Prostacyclin derivatives

Details Prostacyclin derivatives Prostacyclin derivatives

2002-02-15

2003-03-04

Richter, Johann (Department: 1621)

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

Organic compounds

Oxygen containing

C568S379000, C560S121000, C562S503000

Reexamination Certificate

active

06528688

ABSTRACT:

FIELD OF THE INVENTION
The present application relates to a process for producing prostacyclin derivatives and novel intermediate compounds useful in the process.
BACKGROUND OF THE INVENTION
Prostacyclin derivatives are useful pharmaceutical compounds possessing activities such as platelet aggregation inhibition, gastric secretion reduction, lesion inhibition, 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.


REFERENCES:
patent: 4306075 (1981-12-01), Aristoff
patent: 5153222 (1992-10-01), Tadepalli et al.
patent: 0 087 237 (1983-08-01), None
patent: 98/39337 (1998-09-01), None
Belch et at, “Randomized, Doubled-Blind, Placebo-Controlled Study Evaluating the efficacy and Safety of AS-013, a Prostaglandin E1Prodrug, in Patients With Intermittent Claudication,” Circulation, vol. 95, No. 9, American Heart Association Inc., pp. 2298-2302; May 6, 1997.
Nelson, “Prostaglandin Nomenclature,” Journal of Medicinal Chemistry, vol. 17, No. 9, American Chemical Society, pp. 911-918, Sep. 1974.
Takano et al., “Enantiodivergent Synthesis of Both Enantiomers of Sulcatol and Matsutake Alcohol from (R)-Epichlorohydrin,” Chemistry Letters, The Chemical Society of Japan, pp. 2017-2020, 1987.
Mathre et al., “A Practical Enantioselective Synthesis of &agr;,&agr;-Diaryl-2- Pyrrolidinemethanol, Preparation and Chemistry of the Corresponding Oxazaborolidines,” J. Org. Chem., vol. 56 No. 2, American Chemical Society, pp. 751-752, 1991.
Pagenkopf, “Substrate and Reagent Control of Diastereoselectivity in Transition Metal-Mediated Process: Development of a Catalytic Photo Promoted Pauson-Khand Reaction,” Caplus 1999, Abstract XP-002097925.
Mulzer et al., “Asymmetric Synthesis of Carbacycin Precursors by Pauson-Khand Cyclization,” Liebigs Ann. Chem., vol. 9, pp. 891-897, 1988, XP-002097924.
Khand et al., “Organocobalt Complexes. Part II. Reaction of Acetylenehexacarbonyldicobalt Complexes, (R1C2R2)Co2(CO)6, with Norbornene and its Derivatives,” J. Chem. Soc., J.C.S. Perkin I., pp. 977-981, 1963.
Pauson, “A Convenient and General Route to a Wide Range of Cyclopentenone Derivatives,” Tetrahedron, vol. 41, No. 24, Pergamon Press Ltd., pp. 5855-5860, 1985.
Schore, “Transition-Metal-Medicated Cycloaddition Reactions of Alkynes in Organic Synthesis,” Chem. Rev., vol. 88, American Chemical Society, pp. 1081-1119, 1988.
Shambayati et al., “N-Oxide Promoted Pauson-Khand Cyclizations at Room Temperature,” Tetrahedron Letters, vol. 31 No. 37, Pergamon Press, pp. 5289-5292, 1990.
Jeong et al., “Catalytic Version of the Intramolecular Pauson-Khand Reaction,” J. Am. Chem. Soc., vol. 116, American Chemical Society, pp. 3159-3160, 1994.
Chung et al., “Promoters for the (Alkyne) hexacarbonyldicobalt-Based Cyclopentenone Synthesis,” Organometallics, vol. 12, American Chemical Society, pp. 220-223, 1993.
Hicks et al., “A Practical Titanium-Catalyzed Synthesis of Bicyclic Cyclopentenones and Allylic Amines,” J. Org. Chem., vol. 61 No. 8, pp. 2713-2718, 1996.
Zhang et al. “A Nickel(O)-Catalyzed Process for the Transformation of Enynes to Bicyclic Cyclopentenones,” J. Org. Chem., vol. 61 No 14, pp. 4498-4499, 1996.
Pagenkopf et al., “Photochemical Promotion of the Intramolecular Pauson-Khand Reaction. A New Experimental Protocol for Cobalt-Catalyzed [2+2+1] Cycloadditions,” J. Am. Chem. Soc., vol. 118 No. 9, American Chemical Society, pp. 2285-2286, 1996.

Affiliated with

Also associated with

Rating

Prostacyclin derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Prostacyclin derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Prostacyclin derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3076055