Converting A Phosphorus Ester Group To A P-xh Group, Wherein H Of -xh May Be Replaced By Substituted Or Unsubstituted Ammonium Or By A Group Ia Or Iia Light Metal, And Wherein X Is Chalogen And P May Be Trivalent Or Pentavalent Patents (Class 558/131)
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Patent number: 5985856Abstract: The present invention is drawn to water soluble derivatives aliphatic acid aromatic secondary and tertiary amine containing drugs. The present invention is further drawn to methods of making water soluble derivatives of aliphatic and aromatic secondary and tertiary amine containing drugs.Type: GrantFiled: December 30, 1998Date of Patent: November 16, 1999Assignee: University of KansasInventors: Valentino Stella, Jeffrey P. Krise, Jan J. Zygmunt, Ingrid Gunda Georg
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Patent number: 5981786Abstract: A process for producing a (meth)acrylate derivative including reacting a compound of formula (1) (wherein R.sup.1 is H or CH.sub.3 ; A is C.sub.1 -C.sub.10 alkylene; and p is 1 to 10) with a chloro-dioxaphosphorus compound of formula (2) (wherein q is 0 or 1) in the presence of a secondary amine of formula (3) (wherein R.sup.2 and R.sub.3 are each C.sub.3 -C.sub.8 alkyl, cycloalkyl, C.sub.6 -C.sub.9 aryl, arylalkyl, etc.) to produce a (meth)acrylate derivative of formula (4) and further reacting the same with a tertiary amine of formula (5) (wherein R.sup.4, R.sup.5 and R.sup.6 are each C.sub.1 -C.sub.4 alkyl etc.) to provide a (meth)acrylate derivative of formula (6).Type: GrantFiled: January 27, 1999Date of Patent: November 9, 1999Assignee: NOF CorporationInventors: Shigeru Kitano, Toshihiko Ohta, Hiroshi Suzuki, Akio Hayashi, Yoshishige Murata, Kazuo Matsuyama, Kenichiro Nakamoto
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Patent number: 5741923Abstract: An improved process for producing ethylenically unsaturated phosphate ester compounds, especially 2-(methacryloyloxyethyl)-2' (trimethylammoniomethyl) phosphate, (HEMA-PC) comprises a two step reaction in the first of which a phospholane reagent is reacted with a hydroxyl containing ethylenically unsaturated starting material, and in the second of which the intermediate formed in the first step is ring opened by reaction with trimethylamine to produce a zwitterionic product. In the process the two steps of the reaction are carried out in the same solvent with substantially no removal or addition of solvent after the first step. The solvent is preferably acetonitrile. The use of pure reagents avoids the production of undesirable by-products. The product is suitable for polymerising, for instance to provide cross-linked hydrogel copolymers used in ophthalmic applications.Type: GrantFiled: May 23, 1996Date of Patent: April 21, 1998Assignee: Biocompatibles LimitedInventors: Michael John Driver, Deborah Jane Jackson
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Patent number: 5705670Abstract: The invention relates to a process for the preparation of alkali metal salts of phosphonic acid monomethyl esters of the formula (I) ##STR1## in which R is (C.sub.1 -C.sub.14)-alkyl andMe is sodium or potassium,which comprises metering 20 to 50% strength alkali metal hydroxide solution, in a molar ratio of 1:1, into phosphonic acid dimethyl esters of the formula (II) ##STR2## optionally dissolved in water, the total amount of water from the alkali metal hydroxide solution and phosphonic acid dimethyl ester solution being not more than 100% by weight, based on the weight of alkali metal hydroxide and phosphonic acid dimethyl ester, at 90.degree. to 130.degree. C. and distilling off the methanol formed.Type: GrantFiled: January 24, 1996Date of Patent: January 6, 1998Assignee: Hoechst AktiengesellschaftInventor: Hans-Jerg Kleiner
