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ME Manning Et Al., Chem. Abstract 94.102538, 1981 USOO6992O79B2 (12) United States Patent (10) Patent No.: US 6,992,079 B2 Brugnara et al. (45) Date of Patent: *Jan. 31, 2006 (54) SUBSTITUTED 4,006,023 A 2/1977 McLaughlin et al. ....... 96/90 R 11-PHENYL-DBENZAZEPINE COMPOUNDS 4,806,685 A 2/1989 Abraham et al. ........... 563/324 USEFUL FOR THE TREATMENT OR 5,273,992 A 12/1993 Brugnara et al. ..... ... 514/398 5,358,959 A 10/1994 Halperin et al. ...... ... 514/396 ERR2E, RMAL cell 5,430,062. A 7/1995 Cushman et al. ........... 514/646 5,512.563 A * 4/1996 Albright et al. ............ 514/217 PROLIFERATION 6,063,921 A 5/2000 Moussa et al. (75) Inventors: Carlo Brugnara, Newton Highlands, 6,291,4496,201,120 B1 9/20013/2001 Ms t alal. MA (US); Jose Halperin, Brookline, 6,534,497 B1 * 3/2003 Brugnara et al. ........... 514/217 MA (US); Rudolf Fluckiger, Brookline, 2001/0007030 A1 7/2001 Moussa et al. MA (US); Emile M. Bellott, Jr., Beverly, MA (US); Richard John FOREIGN PATENT DOCUMENTS Lombardy, Littleton, MA (US); John EP O 323 740 A2 7/1989 J. Clifford, Arlington, MA (US); EP O 583 665 A2 2/1994 Ying-Duo Gao, Edison, NJ (US); Reem EP O 636 608 A1 2/1995 M. Haidar, Woburn, MA (US); Eugene JP OS 58894 3/1993 W. Kelleher, Medford, MA (US); Adel WO WO95/26720 10/1995 M. Moussa, Burlington, MA (US); WO WO 96/08240 3/1996 Yesh P. Sachdeva, Concord, MA (US); W W 't f1. Minghua Sun, Libertyville, IL (US); Heather N. Taft, Littleton, MA (US); WO WO 99/26928 6/1999 Michael H. Zeldin, Cambridge, MA OTHER PUBLICATIONS Starnes, Jr., Chem. Abstract 69:43555. 1968.* (73) ASSignees: restry's sole Koelsch. Chem. Abstract 55:9360. 1961. Melileen Corporation, Boston, Gagnon, Beilstein Reg. No. 4924895. 1929.* MA (US); NuChem Pharmaceuticals Dakkouri et al., Chem. Abstract 125:305256, 1997.* Inc., Toronto Enokida et al., Chem. Abstract 125:39835, 1996.* (*)* ) Notice: Sub.E. disclai"E"ME h f thi ManningBanli et al., et al.,Chem. Chem. Abstract Abstract 107:58774, 94.102538, 1987.* 1981." U.S.C. 154(b) by 0 days. Omenn, Cancer Prevention, Cecil Textbook of Medicine, 20th Edition, vol. 2, pp. 1008-1010, 1996.* Sasakura et al. Synthesis of 11-phenyl-5 clTh Air tentent IS Subjectbiect tto a tterminal 1 dISdis- 6-dihydro-11H-dibenz(b,e)azepines derivatives, Heteros cycles, vol. 15, No. 1, pp. 421-425, 1981.* Simone, Oncology: Introduction, Cecil Textbook of Medi (21)21) Appl. No.: 10/013,10/013,308 cine, 20ths Edition, vol. 1, pp. 1004–1008,s 1996.* (22) Filed: Dec. 7, 2001 Brugnara, C., et al., “Oral Administration of Clotrimazole (65) Prior Publication Data and Blockade o Human Erytrocyte Ca++-Activated K+ Channel: the Imidazole Ring is not Required for Inhibitory US 2004/0002486 A1 Jan. 1, 2004 Activity,” JPRT 273:266–272 (1995). O O Skehan, P., et al., “New Colorimetric Cytotoxicity Assay for Related U.S. Application Data Anticancer-Drug Screening.” J. Natl. Cancer InSt. (63) Continuation-in-part of application No. 09/554,848, filed as 82:1107–1112 (1990). application No. PCT/US98/24787 on Nov. 20, 1998, now Pat. No. 6,534,497, which is a continuation of application (Continued) No. 08/975,592, filed on Nov. 20, 1997, now abandoned. (51) Int. Cl. Primary Examiner Deepak Rao A6 IK3I/55 (2006.01) (74) Attorney, Agent, or Firm-Fish & Richardson P.C. C07D 233/18 (2006.01) (57) ABSTRACT (52) U.S. Cl. ........................................ 