Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2009-08-11
2011-10-04
Carr, Deborah D (Department: 1622)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
Reexamination Certificate
active
08030514
ABSTRACT:
The present invention provides novel processes for the preparation of a cyclopentanone of Formula II and a lactone of Formula I, which are useful in the production of prostaglandins:wherein Z, R2, R3, X1, X2, and are as defined in the specification.The invention also provides novel enantiomerically enriched compounds.
REFERENCES:
patent: 4013695 (1977-03-01), Lin
patent: 4233231 (1980-11-01), Floyd et al.
patent: 4272629 (1981-06-01), Roberts
patent: 4983753 (1991-01-01), Floyd, Jr.
patent: 5359095 (1994-10-01), Resul
patent: 5661178 (1997-08-01), Chen et al.
patent: 6462081 (2002-10-01), Maruyama et al.
patent: 6586462 (2003-07-01), Burk et al.
patent: 6639111 (2003-10-01), Maruyama et al.
patent: 6710081 (2004-03-01), Narita et al.
patent: 2007/0166809 (2007-07-01), Yeh et al.
patent: 2007/0167641 (2007-07-01), Wei et al.
patent: 2008/0039637 (2008-02-01), Wei et al.
patent: 0 267 605 (1988-05-01), None
patent: 2033791 (1995-04-01), None
Patent Abstracts of Japan of 09020788 dated Jan. 21, 1997.
Corey, E.J. et al. “Total Synthesis of Prostaglandins F2aand E2the Naturally Occurring Forms”Journal of the American Chemical Society(1970) vol. 92, No. 2, pp. 397-398 XP-002386523.
Lai, S. et al. Enantioselective Synthesis of l2-epi-PGF2aand 12,15-diepi-PGF2a, J. Org. Chem. (1999) vol. 64, pp. 7213-7217 XP-002386524.
Database CA [Online] Chemical Abstract. Howard, C. et al. “Total Synthesis of (.+-.)-Prostaglandin E2 Methyl Ester . . . ”Journal of the Chemical Society, Perkin Transactions : Organic and Bio-Organic Chemistry(1981) vol. 7, pp. 2049-2054 XP-002386565 retrieved from STN.
Itoh, T. et al. “Simple Preparation of the Optically Active gamma-Hydroxy Vinylstannanes Using Lipase-Catalyzed Hydrolysis”Chemistry Letters(1991) vol. 2, pp. 217-218 XP-002386525.
Database Crossfire Beilstein. Tolstikov, G.A. et al. “Beilstein Institut zur Forderung der Chemischen Wissenschaften”Chem. Nat. Compd. (1985) vol. 21, No. 5, pp. 570-578 XP-002386566.
Tolstikov, G.A. et al. “Regio- and Stereoselective Hydrostannylation of 3-Hydroxy-4-phenoxy-1 . . . ”Synthesis(1986) vol. 6, pp. 496-499 XP-002386526.
Gooding, O.W. et al. “Triply Convergent Synthesis of15-(Phenoxymethyl) and 4,5-Allenyl Prostaglandins. Preparation of an Individual Isomer of Enprostil”J. Org. Chem. (1993) vol. 58, pp. 3681-3686 XP-002386527.
Database CA [Online] Chemical Abstract. Kalnins, A et al. “Total Synthesis and Properties of Prostaglandins XXVI. Alkylation of Bicyclic Dihydropyridazinones”Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija(1990) vol. 1, pp. 78-87 XP-002386567 retrieved from STN.
Database CA [Online] Chemical Abstract. Kalnins, A. et al. “Total Synthesis and Properties of Prostaglandins. X . synthesis of .gamma.-oxy . . . ”Zhurnal Organicheskoi Khimii(1988( vol. 24, No. 4, pp. 742-755 XP-002386568 retrieved from STN.
Database CA [Online] Chemical Abstract. Kudryashova, V.V. et al. “Synthesis of Methyl 3.alpha . . . ”Bioorganicheskaya Khimiya(1986) vol. 12, No. 4, pp. 848-854 XP-002386569 retrieved from STN.
Database CA [Online] Chemical Abstract. Sakhartova, O.V. et al. “Comparative Calculation of Retention Values in Chromatogrpahy of Cyclopentane Derivatives on Silica Gel”Zhurnal Analiticheskoi Khimii(1985) vol. 40, No. 5, pp. 872-880 XP-002386570 retrieved from STN.
Database CA [Online] Chemical Abstract. Marino, J.P. et al. “Stereocontrolleed Synthesis of Prostaglandins from Cyclopentadiene Monoepoxide”Journal of Organic Chemistry(1984) vol. 49, No. 26, pp. 5279-5280 XP-002386571 retrieved from STN.
Database CA [Online] Chemical Abstract. Sakhartova, O.V. et al. “Chromatogrpahy of Prostaglandins, Their Analogs and Intermediates . . . ”Latvijas PSR Zinatnu. . . (1983) vol. 5, pp. 556-563 XP-002386572 retrieved from STN.
Chen, S.L. et al. “Prostaglandins and Congeners. 19. Vinylstannanes: Useful Organometallic Reagents for the Synthesis of Prostaglandins and Prostaglandin Intermediates” J. Org. Chem. (1978) vol. 43, No. 18, pp. 3450-3454 XP-002386528.
March's Organic Chemistry, Reactions, Mechanisms, and Structures. 5thEd., N.Y., Wiley & Sons, Inc. (2001) p. 869.
Kalnins, et al. (Total synthesis and properties of prostaglandins) Zhurnal Organicheskoi Khimii (1988) 24(4) pp. 742-755.
Korics, et al. (Total synthesis of prostaglandins) Latvjas PSR Zinatnu Akademijas Vestis, Kimijas Serija (1987) (6) pp. 731-739.
Marino, et al. (Regio- and stereoselectivity of the reaction between cyanocuprates and cyclopentene epoxides. Application to the total synthesis of prostaglandins) Journal of Organic Chemistry (1987) 52(22) pp. 4898-4913.
Sakhatorva, et al. Zhurnal Analiticheskoi Khimii (1985) 40(5) pp. 872-880, or Loza, et al. , Jour or Chromatography A, 708 (1195) 231-243.
Petrukhina, et al. (The effect of new synthetic prostanoids on the aggregation activity of human platelets) Eksperimental'naya i Klinicheskaya Farmakologiya (1995) 58(6) 45-8.
Loza, et al. (Enantiomeric enrichment of partially resolved 4-hydroxy-2-carboxymethylcyclopentanone derivatives) Journal of Chromatography, A (1995) 708(2), 231-43.
Dikovskaya, et al (Synthesis of 11-deoxy-2,3,4,5, 6-pentanorprostaglandin E1 methyl ester) Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija (1989) (4) 451-7.
Mevh, et al. (Prostaglandin-like inhibitors of prostaglandin H synthase) Bioorganicheskaya Khimiya (1989) 15(10) 1334-40.
Green, et al. Protective Groups in Organic Chemistry, 3rdEd. I J. Wiley & Sons (1999) Ch. 1, pp. 1-21.
Wei Shih-Yi
Yeh Yu-Chih
Carr Deborah D
Chirogate International Inc.
Ladas & Parry LLP
LandOfFree
Processes and intermediates for the preparations of... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Processes and intermediates for the preparations of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Processes and intermediates for the preparations of... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4283522