Amide In Acid Moiety Patents (Class 560/41)
  • Patent number: 4883900
    Abstract: Dipeptide alkyl esters whose alkyl group contains 3 to 7 carbon atoms can be converted to the corresponding methyl ester compound by a rapid, gentle transesterification in anhydrous methanol in the presence of an alkali metal alcoholate, without racemization occuring on the two chiral carbon atoms.
    Type: Grant
    Filed: July 12, 1988
    Date of Patent: November 28, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Reinhold Keller, Merten Schlingmann, Martin Platen
  • Patent number: 4883815
    Abstract: Hydrocinnamic acid derivatives of the formula ##STR1## wherein one or two of the symbols R.sup.1 to R.sup.4 are halogen or methoxy and the others are hydrogen;R.sup.5 is hydrogen or phenyl;R.sup.6 is a residue of the formula ##STR2## R.sup.7 is (C.sub.1 -C.sub.4)-alkyl, (C.sub.2 -C.sub.5)-alkanoylamino-(C.sub.2 -C.sub.5)-alkyl, amino or (C.sub.1 -C.sub.4)-alkoxyphenyl;R.sup.8 and R.sup.9 each, independently, are hydrogen or (C.sub.1 -C.sub.4)-alkyl;R.sup.10 is hydrogen and R.sup.11 is hydroxy or R.sup.10 and R.sup.11 taken together are oxo;R.sup.12 is hydrogen, (C.sub.1 -C.sub.10)-alkyl, pyridylmethyl or carbamoylmethyl;R.sup.13 is hydrogen, (C.sub.1 -C.sub.4)-alkyl and R.sup.14 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, pyridyl, phenyl-(C.sub.1 -C.sub.4)-alkyl, carboxy-(C.sub.1 -C.sub.4)-alkyl, carbamoyl-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy carbonyl-(C.sub.1 -C.sub.4)-alkyl, di-(C.sub.1 -C.sub.4)-alkoxy carbonyl-C.sub.2 -C.sub.5)-alky, piperidino-C.sub.2 -C.sub.
    Type: Grant
    Filed: July 5, 1988
    Date of Patent: November 28, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Aschwenden, Rene Imhof, Roland Jakob-Roetne, Emilio Kyburz
  • Patent number: 4879398
    Abstract: A process for making 2,6-disubstituted tyrosine by the noble metal coupling of a disubstituted aromatic halide or diazonium salt with an amino-protected 2-aminoacrylic acid to form a (Z)-.beta.-(disubstituted phenyl)-.alpha.-acylaminoacrylate, and asymmetrically hydrogenating the acrylate to produce the 2,6-disubstituted tyrosine.
    Type: Grant
    Filed: December 31, 1987
    Date of Patent: November 7, 1989
    Assignee: Monsanto Company
    Inventors: Daniel P. Getman, Roy A. Periana, Dennis P. Riley
  • Patent number: 4879403
    Abstract: Compounds of the formula I ##STR1## in which the carboxyl group on carbon atom 3 is orientated in the endo-position relative to the bicyclic ring system of cis-configuration, and in which R.sup.1 denotes hydrogen, allyl, vinyl or a side-chain of a naturally occurring .alpha.-aminoacid, which may be protected, R.sup.2 denotes hydrogen, alkyl, alkenyl or aralkyl, Y denotes hydrogen or hydroxyl and Z denotes hydrogen, or Y and Z together denote oxygen, and X denotes alkyl, alkenyl or cycloalkyl, or aryl which is optionally mono-, di- or tri-substituted by alkyl, alkoxy, hydroxyl, halogen, nitro, amino, alkylamino, dialkylamino or methylenedioxy, or denotes indol-3-yl, a process for their preparation, agents containing these compounds and their use.
    Type: Grant
    Filed: November 2, 1988
    Date of Patent: November 7, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Volker Teetz, Rolf Geiger, Hansjorg Urbach, Reinhard Becker, Bernward Scholkens
  • Patent number: 4874822
    Abstract: The present invention provides a dramatically improved process for the preparation of acrylamide and methacrylamide functional monomers, oligomers, and polymers that avoids the use of acidic catalysts which can cause undesired side reactions. The present invention process involves reacting an alkenyl azlactone with a hydroxy functional compound in the presence of a catalytic amount of either a bicyclic amidine or a trivalent phosphorus compound. These efficient basic catalysts provide unexpectedly increased reaction rates under mild conditions.