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Patent number: 5543542Abstract: .alpha.-Phosphonosulfinate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula ##STR1## wherein R.sup.2 is OR.sup.5 or R.sup.5a ; R.sup.3 and R.sup.5 are independently H, alkyl, arylalkyl, aryl or cycloalkyl; R.sup.5a is alkyl, arylalkyl or aryl; R.sup.4 is H or a pharmaceutically acceptable cation; Z is H, halogen, lower alkyl or lower alkenyl; and R.sup.1 is a lipophilic group which contains at least 7 carbons and is alkyl, alkenyl, alkynyl, mixed alkenyl-alkynyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroarylalkyl, cycloheteroalkyl, cycloheteroalkylalkyl; including pharmaceutically acceptable salts.Type: GrantFiled: May 22, 1995Date of Patent: August 6, 1996Inventors: R. Michael Lawrence, Scott A. Biller, Olga M. Fryszman
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Patent number: 5430169Abstract: The present invention provides a series of non-toxic compounds which function to inhibit the activity of S-1-P aldolase in respect to its cleavage of S-1-P. These inhibitors are described by the compounds of formula I ##STR1## wherein R is a radical containing 1 to 15 carbon atoms, a halogen, or hydrocarbon, R' is an organic radical or hydrogen, and R" is --NH.sub.3.sup.+ or --NH--NH .sup.+, with the proviso that, when R is CH.sub.3 (CH).sub.12 (CH.dbd.CH) and R' is hydrogen, R" is --NH--NH.sub.3.sup.+.A method for preparing such compounds, which may generally be described as 1-phosphate derivatives of compounds which include a 2-amino-1,3-alcohol radical is also disclosed.Type: GrantFiled: February 14, 1994Date of Patent: July 4, 1995Assignee: The United States of America represented by the Department of Health and Human ServicesInventors: Ahcene Boumendjel, Stephen P. F. Miller
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Patent number: 5321153Abstract: This invention is selected novel chiral (essentially pure) alpha-amino phosphonates, process for the preparation which is a catalytic asymmetric hydrogenation of olefins and novel intermediates therefor. The alpha-amino phosphonates are useful as antibiotics and/or as intermediates in the preparation of phosphorus-containing analogs of peptides, i.e., phosphonopeptides or pseudopeptides having known uses, such as in antibiotics, antibiotic enhancers, or enzyme inhibitors.Type: GrantFiled: June 15, 1992Date of Patent: June 14, 1994Assignee: Monsanto CompanyInventor: John J. Talley
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Patent number: 5312953Abstract: Polyether bis-phosphonic acid compounds are disclosed which have the formula (HO).sub.2 OP--R--(OR').sub.n --OR--PO(OH).sub.2 where R is selected from the group consisting of methylene and ethylene, R' is selected from the group consisting of ethylene and ethylene substituted with one or more methyl groups, and n is an integer from 1 to 4, water soluble salts thereof, and esters thereof with alkyl groups having from 1 to 6 carbon atoms. Also disclosed is a novel preparation of these compounds by reacting hydroxyalkylphosphonic acid dialkyl ester compounds with 2-benzyloxyalkyl organic sulfonates; reacting the intermediate formed therefrom with hydrogen or a hydrogen source; reacting the intermediate formed therefrom with a hydrogen ion acceptor and certain sulfonyl chlorides; and reacting the intermediate formed therefrom with hydroxyalkylphosphonic acid dialkyl ester compounds to form a polyether bis-phosphonic acid compound which may be hydrolyzed to form the polyether bis-phosphonic acid.Type: GrantFiled: August 17, 1993Date of Patent: May 17, 1994Assignee: W. R. Grace & Co.-Conn.Inventors: Charles G. Carter, Ranjit Kumar
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Patent number: 5091549Abstract: A method of synthesizing D-myoinositol-1-phosphate from 1,2-(R.sup.1)-3-R.sup.2 -myoinositol compounds of the formula ##STR1## wherein R.sup.1 is a bridging type protective group bonded to two oxygen atoms at the 1- and 2-position, and R.sup.2 is a protective group coupled to the oxygen atom at the 3-position. D-Myoinositol-1-phosphate is useful as an intermediate for the production of inositol-1,4,5-triphosphate.Type: GrantFiled: August 31, 1990Date of Patent: February 25, 1992Assignee: The Yokohama Rubber Company, Ltd.Inventors: Shoichiro Ozaki, Takahiko Akiyama, Naoto Takechi, Kunio Kageyama, Morihisa Machida
