Halogen Or Unsaturation Patents (Class 562/574)
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Publication number: 20020082450Abstract: An industrially advantageous method of producing &bgr;-halogeno-&agr;-aminocarboxylic acids is provided. Methods are also provided of producing optically active N-protected-S-phenylcysteines having high optical purity and of intermediates thereof, respectively, in which the above production method is utilized.Type: ApplicationFiled: December 27, 2001Publication date: June 27, 2002Inventors: Koki Yamashita, Kenji Inoue, Koichi Kinoshita, Yasuyoshi Ueda, Hiroshi Murao
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Patent number: 6372941Abstract: An industrially advantageous method of producing &bgr;-halogeno-&agr;-aminocarboxylic acids is provided. Methods are also provided of producing optically active N-protected-S-phenylcysteines having high optical purity and of intermediates thereof, respectively, in which the above production method is utilized. A method of producing &bgr;-halogeno-&agr;-aminocarboxylic acids or salts thereof is disclosed which comprises halogenating the hydroxyl group of a &bgr;-hydroxy-&agr;-aminocarboxylic acid (in which the basicity of the amino group in &agr;-position is not masked by the presence of a substituent on said amino group) or a salt thereof with an acid with a halogenating agent.Type: GrantFiled: August 16, 1999Date of Patent: April 16, 2002Assignee: Kaneka CorporationInventors: Koki Yamashita, Kenji Inoue, Koichi Kinoshita, Yasuyoshi Ueda, Hiroshi Murao
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Patent number: 6348092Abstract: A composition consisting of the reaction product of a halogenated carboxylic acid, an amine, and optionally a fatty acid. The composition has biocidal properties and enhances pigment dispersibility.Type: GrantFiled: October 25, 1999Date of Patent: February 19, 2002Inventor: George K. Atkinson
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Patent number: 6307103Abstract: 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: GrantFiled: March 28, 2000Date of Patent: October 23, 2001Assignee: American Cyanamid CompanyInventors: Hans-Peter Niedermann, Dieter Gutheil
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Patent number: 6306344Abstract: The present invention provides a method for retaining or enriching &ggr;-aminobutyric acid in green grass leaves, which comprises the step of subjecting green grass leaves or processed products thereof to at least one treatment selected from the group consisting of incubation treatment, anaerobic treatment, and microwave treatment.Type: GrantFiled: April 25, 2000Date of Patent: October 23, 2001Assignee: Toyo Shinyaku Co., Ltd.Inventor: Toshimitsu Hattori
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Patent number: 6180826Abstract: New water-soluble polyperfluoroalkyl surfactants derived from functional polycarboxylic polymers, characterized by the fact they have alco-oleophobic properties, to be used in the make-up of protein or synthetic foam for extinguishing fires caused not only by hydrocarbons, but also by polar liquids (alcohol, ethers, esters, etc.) without requiring the use of thickening agents, such as polysaccharides.Type: GrantFiled: January 30, 1998Date of Patent: January 30, 2001Assignee: Laboratoire 3 SInventors: Istvan Szonyi, Stephane Szonyi, Francois Szonyi
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Patent number: 6166259Abstract: 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: GrantFiled: March 28, 2000Date of Patent: December 26, 2000Assignee: American Cyanamid CompanyInventors: Rudi Eisenacht, Hans-Peter Niedermann, Dieter Landau
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Patent number: 6156222Abstract: Perfluoroalkyl-allyloxy- and perfluoroalkyl-iodopropyloxy-substituted polyaminoacids or poly-R.sub.F -fluoroallyl-substituted polyaminoacids which contain, in random distribution, q units of A-1, r units of A-2, s units of A-3 and t units of A-4 in which A-1 and A-2 are perfluoroalkyl-substituted amino groups of the formulae ##STR1## A-3 is a hydrophilically substituted amino or amido group of the formula ##STR2## and A-4 is a substituted amino or amido group of the formula ##STR3## where the variables are as defined herein, are useful to provide oil repellency to paper and as foam stabilizers in alcohol resistant--aqueous fire-fighting foam fire-fighting foam compositions.Type: GrantFiled: January 20, 1999Date of Patent: December 5, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: John Jennings, Ted Deisenroth, Marlon Haniff
