Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2005-12-22
2009-11-17
Kumar, Shailendra (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C514S019300, C514S171000, C514S295000, C514S299000, C514S397000, C558S276000
Reexamination Certificate
active
07619110
ABSTRACT:
The present invention provides a prodrug of propofol and crystalline forms thereof, methods of making the propofol prodrug and crystalline forms thereof, pharmaceutical compositions of the propofol prodrug and crystalline forms thereof, methods of using the propofol prodrug and crystalline forms thereof and pharmaceutical compositions thereof to treat diseases or disorders such as headache pain, post-chemotherapy or post-operative surgery nausea and vomiting, neurodegenerative disorders, and mood disorders.
REFERENCES:
patent: 3845770 (1974-11-01), Theeuwes et al.
patent: 3916899 (1975-11-01), Theeuwes et al.
patent: 4765539 (1988-08-01), Noakes et al.
patent: 4962885 (1990-10-01), Coffee
patent: 5112598 (1992-05-01), Biesalski
patent: 5556611 (1996-09-01), Biesalski
patent: 5698155 (1997-12-01), Grosswald et al.
patent: 5950619 (1999-09-01), van der Linden et al.
patent: 5954047 (1999-09-01), Armer et al.
patent: 5970974 (1999-10-01), van der Linder et al.
patent: 6254853 (2001-07-01), Hendler et al.
patent: 6362234 (2002-03-01), Hendler
patent: 2001/0025035 (2001-09-01), Stella et al.
patent: 2005/0004381 (2005-01-01), Gallop et al.
patent: WO 94/12285 (1994-06-01), None
patent: WO 94/12285 (1994-06-01), None
patent: WO 94/14543 (1994-07-01), None
patent: WO 94/14543 (1994-07-01), None
patent: WO 95/26234 (1995-10-01), None
patent: WO 95/26235 (1995-10-01), None
patent: WO 95/32807 (1995-12-01), None
patent: WO 99/58555 (1999-11-01), None
patent: WO 99/58555 (1999-11-01), None
patent: WO 00/48572 (2000-08-01), None
patent: WO 00/54588 (2000-09-01), None
patent: WO 02/13810 (2002-02-01), None
patent: WO 2004/033424 (2004-04-01), None
patent: WO 2005/004381 (2005-01-01), None
West, Anthony R., Solid State Chemistry and its Applications, Wiley, New York, 1988, pp. 358 & 365.
S.R.Vippagunta, H.G.Brittain, D.J.W.Grant, “Crystalline solids”, Advanced Drug Delivary Reviews, 2001, 48, 3-26.
Grunberg et al., “Palosetron: a Unique 5-HT3-receptor Antagonist For the Prevention of Chemotherapy-Induced Emesis,”Expert. Opin., 2003, 4(12), 2297-2303.
The Merck Index, 2001, 13thEdition, pp. 156, 808, 600, 1225, 1741-1742.
U.S. Appl. No. 10/766,990, filed Jan. 28, 2004, Gallop et al.
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.
Altomare et al., “Highly Water-Soluble Derivatives of Anaesthetic Agent Propofol: in vitro and invitro evaluation of cyclic amino esters,”European Journal of Pharmaceutical Sciences, 2003, 20, 1, 17-26.
Anderson et al., “α-Amino Acid Phenolic Ester Derivatives: Novel Water-Soluble General Anesthetic Agents Which Allosterically Modulate GABAAReceptors,”J. Med. Chem. 2001, 44, 3582-3591.
Balimane et al., “Involvement of multiple transporters in the oral absorption of nucleoside analogues,”Adv Drug Deliv Rev. Oct. 18, 1999;39(1-3):183-209.
Bamba et al., “Release Mechanisms in Gelforming Sustained Release Preparations,”Int. J. Pharm. 1979, 2, 307.
Banaszczyk et al., “Propofol Phosphate, a Water-Soluble Propofol Prodrug: In Vivo Evaluation,”Anesth. Analg. 2002, 95, 1285-1292.
Beilstein Handbook of Organic Chemistry, Beilsein Institute of Organic Chemistry, Frankfurt, Germany.vol. 27, Part 26, 1979.
Borgeat et al., “Preliminary Communication: Adjuvant Propofol Enables Better Control of Nausea and Emesid Secondary to Chemotherapy for Breast Cancer,”Can. J. Anaesth. 1994, 41, 1117-1119.
Borgeat et al., “Propofol improves patient comfort during cisplatin chemotherapy. A pilot study,”Oncology1993, 50, 456-459.
Briggs et al., “An adverse reaction to the administration of disoprofol (Diprivan),”Anaesthesia1982, 37, 1099-1101.
Brooker et al., “Propofol Maintenance to Reduce Postoperatiove Emesis in Thyroidectomy Patients: A Group Sequential Comparison with Isoflurane/Nitrous Oxide,”Anaesth. Intensive Care1998, 26, 625-629.
