Abstract: The compounds of the formula (I)H.sub.3 C--P(.dbd.O)(OR)--CH.sub.2 CH.sub.2 COOR (I)in which R is (C.sub.4 -C.sub.8)alkyl are suitable as intermediates for the preparation of herbicides.They can be prepared according to the invention, in which compounds of the formula (II)CH.sub.3 P(.dbd.O) (Cl)--CH.sub.2 CH.sub.2 COCl (II)are reacted with an alcohol of the formula ROH or a corresponding alcohol mixture at -30.degree. to +50.degree. C.
Abstract: Compounds of formula ##STR1## (wherein R, R.sub.1, R.sub.2, R.sub.3, n, m and p have the meanings reported in the specification), their preparation and the compositions for pharmaceutical use containing them as active ingredient are described.The compounds of formula I have dopaminergic vasodilator activity and they may be used in pharmaceutical field.
Type:
Grant
Filed:
July 31, 1991
Date of Patent:
September 29, 1992
Assignee:
SIMES Societa Italiana Medicinali e Sintetici S.p.A.
Inventors:
Cesare Casagrande, Gabriele Norcini, Francesco Santangelo, Claudio Semeraro
Abstract: Phosphoric acid esters and their salts corresponding to the formula (I): ##STR1## wherein R represents an aliphatic, cycloaliphatic and/or aromatic moiety having no Zerewitinoff hydrogen, containing at least one ether oxygen atom (--O--) and at least one carboxylic acid ester group (--COO--) and/or urethane group (--NHCOO--), and having an average molecular weight M.sub.n of 200 to 10,000, wherein the hydrogen atoms may be partially replaced by halogen atoms, and wherein the ratio of the number of ether oxygen atoms to the number of the carboxylic acid ester groups and/or urethane groups in the molecule (or in every group R) is in the range from 1:20 to 20:1, and n represents 1 or 2. A method for preparing such phosphoric acid esters and salts and the use of such phosphoric acid esters or salts as dispersants or dispersing aids is also disclosed.
Type:
Grant
Filed:
August 6, 1990
Date of Patent:
July 14, 1992
Assignee:
BYK-Chemie, GmbH
Inventors:
Karl-Heinz Haubennestel, Wolfgang Pritschins
Abstract: The invention relates to the new compound (2R)-2-[di(2-propyl)phosphonylmethoxy]-3-p-toluenesulfonyloxy-1-trimethyla cetoxypropane and the method of producing it. The compound may be used for producing (S)-N-(3-hydroxy-2-phosphonylmethoxypropyl) derivatives of the heterocyclic purine and pyrimidine bases of antiviral activity.
Type:
Grant
Filed:
July 12, 1991
Date of Patent:
July 14, 1992
Assignee:
Ceskoslovenska akademie ved
Inventors:
Petr Alexander, Antonin Holy, Hana Dvorakova
Abstract: Compounds of the formula Ia or Ib ##STR1## in which R.sub.1 and R.sub.2, independently of one another, are hydrogen, alkyl, cycloalkyl, alkenyl, aryl or aralkyl or, together with the carbon atoms in the .alpha.-position to the carbonyl groups, form a cyclopentane, cyclopentene, cyclohexane, cyclohexene, cyclohexadiene or bicyclo[2.2.1]hept-5-ene ring which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, or form a monocyclic or polycyclic, aromatic ring system which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, R.sub.3 and R.sub.4, independently of one another, are hydrogen, alkyl, alkenyl, aryl or aralkyl, and R.sub.5 and R.sub.6, independently of one another, are alkyl, aryl or aralkyl groups, are highly suitable as flame retardants for polymers.
