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(12) United States Patent (10) Patent No.: US 9.403,841 B2 Wikberg Et Al

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(12) United States Patent (10) Patent No.: US 9.403,841 B2 Wikberg Et Al USOO9403841 B2 (12) United States Patent (10) Patent No.: US 9.403,841 B2 Wikberg et al. (45) Date of Patent: Aug. 2, 2016 (54) PHRAGAMALIN LIMONOIDS FOR THE Ansel et al., “Pharmaceutical Dosage Forms and Drug Delivery Sys TREATMENT OF SEXUAL DYSFUNCTION tems. Seventh Edition, 1999, ISBN 0-683-30572-7. Arndt et al., “The Structure of Phragmalin a Meliacin with a (71) Applicant: DICOTYLEDON AB, Sigtuna (SE) Norbornane Part Skeleton. Tetrahedron, 1972, 28:2333-2340. Baldwin, “Sexual dysfunction associated with antidepressant drugs.” (72) Inventors: Jarl Wikberg, Sigtuna (SE); Aigars Expert Opinion Drug Safety, 2004, 3(5):457-470. Basson, R., “Female Sexual Response: The Role of Drugs in the Jirgensons, Riga (LV); Edvards Management of Sexual Dysfunction.” Gynecol., 2001, 98(2):350 Liepinsh, Riga (LV) 353. Berge et al., “Pharmaceutical Salts.” J. Pharm. Sci., 1977, 66:1-19. (73) Assignee: DICOTYLEDON AB, Sigtuna (SE) Bernasconi et al., “Nucleophilic Addition to Olefins. 5 Reaction of 1,1-Dinitro-2,2diphenylethylene with Water and Hydroxide Ion in (*) Notice: Subject to any disclaimer, the term of this 50% MeSO-50% Water. Complete Kinetic Analysis of Hydrolytic patent is extended or adjusted under 35 Cleavage of the C=C Double Bond in Acidic and Basic Solution.” J. U.S.C. 154(b) by 0 days. Am. Chem. Soc., 1981, 103 (16):4850-4860. Bolour et al., “Testoteronetherapy in women: a review.” International (21) Appl. No.: 14/374,356 Journal of Impotence Research, 2005, 17:399-408. Boto, A. et al., “Hypervalent iodine reagents: Synthesis of a steroidal (22) PCT Filed: Jan. 25, 2013 orthoacetate by a radical reaction.” Tetrahedron Letters, 1994, 35(37):6933-6936. (86). PCT No.: PCT/EP2013/OS 1413 Cappelleri et al., “The Sexual Health Inventory for Men (SHIM): a 5-year review of research and clinical experience.” International S371 (c)(1), Journal of Impotence Research, 2005, 17:307-319. (2) Date: Jul. 24, 2014 Carré, A., “Polar Interactions at liquid polymer interfaces,” J. Adhe sion Sci. Technol., 2007, vol. 21, No. 10, pp. 961-981. (87) PCT Pub. No.: WO2013/110744 Charman et al., “Self-Emulsifying drug Delivery Systems: Formula tion and Biopharmaceutic Evaluation of an Investional Lipophilic PCT Pub. Date: Aug. 1, 2013 Compound.” Pharmaceutical Research, 1992, 9(1): 87-93. (65) Prior Publication Data Chen et al., “Phragmalin Limonoids from Chukrasia tabularis var. velutina.” Planta Medica, 2012, vol. 78, No. 03, pp. 286-290. US 2015/OO1161.6 A1 Jan. 8, 2015 Coombes et al., “Phragmalin limonoids from the Madagascan Meliaceae Neobeguea leandreana.” Journal of Natural Products, 2003, vol. 66, No. 6, pp. 735-738. (30) Foreign Application Priority Data Dálaigh et al., “Asymmetric acyl-transfer promoted by readily assembled chiral 4-N,N-dialkylaminopyridine derivates.” Org. Jan. 25, 2012 (SE) ....................................... 12OOO52 Biomol. Chem., 2006, 4:2785-2793. Nov. 6, 2012 (SE) ....................................... 12OO678 Davis, S. R. et al., “Circulating Androgen Levels and Self-reported Jan. 4, 2013 (SE) ....................................... 