Halogen Or Unsaturation In Acid Moiety Patents (Class 560/172)
  • Patent number: 6452038
    Abstract: The present invention provides a compound according to the formula: CH2═C(R1)—C(O)—R6—NHCO2(CH2)p(CF2)q—O—((CF2)aCFXO)m(CF2)r—Z wherein each R1 is independently selected from —H, —CH3, —F and —Cl, wherein each R6 is independently selected from substituted or unsubstituted C1-C10 alkyl, cyclic alkyl, or aryl groups, wherein each a is independently selected from 0-3, wherein each X is independently selected from —F, —CF3 or —CF2CF3, wherein each p is independently selected from 1-4, each q is independently selected from 1-5, each r is independently selected from 1-5, each m is independently selected from 1-50, each Z is independently selected from —F and —(CH2)sOH, and each s is independently selected from 1-4. The present invention also provides for the use of this compound as a surfactant in highly fluorinated liquid solvents. Latexes of dispersed particles utilizing this surfactant are provided.
    Type: Grant
    Filed: June 28, 2000
    Date of Patent: September 17, 2002
    Assignee: 3M Innovative Properties Company
    Inventors: Prabhakara Satyauolu Rao, Naiyong Jing
  • Patent number: 6451854
    Abstract: The present invention relates to &agr;-amino acid phenyl ester derivatives having general formula (I) wherein R1 is (C1-3)alkyloxy; R2 is (C1-3)alkyl, (C1-3)alkyloxy or (C2-3)alkenyl; R3 is hydrogen, (C1-3)alkyl, (C1-3)alkyloxy or (C2-3)alkenyl; R4 is (C1-6)alkyl; R5 and R6 are independently (C1-6)alkyl, (C2-6)alkenyl, (C2-6)alkynyl or aralkyl, each of which may be optionally substituted with (C1-3)alkyloxy, (C1-3)alkyloxycarbonyl, cyano or NR7R8; R7 and R8 are independently (C1-6)alkyl; or a pharmaceutically acceptable salt thereof. The invention also relates to pharmaceutical compositions comprising said derivatives, and to the use of these &agr;-amino acid phenyl ester derivatives as hypnotics for the induction and maintenance of general anaesthesia.
    Type: Grant
    Filed: January 18, 2001
    Date of Patent: September 17, 2002
    Assignee: Akzo Nobel N.V.
    Inventor: Niall Morton Hamilton
  • Patent number: 6423866
    Abstract: Lower alkyl esters of 3-amino crotonates substituted by halogen in the C-4 position, e.g. ethyl 3-amino-4,4,4-trifluoro-crotonate, in which the amino group optionally may be substituted by one or two C1 to C3 alkyl groups or by one or two aryl groups, e.g. phenyl, are synthesized by thermolysis of ammonium salts of corresponding lower alkyl esters of acetoacetic acid substituted in the C-4 position by halogen, and removal of the resulting water of reaction. The water of reaction may be removed by an entraining agent, which preferably has a specific gravity heavier than that of the aqueous phase which forms in the reaction. This minimizes yield losses due to the ammonium salt becoming dissolved in the aqueous phase and results in especially high yields. Formation of the ammonium salt and thermolysis can be carried out simultaneously. Alternatively, it is possible to start from a molten ammonium salt of the halogencrotonate, e.g.
    Type: Grant
    Filed: May 8, 2000
    Date of Patent: July 23, 2002
    Assignee: SolvaytFlour und Derivate GmbH
    Inventors: Max Braun, Francine Jannssens, Werner Rudolph, Kerstin Eichholz
  • Patent number: 6355713
    Abstract: &bgr;-Ketoesters and their enamines derived from alcohols or polyols are suitable for stabilizing polymers, and are represented by formulae: A[(O—CHR4—Z—CHR5)m—O—CO—CHR1—CO—R3]n and A[(O—CHR4—Z—CHR5)m—O—CO—CR1═C(—NHR2)—R3]n, wherein: A is the residue of an alcohol or polyol selected from hydroxyalkanoic acid esters, sugars and their glycosides, sugar alcohols, sugar acids and their esters, and oligosaccharides; m is an integer number from 0 up to 6; n is a number from 1 up to the total number of hydroxyl groups in the polyol; R1 is hydrogen, C1-C8 alkyl, C3-C8 alkenyl or cycloalkyl (alkyl) or C6-C8 aryl or aralkyl; R2 is hydrogen, C1-C6 alkyl, C2-C6 hydroxyalkyl or C3-C6 alkenyl; R3 is C1-C18 alkyl, alkoxy or alkylamino, C3-C18 alkenyl, alkanoylmethyl, alkoxycarbonylmethyl or cycloalkyl(alkyl), C6-C18 aryl, aryloxy, arylamino, aralkyl, aralkoxy or aralkylamino, or C8-C18 aroylmethyl, arylox
    Type: Grant
    Filed: January 7, 2000
    Date of Patent: March 12, 2002
    Assignee: Akcros, Chemicals
    Inventors: Hendrikus Luitjes, Jacco Van Haveren, Augustinus Emmanuel Frissen, Gerard Hubert Schmets, Frans Jeanette Maria Leonardus Peters, Erica Gertruda Arnolda Kroon, Johannes Albertus Van Der Waal
  • Patent number: 6307103
    Abstract: An improved process for the preparation of a 1,1,1-trifluoro-2-aminoalkane of formula I wherein R1 represents an optionally substituted alkyl group; which comprises hydrogenating the corresponding oxime of formula II wherein R1 has the meaning given above and the winding line indicates that the hydroxy group may be in the (E)- or (Z)-position with respect to the trifluoromethyl group, in the presence of Raney nickel and a diluent; the improvement wherein is, that said reaction is carried out in a diluent selected from an alkanol, a cyclic ether and an aromatic hydrocarbon.
