Process for preparing malathion for pharmaceutical use

Details Process for preparing malathion for pharmaceutical use Process for preparing malathion for pharmaceutical use

2011-07-12

2011-07-12

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...

Reexamination Certificate

active

07977324

ABSTRACT:
The present invention provides a process for preparing a highly pure form of malathion having a reduced level of toxic impurities. In addition, the malathion prepared by the process of this invention is storage stable. The level of toxic impurities in the malathion, e.g., isomalathion, O,O,S-trimethyl phosphorodithioate (MeOOSPS), O,O,S-trimethyl phosphorothioate (MeOOSPO), O,S,S-trimethyl phosphorodithioate (MeOSSPO), malaoxon, isomalathion, diethyl fumarate, methyl malathion, dimethyl malathion, O,O-methyl,ethyl-S-(1,2-dicarboethoxy)ethyl-phosphorodithioate are lower than that of any other commercial preparation of malathion that may be used for pharmaceutical purposes.

REFERENCES:
patent: 2578652 (1951-12-01), Cassaday
patent: 2863902 (1958-12-01), Santay
patent: 2879284 (1959-03-01), Divine et al.
patent: 2931825 (1960-04-01), Lutz
patent: 2962521 (1960-11-01), Usui
patent: 2980723 (1961-04-01), Frank et al.
patent: 3309432 (1967-03-01), English
patent: 3352664 (1967-11-01), Nolan et al.
patent: 3396223 (1968-08-01), Stark, Jr.
patent: 3403201 (1968-09-01), Adrian et al.
patent: 3440305 (1969-04-01), Divine
patent: 3463841 (1969-08-01), Backlund et al.
patent: 3470272 (1969-09-01), Melton
patent: 3515782 (1970-06-01), Nolan
patent: 3714301 (1973-01-01), Thomsen
patent: 4049755 (1977-09-01), Bianchi et al.
patent: 4367180 (1983-01-01), Rouy et al.
patent: 4520013 (1985-05-01), Nezat
patent: 4681964 (1987-07-01), Annarelli et al.
patent: 5783202 (1998-07-01), Tomlinson et al.
patent: 6103248 (2000-08-01), Burkhart et al.
patent: 6121478 (2000-09-01), Pedersen
patent: 6280729 (2001-08-01), Huang et al.
patent: 6500994 (2002-12-01), Brosch et al.
patent: 6521762 (2003-02-01), Keri et al.
patent: 6524602 (2003-02-01), Burkhart et al.
patent: 6562363 (2003-05-01), Mantelle et al.
patent: 6596291 (2003-07-01), Bell
patent: 6607716 (2003-08-01), Smith et al.
patent: 6689394 (2004-02-01), Van Scoik et al.
patent: 6806292 (2004-10-01), Riebel et al.
patent: 6939715 (2005-09-01), Beck et al.
patent: 2002/0009486 (2002-01-01), Godbey
patent: 2002/0048558 (2002-04-01), Niemiec et al.
patent: 2003/0036530 (2003-02-01), Bessette
patent: 2004/0024052 (2004-02-01), Gyuricza et al.
patent: 2005/0031547 (2005-02-01), Tamarkin et al.
patent: 2006/0121073 (2006-06-01), Goyal et al.
patent: 1541883 (1968-10-01), None
patent: 834814 (1960-05-01), None
patent: 2204243 (1988-11-01), None
patent: 2222949 (1990-03-01), None
patent: 86214 (1985-02-01), None
patent: 87602 (1985-12-01), None
patent: WO-03/066009 (2003-08-01), None
patent: WO/2006/017232 (2006-02-01), None
patent: WO/2006/017263 (2006-02-01), None
Meinking et al., Pediatric Dermatology, vol. 21, No. 6, pp. 670-674, 2004.
Nature's Mist, Skin Functioning and Dehydration, www.naturesmist.com, p. 1-4, 2003.
“A modern scourge parent scratch their heads over lice,” Consumer Reports, Feb. 1998.
Office Action issued by the USPTO on Feb. 18, 2009 for U.S. Appl. No. 11/179,719.
Office Action issued by the USPTO on Sep. 16, 2009 for U.S. Appl. No. 11/179,719.
Office Action issued by the USPTO on May 27, 2010 for U.S. Appl. No. 11/179,719.
Office Action Issued by the USPTO on Feb. 19, 2009 for U.S. Appl. No. 11/351,188.
Office Action issued by the USPTO on Sep. 21, 2009 for U.S. Appl. No. 11/351,188.
Office Action issued by the USPTO on May 27, 2010 for U.S. Appl. No. 11/351,188.
Al-Wakil et al., “Separation and Preconcentration of Malathion and Azamethiphos by Unloaded Polyurethane Foams,” Qatar University Science Journal, vol. 14(spec. issue), 1994. (Abstract Only).
Baker, Jr. et al., Epidemic Malathion Poisoning in Pakistan Malaria Workers, The Lancet, vol. 1, No. 8054, 1978.
Blasiak et al., “In Vitro Studies on the Genotoxicity of the Organophosphorus Insecticide Malathion and Its Two Analogues,” Mutat. Res., vol. 445, No. 2, pp. 275-283, 2003. (Abstract Only).
