Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
2007-04-17
2007-04-17
Shameem, Golam M. M. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C544S244000, C548S112000, C558S081000
Reexamination Certificate
active
09518501
ABSTRACT:
Novel cyclic phosphoramidate prodrugs of drugs of formula Iin their use in delivery of drugs to the liver, their use in enhancing oral bioavailability, and their method of preparation are described.
REFERENCES:
patent: 3018302 (1962-01-01), Bielefeld et al.
patent: 3404178 (1968-10-01), Roy
patent: 3796700 (1974-03-01), Yoshioka et al.
patent: 4255566 (1981-03-01), Carrico et al.
patent: 4318982 (1982-03-01), Hornby et al.
patent: 4340668 (1982-07-01), Hornby et al.
patent: 4376165 (1983-03-01), Hornby et al.
patent: 4447529 (1984-05-01), Greenquist et al.
patent: 4621077 (1986-11-01), Rosini et al.
patent: 4659825 (1987-04-01), Holy et al.
patent: 4705651 (1987-11-01), Staibano
patent: 4724232 (1988-02-01), Rideout et al.
patent: 4724233 (1988-02-01), De Clercq et al.
patent: 4777163 (1988-10-01), Bosies et al.
patent: 4804655 (1989-02-01), Müller et al.
patent: 4808716 (1989-02-01), Holy et al.
patent: 4861759 (1989-08-01), Mitsuya et al.
patent: 4879277 (1989-11-01), Mitsuya et al.
patent: 4882142 (1989-11-01), Simon et al.
patent: 4898724 (1990-02-01), Simon et al.
patent: 4939130 (1990-07-01), Jaeggi et al.
patent: 4952575 (1990-08-01), Sauerbier et al.
patent: 4952740 (1990-08-01), Juge et al.
patent: 5034394 (1991-07-01), Daluge
patent: 5047533 (1991-09-01), Reist et al.
patent: 5089500 (1992-02-01), Daluge
patent: 5130303 (1992-07-01), Akiyama et al.
patent: 5153183 (1992-10-01), Kawabe et al.
patent: 5157027 (1992-10-01), Biller et al.
patent: 5204355 (1993-04-01), Zsadon et al.
patent: 5210085 (1993-05-01), Liotta et al.
patent: 5212304 (1993-05-01), Fung et al.
patent: 5240946 (1993-08-01), Kinney et al.
patent: 5246937 (1993-09-01), Harnden et al.
patent: 5258538 (1993-11-01), Fung et al.
patent: 5366965 (1994-11-01), Strein
patent: 5480875 (1996-01-01), Isomura et al.
patent: 5532225 (1996-07-01), Reist et al.
patent: 5583122 (1996-12-01), Benedict et al.
patent: 5658889 (1997-08-01), Gruber et al.
patent: 5663159 (1997-09-01), Starrett, Jr. et al.
patent: 5681590 (1997-10-01), Bechard et al.
patent: 5721219 (1998-02-01), Ingall et al.
patent: 5814639 (1998-09-01), Liotta et al.
patent: 5840716 (1998-11-01), Ubasawa et al.
patent: 5869467 (1999-02-01), Holy et al.
patent: 5914331 (1999-06-01), Liotta et al.
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: 6054587 (2000-04-01), Reddy et al.
patent: 6110903 (2000-08-01), Kasibhatla et al.
patent: 6117873 (2000-09-01), Acklin 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: 6756360 (2004-06-01), Erion et al.
patent: 492 738 (1970-06-01), None
patent: 492 738 (1970-06-01), None
patent: 16 93 219 (1970-09-01), None
patent: 35 12 781 (1985-04-01), None
patent: 0 002 062 (1979-05-01), None
patent: 0 002 062 (1979-05-01), None
patent: 0 072 987 (1982-08-01), None
patent: 0 072 531 (1983-02-01), None
patent: 0 072 531 (1983-02-01), None
patent: 0 158 057 (1985-10-01), None
patent: 0 161 955 (1985-11-01), None
patent: 0 161 955 (1985-11-01), None
patent: 0 261 283 (1986-09-01), None
patent: 0 261 283 (1986-09-01), None
patent: 0 180 276 (1988-12-01), None
patent: 0 180 276 (1988-12-01), None
patent: 0 338 372 (1989-10-01), None
patent: 0 338 372 (1989-10-01), None
patent: 0 353 692 (1990-02-01), None
patent: 0 353 692 (1990-02-01), None
patent: 0 481 214 (1992-04-01), None
patent: 0 481 214 (1992-04-01), None
patent: 987378 (1970-09-01), None
patent: 62-195392 (1987-08-01), None
patent: 62-249996 (1987-10-01), None
patent: WO 90/08155 (1990-07-01), None
patent: WO 90/10636 (1990-09-01), None
patent: WO 09/19721 (1991-12-01), None
patent: 96/01267 (1996-01-01), None
patent: 96/01267 (1996-01-01), None
patent: 97/03679 (1997-02-01), None
patent: 97/03679 (1997-02-01), None
patent: WO 97/22614 (1997-06-01), None
patent: 98/09668 (1998-03-01), None
patent: 98/09668 (1998-03-01), None
patent: 98/39342 (1998-09-01), None
patent: 98/39343 (1998-09-01), None
patent: 98/39344 (1998-09-01), None
patent: WO 99/45016 (1999-09-01), None
patent: WO 01/39724 (2001-06-01), None
Bentrude, Wesley G.; Setzer, William N.; Sopchik, Alan E.; Bajwa, Gurdip S.; Burright, Donald D.; Hutchinson, John P., J. Am. Chem. Soc., 108(21), 6669-75 (English) 1986.
