Phosphonic acid based prodrugs of PMEA and its analogues

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C544S244000

Reexamination Certificate

active

10436922

ABSTRACT:
Prodrugs of Formula I, their uses, their intermediates, and their method of manufacture are described:wherein:M and V are cis to one another and MPO3H2is a phosphonic acid selected from the group consisting of 9-(2-phosphonylmethoxyethyl)adenine, (R)-9-(2-phosphonylmethoxy propyl)adenine, 9-(2-phosphonylmethoxyethyl)guanine, 9-(2-phosphonylmethoxy ethyloxy)adenine, 9-(2-phosphonylmethoxyethyl)-2,6-diaminopurine, (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine, (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine, 9-(3-hydroxy-2-phosphonylmethoxypropyl)guanine, and (S)-9-(3-fluoro-2-phosphonyl methoxypropyl)adenine;V is selected from a group consisting of phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furanyl, 3-furanyl, 2-thienyl, and 3-thienyl, all optionally substituted with 1-3 substituents selected from a group consisting of F, Cl, Br, C1-C3 alkyl, CF3and OR6;R6is selected from the group consisting of C1-C3 alkyl, and CF3;and pharmaceutically acceptable salts thereof.

REFERENCES:
patent: 3018302 (1962-01-01), Bielefeld et al.
patent: 4659825 (1987-04-01), Holy et al.
patent: 4724233 (1988-02-01), De Clercq et al.
patent: 4808716 (1989-02-01), Holy et al.
patent: 4952740 (1990-08-01), Juge et al.
patent: 5130427 (1992-07-01), Alexander et al.
patent: 5142051 (1992-08-01), Holy et al.
patent: 5157027 (1992-10-01), Biller et al.
patent: 5514798 (1996-05-01), Bischofberger et al.
patent: 5658889 (1997-08-01), Gruber et al.
patent: 5665386 (1997-09-01), Benet et al.
patent: 5686629 (1997-11-01), Bischofberger et al.
patent: 5716928 (1998-02-01), Benet et al.
patent: 5962440 (1999-10-01), Sulsky
patent: 5962522 (1999-10-01), Wacher et al.
patent: 6004927 (1999-12-01), Benet et al.
patent: 6028054 (2000-02-01), Benet et al.
patent: 6037335 (2000-03-01), Takashima et al.
patent: 6054587 (2000-04-01), Reddy et al.
patent: 6110903 (2000-08-01), Kasibhatla et al.
patent: 6121234 (2000-09-01), Benet et al.
patent: 6180666 (2001-01-01), Wacher et al.
patent: 6284748 (2001-09-01), Dang et al.
patent: 6294672 (2001-09-01), Reddy et al.
patent: 6312662 (2001-11-01), Erion et al.
patent: 6399782 (2002-06-01), Kasibhatla et al.
patent: 6489476 (2002-12-01), Dang et al.
patent: 6752981 (2004-06-01), Erion et al.
patent: 6946115 (2005-09-01), Erion et al.
patent: 2003/0225277 (2003-12-01), Kopcho et al.
patent: 2003/0229225 (2003-12-01), Reddy et al.
patent: 2004/0092476 (2004-05-01), Erion et al.
patent: 2004/0192651 (2004-09-01), Boyer et al.
patent: 2005/0282782 (2005-12-01), Martin
patent: 2005/0288240 (2005-12-01), Erion et al.
patent: 2006/0030545 (2006-02-01), Cheng et al.
patent: 2006/0046981 (2006-03-01), Shibata
patent: 0161955 (1985-11-01), None
patent: 0180276 (1986-05-01), None
patent: 0338372 (1989-10-01), None
patent: 0 481 214 (1991-09-01), None
patent: 0632048 (1995-01-01), None
patent: 0353692 (1995-10-01), None
patent: WO 93/19075 (1993-09-01), None
patent: WO 95/07920 (1995-03-01), None
patent: WO 96/01267 (1996-01-01), None
patent: WO 91/19721 (1996-12-01), None
patent: WO 97/03679 (1997-02-01), None
patent: WO 98/39342 (1998-09-01), None
patent: WO 98/39343 (1998-09-01), None
patent: WO 98/39344 (1998-09-01), None
patent: WO 99/04774 (1999-02-01), None
patent: WO 00/38666 (2000-07-01), None
patent: WO 00/52015 (2000-09-01), None
patent: WO 02/08241 (2002-01-01), None
March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structures, McGraw Hill Book Company, New York, NY (1968) pp. 87-88.
Wacher, V.J., et al., Advanced Drug Delivery Reviews 46:89-102 (2001).
Wacher, et al., “Active Secretion and Enterocytic Drug Metabolism Barriers to Drug Absorption,”Adv. Drug Del. Rev., 46:89-102 (2001).
Yamamoto, et al., “Synthesis of Pyridine N-Oxide-SbCl5 Complexes and Their Intrmolecular and Oxygen-Transfer Reaction,”Tetrahedron Lett., 37:1871-3 (1981).
Phillion, et al., “Synthesis and Reactivity of Diethyl Phosphonomethyltriflate,”Tetrahedron Lett., 27(13):1477-80 (1986).