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Patent number: 6069272Abstract: The invention relates to a three-step synthesis of vinyl glycine (1) using a cheap, commercially available starting material (3-butenenitrile (2)) and using cheap, simple reagents. Also disclosed is a convenient optical resolution of the N-tert.butyloxycarbonyl derivative by papain-catalyzed enantioselective esterification in a two-phase system.Type: GrantFiled: April 28, 1997Date of Patent: May 30, 2000Assignee: Hoechst AktiengesellschaftInventors: David Herbert George Crout, Keith Oliver Hallinan
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Patent number: 6018050Abstract: The invention relates to a new process for the preparation of optically active amino acids and amino acid derivatives of the general formula (I), wherein *, X and R.sup.1 to R.sup.4 have the meaning given in the description. Starting from commercially obtainable (-)-menthol or (+)-menthol, the enantiomerically pure compounds of the formula (I) are obtained in high yields. The method is particularly suitable for the preparation of sterically demanding amino acids and amino acid derivatives.Type: GrantFiled: April 30, 1998Date of Patent: January 25, 2000Assignee: Degussa AktiengesellschaftInventors: Hans-Josef Altenbach, Matthias Kottenhahn, Annegret Vogt, Mike Matthaus, Andreas Grundler, Michael Hahn
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Patent number: 5905127Abstract: Mesogens are provided based on substituted unsaturated carboxylic acids such as acrylic and methacrylic acid. Substitution of a variety of hydrophobic tails onto the carboxylic acid or acid derivative via the vinyl carbon proximal to the carbonyl of the carboxylic acid results in mesogens that are capable of forming thermotropic and single-phase lyotropic mesophases over a broad range of compositions. The mesophases can be polymerized to lock in the ordered phases.Type: GrantFiled: April 8, 1997Date of Patent: May 18, 1999Assignee: The University of Southern MississippiInventors: Robert Y Lochhead, Lon J Mathias
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Patent number: 5872287Abstract: Provided are an amphipathic compound represented by any of the following Formulas: ##STR1## (R.sub.1 is a linear or branched, saturated hydrocarbon group having 6 to 48 carbon atoms, or a linear or branched, unsaturated hydrocarbon group containing 1 to 12 unsaturated double bond and having 6 to 48 carbon atoms; Y is NH, N--(CH.sub.2 --CH.dbd.CH.sub.2), or O; Q is --CH.sub.2 --C(R.sub.2).dbd.CH.sub.2 or --R.sub.4 --O--CO--C(R.sub.2).dbd.CH.sub.2 ; and M is alkali metal, an ammonium group, or --(CH.sub.2 CH.sub.2 O).sub.m H), a copolymer of the amphipatic compound with a copolymerizable ethylenically unsaturated compound and, a paper making additive containing a water soluble or dispersible high molecular compound as an active ingredient and processes for producing these high molecular compounds.Type: GrantFiled: June 4, 1996Date of Patent: February 16, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Toshihiko Takaki, Masaru Tanabe, Hiroshi Itoh, Masayuki Yanagi, Shoko Oyanagi, Hiroyoshi Watanabe, Atsushi Utsunomiya, Yasuko Ono, Masanori Tsuchihashi
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Patent number: 5856538Abstract: N-acylamino carboxylic acids and N-acylamino sulfonic acids and their alkali metal salts from the technical alkali metal salts of amino carboxylic acids and amino sulfonic acids, respectively, with an active content of 50-95% by weight, based on the solids content of the technical alkali metal salts, and from alkyl carboxylates, are prepared by(a) preparing a suspension of the solid anhydrous technical alkali metal salts of the amino carboxylic acids or amino sulfonic acids in the alkyl carboxylates,(b) reacting this suspension by adding more than 30 to 150 mol % of strong bases to give the alkali metal salts of the N-acylamino carboxylic acids or N-acylamino sulfonic acids, and(c) if required preparing therefrom the free N-acylamino carboxylic acids or N-acylamino sulfonic acids in a conventional way by adding acids.Type: GrantFiled: March 24, 1997Date of Patent: January 5, 1999Assignee: BASF AktiengesellschaftInventors: Beate Strecker, Alfred Oftring, Dieter Hertel, Georg Schuh