    Type: Grant
    Filed: April 7, 1988
    Date of Patent: October 17, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Jerald K. Rasmussen, Steven M. Heilmann, Larry R. Krepski, Dean M. Moren
  • Patent number: 4873253
    Abstract: A phenylalanine derivative having the formula (I): ##STR1## wherein A represents ##STR2## B represents ##STR3## wherein m is 0, 1, or 2 and n is 3, 4, or 5; X represents (a) hydroxy, (b) nitro, (c) amino, (d) phenoxy which may be substituted with (i) halogen or (ii) nitro, (e) c.sub.1 -C.sub.4 alkyloxy which may be substituted wit (i) phenyl or (ii) benzoyl, (f) benzoyl, (g) pyridyloxy which may be substituted with (i) halogen or (ii) nitro, or (h) c.sub.1 -C.sub.4 alkyl which may by substituted with halogen;Y represents ##STR4## or --OR.sup.3 wherein R.sup.1 R.sup.2 are independently (a) hydrogen, (b) phenyl which may be substituted with (i) benzoyl, (ii) C.sub.1 -C.sub.4 alkylcarbonyl, (iii) C.sub.1 -C.sub.4 alkyl which may be further substituted with C.sub.1 -C.sub.4 alkoxycarbonyl or hydroxycarbonyl, (iv) C.sub.2 -C.sub.5 alkenyl which may be further substituted with hydroxycarbonyl or C.sub.1 -C.sub.4 alkoxycarbonyl, (v) C.sub.1 -C.sub.
    Type: Grant
    Filed: March 30, 1987
    Date of Patent: October 10, 1989
    Assignees: Shosuke Okamoto, Showa Denko Kabushiki Kaisha
    Inventors: Shosuke Okamoto, Yoshio Okada, Akiko Okunomiya, Taketoshi Naito, Yoshio Kimura, Morihiko Yamada, Norio Ohno, Yasuhiro Katsuura, Hiroshi Nojima, Takashi Shishikura
  • Patent number: 4873359
    Abstract: Synthesis of phenylserine ester (a) via benzaldehyde and glycine ester using serine hydroxymethyltransferase; and (b) via methyl benzoylacetate. Synthesis of hydroxy-aspartame or derivative by enzymatic coupling of phenylserine or derivative with aspartic acid or derivative. Hydrogenation of the coupled product to give as final product aspartame or analog with related processes and products.
    Type: Grant
    Filed: October 1, 1987
    Date of Patent: October 10, 1989
    Assignee: W. R. Grace & Co. - Conn.
    Inventors: Alan B. Chmurny, Akiva T. Gross, Robert J. Kupper, Rowena L. Roberts
  • Patent number: 4859788
    Abstract: Amino group containing curing component (A) for compounds (B) which contain epoxy or 1,3-dioxolan-2-one groups, comprising a reaction product of (a.sub.1) active CH alkyl esters of isocyanate adducts thereof with (a.sub.2) polyamines.Mixtures of (A) and (B) with or without diluents and additives give rapid curing even at low temperatures and high atmospheric humidity and are suitable in particular for paint formulations.
    Type: Grant
    Filed: April 7, 1988
    Date of Patent: August 22, 1989
    Assignee: Hoechst AG
    Inventors: Gerhard Brindopke, Claus Godau, Walter Weber
  • Patent number: 4852989
    Abstract: This invention relates to bleaching compounds and compositions that provide effective and efficient surface bleaching of textiles over a wide range of bleach solution temperatures. The bleaching compounds of the invention yield a peroxyacid with a polar amide link in the hydrophobic chain when used in the bleaching compositions. In a preferred embodiment, the bleaching compositions of the invention are also detergent compositions.
    Type: Grant
    Filed: May 8, 1987
    Date of Patent: August 1, 1989
    Assignee: The Procter & Gamble Company
    Inventors: Michael E. Burns, Frederick E. Hardy
  • Patent number: 4851563
    Abstract: A method for the removal of the formyl group from an ester of an N-formyl peptide or N-formyl aminoacid, in which the ester is reacted with urea in the presence of a polar solvent and a strong acid.
    Type: Grant
    Filed: September 9, 1986
    Date of Patent: July 25, 1989
    Assignee: Lark S.p.A.
    Inventors: Goffredo A. Bolis, Giuseppe Cantarini, Marco Da Col
  • Patent number: 4843062
    Abstract: Disclosed herein are N-acyl-N-napthoylglycines and methods of their preparation. The N-acyl-N-napthoylglycines are novel aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: June 27, 1989
    Assignee: American Home Products Corporation
    Inventors: Kazimir Sestanj, Jay E. Wrobel, Joseph M. Kelly
  • Patent number: 4837353
    Abstract: 2-(N-Phenylakyl-N-formyl)amino-3-hydroxy-2-propenoic acids are intermediates for mercaptoimidazolecarboxylic acids which are dopamine-.beta.-hydroxylase inhibitors.