    Type: Grant
    Filed: March 28, 2000
    Date of Patent: October 23, 2001
    Assignee: American Cyanamid Company
    Inventors: Hans-Peter Niedermann, Dieter Gutheil
  • Patent number: 6166259
    Abstract: The invention relates to a process for the preparation of a 1,1,1-trifluoro-2-aminoalkane of formula I ##STR1## wherein R.sup.1 represents an optionally substituted alkyl group; which comprises heating a mixture consisting essentially of a compound of formula II ##STR2## wherein R.sup.1 has the meaning given, and R.sup.2 represents an optionally substituted aryl group, a primary amine, and optionally a base and/or an inert diluent, whereby the compound of formula I is removed by distillation during the heating procedure.
    Type: Grant
    Filed: March 28, 2000
    Date of Patent: December 26, 2000
    Assignee: American Cyanamid Company
    Inventors: Rudi Eisenacht, Hans-Peter Niedermann, Dieter Landau
  • Patent number: 5952458
    Abstract: Synthesis of a vinyl terminated polymer by reacting a cationically polymerizable monomer in the form of a cyclic ether with an acid chloride in a suitable solvent and in the presence of a Lewis acid. The vinyl-terminated polymers can be polymerized with other appropriate monomers resulting in thermoplastic elastomers having suitable properties for use as binders for explosives and propellants.
    Type: Grant
    Filed: September 24, 1998
    Date of Patent: September 14, 1999
    Assignee: The Government of the United States as represented by the Secretary of the Navy
    Inventor: Mostafa A. H. Talukder
  • Patent number: 5952316
    Abstract: 2-Amino-1,3-propanediol compounds of the formula (I) ##STR1## wherein R is an optionally substituted straight- or branched carbon chain, an optionally substituted aryl, an optionally substituted cycloalkyl or the like, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different and each is a hydrogen, an alkyl, an aralkyl, an acyl or an alkoxycarbonyl, pharmaceutically acceptable salts thereof and immunosuppressants comprising these compounds as active ingredients.The 2-amino-1,3-propanediol compounds of the present invention show immunosuppressive action and are useful for suppressing rejection in organ or bone marrow tranplantation, prevention and treatment of autoimmune diseases or as reagents for use in medicinal and pharmaceutical fields.
    Type: Grant
    Filed: August 14, 1997
    Date of Patent: September 14, 1999
    Assignees: Yoshitomi Pharmaceutical Industries, Ltd., Taito Co., Ltd.
    Inventors: Tetsuro Fujita, Shigeo Sasaki, Masahiko Yoneta, Tadashi Mishina, Kunitomo Adachi, Kenji Chiba
  • Patent number: 5945558
    Abstract: A method is disclosed for making dibasic amino acid monoesters useful in repair of teeth in which a dibasic amino acid is partially esterified with an allylic acrylic compound in the presence of an acidic ion-exchange resin at ambient temperature. The invention also comprises cyclicizing the amino groups of the monoesters.
    Type: Grant
    Filed: July 1, 1997
    Date of Patent: August 31, 1999
    Assignee: Southwest Research Institute
    Inventor: William A. Mallow
  • Patent number: 5910602
    Abstract: The present invention relates to methods for preparing 3-amino-4,4,4-trihalocrotonates and their derivatives from a 4,4,4-trihaloacetoacetate derivative and an amine or ammonium salt.
