Process for preparing high purity allopregnanolone and intermediates thereof
AssigneeCrystal Pharma, S.A.U.
InventorsIvano MESSINA, Jesús Miguel IGLESIAS RETUERTO, Ana María ARES SACRISTÁN
Life of this patent
Estimating the term…
Abstract
The invention relates to an efficient and industrially applicable process for the preparation and purification of allopregnanolone and intermediates thereof without the assistance of column chromatography.
Claims20
-13. (canceled)
A process for preparing and purifying a 3-carboxylic ester of allopregnanolone which comprises:
- reacting isoallopregnanolone with a strong carboxylic acid having a pka≤3 under Mitsunobu conditions;
- precipitating the 3-carboxylic ester of allopregnanolone in a solvent system comprising water and an organic solvent;
- and
- recrystallizing the precipitate of the 3-carboxylic ester of allopregnanolone in a non-polar solvent.
A 3-carboxylic ester of allopregnanolone containing an amount of 5α-pregn-2-en-20-one of 0.5% or less.
Allopregnanolone containing an amount of 5α-pregn-2-en-20-one and 3α-hydroxy-5α,17α-pregnan-20-one, in total, of 0.15% or less.
A 3-carboxylic ester of allopregnanolone selected from:
- Pregnan-20-one, 3-(2,6-dinitrobenzoyloxy)-, (3α,5α)-,
- Pregnan-20-one, 3-(2,4-dinitrobenzoyloxy)-, (3α,5α)-,
- Pregnan-20-one, 3-(chloroacetyloxy)-, (3α,5α)-,
- Pregnan-20-one, 3-(dichloroacetyloxy)-, (3α,5α)-,
- Pregnan-20-one, 3-(trichloroacetyloxy)-, (3α,5α)-,
- Pregnan-20-one, 3-(fluoroacetyloxy)-, (3α,5α)-,
- Pregnan-20-one, 3-(difluoroacetyloxy)-, (3α,5α)-,
- Pregnan-20-one, 3-(2-nitrobenzoyloxy)-, (3α,5α)-, or
- Pregnan-20-one, 3-(cyanoacetyloxy)-, (3α,5α)-.
Dependencies are inferred from the claim text.