    Type: Grant
    Filed: January 21, 1988
    Date of Patent: June 6, 1989
    Assignee: SmithKline Beckman Corporation
    Inventors: Joseph A. Finkelstein, Lawrence I. Kruse, Thomas B. Leonard
  • Patent number: 4837290
    Abstract: A composition of matter comprising an acrylamido-acyl or methacrylamido-acyl oligomer derived from at least one nucleophilic oligomer having at least one amino-, hydroxyl-, or thiol-substituted polyoxyalkylene, polyalkyleneimine, polyester, polyolefin, polyacrylate, or polysiloxane oligomer, said nucleophilic oligomer having a molecular weight in the range of 200 to 20,000 is disclosed. Also disclosed are free radically polymerizable monomer-containing compositions containing said oligomers as well as acrylamido- and methacrylamido-acylated polymers which are thermal or photocured products of said oligomers. In addition, a process is disclosed for providing said acrylamido- and methacrylamido-acylated oligomers which are useful, for example, in coatings, films, printing inks, adhesives, and saturants.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: June 6, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Jerald K. Rasmussen, Steven M. Heilmann, Frederick J. Palensky
  • Patent number: 4835302
    Abstract: A method for producing an indan derivative represented by the formula: ##STR1## by condensing an N-(.alpha.-alkoxycarbonylaralkyl)-.alpha.-amino acid with an N-(indan-2-yl)glycine alkyl or aralkyl ester in the presence of a diphenyl phosphorochloridate, and a method for producing another indan derivative having anti-hypertensive activity by using the above intermediate indan derivative are useful for industrial production of the indan derivative having anti-hypertensive activity.
    Type: Grant
    Filed: March 1, 1988
    Date of Patent: May 30, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Takeshi Kato, Tomoyuki Fujii
  • Patent number: 4835301
    Abstract: A process for producing stable .alpha.-L-aspartyl-L-phenylalanine methyl ester, which comprises heat-treating crystals of .alpha.-L-aspartyl-L-phenylalanine methyl ester having a water content of from 5 to 15% by weight based on wet crystals, at a temperature of higher than 50.degree. C. and lower than 80.degree. for at least 30 minutes.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: May 30, 1989
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Hidetoshi Wakamatsu, Shigeaki Irino, Tsuneo Harada, Akira Tokuda, Kiyotaka Oyama
  • Patent number: 4835303
    Abstract: A process for producing dry .alpha.-L-aspartyl-L-phenylalanine methyl ester, which comprises drying wet crystals of .alpha.-L-aspartyl-L-phenylalanine methyl ester by means of an air having an absolute humidity of at least 0.015 kg/kg or at most 0.01 kg/kg.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: May 30, 1989
    Assignee: Toyo Soda Manufacturing Company, Ltd.
    Inventors: Hideotoshi Wakamatsu, Shigeaki Irino, Tsuneo Harada, Akira Tokuda, Kiyotaka Oyama
  • Patent number: 4831180
    Abstract: A process for producing dry .alpha.-L-aspartyl-L-phenylalanine methyl ester having an improved solubility by drying wet crystals of .alpha.-L-aspartyl-L-phenylalanine methyl ester, characterized in that the wet crystals of .alpha.-L-aspartyl-L-phenylalanine methyl ester are granulated so that the specific surface area during the drying operation is at least 4 m.sup.2 /g, followed by drying.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: May 16, 1989
    Assignee: Toyo Soda Manufacturing Company, Ltd.
    Inventors: Hidetoshi Wakamatsu, Shigeaki Irino, Tsuneo Harada, Akira Tokuda, Hiyotaka Oyama
  • Patent number: 4831181
    Abstract: The invention relates to a process for the preparation of aspartylphenylalanine methyl ester from N-formylaspartylalanine methyl ester by treatment with an acid, characterized in that N-formylaspartylalanine methyl ester is treated at 30.degree.-60.degree. C. with at least 0.5 molar equivalent oxalic acid per mole of N-formylaspartylphenylalanine methyl ester in a solvent mixture in which N-formylaspartylphenylalanine methyl ester dissolves well and in which the oxalic acid salt of aspartylphenylalanine methyl ester is poorly soluble, after which the oxalic acid salt of aspartylphenylalanine methyl ester is removed by filtration, dissolved in water subsequently neutralized with the aid of an inorganic base with formation of free aspartylphenylalanine methyl ester.
    Type: Grant
    Filed: April 29, 1988
    Date of Patent: May 16, 1989
    Assignee: Stamicarbon B.V.
    Inventors: Wilhelmus H. J. Boesten, Bernardus H. N. Dassen
  • Patent number: 4824994
    Abstract: A method for the production of N-carbobenzoxy-.alpha.-L-aspartyl-L-phenylalanine methyl ester characterized by the reaction of L-phenylalanine methyl ester with fine N-carbobenzoxy-L-aspartic anhydride crystals, is disclosed.
    Type: Grant
    Filed: September 14, 1984
    Date of Patent: April 25, 1989
    Assignee: Ajinomoto Co., Inc.
