Process for preparing synthetic prostacyclins
First Claim
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1. A method for preparing a synthetic prostacyclin or a synthetic intermediate thereof, wherein the method comprises contacting an aldehyde with an enantiomerically pure phosphonate in a Horner-Emmons reaction to provide an alkene,wherein the enantiomerically pure phosphonate has a structure:
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Abstract
The presently disclosed subject matter provides methods of preparing synthetic prostacyclin analogs, including Beraprost, either as racemic mixtures or as single stereoisomers. Also provided are novel synthetic intermediates for use in these methods.
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Citations
19 Claims
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1. A method for preparing a synthetic prostacyclin or a synthetic intermediate thereof, wherein the method comprises contacting an aldehyde with an enantiomerically pure phosphonate in a Horner-Emmons reaction to provide an alkene,
wherein the enantiomerically pure phosphonate has a structure:
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13. A method for preparing a synthetic prostacyclin or synthetic intermediate thereof, wherein the method comprises:
(a) providing a compound of formula (V), (V′
) or (V″
);
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14. A method for producing a compound of formula (V), wherein the method comprises:
(a) coupling compound A;
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15. A method for preparing a synthetic prostacyclin or synthetic intermediate thereof, wherein the method comprises the use of a synthetic intermediate of formula (V), (V′
- ), or (V″
) or a hydroxyl group deprotected derivative thereof, wherein formulas (V), (V′
), and (V″
) are;
- ), or (V″
-
16. A compound of formula (V), (V′
- ), or (V″
) or a hydroxyl group deprotected derivative thereof, wherein formulas (V), (V′
), and (V″
) are;
- ), or (V″
-
17. A method for preparing an intermediate for a synthetic prostacyclin, wherein the method comprises contacting compound A:
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18. A compound of formula (XIV), (XIV′
- ), or (XIV″
);
- ), or (XIV″
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19. A method of preparing a synthetic prostacyclin, wherein the method comprises alkylating a compound of formula (XIV), (XIV′
- ), or (XIV″
).
- ), or (XIV″
Specification