Antihyperglycemic Activity of Novel Substituted 3H-1,2,3,5-Oxathiadiazole 2-Oxides

Journal of Medicinal Chemistry

Volumn 35, Issue 7, 1992, Pages 1176-1183

  Ellingboe, John W ^a   Alessi, Thomas R ^a   Dolak, Terence M ^a   Nguyen, Thomas T ^a   Tomer, John D ^a   Guzzo, Frieda ^a   Bagli, Jehan F ^a   McCaleb, Michael L ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3H 1,2,3,5 OXATHIADIAZOLE 2 OXIDE DERIVATIVE; 4 [(2 NAPHTHYL)METHYL] 3H 1,2,3,5 OXATHIADIAZOLE 2 OXIDE; CIGLITAZONE; DRUG CARRIER; GLUCOSE; ORAL ANTIDIABETIC AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DIABETES MELLITUS; DOSE RESPONSE; DRUG EFFICACY; DRUG SYNTHESIS; FATTY ACID OXIDATION; GLUCOSE BLOOD LEVEL; GLUCOSE TOLERANCE TEST; HYPERGLYCEMIA; HYPOGLYCEMIA; INSULIN RESISTANCE; LIPOPHILICITY; MALE; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; RAT; SIDE EFFECT;

ANIMAL; BLOOD GLUCOSE; COMPARATIVE STUDY; DIABETES MELLITUS, EXPERIMENTAL; HYPOGLYCEMIC AGENTS; MALE; MICE; MICE, INBRED C57BL; MOLECULAR STRUCTURE; RATS; RATS, ZUCKER; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 0026642950     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00085a002     Document Type: Article

References (48)

