Phosphorus-containing squalene synthetase inhibitors, new interm

Details Phosphorus-containing squalene synthetase inhibitors, new interm Phosphorus-containing squalene synthetase inhibitors, new interm

1989-06-01

1990-05-08

Sutto, Anton H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Phosphorus esters

558207, C07F 938, C07F 942

Patent

active

049240242

ABSTRACT:
Compounds which are useful as inhibitors of cholesterol biosynthesis and thus as hypocholesterolemic agents are provided which have the structure ##STR1## wherein Q is ##STR2## or a bond; 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:
Araki et al., "Current Abstracts of Chemistry", vol. 103, Issue 1199, (1986), No. 394994.
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., USA, "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 Farnesvl Pyrophosphate Analogues", 1977, 20, 243-249.
Corey and Volante, J. Am. Chem. Soc., "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.
Sandifier, R. M. et al., J. Am. Chem. Soc., 1982, 104, 7376-8, "Squalene Synthetase, Inhibition by an Ammonium Analogue of a Carbocationic Intermeidate 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 Isophentenyl Diphosphate and Dimethylallyl Diphosphate".
Capson, T. L., PhD Dissertation, Jun. 1987, Dept. of Medicinal Chemistry, The University of Utah, Abstract, Table of Contents, pp. 16, 17, 40-43, 48-51, Summary.

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