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Patent number: 5004825Abstract: A di(fluoroalkyl containing group-substituted alkyl) phosphate salt which is useful for a surface active agent, a water- and/or oil-repellent for fiber or paper or an oil resistant agent, can be prepared a process which comprises hydrolyzing a mono-sec.- or tert.-alkyl (di(fluoroalkyl containing group-substituted alkyl) phosphate with a base.Type: GrantFiled: July 18, 1989Date of Patent: April 2, 1991Assignee: Daikin Industries Ltd.Inventors: Tutomu Yoshida, Shigeharu Iida
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Patent number: 4997968Abstract: A method of preparing an oil-soluble composition is disclosed. The method comprises preparing a dihydrocarbyl monothiophosphoric acid characterized by the formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently hydrocarbyl groups of from 1 to about 30 carbon atoms and X is oxygen or sulfur, with the proviso that one X is sulfur comprising reacting(A) a phosphite ester of the structure ##STR2## with (B) a sulfur source, in the presence of(C) a catalytic amount of an amide of the structure R.sub.3 CONR.sub.4 R.sub.5 wherein R.sub.3, R.sub.4 and R.sub.5 are each independently hydrogen or a hydrocarbyl group containing from 1 to about 30 carbon atoms or an ethoxylated amide of the structure ##STR3## wherein the sum of x and y is from 1 to about 50; and isolating the reaction product obtained.Type: GrantFiled: September 28, 1989Date of Patent: March 5, 1991Assignee: The Lubrizol CorporationInventors: Louis Burjes, Alan C. Clark
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Patent number: 4950819Abstract: A process for the preparation of alkali metal salts of phosphonic acid monoalkyl esters of formula ##STR1## by reacting 1 mole of a phosphonic acid ester of formula ##STR2## with 1 mole of a finely particulate alkali metal halide of formula XY. In these formulae, R is straight chain or branched C.sub.1 -C.sub.20 alkyl, R.sub.1 is C.sub.1 -C.sub.4 alkyl, X is an alkali metal cation and Y is a halogen anion.Type: GrantFiled: September 19, 1988Date of Patent: August 21, 1990Assignee: Ciba-Geigy CorporationInventors: Claus D. Weis, Peter Sutter
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Patent number: 4939285Abstract: Metal salts of phosphoric and phosphonic acid esters of formula ##STR1## wherein R is C.sub.1 -C.sub.4 alkoxy or straight chain or branched unsubstituted C.sub.1 -C.sub.20 alkyl or C.sub.2 -C.sub.6 alkenyl,R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl,X is a metal cation, andn is an integer from 1 to 3 corresponding to the valence of X,are prepared by reacting n moles of a phosphoric or phosphonic acid or an ester thereof, of formula ##STR2## wherein R, R.sub.1 and n are as defined above, with 1 mole of a metal X.sup.n, if desired with cooling. These salts can be used, for example, as flame retardants, fertilizers or emulsifiers for aqueous plastics dispersions.Type: GrantFiled: July 6, 1988Date of Patent: July 3, 1990Assignee: Ciba-Geigy CorporationInventors: Claus D. Weis, Peter Sutter
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Patent number: 4874882Abstract: Disclosed are a process for preparing monosodium phosphoenolpyruvate, which comprises subjecting monosodium monosubstituted phosphoenolpyruvate of Formula (I): ##STR1## wherein, R represents an alkyl group, a cycloalkyl group or an aralkyl group,to hydrolysis, and a use of monosodium phosphoenolpyruvate as a visceral function improver.This invention provides a simple production process of monosodium phosphoenolpyruvate which is practicable on an industrial acale.Type: GrantFiled: March 18, 1987Date of Patent: October 17, 1989Assignee: Ube Industries, Ltd.Inventors: Naotaka Hamasaki, Hirotaka Kawamura, Norio Ohtsu, Ichiro Nakakoshi, Kikuo Ataka, Kiyosi Oomori, Masahiko Kouno