    Inventors: Satoji Takahashi, Katsumi Sugiyama
  • Patent number: 4824217
    Type: Grant
    Filed: August 19, 1986
    Date of Patent: April 25, 1989
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Lawrence K. M. Chan, David Coates, Peter A. Gemmell, George W. Gray, David Lacey, Kenneth J. Toyne, Daniel J. S. Young, Matthew F. Bone, Adam Jackson, Richard M. Scrowston
  • Patent number: 4822818
    Abstract: New bicyclic compounds, inclusive of salts thereof, of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each represents hydrogen, hydroxyl or lower alkoxy, R.sup.3 is hydrogen or lower alkyl, R.sup.4 is hydrogen, lower alkyl, amino-lower-alkyl or acylamino-lower-alkyl, R.sup.5 is hydrogen, lower alkyl or aralkyl which may be substituted, R.sup.6 is hydroxyl, lower alkoxy, amino or lower alkylamino, and m and n each means 1 or 2, have inhibitory activities of angiotensin converting enzyme and bradykinin decomposing enzyme, and are useful as antihypertensive agents.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: April 18, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yoshikazu Oka, Kohei Nishikawa, Akio Miyake
  • Patent number: 4822907
    Abstract: A process for recovering .alpha.-L-aspartyl-L-phenylalanine methyl ester from a solution containing various methyl ester or demethylated derivatives of .alpha.-L-aspartyl-L-phenylalanine methyl ester and chloride ions is disclosed. This process uses a reverse osmosis membrane having a specific chloride inhibition rate to desalt and concentrate a solution containing a specified ratio of .delta.-L-aspartyl-L-phenylalanine methyl ester to its derivatives until a specific weight ratio of organic chloride ion to the sum of .alpha.-L-aspartyl-L-phenylalanine methyl ester and its derivatives is obtained. This desalted and concentrated solution is then contacted with an aqueous solvent containing methanol and hydrochloride acid to recover high yields of .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride.
    Type: Grant
    Filed: June 3, 1987
    Date of Patent: April 18, 1989
    Assignee: Ajinomoto Co., Inc.
    Inventors: Katsumi Sugiyama, Takashi Yamashita, Toshihide Yukawa
  • Patent number: 4820861
    Abstract: N-formyl-.alpha.-L-aspartyl-L-phenylalanine methyl ester is obtained by reacting L-phenylalanine methyl ester with N-formyl-L-aspartic acid anhydride in a reaction solvent containing acetic acid or acetic acid and formic acid in a complete mixing type continuous reaction mode.
    Type: Grant
    Filed: November 17, 1986
    Date of Patent: April 11, 1989
    Assignee: Ajinomoto Co., Inc.
    Inventors: Toshihide Yukawa, Haruo Kawasaki, Masao Nakamura, Takashi Yamashita, Toshiaki Tsuji
  • Patent number: 4816484
    Abstract: A compound of D-phenylalanine derivative for hypoglycemic use, represented by the general formula ##STR1## R.sup.1 is selected from hydrogen, alkyl of 1 to 5 carbon atoms, aryl of 6 to 12 carbon atoms, aralkyl of 6 to 12 carbon atoms, ##STR2## --CH.sub.2 CO.sub.2 R.sup.3, --CH(CH.sub.3)--OCO--R.sup.3, and --CH.sub.2 --OCO--C(CH.sub.3).sub.3 ; R.sup.2 is selected from groups comprising aryl of 6 to 12 carbon atoms, a hetero six-membered ring, a hetero five-membered ring, cycloalkyl, or cycloalkenyl, any of which groups may have one or more substituents; and R.sup.3 is selected from hydrogen and alkyl of 1 to 5 carbon atoms; the salts thereof, and precursors which can be converted thereto in the human or animal body.Some of the compounds are novel per se.
    Type: Grant
    Filed: January 21, 1988
    Date of Patent: March 28, 1989
    Assignee: Ajinomoto Co., Inc.
    Inventors: Shigeshi Toyoshima, Yoshiko Seto, Hisashi Shinkai, Koji Toi, Izumi Kumashiro
  • Patent number: 4812163
    Abstract: A phenoxyacetic acid represented by the following formula (I) ##STR1## wherein X represents a halogen atom or CF.sub.3, R.sup.1 and R.sup.3 are identical or different and each represents a hydrogen atom or an alkyl group having not more than 5 carbon atoms, R.sup.2 represents a hydrogen atom, a lower alkyl group, a phenyl group, a benzyl group, --CH.sub.2 CH.sub.2 SCH.sub.3, --CH.sub.2 OH, --CH(CH.sub.3)OH, --CH.sub.2 SH, --CH.sub.2 COOCH.sub.3, ##STR2## or R.sup.2 and R.sup.3 together may form --CH.sub.2 CH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 CH(OH)--, and n is 0, 1 or 2, or a salt at the carboxyl group of the phenoxyacetic acid of the above formula in which R.sup.1 is a hydrogen atom. The compound is useful, as a herbicide, for eradicating weeds, especially narrow-leaved weeds.