Abstract: It has now been discovered that oligomers of C.sub.6 - C.sub.20 alpha-olefins, such as 1-decene, with branch ratios below 0.19 and high viscosity indices (HVI) can be functionalized to provide unique phosphite derivatives. Functionalized polyalpha-olefin lubricants compositions are prepared with superior properties by adding functionalized organophosphites to the olefinic bond of HVI-PAO. The invention encompasses a process for the preparation of lubricant range hydrocarbons containing phosphonate functional groups, comprising;reacting olefinic C.sub.20 + polyalpha-olefin oligomers having a branch ratio of less than 0.19 and phosphite ester in a mixture with peroxide catalyst at elevated temperature whereby phosphite ester adduct of said polyalpha-olefin is formed;separating said reaction mixture products and recovering said adduct.
Type:
Grant
Filed:
June 24, 1988
Date of Patent:
April 14, 1992
Assignee:
Mobil Oil Corporation
Inventors:
Linda A. Benjamin, Derek A. Law, Andrew G. Horodysky
Abstract: Compounds which are useful as inhibitors of cholesterol biosynthesis and thus as hypocholesteroleumic agents are provided which have the structure ##STR1## wherein R is OH, or salts thereof or lower alkoxy; R.sup.x is H or alkyl;X is --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --CH.sub.2 CH.sub.2 CH.sub.2 -- or --CH.sub.2 O-- (where O is linked to Z);Z is a hydrophobic anchor, such as ##STR2## wherein the dotted lines represent optional double bonds. New intermediates used in preparing the above compounds, pharmaceutical compositions containing such compounds and a method for using such compounds to inhibit cholesterol biosynthesis are also provided.
Type:
Grant
Filed:
April 18, 1988
Date of Patent:
February 25, 1992
Assignee:
E. R. Squibb & Sons, Inc.
Inventors:
Donald S. Karanewsky, Michael C. Badia, Scott A. Biller, Eric M. Gordon, Michael J. Sofia
Abstract: Novel phosphite derivatives of propylene based lube olefins are novel lubricating fluid media with internal synergistic multifunctional extreme pressure, antiwear and antioxidant properties. These compounds exhibit the same multifunctional characteristics when used in minor additive amounts in either mineral or synthetic lubricating oils as well as fuels.
Type:
Grant
Filed:
December 30, 1988
Date of Patent:
December 10, 1991
Assignee:
Mobil Oil Corporation
Inventors:
Linda A. Benjamin, Andrew G. Horodysky, Derek A. Law, Nancy M. Page
Abstract: Methods for converting phosphonates into thiophosphonates and specific thiophosphonate compounds so produced are disclosed and claimed. The methods start with a reaction mixture formed of a phosphonate compound, including one or more strong electron-withdrawing groups located adjacent to the phosphorus in the compound, a slight excess of Lawesson's reagent, and a polar aprotic solvent. The reaction mixture is heated until reaction is complete and may be followed with separation or hydrolyzation steps to produce thiophosphonic acids and their addition salts. One of these thio-analogues, thiophosphonoformic acid (TPFA) is particularly effective at inhibiting HIV replication and in treating mammals infected with HIV.
Abstract: Novel diacylglycerophosphoric acid esters include a hydrophobic diacyl glycerol portion to provide water insolubility and a head group which forms a chromophore or a chromophore precursor when the head group is enzymatically released and are chromogenic substrates useful to assay for enzymes catalyzing the cleavage of phosphate ester or phosphoanhydride bonds adjacent or opposite to the phosphatidic acid region of a phospholipid molecule.
Type:
Grant
Filed:
April 6, 1990
Date of Patent:
April 30, 1991
Assignee:
Cornell Research Foundation, Inc.
Inventors:
Dennis C. Mynarcik, Owen W. Griffith, Gordon F. Fairclough, Jr.
Abstract: A novel phosphoric ester of the formula (I) ##STR1## wherein, Z represents the following radicals ##STR2## useful as modifiers for amino acids, peptides and proteins which are easily decomposable in living bodies.