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Patent number: 4812502Abstract: An oligomer flame-retarding additive can be defined by the general formula ##STR1## wherein: R is the hydrogen atom, or a linear or branched alkyl radical, containing from 1 to 6 carbon atoms;m takes the value 1, 2 or 3;n takes a value, or an average value, comprised within the range of from 2 to 50.Such an additive is obtained by means of the oligomerization of a hydroxyalkylenephenylphosphinic acid or of a related alkyl ester thereof.According to another form of practical embodiment, the flame-retarding additive is the product of co-oligomerization of a hydroxyalkylenephenylphosphinic acid, or of a related alkyl ester thereof, with a phenylphosphonic acid or a related alkyl ester thereof.Such oligomer additives are used for endowing a linear polyester with self-extinguishing characteristics.Type: GrantFiled: July 7, 1987Date of Patent: March 14, 1989Assignee: Enichem Sintesi, S.p.A.Inventors: Gioacchino Cipriani, Armando Mariano
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Patent number: 4675429Abstract: Herbicidal compounds of formula: ##STR1## in which R.sup.1 denotes an optionally halogenated alkyl radical containing from 1 to 4 carbon atoms,R denotes the hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms,R.sup.2 denotes the hydrogen atom or R21,R.sup.21 and R.sup.3 denote optionally substituted aryl radicals,R.sup.4 denotes a hydrogen atom or a hydrogenolysable group R.sup.8,and the agriculturally acceptable salts of these compounds.Type: GrantFiled: January 14, 1986Date of Patent: June 23, 1987Assignee: Rhone-Poulenc AgrochimieInventors: Guy Borrod, Guy Lacroix
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Patent number: 4666967Abstract: The invention provides polyurethanes and polyisocyanurate having incorporated therein a flame retardant amount of a salt formed by reaction between dimethyl methyl phosphonate, monomethyl methyl phosphonate or methyl phosphonic acid, and a compound of the general formula (I). ##STR1## in which X is O, S or NH, R.sup.1 is H, alkyl with 1 to 4 carbon atoms, alkenyl of up to 4 carbon atoms, CN, CONH.sub.2 or NH.sub.2, R.sup.2 is H, alkyl with 1 to 4 carbon atoms or alkenyl of up to 4 carbon atoms or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached form a heterocyclic ring of up to 6 carbon atoms which may optionally contain another hetero atom and R is H, an alkyl group with 1 to 8 carbon atoms, an aryl group with 6 to 10 carbon atoms, a cycloalkyl group with 5 to 12 carbon atoms or a heterocyclic group with up to 9 ring carbon atoms, or, together with R.sup.1 forms an alkylene chain of 3 to 10 carbon atoms, or R is a group NHR.sup.3 wherein R.sup.Type: GrantFiled: January 22, 1986Date of Patent: May 19, 1987Assignee: Ciba-Geigy CorporationInventors: Norman Richardson, deceased, Brian G. Clubley, Richard J. Dellar
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Patent number: 4602087Abstract: The distyrylbiphenyls of the formula ##STR1## in which X and X' independently of one another are a direct bond, oxygen, sulfur, --O--C.sub.1-3 -alkylene-CON(R.sub.4)--CON(R.sub.4)--, --O--C.sub.1-3 alkylene-COO--, OCO or --COO--, with the proviso that if n+n'=O, X and X' may not be --CON(R.sub.4)-- or O--C.sub.1-3 -alkylene-CON(R.sub.4)--, and if n+n'=2 and X and X' are --CON(R.sub.4)-- or --COO--, A.sup..crclbar. may not be a phosphite or phosphonate anion, and Y and Y' independently of one another are C.sub.1-20 -alkyene, R.sub.1 and R.sub.1 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, R.sub.1 together with R.sub.2, or R.sub.1 ' together with R.sub.2 ', is a heterocyclic ring, R.sub.2 and R.sub.2 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, or R.sub.2 together with R.sub.1, or R.sub.2 ' together with R.sub.1 ', is a heterocyclic ring, or R.sub.1 and R.sub.2, or R.sub.1 ' and R.sub.Type: GrantFiled: May 18, 1984Date of Patent: July 22, 1986Assignee: Ciba-Geigy CorporationInventors: Christian Luthi, Hans R. Meyer, Kurt Weber