    Type: Grant
    Filed: March 18, 1988
    Date of Patent: March 14, 1989
    Assignee: Teijin, Limited
    Inventors: Toshiyuki Hiramatsu, Shizuo Azuma, Koji Nakagawa, Yataro Ichikawa
  • Patent number: 4810817
    Abstract: Synthesis of phenylserine ester (a) via benzaldehyde and glycine ester using serine hydroxymethyltransferase; and (b) via methyl benzoylacetate. Synthesis of hydroxy-aspartame or derivative by enzymatic coupling of phenylserine or derivative with aspartic acid or derivative. Hydrogenation of the coupled product to give as final product aspartame or analog with related processes and products.
    Type: Grant
    Filed: October 1, 1987
    Date of Patent: March 7, 1989
    Assignee: W. R. Grace & Co.
    Inventors: Alan B. Chmurny, Akiva T. Gross, Robert J. Kupper, Rowena L. Roberts
  • Patent number: 4810816
    Abstract: A process for producing N-formyl-aspartylphenylalanine or its methyl ester, wherein aspartic acid is reacted with formic acid and acetic anhydride in approximately stoichiometric quantities in the presence or absence of a catalyst and phenylalanine or its methyl ester is directly added to the dehydration mixture. This process has a higher yield of the desired N-formyl-dipeptide and minimizes the amount of by-products and unreacted starting materials.
    Type: Grant
    Filed: September 22, 1987
    Date of Patent: March 7, 1989
    Assignee: Ajinomoto Co., Inc.
    Inventors: Toshiaki Tsuji, Shinichi Kishimoto
  • Patent number: 4810818
    Abstract: A process for producing dry .alpha.-L-aspartyl-L-phenylalanine methyl ester having an improved solubility from wet crystals of .alpha.-L-aspartyl-L-phenylalanine methyl ester having a water content of at least 20% by weight, which comprises drying the wet crystals at a temperature of higher than 50.degree. C. to obtain moist crystals having a water content of less than 20 and more than 15% by weight, then drying the moist crystals at a temperature of not higher than 50.degree. C. to obtain semi-dry crystals having a water content of less than 5% by weight, and further drying the semi-dry crystals at a temperature of higher than 50.degree. C. to obtain dry crystals of .alpha.-L-aspartyl-L-phenylalanine methyl ester.
    Type: Grant
    Filed: July 28, 1987
    Date of Patent: March 7, 1989
    Assignee: Toyo Soda Manufacturing Co., Ltd
    Inventors: Hidetoshi Wakamatsu, Shigeaki Irino, Tsuneo Harada, Akira Tokuda, Kiyotaka Oyama
  • Patent number: 4801721
    Abstract: Methods for the alkylation of substituted amines with trifluorate esters is disclosed.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: January 31, 1989
    Inventors: James W. Ryan, Alfred Chung
  • Patent number: 4801732
    Abstract: This invention relates to an improved process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester. More specifically, it relates to a process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester which comprises treating, as a raw material, N-formyl-.alpha.-L-aspartyl-L-phenylalanine in methanol in the presence of an acid to form .alpha.-L-aspartyl-L-phenylalanine dimethyl ester, hydrolyzing the .alpha.-L-aspartyl-L-phenylalanine dimethyl ester by bringing it into contact with hydrochloric acid in the presence of methanol as desired, separating the thereby-precipitated .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride and neutralizing the hydrochloride. Further, this invention also provides a process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester capable of using, as a raw material, N-formyl-.alpha.-L-aspartyl-L-phenylalanine which contains N-formyl-.beta.-L-aspartyl-L-phenylalanine in an amount of 30% by weight or less.
    Type: Grant
    Filed: March 22, 1988
    Date of Patent: January 31, 1989
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Ryuichi Mita, Takeshi Oura, Chojiro Higuchi, Toshio Katoh, Akihiro Yamaguchi
  • Patent number: 4793949
    Abstract: 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: Grant
    Filed: June 3, 1986
    Date of Patent: December 27, 1988
    Assignee: University of Southern Mississippi
    Inventors: Lon J. Mathias, Robert E. Hermes
  • Patent number: 4780561
    Abstract: Disclosed herein is a process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride from 5-benzyl-3,6-dioxo-2-piperazine acetic acid or its methyl ester, prepared without using L-penylalanine methyl ester which involves problems in its stability, as a raw material. Specifically, the process comprises: bringing 5-benzyl-3,6-dioxo-2-piperazine acetic acid in the presence of methanol or 5-benzyl-3,6-dioxo-2-piperazine acetic acid methyl ester in the presence or absence of methanol into contact with hydrochloric acid; isolating the thereby deposited .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride; and neutralizing said hydrochloride with an alkali as required. Preparation processes of 5-benzyl-3,6-dioxo-2-piperazine acetic acid or its methyl ester are also disclosed.
