Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2005-06-07
2005-06-07
Shah, Mukund J. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
06903224
ABSTRACT:
Substituted 1,3-oxathiolanes, such as cis- and trans-2-ethoxycarbonyl-5-hydroxy-1,3-oxathiolane and cis- and trans-2-ethoxycarbonyl-5-acetoxy-1,3-oxathiolane, are suitable as intermediates for the production of substituted 1,3-oxathiolanes nucleoside analogs having antiviral properties.
REFERENCES:
patent: 4000137 (1976-12-01), Dvonch et al.
patent: 4041037 (1977-08-01), Dvonch et al.
patent: 4268672 (1981-05-01), Vince
patent: 4336381 (1982-06-01), Nagata et al.
patent: 4415573 (1983-11-01), Ochi et al.
patent: 4960773 (1990-10-01), Korbonits et al.
patent: 5041449 (1991-08-01), Belleau et al.
patent: 5047407 (1991-09-01), Belleau et al.
patent: 5151426 (1992-09-01), Belleau et al.
patent: 5179104 (1993-01-01), Chu et al.
patent: 5204466 (1993-04-01), Liotta et al.
patent: 5210085 (1993-05-01), Liotta et al.
patent: 5234913 (1993-08-01), Furman et al.
patent: 5270315 (1993-12-01), Belleau et al.
patent: 5276151 (1994-01-01), Liotta et al.
patent: 5444063 (1995-08-01), Schinazi
patent: 5466806 (1995-11-01), Belleau et al.
patent: 5684010 (1997-11-01), Schinazi
patent: 5684164 (1997-11-01), Belleau et al.
patent: 5696254 (1997-12-01), Mansour et al.
patent: 5700937 (1997-12-01), Liotta et al.
patent: 5767122 (1998-06-01), Chu et al.
patent: 5792773 (1998-08-01), Chu et al.
patent: 5814639 (1998-09-01), Liotta et al.
patent: 5817667 (1998-10-01), Chu et al.
patent: 5827727 (1998-10-01), Liotta et al.
patent: 5830898 (1998-11-01), Schinazi
patent: 5834474 (1998-11-01), Schinazi
patent: 5852027 (1998-12-01), Liotta et al.
patent: 5869461 (1999-02-01), Cheng et al.
patent: 5914331 (1999-06-01), Liotta et al.
patent: 5914400 (1999-06-01), Liotta et al.
patent: 0212409 (1987-03-01), None
patent: 0337713 (1989-10-01), None
patent: 0349242 (1990-01-01), None
patent: 0363582 (1990-04-01), None
patent: 0 382 526 (1990-08-01), None
patent: 0 513 200 (1992-11-01), None
patent: 0 515 156 (1992-11-01), None
patent: 526253 (2002-11-01), None
patent: 2063257 (1981-06-01), None
patent: 2230266 (1990-10-01), None
patent: 44-20392 (1969-09-01), None
patent: 0026514 (1972-07-01), None
patent: 0179118 (1982-11-01), None
patent: WO 89/04662 (1989-06-01), None
patent: WO 90/12023 (1990-10-01), None
patent: WO 91/01326 (1991-02-01), None
patent: WO 92/10497 (1992-06-01), None
patent: WO 92/14729 (1992-09-01), None
patent: WO 92/18517 (1992-10-01), None
patent: WO 94/04154 (1994-03-01), None
patent: WO 94/09793 (1994-05-01), None
patent: WO 96/07413 (1996-03-01), None
Nokami, Junzo; Ryokume, Kazuyo; Inada, Junya, Tetrahedron Letters, 36(34), 6099-100 (English) 1995.
Chu, Chung K.; Beach, J. Warren; Jeong, Lak S.; Choi, Bo G.; Comer, Frank I.; Alves, Antonio J.; Schinazi, Raymond F. ,Journal of Organic Chemistry, 56(23), 6503-5 (English) 1991.
Chu et al., Tetrahedron Letter, vol. 32, No. 31, pp. 3791-3794, 1991.
Kim et al., 1,3-Dioxolanylpurine Nucleosides (2R,4R) and (2R,4S) with Selective Anti-HIV-1 Activity in Human Lymphocytes,Journal of Medical Chemistry,vol. 36, No. 1, pp. 30-37, 1993.
Kim et al., L-(2S,4S)-and L-a-(2S,4R)-Dioxolanyl Nucleosides as Potential Anti-HIV Agents: Asymmetric Synthesis and Structure-Activity Relationships,Journal of Medical Chemistry,vol. 36, No. 5, Mar. 5, 1993.
Kim et al.,Potent Anti-HIV and Anti-HBV Activities of(-)-L-β-Dioxolane-C and(+)-L-β-Dioxolane-C and (+)-L-β-Dioxolane-T and Their Asymmetric Syntheses, Tetrahedron Letters, vol. 33, No. 46, pp. 6899-69901, 1992.
Kim et al.,Asymmetric Synthesis of 1,3-Dioxolane-Pyrimidine Nucleosides and Their Anti-HIV Activity Journal of Medical Chemistry,vol. 35, pp. 1987-1995, 1992.
Wilson et al.,The Synthesis and Anti-HIV Activity of Pyrimidine Dioxolanyl Nucleosides, Bioorganic&Medicinal Chemistry Letters,vol. 3, No. 2, pp. 169-174, 1993.
Table 1—Activities and Toxicities of Selected 1,3-Dioxolane Nucleosides.
Allenmark, Chromatographic Enantioseparation: Methods and Applications, 1988.