13OOO11 Sexual Function in Women.” JAMA, 2005, 294(1):91-96. Desset al., “A Useful 12-I-5Triacetoxyperiodinane (the Dess-Martin (51) Int. Cl. Periodinane) for the Selective Oxidation of Primary or Secondary CO7D 493/22 (2006.01) Alcohols and a Variety of Related 12-I5 Species'.” J. Am. Chem. CO7D 493/18 (2006.01) Soc., 1991, 113:7277-7287. Enserink et al., “Let’s Talk About Sex—and Drugs.” Science, 2005, (52) U.S. Cl. 3O8: 1578-1580. CPC ............ C07D493/22 (2013.01); C07D493/18 Gasteiger et al., “Chemoinformatics' 2003, ISBN 3-527-30681-1. (2013.01) Gebauer et al., “A Short and Enantiospecific Synthesis of (-)- (58) Field of Classification Search Nuphatamine.” Synlett, 2005, 18:2826-2828. CPC ....... ... C07D 493/18: C07D 493/22 Giuliano et al., “Neural control of erection.” Physiology & Behavior, USPC ........................................... 514/450; 549/275 2004, 83:189-201. See application file for complete search history. (Continued) (56) References Cited Primary Examiner — Taofiq A Solola U.S. PATENT DOCUMENTS (74) Attorney, Agent, or Firm — Michael Best & Friedrich LLP 2003. O180395 A1 9, 2003 Bueter (57) ABSTRACT FOREIGN PATENT DOCUMENTS The present invention relates to novel chemical compounds, JP 2005-2132O2 8, 2005 to methods for synthesis of such compounds, and to the use of WO WO 2007/031830 3, 2007 these novel compounds in the synthesis of other chemical WO WO 2008. 145996 12/2008 compounds that, interalia, may be used in the treatment of OTHER PUBLICATIONS sexual dysfunction, and for eliciting enhancing effects on sexual behavior. The invention also relates to remarkable Abdelgaleil, S.A.M. et al., “Antifeeding activity of limonoids from biological properties of the novel compounds in their capacity Khaua senegalesis (Meliaceae).” J. Appl. Ent., 2003, 127:236-239. of inducing aggressive behavior. Andersson, K.-E., “Pharmacology of Penile Erection.” Pharmaco logical Reviews, 2001, 53(3):417-450. 1 Claim, 6 Drawing Sheets US 9,403,841 B2 Page 2 (56) References Cited Paris, R.R. et al., “On the polyphenols (phenolic acids, flavonoids) in leaves of 2 Meliaceae species of Madagascar cedrelopsis-grevei and OTHER PUBLICATIONS Neobeguea-mahafalensis.” Plantes Medicinales et Phytotherapies, 1972, 6(4):311-319. Ebstract translation attached. Grumbach et al., “Hydrophilic Interaction Chromatography Using Ralph et al., “Ejaculatory disorders and sexual function.” BJU Inter Silica Columns for the Retention of Polar Analytes and Enhanced national, 2005, 95(9): 1181-1186. ESI-MS Sensitivity.” LCGS Asia Pacific, 2004, 7(4):38-44. Randrianarivelojosia et al., “A Limonoid from Neobeguea Hafez et al., “Erectile Dysfuntion: Anatomical Parameters, Etiology, mahafelensis.” Phytochemistry, 1999, 52(6): 1141-1143. Diagnosis and Therapy.” Archives of Andrology, 2005, 51: 15-31. Rasoanaivo et al., “Medical plants used to treat malaria in Hoshino et al., Database WPI Week 200555 Thomson Scientific, Madagascar.” Journal of Ethnopharmacology, 1992, 37:117-127. London, GB, AN 2005-537835 XP002538721. Rasoanaivo et al., “Screening Extracts of Madagascan Plants in International Search Report and Written Opinion for Application No. Search of Antiplasmodial Compounds.” Phytotherapy Research PCT/EP2013/051413 