Process for stereoselective synthesis of prostacyclin...

Details Process for stereoselective synthesis of prostacyclin... Process for stereoselective synthesis of prostacyclin...

2003-08-27

2004-10-26

Richter, Johann (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C568S630000, C568S657000, C568S813000

Reexamination Certificate

active

06809223

ABSTRACT:

FIELD OF THE INVENTION
The present application relates to a shortened process for producing prostacyclin derivatives and novel intermediate compounds useful in the process. The present application also relates to stereoselectively produced compounds prepared by the inventive process. Furthermore, the prostacyclins produced in this process are pure diastereomers, i.e., >99%.
BACKGROUND OF THE INVENTION
Prostacyclin derivatives are useful pharmaceutical compounds possessing activities such as platelet aggregation inhibition, gastric secretion reduction, lesion inhibition, vasodilation and bronchodilation.
For convenience, the novel prostacyclin derivatives will be referred to by the trivial, art-recognized system of nomenclature described by N. A. Nelson, J. Med. Chem. 17:911 (1974) for prostaglandins. Accordingly, all of the novel prostacyclin derivatives herein will be named as 9- deoxy-PGF
1
-type compounds.
U.S. Pat. No. 4,306,075 discloses methods for making prostacyclin derivatives. However, these and other known processes involve a large number of steps. It is an object of the present invention to provide an improved method of preparing prostacyclin derivatives involving fewer steps.
SUMMARY OF THE INVENTION
The present invention relates to a process for preparing 9-deoxy-PGF
1
-type compounds by a process that is stereoselective and requires fewer steps than the prior art. The invention also relates to novel intermediates prepared during the synthesis of the 9-deoxy-PGF
1
-type compounds. Furthermore, the invention relates to 9-deoxy-PGF
1
-type compounds prepared by the inventive process.


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