Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2007-12-11
2011-10-25
Andres, Janet (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C546S286000, C548S136000, C548S241000, C514S344000, C514S363000, C514S548000
Reexamination Certificate
active
08044230
ABSTRACT:
The present invention discloses certain novel prodrugs of chloramphenicol or thiamphenicol, or of an analog of either, including prodrugs of pharmaceutically acceptable salts of chloramphenicol or thiamphenicol or of their analogs, including nitrogen-containing esters of both alcohol groups of such compounds. In certain embodiments these novel prodrugs are sufficiently water-soluble to serve the functions needed of a prodrug of chloramphenicol or thiamphenicol or of an analog of either. In one embodiment, a certain subclass of the compounds also possesses the hydrolytic stability needed to maintain the prodrug in solution in the subject's system until appropriate conditions exist when the prodrug can hydrolyze, releasing the active compound in question.
REFERENCES:
patent: 2671748 (1954-03-01), Crooks
patent: 3405165 (1968-10-01), Rebstock
patent: 3475470 (1969-10-01), Rebstock
patent: 3740411 (1973-06-01), Akiyama et al.
patent: 3770889 (1973-11-01), Gutschick et al.
patent: 3950360 (1976-04-01), Aoki et al.
patent: 3984564 (1976-10-01), Aoki et al.
patent: 4199569 (1980-04-01), Chabala et al.
patent: 4310519 (1982-01-01), Albers-Schonberg et al.
patent: 4311857 (1982-01-01), Nagabhushan
patent: 4582918 (1986-04-01), Nagabhushan et al.
patent: 4743700 (1988-05-01), Jommi et al.
patent: 4820695 (1989-04-01), Debono et al.
patent: 4876352 (1989-10-01), Schumacher et al.
patent: 4916154 (1990-04-01), Asato et al.
patent: 4973750 (1990-11-01), Nagabhushan et al.
patent: 5082863 (1992-01-01), Apelian et al.
patent: 5089480 (1992-02-01), Gibson et al.
patent: 5105009 (1992-04-01), Jommi et al.
patent: 5227494 (1993-07-01), Schumacher et al.
patent: 5288710 (1994-02-01), Cvetovich
patent: 5352832 (1994-10-01), Wu et al.
patent: 5382673 (1995-01-01), Clark et al.
patent: 5399717 (1995-03-01), Cvetovich et al.
patent: 5567844 (1996-10-01), Jommi et al.
patent: 5663361 (1997-09-01), Towson et al.
patent: 5958888 (1999-09-01), Macy et al.
patent: 5965603 (1999-10-01), Johnson et al.
patent: 6054434 (2000-04-01), Kropp et al.
patent: 6136838 (2000-10-01), Chern et al.
patent: 6174540 (2001-01-01), Williams et al.
patent: 6239112 (2001-05-01), Macy et al.
patent: 6270768 (2001-08-01), O'Connell et al.
patent: 6271255 (2001-08-01), Leadlay et al.
patent: 6339063 (2002-01-01), Kropp et al.
patent: 6437151 (2002-08-01), Leadlay et al.
patent: 6472371 (2002-10-01), Dirlam et al.
patent: 6514492 (2003-02-01), Gao et al.
patent: 6514945 (2003-02-01), Boettner
patent: 6733767 (2004-05-01), Chern et al.
patent: 6790867 (2004-09-01), Kohan et al.
patent: 6825327 (2004-11-01), Sklavounos et al.
patent: 7041670 (2006-05-01), Boojamra et al.
patent: 7153842 (2006-12-01), Hecker et al.
patent: 7361689 (2008-04-01), Shuster et al.
patent: 7572777 (2009-08-01), Hecker et al.
patent: 7713950 (2010-05-01), Shuster et al.
patent: 7786329 (2010-08-01), Towson
patent: 2002/0102280 (2002-08-01), Anderson
patent: 2003/0216447 (2003-11-01), Kohan et al.
patent: 2004/0242546 (2004-12-01), Freehauf et al.
patent: 2005/0182059 (2005-08-01), Winzenberg et al.
patent: 2005/0182139 (2005-08-01), Shuster et al.
patent: 2006/0063841 (2006-03-01), Meyer et al.
patent: 2006/0128779 (2006-06-01), Winzenberg et al.
patent: 2006/0281695 (2006-12-01), Meyer et al.
patent: 2007/0055066 (2007-03-01), Towson
patent: 2007/0055067 (2007-03-01), Towson
patent: 2007/0155799 (2007-07-01), Glinka et al.
patent: 2007/0238700 (2007-10-01), Winzenberg et al.
patent: 2008/0145317 (2008-06-01), Tongiani et al.
patent: 2008/0146640 (2008-06-01), Glinka
patent: 2008/0153906 (2008-06-01), Celly et al.
patent: 2008/0188556 (2008-08-01), Glinka et al.
patent: 2008/0319200 (2008-12-01), Towson
patent: 2009/0062397 (2009-03-01), Tongiani
patent: 2009/0156683 (2009-06-01), Simmons et al.
patent: 2009/0170954 (2009-07-01), Towson et al.
patent: 2009/0275662 (2009-11-01), Barbot
patent: 2010/0210851 (2010-08-01), Towson
patent: 1507858 (2004-06-01), None
patent: 0980248 (2001-10-01), None
patent: 804986 (1958-11-01), None
patent: 1173562 (1969-12-01), None
patent: 1263116 (1972-02-01), None
patent: WO 02/41899 (2002-05-01), None
patent: WO 03/097054 (2003-11-01), None
patent: WO 2004/089355 (2004-10-01), None
Banerjee et al, “Photoreleasable Protecting Groups Based on Electron Transfer Chemistry. Donor Sensitized Release of Phenacyl Groups from Alcohols, Phosphates and Diacids”, Tetrahedron, vol. 55, pp. 12699-12710 (1999).