    Type: Grant
    Filed: December 9, 1987
    Date of Patent: October 25, 1988
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Ryuichi Mita, Takeshi Oura, Toshio Katoh, Chojiro Higuchi, Akihiro Yamaguchi
  • Patent number: 4778916
    Abstract: The present invention relates to a process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride. .alpha.-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride is prepared by a process comprising: condensating N-formyl-L-aspartic acid anhydride and L-phenylalanine in water or in water containing methanol at a pH in the range of 7-12 to form N-formyl-.alpha.-L-aspartyl-L-phenylalanine; acidifying the reaction mixture successively with hydrochloric acid in the presence of methanol without isolating the N-formyl-.alpha.-L-aspartyl-L-phenylalanine so as to bring it into contact with hydrochloric acid in the presence of methanol for reaction and thereby to deposit .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride; separating the .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride; and neutralizing said hydrochloride as required.
    Type: Grant
    Filed: November 17, 1987
    Date of Patent: October 18, 1988
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Takeshi Oura, Akihiro Yamaguchi
  • Patent number: 4777276
    Abstract: A composition of matter comprising an acrylamido-acyl or methacrylamido-acyl oligomer derived from at least one nucleophilic oligomer having at least one amino-, hydroxyl-, or thiol-substituted polyoxyalkylene, polyalkyleneimine, polyester, polyolefin, polyacrylate, or polysiloxane oligomer, said nucleophilic oliogmer having a molecular weight in the range of 200 to 20,000 is disclosed. Also disclosed are free radically polymerizable monomer-containing compositions containing said oligomers as well as acrylamido- and methacrylamido-acylated polymers which are the thermal or photocured products of said oligomers. In addition, a process is disclosed for providing said acrylamido- and methacrylamido-acylated oligomers which are useful, for example, in coatings, films, printing inks, adhesives, and saturants.
    Type: Grant
    Filed: October 29, 1981
    Date of Patent: October 11, 1988
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Jerald K. Rasmussen, Steven M. Heilmann, Frederick J. Palensky
  • Patent number: 4764619
    Abstract: An optically active compound having the formula: ##STR1## wherein each of Z and Z' is a single bond, --COO--, --OCO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 -- or --CH.sub.2 O--, R is an alkyl group having from 1 to 12 carbon atoms, an alkoxyl group having from 1 to 12 carbon atoms, a cyano group or a halogen atom, each of rings A and B is a 1,4-di-substituted phenylene group or a trans-1,4-di-substituted cyclohexylene group, n is 0 or 1, X is ##STR2## wherein * indicates an optical center, and R' is an alkyl group having from 2 to 12 carbon atoms or ##STR3## where R" is a hydrogen atom, an alkyl or alkoxy group having from 1 to 12 carbon atoms, provided that when X is ##STR4## R is the alkyl group or the alkoxy group.
    Type: Grant
    Filed: March 21, 1986
    Date of Patent: August 16, 1988
    Assignee: Asahi Glass Company Ltd.
    Inventors: Tomoki Gunjima, Ryutaro Takei, Eriko Aoyama
  • Patent number: 4761495
    Abstract: The present invention is directed to a composition and method relating to the preparation of aspartyl peptides having the general formula: ##STR1## where the radical-NHR represents an amino acid or peptide group. In the method, a .beta.-monoester of aspartic acid having the general formula: ##STR2## where R.sub.1 represents a hydrocarbon-containing radical, is reacted with a .beta.-dicarbonyl compound, preferably ethylacetoacetate to protect the aspartyl amino group and form an enamine. The enamine is then coupld to an amino acid or peptide, following which any protecting groups are removed to yield .alpha.-aspartyl peptides without any .beta.-isomer. In its composition aspects, the present invention is directed to novel enamines resulting from reaction of the .beta.-monoester of aspartic acid with a .beta.-dicarbonyl compound.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: August 2, 1988
    Assignee: Isochem S.A.
    Inventors: Didier Wirth, Dominique Gibert, Annie Boutin
  • Patent number: 4760164
    Abstract: A process for preparing an .alpha.-L-aspartyl-L-phenylalanine methyl ester which comprises the steps of reacting formyl-L-aspartic anhydride with L-phenylalanine in the presence of water at a high pH, to produce formyl-.alpha.-L-aspartyl-L-phenylalanine; removing the formyl group from the formyl-.alpha.-L-aspartyl-L-phenylalanine and esterifying the resultant compound with methanol and hydrogen chloride to produce the hydrogen chloride salt of .alpha.-L-aspartyl-L-phenylalanine methyl ester; neutralizing the hydrogen chloride salt of .alpha.-L-aspartyl-L-phenylalanine methyl ester; and filtering the neutralized solution to produce .alpha.-L-aspartyl-L-phenylalanine methyl ester.
