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12) United States Patent 10) Patent No.: US 7,173,129 B2

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12) United States Patent 10) Patent No.: US 7,173,129 B2 US007 173129B2 12) United States Patent 10) Patent No.: US 7,173,1299 9 B2 Worsencroft et al. (45) Date of Patent: Feb. 6, 2007 (54) SULFONAMIDE-SUBSTITUTED CHALCONE 5,811,449 A 9, 1998 Medford et al. DERVATIVES AND THEIR USE TO TREAT 5,821,260 A 10/1998 Medford et al. DISEASES 5,846,959 A 12/1998 Medford et al. 5,877,203 A 3, 1999 Medford et al. (75) Inventors: Kimberly J. Worsencroft, Alpharetta, 5,951,841 A 9/1999 Wehlage et al. GA (US); Liming Ni, Duluth, GA (US); 6,046,212 A 4/2000 Zwaagstra et al. Zhihong Ye, Lilburn, GA (US); 6,423,740 B1 7/2002 Bombardelli et al. Charleso, Meng, Alpharetta, GA 6,462,075 B1 10/2002 Bowen et al. (US); M. David Weingarten s 6,608, 101 B1 8/2003 Ni et al. s 2003/0232877 A1 12/2003 Sikorski et al. SWISERus) 2003/0236298 Al 12/2003 Meng et al. SE A. Sikorski Atlanta GA (US) 2004/0048858 A1 3/2004 Sikorski et al. (73) Assignee: Athero Genics, Inc., Alpharetta, GA FOREIGN PATENT DOCUMENTS US (US) EP 307762 3, 1989 (*) Notice: Subject to any disclaimer, the term of this EP O 271 307 1, 1992 patent is extended or adjusted under 35 JP 63.01.0720 T 1986 U.S.C. 154(b) by 360 days. JP O4217621 10, 1990 JP O6092950 9, 1992 (21) Appl. No.: 10/863,115 JP 06116206 10, 1992 JP O733O814 6, 1994 (22) Filed: Jun. 7, 2004 WO WO95/1576O 6, 1995 (65) Prior Publication Data (Continued) US 2005/0049236A1 Mar. 3, 2005 OTHER PUBLICATIONS Related U.S. Application Data Liu et al., “Antimalarial Alkoxylated and Hydroxylated Chalones: (60) Provisional application No. 60/476,708, filed on Jun. Structures-Activity Relationship Analysis”. J.Med. Chem. 2001, 44. 6, 2003. 4443-4452. s Herencia, et al., “Novel Anti-inflammatory Chalcone Derivatives (51) Int. Cl. Inhibit the Induction of Nitric Oxide Synthase and CO7D 413/00 (2006.01) Cyclooxygenase-2 in Mouse Peritoneal Macrophages'. FEBS Let CO7D 49/00 (2006.01) ters, 1999, 453, 129-134 C07D 239/02 (2006.01) Herencia, et al., Synthesis and Anti-inflammatory Activity of CO7D 403/00 (2006.015 Chalcone Derivatives'. Bioorganic & Medicinal Chemistry Letters 8 (1998) 1169-1174. CO7D 405/00 (2006.01) (1998) CO7D 409/00 (2006.01) (Continued) CO7D 4II/00 (2006.01) Pri Examiner Brian Davis (52) U.S.544/372:544/374; Cl. ...................... 546/213:546/276.4: 544/137; 54.4/143:544/297; 546/280.4: sAST l(RCAp "I gent, or Firm—Alan Scrivner, Esq.; K1ngKing & 546/281.4: 548/194: 548/246; 548/247: 548/253; pald1ng 548/314.7: 548/315.1: 548/365.7: 548/406; (57) ABSTRACT 548/509: 548/510; 548/511; 548/571 (58) Field of Classification Search ..................... None See application file for complete search history. The invention relates to compounds, pharmaceutical com positions and methods of using compounds of the general (56) References Cited formula U.S. PATENT DOCUMENTS 3,595,656 A * 7/1971 Ruckert et al. ............. 