Back to results
US 2024/0425544 A1Published application
Stereoselective steroidal reductions
AssigneeSandhill One, LLC
InventorsJ Gregory REID, Jayachandra P REDDY, SK Samad HOSSAIN
Life of this patent
Estimating the term…
Abstract
Methods of making steroids, and to 5β stereoselective reductions of steroids to produce the same.
Claims45
1) A method of reducing a 4,5-double bond on 3-ketochol-4-enoic acid (KCEA) or a derivative thereof defined by Formula I, to preferentially give a 5f-product, comprising contacting the compound of Formula I:
- with a Pd catalyst in a solvent or solvent mixture comprising at least 10% of pyridine or a substituted pyridine, thereby producing the compound of Formula II:
- wherein:
- a) A and B are OH and H respectively, H and OH respectively, H and H, or 7-oxo in combination;
- b) X is C(O)OR1 or C(O)NR1R2;
- and
- c) R1 and R2 are independently hydrogen, a counterion when the compound is a carboxylate or amide salt, optionally substituted C1-20 alkyl, or optionally substituted aryl.
3 more elements
24) A method of reducing a 4,5-double bond on (20S)-21-hydroxy-20-methylpregn-4-en-3-one (BA) or a derivative thereof defined by Formula III, to preferentially give a 5β-product, comprising contacting the compound of Formula III:
- with a Pd catalyst in a solvent or solvent mixture comprising at least 10% pyridine or a substituted pyridine, thereby producing the compound of Formula IV:
- wherein:
- a) A and B are OH and H respectively, H and OH respectively, H and H, or 7-oxo in combination;
- and
- b) X is hydrogen or a protecting group.
2 more elements
44) A compound of Formula IV:
- wherein:
- a) A is OX;
- b) B is H;
- and
- c) each X independently forms OH or a protected OH, such as an ester, an ether, a silyl ether or an acetal,
- or a salt thereof.
3 more elements
Dependencies are inferred from the claim text.