    Type: Grant
    Filed: April 29, 1998
    Date of Patent: June 8, 1999
    Assignee: Rohm and Haas Company
    Inventors: Joshua Anthony Chong, Fereydon Abdesken, Peter Osei-Gyimah
  • Patent number: 5902887
    Abstract: Compounds formed by reacting a protected amino acid with an alkali metal enolate of an alkyl acetate are reacted with a halogenating agent for halogenation of the 2-position, or a protected amino acid is reacted with an alkali metal enolate of an alkyl halogenoacetate, to form a 4-amino-3-oxo-2-halogenobutanoic acid ester derivative, and hydrolysis and decarboxylation are conducted to produce a 3-amino-2-oxo-1-halogenopropane derivative or its salt. The present method is a useful process for producing a 3-amino-2-oxo-1-halogenopropane derivatives which can easily be converted to a 3-amino-1,2-epoxypropane.
    Type: Grant
    Filed: April 14, 1998
    Date of Patent: May 11, 1999
    Assignee: Ajinomoto Co., Inc.
    Inventors: Yutaka Honda, Satoshi Katayama, Kunisuke Izawa, Masakazu Nakazawa, Takayuki Suzuki, Naoko Kanno
  • Patent number: 5840961
    Abstract: The invention herein is directed to a process for the preparation of ethyl 3S-amino-4-pentynoate which involves treating 3-(trimethylsilyl)-2-propynal with L-phenylglycinol in toluene to produce .alpha.S-??3-(trimethylsilyl)-2-propynylidene amino!benzenethanol; reacting .alpha.S-??3-(trimethylsilyl)-2-propynylidene!amino!benzenethanol with BrZnCH.sub.2 CO.sub.2 t-Bu in THF/NMP to produce 1,1-dimethylethyl 3S-?(2-hydroxy-1S-phenylethyl)amino!-5-(trimethylsilyl)-4-pentynoate; reacting the 1,1-dimethylethyl 3S-?(2-hydroxy-1S-phenylethyl)amino!-5-(trimethylsilyl)-4-pentynoate with sodium periodate to form 1,1-dimethylethyl 3S-?(phenylmethylene)amino!-5-(trimethylsilyl)-4-pentynoate; hydrolyzing 1,1-dimethylethyl 3S-?(phenylmethylene)amino!-5-(trimethylsilyl)-4-pentynoate to produce 1,1-dimethylethyl 3S-amino-5-(trimethylsilyl)-4-pentynoate; transesterifying 1,1-dimethyl 3S-amino-5-(trimethylsilyl)-4-pentynoate and desilylating to produce ethyl 3S-amino-4-pentynoate.
    Type: Grant
    Filed: July 10, 1997
    Date of Patent: November 24, 1998
    Assignee: G. D. Searle & Co.
    Inventors: James Richard Behling, Mark Laurence Boys, Kimberly Jo Cain-Janicki, Pierre-Jean Colson, Wendel William Doubleday, Joseph Edward Duran, Payman N. Farid, Carl Matthew Knable, Frank Walter Muellner, Sean Thomas Nugent, Ravindra S. Topgi
  • Patent number: 5777184
    Abstract: A process for producing a fluorinated olefin having the formula:CH.sub.3-a F.sub.a CH.dbd.CHClwhere a=1,2 or 3, said process comprising catalytically reacting a chlorinated organic compound with a fluorination agent under conditions sufficient to form said hydrofluorocarbon compound, said chlorinated organic compound having the formula:CH.sub.b Cl.sub.c F.sub.d CH.sub.e CHCl.sub.ewhere b=0, 1 or 2; c=0, 1, 2, or 3; d=0, 1, 2 or 3; and e=1 or 2 with the provisos that b+c+d=3, c+e>1 and b+e<4.
    Type: Grant
    Filed: June 25, 1997
    Date of Patent: July 7, 1998
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, Alagappan Thenappan
  • Patent number: 5777154
    Abstract: The present invention relates to methods for preparing 3-amino-4,4,4-trihalocrotonates and their derivatives from a 4,4,4-trihaloacetoacetate derivative and an amine or ammonium salt.