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Patent number: 5808146Abstract: The invention provides novel amino acid compounds of use in detecting and evaluating brain and body tumors. These compounds combine the advantageous properties of 1-amino-cycloalkyl-1-carboxylic acids, namely, their rapid uptake and prolonged retention in tumors with the properties of halogen substituents, including certain useful halogen isotopes including fluorine-18, iodine-123, iodine-125, iodine-131, bromine-75, bromine-76, bromine-77 and bromine-82.In one aspect, the invention features amino acid compounds that have a high specificity for target sites when administered to a subject in vivo. Preferred amino acid compounds show a target to non-target ratio of at least 5:1, are stable in vivo and substantially localized to target within 1 hour after administration. An especially preferred amino acid compound is ?.sup.18 F!-1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC).In another aspect, the invention features pharmaceutical compositions comprised of an .alpha.Type: GrantFiled: November 9, 1995Date of Patent: September 15, 1998Assignee: Emory UniversityInventors: Mark M. Goodman, Timothy Shoup
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Patent number: 5700840Abstract: Fluorinated alkene compounds useful for controlling nematodes, insects, and acarids that prey on agricultural crops, these compounds having the formula BrCF.sub.2 CFClCH.sub.2 CO--R where R is R.sub.1 or R.sub.2. R.sub.1 is --SR.sub.5, halogen, --NHOH or --NR.sub.5 R.sub.6, where R.sub.5 and R.sub.6 are independently H; an aliphatic or aromatic group; an aliphatic amine group; an aliphatic carboxylic acid group; or R.sub.5 and R.sub.6 when taken with the N of R.sub.1 are an amino acid or a cyclic group or R.sub.1 is --OR.sub.5, where R.sub.5 is an aliphatic or aromatic group; an aliphatic amine group; or an aliphatic carboxylic acid group. R.sub.2 is --SR.sub.5 or --NR.sub.5 R.sub.6, where R.sub.5 and R.sub.6 are independently H; an aliphatic, aromatic or heterocyclic group; an aliphatic amine group; an aliphatic carboxylic acid group; R.sub.5 and R.sub.6 when taken with the N of R.sub.2 are an amino acid or a cyclic group; R.sub.5 and R.sub.6 when taken with the N of R.sub.Type: GrantFiled: May 23, 1995Date of Patent: December 23, 1997Assignee: Monsanto CompanyInventors: Dennis Paul Phillion, Peter Gerrard Ruminski, Gopichand Yalamanchili
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Patent number: 5672583Abstract: Novel Carboxy-peptidyl compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophobic epidermolysis bullosa, coronary thrombosis associated with atherosclerotic plaque rupture, and aneurysmal aortic disease. The matrix metalloendoproteinases are a family of zinc-containing proteinases including but not limited to stromelysin, collagenase, and gelatinase, that are capable of degrading the major components of articular cartilage and basement membranes. The inhibitors claimed herein may also be useful in preventing the pathological sequelae following a traumatic injury that could lead to a permanent disability. These compounds may also have utility as a means for birth control by preventing ovulation or implantation.Type: GrantFiled: May 17, 1995Date of Patent: September 30, 1997Assignee: Merck & Co., Inc.Inventors: Kevin Chapman, William Hagmann, Philippe Durette, Craig Esser, Ihor Kopka, Charles Caldwell
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Patent number: 5654477Abstract: The present invention relates to a novel enantiospecific processes for preparing (S)-4-amino-hepta-5,6-dienoic acid and pharmaceutically acceptable salts thereof, which is useful as an irreversible inhibitor of GABA-T, to novel intermediates thereof, and a process for preparing an intermediate thereof.Type: GrantFiled: March 6, 1995Date of Patent: August 5, 1997Assignee: Merrell Pharmaceuticals Inc.Inventor: H. Michael Kolb
