Synthesis and biological activity of the metabolites of diethyl 4-[(4-bromo-2-cyanophenyl)carbamoyl]benzylphosphonate (NO-1886)

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 3, 1996, Pages 547-551

  Goto, Kiyoto ^a   Nakamura, Shizuo ^a   Morioka, Yujiro ^a   Kondo, Mitsuyoshi ^a   Naito, Shinsaku ^a   Tsutsumi, Kazuhiko ^a  

^a OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Diethyl 4 (4 bromo 2 cyanophenyl)carbamoyl benzylphosphonate; Lipoprotein lipase activity; Metabolite; Synthesis; Triton WR 1339

Indexed keywords

4 [(4 BROMO 2 CYANOPHENYL)CARBAMOYL]BENZYLPHOSPHONIC ACID DIETHYL ESTER; DRUG METABOLITE; LIPOPROTEIN LIPASE; PHOSPHONIC ACID DERIVATIVE; TYLOXAPOL; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; DRUG ACTIVITY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HYPERTRIGLYCERIDEMIA; INTRAVENOUS DRUG ADMINISTRATION; MALE; NONHUMAN; RAT;

ANIMALS; BENZAMIDES; BIOTRANSFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENZYME INHIBITORS; HYPERLIPIDEMIAS; LIPOPROTEIN LIPASE; MAGNETIC RESONANCE SPECTROSCOPY; MALE; ORGANOPHOSPHORUS COMPOUNDS; POLYETHYLENE GLYCOLS; RATS; RATS, SPRAGUE-DAWLEY; TRIGLYCERIDES;

EID: 0029988865     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.547     Document Type: Article

References (12)

1. Tsuda Y., Tsuda Y., Japan. Patent 61151199 [Chem Abstr., 106, 67489 (1987)].
2. Tsutsumi K., Inoue Y., Shima A., Iwasaki K., Kawamura M., Murase T., J. Clin Invest., 92, 411-417 (1993).
3. Tsutsumi K., Inoue Y., Shima A., Murase T., Diabetes, 44, 414-417 (1995).
4. Goto K., Morioka Y., Kanamitsu S , Tsutsumi K., Naito S., Abstracts of Papers, 10th Annual Meeting of the Japanese Society for the Study of Xenobiotics, Oomiya, November 1995, p. 412.
5. Hardy W. B., Scalera M., J. Am. Chem. Soc., 74, 5212-5214 (1952).
6. 3CN: solvent flow rate, 1.2ml/min; detection at 260 nm.
7. Shortly afterward, the structure of 2 was confirmed by an X-ray crystallographic analysis (Fig. 2).
8. Thompson M J., Zeegers P. J., Tetrahedron, 46, 2661-2647 (1990).
9. Bollenback G. N., Long J. W., Benjamin D. G., Lindquist J. A., J. Am. Chem. Soc., 77, 3310-3315 (1955).
10. Rogers G. T., Ulbricht T. L. V., Tetrahedron Lett., 1968, 1029-1032.
11. Breuer E., Safadi M., Chorev M., Gibson D., J. Org. Chem., 55, 6147-6153 (1990).
12. Sochotz M. C., Scanu A., Page I. H., Amer. J. Physiol., 188, 399-402 (1957).