Phosphorus-containing squalene synthetase inhibitors

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...

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558134, 558155, 562 21, A61K 3166, C07F 940

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active

048717215

ABSTRACT:
Compounds which are useful as inhibitors of cholesterol biosynthesis and thus as hypocholesterolemic agents are provided which have the structure ##STR1## Z is --(CH.sub.2).sub.n -- or --(CH.sub.2).sub.p --CH.dbd.CH--(CH.sub.2).sub.m --, wherein n is 1 to 5; p is 0, 1 or 2; m is 0, 1 or 2;

REFERENCES:
Poulter, C. D., et al., Biosynthesis of Isoprenoid Compounds, "Conversion of Farnesyl Pyrophosphate to Squalene", vol. 1, Chapter 8, pp. 413-441, J. Wiley and Sons, 1981.
Faust, J. R. et al. Proc. Nat. Acad Sci., U.S.A., "Squalene Synthetase Activity in Human Fibroblasts: Regulation via the Low Density Lipoprotein Receptor", 1979, 76, 5018-5022.
de Montellano, P. Ortiz et al., J. Med. Chem., "Inhibition of Squalene Synthetase by Farnesyl Pyrophosphate Analogues", 1977, 20, 243-249.
Corey and Volante, J. Am. Chem. Cos. "Application of Unreactive Analogs of Terpenoid Pyrophosphates to Studies of Multistep Biosynthesis, Demonstration that `Presqualene Pyrophosphate' is an Essential Intermediate on the Path to Squalene", 1976, 98, 1291-3.
Sandifer, R. M. et al., J. Am. Chem. Soc., 1982, 104, 7376-8, "Squalene Synthetase, Inhibition by an Ammonium Analogue of a Carbocationic Intermediate in the Conversion of Presqualene Pyrophosphate to Squalene".
Bertolino, A. et al., Biochim. Biophys. Acta., 1978, 530, 17-23, "Polyisoprenoid Amphiphilic Compounds as Inhibitors of Squalene Synthesis and Other Microsomal Enzymes".
Poulter, C. D. et al., J. Org. Chem., 1986, 51, 4768-4779, "Phosphorylation of Isoprenoid Alcohols".
Poulter, C. D. et al., J.A.C.S., 1987, 109, 5542, "Methane and Difluoromethanediphosphonate Analogues of Geranyl Diphosphate: Hydrolysis-Inert Alternate Substrates".
McClard, R. W. et al., J. Am. Chem. Soc., 1987, 109, 5544-5545, "Novel Phosphonylphosphinyl (P-C-P-C) Analogues of Biochemically Interesting Diphosphates, Syntheses and Properties of P-C-P-C Analogues of Isopentenyl Diphosphate and Dimethylallyl Diphosphate".
Capson, Phd Dissertation, Jun. 1987, Dept. of Med. Chem. Univ., Utah, Abstract, Table d Contents, pp. 16, 17, 40-43, 48-51, Summary.

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