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US 9,346,738 B2Granted
Process for the preparation of treprostinil and derivatives thereof
AssigneeSciPharm SaRL
InventorsNareshkumar Jain, Michael Kirkup, Michael Marella, Sanjeevani Ghone
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Abstract
A method for the preparation of treprostinil and its derivatives is described. In contrast to prior art, this method utilizes an easily scalable enzymatic resolution of a key intermediate for making these compounds. Another significant improvement of the described method over prior methods is the regioselective Claisen rearrangement of a 5-allyloxy-benzaldehyde precursor, which is facilitated by a bromo substituent in 2-position.
Claims17
A compound of the following formula I or formula II:
- wherein:
- X is Br and Y is H;
- PG1 is selected from the group consisting of methyl, methoxymethyl, benzyloxymethyl, methoxyethoxymethyl, benzyl, 4-methoxybenzyl, 2,6-dichlorobenzyl, 3,4-dichlorobenzyl, —CH2COOH, —CH2COORx, and —CH2CH2OPG2;
- PG2 is tert-butyl-dimethylsilyl (TBDMS), tetrahydropyran (THP), SiR1R2R3, or —CH2ORx;
- Ra is hydrogen, hydroxy —ORx, —OCOORx, —OSO2Rx, Cl, Br, F, I, —SRx, or —SO2Rx;
- and
- Rx is C1-4alkyl or aryl.
4 more elements
Dependencies are inferred from the claim text.