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Patent number: 5648528Abstract: New saturated fluoroalkylamines and carboxyalkylbetaines and alkylsulfobetaines derived therefrom, and mixtures containing the new fluoroalkylamines and mixtures containing the new fluorobetaines are described. The saturated fluoroalkylamines conform to the formula below ##STR1## in which n is an integer from 3 to 17 and R.sup.1 and R.sup.2 are C.sub.1 to C.sub.4 -alkyl, C.sub.1 to C.sub.4 -hydroxyalkyl or hydrogen, with the proviso that only one of the two substituents R.sup.1 and R.sup.2 is hydrogen. The carboxyalkylbetaines and sulfobetaines and the mixtures thereof are highly effective products for reducing the surface tension of water/air systems and the interfacial tension of water/hydrocarbon systems.Type: GrantFiled: June 7, 1995Date of Patent: July 15, 1997Assignee: Hoechst AktiengesellschaftInventors: Gunter Prossel, Wolfgang Knaup, Frank Wehowsky
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Patent number: 5455234Abstract: Mammalian hair growth is reduced by applying to the skin an inhibitor of a cysteine synthetic pathway enzyme.Type: GrantFiled: March 16, 1994Date of Patent: October 3, 1995Inventors: Gurpreet S. Ahluwalia, Douglas Shander
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Patent number: 5442088Abstract: 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: GrantFiled: July 7, 1994Date of Patent: August 15, 1995Assignee: Hoechst AktiengesellschaftInventor: Michael Hoffmann
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Patent number: 5436372Abstract: The invention is intended to provide novel solid state displacement elements that have an extent of displacement. The solid state displacement element has an intercalation compound in which a polar compound (B) is mixed with an inorganic layered compound (A), and produces a strain when a voltage is applied.Type: GrantFiled: April 9, 1992Date of Patent: July 25, 1995Assignee: Nippon Soken, Inc.Inventors: Hiroyuki Yoshida, Eturo Yasuda, Yoshiaki Fukushima
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Patent number: 5399590Abstract: The invention relates to the field of organic chemistry and more particularly to that of therapeutic chemistry.More particularly it relates to new quaternary ammonium salts of general formula (I): ##STR1## in which Hal is a halogen atom other than fluorine R and R.sub.1, identical or different, are lower alkyl radicals, n is an integer varying from 2 to 16, Z is an alkenyl radical having up to 3 carbon atoms, a carboxyl, or the OR.sub.2 group in which R.sub.2 is a hydrogen, a lower alkyl radical, an acyl remainder, a tocol radical, a sterol radical or a carboxamide chain and A is a hydroxyl or an anion of a mineral or organic acid.The compounds according to the invention are the active ingredients of pharmaceutical compositions with an anti-tumorous and/or immuno-suppressive action.Type: GrantFiled: January 14, 1993Date of Patent: March 21, 1995Inventor: Jean M. Gastaud
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Patent number: 5380936Abstract: This invention relates to a novel synthesis of 4-amino-5-hexenoic acid by thermal rearrangements, and to the novel intermediates produced thereby.Type: GrantFiled: January 19, 1994Date of Patent: January 10, 1995Assignee: Merrell Dow Pharmaceuticals Inc.Inventor: Patrick Casara
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Patent number: 5324504Abstract: Accordingly, the present invention is directed to biological compounds derivatized so as to contain at least one perfluoro-t-butyl moiety for use in fluorine-19 NMR and/or MRI studies. The perfluoro-t-butyl (PFTB) moiety, ##STR1## is an excellent reported group for fluorine-19 NMR/MRI. It is a source of nine magnetically equivalent fluorine nuclei which generate a single intense resonance for each detection in spectroscopy or imaging. This signal is a sharp singlet, not split by neighboring nuclei or spread over a wide frequency range and eliminates any change of ghost images which might arise from multiple resonances. These spectral properties ensure a maximum signal-to-noise ratio (S/N) for readily detecting this moiety. The foregoing allows either reduction in the concentration of the derivatized compound, ability to use MRI instruments with lower field strengths, a reduction in imaging times, or a combination of the foregoing as a result of this moiety producing a single, sharp, intense resonance.Type: GrantFiled: March 4, 1993Date of Patent: June 28, 1994Assignees: The Johns Hopkins University, Towson State UniversityInventors: Walter J. Roger, Jr., Thomas S. Everett