Type:
Grant
Filed:
December 19, 1989
Date of Patent:
February 19, 1991
Assignee:
Kao Corporation
Inventors:
Motoru Takeda, Mitsuharu Masuda, Takashi Imamura, Tomihiro Kurosaki
Abstract: Antihypertensive phosphate derivatives having the following formula are described: ##STR1## wherein X is selected from one or more of: (a) C.sub.1 -C.sub.24 branched or straight chain alkyl; (b) C.sub.1 -C.sub.24 branched or straight chain alkoxy; (c) ##STR2## wherein n and m are integers from 0 to 25 and the sum of n and m is less than or equal to 25; phenyl; substituted phenyl wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, C.sub.1 -C.sub.20 branched or straight chain alkoxy, halogen, trifluoromethyl, phenyl, and substituted phenyl, phenoxy; and substituted phenoxy, wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, halogen, trifluoromethyl, phenyl and substituted phenyl; Q is selected from the group consisting of: ##STR3## wherein R.sub.1 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 branched or straight chain alkyl, C.sub.1 -C.sub.
Type:
Grant
Filed:
November 8, 1989
Date of Patent:
January 1, 1991
Assignee:
American Cyanamid Company
Inventors:
Allan Wissner, Phaik E. Sum, Robert E. Schaub
Abstract: Process for the introduction of functional or functionalizable substituents para to the amino group in 2-aminophenols and 3-aminophenols. The process proceeds in one step, with substitution occurring selectively at the position para to the amino group. Consequently, the reaction is surprisingly straightforward, with very little or no contamination by isomeric by-products. The process comprises reaction of (a) an aminophenol having an open para position to the amino function, with (b) an unhindered non-enolizble aldehyde, and (c) a thiol or sulfinic acid which acts as a nucleophile. In preferred embodiments, the process is conducted at a temperature of from about 50.degree. C. to about 100.degree. C., and in the presence of a polar solvent. The reaction is promoted by an acid having sufficient acidity to protonate the amino group of the aminophenol. Preferably, the acid promoter is a mineral acid, and it is present in an amount at least substantially equivalent to the amount of aminophenol reactant.
Abstract: Compounds which are useful as inhibitors of cholesterol biosynthesis and thus as hypocholesterolemic agents are provided which have the structure ##STR1## including salts thereof, wherein R is OH, lower alkoxy or lower alkyl; R.sup.x is H or alkyl;X is --O-- or --NH--;n is 1 or 2Z is a hydrophobic anchor, such as ##STR2## wherein the dotted lines represent optional double bonds. New intermediates used in preparing the above compounds, pharmaceutical compositions containing such compounds and a method for using such compounds to inhibit cholesterol biosynthesis are also provided.
Type:
Grant
Filed:
April 18, 1988
Date of Patent:
February 27, 1990
Assignee:
E. R. Squibb & Sons, Inc.
Inventors:
Donald S. Karanewsky, Scott A. Biller, Eric M. Gordon
Abstract: 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.
Abstract: A method is provided for preparing phosphinic acid compounds, which are useful in preparing certain angiotensin converting enzyme inhibitors, which have the formula ##STR1## wherein R.sub.1 is lower alkyl, aryl, arylalkyl, cycloalkyl or cycloalkylalkyl;R.sub.2 is hydrogen, lower alkyl or arylalkyl;X is hydrogen, lower alkyl or phenyl;Y is hydrogen, lower alkyl, phenyl or alkoxy, or together X and Y are --(CH.sub.2).sub.2 --, --(CH.sub.2).sub.3 --, --CH.dbd.CH--, or ##STR2## and n is 0 or 1including salts thereof and stereoisomers thereof, which method includes the steps of reacting a phosphinic acid ester of the structure ##STR3## wherein R.sub.
