Heterocyclic analogs of diphenylethylene compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C548S227000, C548S226000, C548S318500, C514S369000, C514S376000, C514S389000, C514S439000, C514S441000

Reexamination Certificate

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10808519

ABSTRACT:
Novel diphenylethylene compounds and derivatives thereof containing thiazolidinedione or oxazolidinedione moieties are provided which are effective in lowering blood glucose level, serum insulin, triglyceride and free fatty acid levels in animal models of Type II diabetes. In contrast to previously reported thiazolidinedione compounds, known to lower leptin levels, the present compounds increase leptin levels and have no known liver toxicity. The compounds are disclosed as useful for a variety of treatments including the treatment of inflammation, inflammatory and immunological diseases, insulin resistance, hyperlipidemia, coronary artery disease, cancer and multiple sclerosis.

REFERENCES:
patent: 3609183 (1971-09-01), DeWald et al.
patent: 3683009 (1972-08-01), Middleton
patent: 3846398 (1974-11-01), Hirschmann et al.
patent: 4092335 (1978-05-01), Gruszecki et al.
patent: 4217366 (1980-08-01), Kikumoto et al.
patent: 4271186 (1981-06-01), Forster et al.
patent: 4284637 (1981-08-01), Kikumoto et al.
patent: 4297429 (1981-10-01), Kanada et al.
patent: 4310534 (1982-01-01), Kikumoto et al.
patent: 4312855 (1982-01-01), Grand
patent: 4326055 (1982-04-01), Loeliger
patent: 4716905 (1988-01-01), Schmued
patent: 4866086 (1989-09-01), Boyle et al.
patent: 4929635 (1990-05-01), Coquelet et al.
patent: 4940707 (1990-07-01), Klaus et al.
patent: 5087637 (1992-02-01), Janssen et al.
patent: 5158966 (1992-10-01), Lafferty et al.
patent: 5162337 (1992-11-01), Elbrecht et al.
patent: 5171753 (1992-12-01), Munson, Jr. et al.
patent: 5189056 (1993-02-01), Orlando et al.
patent: 5246936 (1993-09-01), Treacy et al.
patent: 5250562 (1993-10-01), Klaus et al.
patent: 5314693 (1994-05-01), Suga
patent: 5378705 (1995-01-01), Klaus et al.
patent: 5409953 (1995-04-01), Pettit et al.
patent: 5430062 (1995-07-01), Cushman et al.
patent: 5494932 (1996-02-01), Cardin et al.
patent: 5521160 (1996-05-01), Chucholowski et al.
patent: 5525632 (1996-06-01), Obsumi et al.
patent: 5532129 (1996-07-01), Heller
patent: 5559151 (1996-09-01), Adorante et al.
patent: 5565191 (1996-10-01), Raspanti
patent: 5565322 (1996-10-01), Heller
patent: 5569786 (1996-10-01), Pettit et al.
patent: 5583128 (1996-12-01), Bhatnagar
patent: 5589506 (1996-12-01), Hashimoto et al.
patent: 5672625 (1997-09-01), Cardin et al.
patent: 5674906 (1997-10-01), Hatanaka et al.
patent: 5705530 (1998-01-01), Adorante et al.
patent: 5716928 (1998-02-01), Benet et al.
patent: 5731353 (1998-03-01), Ohsumi et al.
patent: 5733909 (1998-03-01), Black et al.
patent: 5767268 (1998-06-01), Chucholowski et al.
patent: 5770620 (1998-06-01), Mjalli et al.
patent: 5827898 (1998-10-01), Khandwala et al.
patent: 5972973 (1999-10-01), Whitcomb
patent: 5985884 (1999-11-01), Lohray et al.
patent: 5990139 (1999-11-01), Yano et al.
patent: 6008237 (1999-12-01), Sahoo et al.
patent: 6011031 (2000-01-01), Lohray et al.
patent: 6011036 (2000-01-01), Lohray et al.
patent: 6030973 (2000-02-01), Lohray et al.
patent: 6034110 (2000-03-01), Nagpal et al.
patent: 6046202 (2000-04-01), Antonucci et al.
patent: 6046222 (2000-04-01), Antonucci et al.
patent: 6080765 (2000-06-01), Ikeda et al.
patent: 6103742 (2000-08-01), Ikeda et al.
patent: 6107323 (2000-08-01), Tamura et al.
patent: 6110948 (2000-08-01), Momose et al.
patent: 6110951 (2000-08-01), Pershadsingh et al.
patent: 6114526 (2000-09-01), Lohray et al.
patent: 6117893 (2000-09-01), Fujita et al.
patent: 6121294 (2000-09-01), Ikeda et al.
patent: 6121295 (2000-09-01), Ikeda et al.
patent: 6130216 (2000-10-01), Antonucci et al.
patent: 6133293 (2000-10-01), Ikeda et al.
patent: 6133295 (2000-10-01), Ikeda et al.
patent: 6245814 (2001-06-01), Nag et al.
patent: 6331633 (2001-12-01), Neogi et al.
patent: 6624197 (2003-09-01), Nag et al.
patent: 2002/0025975 (2002-02-01), Nag et al.
