Nucleotide analogs

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C536S022100, C536S025340, C536S027140, C536S027210, C562S553000

Reexamination Certificate

active

07439350

ABSTRACT:
Nucleotide analogs characterized by the presence of an amidate linked amino acid or an ester linked group which is bonded to the phosphorus atom of phosphonate nucleotide analogs are disclosed. The analogs comprise a phosphoamidate or ester bond that is hydrolyzed in vivo to yield a corresponding phosphonate nucleotide analog. Methods and intermediates for their synthesis and use are described.

REFERENCES:
patent: 3524846 (1970-08-01), Moffatt et al.
patent: 4369181 (1983-01-01), Miller et al.
patent: 4590269 (1986-05-01), Prisbe et al.
patent: 4670424 (1987-06-01), MacCoss et al.
patent: 4724233 (1988-02-01), De Clercq et al.
patent: 4801710 (1989-01-01), MacCoss et al.
patent: 4808716 (1989-02-01), Holy et al.
patent: 4968788 (1990-11-01), Farquhar
patent: 5043339 (1991-08-01), Beauchamp
patent: 5047533 (1991-09-01), Reist et al.
patent: 5142051 (1992-08-01), Holy et al.
patent: 5208221 (1993-05-01), Kim et al.
patent: 5247085 (1993-09-01), Harnden et al.
patent: 5302585 (1994-04-01), Yu et al.
patent: 5352786 (1994-10-01), Jindrich et al.
patent: 5386030 (1995-01-01), Kim et al.
patent: 5391723 (1995-02-01), Priest
patent: 5495006 (1996-02-01), Climie et al.
patent: 5527803 (1996-06-01), Halazy et al.
patent: 5591851 (1997-01-01), Alexander
patent: 5618793 (1997-04-01), Cooper et al.
patent: 5618803 (1997-04-01), Bodor
patent: 5618964 (1997-04-01), Cheng et al.
patent: 5656745 (1997-08-01), Bischofberger et al.
patent: 5717095 (1998-02-01), Arimilli et al.
patent: 5798340 (1998-08-01), Bischofberger et al.
patent: 6225460 (2001-05-01), Bischofberger et al.
patent: 0173624 (1986-03-01), None
patent: 0206459 (1986-12-01), None
patent: 0206459 (1986-12-01), None
patent: 0253412 (1988-01-01), None
patent: 0269947 (1988-06-01), None
patent: 0269947BA (1988-06-01), None
patent: 0319228 (1989-06-01), None
patent: 0335770 (1989-10-01), None
patent: 0343133 (1989-11-01), None
patent: 0353955 (1990-02-01), None
patent: 0369409 (1990-05-01), None
patent: 0398231 (1990-11-01), None
patent: 0404296 (1990-12-01), None
patent: 0405748 (1991-01-01), None
patent: 0465297 (1992-01-01), None
patent: 0468119 (1992-01-01), None
patent: 0468866 (1992-01-01), None
patent: 0479640 (1992-04-01), None
patent: 0481214 (1992-04-01), None
patent: 0494370 (1992-07-01), None
patent: 0531597 (1993-03-01), None
patent: 0630381 (1994-12-01), None
patent: 0632048 (1995-01-01), None
patent: 1243214 (1971-08-01), None
patent: WO-8805438 (1988-07-01), None
patent: WO-9119721 (1991-12-01), None
patent: WO-9201698 (1992-02-01), None
patent: WO-2909611 (1992-06-01), None
patent: WO-9213869 (1992-08-01), None
patent: WO-9403466 (1994-02-01), None
patent: WO-9403467 (1994-02-01), None
patent: WO-9507919 (1995-03-01), None
patent: WO-9507920 (1995-03-01), None
Alexander et al., Collect Czech Chem Commun, 59:1853 (1994).
Amari et al., “Isolation of experimental anti-AIDS glycerophospholipids by micro-preparative reversed-phase high-performance liquid chromatography”, 590:153-161, J. Chromatog, 1992.
Andrei et al., “Comparative Activity of Selected Antiviral Compounds Against Clinical Isolates of Varicella Zoster Virus” , 14:318-328, Eur J Clin Microbiol Infect Dis, 1995.
Bai et al, “Structural Specificity of Mucosal-Cell Transport and Metabolism of Peptide Drugs: Implication for Oral Peptide Drug Delivery”, Pharmaceutical Research, vol. 9, No. 8, (1992), pp. 969-978.
Barnard et al, “Selective inhibition of cytomegaloviruses by 9-(3′-ethylphosphono-1′-hydroxymethyl-1′-propyloxy-methyl)guanine”, 22:77-89, Antiviral Res, 1993.
Beres, “Synthesis and Antitumor and Antiviral Properties of 5-Halo-and 5-(Trifluoromethyl)-2′-deoxyuridine 3′,5′-Cyclic Monophosphates and Neutral Triesters,” J Med Chem 29:1243-1249 (1986).
Bischofberger et al., “1-[((S)-2-Hydroxy-2-Oxo-1,4,2-Dioxaphosphorinan-5-yl)Methyl] Cytosine, an Intracellular Prodrug for (S)-1-(3-Hydroxy-2-Phosphonylmethoxypropyl)Cytosine with Improved Therapeutic Index In Vivo”, 38:2387-2391, Antimicro AG &Chemo, 1994.