Type:
Grant
Filed:
September 30, 1987
Date of Patent:
October 10, 1989
Assignee:
E. R. Squibb & Sons, Inc.
Inventors:
Edward W. Petrillo, Jr., Donald S. Karanewsky, John K. Thottathil, James E. Heikes, John A. Grosso
Abstract: Herbicidally active novel phenoxybenzoic acid derivatives of the formula ##STR1## in which R represents hydrogen, nitro or cyano,R.sup.1 represents hydrogen or alkyl andR.sup.2 and R.sup.3 are identical or different and represent hydrogen, alkyl, halogenalkyl or one equivalent of an alkali metal or alkaline earth metal ion, orR.sup.2 and R.sup.3 together represent an optionally substituted alkanediyl radical.
Type:
Grant
Filed:
October 30, 1986
Date of Patent:
February 9, 1988
Assignee:
Bayer Aktiengesellschaft
Inventors:
Heinz Forster, Hans-Joachim Santel, Robert R. Schmidt
Abstract: A metal salt of an organic phosphate, having good stability and cholesterol-lowering activity, is produced by reacting a known compound ##STR1## wherein R.sub.4 and R.sub.5 are hydrogen or methyl, with a reaction agent such as metal hydroxide.
Abstract: Compounds of the formula ##STR1## are useful in the preparation of .alpha.-acyloxy phosphonate compounds. The final products are useful as anti-hypertensive agents due to their angiotensin converting enzyme inhibition activity.
Abstract: Novel phosphonic acid and phosphinic acid derivatives of the formula I ##STR1## wherein X is hydrogen or chlorine,n is 0 or 1,R.sup.1 and R.sup.2 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 cyanoalkyl, or they are a phenyl radical, a phenyl-C.sub.1 -C.sub.4 alkyl radical or a naphthyl radical, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano, andA is a C.sub.1 -C.sub.3 alkyl chain which may be substituted by one or two C.sub.1 -C.sub.2 alkyl radicals and/or by one or two phenyl radicals, with the proviso that R.sup.2 is not hydrogen if n is 0, have a good selective herbicidal activity. They are suitable for controlling monocot and dicot weeds pre- and postemergence in various crops of useful plants, e.g.
Abstract: Disclosed is a process for the preparation of .alpha.-haloacetoacetic esters by the reaction of an alkali metal alkoxide with a 5-halo-4H-1,3-dioxin-4-one compound, the desired product being obtained as an alkali metal salt which may be converted to the corresponding free ester by treating with acid.
Abstract: Diphenyl ether derivatives of the formula ##STR1## and tautomers thereof wherein X is selected from the group consisting of chlorine, bromine, iodine, fluorine, methyl, cyano or hydrogen; Y is CF.sub.n H.sub.3-n or chlorine, wherein n is an integer from 0 to 3; R is selected from the group consisting of nitro, hydrogen or halogen; R" is hydrogen, alkyl, phenyl, or substituted alkyl wherein the alkyl group has from 1 to 10 carbon atoms; R"' is the same or different and is selected from C.sub.1 -C.sub.10 alkyl, phenyl or hydrogen; and agriculturally acceptable salts thereof. The compounds are effective as herbicides.
Abstract: Phosphonyl hydroxyacyl amino acids of the formula ##STR1## wherein X is a substituted or unsubstituted imino or amino acid or ester. These compounds possess angiotensin converting enzyme activity and are thus useful as hypotensive agents.
Type:
Grant
Filed:
December 16, 1985
Date of Patent:
October 7, 1986
Assignee:
E. R. Squibb & Sons, Inc.
Inventors:
Donald S. Karanewsky, Edward W. Petrillo, Jr.
Abstract: Dialkyl vinylphosphonates are prepared by heating the new dialkyl 2-alkylcarbonatoethanephosphonates in the presence of catalysts. Also disclosed is a process for making the new dialkyl 2-alkylcarbonatoethanephosphonate by transesterification of a dialkyl 2-carboxyethanephosphonate with a dialkyl carbonate in the presence of a transesterification catalyst.
Abstract: Disclosed are novel 5-halo-4H-1,3-dioxin-4-ones and their preparation by treating a compound having the formula ##STR1## with X.sub.2 or SO.sub.2 X.sub.2 wherein X is Cl or Br.