Imamura et al., “Pulmonary Toxicity of Phosphorothioate Impurities Found in Organophosphate Insecticides,” Pharmacology and Therapeutics, vol. 38, No. 3, pp. 419-427, 1988. (Abstract Only).
Liu et al., “Rapid Isolation with Sep-Pak C18 Cartridges and Wide Bore Capillary Gas Chromatography of Organophosphate Pesticides,” Forensic Science International, vol. 41, No. 1-2, pp. 67-72, 1989. (Abstract Only).
Lupea et al., “Addition of Dimethyl Dithiophosphate to Ethyl Maleate and Ethyl Fumarate,” Buletinul Stiintific si Tehnic al Institutului Politechnic Traian Vuia Timisoara, Seria Chimie, vol. 26, No. 1, pp. 51-60, 1981. (English Abstract Only).
Makarova et al., “Photometric Determination of Organophosphorus Pesticides After Separation By Thin Layer Chromatography,” Industr. Lab., vol. 40, No. 7, pp. 961-964, 1974. (Abstract Only).
Malathion, 1GM, Neat—Product No. PS86; Sigma-Aldrich Catalog, 2003; with Certificate of Analysis.
Malathion, Pestanal®, analytical standard, Sigma-Aldrich Catalog, 2006, with Certificate of Analysis.
Ovide (Malathion) Lotion, 0.5%, NDC 51672-5276-4, Jul. 2005.
Patel et al., “Manufacture of Malathion,” Pestic., Symp. (1968), Meeting Date 1964, pp. 69-72. (Abstract Only).
Polec et al., “Simple Syntheses of Malathion and Malaoxon Enantiomers, and Isomalathion Diastereoisomers: Toxicity-Configuration Relationship,” Pesticide Science, vol. 53, No. 2, pp. 165-171, 1998. (Abstract Only).
Polec et al., “Synthesis of Malathion Enantiomers,” Organika, vol. date 1995, pp. 7-15, 1996. (English Abstract Only).
Reimschussel et al., “Radioisotopic Studies On the Content and Conversion Rates of Toxic Impurities in Malathion,” Pesticides: food and environmental implications, Proceedings of a symposium held in Neuherberg, Nov. 24-27, 1987, pp. 301-303, Published 1988. (Abstract Only).
Shvetsova-Shilovskaya et al., “Purification of Technical Carbophos,” Khimicheskaya Promyshlennost, vol. 47, No. 11, p. 869, 1971. (English Abstract Only).
Supplementary European Search Report issued in EP Application No. 06774561 on Jun. 4, 2010.
Talcott et al., “Inactivation of Esterases by Impurities Isolated from Technical Malathion,” Toxicology and Applied Pharmacology, vol. 49, No. 1, pp. 107-112, 1979. (Abstract Only).
Toia et al., “Identification and Toxicological Evaluation of Impurities in Technical Malathion and Fenthion,” J. Agric. Food Chem., vol. 28, No. 3, pp. 599-604, 1980. (Abstract A Only).
Toia et al., “Identification and Toxicological Evaluation of Impurities in Technical Malathion and Fenthion,” J. Agric. Food Chem., vol. 28, No. 3, pp. 599-604, 1980. (Abstract B Only).
Umezu, “Toxicity of Malathion to Mammals Potentiation of Toxicity by Impurities,” Kagaku To Seibutsu (Chem. Biol.) vol. 16, No. 5, pp. 302-304, 1978. (English Abstract Only).
USP Monographs: Malathion Lotion, 2008.
USP Monographs: Malathion, 2008.
Wilkins et al., “A Study of the Trans-Esterification Products of Malathion by Capillary Gas Chromatography-Mass Spectrometry,” Pesticide Science, vol. 20, No. 4, pp. 259-270, 1987. (Abstract Only).
Retro Search, Malathion Impurities, Sep. 13, 2005. (Collection of Abstracts).
Retro Search, Malathion Impurity, Sep. 13, 2005. (Collection of Abstracts).
Stability Results for Malathion Lotion, Aug.-Nov. 2004.
Certificates of Analysis, malathion USP, Cheminova, Jun. 1999-Oct. 2002.
“Impurities of maldison,” Review Scope Document Maldison, p. 6-11, Feb. 2003.
EPA 1600 Methods, p. 213, 2003.
EPA 8000 Methods, pp. 238-239, 2003.
“Occupational Exposure to Organophosphate and Carbamate Insecticides.” Department of Health and Human Services, p. 1-5, 2003.
Subpart II. B. Pharmacology and Toxicology, p. 62-123, 2003.
“Malathion Reregistration Eligibility Document: Environmental Fate and Effects Chapter,” United States Environmental Protection Agency, p. 1-52, 2004.
Ovide (Malathion) Lotion, 0.5%, NDA 18-613, vol. 1 of 21, 1980.
Prioderm Lotion NDA 18-613, Replacement Pages, Book 1 of 3, 1980.
Ovide

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