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Patent number: 5153358Abstract: A novel process for the preparation of .alpha.-alkylated .alpha.-amino acids and .alpha.-halogenated .alpha.-amino acids is disclosed. These .alpha.-alkylated .alpha.-amino acids and .alpha.-halogenated .alpha.-amino acids are useful as intermediates for the preparation of enzyme inhibitors (for example, renin inhibitors) and other peptides or amino acid derivatives or analogs.Type: GrantFiled: January 30, 1991Date of Patent: October 6, 1992Assignee: Abbott LaboratoriesInventor: Thomas M. Zydowsky
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Patent number: 5096700Abstract: 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: GrantFiled: September 28, 1990Date of Patent: March 17, 1992Assignee: The Procter & Gamble CompanyInventors: William L. Seibel, Joseph H. Gardner
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Patent number: 5087728Abstract: A process for producing a carboxylic acid or an ester thereof represented by formula (I): ##STR1## wherein: R represents a hydrogen atom or a lower alkyl group; R.sup.1 represents a lower alkyl group; CH.sub.2 COOR.sup.3, wherein R.sup.3 represents a hydrogen atom or a lower alkyl group; or NHR.sup.4, wherein R.sup.4 represents a formyl group, an acetyl group, a benzoyl group, or a chloroacetyl group, andR.sup.2 represents a hydrogen atom, a lower alkyl group, or a phenyl group,which comprises hydrogenating an unsaturated compound represented by formula (II): ##STR2## wherein R, R.sup.1, and R.sup.2 are as defined above, in the presence of a rhodium or ruthenium complex catalyst having, as a ligand, BICHEP which means 2,2'-bis(dicyclohexylphoshino)-6,6'-dimethyl-1,1'-biphenyl represented by formula (III): ##STR3## is disclosed.Type: GrantFiled: July 11, 1990Date of Patent: February 11, 1992Assignee: Takasago International CorporationInventors: Hiroyuki Nohira, Hidemasa Takaya, Akira Miyashita
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Patent number: 5026909Abstract: A method according to the invention comprises mixing the starting biologically active organic compound, an inorganic vehicle and a catalyst in the form of a platinum-group metal, followed by reacting the resulting mixture with an isotope of hydrogen at a temperature of 373-523 K. and cooling the reaction mixture to a temperature of 288-303 K. and isolation of the desired product therefrom. The invention can be useful, for example, in medical and biological studies.Type: GrantFiled: March 22, 1989Date of Patent: June 25, 1991Inventors: Jury A. Zolotarev, Dmitry A. Zaitsev, Vadim J. Tatur, Nikolai F. Myasoedov
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Patent number: 4954564Abstract: A process for preparing unsaturated nitrogen containing acids such as acrylamidoglycolic acid utilizes a catalyst free route and low pH conditions. An unsaturated amide such as acrylamide is reacted with an aldehyde acid such as acid in an aqueous environment. The unsaturated nitrogen containing acids are typically produced in solution form and can be utilized as such.Type: GrantFiled: July 5, 1988Date of Patent: September 4, 1990Assignee: GenCorp Inc.Inventor: Woodrow W. White