    Type: Grant
    Filed: February 25, 1986
    Date of Patent: July 26, 1988
    Assignee: Korea Green Cross Corporation
    Inventors: Jung Y. Park, Gug Y. Cheon, Do Y. Ahn, Dong J. Park
  • Patent number: 4755619
    Abstract: Compounds of formula (II) ##STR1## wherein R.sub.1 and R.sub.2 are each separately selected from hydrogen, alkyl, alkenyl and alkynyl groups having up to a maximum of four carbon atoms and being unsubstituted, and alkyl, alkenyl and alkynyl groups having up to a maximum of three carbon atoms and being substituted by one, or in the case of fluoro by one or more, substitutents but with the proviso that when R.sub.1 is hydrogen then R.sub.2 is hydrogen or methyl, or R.sub.1 and R.sub.2 together constitute an ethylene bridging group, and R.sub.3 is a group which under physiological conditions undergoes elimination with the formation of a 3,5-dioxopiperazinyl ring, with the further proviso that the compound is in the meso or erythro configuration when each of R.sub.1 and R.sub.
    Type: Grant
    Filed: March 24, 1986
    Date of Patent: July 5, 1988
    Assignee: National Research Development Corporation
    Inventors: Andrew M. Creighton, William A. Jeffery
  • Patent number: 4745210
    Abstract: This invention relates to an improved process for preparing N-formyl-.alpha.- aspartyl phenylalanine. More specifically, it relates to a process for preparing N-formyl-.alpha.-aspartyl phenylalanine by condensating N-formyl aspartic acid anhydride and phenylalanine which comprises effecting the condensation reaction in a water medium while maintaining the pH during the reaction in the range of 7-12 and at a reaction temperature of 50.degree. C. or below.
    Type: Grant
    Filed: December 4, 1985
    Date of Patent: May 17, 1988
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Takeshi Oura, Akihiro Yamaguchi
  • Patent number: 4743691
    Abstract: 2-(Fluoromethyl or chloromethyl)-2,5-diaminopentanoic acid, 2-(fluoromethyl or chloromethyl)-2,6-diaminohexanoic acid, and 2-fluoromethyl-2-amino-5-guanidinopentanoic acid, and certain derivatives thereof, are inhibitors of ornithine decarboxylase. Methods of preparing the compounds and derivatives are also described.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: May 10, 1988
    Assignee: Merrell Dow France et Cie
    Inventors: Philippe Bey, Michel Jung
  • Patent number: 4738803
    Abstract: Derivatives having the general formula: ##STR1## in which the various radicals, A,B,X,R.sub.1, R.sub.2, R.sub.3 and n have indicated definitions. These compounds have in particular enkephalinase-inhibiting, antalgic, antidepressive, antidiarrhea and hypotensive activities.
    Type: Grant
    Filed: August 22, 1986
    Date of Patent: April 19, 1988
    Inventors: Bernard Roques, Jean-Charles Schwartz, Jeanne-Marie Lecomte
  • Patent number: 4734120
    Abstract: Dipeptides containing C-terminal phosphinothricin of the formula ##STR1## in which phosphinothricin is attached to a--preferably natural--amino acids at the amino group are effective herbicides in the pre-emergence and post-emergence techniques. The compounds are obtained, for example, by reacting phosphinothricin with the hydroxysuccinimide ester of an amino acids which is protected at the amino group in the presence of a base and subsequently splitting off the protective groups.
    Type: Grant
    Filed: December 12, 1986
    Date of Patent: March 29, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz Kehne, Klaus Bauer, Hermann Bieringer
  • Patent number: 4734424
    Abstract: Bicycloheptane substituted amide prostaglandin analogs are provided having the structural formula ##STR1## wherein m is 0 to 4; A is --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --; n is 1 to 5; Q is --CH.dbd.CH--, --CH.sub.2 --, ##STR2## or a single bond; R is CO.sub.2 H, CO.sub.2 alkyl, CO.sub.2 alkali metal, CO.sub.2 polyhydroxyamine salt, --CH.sub.2 OH, ##STR3## wherein R.sup.4 and R.sup.5 are the same or different and are H, lower alkyl, hydroxy, lower alkoxy or aryl, at least one of R.sup.4 and R.sup.5 being other than hydroxy and lower alkoxy; p is 1 to 4; R.sup.1 is H or lower alkyl; q is 1 to 12; R.sup.2 is H or lower alkyl; and R.sup.3 is H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aryloxy, arylalkyloxy, amino, alkylamino arylamino, arylalkylamino, lower alkyl-S-, aryl-S-, arylalkyl-S-, ##STR4## (wherein n' is 0, 1 or 2), alkylaminoalkyl, arylaminoalkyl, arylalkylaminoalkyl, alkoxyalkyl, aryloxyalkyl or arylalkoxyalkyl.