1. Ferner, R. E. Oral Hypoglycemic Agents. Med. Clin. North Am. 1988, 72, 1323-1335.
2. Ferner, R. E. Oral Hypoglycemic Agents. FDA Drug Bull. 1977, 7, 14-16.
3. Genuth, S. Insulin Use in NIDDM. Diabetes Care 1990, 13, 1240-1264
4. Puls, W.; Keup, U.; Krause, H. P.; Müller, L.; Schmidt, D. D.; Thomas, G.; Truscheit, E. Pharmacology of a Glucosidase Inhibitor. Front. Horm. Res. 1980, 7, 235-247.
5. Sohda, T.; Mizuno, K.; Imamiya, E.; Sugiyama, Y.; Fujita, T.; Kawamatsu, Y. Studies on Antidiabetic Agents. II. Synthesis of 5-[4-(1-Methylcyclohexylmethoxy) benzyl] thiazolidine-2,4-dione (ADD-3878) and Its Derivatives. Chem. Pharm. Bull. 1982, 30, 3580-3600
6. Fujita, T.; Sugiyama, Y.; Taketomi, S.; Sohda, T.; Kawamatsu, Y.; Iwatsuka, H.; Suzuoki, Z. Reduction of Insulin Resistance in Obese and/or Diabetic Animals by 5-[4-(l-Methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione (ADD-3878, U-63,287, Ciglitazone), a New Antidiabetic Agent. Diabetes 1983, 32, 804-810.
7. Chang, A. Y.; Wyse, B. M.; Gilchrist, B. J.; Peterson, T.; Diani, A. R. Ciglitazone, a New Hypoglycemic Agent I. Studies in ob/ob and db/db Mice, Diabetic Chinese Hamsters, and Normal and Streptozotocin-Diabetic Rats. Diabetes 1983, 32, 830-838.
8. Sohda, T.; Mizuno, K.; Tawada, H.; Sugiyama, Y.; Fujita, T.; Kawamatsu, Y. Studies on Antidiabetic Agents. I. Synthesis of 5-[4-(2-Methyl-2-phenylpropoxy)benzyl]thiazolidine-2,4-dione (AL-321) and Related Compounds. Chem. Pharm. Bull. 1982, 30, 3563-3573
9. Coica, J. R.; Morton, D. R. Antihyperglycaemic Thiazolidinediones: Ciglitazone and Its Analogues. In New Antidiabetic Drugs., Bailey, C. J., Flatt, P. R., Eds.; Smith-Gordon: London, 1990; pp 255-261.
10. Stevenson, R. W.; Hutson, N. J.; Krupp, M. N.; Volkman, R. A.; Holland, G. F.; Eggler, J. F.; Clark, D. A.; McPherson, R. K.; Hall, K. L.; Danbury, B. H.; Gibbs, E. M.; Kreutter, D. K. Actions of Novel Antidiabetic Agent Englitazone in Hyperglycemic Hyperinsulinemic ob/ob Mice. Diabetes 1990, 39, 1218-1227.
11. Larson, E. R.; Clark, D. A.; Stevenson, R. W. New Approaches to Diabetes. Ann. Rep. Med. Chem. 1989, 25, 205-213.
12. Zask, A.; Jirkovsky, I.; Nowicki, J. W.; McCaleb, M. L. Synthesis and Antihyperglycemic Activity of Novel 5-(Naphthalenylsulfonyl)-2,4-thiazolidinediones. J. Med. Chem. 1990, 33, 1418-1423
13. Kees, K. L.; Cheeseman, R. S.; Prozialeck, D. H.; Steiner, K. E. Perfluoro-N-[4(1H-tetrazol-5-ylmethyl)phenyl]alkanamides. A New Class of Oral Antidiabetic Agents. J. Med. Chem. 1989, 32, 11-13.
14. Dow, R. L.; Bechle, B. M.; Chou, T. T.; Clark, D. A.; Hulin, B.; Stevenson, R. W. Benzyloxazolidine-2,4-diones as Potent Hypoglycemic Agents. J. Med. Chem. 1991, 34, 1538-1544.
15. Eloy, F.; Lenaers, R. Synthesis of 2-Oxo-1,2,3,5-oxathiadiazoles. Bull. Soc. Chim. Belg. 1965, 74, 129-135.
16. Mulholland, T. P. C.; Preston, H. D.; Rosevear, D. T. Synthesis of Some Griseofulvin Analogues. J. Chem. Soc. 1965, 4939-4953
17. Zamet, J. J.; Haddadin, M. J.; Issidorides, C. H. Reaction of Benzofuran Oxides with Benzofuran-3(2H)-ones, and a New Synthesis of Benzofuro[2,3-b]quinoxalines. J. Chem. Soc., Perkin Trans. 1 1974, 1687-1691
18. Fries, K.; Finck, G. Homologs of Cumaranone and Their Derivatives. Chem. Ber. 1908, 41, 4271-4284.
19. Jung, M. E.; Abrecht, S. Improved Synthesis of 3-Substituted 7 -Methoxy benzofurans, Useful Intermediates for Preparation of Morphine Analogues. J. Org. Chem. 1988, 53, 423-425.
20. Anderson, W. K.; LaVoie, E. J.; Bottaro, J. C. Use of 2,3-Dichloropropene and 1,3-Dichlorobut-2-ene as Synthons for Heterocyclic Compounds: Synthesis of 2-Methylbenzo[b]-furans, 2-Methylbenzo[b]thiophens, and 4-Methyl-2ff-chromen. J. Chem. Soc., Perkin Trans. 1 1976, 1-4.
21. Cuberes, M. R.; Moreno-Manas, M.; Sanchez-Ferrando, F. Halogeno-Substituted 2-and 3-Methylbenzo[b]thiophens: Use of 1H NMR Spectral Analysis and 1H{H} Nuclear Overhauser Effect for Locating the Halogen Substituent. Magn. Reson. Chem. 1985, 23, 814-821.
22. Matsuki, Y.; Shoji, F. 5-Bromothianaphthene Derivatives. Nippon Kagaku Zasshi 1965, 86, 1067-1072.
23. Chan, J. H.-T.; Elix, J. A.; Ferguson, B. A. Annelated Furans. XVII The Wittig Reaction of Benzofuranones. Aust. J. Chem. 1975, 28, 1097-1111