    Type: Grant
    Filed: November 14, 1996
    Date of Patent: July 7, 1998
    Assignee: Rohm and Haas Company
    Inventors: Joshua Anthony Chong, Fereydon Abdesken, Peter Osei-Gyimah
  • Patent number: 5750492
    Abstract: Cationic surfactant compound comprising, in the form of a quaternary ammonium salt, a product of condensation between, on the one hand a fraction of saturated or unsaturated fatty acids, or of derivatives of said acids chosen from the group comprising esters, anhydrides and acid chlorides, and on the other hand at least one tertiary amine, characterized in that, in combination:the alkyl chains of the tertiary amine together contain from 4 to 12 carbon atomsthe alkyl chains of the tertiary amine together contain from 1 to 4 functions each chosen from the group comprising hydroxyl and amine functionsthe fatty acids fraction/tertiary amine mole ratio is between 1.85 and 1.40the fatty acids each possess a hydrocarbon chain in which the number of carbon atoms is between 5 and 23.
    Type: Grant
    Filed: June 10, 1997
    Date of Patent: May 12, 1998
    Assignee: Stepan Europe
    Inventors: Jean-Pierre Contet, Stephane Courdavault Duprat, Yvan Storet, Jean-Francois Vindret
  • Patent number: 5714517
    Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops. Polar compounds, for example, 3,4,4-trifluoro-3-butene-1-amine or 3,4,4-trifluoro-3-butenoic acid, are particularly useful for systemic control of pests. Novel method and intermediates for the preparation of 3,4,4-trifluoro-3-butene-1-amine are also provided.
    Type: Grant
    Filed: August 22, 1996
    Date of Patent: February 3, 1998
    Assignee: Monsanto Company
    Inventor: Peter Gerrard Ruminski
  • Patent number: 5712411
    Abstract: A process is provided for the synthesis of N-vinylformamidopropionates by the reaction of NVF with acrylic and methacrylic acid esters in the presence of a metal hydride catalyst. This process allows for the improved production of mono-functional monomers and also for the synthesis of new multi-functional monomers which are useful as crosslinkers and chain extenders in photo-cure applications.
    Type: Grant
    Filed: December 14, 1995
    Date of Patent: January 27, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Ning Chen, Walter Louis Renz, Robert Krantz Pinschmidt, Jr., William Eamon Carroll
  • Patent number: 5672731
    Abstract: Novel unsaturated compounds comprising the 3-(N-vinylformamido)propionates and 2-methyl-3-(N-vinylformamido)propionates, or the corresponding propionamides, are obtained by the Michael addition reaction of N-vinylformamide with an acrylic or methacrylic acid ester. These compounds are useful as monomers in free radical polymerizations, particularly as components of photocurable coatings.
    Type: Grant
    Filed: September 13, 1995
    Date of Patent: September 30, 1997
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Ning Chen, Walter Louis Renz, Robert Krantz Pinschmidt, Jr.
  • Patent number: 5637743
    Abstract: Cationic surfactant compound comprising, in the form of a quaternary ammonium salt, a product of condensation between, on the one hand a fraction of saturated or unsaturated fatty acids, or of derivatives of said acids chosen from the group comprising esters, anhydrides and acid chlorides, and on the other hand at least one tertiary amine, characterized in that, in combination:the alkyl chains of the tertiary amine together contain from 4 to 12 carbon atomsthe alkyl chains of the tertiary amine together contain from 1 to 4 functions each chosen from the group comprising hydroxyl and amine functionsthe fatty acids fraction/tertiary amine mole ratio is between 1.85 and 1.40the fatty acids each possess a hydrocarbon chain in which the number of carbon atoms is between 5 and 23.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: June 10, 1997
    Assignee: Stepan Europe
    Inventors: Jean-Pierre Contet, Stephane C. Duprat, Lionel Godefroy, Paul Nivollet, Didier Ray, Yvan Storet, Jean-Francois Vindret
  • Patent number: 5621144
    Abstract: New compounds are described typically having the formula CH.sub.3 C(CH.sub.2 R).sub.3 or ZCH.sub.2 C(CH.sub.2 R).sub.3 where R is a fluorohydrocarbon or perfluorocarbon group, preferably containing 4-16 carbon atoms and more F atoms that H atoms. Z is a hydrophilic group which may make the compound self-emulsifiable. The compounds are useful as oxygen transport agents in vivo, for which purpose aqueous emulsions are used, as a blood substitute.
    Type: Grant
    Filed: January 9, 1995
    Date of Patent: April 15, 1997
    Assignee: Isis Innovation Limited
    Inventor: Stephen R. Cooper
  • Patent number: 5616764
    Abstract: The present invention relates to the preparation of polymers bearing reactive functional groups. More particularly, this invention relates to the preparation of polymers containing functional acetoacetate groups and then following the polymerization reacting the acetoacetate group with a functional amine to form an enamine.Polymers of the present invention have many uses including coatings, sealants, adhesives and saturant applications, and are most useful as solutions or dispersions in water or water-cosolvent mixtures.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: April 1, 1997
    Assignee: Rohm and Haas Company
    Inventors: Alvin C. Lavoie, Daniel A. Bors, Ward T. Brown
  • Patent number: 5561162
    Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops. Polar compounds, for example, 3,4,4-trifluoro-3-butene-1-amine or 3,4,4-trifluoro-3-butenoic acid, are particularly useful for systemic control of pests. Novel method and intermediates for the preparation of 3,4,4-trifluoro-3-butene-1-amine are also provided.