    Type: Grant
    Filed: September 24, 1986
    Date of Patent: March 29, 1988
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Steven E. Hall, Joyce Reid
  • Patent number: 4730076
    Abstract: The present invention relates to a process for producing .alpha.-aspartyl-phenylalanine ester represented by the general formula ##STR1## wherein R' represents an alkyl group having 1 to 4 carbon atoms, by reducing an N-protected-N-hydroxymethyl-.alpha.-aspartyl-phenylalanine ester represented by the general formula ##STR2## wherein R represents an organic mioety which can be substituted reductively by hydrogen, and R' is as defined above, with hydrogen gas or formic acid, in the presence of a reduction catalyst and an aromatic primary amine. According to the present invention, there can be obtained a high purity .alpha.-aspartyl-phenylalanine ester with a high yield.
    Type: Grant
    Filed: December 16, 1986
    Date of Patent: March 8, 1988
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tadashi Fujii, Hiroshi Yagiuchi, Akikazu Mitsunobu, Shigeru Aoki, Makoto Tsuda
  • Patent number: 4721803
    Abstract: In the process of hydrocarboxylating an .alpha.-enamide with CO and an organic hydroxyl compound to produce a N-acyl-.alpha.-amino acid ester, the improvement comprising using as the organic hydroxyl compound reactant, an organic hydroxyl compound which has a chiral center that is essentially all L or D, thereby producing a reaction mixture having essentially no enantiomeric pairs and containing diastereomeric N-acyl-.alpha.-amino acid esters having two chiral centers.
    Type: Grant
    Filed: October 29, 1985
    Date of Patent: January 26, 1988
    Assignee: The Standard Oil Company
    Inventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
  • Patent number: 4720539
    Abstract: Polyimide precursor compositions are described which may be prepared by rting a biprimary aromatic diamine with a diester-diacid or an aromatic tetraacid, and then with the substantially stoichiometrical complement of an aromatic dianhydride.The polyimide precursor compositions are used in the manufacture of insulating coatings, films, impregnating or enamelling varnishes for electric wires etc., and have excellent qualities of flexibility, adhesiveness and heat resistance.
    Type: Grant
    Filed: September 10, 1986
    Date of Patent: January 19, 1988
    Assignee: Centre d'Etudes des Materiaux Organiques pour Technologies Avancees
    Inventors: Guy Rabilloud, Paul Marriagi, Serge Gonzales, Bernard Sillion
  • Patent number: 4714777
    Abstract: The subject invention relates to novel cyclopropanone hydrate derivatives of the structural formula ##STR1## whereinR.sub.1 and R.sub.2 are selected from the group consisting of --H, --(CH.sub.2).sub.n -- where n is an integer between 1 and 20, preferably 2 and 10, --COCH.sub.2 NH.sub.2, and ##STR2## and R.sub.3 and R.sub.4 selected from the group consisting of --H, --OH, 13 NH.sub.2, --CN, --COOR.sub.5, --COOH, --SH, --(CH.sub.2).sub.n OH, --(CH.sub.2).sub.n NH.sub.2, --(CH.sub.2).sub.n COOH, --(CH.sub.2).sub.n COOR.sub.5, --CCH.sub.3 OH (CH.sub.2).sub.n COOH, halogen and C.sub.7 -C.sub.10 arakyls, where n is an integer between 1 and 20, preferably 1 and 10, and R.sub.5 is an alkyl radical having between 1 and 20, preferably 1 and 10, carbon atoms;and to a process for the synthesis thereof.
    Type: Grant
    Filed: January 6, 1986
    Date of Patent: December 22, 1987
    Assignee: University of Pittsburgh
    Inventors: Paul Dowd, Christopher Kaufman, Robert H. Abeles
  • Patent number: 4710574
    Abstract: 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: Grant
    Filed: November 16, 1983
    Date of Patent: December 1, 1987
    Assignee: The Standard Oil Company
    Inventors: Mark C. Cesa, James D. Burrington
  • Patent number: 4709075
    Abstract: Alkyl N-maleylphenylalanate is prepared by reacting the starting material alkyl L-phenylalanate and maleic anhydride in aqueous solution at a pH of at most 7.5. The reaction products can be isomerized with dipolar aprotic solvents into the corresponding fumaric acid monoamides and thus can be used as an intermediate in the preparation of alkyl .alpha.-L-aspartyl-L-phenylalanate.
    Type: Grant
    Filed: December 6, 1985
    Date of Patent: November 24, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Reinhold Keller
  • Patent number: H645
    Abstract: A process for the isomerization of maleic acid, its monoesters and monoamides in the presence of thiourea in anhydrous conditions at elevated temperature to the corresponding fumaryl forms yields intermediates which are useful in the synthetic pathways of aspartame and other useful polypeptides.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: June 6, 1989
    Assignee: The NutraSweet Company
    Inventor: Hugh L. Dryden, Jr.