Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Patent
1997-07-31
2000-01-11
Shaver, Paul F.
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C07F 708
Patent
active
060138238
ABSTRACT:
Analogs of the prostaglandin PGE.sub.1 are disclosed. These compounds exhibit uterotonic properties, enhancing the response to PGF.sub.2 .alpha. in isolated rat uteri. The compounds also exhibit other pharmacological properties, as inhibitors of gastric acid secretion, hypotensives, and bronchodilators. Processes for making the analogs, useful intermediates, and pharmaceutical preparations are also presented.
REFERENCES:
patent: 4190597 (1980-02-01), Floyd, Jr. et al.
patent: 4529812 (1985-07-01), Collins et al.
patent: 4617411 (1986-10-01), Collins et al.
patent: 5166174 (1992-11-01), Ueno et al.
patent: 5705659 (1998-01-01), Park et al.
D. van Dorp, Recent Developments in the Biosynthesis and The Analyses of Prostaglandins, Unilever Research Laboratories Vlaardingen, The Netherlands, Annals New York Academy of Sciences, Editors, pp. 182-199.
Gilman, A.G. et al. (Eds.), The Pharmacological Basis of Therapeutics, 8th Edition, 1990, Chp. 24, pp. 600-617, 911, 937-939.
Von Priv.-Doz. Dr. H. Schmidbaur und cand. chem. Brunhilde Armer, Organogallogermoxane--Verbindungen mit der Struktureinheit Ga-O-Ge, Angew. Chem. 78 Jahrg, 1966, Nr. 5, pp. 305-306.
Sih, C.J., et al., Total Synthesis of (.+-.)-15-Deoxyprostaglandin E.sub.1, J.C.S. Chem. Comm., 1972, pp. 240-241.
Sammes, P.G., et al., On the Synthesis of Azetidines from 3-Hydroxypropylamines, J. Chem, Soc., Chem, Commun., 1983; pp. 682-684.
Ali, S.M., et al., Synthesis of Prostaglandin A.sub.2 from 3-endo-Bromotricyclo [3.2.0.0.sup.2.7 ] heptan-6-one, J.C.S. Chem. Comm., 1980, pp. 74-75.
Ali, S.M., et al., Synthesis of 9-Deoxa-9, 10-dehydroprostaglandin-D.sub.2 through Reaction of 2-Oxatricyclo[3.3.0.0.sup.4 6 ] oct-7-en-3-one with a Cuprate Reagent, J.C.S. Chem. Comm. 1979, pp. 679-680.
Brown, E.A., et al., A Short Synthesis of Prostaglandins from 5-Chloro-5-cyano-7-syn-formylbicyclo[2,2,1]hept-2-ene, J.C.S. Chem. Comm. 1975, p. 39.
Dawson, M.J., et al., Reduction of Bicyclo [3.2.0]hept-2-en-6-one with Dehydrogenase Enzymes in Whole Cell Preparations of some Fungi and Yeasts, J. Chem Soc. Perkin Trans. I, 1983, pp. 2119-2125.
Jones, G., et al., Stero-controlled Synthesis of Prostaglandin Synthons, J.C.S. Perkin I, 1974, pp. 1676-1683.
Miller, J.G., et al., Highly Stereoselective Total Syntheses of Prostaglandins via Sterospecific Sulfenate-Sulfoxide Transformations, J. Amer. Chem. Soc., 96:21, Oct. 16, 1974, pp. 6774-6775.
Trost, B.M., et al., New Synthetic Reactions.Oxidative Decarboxylation, J. Amer. Chem. Soc., 97:12, Jun. 11, 1975, pp. 3528-3530.
Corey, E.J., et al., Preparation of an Optically Active Prostaglandin Intermediate via Asymmetric Induction, pp. 6908-6909.
Sih, C.J., et al., Total Synthesis of Prostaglandins II. Prostaglandin E.sub.1, Communications to the Editor, J. Amer. Chem. Soc., 94:10, May 17, 1972, pp. 3643-3644.