    Type: Grant
    Filed: March 8, 1995
    Date of Patent: October 1, 1996
    Assignee: Monsanto Company
    Inventor: Peter G. Ruminski
  • Patent number: 5559267
    Abstract: Chiral 1,4-diol cyclic sulfates and their use as precursors in the preparation of chiral phospholane ligands, and chiral complexes useful as catalysts for carrying out enantioselective reactions.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: September 24, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Mark J. Burk
  • Patent number: 5559268
    Abstract: A process for the preparation of N-substituted dehydroamino acid esters by contacting a .beta.-hydroxy-.alpha.-amino acid ester or N- or O-substituted .beta.-hydroxy-.alpha.-amino acid ester with an excess of acetic anhydride and a base is disclosed.
    Type: Grant
    Filed: November 17, 1994
    Date of Patent: September 24, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William A. Nugent
  • Patent number: 5476974
    Abstract: Normally liquid, omega-hydrofluoroalkyl ether compounds (and selected mixtures thereof) have a saturated perfluoroaliphatic chain of carbon atoms interrupted by one or more ether oxygen atoms. The compounds can be prepared, e.g., by decarboxylation of the corresponding fluoroalkyl ether carboxylic acids and are useful, e.g., in cleaning and drying applications.
    Type: Grant
    Filed: May 20, 1994
    Date of Patent: December 19, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: George G. I. Moore, Miguel A. Guerra
  • Patent number: 5473099
    Abstract: This invention relates to a novel synthesis of 4-amino-5-hexenoic acid by thermal rearrangements, and to the novel intermediates produced thereby.
    Type: Grant
    Filed: April 11, 1995
    Date of Patent: December 5, 1995
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventor: Patrick Casara
  • Patent number: 5463110
    Abstract: Novel unsaturated compounds comprising the 3-(N-vinylformamido)propionates and 2-methyl-3-(N-vinylformamido)propionates are obtained by the Michael addition reaction of N-vinylformamide with an acrylic or methacrylic acid ester. These compounds are useful as monomers in free radical polymerizations, particularly as components of photocurable coatings.
    Type: Grant
    Filed: May 20, 1994
    Date of Patent: October 31, 1995
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Ning Chen, Walter L. Renz, Robert K. Pinschmidt, Jr.
  • Patent number: 5446187
    Abstract: Diphosphonic acids of formula (I) are useful as antitumor agents.
    Type: Grant
    Filed: October 8, 1993
    Date of Patent: August 29, 1995
    Assignee: Boehringer Mannheim Italia S.p.A.
    Inventors: Sergio Tognella, Valeria Livi, Ernesto Menta, Silvano Spinelli
  • Patent number: 5446192
    Abstract: .beta.-Aminoacrylic acid esters can be prepared by reacting acetic acid esters of the formulaH.sub.2 CR.sub.1 --COOR.sup.2 (II)with aminal esters of the formula ##STR1## at 0.5-10 bar and 50.degree.-170.degree. C. in an aprotic polar solvent. The radicals R.sup.1 to R.sup.7 are as defined in the description.
    Type: Grant
    Filed: March 3, 1993
    Date of Patent: August 29, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Kraus, Heinz-Ulrich Blank, Gerhard Marzolph
  • Patent number: 5442088
    Abstract: Process for the preparation of phosphorus-containing L-amino acids, their derivatives and intermediates for this processL-amino acids of the formula I and salts thereof, ##STR1## in which R.sup.1 to R.sup.5 are defined as in claim 1 and n is 0 or 1, are obtained according to the invention bya) reacting an optically active S-homoserine lactone of the formula II, ##STR2## with hydrogen chloride in the presence of an alcohol of the formula R.sup.5 --OH to give novel compounds of the formula III, ##STR3## in which R.sup.3, R.sup.4 and R.sup.5 are defined as in formula I, except that R.sup.5 =H, andb) reacting the resulting compound of formula III with a compound of formula IV,R.sup.1 (O).sub.n -R(OR.sup.2).sub.2 (IV)and if desired, hydrolyzing the product to give a compound of formula I, in which R.sup.5 =H.