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Patent number: 4942231Abstract: The invention relates to a method of preparing a chlorinated, brominated, radiobrominated, iodinated and/or radioiodinated aromatic or heteroaromatic compound, in which the (hetero)aromatic nucleus optionally comprises one or more additional substituents, by reacting the corresponding halogenated or diazonium-substituted compound in the presence of a water-soluble acid and of copper ions as a catalyst with a likewise water-soluble chloride, bromide radiobromide, iodide or radio-iodide, in which the reaction is carried out in the presence of one or more reduction agents, which are stable in acid medium, in a quantity exceeding the quantity of catalyst. The invention also relates to a composition suitable for diagnostic examination and to a kit for the preparation thereof. The invention further relates to a method and an equipment for the preparation of said composition.Type: GrantFiled: May 17, 1985Date of Patent: July 17, 1990Assignee: Mallinckrodt, Inc.Inventor: John Mertens
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Patent number: 4902334Abstract: A plant metabolism regulating agent comprising as an active ingredient an alpha,beta or beta,gamma-un-saturated carboxylic acid or its derivative. It is useful for controlling the metabolism of a plant, facilitating the growth of a beneficial plant such as cereals by inhibiting the growth of undesirable plants or eradicating them, regulating the growth of a plant and dwarfing a plant.Type: GrantFiled: October 31, 1984Date of Patent: February 20, 1990Assignee: Teijin LimitedInventors: Shizuo Azuma, Toshiyuki Hiramatsu, Teizo Yamaji, Yataro Ichikawa
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Patent number: 4889873Abstract: Novel compounds and compositions which inhibit SRS-A in mammals are disclosed. Methods for preparing said compounds and compositions and methods for their use for treating allergic reactions, inflammation and for reducing the severity of myocardial infarction resulting from heart attack are disclosed.Useful intermediates for preparing said compounds are also disclosed.Type: GrantFiled: November 17, 1987Date of Patent: December 26, 1989Assignee: Schering CorporationInventors: Anil K. Saksena, Jesse K. Wong, Pietro Mangiaracina
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Patent number: 4806680Abstract: Described bare 3-halovinylglycines and their amino acid dipeptide and oligopeptide conjugates, a new class of efficient antibacterial agents, pharmaceutical compositions containing them as active ingredients, and methods of synthesis. The compounds are thought to interfere in bacterial cell wall synthesis.Type: GrantFiled: November 12, 1987Date of Patent: February 21, 1989Assignee: Merck & Co., Inc.Inventors: David Taub, Robert H. Abeles, Arthur A. Patchet
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Patent number: 4793949Abstract: There is disclosed a new vinyl monomer capable of forming polymeric vesicles, micelles, monolayers, and side-chain liquid crystalline polymers. The vinyl monomer is of the formula ##STR1## wherein R.sub.1 is substituted or unsubstituted long chain alkyl or aryl and R.sub.2 is a hydrogen atom, alkyl, or aryl.The side-chain liquid crystalline polymers can be formed by free radical polymerization or by anionic polymerizations techniques. The different reaction methods give polymers of different configuration; the anionic technique results in a polymer having a nitrogen atom in the backbone. The polymers are useful in film and fiber formation and display good toughness.Type: GrantFiled: June 3, 1986Date of Patent: December 27, 1988Assignee: University of Southern MississippiInventors: Lon J. Mathias, Robert E. Hermes
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Patent number: 4762829Abstract: A novel polyprenyl compound such as a polyprenyl carboxylic acid amide is disclosed. It has antithrombic and antiplatelet aggregation activity.Type: GrantFiled: October 23, 1986Date of Patent: August 9, 1988Assignee: Eisai Co., Ltd.Inventors: Isao Yamatsu, Takeshi Suzuki, Shinya Abe, Kouji Nakamoto, Akiharu Kajiwara, Tohru Fujimori, Koukichi Harada, Shinichi Kitamura
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Patent number: 4762548Abstract: Herbicidally active thiolcarbamates are employed in combination with a certain amide extender compound, the latter in sufficient quantity to minimize soil degradation and to prolong the soil life of the former. As a result, the herbicidal effectiveness of the thiolcarbamate herbicide is significantly enhanced and prolonged, rendering a single application or multiple applications of the herbicide effective over a longer period of time. Such herbicidal compositions can optionally contain a non-phytotoxic antidotally effective amount of thiolcarbamate herbicide antidote.Type: GrantFiled: August 12, 1985Date of Patent: August 9, 1988Assignee: Stauffer Chemical Co.Inventors: Reed A. Gray, Ferenc M. Pallos
