Acyloxyalkyl carbamate prodrugs, methods of synthesis and use

Details Acyloxyalkyl carbamate prodrugs, methods of synthesis and use Acyloxyalkyl carbamate prodrugs, methods of synthesis and use

2007-10-24

2009-08-11

Zucker, Paul A (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

Reexamination Certificate

active

07572830

ABSTRACT:
The disclosures herein relate generally to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, pharmaceutical compositions thereof, methods of making prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, methods of using prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, and pharmaceutical compositions thereof for treating or preventing common diseases and/or disorders such as spasticity and/or acid reflux disease. The disclosures herein also relate to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof which are suitable for oral administration and to sustained release oral dosage forms thereof.

REFERENCES:
patent: 2996431 (1961-08-01), Barry
patent: 3139383 (1964-06-01), Neville
patent: 3402240 (1968-09-01), Cain et al.
patent: 3471548 (1969-10-01), Keberle et al.
patent: 3634428 (1972-01-01), Keberle et al.
patent: 3811444 (1974-05-01), Heller et al.
patent: 3845770 (1974-11-01), Theeuwes et al.
patent: 3916899 (1975-11-01), Theeuwes et al.
patent: 3962414 (1976-06-01), Michaels
patent: 3992518 (1976-11-01), Chien et al.
patent: 4036829 (1977-07-01), Ferres et al.
patent: 4063064 (1977-12-01), Saunders et al.
patent: 4066747 (1978-01-01), Capozza
patent: 4070347 (1978-01-01), Schmitt
patent: 4079038 (1978-03-01), Choi et al.
patent: 4083949 (1978-04-01), Benedikt
patent: 4088864 (1978-05-01), Theeuwes et al.
patent: 4093709 (1978-06-01), Choi et al.
patent: 4094992 (1978-06-01), Kaplan et al.
patent: 4126684 (1978-11-01), Robson et al.
patent: 4200098 (1980-04-01), Ayer et al.
patent: 4285987 (1981-08-01), Ayer et al.
patent: 4421736 (1983-12-01), Walters
patent: 4434153 (1984-02-01), Urquhart et al.
patent: 4721613 (1988-01-01), Urquhart et al.
patent: 4752470 (1988-06-01), Mehta
patent: 4760057 (1988-07-01), Alexander
patent: 4780463 (1988-10-01), Sunshine et al.
patent: 4816263 (1989-03-01), Ayer et al.
patent: 4820523 (1989-04-01), Shtohryn et al.
patent: 4853229 (1989-08-01), Theeuwes
patent: 4916230 (1990-04-01), Alexander
patent: 4996058 (1991-02-01), Sinnreich
patent: 5006560 (1991-04-01), Kreutner et al.
patent: 5091184 (1992-02-01), Khanna
patent: 5229135 (1993-07-01), Philippon et al.
patent: 5466811 (1995-11-01), Alexander
patent: 5684018 (1997-11-01), Alexander
patent: 5698155 (1997-12-01), Grosswald et al.
patent: 5719185 (1998-02-01), Bountra et al.
patent: 5773592 (1998-06-01), Mills
patent: 6051734 (2000-04-01), Wildervanck et al.
patent: 6117908 (2000-09-01), Andrews et al.
patent: 6375987 (2002-04-01), Farah et al.
patent: 6379700 (2002-04-01), Joachim et al.
patent: 6627223 (2003-09-01), Percel et al.
patent: 7109239 (2006-09-01), Gallop et al.
patent: 2002/0151529 (2002-10-01), Cundy et al.
patent: 2003/0031711 (2003-02-01), Fara et al.
patent: 2003/0171303 (2003-09-01), Gallop et al.
patent: 2003/0176398 (2003-09-01), Gallop et al.
patent: 2003/0228644 (2003-12-01), Mills
patent: 2004/0006132 (2004-01-01), Gallop et al.
patent: 2004/0014940 (2004-01-01), Raillard et al.
patent: 4224342 (1994-01-01), None
patent: 4424975 (1996-01-01), None
patent: 0130119 (1984-06-01), None
patent: 0463969 (1995-02-01), None
patent: 1178034 (2002-02-01), None
patent: 01319466 (1989-12-01), None
patent: WO 98/22110 (1998-05-01), None
patent: WO 01/08675 (2001-02-01), None
patent: WO 01/26638 (2001-04-01), None
patent: WO 01/26638 (2001-04-01), None
patent: WO 01/90052 (2001-11-01), None
patent: WO 02/096404 (2002-12-01), None
patent: WO 02/100347 (2002-12-01), None
patent: WO 02/100347 (2002-12-01), None
patent: WO 03/011255 (2003-02-01), None
Alderman, “A Review of cellulose Ethers in Hydrophilic Matrices dor Oral controlled-Release Dosage Forms,”Int. J. Pharm. Tech.&Prod. Mfr.1984, 5(3) 1-9.
