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

2011-05-03

2011-05-03

Shiao, Rei-tsang (Department: 1628)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Phosphorus containing other than solely as part of an...

C558S177000, C558S178000

Reexamination Certificate

active

07935686

ABSTRACT:
Acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof, pharmaceutical compositions comprising acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof, methods of making prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof, methods of using prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof and pharmaceutical compositions thereof for treating or preventing diseases or disorders such as spasticity or gastroesophageal reflux disease are disclosed. Acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof and sustained release oral dosage forms thereof, which are suitable for oral administration, are also disclosed.

REFERENCES:
patent: 2996431 (1953-12-01), Barry
patent: 3139383 (1964-06-01), Neville
patent: 3402240 (1968-09-01), Cain et al
patent: 3803112 (1974-04-01), Engelhardt 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), Michales
patent: 3992518 (1976-11-01), Chien 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: 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), Urguhart et al.
patent: 4656298 (1987-04-01), Dingwall et al.
patent: 4721613 (1988-01-01), Urguhart et al.
patent: 4752470 (1988-06-01), Mehta
patent: 4816263 (1989-03-01), Ayer et al.
patent: 4820523 (1989-04-01), Shtohryn et al.
patent: 4853229 (1989-08-01), Theeuwes
patent: 4996058 (1991-02-01), Sinnreich
patent: 5006560 (1991-04-01), Kreutner et al.
patent: 5013863 (1991-05-01), Baylis et al.
patent: 5051524 (1991-09-01), Baylis et al.
patent: 5091184 (1992-02-01), Khanna
patent: 5229135 (1993-07-01), Philippon et al.
patent: 5229379 (1993-07-01), Marescaux et al.
patent: 5281747 (1994-01-01), Hall et al.
patent: 5300679 (1994-04-01), Baylis et al.
patent: 5332729 (1994-07-01), Mickel et al.
patent: 5376684 (1994-12-01), Mickel
patent: 5407922 (1995-04-01), Marescaux et al.
patent: 5424441 (1995-06-01), Mickel et al.
patent: 5461040 (1995-10-01), Hall et al.
patent: 5545631 (1996-08-01), Marescaux et al.
patent: 5567840 (1996-10-01), Hall et al.
patent: 5698155 (1997-12-01), Grosswald et al.
patent: 5719185 (1998-02-01), Bountra et al.
patent: 6117908 (2000-09-01), Andrews et al.
patent: 6171615 (2001-01-01), Roussin 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: 6664069 (2003-12-01), Andrews et al.
patent: 7319110 (2008-01-01), Lange et al.
patent: 7585996 (2009-09-01), Gallop et al.
patent: 7749985 (2010-07-01), Gallop et al.
patent: 2002/0187977 (2002-12-01), Pearlman et al.
patent: 2003/0162754 (2003-08-01), Ligon
patent: 2006/0111325 (2006-05-01), Gallop
patent: 2006/0111439 (2006-05-01), Gallop
patent: 2008/0146526 (2008-06-01), Gallop et al.
patent: WO 00/57862 (2000-10-01), None
patent: WO 01/08675 (2001-02-01), None
patent: WO 01/26638 (2001-04-01), None
patent: WO 01/42252 (2001-06-01), None
patent: WO 01/54481 (2001-08-01), None
patent: WO 02/096404 (2002-12-01), None
patent: WO 02/100347 (2002-12-01), None
patent: WO 02/100392 (2002-12-01), None
patent: WO 02/100823 (2002-12-01), None
patent: WO 02/100869 (2002-12-01), None
patent: WO 02/100870 (2002-12-01), None
patent: WO 02/100871 (2002-12-01), None
patent: WO 03/011255 (2003-02-01), None
patent: WO 04/000855 (2003-12-01), None
patent: WO 04/000856 (2003-12-01), None
patent: WO 2005/010011 (2005-02-01), None
patent: WO 2005/066122 (2005-07-01), None
patent: WO 2006/050471 (2006-05-01), None
patent: WO 2008/033572 (2008-03-01), None
Alderman, A review of cellulose ethers in hydrophilic matrices for oral controlled-release dosage forms. Int. J. Pharm. Tech. & Prod. Mfr. 1984, 5(3), 1-9.
Bamba et al., Release mechanisms in gelforming sustained release preparations. Int. J. Pharm. 1979, 2, 307-315.
