Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2008-07-01
2008-07-01
Rao, Deepak (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S263370, C514S263400, C544S265000, C544S276000, C544S278000
Reexamination Certificate
active
10942313
ABSTRACT:
Compounds which are active against viruses have the following formulas:wherein B is a purine or pyrimidine heterocyclic ring or base. In a preferred embodiment, the purine include 6-aminopurine (adenine), 6-hydroxypurine (hypoxanthine), 2-amino-6-hydroxypurine (guanine), 2,6-diamino-purine, 2-amino-6-azidopurine, 2-amino-6-halo substituted purines such as 2-amino-6-chloropurine, 2-amino-6-fluoropurine, 2-amino-6-alkoxypurines such as 2-amino-6-methoxypurine, 2-amino-6-cyclopropylaminopurine, 2-amino-6-alkylamino or 2-amino-6-dialkylamino substituted purines, 2-amino-6-thiopurine, 2-amino-6-alkylthio substituted purines, 3-deazapurines, 7-deazapurines and 8-azapurines. The pyrimidine incorporates cytosine, uracil and thymine, 5-halo substituted cytosines and uracils, 5-alkyl substituted cytosines and uracils including derivatives with a saturated or unsaturated alkyl group and 6-azapyrimidines.
REFERENCES:
patent: 6352991 (2002-03-01), Zemlicka et al.
patent: 7183268 (2007-02-01), Zemlicka et al.
Cheng et al., Reactions of Methylenecyclopropanes with a Diethylzinc-Bromoform System, and the Utilization for Synthesis of a Novel Cyclopropylidene-Nucleoside, Tetrahedron Letters, vol. 38, No. 2, pp. 9005-9008, 1997.
Douglar, Jr. Introduction to Viral Diseases, Cecil Textbook of Medicine, 20thEdition, vol. 2, pp. 1739-1747, 1996.
Goff, PubMed Abstract (J Gene Med. 3(6):517-28) Nov.-Dec. 2001.
Bosseray et al., PubMed Abstract (Pathol. Biol. 50(8):483-92), Oct. 2002.
Razonable et al., PubMed Abstract (Herpes 10(3):60-5), Dec. 2003.
Kumar et al., 5-(1-substituted) alkyl pyrimidine nucleosides as antiviral (herpes) agents, Current Medicinal Chemistry, vol. 11, No. 20, pp. 2749-2766, 2004.
Baker, et al.; “Utilization of the D- and L-Isomers of Methionine and Methionine Hydroxy Analogue as Determined by Chick Bioassay”Journal of Nutrition1980, 110(5), 959-964.
Silverman; “Prodrugs and Drug Delivery Systems”, Chapter 8 in “The Organic Chemistry of Drug Design and Drug Action,” pp. 352-401.
Chen, et al., “Structure-Activity Relationships of (S,Z)-2-Aminopurine Methylenecyclopropane Analogues of Nucleosides, Variation of Purine-6 Substituents and Activity against Herpesviruses and Hepatitis B Virus”J. Med. Chem. 2003, 46, 1531-1537.
Chen, et al.; “Synthesis of (Z)-(2,3-bis-Hydroxymethyl)- methylenecyclopropane Analogues of Purine Nucleosides”Nucleosides, Nucleotides&Nucleic Acids, 2003, 22(3), 265-274.
Franchetti, et al.; “Synthesis and Evaluation of the Anti-HIV Activity of Aza and Deaza Analogues of IsoddA and Their Phosphates as Prodrugs” J. Med. Chem. 1994, 37, 3534-3541.
Innaimo, et al.; “Identification of BMS-200475 as a Potent and Selective Inhibitor of Hepatitis B Virus,”Antimicrobial Agents and Chemotherapy1997, 41(7), 1444-1448.
Kern, et al.; “In Vitro Activity and Mechanism of Action of Methylenecyclopropane Analogs of Nucleosides against Herpesvirus Replication”Antimicrobial Agents and Chemotherapy2005, 49(3), 1039-1045.
Kern, et al.; “Oral Activity of a Methylenecyclopropane Analog, Cyclopropavir, in Animal Models for Cytomegalovirus Infections”Antimicrobial Agents and Chemotherapy2004, 48(12), 4745-4753.
McGuigan, et al.; “Intracellular Delivery of Bioactive AZT Nucleotides by Aryl Phosphate Derivatives of AZT”J. Med. Chem. 1993, 36, 1048-1052.
Mitsuya, et al.; “3′-Azido-3′ -deoxythymidine (BW A509U): An antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy- associated virus in vitro”Proc. Natl. Acad. Sci. USA1985, 82, 7096-7100.
Oatis, et al.; “Ring-Hydroxylated Propranolol: Synthesis and β-Receptor Antagonist and Vasodilating Activities of the Seven Isomers”J. Med. Chem. 1981, 24, 309-314.
Powell, et al.; “Metabolism of 5(S)-Hydroxy-6,8,11,14-eicosatetraenoic Acid and Other 5(S)- Hydroxyeicosanoids by a Specific Dehydrogenase in Human Polymorphonuclear Leukocytes”The Journal of Biological Chemistry1992, 267(27), 19233-19241.
Schaeffer, et al.; “Enzyme Inhibitors. 26. Bridging Hydrophobic and Hydrophilic Regions on Adenosine Deaminase with Some 9-(2-Hydroxy-3-alkyl)adenines”Journal of Medicinal Chemistry1974, 17(1), 6-8.
Schaeffer, et al.; “9-(2-Hydroxyethoxymethyl) guanine activity against viruses of the herpes group”Nature1978, 272, 583-585.
Zemlicka, et al., “Methylenecyclopropane analogs of nucleotides as antiviral agents” (Schinazi and Liotta, eds),Frontiers in Nucleoside and Nucleic Acids, IHL Press 2004, 267-307.
Zhou, et al.; “Synthesis and Antiviral Activity of (Z)- and (E)-2,2-[Bis(hydroxymethyl) cyclopropylidene] methylpurines and-pyrimidines: Second-Generation Methylenecyclopropane Analogues of Nucleosides”J. Med. Chem. 2004, 47, 566-575.
Drach John C.
Zemlicka Jiri
Zhou Shaoman
Foley & Hoag LLP
Rao Deepak
Smith, Esq. DaAnn F.
The Regents of the University of Michigan
Wayne State University
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