24. Campaigne, E.; Neiss, E. S. Benzo[b]thiophene Derivatives. VII. Abnormal Substitution Product from 3-Chloromethylbenzo[b]thiophene. J. Heterocycl. Chem. 1965, 2, 231-235
25. Erba, C. Substituted Acetic Acids. British Patent 1 109 527, 1968.
26. Lal, B.; Seth, M.; Bhaduri, A. P.; Kar, K. Search for Vasopressin Antagonists: Syntheses and Biological Activity of α,-β-Diacrylic Acids. Indian J. Chem., Sect. B 1977, 15B, 744-746.
27. Mitsunobu, O. The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products. Synthesis 1981, 1-28.
28. Juby, P. F.; Hudyma, T. W. Preparation and Antiinflammatory Properties of Some 1-Substituted 3-(5-TetrazolylmethyDindoles and Homologs. J. Med. Chem. 1969, 12, 396-401.
29. Smith, T. H.; Fujiwara, A. N.; Lee, W. W.; Wu, H. Y.; Henry, D. W. Synthetic Approaches to Adriamycin. 2. Degradation of Daunorubicin to a Nonasymmetric Tetracyclic Ketone and Refunctionalization of the A Ring to Adriamycin. J. Org. Chem. 1977, 42, 3653-3660
30. Leuchs, H.; Schmidt, K. H. Producing Benzyl Cyanides and Homologs from Aralkyl Halides and Sodium Cyanide. British Patent 1 200 970, 1970.
31. Gracey, D. E. F.; Jackson, W. R.; McMullen, C. H.; Thompson, N. Stereochemistry of Organometallic Compounds. III. Interactions of Nonbonded Substituents in the Kinetically Controlled Reactions of Substituted Indans with Hexacarbonylchromium and Tricarbonyl(trispyridine)chromium. J. Chem. Soc. B 1969, 1197-1203
32. Ziegenbein, W.; Lang, W. Preparation of 2-Chloro-1-cycloalkene-1-carboxylic Acids and Their Hydrolysis to αω -Dicarboxylic Acids. Chem. Ber. 1960, 93, 2743-2749.
33. Mizuno, A.; Hamada, Y.; Shioiri, T. New Methods and Reagents in Organic Synthesis; 6. A Simple One-Pot Conversion of Primary Alcohols to Nitriles Having One C-Atom More. Synthesis 1980, 1007-1009
34. Tutwiler, G. F.; Kirsch, T.; Mohrbacher, R. J.; Ho, W. Pharmacologic Profile of Methyl 2-Tetradecylglycidate (McN-3716). An Orally Effective Hypoglycemic Agent. Metabolism 1978, 27, 1539-1556.
35. Lee, S. M. The Effect of Chronic α-Glycosidase Inhibition of Diabetic Nephropathy, in the db/db Mouse. Diabetes 1982, 31, 249-254.
36. Ortlepp, I.; Gaertner, K.; Schoetz, H.; Zogbaum, A. Chronic Phlorizin Intoxication in Adipose Mutant Mice C57BL/KS db/db and in Normal Controls. In New Developments in Biosciences: Their Implications for Laboratory Animal Science; Beynen, A. C., Solleveld, H. A., Eds.; Martin Nijhoff: Dordrecht, 1988; pp 359-363
37. Hanson, R. L.; Ho, R. S.; Wise berg, J. J.; Simpson, R.; Younathan, E. S.; Blair, J. B. Inhibition of Gluconeogenisis and Glycogenolysis by 2,5-Anhydro-D-mannitol. J. Biol. Chem. 1984, 259, 218-223
38. Chapman, N. B.; Clarke, K.; Humphries, A. J.; Saraf, S. U.-D. Pharmacologically Active Benzo[b]thiophene Derivatives. Part VII. Analogues of Tryptamine and Heteroauxin. J. Chem. Soc. C 1969, 1612-1616
39. Mndzhoyan, A. L.; Aroyan, A. A. Benzofuran Derivatives. VII. Chloromethylation of Benzofuran and 2-Methyl-2,3-dihydrobenzofuran and Some Transformations of the Products. Isv. Akad. Nauk SSSR, Ser. Khim. 1961, 14, 591-601.
40. Bell, F.; Spanswick, J. Some Derivatives of Indan-1-one. J. Chem. Soc. C 1966, 1887-1888.
41. Caldwell, J.; Mitchell, S. C. Metabolic Pathways. In Comprehensive Medicinal Chemistry; Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford, 1990; Vol. 5, pp 144-145
42. Sohda, T.; Momose, Y.; Meguro, K.; Kawamatsu, Y.; Sugiyama, Y.; Ikeda, H. Studies on Antidiabetic Agents. Synthesis and Hypoglycemic Activity of 5-[4-(pyridylalkoxy)benzyl]-2,4-thiazolidinediones. Arzneim.-Forsch. 1990, 40, 37-42
43. 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. 1989, 32, 421-428
44. Coleman, D. L.; Hummel, K. P. Studies with the Mutation, Diabetes, in the Mouse. Diabetologia 1967, 3, 238-248
45. Armarego, W. L. F. The Synthesis of 5,7-Dichlorocoumaran-3-one and Related Problems. Aust. J. Chem. 1960, 13, 95-102.
46. Cagniant, P.; Kirsch, G. Method for the Synthesis of Mono-or Polysubstituted 3(2H)-Benzofuranones and Benzo[b]furans. C. R. Acad. Sci.; Ser. C 1976, 282, 993-996.
47. Schroeder, D. C.; Corcoran, P. O.; Holden, C. A., Mulligan, M. C. Benzofuro[3,2-b]indoles. J. Org. Chem. 1962, 27, 586-591.
48. Koyama, T.; Takashi, H.; Yamato, M.; Kohki, S. Reactions of Benzylcarbonyl Compounds with Formamide. IX. α-Acyl-5,6,7,8-tetrahydro-2-naphthylacetonitriles. Yakugaku Zasshi 1973, 93, 1536-153