patent: 2003/0181494 (2003-09-01), Neogi et al.
patent: 32128 (1981-06-01), None
Sohda et al. “Antiulcer Activity of 5-benzylthiazolidine-2,4-dione derivatives”Chem. Pharm. Bull. 31:2 (1983) 560-9.
Giles et al. “Regiospecific Reduction of 5-benzylidene-2,4-thiazolidinediones and 4-oxo-2-thiazolidinethiones Using Lithium Borohydride in Pyridine and Tetrahydrofuran”Tetrahedron56:26 (2000) 4531-4537.
Myaoka et al. “Preparation of 2,4-Dioxo-1,2,3,4-Tetrahydroquinazoline Derivatives Having Blood Sugar-Lowering and Aldose Reductase-Inhibiting Activity”Japan Kokai Tokkyo Koho(1996).
Hulin et al. “Novel Thiazolidone-2,4-Diones as Patent Euglycemic Agents”J. Med. Chem. 35:10 (1992) 1853-64.
Pettit et al. “Isolation, Structure, Synthesis and Antimitotic Properties of Combretastttins B-3 and B-4 from Combretum Caffrum”Journal of Natural Products51:3 (1988) 517-527.
Green, Richard H. “Syntheses of Differanisole A”Tetrahedron Letters38:26 (1997) 4697-4700.
Reddy et al. “From Styrenes to Enanitopure α-Arylglycines in Two Steps”J. Am. Chem. Soc. 120 (1998) 1207-1217.
Momose et al. “Studies on Antidiabetic Agents. X.1)Synthesis and Biological Activities of Pioglitazone and Related Compounds”Chem. Pharm. Bull. 39(6) (1991) 1440-1445.
Cantello et al. “[[ω-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as Potent Antihyperglycemic Agents”J. Med. Chem. 37 (1994) 3977-3985.
Sohda et al. “Studies on Antidiabetic Agents. XII.1)Synthesis and Activity of the Metabolites of (±)-5-[-p-[2-(5-Ethyl-2-pyridyl)ethoxy]benzyl]-2,4-thiazolidinedione (Pioglitazone)”Chem. Pharm. Bull. 43(12) (1995) 2168-2172.
Willson et al. “The Structure-Activity Relationship between Peroxisome Proliferator-Activated Receptor γ Agonism and the Antihyperglycemic Activity of Thiazolidinediones”J. Med. Chem. 39 (1996) 665-668.
Tanis et al. “Synthesis and Biological Activity of Metabolites of the Antidiabetic; Antihyperglycemic Agent Pioglitazone”J. Med. Chem. 39 (1996) 5053-5063.
Shinkai et al. “Isoxazolidine-3,5-dione and Noncyclic 1,3-Dicarbonyl Compounds as Hypoglycemic Agents”J. Med. Chem. 41 (1998) 1927-1933.
Lohray et al. “Novel Euglycemic and Hypolipidemic Agents”J. Med. Chem. 41(1998)1619-1630.
Reddy et al. “Novel Antidiabetic and Hypolipidemic Agents. 5. Hydroxyl versus Benzyloxy Containing Chroman Derivatives”J. Med. Chem. 42 (1999) 3265-3278.
Turnbow MA, Smith LK, Garner CW. The oxazolidinedione CP-92,768-2 partially protects insulin receptor substrate-1 from dexamethasone down-regulation in 3T3-L1 adipocytes. Endocrinology. Apr. 1995; 136(4):1450-8.
Yoshioka T, Fujita T, Kanai T, Aizawa Y, Kurumada T, Hasegawa K, Horikoshi H. Studies on hindered phenols and analogues. 1. Hypolipidemic and hypoglycemic agents with ability to inhibit lipid peroxidation, J Med Chem. Feb. 1989; 32(2):421-8.
Zask A, Jirkovsky I, Nowicki JW, McCaleb ML. Synthesis and antihyperglycemic activity of novel 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones. J Med Chem. 33:5 (1990) 1418-23.
Sohda T, Mizuno K, Momose Y, Ikeda H, Fujita T, Meguro K. Studies on antidiabetic agents. 11. Novel thiazolidinedione derivatives as potent hypoglycemic and hypolipidemic agents. J Med Chem. Jul. 10, 1992;35(14):2617-26.
Hulin B, Newton LS, Lewis DM, Genereux PE, Gibbs EM, Clark DA. Hypoglycemic activity of a series of alpha-alkylthio and alpha-alkoxy carboxylic acids related to ciglitazone. J Med Chem. Sep. 27, 1996; 39(20):3897-907.
Arakawa K, Inamasu M, Matsumoto M, Okumura K, Yasuda K, Akatsuka H, Kawanami S, Watanabe A, Homma K, Saiga Y, Ozeki M, Iijima I. Novel benzoxazole 2,4-thiazolidinediones as potent hypoglycemic agents. Synthesis and structure-activity relationships. Chem Pharm Bull (Tokyo). Dec. 1997; 45(12):1984-93.
Dow et al. “Benzyloxazolidine-2,4-diones as Potent Hypoglycemic Agents” J. Med. Chem. 1991 vol. 34 1538-1544.
Sohda et al. “Studies on Antidiabetic Agents. II. Synthesis of 5-[4-(1-Methylcyclohexylmethoxy)-benzyl]thiazolidine-2,4-dione (ADD-3878) and Its Derivatives” Chemical & Pharmaceutical Bulletin 30:10 (Oct. 1982) pp. 3580-360

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