Intermediates to carbocyclic nucleosides

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

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564497, C07C20962

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active

058409904

ABSTRACT:
The present invention relates to certain purine nucleoside analogues containing a carbocyclic ring ill place of trip sugar residue, salts, esters and pharmaceutically acceptable derivatives thereof, processes for there preparation, pharmaceutical formulations containing them, and to the use of such compounds in therapy, particularly the treatment of or prophylaxis of certain viral infections.

REFERENCES:
patent: 4543255 (1985-09-01), Shealy
patent: 4734194 (1988-03-01), Kalman et al.
patent: 5087697 (1992-02-01), Daluge
patent: 5206435 (1993-04-01), Daluge
patent: 5498625 (1996-03-01), Evans et al.
Dickman et al., "Reduction of a-Amino Acids: L-Valinol," Org. Syn. Coll. vol. VII, 1990, 530-533.
Price, "Inhibition of the replication of hepatitis B virus by the carbocyclic analogue of 2'-deoxyguanosine," Proc. Natl. Acad. Sci. USA vol. 86, Nov., 1989, 8541-8544.
Evans, "Synthesis of Either Enantiomer of cis-3-Aminocyclopentanecarboxylic Royal Society of Chemistry. Perkins Transaction 1, vol. 3, Mar. 1991, 656-657.
Dornsife et. al., "Anti-Human Immunodeficiency Virus Synergism by Zidovudine (3'-Azidothymidine) and Didanosine (Dideoxyinosine) Contrasts with Their Additive Inhibition of Normal Human Marrow Progenitor Cells," Antimicrob. Agents Chemother., 35, 1991, 322-328.
Katagiri et. al., "Synthesis of Nucelosides and Related Compounds. XXII..alpha. Carbocyclic Analogues of Thymidine and Related Compounds from 1682-1688.
Bennett et al., "Phosphorylation of the Carbocyclic Analog of 2'Deoxyguanosine in Cells Infected with Herpes Viruses," Biochemical Pharmacology, 1990, vol. 40, No. 7, 1515-1522.
Balzarini et al., "Carbocyclic 5-Iodo-2'-deoxyuridine (C-IDU) and Carbocyclic (E)-5-(2-Bromovinyl)-2'-deoxyuridine (C-BVDU) as Unique Examples of Chiral Molecules where the Two Enantiomeric Forms Are Biologically Active: Interaction of the (+) and (-)-Enantiomers of C-IDU and C-BVDU with the Thymidine Kinase of Herpes Simplex Virus Type 1", Molec. Pharm. 37, 1990, 395-401.
Bruckner et al., "Automated Enantioseparation of Amino Acids By Derivitization with 0-Phthaldialdehyde and N-Acylated Cysteines," J. Chom., 476, 1989, 73-82.
Biggadike et al., "Short Convergent Route to Homochiral Carbocyclic 2'-Deoxynucleosides and Carbocyclic Ribonucleosides," J. Chem. Soc. Chem Commun., 1987, 1083-1084.
Barton et al., "On the Mechanism of the Deoxygenation of Secondary Alcohols by the Reduction of Their Methyl Xanthates By Tin Hydrides," Tetrahedron, 42, 1986, 2329-2338.
Powell et al., "Lithium Aluminum Hydride Reductions: a New Hydrolysis Method for Intratable Products," Synthesis, 1986, 338-340.
Robins et al, Nucleic Acid Related Compounds 42. A General Procedure for the Efficient Deoxygenation of Secondary Alcohols. Regiospecific and Steroselective conversion of Ribonucleosides to 2'-Deoxynucleosides, J. Am. Chem. Soc., 105, 1983, 4059-4065.
Hartwig, "Modern Methods for the Radical Deoxygenation of Alcohols," Tetrahedron, 1983, 39, 2609-2645.
Barton, et al., "Radical-Induces Deoxygenation of Primary Alcohols," Synthesis, 1981, 743-745.
Oberg et al., "The Tetraisopropyldisiloxane-1,3-Diyl: A Versatile Protecting Group for the Synthesis of Adenylyl-2(2'.fwdarw.5')-Adenylyl-(2'.fwdarw.5')-Adenosine (2-5A Core)," Tetrahedron Letters 22, 1981, 1741-1744.
Robins et al., Smooth and Efficient Deoxygenation of Secondary Alcohols. A General Procedure for the Conversion of Ribonucleosides to 2' Deoxynucleosides, J. Am. Chem. Soc., 103, 1981, 932-933.
Verdegaal et al., "A Convient Synthesis of 2' O-acetal-N-acyl derivatives of riboguanosine," Recueil, 10, 1981, 200-204.
Markiewicz, "The Reaction of 1,3-Dichloro-1,1,3,3-Tetrisopropyldisoloxane With Some Open Chain Polyhydroxy Compounds," Tetrahedron Letters, 21, 1980, 4523-4524.
Markiewicz, "Tetraisoproipyldisiloxane-1,3-diyl, a Group for Simultaneous Protection of 3'-and 5'-Hydroxy Functions of Nucleosides," J.Chem.Research (S) 1979, 24-25.
Barton et al., "A new Method for the Deoxygenation of Secondary Alcohols," J.Chem.Soc., Perkin, 1975, 1574-1585.
Jagt et al., "Diels-Alder Cycloadditions of Sulfonyl Cyandines with J.Org. Chem., 39, 1974, 564-566.
Yamamoto and Maruoka, "Regioselective Carbonyl Amination using Diisobutylaluminum Hydride", J.Am.Chem.Soc, 14, 1981, 4186-4194.
Markiewicz et al., "The Reaction of 1,3-Dichloro-1,1,3,3-Tetraisopropyldisiloxane with Cytosine Arabinoside and 1-(6-Deoxy-.alpha.-L-Talofuranosyl)Uracil", Collection Czechoslov. Chem Commun., (English) vol. 45(6), 1980, 1860-1865.
Secrist III et al., "Resolution of Racemic Carbocyclic Analogues of Purine Nucleosides through the Action of Adenosine Deaminase. Antiviral Activity of the Carbocyclic 2'-Deoxyguanosine Enantiomers", J. Med. Chem., (30), 1987, 746-749.
Shealy et al, "Synthesis and Antiviral Activity of Carboyclcic Analogues of 2'-Deoxyribofuranosides of 2-Amino-6-substituted Purines and of 2-amino-6-substituted-8-azapurines," J.Med.Chem., 27, 1984, 1416-1421.
Schroder, "Osmium Tetroxide Cis Hydroylation of Unsaturated Substrates," Chem Rev. 1980 (80), 187-213.
VanRheenen et al., "An Improved Catalytic OsO.sub.4 oxidation of Olefins to Cis-1-2-Glycols Using Tertiary Amine Oxides as the Oxidant," Tetrahedron Letters, No. 3, 1976, 1973-1976.
Tyle, "Iontophoretic Devices for Drug Delivery," Pharmaceutical Research (3), 1986, 318-326.
Allan et al, "Synthesis of Analogues of GABA. IV Three Unsaturated Derivatives of 3-Aminocyclopentane-1-carboxylic acid," Aust. J. Chem., 33, 1980, 599-604.

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