Forming Phosphorus To Nitrogen Bond Patents (Class 558/138)
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Publication number: 20130253181Abstract: Disclosed herein are methods of preparing a phosphorothioate nucleotide analog, which are useful in treating diseases and/or conditions such as viral infections.Type: ApplicationFiled: March 11, 2013Publication date: September 26, 2013Applicants: VERTEX PHARMACEUTICALS INC., ALIOS BIOPHARMA, INC.Inventors: Vladimir Serebryany, Jyanwei Liu, Leonid Beigelman, Young Chun Jung
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Patent number: 6441223Abstract: A process for oxidizing a hydroxymethylphosphonic acid compound to produce a formylphosphonic acid compound is described. The oxidation reaction is carried out in the presence of an oxidant and a catalyst. For example, hydroxymethylphosphonic acid (HMPA) is oxidized by oxygen or hydrogen peroxide in the presence of a copper-containing catalyst to give formylphosphonic acid (FPA). Formylphosphonic acid can then be reacted with glycine to produce a condensation product which, upon hydrogenation, yields glyphosate. Glyphosate can be incorporated into various formulations for use as a herbicide. In addition to glycine, formylphosphonic acid can also be reacted with ammonia, ethanolamine, or other primary amines to form a precursor compound, which can be converted to glyphosate.Type: GrantFiled: November 30, 2000Date of Patent: August 27, 2002Assignee: Monsanto Technology LLCInventor: Thaddeus S. Franczyk, II
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Patent number: 6291700Abstract: Sterically hindered phosphoramidates such as N,N′-bis[di-(2,6-xylyl)phosphoryl]piperazine are prepared by the reaction of a sterically hindered diaryl chlorophosphate, such as di-(2,6-xylyl) chlorophosphate, with a basic nitrogen compound containing at least two basic N—H groups, preferably a heterocyclic compound such as piperazine, in the presence of an acid acceptor such as triethylamine. The reaction is conducted in methylene chloride or an aromatic hydrocarbon such as toluene as solvent. If an aromatic hydrocarbon is employed, there is also present at least one dipolar aprotic nitrogen compound, such as 4-dimethylaminopyridine, in an amount effective to increase the reaction rate.Type: GrantFiled: March 30, 2000Date of Patent: September 18, 2001Assignee: General Electric CompanyInventors: James Anthony Cella, John Robert Campbell, Paul Edward Howson
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Patent number: 6277988Abstract: Sterically hindered phosphoramidates such as N,N′-bis[di-(2,6-xylenoxy)phosphinyl]piperazine are prepared by the reaction of a sterically hindered diaryl chlorophosphate, such as di-(2,6-xylyl) chlorophosphate, with a basic nitrogen compound containing at least two basic N—H groups, preferably a heterocyclic compound such as piperazine, in a predominantly liquid, solvent-free reaction mixture. The reaction may be conducted in the melt or in the presence of a non-solvent carrier, typically an aliphatic hydrocarbon. An excess of the basic nitrogen compound is employed as an acid acceptor.Type: GrantFiled: February 29, 2000Date of Patent: August 21, 2001Assignee: General Electric CompanyInventors: John Robert Campbell, James Anthony Cella, Gregory Ronald Gillette, John Edward Kochanowski, Matthew Ladd Reitz
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Patent number: 6218563Abstract: The present invention provides a process for preparing a cyanophosphonamide comprising contacting phosphoric anhydride and a cyanide, preferably in the presence of a Lewis base, to produce a cyanophosphonate intermediate, and subsequently contacting the cyanophosphonate intermediate with an amino compound.Type: GrantFiled: November 29, 1999Date of Patent: April 17, 2001Assignee: Monsanto CompanyInventors: Patrick J. Lennon, Serge G. Vulfson
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Patent number: 6191276Abstract: Sterically hindered phosphoramidates such as N,N′-bis[di-(2,6-xylenoxy)phosphoryl]piperazine are prepared by the reaction of a sterically hindered diaryl chlorophosphate, such as di-(2,6-xylyl) chlorophosphate, with a basic nitrogen compound containing at least two basic N-H groups, preferably a heterocyclic compound such as piperazine, in the presence of calcium oxide as an acid acceptor. The reaction is conducted in the presence of at least one dipolar aprotic solvent.Type: GrantFiled: February 23, 2000Date of Patent: February 20, 2001Assignee: General Electric CompanyInventor: James Anthony Cella
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Patent number: 6127566Abstract: The present invention provides a continuous process for making O,O-dimethyl phosphoroamidothioate. In accordance with this process, O,O-dimethyl phosphorochloridothioate is reacted with ammonia and sodium hydroxide; addition of the sodium hydroxide controls the pH of the reaction mixture. The formed reaction mixture contains an aqueous phase and an organic phase. The organic phase of the reaction mixture is separated from the aqueous phase; a second organic phase is solvent extracted from the aqueous phase; and the resultant O,O-dimethyl phosphoroamidothioate is isolated from the combined organic phases via vacuum solvent stripping. In an embodiment of the present invention, the reaction of O,O-dimethyl phosphorochloridothioate with ammonia and sodium hydroxide is carried out in the presence of a solvent.Type: GrantFiled: September 16, 1998Date of Patent: October 3, 2000Assignee: Bayer CorporationInventors: Vidyanatha A. Prasad, Donald K. Smith, David L. Meyer, Jonathan D. Spicher, Scott P. Hensley
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Patent number: 4885286Abstract: A novel phosphonamidothionate derivative represented by the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in the disclosure. The present novel compound has excellent properties with respect to not only pesticidal activity but also maintenance of the pesticidal activity over a prolonged period of time after application. The present novel compound can be prepared by a new unique process in which the direct phosphorylation of a carbamate compound is involved.Type: GrantFiled: February 19, 1988Date of Patent: December 5, 1989Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hiromichi Yoshikawa, Teruyuki Misumi
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Patent number: 4642366Abstract: A process is provided for the preparation of diaryl methylphosphonates through the reaction of triaryl phosphites with methanol in the presence of a catalytic quantity of methyl iodide. The reaction is conducted at a temperature of from about 170.degree. C. to about 250.degree. C. New and useful derivatives are produced by reaction of the diaryl methylphosphonates with polyols or amines.Type: GrantFiled: February 13, 1986Date of Patent: February 10, 1987Assignee: Stauffer Chemical CompanyInventors: Milton L. Honig, Edward D. Weil
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Patent number: 4587362Abstract: A process is provided for the preparation of diaryl methylphosphonates through the reaction of triaryl phosphites with methanol in the presence of a catalytic quantity of methyl iodide. The reaction is conducted at a temperature of from about 170.degree. C. to about 250.degree. C. New and useful derivatives are produced by reaction of the diaryl methylphosphonates with polyols or amines.Type: GrantFiled: March 5, 1984Date of Patent: May 6, 1986Assignee: Stauffer Chemical CompanyInventors: Milton L. Honig, Edward D. Weil