Brunelle, “Novel Chatalysis of o-Nitrophenyl Carbonates by p-Dimethylaminopyridine”, Tetrahedron Letters, vol. 23, No. 17, pp. 1739-1742 (1982).
Castro et al, “Kinetic Investigation of the Phenolysis of Phenyl 4-Nitrophenyl and Phenyl 2,4-Dinitrophenyl Carbonates”, J. Chem. Soc. Perkin Trans., vol. 2, pp. 2351-2354 (2001).
Chen et al, “Synthesis of (+)-CP-263,114”, J. Am. Chem. Soc., vol. 122, pp. 7424-7425 (2000).
Chmielewski et al, “Thermolytic Carbonates for Potential 5′-Hydroxyl Protection of Deoxyribonucleosides”, J. Org.Chem., vol. 68, pp. 10003-10012 (2003).
Diaz et al, Cal-B-Catalyzed Alkoxycarbonylation of A-Ring Stereoisomeric Synthons of 1α,25-Dihydroxyvitamin D3: A Comparative Study. First Regioselective Chemoenzymatic Synthesis of 19-nor-A-Ring Carbonates, J. Org.Chem., vol. 66, pp. 4227-4232 (2001).
Dubowchik et al, “Cathepsin B-Sensitive Dipeptide Prodrugs. 2. Models of Anticancer Drugs Paclitaxel (Taxol®), Mitomycin C and Doxorubicin”, Bloorganic & Medicinal Chemistry Letters, vol. 8, pp. 3347-3352 (1998).
Greiner et al, “Synthesis of Phosphoramidite Building Blocks of 2′-Amino-2′deoxyribonucleosides: New Compounds for Oligonucleotide Synthesis”, Helvetica Chimica Acta, vol. 81, pp. 1528-1544 (1998).
Harada et al, “Allyloxycarbonyl Group as a Protective Group for the Hydroxyl Group in Carbohydrates”, J. Carbohydrate Chemistry, vol. 14, No. 1, pp. 165-170 (1995).
Iimori et al, “A Novel Intramolecular Decarboxylative GlycosylationviaMixed Carbonate”, Tetrahedron Letters, vol. 37, No. 13, pp. 2267-2270 (1996).
Kenar et al, “Synthesis and Characterization of Dialkyl Carbonates Prepared from Mid-, Long-Chain, and Guerbet Alcohols”, J. Am. Oil Chem. Soc., vol. 81, No. 3, pp. 285-291 (2004).
Kozikowski et al, “Novel PI Analogues Selectively Block Activation of the Pro-Survival Serine/Threonine Kinase Akt”, J. Am. Chem. Soc., vol. 125, pp. 1144-1145 (2003).
Kryczka et al, “Syntheses de Carbonates et Carbamates Benzyliques et Allyliques”, Bull. Soc. Chim. Belg., FR, vol. 101, No. 2, pp. 147-157 (1992).
Li et al, “Synthesis of DNA Oligomers Possessing a Covalently Cross-Linked Watson—Crick Base Pair Model”, Angew. Chem. Int. Ed., vol. 113, No. 8, pp. 1519-1523 (2001).
Marca et al, “Observations on Antibacterial Activity of Thiamphenicol Glycinate Acetylcysteinate”, Quademi Sclavo di Diagnostica Clinica e di Laboratorio, vol. 15, No. Suppl. 1, pp. 777-784 (Jun. 1979).
Mindl et al, “Alkoxycarbonylation of Alcohols and phenols by Nitrosoformates”, Collect Czech. Chem. Commun., vol. 61, pp. 1053-1063 (1996).
Moris et al, “A Novel and Convenient Route to 3′-Carbonates from Unprotected 2′-Deoxynucleosides Through an Enzymatic Reaction”, J. Org. Chem., vol. 57, pp. 2490-2492 (1992).
Moris et al, “Enzymatic Acylation and Alkoxycarbonylation of α-, Xylo-, Anhydro-, and Arabino-Nucleosides”, Tetrahedron, vol. 49, No. 44, pp. 10089-10098 (1993).
Nongkunsarn et al, Rearrangement and Radical Mediated Decarboxylation of Trimethylsilyl Benzoates Using Xenon Difluoride, J. Chem. Soc. Perkin Trans., vol. 1, No. 2, pp. 121-122 (1996) [Abstract].
Olofson et al, “A Regiospecific and Stereospecific Route to Enol Carbonates and Carbamates: Closer Look at a ‘Naked Anion’”, Tetrahedron Letters, vol. 21, pp. 819-822, (1980).
Peri et al, “Preparation of Bicyclo[3.2.0]heptane-2-endo,7-endo-diols:1,3-Diols with a Chira
Andres Janet
Intervet Inc.
Reese Heidi
LandOfFree
Water-soluble prodrugs of chloramphenicol, thiamphenicol,... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Water-soluble prodrugs of chloramphenicol, thiamphenicol,..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Water-soluble prodrugs of chloramphenicol, thiamphenicol,... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4298825