Alvarez, F.S., et al., Synthesis of (.+-.)-Prostaglandin E.sub.1,(.+-.)-11-Deoxyprostaglandins E.sub.1, F.sub.1, and (.+-.)-9-Oxo-13-cis-Prostenoic Acid by Conjugate Addition of Vinylcopper Reagents, J. Amer. Chem. Soc. 94:22, Nov. 1, 1972, pp. 7823-7827.
Kluge, A.F., et al., Synthesis of Prostaglandin Models and Prostaglandins by Conjugate Addition of a Functionalized Organocopper Reagent, J. Amer. Chem. Soc., 94:22, Nov. 1, 1972, pp. 7827-7832.
Corey, E.J., et al., Efficient Generation of the 15S Configuration in Prostaglandin Synthesis, Attractive Interactions in Stereochemical Control of Carbonyl Reduction, J. Amer. Chem. Soc., 94:24, Nov. 29, 1972, pp. 8616-8618.
Roberts, S.M., et al., Factors Influencing the Regioselectivity of Reactions Involving Organocuprate Reagents and Allyl Acylates: Synthesis of Some Phenylthioprostanoids, J.C.S. Perkin I, 1981, pp. 1729-1733.
Iguchi, S, et al., Diisobutylaluminum 2,6-Di-t-butyl-4-methylphenoxide, Novel Stereoselective Reducing Atent for Prostaglandin Synthesis, Bull. Chem. Soc. Jpn., 54, 1981, pp. 3033-3041.
Noyori, R., Assymmetric Synthesis Via Axially Dissymmetric Molecules, A Binaphthol-Modified Complex Aluminum Hydride Reagent Possessing Extremely High Ability of Chiral Recognition, Pure & Appl. Chem., vol. 53, 1981, pp. 2315-2322.
Corey, E.J., et al., Stereo-Controlled Synthesis of Prostaglandins F.sub.2.alpha. and E.sub.2 (dl), J. Amer. Chem. Soc., 91:20, Sep. 24, 1969, pp. 5675-5677.
Corey, E.J., et al., Total Synthesis of Prostaglandins F.sub.1.alpha., E.sub.1, F.sub.2.alpha., and E.sub.2 (Natural Forms) from a Common Synthetic Intermediate, J. Amer. Chem. Soc., 92:8, Apr. 22, 1970, pp. 2586-2587.
Corey, E.J., et al., Studies on the Total Synthesis of Gibberellic Acids, A Simple Route to the Tetracarbocyclic Network, J. Amer. Chem. Soc., 92:2, Jan. 28, 1970, pp. 396-397.
Finch, M.A.W., et al., Synthesis of Prostaglandin A.sub.2 through Reaction of 3-endo-Bromo-tricyclo[3.20.0.sup.2.7 ]heptan-6-one with a Cuprate Reagent, J.C.S. Perkin I, 1981, pp. 1725-1728.
Chapleo, C.B., et al., Total Synthesis of Prostaglandin A.sub.2 involving the Reaction of a Heterocuprate Reagent with an Allyl Epoxide, J.C.S. Perkin I, 1980, pp. 2084-2087.
Horsewood, P., et al., Preparation and Dienophilic Reactions of Nitrosyl Cyanide, J.C.S. Perkin I, 1980, pp. 1587-1591.
Howard, C.C., et al., Total Synthesis of Prostaglandin-F.sub.2.alpha. involving Stereocontrolled and Photo-induced Reactions of Bicyclo[3.2.0]hepatones, J.C.S. Perkin I, 1980, pp. 852-857.
Lee, T.V., et al., Preparation and Some Reactions of 3-endo-Substituted Tricyclo[3 2.0.0.sup.2.7 ]heptan-6-ones, J.C.S. Perkin I, 1978, pp. 1179-1182.
Lee, T.V., et al., Total Synthesis of Prostaglandin-F.sub.2.alpha. through Homoconjugate Addition of an Organocuprate Reagent to a Tricyclo[3.2.0.0.sup.2.7 ]heptanone, J.C.S. Perkin I, 1978, pp. 1176-1178.