Astudillo et al., “A Very Simple Oxidation of Olefins and Ketones with UHP-Maleic Anhydride,”Heterocycles1993, 36, 1075-1080.
Balicki et al., “Mild and Efficient Conversion of Nitriles to Amides with Basic Urea-Hydrogen Peroxide Adduct,”Synth. Commun.1993, 23, 3149.
Bamba et al., “Release Mechanisms in Gelforming Sustained Release Preparatins,”Int. J. Phar.1979, 2, 307.
Berthelot et al., “3-Thienyl- and 3-futylaminobutyric acids. Synthesis and binding GABAB receptor studies,”J. Med. Chem.1991, 34, 2557-2560.
Berthelot et al., “Synthesis and pharmacological evaluation of gamma-aminobutyric acid analogues. New ligand for GABAB sites,”J. Med. Chem.1987, 30, 743-746.
Bowery, “GABAB receptors and their significance in mammalian pharmacology,”Trends Pharmacol. Sci.1989, 10, 401-407.
Butcher “Carbamate Esters: a Simple, Mild Method of Formation,”SynLett, 1994, 825-826.
Cercos-Fortea et al., “Influence Of Leucine On Intestinal Baclofen Absorption As A Model Compound Of Neutral Alpha-Aminoacids,”Biopharm. Drug. Disp.1995, 16, 563-577.
Chenevert et al., “Chemoenzymatic Synthesis of Both Enantiomers of Baclofen,”Tetrahedron Lett.1991, 32, 4249-4250.
Ciccaglione et al., “Effect of acute and chronic administration of the GABABagonist baclofen on 24 hour pH metry and symptoms in control subjects and in patients with gastro-oesophageal reflux disease,”Gut2003, 52, 464-470.
Coleman et al., “Polymer Review: A Practical Guide to Polymer Miscibility,”Polymers1990, 31, 1187-1231.
Cooper et al., “Oxidation Reactions Using Urea-Hydrogen Peroxide: A Sage Alternative to Anhydrous Hydrogen Peroxide,”Synlett.1990, 533-535.
Deguchi et al., “Study on brain interstitial fluid distribution and blood-brain barrier transport of baclofen in rats by microdialysis,”Pharm. Res.1995, 12, 1838-1844.
During et al., “Controlled release of dopamine from a polymeric brain implant: in vivo characterization,” 1989,Ann. Neurol.25:351.
Fincher, “Particle Size of Drugs and Its Relationship to Absorption and Activity,”J. Pharm. Sci.1968, 57, 1825-1835.
Fromm et al., “Comparison of L-baclofen and racemic baclofen in trigeminal neuralgia,”Neurology1987, 37, 1725-1728.
Goodson, “Medical Applications of Controlled Release,” vol. 2, pp. 115-138 (1984).
Guillon et al. “Pharmacological Evaluation of New Baclofen Derivatives,” Pharm. Pharmacol. Commun. 1999, 5, 243-247.
Herdeis et al., “Synthesis of Homochiral R-Baclofen from S-Glutamic Acid,”Tetrahedron Asymmetry1992, 3, 1213-1221.
Hoes et al., “The Application of Drug-Polymer Conjugates in Chemotherapy,”Drug Carreir Systems1989, 9, 57-110.
Howard et al., “Intracebral drug delivery in rats with lesion-induced memory deficits,”J. Neurosurg.1989 71(1):105-112.
Krach, “Pharmacotherapy Of Spasticity: Oral Medications And Intrathecal Baclofen,”J. Child Neurol.2001, 16, 31-36.
Katz, “Management of Spasticity,”Am. J. Phys. Med. Rehabil.1988, 2, 108-116.
Kayser et al., “Designer Yeast: an Enantioselective Oxidizing Reagent for Organic Synthesis.”SynLett,1999, 1:153.
Krogsgaard-Larsen, “GABA Synaptic Mechanisms: Stereochemical And Conformational Requirements,”Med. Res. Rev.1988, 8, 27-56.
Langer et al.,, “Chemical and Physical Structure of Polymers as Carriers for Controlled Release of Bioactive Agents: A Review,”J Macromol. Sci. Rev. Macromol Chem.1983, 23:61.
Langer, “New Method of Drug Delivery,” 1990,Science249:1527-1533.
Leisen et al., “Lipophilicities of baclofen ester prodrugs correlate with affinities to the ATP-dependent efflux pump P-glycoprotein: relevance for their permeation across the blood-brain barrier?”Phar. Res.2003, 20, 772-778.
Leong et al., “Polymeric Controlled Drug Delivery,”Adv. Drug Delivery Rev.1987, 1, 199-233.
Levy et al., “Inhibition of Calcification of Bioprosthetic Heart Valves by Local Controlled-Release Diphosphonate,”Science1985 228: 190-192.
List, et al., “The

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