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US 10,472,384 B2Granted
Methods for the purification of deoxycholic acid
AssigneeAllergan Sales, Inc.
InventorsRobert M. Moriarty, Achampeta Rathan Prasad, John Gregory Reid, Roy A. Swaringen, Jr.
Life of this patent
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Abstract
Synthetic methods for preparing deoxycholic acid and intermediates thereof, high purity synthetic deoxycholic acid, compositions and methods of use are provided. Also, provided are processes for the synthesis of 12-keto or 12-α-hydroxysteroids from Δ-9,11-ene, 11-keto or 11-hydroxy-β-steroids. This invention is also directed to novel compounds prepared during the synthesis. This invention is also directed to the synthesis of deoxycholic acid starting from hydrocortisone.
Claims8
A process for preparing a compound of formula 1:
- the process comprising contacting Δ-9,11-ene compound 4:
- with an alkylhydroperoxide of the formula (R3)(R4)(R5)C—O—OH in the presence of a co-oxidant,
- wherein
- Pg is a hydroxyl protecting group,
- R is hydrogen, hydroxyl, or —OPg, R1 is the 17-side chain of a bile acid selected from the group consisting of cholic acid, deoxycholic acid, taurocholic acid, and glycocholic acid, wherein the carboxyl functionality of said side chain is optionally esterified with a C1-C6 alkyl group, and R2 is hydrogen, or R1 and R2 together with the carbon atom attached thereto form a keto or a keto protecting group, and
- each of R3, R4 and R5 is independently C1-C3 alkyl.
3 more elements
Dependencies are inferred from the claim text.