Process for the production of oxandrolone
AssigneeBarr Laboratories, Inc.
InventorsShaileshkumar Ramanlal Desai, David Wayne Ray, Jr., Yousry A. Sayed
Life of this patent
Estimating the term…
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.
Claims20
A process for the production of oxandrolone comprising the steps of:
- (a) oxidizing mestanolone using IBX 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 using osmium tetroxide to form 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one;
- (c) cleaving the 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one using sodium metaperiodate 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 using sodium borohydride followed by an acid treatment to form oxandrolone.
A process for the production of oxandrolone comprising 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.
A process for the production of oxandrolone comprising the steps of:
- (a) reacting mestanolone with IBX to form 17β-hydroxy-17α-methyl-5α-androst-1-en-3-one;
- (b) reacting the 17β-hydroxy-17α-methyl-5α-androst-1-en-3-one with osmium tetroxide and N-methylmorpholine N-oxide to form 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one;
- (c) reacting the 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one with sodium metaperiodate to form 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid;
- (d) forming oxandrolone from the 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid by reacting the 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid with sodium borohydride followed by an acid treatment comprising addition of hydrochloric acid.
A process for the production of oxandrolone comprising the steps of:
- (a) oxidizing mestanolone using IBX 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;
- wherein at least two by-products are formed in step (a) that are non-reactive to steps (b) and (c).
Dependencies are inferred from the claim text.