Bentrude, Wesley G.; Setzer, William N.; Sopchik, Alan E.; Chandrasekaran, Subramanian; Ashby, Michael T., J. Am. Chem. Soc., 110(21), 7119-27 (English) 1988.
Denmark, Scott E.; Chatani, Naoto; Pansare, Sunil V., Tetrahedron, 48(11), 2191-2208 (English) 1992.
Lorey, Martina; Meier, Chris, Nucleosides Nucleotides, 18(4 & 5), 947-948 (English) 1999 (Abstract only).
Wolff, Manfred E. “Burger's Medicinal Chemistry, 5ed, Part I”, John Wiley & Sons, 1995, pp. 975-977.
Banker, G.S. et al, “Modern Pharmaceutics, 3ed.”, Marcel Dekker, New York, 1996, pp. 451 and 596.
William Reusch, “Virtual Text of Organic Chemistry”, Michigan State University, [online] Aug. 1, 2004, [retrieved on Jan. 19, 2005]. Retrieved from the internet, <http://www.cem.msu.edu%7Ereusch/VirtualText/special2.htm#top1>.
David,Evans “Chemistry 206 Advanced Organic Chemistry”, Harvard University, [online] Sep. 11, 2003, [retrieved on Jan. 19, 2005]. Retrieved from the internet, <http://www.courses.fas.harvard.edu/˜chem206/Fall—2003/Lectures—and—Handouts/>.
“Patent Abstracts of Japan,” vol. 1998, No. 1, Jan. 30, 1998 & JP 09241284 A (Yamishata Koji, et al.; Nippon Soda Co. Ltd), Sep. 16, 1997.
DeLombaert, et al., N-Phosphonomethyl Dipeptides and Their Phosphonate Prodrugs, a New Generation of Neutral Endoprptidase (NEP, EC 3.4.24.11) Inhibitors,J. Med. Chem.37: 498-511 (1994).
Edmunson, et al., “Cyclic Organophosphorus Compounds. Part 23. Configurational Assignments in the 4-Phenyl-1,3,2λ5-dioxaphosphorinane Series. X-Ray Molecular Structure of cis-2-Benzylamino-4-phenyl-1,3,2-dioxaphosphorinane 2-Oxide,”J. Chem. Res. Synop., 5: 122-123 (1989).
Farquhar, et al., “5′-‘40-(Pivaloyloxy)-1, 3, 2-dioxaphosphorin an -2-y!-2′-deoxy-5-fluorouridine: a membrane-permeating prodrug of 5-fluoro-2′-deoxyuridylic acid (FDUMP)’”J. Med. Chem.38:488-495 (1995).
Farquhar, et al., “Biologically Reversible Phosphate-Protective Groups,”J. Pharm. Sci.72(3): 324-325 (1983).
Farquhar, et al., “Synthesis and Biological Evaluation of 9-[5′-(2-Oxo-1,3,2-oxazaphosphorinan-2-yl)-β-D-arabinosyl]adenine and 9-[5′-(2-Oxo-1,3,2-dioxazaphosphorinan-2-yl)-β-D-arabinosyl]adenine: Potential Neutral Precursors of 9-[β-D-Arabinofuranosyl]adenine 5′-Monophosphate,”J. Med. Chem.28: 1358-1361 (1985).
Farquhar, et al., “Synthesis and Biological Evaluation of Neutral Derivatives of 5-Fluoro-2′-deoxyuridine 5′-Phosphate,”J. Med. Chem.26:1153-1158 (1983).
Freed, et al., “Evidence For Acyloxymethyl Esters of Pyrimidine 5′-Deoxyribonucleotides as Extracellular Sources of Active 5′-Deoxyribonucleotides in Cultured Cells,”Biochem. Pharmac.38: 3193-3198 (1989).
Hillers, et al., “Analogs of pyrimidinemono-and polynucleotides. IV. Phosphates of 1-(1,4-dihydroxy-2-pentyl)thymine and 1-(1,3-dihydroxy-2-propyl) uracil.”Khim Geterotski Soedin5:678-683 (1978). Chem Abst. v 89 No. 17; abst No. 146864u.
Hunston, et al., “Synthesis and Biological Properties of Some Cyclic Phosphotriesters Derived from 2′-Deoxy-5-fluorouridine,”J. Med. Chem.27: 440-444 (1984).
Kryuchkov, et al.,Izv. Akad. Nauk SSSR, Ser. Khim.6: 1201-1248 (1987).
Lok, et al., “Neurotoxicity associated with adenine arabinoside monophosphate in the treatment of chronic hepatitis B virus infection,”J. Antimicrob. Chemotherap.14: 93-99 (1984).
Ludeman, et a
Boyer Serge H.
Erion Mark D.
Reddy K. Raja
Metabasis Therapeutics, Inc.
Sackey Ebenezer
Shameem Golam M. M.
Sterne Kessler Goldstein & Fox P.L.L.C.
LandOfFree
Phosphorus-containing prodrugs does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Phosphorus-containing prodrugs, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Phosphorus-containing prodrugs will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3748181