430, 196 O H R3 4,085,135 A 4, 1978 Kyogoku et al. 4,855.438 A 8, 1989 Kaulen et al. 5,155,250 A 10, 1992 Parker et al. R1 21 V 5,217,999 A 6, 1993 Levitzki et al. N H 5,380,747 A 1/1995 Medford et al. R21 Ns R4 5,608.095 A 3, 1997 Parker et al. M \, 5,744,614 A 4, 1998 Merkle et al. O O R5 5,750,351 A 5, 1998 Medford et al. 5,773,209 A 6, 1998 Medford et al. 5,773,231 A 6, 1998 Medford et al. or its pharmaceutically acceptable salt or ester, wherein the 5,783,596 A 7, 1998 Medford et al. Substituents are defined in the application. 5,792,787 A 8, 1998 Medford et al. 5,807,884 A 9, 1998 Medford et al. 37 Claims, No Drawings US 7,173,129 B2 Page 2 FOREIGN PATENT DOCUMENTS Hsieh, et al., “Synthesis and Anti-inflammatory Effect of WO WO 96.20936 T 1996 Chalcones', J. Pharm. Pharmacol. 2000, 52; 163-171. WO WO 97.12613 4f1997 Jones, R.; Bischofberger, N., “Minireview: Nucleotide Prodrugs'. WO WO 98,23581 6, 1998 Antiviral Research, 27 (1995) 1-17. WO WO 98.51289 11, 1998 Yang, Y, et al., “Synthesis of Some 5-Substituted Indoles' Hetero WO WO 98,51662 11, 1998 WO WO 99.00114 1, 1999 cycles, 1992, 34(6), 1169-1175. WO WOOOf 47554 8, 2000 Zwaagstra, et al., “Synthesis and Structure-Activity Relationships of Carboxylated Chalcones: A Novel Series of CysLT (LT.) Recep OTHER PUBLICATIONS tor Antagonists”, J. Med. Chem., 1997, 40, 1075-1089. Hsieh et al., “Synthesis and Anti-inflammatory Effect of Chalcones and Related Compounds'. Pharmaceutical Research, 1998, vol. 15. No. 1, 39-46. * cited by examiner US 7,173,129 B2 1. 2 SULFONAMIDE-SUBSTITUTED CHALCONE ration of pharmaceutical compositions for the treatment of DERVATIVES AND THEIR USE TO TREAT prophylaxis of a number of serious diseases including i) DISEASES conditions relating to harmful effects of inflammatory cytok ines, ii) conditions involving infection by Helicobacter CROSS REFERENCE TO RELATED species, iii) conditions involving infections by viruses, iv) neoplastic disorders, and V) conditions caused by microor APPLICATIONS ganisms or parasites. This application claims priority to U.S. provisional patent U.S. Pat. No. 4,085,135 to Kyogoku et al. discloses a application Ser. No. 60/476,708 filed Jun. 6, 2003. process for preparation of 2'-(carboxymethoxy)-chalcones 10 having antigastric and anti duodenal activities with low FIELD OF THE INVENTION toxicity and high absorptive ratio in the body. European Patent No 307762 assigned to Hofmann-La The present invention is in the field of novel chalcone Roche discloses substituted phenyl chalcones. derivatives, pharmaceutical compositions and methods for Herencia, et al., in Synthesis and Anti-inflammatory Activity of Chalcone Derivatives, Bioorganic & Medicinal treating a variety of diseases and disorders, including 15 inflammation and cardiovascular disease. Chemistry Letters 8 (1998) 1169–1174, discloses certain chalcone derivatives with anti-inflammatory activity. BACKGROUND OF THE INVENTION Hsieh, et al., Synthesis and Antiinflammatory Effect of Chalcones, J. Pharm. Pharmacol. 