    Type: Grant
    Filed: July 7, 1994
    Date of Patent: August 15, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Michael Hoffmann
  • Patent number: 5395971
    Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X--Y).
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: March 7, 1995
    Assignee: The Board of Regents of The University of Oklahoma
    Inventors: Kenneth M. Nicholas, Anurag S. Srivastava
  • Patent number: 5391811
    Abstract: .alpha.-fluoro-.beta.-dicarbonyl compounds are prepared by reacting a halogenated dicarbonyl compound at temperatures of 20.degree. to 100.degree. C. with an addition product of hydrogen fluoride and a trialkylamine. This process is easy to carry out in technical terms and can also be carried out on a large scale.
    Type: Grant
    Filed: November 3, 1993
    Date of Patent: February 21, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stefan Bohm, Albrecht Marhold
  • Patent number: 5389680
    Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops. Polar compounds, for example, 3,4,4-trifluoro-3-butene-1-amine or 3,4,4-trifluoro-3-butenoic acid, are particularly useful for systemic control of pests. Novel method and intermediates for the preparation of 3,4,4-trifluoro-3-butene-1-amine are also provided.
    Type: Grant
    Filed: October 18, 1993
    Date of Patent: February 14, 1995
    Assignee: Monsanto Company
    Inventor: Peter G. Ruminski
  • Patent number: 5380936
    Abstract: This invention relates to a novel synthesis of 4-amino-5-hexenoic acid by thermal rearrangements, and to the novel intermediates produced thereby.
    Type: Grant
    Filed: January 19, 1994
    Date of Patent: January 10, 1995
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventor: Patrick Casara
  • Patent number: 5349109
    Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X-Y).
    Type: Grant
    Filed: August 26, 1993
    Date of Patent: September 20, 1994
    Assignee: The Board of Regents of the University of Oklahoma
    Inventors: Kenneth M. Nicholas, Anurag S. Srivastava
  • Patent number: 5286879
    Abstract: An improved process for preparing mono-condensation derivatives of adipic acid with fewer steps and better purity is disclosed. In particular, this process comprises: (a) forming relatively concentrated and pure cyclic monomeric adipic anhydride by depolymerization and concentration starting from polymeric adipic anhydride; and (b) adding a condensation reactant having an active hydrogen, e.g., a primary or secondary amine, to said cyclic monomeric adipic anhydride to form the corresponding mono-condensation derivative of adipic acid.
    Type: Grant
    Filed: October 5, 1992
    Date of Patent: February 15, 1994
    Assignee: The Procter & Gamble Company
    Inventors: James C. Letton, Larry E. Miller
  • Patent number: 5274062
    Abstract: A polymer comprising a carbon-carbon backbone chain and at least one N-(substituted oxalyl)carbamoyl group of the formula: --CO--NH--CO--CO--OR wherein R is a hydrocarbon group as a side chain attached to said backbone chain.
    Type: Grant
    Filed: November 24, 1992
    Date of Patent: December 28, 1993
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Yuji Suzuki, Satoshi Urano, Hirotoshi Umemoto, Ryuzo Mizuguchi, Kei Aoki, Noriyuki Tsuboniwa
  • Patent number: 5252745
    Abstract: Antimicrobial compounds of the formula ##STR1## wherein R.sup.1 is selected from the group consisting of H, an amine protective group, and a moiety of the formula ##STR2## wherein R.sup.2, R.sup.5, and R.sup.6 are independently selected from H and an amine protective group;R.sup.3 and R.sup.4 are independently selected from H, lower alkyl, aryl, arylalkyl, CH.sub.2 OR, CH.sub.2 SR or CH(CH.sub.3)OR;R=H, propargyl lower alkyl, arylalkyl or aryl;wherein R.sup.1 and R.sup.2 or R.sup.5 and R.sup.6 can be joined to form a ring; and wherein when R.sup.1 and R.sup.2 or R.sup.5 and R.sup.6 are both H, the compound is either in free base form or in salt form.
    Type: Grant
    Filed: May 21, 1991
    Date of Patent: October 12, 1993
    Assignee: Rohm and Haas Company
    Inventors: Margaret M. Bowers-Daines, Barry C. Lange
  • Patent number: 5175344
    Abstract: The invention relates to unsaturated amino acids of the formula I ##STR1## in which R.sup.1 represents hydroxy or etherified hydroxy, R.sup.2 represents hydrogen, alkyl, hydroxy or etherified hydroxy, R.sup.3 represents hydrogen, alkyl, haloalkyl, hydroxyalkyl, lower alkoxyalkyl, arylalkyl, lower alkenyl, halogen or aryl, R.sup.4 represents hydrogen, alkyl or aryl, R.sup.5 represents hydrogen or alkyl, R.sup.6 represents carboxy or esterified or amidated carboxy, R.sup.7 represents amino or amino substituted by alkyl or acyl, A represents unsubstituted or alkyl-substituted .alpha.,.omega.-alkylene having from 1 to 3 carbon atoms or represents a bond, and B represents methylene or a bond, with the proviso that A is other than a bond when B represents a bond, and salts thereof. They can be manufactured, for example, in accordance with the Michaelis-Arbuzov reaction and can be used as pharmacologically active substances.