Dr. Irving W. Wainer, A Practical Guide to the Selection and Use of HPLC Chiral Stationary Phases, presented by J.T. Baker, 1988.
Chiral Separations, Proceedings of the Chromatographic Society International Symposium on Chiral Separations, Ed. by Stevenson et al., Sep. 3-4, 1987, published 1988.
Souter, Chromatographic Separations of Stereoisomers, 1985.
Herdewijn et al., Resolution of Aristeromycin Enantiomers,Journal of Medical Chemistry,vol. 28, pp. 1385-1386, 1985.
Secrist et al., Resolution of Racemic Carbocyclic Analogues of Purine Nucleosides through the Action of Adenosine Deaminase. Antiviral Activity of the Carbocyclic 2′-Deoxyguanosine Enantiomers, Journal of Medical Chemistry, vol. 30, pp. 746-749, 1987.
DiMarco et al., High-performance liquid chromatographic determination of the isomeric purity of a series of dioxolane nucleoside analogues, Journal of Chromatography, vol. 645 (1993), pp. 107-114.
Siddiqui et al., Antiviral Optically Pure dioxolane Purine Nucleosides Analogues, Bioorganic & Medicinal Chemistry Letters, vol. 3, No. 8, pp. 1543-1546, 1993.
Fieser and Fieser, Organic Chemistry, 3rdEdition, p. 290, 1956.
Translation of Römpps Chemie Lexikon volume 5, pp. 3455-3456, publication year 1987.
Carey and Sundberg, Advanced Organic Chemistry, 2ndEdition, Part A: Structure and Mechanisms, pp. 73-75, 1984.
Dixon and Webb,Enzymes,2ndEdition, p. 204, 1964.
Morrison,Asymmetric Synthesis, Vol. 1, Analytical Methods,pp. 83-124, 1983.
Wainer and Draver,Drug Stereochemistry: Analytical Methods and Pharmacology,Ch. 12, pp. 299-310, 1988.
Triangle Homepage, Feb. 19, 1999; HIV and AIDS Drug Candidates, pp. 1-2 from Triangle website, Feb. 19, 1999.
BioChem Pharma Inc. Annual Report for 1997.
Frederiksen,Specificity of Adenosine Deaminase Toward Adenosine and 2′-Deoxyadenosine Analogues, Archives of Biochemistry and Biophysics,113, 383-388, 1966.
Pharmacia LKB Biotechnoloby Products Catalog 1988.
Norbeck et al., (±)-Dioxolane-T: A New 2′,3′-Dideoxynucleoside Prototype with In Vitro Activity Against HIV,Tetrahedron Letters, vol. 30, No. 46, pp. 6263-6266, 1989.
Belleau et al., Abstract T.C.O.1 Design and Activity of a Novel Class of Nucleoside Analogs Effective Against HIV-1, V International Conference on AIDS, The Scientific and Social Challenge, Jun. 4-9, 1989, Montréal, Québec, Canada.
Michael D. Grim,Enzyphobia, Biocatalysis Works,Summer 1998.
Holy et al.,Nucleic Acid Components and Their Analogues. Preparation and Properties of Some Nucleoside Hydroxyalkanephosphonates,Collection Czechoslov. Chem. Commun., vol. 37, pp. 2066-2076, 1972.
M.W. Gray,Analysis of O2′-Methylnucleoside 5′-Phosphates in Snake Venom Hydrolysates of RNA: Identification of O2′Methyl-5-Carboxymethyluridine as a Constituent of Yeast Transfer RNA, Canadian Journal of Biochemistry,vol. 53, No. 7, pp. 735-746, Jul. 1975.
Peter Pöchlauer,Syntheses of Homochiral Cyanohydrins in an Industrial Environment: Hydroxy Nitrile Lyases offer New Options,CHIMICA OGGI/chemistry today,vol. 16, pp. 15-19, May 1998.
Lassota et al.,Pyrimidine Homoribonucleosides: Synthesis, Solution Conformation, and Some Biological Properties,Z. Naturforsch. 42c., 589-598, 1987.
Rossomando, et al.,5′-Deoxy-5′-thioanalogs of Adenosine and Inosine 5′-Monophosphate: Studies with 5′Nucleotidase and Alkaline Phosphatase, Archives of Biochemistry and Biophysics,vol. 220, No. 1, Jan., pp. 71-78, 1983.
Holy,Nucleic Acid Components and Their Analogues. Synthesis of 6-Azauridine 5′-Methanephosphonate and 6-Azauridine 2′(3′)-Methanephosphonate,Collection Czechoslov. Chem. Commun., vol. 32, pp. 3713-3718, 1967.
Pless et al.,Purine Nucleosides and Nucleotides Unequivocally in the Syn Conformation: Guanosine and 5′GMP with 8-tert-Butyl and 8-(c-Hydroxyisopropyl)Substituents, Z. Naturforsch.33 c. 902-907 (1978).
Enzyme Nomenclature 1984,p. 282.
Bzowska et al.,Phosphorylation of Coformycin and 2′-Deoxycoformycin, and Substrate and Inhibitor Properties of the Nucleosides and Nucleotides in Several Enzyme Systems, Z. Naturforsch.40c, 710-714 (1985).
Belleau Pierette
Dixit Dilip M.
Nguyen-Ba Nghe
Bio-Chem Pharma Inc.
McKenzie Thomas
Millen White Zelano & Branigan P.C.
Shah Mukund J.
LandOfFree
Substituted 1,3-oxathiolanes does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Substituted 1,3-oxathiolanes, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted 1,3-oxathiolanes will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3520742