Method of preparing intermediates for retroviral protease inhibi

Details Method of preparing intermediates for retroviral protease inhibi Method of preparing intermediates for retroviral protease inhibi

1997-05-08

1999-02-16

Dentz, Bernard

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

Organic compounds

Amino nitrogen containing

564223, 556412, 560 27, C07C21127

Patent

active

058722998

ABSTRACT:
A synthesis is described for intermediates which are readily amenable to the large scale preparation of hydroxyethylurea-based chiral HIV protease inhibitors. The method includes forming a diastereoselective epoxide or cyanohydrin from a chiral alpha amino aldehyde.

REFERENCES:
patent: H725 (1990-01-01), Gordon
patent: 4268688 (1981-05-01), Tinker et al.
patent: 4477441 (1984-10-01), Boger et al.
patent: 4514391 (1985-04-01), Gordon et al.
patent: 4548926 (1985-10-01), Matsueda et al.
patent: 4599198 (1986-07-01), Hoover
patent: 4616088 (1986-10-01), Ryona et al.
patent: 4668769 (1987-05-01), Hover
patent: 4668770 (1987-05-01), Boger et al.
patent: 4757050 (1988-07-01), Natarajan et al.
patent: 4963530 (1990-10-01), Hemmi et al.
patent: 4977277 (1990-12-01), Rosenberg et al.
patent: 4990669 (1991-02-01), Reetz et al.
patent: 5157041 (1992-10-01), Handa et al.
Ito et al., Chem. Pharm. Bull., vol. 23(12), pp. 3081-3087, 1975.
Stanfield et al., J. Org. Chem., vol. 46, pp. 4799-4800, 1981.
Roberts et al., Science, 248, 385 (1990).
Krohn et al., J. Med. Chem. 34, 3340 (1991).
Getman et al., J. Med. Chem., 36, 288 (1993).
Reetz et al., Tet. Lett., 30, 5425 (1989).
Sax, N.I., "Dangerous Properties of Industrial Materials", 6th Ed., Van Nostrand Reinhold Co., 1984, p. 443.
"Handbook of Reactive Chemical Hazards", 3rd Ed., Butterworths, 1985, p. 295.
Matterson et al., Synlett., 631 (1991).
Reetz et al., Angew. Chem. Int. Ed., 26, 1141-1143 (1987).
J.R. Parikh, J. Amer. Chem Soc., 89, 5505-5507 (1967).
Erickson et al., Science, 249:527-533 (1980).
Drugs of the Future, 1991, 16(3), 210-212.
Meek et al., Nature, 343:90-92 (1990).
Pept. Struct. Funct. Proc. AM. Prept. Sym. 8th ed. by V.J. Hunby and D.H. Rich, pp. 511-520 (1983).
McQuade et al., "A Synthesis HIV-1 Protease Inhibitor with Antiviral Activity Arrests HIV-Like Particle Maturation", Science, 274, 454 (1990).
Rosenberg et al., J. Med. Chem., 30, 1224-1228 (1987).
Sadhu et al., Tet. Lett., 27, 795 (1986).
Villieras et al., Tet. Lett., 25, 835 (1984).
Fittkau, J. Prakt. Chem. 315, 1037-1044 (1973.
Evans et al., J. Org. Chem., vol. 50, No. 23, 4615-24 (1985).
Michnick et al., Synlett, 9:631-2 (1991).
Reetz et al., Tet. Lett., vol. 29, No. 27, 3295-98 (1988).
Hoffman et al., J. Chem. Soc., Chem. Comun. (1991):195-196.
Gu et al., Chemistry Letters, (1992):1169-1172.
Luly et al., J. Org. Chem., 53 (1988):6109-6112.
Harada et al., Chem. Pharm. Bull., 37, (9):2570-2572 (1989).

Affiliated with

Also associated with

Rating

Method of preparing intermediates for retroviral protease inhibi does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method of preparing intermediates for retroviral protease inhibi, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of preparing intermediates for retroviral protease inhibi will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2063791