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US 2025/0197338 A1Published application
Syntheses of compounds useful for producing treprostinil
AssigneeUnited Therapeutics Corporation
InventorsHitesh Batra, Sri Harsha Tummala, Mark Farquharson
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Abstract
Provided are methods of producing compounds, which are useful in synthesizing prostacyclin derivatives, such as treprostinil.
Claims27
A method of synthesizing a compound of formula (1)
- the method comprising:
- reacting a compound of formula (8)
- with 3,5 dinitrobenzoyl
- chloride to form a compound of formula (9)
- and
- deprotecting the compound of formula (9) to form the compound of formula (1)
- wherein TMS is trimethylsilyl.
4 more elements
A method of synthesizing a compound of formula (1)
- the method comprising:
- reacting a compound of formula (10)
- with a compound of formula (11)
- to form a compound of formula (12)
- oxidizing the compound of formula (12) to form a compound of formula (13)
- enantioselectively reducing the compound of formula (13) to form a chiral compound of formula (14)
- and
- isomerizing the compound of formula (14) to form the compound of formula (1)
5 more elements
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A method of synthesizing treprostinil comprising:
- enantioselectively reducing a compound of formula (16)
- to form a compound of formula (17)
- in the presence of an enantioselective enzyme catalyst;
- and
- converting the compound of formula (17) into treprostinil (4)
- wherein R1 is a hydroxy protecting group —(CH2)nX;
- X being H, phenyl, —CN, —OR3 or COOR3;
- n being 1 to 3, R3 being an alkyl, a hydroxy protecting group or a substituted or unsubstituted benzyl group;
- and R2 is a hydroxy protecting group.
6 more elements
25-30. (canceled)
32-34. (canceled)
Dependencies are inferred from the claim text.