2000, 52; 163–171 Adhesion of leukocytes to the endothelium represents a describes that certain chalcones have potent antiinflamma fundamental, early event in a wide variety of inflammatory tory activity. conditions, autoimmune disorders and bacterial and viral Zwaagstra, et al., Synthesis and Structure-Activity Rela infections. Leukocyte recruitment to endothelium is medi tionships of Carboxylated Chalcones: A Novel Series of ated in part by the inducible expression of adhesion mol CysLT (LT) Receptor Antagonists; J. Med. Chem., 1997, ecules on the surface of endothelial cells that interact with 40, 1075–1089 discloses that in a series of 2-, 3-, and counterreceptors on immune cells. Endothelial cells deter 25 4-(2-quinolinylmethoxy)- and 3- and 4-2-(2-quinolinyl) mine which types of leukocytes are recruited by selectively ethenyl-substituted, 2',3', 4', or 5' carboxylated chalcones, expressing specific adhesion molecules. Such as vascular certain compounds are CySLT receptor antagonists. cell adhesion molecule-1 (VCAM-1), intercellular adhesion JP 63010720 to Nippon Kayaku Co., LTD discloses that molecule-1 (ICAM-1), and E-selectin. VCAM-1 binds to the chalcone derivatives of the following formula (wherein R' integrin VLA-4 expressed on lymphocytes, monocytes, 30 and R are hydrogen or alkyl, and m and n are 0–3) are macrophages, eosinophils, and basophils but not neutro 5-lipoxygenase inhibitors and can be used in treating aller phils. This interaction facilitates the firm adhesion of these 21eS. leukocytes to the endothelium. VCAM-1 is an inducible gene that is not expressed, or expressed at very low levels, in normal tissues. VCAM-1 is upregulated in a number of R2 inflammatory diseases, including arthritis (including rheu 35 matoid arthritis), asthma, dermatitis, psoriasis, cystic fibro 2)J (OH)nOH sis, post transplantation late and chronic Solid organ rejec tion, multiple Sclerosis, Systemic lupus erythematosis, 1N SX inflammatory bowel diseases, autoimmune diabetes, dia (HO)-i- R betic retinopathy, rhinitis, ischemia-reperfusion injury, post 40 21 angioplasty restenosis, chronic obstructive pulmonary dis ease (COPD), glomerulonephritis, Graves disease, O gastrointestinal allergies, conjunctivitis, atherosclerosis, coronary artery disease, angina and Small artery disease. U.S. Pat. Nos. 5,750,351; 5,807,884; 5,811,449; 5,846, 45 JP 06116206 to Morinaga Milk Industry Co. Ltd, Japan, 959; 5,773,231, and 5,773,209 to Medford, et al., as well as discloses chalcones of the following structure as 5-lipoxy the corresponding WO95/30415 to Emory University indi genase inhibitors, wherein R is acyl and R'-R are hydro cate that polyunsaturated fatty acids (“PUFAs) and their gen, lower alkyl, lower alkoxy or halo, and specifically that hydroperoxides (“ox-PUFAs), which are important com in which R is acyl and R'-R are hydrogen. ponents of oxidatively modified low density lipoprotein 50 (LDL), induce the expression of VCAM-1, but not intrac ellular adhesion molecule-1 (ICAM-1) or E-selectin in R human aortic endothelial cells, through a mechanism that is R R3 not mediated by cytokines or other noncytokine signals. This is a fundamental discovery of an important and previously unknown biological pathway in VCAM-1 mediated immune 55 HOC responses. As non-limiting examples, linoleic acid, linolenic R4 acid, arachidonic acid, linoleyl hydroperoxide (13-HPODE) Rs and arachidonic hydroperoxide (15-HPETE) induce cell RO surface gene expression of VCAM-1 but not ICAM-1 or E-selectin. Saturated fatty acids (such as Stearic acid) and 60 O monounsaturated fatty acids (such as oleic acid) do not IR = Ac induce the expression of VCAM-1, ICAM-1 or E-selectin.
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