Quast, et al., “Herstellung von Methylphosphonsaure-dichlorid,”Synthesis, 490 (1974).
Ramachandran, et al., “Efficient General Synthesis of 1,2- and 1,3-Diols in High Enantiomeric Excess via the Intramolecular Asymmetric Reduction of the Corresponding Ketoalkyl Diisopinocampheylborinate Intermediates,”Tetrahedron Lett., 38(5):761-4 (1997).
Russell, et al., “Determination of 9-[(2-phosphonylmethoxy)ethyl]adenine in rat urine by high-performance liquid chromatography with fluorescence detection,”J Chromatogr., 572(1-2):321-6 (1991).
Sakamoto, et al., “The Palladium-Catalyzed Arylation of 4H-1,3-Dioxin,”Tetrahedron Lett., 33(45):6845-8 (1992).
Serafinowska, et al., “Synthesis and in Vivo Evaluation of Prodrugs of 9-[2—(Phosphonomethoxy)ethoxy]adenine,”J. Med. Chem., 38:1372-9 (1995).
Shaw, et al., “Pharmacokinextics and Metabolism of Selected Prodrugs of PMEA in Rats,”Drug Metabolism Dis., 25(3):362-366 (1997).
Starrett, et al., “Synthesis, oral bioavailability determination, and in vitro evaluation of prodrugs of the antiviral agent 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA),”J Med Chem., 37(12):1857-64 (1994).
Still, et al., “Direct Synthesis of Z-Unsaturated Esters. A Useful Modification of the Horner-Emmons Olefination,”Tetrahedron Lett., 24(41):4405-8 (1983).
Stowell, et al., “The Mild Preparation of Synthetically Useful Phosphonic Dichlorides: Application to the Synthesis of Cyclic Phosphonic Diesters and Diamides,”Tetrahedron Lett., 31(23):3261-2 (1990).
Tawfik, et al., “1,8-Diazabicyclo[5.4.0]undecene Mediated Transesterification of p-Nitrophenyl Phosphonates: A Novel Route to Phosphono Esters,”Synthesis, 968-72 (1993).
Turner, “A General Approach to the Synthesis of 1,6-, 1,7-, and 1,8-Naphthyridines,”J. Org. Chem., 55:4744-50 (1990).
Turner, et al., “Acylation off Ester Enolates by N-Methoxy-N-methylamides: An Effective Synthesis of β-Keto Ester,”J. Org. Chem., 54:4229-31 (1989).
Khamnei, et al., “Neighboring Group Catalysis in the Design of Nucleotide Prodrugs,”J. Med. Chem., 39:4109-15 (1996).
Kobayashi, et al., “Acylation of Active Methylene Compounds via Palladium Complex-Catalyzed Carbonylative Cross-Coupling of Organic Halides,”Tetrahedron Lett., 27(39):4745-8 (1986).
Mitsunobu, “The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products,”Synthe., 1-28 (1981).
Moriarty, et al., “Diphenyl Methylphosphonate as a Phosphonylation Reagent with High Diastereoselectivity at Phosphorus,”Tetrahedron Lett., 38(15):2597-600 (1997).
Mukaiyama, “Chapter 3: The Directed Aldol Reaction,”Org. React., 28:203-331 (1982).
Mulato, et al., “Nonsteroidal Anti-Inflammatory Drugs Effeciently Reduce the Transport and Cytotoxicity of Adefovir Mediated by the Human Renal Organic Anion Transporter 1,”J. Pharm. Exp. Ther., 295:10-15 (2001).
Murono, et al., “Prevention and inhibition of nasopharyngeal carcinoma growth by antiviral phosphonated nucleoside analogs,”Cancer Res., 61(21):7875-7 (2001).
Naesens, et al., “Therapeutic Potential of HPMPC (Cidofovir), PMEA (Adefovir) and Related Acyclic Nucleoside Phosphonate Analogues as Broad-Spectrum Antiviral Agents,”Nucleosides&Nucleotides, 16(7-9):983-92 (1997).
Naesens, et al., “HPMPC (cidofovir), PMEA (adefovir) and Related Acyclic Nucleoside Phosphonate Analogues: A Review of Their Pharmacology and Clinical Potential in the Treatment of Viral Infections,”Antiviral Chem. Chemothera., 8(1):1-23 (1997).
Noble, et al., “Adefovir Dipivoxil,”Drugs, 58(3):479-487 (1999).
Chashi, et al., “Synthesis of Phosphonosphingoglycolipid Found in Marine Snail Turbo Cornutus,”Tetrahedron Lett., 29(10):1189-92 (1988).
Oliyai, et al., “Kinetic Studies of the Degradation of Oxycarbonyloxymethyl Prodrugs of Adefovir and Tenofovir in Solution,”Nucleosides, N

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

Phosphonic acid based prodrugs of PMEA and its analogues does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Phosphonic acid based prodrugs of PMEA and its analogues, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Phosphonic acid based prodrugs of PMEA and its analogues will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3776580

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