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Patent number: 4745218Abstract: .alpha.-Vinyl-.alpha.-aminocarboxylic acids of the general formula: ##STR1## where * indicates a center of asymmetry and R is hydrogen, deuterium, lower alkyl, allyl, benzyl, or benzyl substituted 1 to 3 times by alkyl, alkoxy, fluorine or chlorine and produced enantioselectively from L-methionine by a multistep process.Type: GrantFiled: October 8, 1986Date of Patent: May 17, 1988Assignee: Degussa AGInventors: Dieter Seebach, Theodor Weber
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Patent number: 4727062Abstract: Described are 3-halovinylglycines and their amino acid dipeptide and oligopeptide conjugates, a new class of efficient antibacterial agents, pharmaceutical compositions containing them as active ingredients, and methods of synthesis. The compounds are thought to interfere in bacterial cell wall synthesis.Type: GrantFiled: March 17, 1986Date of Patent: February 23, 1988Assignee: Merck & Co., Inc.Inventors: David Taub, Robert H. Abeles, Arthur A. Patchett
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Patent number: 4710574Abstract: Disclosed is the hydrocarboxylation of defined enamides with CO and a compound ROH to make amino acids or amido esters, either of which can be hydrolyzed to .alpha.-amino acids.Type: GrantFiled: November 16, 1983Date of Patent: December 1, 1987Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, James D. Burrington
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Patent number: 4694103Abstract: A novel, one-pot procedure for the preparation of N-acryloyl-.alpha.-amino acids involves the steps of:(i) reacting a ketone, an ammonium salt, and a cyanide salt in water, optionally in the presence of ammonium hydroxide and a co-solvent, to form an aminonitrile;(ii) acryloylating the aminonitrile in aqueous media to afford an acrylamidonitrile; and(iii) hydrolyzing with aqueous acid the acrylamidonitrile to provide the N-acryloyl-.alpha.-amino acid.Type: GrantFiled: May 19, 1986Date of Patent: September 15, 1987Assignee: Minnesota Mining and Manufacturing CompanyInventors: Larry R. Krepski, Howell K. Smith, II, Jerald K. Rasmussen, Steven M. Heilmann
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Patent number: 4684722Abstract: Antibacterial activity is exhibited by monocyclic .beta.-lactam antibiotics having in the 1-position an --O--SO.sub.3 H activating group and in the 3-position an acylamino group of the formula ##STR1## wherein R.sub.3 and R.sub.4 are each independently hydrogen or alkyl.Type: GrantFiled: January 6, 1986Date of Patent: August 4, 1987Assignee: E. R. Squibb & Sons, Inc.Inventor: Joseph E. Sundeen
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Patent number: 4684483Abstract: An N-substituted amino acids can be prepared by the steps of: bringing together under reaction condition glyoxal and a source of sulfur dioxide in an aqueous medium to produce a sulfonated intermediate; and introducing into said medium a nitrogen compound selected from the group consisting of ammonia, a primary amine, and a secondary amine, into said medium containing said intermediate to produce said N-substituted amino acid.Type: GrantFiled: September 23, 1985Date of Patent: August 4, 1987Assignee: Monsanto CompanyInventors: Thomas J. Richard, William H. Miller
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Patent number: 4668703Abstract: This invention is for .gamma.-allenyl-.gamma.-aminobutyric acid derivatives which are .gamma.-aminobutyric acid transaminase inhibitors.Type: GrantFiled: July 1, 1985Date of Patent: May 26, 1987Assignee: Syntex (U.S.A.) Inc.Inventors: Alexander Krantz, Arlindo L. Castelhano, Diana H. Pliura
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Patent number: 4661510Abstract: Novel .alpha.-allenic-.alpha.-amino acids which are enzyme inhibitors of the suicide or k.sub.cat type are disclosed herein.Type: GrantFiled: October 21, 1985Date of Patent: April 28, 1987Assignee: Syntex (U.S.A.) Inc.Inventors: Alexander Krantz, Arlindo L. Castelhano