Brown, E.D., et al., The Acetoxyfulvene Synthesis of Prostaglandins. Part I. synthesis of the Corey Aldehyde, J.C.S. Perkin I, 1978, pp. 1507-1510.
Noyori, R., et al., A Highly Efficient Synthesis of Prostaglandin Intermediates Possessing the 15S Configuration, J. Amer. Chem. Soc., 101:19, Sep. 12, 1979, pp. 5843-5844.
Corey, E.J., et al ., New Reagents for Stereoselective Carbonyl Reduction. An Improved Synthetic Route to the Primary Prostaglandins, J. Amer. Chem. Soc., 93:6, Mar. 24, 1971, pp. 1491-1493.
Corey, E.J., et al., A New Method for the 1,4 Addition of the Methylenecarbonyl Unit (-CH.sub.2 CO-) to Dienes, J. Amer. Chem. Soc., 93:17, Aug. 25, 1971, pp. 4326-4327.
Spurlock, L.A., et al., The Nature of the Carbonium Ion. VII. The Dehydronorbornyl Cations from Thiocyanate Isomerizations, J. Amer. Chem. Soc., 93:1, Jan. 13, 1971, pp. 146-151.
House, H.O., et al., The Chemistry of Carbanions. XII. The Role of Copper in the Conjugate Addition of Organometallic Reagents, The Chemistry of Carbanions, XII, Oct. 1966, pp. 3128-3141.
Kluge, A.F., et al., Synthesis of 13-cis-Prostaglandins via a Highly Stereoselective Conjugate Addition with a Functionalized Organocopper Reagent, J. Amer. Chem. Soc., 94:26, Dec. 27, 1972, pp. 9256-9258.
Corey, E.J., et al., Mixed Cuprate Reagents of Type R.sub.1 R.sub.2 CuLi Which Allow Selective Group Transfer, J. Amer. Chem. Soc., 94:20, Oct. 4, 1972, pp. 7210-7211.
Corey, E.J., et al., Total Synthesis of Prostaglandins E.sub.2 F.sub.2.alpha. (dl) Via a Tricarbocyclic Intermediate, Tetrahedron Letters No. 4, 1978, pp. 307-310.
Just, G., et al., A Prostaglandin Synthesis, Tetrahedren Letters No. 22, 1967, pp. 2093-2097.
Cameron, A.G., et al., Total Synthesis of Prostaglandin D.sub.1 Methyl Ester and 9-EPI-Prostaglandin D.sub.1 Methyl Ester, Tetrahedron Letters vol. 23, No. 5, 1982, pp. 561-564.
K. Kiec-Kononowicz et al., Reaction of 5,5-diphenyl-2-thiohydantoin with 1,3-dibromopropane Under Phase Transfer Catalytic Conditions, Tetrahedron vol. 37, 1981, pp. 409-415.
Lish, P.M., et al., Pharmacology of Methdilazine (Tacaryl.sup.(R)), Arch int. pharmacodyn., CXXIX, No. 1-2, 1960, pp. 77-107.
Suzuki, M., et al., A General Synthesis of Primary Prostaglandins, Tetrahedron Letters, vol. 23, No. 52, 1982, pp. 5563-5566.
Nelson, N.A., Prostalandin Nomeclature, Journal of Medicinal Chemistry, 1974, vol. 17, No. 9, pp. 911-918.
Takano, S.
Buschi Carlos Alberto
Giarcovich Silvia Susana
Mamarella Carlos Alberto Genaro
New Pharma International Corp.
Shaver Paul F.
LandOfFree
Trans-pentavalent 2-15-deoxy-16-hydroxy-16-methyl-PGE1 methyl es does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Trans-pentavalent 2-15-deoxy-16-hydroxy-16-methyl-PGE1 methyl es, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Trans-pentavalent 2-15-deoxy-16-hydroxy-16-methyl-PGE1 methyl es will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1463682