Bardgett et al., NMDA receptor blockade and hippocampal neuronal loss impair fear conditioning and position habit reversal in C57BI/6 mice. Brain Res Bull 2003, 60(1-2), 131-142.
Bowery, GABAB receptors and their significance in mammalian pharmacology. Trends Pharmacol. Sci. 1989, 10, 401-407.
Brown et al., Conditioned fear as revealed by magnitude of startle response to an auditory stimulus. J Expt'l Psychol 1951, 41(5), 317-28.
Cange et al., Baclofen-mediated gastro-oesphageal acid reflux control in patients with established reflux disease. Aliment. Pharmacol. Ther. 2002,16, 869-873.
Cercos-Fortea et al., Influence of leucine on intestinal baclofen absorption as a model compound of neutral α-aminoacids. Biopharm. Drug. Disp. 1995, 16, 563-577.
Ciccaglione et al., Effect of acute and chronic administration of the GABAB agonist baclofen on 24 hour pH metry and symptoms in control subjects and in patients with gastro-oesphageal reflux disease. Gut 2003, 52, 464-470.
Coleman et al., A practical guide to polymer miscibility. Polymers 1990, 31, 1187-1231.
Conn (ed.), Handbook of models for human ageing. Amsterdam; Boston, Elsevier Academic Press, 2006.
Cryan and Momereau, In search of a depressed mouse: utility of models for studying depression-related behavior in genetically modified mice. Mol Psychiatry 2004, 9(4), 326-57.
Cryan et al., Assessing antidepressant activity in rodents: recent developments and future needs. Trends Pharmacol Sci 2202, 23(5), 238-45.
Datamonitor, Commercial and Pipeline Perspectives: Upper GI Disorders (No. DMHC2005, Sep. 2004, p. 147): Datamonitor.
Deguchi et al., Study on brain interstitial fluid distribution and blood-brain barrier transport of baclofen in rats by microdialysis. Pharm. Res. 1995, 12(12), 1838-1844.
Deprele and Montchamp, Triethylborane-initiated room temperature radical addition of hypophosphites to olefins: synthesis of monosubstituted phosphinic acids and esters. J Org Chem 2001, 66(20), 6745-55.
Dingwall et al., Diethoxymethylphosphonites and phosphinates. Intermediates for the synthesis of alpha, beta- and gamma-aminoalkylphosphonous acids. Tetrahedron 1989, 45(12), 3787-3808.
During et al., Controlled release of dopamine from a polymeric brain implant: in vivo characterization. Ann. Neurol. 1989, 25(4), 351-6.
Fincher, Particle size of drugs and its relationship to absorption and activity. J. Pharm. Sci. 1968, 57(11), 1825-1835.
Froestl et al., Phosphinic acid analogues of GABA. 1. New potent and selective GABAB agonists. J. Med. Chem. 1995, 38(17), 3297-3312.
Froestl et al., SGS742: the first GABAB receptor antagonist in clinical trials. Biochem Pharmacol 2004, 68(8), 1479-87.
Getova et al., Effects of GABAB receptor antagonists on learning and memory retention in a rat model of absence epilepsy. Eur J Pharmacol 1997, 320(1), 9-13.
Gijsman et al., Antidepressants for bipolar depression: a systematic review of randomized, controlled trials. Am J Psychiatry 2004, 161(9), 1537-47.
Gleiter et al., Pharmacokinetics of CGP 36,742, and orally active GABAB antagonist, in humans. J Clin Pharmacol 1996, 36(5), 428-38.
Goodson, in “Medical Applications of Controlled Release,” vol. 2, ed. Langer and Wise, CRC Press, Inc., Boca Raton, FL, 1964, pp. 115-138 (1984).
Greene and Wuts, “Protective Groups in Organic Chemistry,” 2nd ed., John Wiley & Sons, Inc., New York, 1991.
Harrison and Harrison, “Compendium of Synthetic Organic Methods,” vols. 1-8 Wiley-Interscience, New York, 1971-1996.
Helm et al., GABAB receptor antagonist SG742 improves spatial memory and reduces protein binding to the cAMP res

Affiliated with

Also associated with

Rating

Acyloxyalkyl carbamate prodrugs, methods of synthesis, and use does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Acyloxyalkyl carbamate prodrugs, methods of synthesis, and use, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Acyloxyalkyl carbamate prodrugs, methods of synthesis, and use will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2691426