Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Reexamination Certificate
2005-03-24
2008-03-04
Crane, L. E. (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
C536S027140, C536S027610, C514S046000
Reexamination Certificate
active
07339053
ABSTRACT:
The present invention provides a 4′-C-substituted-2-haloadenosine derivative represented by the following formula [I], [II], or [III]:(wherein X represents a halogen atom, R1represents an ethynyl group or a cyano group, and R2represents hydrogen, a phosphate residue, or a phosphate derivative residue). The present invention also provides a pharmaceutical composition containing the derivative and a pharmaceutically acceptable carrier therefor. Such derivative is useful as medicine for the treatment of Acquired Immune Deficiency Syndrome (AIDS).
REFERENCES:
patent: 5192749 (1993-03-01), O-Yang et al.
patent: 2004/0167096 (2004-08-01), Cheng et al.
patent: 00/69876 (2000-11-01), None
patent: 00/69877 (2000-11-01), None
patent: 03/068796 (2003-08-01), None
patent: 2005/090349 (2005-09-01), None
K. Kitano et al., “Synthesis of 4′-ethynyl-purine nucleosides possessing anti-HIV activity”, Nucleic Acids Symposium Series, No. 44, pp. 105-106, Jan. 2000.
H. Ohrui et al., “Syntheses of 4′-C-Ethynyl-β-D-arabino- and 4′-C-Ethynyl-2′-deoxy-β-D-ribo-pentofuranosylpyrimidines and -purines and Evaluation of their Anti-HIV activity”, J. Med. Chem., vol. 43, No. pp. 4516-4525, Nov. 2000.
H. Ohrui et al., “4′-C-Substituted-2′-Deoxynucleosides: A Family of Antiretroviral Agents which are Potent Against Drug-Resistant HIV Variants”, Current Drug Targets Infectious Disorders, vol. 1, No. 1, pp. 1-10, May 2001.
E. Kodama et al., “4′-Ethynyl Nucleoside Analogs: Potent Inhibitors of Multidrug-Resistant Human Immunodeficiency Virus Variants In Vitro”, Antimicrobial Agents and Chemotherapy, vol. 45, No. 5, pp. 1539-1546, May 2001.
S. Kohgo et al., “Synthesis of 4′-C-Ethynyl and 4′-C-Cyano Purine Nucleosides from Natural Nucleosides and Their Anti-HIV Activity”, Nucleosides, Nucleotides & Nucleic Acids, vol. 22, Nos. 5-8, pp. 887-889, 2003.
S. Shuto et al., “New Neplanocin Analogues. IV. 2-Fluoroneplanocin A: An Adenosine Deaminase-Resistant Equivalent of Neplanocin A1”, Chem. Pharma. Bull., vol. 42, No. 8, pp. 1688-1690, 1994.
T. Obara et al., “New Neplanocin Analogues. 7. Synthesis and Antiviral Activity of 2-Halo Derivatives of Neplanocin A1”, J. Med. Chem., vol. 39, No. 19, pp. 3847-3852, 1996.
K. Haraguchi et al., “Synthesis of a Highly Active New Anti-HIV Agent 2′,3′-Didehydro-3′-deoxy-4′-ethynylthymidine”, Bioorganic & Medicinal Chemistry Letters, vol. 13, No. 21, pp. 3775-3777, 2003.
S. Kohgo et al., “Synthesis of 4′-substituted nucleosides and their biological evaluation”, Nucleic Acids Symposium Series, No. 42, pp. 127-128, 1999.
R. Yamaguchi et al., “Synthesis of 4′-C-Ethynyl-β-D-ribo-pentofuranosyl Pyrimidines”, Biosci. Biotechnol. Biochem., vol. 63, No. 4, pp. 736-742, 1999.
S. Kohgo et al., “Synthesis of 4′-C-Ethynyl-β-D-arabino -and 4′-C-Ethynyl-2′-deoxy-β-D-ribo-pentofuranosyl Pyrimidines, and Their Biological Evaluation”, Biosci. Biotechnol. Biochem., vol. 63, No. 6, pp. 1146-1149, 1999.