Brown et al., “Role of Propofol in Refractory Status Epilepticus,”Pharmacother. 1998, 32, 1053-1059.
De la Cruz et al., “The Effect of Propofol on Oxidative Stress in Platelets from Surgical Patients,”Anesth. Analg. 1999, 89, 1050-1055.
During et al., “Controlled release of dopamine from a polymeric brain implant: in vivo characterization,” 1989,Ann. Neurol. 25:351.
Feiser et al., “Reagents for Organic Synthesis,” vols. 1-17, Wiley Interscience, vol. 22, 2004.
Feiser et al., “Reagents for Organic Synthesis,” vols. 1-17, Wiley Interscience, vol. 2, 2004.
Gan et al., “Determination of Plasma Concentrations of Propofol Associated with 50% Reduction in Postoperative Nausea,”Anesthesiology, 1997, 87, 779-784.
Gennaro, “Remington's Pharmaceutical Sciences,” Philadelphia College of Pharmacy and Science, 19th Edition, 1995.
Greene et al.Protective groups in Organic Chemistry, Wiley, 2nded., 1991.
Harrison et al.,Compendium of Synthetic Organic Methods, vols. 1-8, John Wiley and Sons, 1971-1996.
Hasan et al., “Comparison of the Effects of the Propofol and Thiopental on the Pattern of Maximal Electroshock Seizures in a Rat,”Pharmacol. Toxicol. 1994, 74, 50-53.
Holtkamp et al., “Propofol in subanesthetic doses terminates status epilepticus in a rodent model,”Ann. Neurol. 2001, 49, 260-263.
Howard et al., “Intercerebral Drug Delivery in Rats with Lesion-Induced Memory Deficits,” 1989,J. Neurosurg. 71:105-112.
Krusz et al., “Intravenous Propofol: Unique Effectiveness in Treating Intractable Migraine,”Headache2000, 40, 224-230.
Kuisma et al., “Propofol in Prewhospital Treatment of Convulsive Status Epilepticus,”Epilepsia1995, 36, 1241-1243.
Langer and Wise (eds.), Medical Application of Controlled Release, CRC Pres. Boca Ranton, Florida, 1974.
Langer et al., “Chemical and Physical Structure of Polymers as Carriers for Controlled Relaease of Bioactive Agents: A Review,”J Macromol. Sci. Rev. Macromol Chem. 1983, 23:61.
Langley et al., “Propofol. A review of its pharmacodynamic and pharmacokinetic properties and use as an intravenous anaesthetic,”Drugs1988, 35, 334-372.
Larock,Comprehensive Organic Chemistry, Wiley Interscience, 1991.
Lee et al., “Inhibitors of Acyl-Coa: Cholesterosl O-Acyl Transferase (ACAT) as Hypocholeserolemic Agents. CI-1011: An Acyl Sulfamate with Unique Cholsterol-Lowering Activity in Animals Fed Noncholesterol-Supplemented Diets,”Journal of Medicinal Chemistry,An American Chemical Society, vol. 39, No. 26, 1996, 5031-5034.
Levy et al., “Inhibition of Calcification of Bioprosthetic Heart Valves by Local Controlled-Release Diphosphonate,”Science1985 228: 190-192.
March,Advance Organic Chemistry, Wiley Interscience, 1991.
Murphy et al., “The Antioxidant Potential of Propofol (2,6-Diisopropylphenol),”Br. J. Anaesth. 1992, 68,613-618.
Paquette,Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, 1995.
Picard et al,“Prevention of Pain on Injection with Propofol: A Quantitative Systematic Review,” 2000, 90, 963-969.
Pop et al., “Synthesis and Preliminary Pharmacological Evaluation of Some Chemical Delivery Systems of 2,6-Diisopropylphenol (Propofol),”Med. Chem. Res. 1992, 2, 16-21.
Raleigh et al., “Searching for the Link Between Hypoxia and Poor Prognoses in Human Tumors,”Proc. Amer. Assoc. Cancer Research Annual Meeting, 1999, 40, 39.
Raoof et al., “In Vivo Assessment of Intestinal Hepatic, and Pulmonary First Pass Metabolism of Propofol in the Rat,”Pharm. Res. 1996, 13, 891-895.
Sagara et al., “Propofol Hemisuccinate Protects Neuronal Cells from Oxidative Injury,”J. Neurochem. 1999, 73, 2524-2530.
Saudek et al., “A Preliminary Trial of the Programmable Implantable Medication System for Insulin Delivery,”N. Engl. J. Med., 1989, 321: 574.
Dilip Usha
Gallop Mark A.
Sasikumar Vivek
Xu Feng
Dorsey & Whitney LLP
Katakam Sudhakar
Kumar Shailendra
XenoPort, Inc.
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