514/217; 540/587. The present invention provides Substituted 11-phenyl (58) Field of Classification Search ................. 540,587; dibenzazepine compounds which are specific, potent and 514/217 safe inhibitors of mammalian cell proliferation. The com See application file for complete Search history. pounds can be used to inhibit mammalian cell proliferation in Situ as a therapeutic approach towards the treatment or (56) References Cited prevention of diseases characterized by abnormal cell proliferation, Such as cancer. U.S. PATENT DOCUMENTS 3.546,155 A * 12/1970 Morgan ....................... 260/47 22 Claims, 51 Drawing Sheets US 6,992,079 B2 Page 2 OTHER PUBLICATIONS Brugnara, C., et al., “Erythrocyte Gardos Channel and Sickle Cell Disease: Pathophysiology and Clinical Signifi Aldrich Catalog, 1994–1995: Compounds 13, 484-8; cance, Advanced Course and International Symposium On T8,380-1; 10.130–3; D21,320-9; 32.543–0; 35,890-8; "Membrane Transporters and Channels' Program and T8.160-4; 25,657-9; T8.470-0; T8.417–7; T8,360-7; Abstracts, Lecture 34 (1995). S36.533–5; S50,949-3; 37.411-3; 37,152–1; 30.151-5; Brugnara, C., et al., “Therapy with Oral Clotrimazole 27,520-4; 34.182-7, 35,889–4; 584.240–0; S79.226-8; Induces Inhibition of the Gardos Channel and Reduction of 27,519-0, S64,640; S81,477-6; 36,005-8; S70.627-2; S34, Erythrocyte Dehydration in Patients with Sickle Cell Dis 966–6; S87.739–5; 11,500-2; S83,881-0; S58.110-0; ease,” J. Clin. Invest., 97(5):1227–1234 (1996). 21.560–0; S91,408-8; S60,147-0; S83,571-4; S82,654–5; Burgess, M.A., et al., “Clotrimazole (Bay b 5097): In Vitro S8,388-2; S94,371-1; S87,649-6; S83,719-9; S83,042–9; and Clinical Pharmacological Studies' Antimicrobial Agents S823,162-4; S81,468-7, S82,290–6; S79,387. and Chemotherapy, 2(6):423-426 (1972). Ando, W., et al., “A Novel Reduction of C.-Aryl Alkanols by Byers, H.R., et al., “Organ-Specific Metastases in Immu Diiododimethylsilane,” Tetrahedron Letters, 51:4941-4942 nodeficient Mice Injected with Human Melanoma Cells: a (1979). Quantative Pathological Analysis,” Melanoma Research, Barton, D. H. R., et al., “Pentavalent Organobismuth 3:247-253 (1993). Reagents. Part 3. Phenylation of Enols and of Enolate and Carter, A. J., et al., “Morphologic Characteristics of Lesion Other Anions.” J. Chem. Soc. Perkin Trans., 1:2667–2675 Formation and Time Course of Smooth Muscle Cell Prolif eration in a Porcine Proliferative Restenosis Model,” JACC, (1985). 24(5):1398–1405 (1994). Barton, D. H. R., et al., “Pentavalent Organobismuth Charache, S., et al., “Failure of Desmopressin to Lower Reagents. Part 3. Phenylation of Enols and of Enolate and Serum Sodium or Prevent Crisis in Patients with Sickle Cell Other Anions.” General Org. Chem., 105:531, col. 2, Anemia,” Blood, 58(5):892–896 (1981). Abstract No. 208158b (1986). Charache, S., et al., “Effect of Hydroxyurea on the Fre Bartroli, J., et al., “Synthesis and Antifungal Activity of a quency of Painful Crises in Sickle Cell Anemia,” The New Series of Difluorotritylimidazoles, Arzneim.