 A1 0'07 W Patent Application Publication Feb. 10, 2011 Sheet 12 of 23 US 2011/0033525 A1 O O v S s v O o v v O LO O is S 9 X - v s O N c\ O O O O v C O O O O O O O O O O O CO N. CO O s CY) CN r SIleo |OJ)uOOJO UAOJ6 JOlueOued Patent Application Publication Feb. 10, 2011 Sheet 13 of 23 US 2011/0033525 A1 O O O r O X - 5 S O H.X S.O) O)S. SR SR O O O CC < n n- O S on 3. O S C in E CD CD C O O O O O O O O O O CO CO r CN v uMOJ6 ||eo |OJuOOJOlueoel Patent Application Publication Feb. 10, 2011 Sheet 14 of 23 US 2011/0033525 A1 Patent Application Publication US 2011/0033525 A1 |||-61-I CO f W Patent Application Publication Feb. 10, 2011 Sheet 16 of 23 US 2011/0033525 A1 ZL‘61-I W Patent Application Publication Feb. 10, 2011 Sheet 17 of 23 US 2011/0033525 A1 Sg5 s W Patent Application Publication Feb. 10, 2011 Sheet 18 of 23 US 2011/0033525 A1 |\ 1(|) ? |\, y],'61-I ? x|,?|| W Patent Application Publication Feb. 10, 2011 Sheet 19 of 23 US 2011/0033525 A1 W Patent Application Publication Feb. 10, 2011 Sheet 20 of 23 US 2011/0033525 A1 00°02 |OJOdOld 9|-61-I W Patent Application Publication Feb. 10, 2011 Sheet 21 of 23 US 2011/0033525 A1 3 S.g 34: ce ------ W Patent Application Publication Feb. 10, 2011 Sheet 22 of 23 US 2011/0033525 A1 O969 8|-61-I (C&126 W Patent Application Publication Feb. 10, 2011 Sheet 23 of 23 US 2011/0033525 A1 80 W US 2011/0033525 A1 Feb. 10, 2011 DITERPENE GLYCOSDES AS NATURAL ing or reducing these limitations are needed for the formula SOLUBLIZERS tions of pharmaceutical, cosmetic, agricultural chemicals, and foods products. 0004 Diterpenes. Taxanes are diterpenes produced by the 0001 (In countries other than the United States:) The ben plants of the genus Taxus (yews) such as the Pacific Yew efit of the 11 Apr. 2008 filing date of U.S. provisional patent (Taxus brevifolia) in the family of Taxaceae. Taxanes include application 61/044,176 and the benefit of the 24 Sep. 2008 paclitaxel and docetaxel. Paclitaxel is the anti-cancer drug filing date of Unites States provisional patent application under the drug name of TAXOL(R) and docetaxel is used under 61/099,823 are claimed under applicable treaties and conven the name of TAXOTERE(R) (Medicinal Natural Products. A tions. (In the United States:) The benefit of the 11 Apr. 2008 Biosynthetic Approach, 1997, John Wiley & Sons, Chiches filing date of U.S. provisional patent application 61/044, 176 ter, England; pp 186-188). Paclitaxel is a known anti-cancer and the benefit of the 24 Sep. 2008 filing date of Unites States diterpenoid alkaloid and is not soluble in water. The structure provisional patent application 61/099,823 are claimed under of paclitaxel is shown in FIG. 1H. Therapeutic solutions of 35 U.S.C. S 119(e) in the United States. paclitaxel currently contain either an oil or dehydrated alco hol or both; or paclitaxel is bound to albumin. None of these TECHNICAL FIELD formulations are true water solutions. Other taxanes include baccatin III, 10-deacetylbaccatin III, cephalomannine, and 0002 This invention pertains to new uses for diterpene 10-deacetylcephalomannine. These taxanes are characterized glycosides as non-toxic, natural solubilizers for use in pre with a four-membered oxetane ring and a complex ester side paring aqueous Solutions of various drugs, agricultural chain in their structures. All taxane compounds have poor chemicals, cosmetics, and foods. water solubility. (U.S. Patent Application Publication no. 2007/0032438). Other medicinally important, but insoluble BACKGROUND ART or poorly soluble diterpenes include retinoids (vitamin A, retinol (vitamin A1), dehydroretinol (vitamin A2), retinoic Important Compounds Insoluble in Water acid, 13-cis-retinoic acid and other retinol derivatives, 0003 Poor aqueous solubility is a common obstacle to ginkgolides, and forsakolin (a promising drug for the treat delivering pharmaceuticals or other bioactive compounds and ment of glaucoma, congestive heart failure, and bronchial is a major challenge in formulating new drug products. In a asthma). study of kinetic aqueous solubility of commercial drugs, 87% 0005 Quinoline alkaloids. Quinoline alkaloids are alka were found to have solubility in water of 265 lug/mL and loids that possess quinoline in their structures and are terpe 7%s20 ug/mL (Lipinski, C., et al., Adv. Drug Deliv. Rev. noid indole alkaloid modifications. Camptothecins isolated (1997) 23:3-25). The minimum acceptable aqueous solubility from the Camptotheca acuminata trees (Family Nyssaceae) for a drug is about 52 ug/mL Solubility based on 1 mg/kg are quinoline alkaloids.
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