dated Sep. 12, 2013 (20 pages). (2004) 18, 742-747. Kendirci, M. et al., “The Impact of Vascular Risk Factors on Erectile Rosen et al., “The International Index of Erectile Function (IIEF): A Function.” Drugs of Today, 2005, 41(1):65-74. Multidimensional Scale for Assessment of Erectile Dysfunction.” Kipassa, N.T., PhD thesis, Kagoshima University, Mar. 2008: Struc Urology, 1997, 49(6):822-30. tural studies of tetranortriterpenoids from the Congolese species of Ruiz-Jimenez et al., “Forward-and-back dynamic ultrasound-as Entandrophragma angolense; and efficient short step synthesis of sisted extraction of fat bakery products.” Anal Chim Acta, 2004, Corey's Tamiflu intermediate. SO2:75-82. Kotsos, M.P., MSc thesis, University of Natal, 1997: Extractives from Ruiz-Jimenez et al., “Use of chemometrics and mid infrared spec Neobeguea mahafalensis and Cedrelopsis grevei. troscopy for the selection of extraction alternatives to reference ana Krauss et al., “A New Approach Towards (-)-4-Ipomeanol and its lytical methods for total fat isolation.” Analytica Chimica Acta, 2004, 2-Furyl Regioisomer.” Turkish J Chemistry, 2005, 29(6):635-639. 525:159-169. Sandroni, P. “Aphrodisiacs past and present: a historical review.” Li et al., “Two new limonoids from the stem barks of Chukrasia Clinical Autonomic Research 2001, 11:303-307. tabularis var. velutina..' Journal of Asian Natural Products Research, Shabbir, M. et al., “Erectile dysfuntion: an underdiagnosed condition 2011, 13(9):781-786. associated with multiple risk factors.” Current Medical Research and Liao et al., “Plant orthoesters.” Chemical Reviews, 2009, vol. 109, Opinion, 2004, 2005):603-606. No. 3, 1092-1140. Tamburlin-Thumin et al., “Synthesis and biological evaluation of Liu et al., "Kv1.2 potassium channel inhibitors from Chukrasia O-alkylated tropolones and related O-ketohydroxy derivates as tabularis.” Organic & Biomolecular Chemistry, 2012, vol. 10, No. 7. ribonucleotide reductase inhibitors.' Eur, J. Med. Chem., 2001, p. 1448-1458. 36:561-568. Luo et al., "Chukvelutilides A-F. phragmalin limonoids from the Von Soxhlet, F. "Dinglers Polytechnisches Journal,” 1879, stem barks of Chukrasia tabularis var. velutina.” Thetrahedron, 2009, 232:461-5 (translation of abstract attached). vol. 65, No. 17, pp. 3425-3431. Yang et al., “Comparison of the International Index of Erectile Func Luo et al., “D-Ring-Opened Phragmalin-Type Limonoids from tion erectile domain scores and nocturnal penile tumescence and Chukrasia tabularis var. velutina.” Chemistry & Biodiversity, 2011, rigidity measurements: does one predict the other?” BJU Int., 2006, vol. 8, No. 12, pp. 2261-2269. 98(1):105-9. Luo et al., “Two new C-15 enolic acyl phragmalin-type limonoids Berge et al., “Resveratrol inhibits benzoapyrene-DNA adduct for from Chukrasia tabularis var. velutina,” Natural Product Research, mation in human bronchial epithelial cells.” British Journal of Can 2011, 27(7):597-602. cer, 2004, 91, 333-338. Mackay et al., “Enantioselective Acylation Using a Second-Genara Blay, G. et al., “A Non-Catalyzed Ring-Opening Aminolysis Reac tion of Sequiterpene Lactone.” Tetrahedron Letters, 1994, vol. 35. tion P-Ary1-2-phosphabicyclo[3.3.0 octane Catalyst.” J. Org. Chem.
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