    Type: Grant
    Filed: July 17, 1991
    Date of Patent: December 29, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Christof Angst, Derek E. Brundish, John G. Dingwall, Graham E. Fagg, Hans Allgeier, Guido Bold, Rudolf Duthaler, Roland Heckendorn, Antonio Togni
  • Patent number: 5166373
    Abstract: The present invention provides novel acyclic terpenes of the formula: ##STR1## which are useful as intermediates for the industrially advantageous production of sarcophytol A.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: November 24, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5147867
    Abstract: Dipeptide mimics which contain phosphorus and their pharmaceutical use and preparation are disclosed. The compounds have dehydropeptidase (DHP) enzyme inhibitor activity.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: September 15, 1992
    Assignee: Merck & Co., Inc.
    Inventors: William H. Parsons, William R. Schoen, Arthur A. Patchett
  • Patent number: 5131921
    Abstract: Motor fuel compositions comprising gasoline are improved to control octane requirement increase (ORI) by including an ester of an N-acyl sarcosinate acid or salt and a polyether polyol including oxyalkylene units selected from oxypropylene and/or oxybutylene.
    Type: Grant
    Filed: October 9, 1990
    Date of Patent: July 21, 1992
    Assignee: Texaco Inc.
    Inventors: Rodney L. Sung, Daniel T. Daly
  • Patent number: 5096700
    Abstract: The subject invention involves halogenated amino acid derivatives useful as antimicrobial agents having the structure: ##STR1## wherein --R is hydrogen or 2-aminoethyl; --R' is hydroxy, alkoxy, aryloxy, or an amino acid residue bonded at the amino nitrogen; --R" is hydrogen or an amino acid residue bonded at the carbonyl carbon; --X is halogen; and --Y is hydrogen or halogen.
    Type: Grant
    Filed: September 28, 1990
    Date of Patent: March 17, 1992
    Assignee: The Procter & Gamble Company
    Inventors: William L. Seibel, Joseph H. Gardner
  • Patent number: 5077046
    Abstract: A polyprenyl composition consisting essentially of a mixture of polyprenyl compounds represented by the following formula ##STR1## wherein A.sub.1 represents a hydroxyl or acetyloxy group, ##STR2## represents a trans-isoprene unit, ##STR3## represents a cis-isoprene unit, and n is an integer of from 11 to 19, said mixture containing substantial amounts of at least three compounds of formula (I) wherein n represents 14, 15 and 16 respectively as essential ingredients in a total amount of at least 70% by weight based on the weight of the mixture; and new compounds derived from the polyprenyl compounds of formula (I). These composition and compounds are useful for the synthesis of mamammalian dolichols.
    Type: Grant
    Filed: September 21, 1989
    Date of Patent: December 31, 1991
    Assignee: Kuraray Co., Ltd.
    Inventors: Yasuyuki Tanaka, Koichi Ibata, Masao Mizuno, Yoichi Ninagawa, Takashi Nishida
  • Patent number: 5051413
    Abstract: The invention relates to unsaturated amino acids of the formula I ##STR1## in which R.sup.1 represents hydroxy or etherified hydroxy, R.sup.2 represents hydrogen, alkyl, hydroxy or etherified hydroxy, R.sup.3 represents hydrogen, alkyl, haloalkyl, hydroxyalkyl, lower alkoxyalkyl, arylalkyl, lower alkenyl, halogen or aryl, R.sup.4 represents hydrogen, alkyl or aryl, R.sup.5 represents hydrogen or alkyl, R.sup.6 represents carboxy or esterified or amidated carboxy, R.sup.7 represents amino or amino substituted by alkyl or acyl, A represents unsubstituted or alkyl-substituted .alpha.,.omega.-alkylene having from 1 to 3 carbon atoms or represents a bond, and B represents methylene or a bond, with the proviso that A is other than a bond when B represents a bond, and salts thereof. They can be manufactured, for example, in accordance with the Michaelis-Arbuzov reaction and can be used as pharmacologically active substances.