H. Ohrui, “4′-C-Substituted-2′-Deoxy Nucleosides: Nucleosides Highly Active Against all kind of HIVs”, XIIst European Colloquinum on Heterocyclic Chemistry, 2004.
S. Kohgo et al., “Synthesis of the L-Enantiomer of 4′-C-Ethynyl-2′-deoxycytidine”, Biosci. Biotechnol. Biochem., vol. 65, No. 8, pp. 1879-1882, 2001.
K. Kitano et al., “Attempt to reduce cytotoxicity by snythesizing the L-enantiomer of 4′-C-ethynyl-2′-deoxypurine nucleosides as antiviral agents against HIV and HBV”, Antiviral Chemistry & Chemotherapy, vol. 14, pp. 161-167, 2004.
H. Hayakawa et al., “Potential of 4′-C-substituted nucleosides for the treatment of HIV-1”, Antiviral Chemistry & Chemotherapy, vol. 15, pp. 169-187, 2004.
S. Kohgo et al., “Design, Efficient Synthesis, and Anti-HIV Activity of 4′-C-Cyano- and 4′-C-Ethynyl-2′-deoxy Purine Nucleosides”, Nucleosides, Nucleotides and Nucleic Acids, vol. 23, No. 4, pp. 671-690, 2004.
M. Nomura et al., “Nucleosides and Nucleotides. 185. Synthesis and Biological Activities of 4′α-C-Branched-Chain Sugar Pyrimidine Nucleosides”, J. Med. Chem., vol. 42, pp. 2901-2908, 1999.
M. Siddiqui et al., “A 4′-C-Ethynyl-2′,3′-Dideoxynucleoside Analogue Highlights the Role of the 3′-OH in Anti-HIV Active 4′-C-Ethynyl-2′-deoxy Nucleosides”, J. Med. Chem., vol. 47, pp. 5041-5048, 2004.
K. Haraguchi et al., “Synthesis and Anti-HIV activity of 4′-Cyano-2′,3′-didehydro-3′-deoxythymidine”, Nucleosides, Nucleotides & Nucleic Acids, vol. 23, No. 4, pp. 647-654, 2004.
G. E. Dutschman et al., “Novel 4′-Substituted Stavudine Analog with Improved Anti-Human Immunodeficiency Virus Activity and Decreased Cytotoxicity”, Antimicrobial Agents and Chemotherapy, vol. 48, No. 5, pp. 1640-1646, May 2004.
X. Chen et al., “Synthesis of 3′-Fluoro-2′,3′-dideoxy-2′,3′-didehydro-4′-ethynyl-D-and -L-furanosyl Nucleosides”, J. Org. Chem., vol. 69, pp. 6034-6041, 2004.
D. Summerer et al., “4′C-Ethynyl-thymidine acts as a chain terminator during DNA-synthesis catalyzed by HIV-1 reverse transcriptase”, Bioorganic & Medicinal Chemistry Letters, vol. 15, pp. 869-871, 2005.
D Salvatori et al., “Adenine and deazaadenine nucleoside and deoxynucleoside analogues: inhibition of viral replication of sheep MVV (in vitro model of HIV) and bovine BHV-1”, Bioorganic and Medicinal Chemistry, vol. 10, pp. 2973-2980, 2002.
H. Ohrui et al., “4′C-Ethynyl-2′-deoxy-2-fluoroadenosine, a nucleoside derivative with supreme activity against a wide spectrum of HIVs and low toxicity: Highlights of the role of 3′-OH for biological activity”, 18thInternational Conference on Antiviral Research, Apr. 14-18, 2005.
Kodama Eiichi
Kohgo Satoru
Matsuoka Masao
Mitsuya Hiroaki
Ohrui Hiroshi
Crane L. E.
Wenderoth , Lind & Ponack, L.L.P.
Yamasa Corporation
LandOfFree
4′-C-substituted-2-haloadenosine derivative does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with 4′-C-substituted-2-haloadenosine derivative, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 4′-C-substituted-2-haloadenosine derivative will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3981006