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US 12,221,411 B2Granted
Processes and intermediates for the preparation of carbaprostacyclin analogues
AssigneeChirogate International Inc.
InventorsChun-Yu Lin, Tzyh-Mann Wei, Shih-Yi Wei
Life of this patent
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Abstract
The invention relates to processes for preparing carbaprostacyclin analogues and intermediates prepared from the processes. The invention also relates to cyclopentenone intermediates in racemic or optically active form.
Claims17
A racemic or optically active compound of Formula 1:
- wherein Y is —CH2OP or —COOR1;
- X is F, Cl, Br, I, or —OTs;
- P is H or a hydroxyl protective group;
- and R1 is C1-7-alkyl, aryl or aralkyl, each of which is unsubstituted or substituted by C1-4-alkyl, C2-7-alkenyl, C2-7-alkynyl, nitro, halogen or alkoxy.
1 more element
A process for preparing a compound of Formula (R)-1 enriched in the (R)-enantiomer and having an optical purity of at least 95% enantiomeric excess,
- wherein Y is —CH2OP or —COOR1;
- X is F, Cl, Br, I, or —OTs;
- P is H or a hydroxyl protective group;
- and R1 is C1-7-alkyl, aryl or aralkyl, each of which is unsubstituted or substituted by C1-4-alkyl, C2-7-alkenyl, C2-7-alkynyl, nitro, halogen or alkoxy, the process comprising the steps of:
- (1) enantioselectively (R)-esterifying a compound of Formula 1:
- wherein Y and X are as defined above, with an acyl donor of Formula D:
- wherein R4 and R5 are independently H or C1-6 alkyl, and a first lipase, to form a (R)-ester of Formula (R)-1b′ and an unreacted (S)-alcohol of Formula (S)-1:
- (2) removing the unreacted (S)-alcohol;
- and
- (3) deacylating the resultant (R)-ester.
7 more elements
Dependencies are inferred from the claim text.