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Patent number: 4655975Abstract: Polycarboxylates such as disodium diglycolate can form peroxyhydrates becoming a solid source of hydrogen peroxide. Upon dissolution in water, these poly(carboxylates and/or sulfonates) both form a chelant and hydrogen peroxide. This combination is particularly useful to form aqueous cleaning solutions for use in cleaning laundry, dishes and the like.Type: GrantFiled: January 27, 1986Date of Patent: April 7, 1987Assignee: The Dow Chemical CompanyInventor: Karel A. J. Snoble
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Patent number: 4629736Abstract: Fatty acid derivatives represented by the general formula ##STR1## and salts thereof. The compounds of this invention have excellent fibrinolytic action and a highly improved solubility.Type: GrantFiled: September 28, 1984Date of Patent: December 16, 1986Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Shin-ichi Tsukamoto, Yoshinobu Nagano, Kimio Katsuda
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Patent number: 4613691Abstract: Amino acids can be easily prepared by reducing unsaturated hydantoins to the corresponding saturated hydantoins by hydrogenating the unsaturated hydantoin using either Raney Nickel catalyst in the presence of more than a stoichiometric amount of caustic or by using zinc and hydrochloric acid followed by hydrolyzing the resultant composition with at least 3 molar equivalents of an alkali metal hydroxide to produce a racemate of an alpha amino acid. The amino acid in suitable derivative form can then be resolved particularly using a two-phase solvent system. The residual isomer of the amino acid remaining after the resolution process can then be racemized using either pyridoxal-5-phosphate or an aliphatic acid in combination with an aldehyde or a ketone. By these procedures, it is possible to obtain high yields of amino acids.Type: GrantFiled: July 8, 1985Date of Patent: September 23, 1986Assignee: Stauffer Chemical CompanyInventors: Stanley B. Mirviss, Mark W. Empie
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Patent number: 4585892Abstract: .alpha.-Alkylated, acyclic .alpha.-aminocarboxylic acids of the formula ##STR1## where * represents a center of asymmetry, R.sup.1 is a lower alkyl, allyl, benzyl or substituted benzyl group and R.sup.2 is a lower alkyl, methoxymethyl, lower alkylmercaptoethyl, phenyl, phenyl substituted with alkyl or alkoxy, benzyl, or benzyl substituted with alkyl, alkoxy or halo are produced by an enantio-selective plural step process from the corresponding .alpha.-aminocarboxylic acid monomethyl or monoethyl amide. A particular advantage of the new process is that there can be produced from one educt-enantiomer, i.e. from an (S)- or an (R)-.alpha.-aminocarboxylic acid, selectively depending on the reaction conditions used the two enantiomeric forms of the desired .alpha.-alkyl-.alpha.-aminocarboxylic acid.Type: GrantFiled: September 27, 1984Date of Patent: April 29, 1986Assignee: Degussa AktiengesellschaftInventors: Dieter Seebach, Reto Naef
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Patent number: 4582931Abstract: A process for the preparation of 2-Deutero-D-serine and its fluorination is disclosed.Type: GrantFiled: December 24, 1984Date of Patent: April 15, 1986Assignee: Merck & Co., Inc.Inventors: Edward J. J. Grabowski, Paul J. Reider
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Patent number: RE32952Abstract: A novel, one-pot procedure for the preparation of N-acryloyl-.alpha.-amino acids involves the steps of:(i) reacting a ketone, an ammonium salt, and a cyanide salt in water, optionally in the presence of ammonium hydroxide and a co-solvent, to form an aminonitrile;(ii) acryloylating the aminonitrile in aqueous media to afford an acrylamidonitrile; and(iii) hydrolyzing with aqueous acid the acrylamidonitrile to provide the N-acryloyl-.alpha.-amino acid.Type: GrantFiled: December 30, 1987Date of Patent: June 13, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventors: Larry R. Krepski, Howell K. Smith, II, Jerald K. Rasmussen, Steven M. Heilmann