-Forsch./Drug England Journal of Medicine, 332(20): 1317-1322 (1995). Res., 421(6):832–835 (1992). Clark, M. R., et al., “Hydration of Sickle Cells Using the Benjamin, L. J., et al., “A Collaborative, Double-Blind Sodium Ionophore Monensin,” J. Clin. Invest., 70: Randomized Study of Cetiedil Cirrate in Sickle Cell Crisis,” 1074–1080 (1982). Blood, 67(5): 1442–1447 (1986). Conte, L., et al., “Percutaneous Absorption and Skin Dis Benzaquen, L. R., et al., “Clotrimazole Inhibits Cell Prolif tribution of 'CFlutrimazole in Mini-pigs.” Arzneim-For eration in vitro and in vivo,” Nature Medicine, 1(6):534-540 Sch./Drug Res., 421(6):847-853 (1992). (1995). Conte, L., et al., “Pharmacokinetic Study of 'CFlutrima Zole after Oral and Intravenous Administration in Dogs,” Bergman, J., et al., “Synthesis and Studies of Tris-In Arzneim-Forsch/Drug Res., 421(6):854-858 (1992). dolobenzenes and Related Compounds.” Tetrahedron, Corbett, T. H., “Preclinical Anticancer Activity of Crypto 36:1445–1450 (1980). phycin-8,” Journal of Experimental Therapuetics & Oncol Bergman, J., et al., “Synthesis and Studies of Tris-In ogy, 1:95-108 (1996). dolobenzenes and Related Compounds,” Chemical DeFranceschi, L., et al., “Treatment with Oral Clotrimazole Abstracts, 94:368, col. 1, Abstract No. 3948s (1981). Blocks Ca'-Activated K Transport and Reverses Eryth Berkowitz, L. R., et al., “An Analysis of the Mechanism by rocyte Dehydration in Transgenic SAD Mice,” J. Clin. Which Cetiedil Inhibits the Gardos Phenomenon,” American Invest., 93:1670–1676 (1994). Journal of Hematology, 17:217-223 (1984). DeFranceschi, L., et al., “Reduction of K-Cl Cotransport Beutler, E., et al., “The Removal of Leukocytes and Platelets Mediated Erythrocyte Dehydration by Dietary Magnesium from Whole Blood,” J. Lab. Clin Med., 88(2):328–333 Supplements in Patients with Sickle Cell Disease.” Blood, (1976). 548a;2580 (1996). Bontems, F., et al., “Analysis of Side-Chain Organization on Duchene, P., et al., “Pharmacokinetic Profile of 'CFlut a Refined Model of Charybdotoxin: Structural and Func rimazole Following Single Topical Application in Normal tional Implications.” Biochemistry, 31:7756–7764 (1992). and Scarified Skin of Healthy Volunteers.” Arzneim.-For Sch./Drug Res., 421(6):861-863 (1992). Brugnara, C., et al., “Ca'-Activated K Transport in Eryth Duhm, B., et al., “The Pharmacokinetics of Clotrimazole rocytes,” Journal of Biological Chemistry, “C.” Postgraduate Medical Journal, Jul. Supp. 13-16 268(12):8760-8768 (1993). (1974). Brugnara, C., et al., “Inhibition of Ca-Dependent K. Dykes, D. J., et al., “Development of Human Tumor Transport and Cell Dehydration in Sickle Erythrocytes by Xenograft Models for In Vivo Evaluation of New Antihumor Clotrimazole and Other Imadazole Derivatives.' J. Clin. Drugs.” Immunodeficient Mice in Oncology, 42:1-22 Invest., 92:520–526 (1993). (1992). Brugnara, C., et al., “Inhibition of Gardos Channel and Red Epstein, R. J., et al., “Corneal Neovascularization,” Cornea, Cell Dehydration by Oral Administration of Clotrimazole in 6(4):250–257 (1987). Sickle Cell Disease,” Blood, 220a:865 (1994).
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