    Type: Grant
    Filed: December 18, 1989
    Date of Patent: September 24, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Christof Angst, Derek E. Brundish, John G. Dingwall, Graham E. Fagg, Hans Allgeier, Guido Bold, Rudolf Duthaler, Roland Heckendorn, Antonio Togni
  • Patent number: 5041643
    Abstract: A process for the production of R(+)-aminocarnitine and S(-)-aminocarnitine is disclosed by resolution of the mixture of the diastereoisomers of N-(alpha-methylbenzyl) aminocarnitine benzyl ester chloride, wherein the separated diastereoisomers are subsequently debenzylated to give R(+)-aminocarnitine chloride and S(-)-aminocarnitine chloride.
    Type: Grant
    Filed: April 10, 1990
    Date of Patent: August 20, 1991
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Maria O. Tinti, Domenico Misiti
  • Patent number: 5030747
    Abstract: .beta.-Amino-acrylic acid esters of the formula(R.sup.1 R.sup.2)NCH.dbd.CR.sup.3 --COOR.sup.4can be obtained by reaction of .beta.-hydroxy-acrylic acid ester alkali metal salts of the formulaMe.sup..sym. .crclbar. OCH.dbd.CR.sup.3 --COOR.sup.4with ammonium salts of the formula(R.sup.1 R.sup.2) NH.sub.2.sup..sym. .crclbar.according to the general reaction equation(R.sup.1 R.sup.2) NH.sub.2 X+MeOCH.dbd.CR.sup.3 --COOR.sup.4 .fwdarw.(R.sup.1 R.sup.2) NCH.dbd.CR.sup.3 --COOR.sup.4 +MeX.dbd.H.sub.2 OR.sup.1, R.sup.2, R.sup.3, R.sup.4, Me.sup..sym. and X.sup..crclbar. having the meaning indicated in the description and the reaction being carried out in an aprotic organic solvent, in which the reaction components are suspended, as the reaction medium and it being possible to replace a part of the aprotic organic solvent by a protic organic solvent which is miscible with the aprotic solvent to give a homogeneous phase.
    Type: Grant
    Filed: March 19, 1990
    Date of Patent: July 9, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Erich Wolters, Friedrich-Wilhelm Ullrich, Halmut Kraus, Gerhard Marzolph, Gunter Silber
  • Patent number: 5010189
    Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonization of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.
    Type: Grant
    Filed: October 24, 1989
    Date of Patent: April 23, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst
  • Patent number: 5010200
    Abstract: This invention provides novel insecticidally and acaricidally active pyrimidine derivatives of formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is selected from alkyl; alkenyl; alkynyl; haloalkyl; haloalkenyl; and cycloalkyl optionally substituted by alkyl or halogen;R.sup.2 is selected from alkyl; haloalkyl; alkoxy; alkylamino; dialkylamino; halogen; cycloalkyl optionally substituted by halogen or alkyl; and phenyl optionally substituted by alkyl, haloalkyl, halogen or alkoxy;R.sup.3 is selected from hydrogen and halogen;R.sup.4 is the residue of an alcohol of formula R.sup.4 -OH which forms an insecticidal ester when combined with chrysanthemic acid, permethrin acid or cyhalothrin acid; andX is selected from oxygen and sulphur.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: April 23, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Edward McDonald, Roger Salmon, Alan J. Whittle, Michael G. Hutchings
  • Patent number: RE34652
    Abstract: Novel fluorinated, acrylamide monomers are prepared from 2-alkenyl azlactones reacted with fluorinated alcohols. The novel monomers have the formula ##STR1## wherein R.sup.1 and R.sup.6 are independently hydrogen or methyl;R.sup.2 and R.sup.3 independently can be an alkyl, cycloalkyl, or aryl group, or R.sup.2 and R.sup.3 taken together with the carbon to which they are joined can form a carbocyclic ring containing 4 to 12 ring atoms;R.sup.4 and R.sup.5 are independently hydrogen or lower alkyl;a is 0 or 1;b is 1 or 2;X is a single bond, CH.sub.2, CH.sub.2 OCH.sub.2, and CH.sub.2 CH.sub.2 OCH.sub.2 ; andR.sub.F is a substantially perfluorinated alkyl, cycloalkyl, or aryl group when b is 1 and perfluorinated alkylene when b is 2.Novel polymers and copolymers can be prepared from the monomers of the invention.
    Type: Grant
    Filed: June 3, 1992
    Date of Patent: June 28, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Steven M. Heilmann, Larry R. Krepski, Dean M. Moren, Jerald K. Rasmussen, Howell K. Smith, II