Process for the production of oxandrolone

Details Process for the production of oxandrolone Process for the production of oxandrolone

2006-03-07

2006-03-07

Aulakh, Charanjit S. (Department: 1625)

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

Organic compounds

Cyclopentanohydrophenanthrene ring system containing

C549S243000

Reexamination Certificate

active

07009063

ABSTRACT:
The present invention relates to a process for the synthesis of oxandrolone from mestanolone. The process comprises the steps of: (a) oxidizing mestanolone to form 17β-hydroxy-17α-methyl-5α-androst-1-en-3-one; (b) hydroxylating the 17β-hydroxy-17α-methyl-5α-androst-1-en-3-one to form 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one; (c) cleaving the 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one to form 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid; and (d) reducing the 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid to form oxandrolone.

REFERENCES:
patent: 2260328 (1941-10-01), Miescher et al.
patent: 2305602 (1942-12-01), Butenandt et al.
patent: 2879279 (1959-03-01), Burg
patent: 3101349 (1963-08-01), Pappo et al.
patent: 3109016 (1963-10-01), Nysted et al.
patent: 3128283 (1964-04-01), Pappo et al.
patent: 3246014 (1966-04-01), Jung et al.
patent: 3280133 (1966-10-01), Pappo et al.
patent: 3282962 (1966-11-01), Pappo et al.
patent: 3644342 (1972-02-01), Chorvat et al.
patent: 3666775 (1972-05-01), Uskokovic
patent: 3673217 (1972-06-01), Uskokovic
patent: 3761503 (1973-09-01), Uskokovic
patent: 3761504 (1973-09-01), Uskokovic
patent: 3843685 (1974-10-01), Uskokovic et al.
patent: 3956316 (1976-05-01), Uskokovic et al.
patent: 4097678 (1978-06-01), Kerb et al.
patent: 4328162 (1982-05-01), Hyatt et al.
patent: 4376733 (1983-03-01), Frimer
patent: 4434080 (1984-02-01), Barton et al.
patent: 5510538 (1996-04-01), Frigerio et al.
patent: 6211363 (2001-04-01), Terasawa et al.
patent: 6583298 (2003-06-01), Santa et al.
patent: 6787659 (2004-09-01), Desai et al.
patent: 2003/0032817 (2003-02-01), Cabaj et al.
patent: 2003/0109721 (2003-06-01), Desai et al.
patent: WO 98/24452 (1998-06-01), None
patent: 0114348 (2001-03-01), None
patent: WO 02/100881 (2002-12-01), None
Bi, H., et al., “Studies on anabolic steroids. 9. Tertiary sulfates of anabolic 17 α-methyl steroids: synthesis and rearrangement”,Steroids, Structure, Function, and Regulation, (Butterworth-Heinemann) 57(7): 306-312, 1992.
Carey, F. A., et al., “Part B: Reactions and Synthesis, Oxidations”,Advanced Organic Chemistry, Chapter 12, (Plenum Press) 3: 625-626, 1990.
Counsell, R. E., et al., “Anabolic Agents. Derivatives of 5α-Androst-1-ene”,J. Organic Chem., (The Am. Chem. Soc.)27(1): 248-253, 1962.
Nicolaou, K. C., et al., “A New Method for the One-Step Synthesis of αxβ-Unsaturated Carbonyl Systems from Saturated Alcohols and Carbonyl Compounds”,J. Am. Chem. oc., (Am. Chem. Soc.)122: 7596-7597, 2000.
Pappo, R. and Jung, C. J., “2-Oxasteroids: A New Class of Biologically Active Compounds”,Tetrahedron Letters, (Pergamon Press Ltd) 9: 365-371, 1962.
Pelc, B, “Steroid-Derivatives, XXIV.*, The Preparation of 17α-Methylandrost-1-EN-17β-OL-3-One”,Collection of Czechoslovak Chemical Communications, (Czechoslovak Academy of Sciences) 29(4): 1029-1034, 1964.
Schänzer, W., et al., “17-Epimerization of 17 α-methyl anabolic steroids in humans: metabolism and synthesis of 17 α-hydroxy-17 β-methyl steroids”,Steroids, (Butterworth-Heinemann) 57(11): 537-550, 1992.

Affiliated with

Also associated with

Rating

Process for the production of oxandrolone does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the production of oxandrolone, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the production of oxandrolone will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3541929