Bronson et al, “Synthesis and Biological Activity of Carbocyclic Derivatives of the Potent Antiviral Agent 9-[2-(Phosphonomethoxy)Ethyl]Guanine (PMEG)”, Bioorganic & Medicinal Chemistry Letters, vol. 2, No. 7, (1992), pp. 685-690.
Bruice et al., “Hydrolysis of a Phosphate Diester by Simultaneous Carboxylate and Carboxyl Group Participation in a Rigid System with Kinetically Unfavorable Rotamers Frozen Out,” J Am Chem Soc 117:3639-3640 (1995).
Charvet et al., “Inhibition of Human Immunodeficiency Virus Type 1 Replication by Phosphonoformate- and Phosphonoacetate-2′,3′-Dideoxy-3′-thiacytidine Conjugates”, 37:2216-2223, J Med Chem, 1994.
Coates et al., “(-)-2′-Deoxy-3′-Thiacytidine Is a Potent, Highly Selective Inhibitor of Human Immunodeficeincy Virus Type 1 and Type 2 Replication In Vitro” , 36(4):733-739, Antimicro AG & Chemo, 1992.
Colla et al, “Synthesis and Antiviral Activity of Water-Soluble Esters of Acyclovir [9-[(2-Hydroxyethoxy)methyl]guanine],” J Med Chem 26:602-604 (1983).
Curley et al, “Synthesis and anti-HIV evaluation of some phosphoramidate derivatives of AZT: studies on the effect of chain elongation of biological activity”, 14:345-356, Antiviral Res, 1990.
Davies et al, “2′-Nor′2′-deoxyguanosine is an effective therapeutic agent for treatment of experimental herpes keratitis”, 7:119-125, Antiviral Res, 1987.
Dudley et al., “Pharmacokinetics of Stavudine in Patients with AIDS or AIDS-Related Complex”, 166(3):480-485, The Journal of Infectious Diseases, 1992.
Duke et al., “In vitro and in vivo activities of phosphate derivatives of 9-(1,3-dihydroxy-2-propoxymethyl)-guanine against cytomegaloviruses”, 6:299-308, Antiviral Res, 1986.
Engel, R., “Phosphonates as Analogues of Natural Phosphates”, 77(3):349-367, Chem Rev, 1977.
Farquhar et al., “Biologically Reversible Phosphate-Protective Groups,” J. Pharm Sci 72:324-325 (1983).
Farrow et al, “Synthesis and Biological Properties of Novel Phosphotriesters: A New Approach to the Introduction of Biologically Active Nucleotides into Cells,” J Med Chem 33:1400-1406 (1990).
Feng et al, “Combined treatment with 2′-nor-cGMP and ganciclovir against cytomegalovirus infection in a guinea pig model,” Antiviral Res 19:193-206 (1992).
Field et al, “Efficacy of 2′-nor-cyclicGMP in treatment of experimental herpes virus infections,” Antiviral Res 6:329-341 (1986).
Freed et al, “Evidence for Acyloxymethyl Esters of Pyrimidine 5′-Deoxyribonucleotides as Extracellular Sources of Active 5′-Deoxyribonucleotides in Cultured Cells,” Biochem Pharm 38:3193-3198 (1989).
Freeman et al, “3′-Azido-3′,5′-dideoxythymidine-5′-methylphosphonic Acid Diphosphate: Synthesis and HIV-1 Reverse Transcriptase Inhibition,” J Med Chem 35:3192-3196 (1992).
Gabrielsen et al, “Synthesis and In Vivo Anti-RNA-Viral Evaluation of a Phosphoramidate Derivative of 6-Azauridine: Orotidylic Acid Decaroboxylase Inhibitors, Pyrazofurin and 6-Azauridine; and 2-Thio-6-azauridine and its Triacetate”, 17(1):149,Antiviral Res, 1992.
Glazier et al., “Potent Topical Anti-Herpes Activity of a Lipophilic Phosphorus Prodrug for the Antiviral Agent PMEA”, p. A306—Poster, 8th International Conference on Antiviral Research, Santa Fe, NM, Apr. 23-28, 1995.
Gumport et, “Structure of the DNA Ligase-Adenylate Intermediate: Lysine (epsilon-amino)-Linked Adenosine Monophosphoramidate”, 68(10):2559-2563, Proc Natl Acad Sci, 1971.
Hadad, S., Journal of Pharmaceutical Sciences, 81(10) 1047-50 (1992).
Harnden et al, “Synthesis and Antiviral Activity of 9-Alkoxypurines. 1. 9-(3-Hydroxypropoxy)-and 9-[3-Hydroxy-2-(Hydroxy-2-(hydroxymethyl)propoxy]purin

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Nucleotide analogs does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Nucleotide analogs, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Nucleotide analogs will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3989276

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.